JP4963248B2 - Aromatic amine compounds - Google Patents

Description

  The present invention relates to an aromatic amine compound, and a light-emitting element, a light-emitting device, and an electronic device using the aromatic amine compound.

In recent years, research and development of light-emitting elements using light-emitting compounds have been actively conducted. The basic structure of these light-emitting elements is such that a layer containing a light-emitting organic compound is sandwiched between a pair of electrodes. By applying a voltage to this element, electrons and holes are injected from the pair of electrodes to the layer containing a light-emitting organic compound, and current flows. Then, these carriers (electrons and holes) recombine, whereby the light-emitting organic compound forms an excited state, and emits light when the excited state returns to the ground state. Due to such a mechanism, such a light-emitting element is referred to as a current-excitation light-emitting element.

Such a light-emitting element is formed of an organic thin film having a thickness of, for example, about 0.1 μm. In addition, since the time from the injection of the carrier to the light emission is about 1 μsec or less, one of the features is that the response speed is very fast. These characteristics are considered suitable for flat panel display elements.

In addition, since these light-emitting elements are formed in a film shape, planar light emission can be easily obtained by forming a large-area element. This is a feature that is difficult to obtain with a point light source typified by an incandescent bulb or LED, or a line light source typified by a fluorescent lamp, and therefore has a high utility value as a surface light source applicable to illumination or the like.

  With respect to such a light emitting element, there are many problems depending on the material in improving the element characteristics, and improvement of the element structure, material development, and the like have been performed in order to overcome these problems.

  For example, Non-Patent Document 1 describes a light-emitting element using a blue light-emitting material.

Meng-Huan Ho, Yao-Shan Wu and Chin H. et al. Chen, 2005 SID International Symposium Digest of Technical Papers, Vol. XXXVI. p802-805

  In the light-emitting element described in Non-Patent Document 1, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) is used as a layer in contact with the light-emitting layer. However, NPB has low singlet excitation energy, and there is a possibility that energy is transferred from a light emitting material in an excited state. In particular, in the case of a light-emitting material that emits blue light having a short wavelength, the energy level in the excited state is high, and thus there is a higher possibility that energy is transferred to NPB. When energy is transferred to the NPB, there is a problem that the light emission efficiency of the light emitting element is lowered.

  Therefore, an object of the present invention is to provide a novel aromatic amine compound.

  Another object is to provide a light-emitting element, a light-emitting device, and an electronic device with high light emission efficiency.

One aspect of the present invention is an aromatic amine compound represented by the general formula (1).

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and A ¹ has 6 to 25 carbon atoms. Ar ¹ represents an aryl group having 6 to 25 carbon atoms, and α represents any one of the substituents represented by the general formula (1-1) to the general formula (1-4). In the general formulas (1-1) to (1-4), R ¹¹ and R ¹² are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl having 6 to 12 carbon atoms. Any one of the groups, R ^{13 to} R ¹⁹ and R ^{21 to} R ²⁹ and R ^{31 to} R ³⁹ and R ^{41 to} R ⁴⁹ each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  Of the aromatic amine compounds represented by the general formula (1), an aromatic amine compound represented by the general formula (3) is preferable.

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and Ar ¹ represents 6 to 25 carbon atoms. In addition, α represents any one of the substituents represented by the general formula (3-1) to the general formula (3-4), and the general formula (3-1) to the general formula (3). -4), R ¹¹ and R ¹² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{13 to} R ¹⁹ and R ^21. to R ²⁹ and ^R 31 ^{to R 39} and ^R 41 ^{to R 49} each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  More preferably, it is an aromatic amine compound represented by the general formula (5).

(In the formula, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{3 to} R ⁷ are each a hydrogen atom. Or an alkyl group having 1 to 4 carbon atoms or a phenyl group, and α represents any substituent represented by the general formula (5-1) to the general formula (5-4). In formulas (5-1) to (5-4), R ¹¹ and R ¹² are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms. R ^{13 to} R ¹⁹ and R ^{21 to} R ²⁹ and R ^{31 to} R ³⁹ and R ^{41 to} R ⁴⁹ each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  More preferably, it is an aromatic amine compound represented by the general formula (7).

(Wherein, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Α represents a general formula (7 -1) to any one of the substituents represented by the general formula (7-4), and in the general formula (7-1) to the general formula (7-4), R ¹¹ and R ¹² are each hydrogen. It represents either an atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{13 to} R ¹⁹ and R ^{21 to} R ²⁹ and R ^{31 to} R ³⁹ and R ^{41 to} R ^49. Each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  Moreover, it is preferable that it is an aromatic amine compound represented by General formula (9) or General formula (10).

(In the formula, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ¹¹ and R ¹² are each represented by: It represents either a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms.)

(Wherein R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ³⁰ represents a hydrogen atom or a carbon atom. Represents any one of the alkyl groups of formulas 1-4)

  Another aspect of the present invention is an aromatic amine compound represented by the general formula (2).

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and A ¹ has 6 to 25 carbon atoms. Ar ¹ represents an aryl group having 6 to 25 carbon atoms, and α represents any one of the substituents represented by the general formula (2-1) to the general formula (2-2). In general formulas (2-1) to (2-2), R ⁵¹ and R ⁵² are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl having 6 to 12 carbon atoms. Any one of the groups, and R ^{53 to} R ⁵⁸ and R ^{61 to} R ⁶⁸ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  Of the aromatic amine compounds represented by the general formula (2), an aromatic amine compound represented by the general formula (4) is preferable.

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and Ar ¹ represents 6 to 25 carbon atoms. Further, α represents a substituent represented by any one of the general formula (4-1) to the general formula (4-2), and the general formula (4-1) to the general formula (4). -2), R ⁵¹ and R ⁵² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{53 to} R ⁵⁸ and R ⁶¹ to R ⁶⁸ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  More preferably, it is an aromatic amine compound represented by the general formula (6).

(In the formula, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{3 to} R ⁷ are each a hydrogen atom. Or an alkyl group having 1 to 4 carbon atoms or a phenyl group, and α represents a substituent represented by any one of the general formula (6-1) to the general formula (6-2). In formulas (6-1) to (6-2), R ⁵¹ and R ⁵² are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms. R ^{53 to} R ⁵⁸ and R ^{61 to} R ⁶⁸ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  More preferably, it is an aromatic amine compound represented by the general formula (8).

(Wherein, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Α represents a general formula (8 -1) to any one of the substituents represented by the general formula (8-2), and in the general formula (8-1) to the general formula (8-2), R ⁵¹ and R ⁵² are each hydrogen. It represents either an atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{53 to} R ⁵⁸ and R ^{61 to} R ⁶⁸ are respectively a hydrogen atom or 1 to C carbon atoms. 4 represents an alkyl group.)

  Moreover, it is preferable that it is an aromatic amine compound represented by General formula (11) or General formula (12).

(In the formula, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ⁵¹ and R ⁵² are respectively It represents either a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms.)

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

  Another embodiment of the present invention is a light-emitting element having the above aromatic amine compound between a pair of electrodes.

  Another feature of the present invention is that a light emitting layer and a layer containing the aromatic amine compound are provided between a pair of electrodes, and the layer containing the aromatic amine compound is in contact with the light emitting layer. It is a light emitting element.

  Another embodiment of the present invention is a light-emitting element including a light-emitting layer and the above-described aromatic amine compound between a pair of electrodes, and the aromatic amine compound is included in the light-emitting layer. .

  In the above structure, the light-emitting layer includes a phosphorescent material that emits phosphorescence. In particular, when a phosphorescent material that emits green light is included, the effect of the present invention can be further obtained.

  In the above structure, the light-emitting layer includes a fluorescent material that emits fluorescence. In particular, when a fluorescent material that emits blue light is included, the effects of the present invention can be further obtained.

  In addition, a light-emitting device of the present invention includes a light-emitting element including the aromatic amine compound and a control unit that controls light emission of the light-emitting element. Note that a light-emitting device in this specification includes an image display device, a light-emitting device, or a light source (including a lighting device). In addition, a module in which a connector such as an FPC (Flexible Printed Circuit) or TAB (Tape Automated Bonding) tape or TCP (Tape Carrier Package) is attached to the panel, a TAB tape or a module having a printed wiring board at the end of TCP, Alternatively, a module in which an IC (integrated circuit) is directly mounted on a light emitting element by a COG (Chip On Glass) method is included in the light emitting device.

  An electronic device using the light-emitting element of the present invention for the display portion is also included in the category of the present invention. Therefore, an electronic device according to the present invention includes a display portion, and the display portion includes the above-described light emitting element and a control unit that controls light emission of the light emitting element.

  The aromatic amine compound of the present invention has a large band gap and can be used for a layer in contact with a light emitting material. Moreover, it can use as a material for disperse | distributing a luminescent material. By providing the aromatic amine compound of the present invention so as to be in contact with the light emitting material, movement of excitation energy of the light emitting material can be prevented, and light emission efficiency can be improved. Further, even when the aromatic amine compound of the present invention is excited, energy can be transferred from the aromatic amine compound of the present invention to the light emitting material, and the luminous efficiency can be improved.

  In addition, by using the aromatic amine compound of the present invention for a light-emitting element, a light-emitting device, or an electronic device, a light-emitting element, a light-emitting device, or an electronic device with high light emission efficiency can be obtained.

  Hereinafter, embodiments of the present invention will be described in detail with reference to the drawings. However, the present invention is not limited to the following description, and it is easily understood by those skilled in the art that modes and details can be variously changed without departing from the spirit and scope of the present invention. Therefore, the present invention should not be construed as being limited to the description of the embodiments below.

(Embodiment 1)
In this embodiment, the aromatic amine compound of the present invention will be described.

  The aromatic amine compound of the present invention is an aromatic amine compound represented by the general formula (1).

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and A ¹ has 6 to 25 carbon atoms. Ar ¹ represents an aryl group having 6 to 25 carbon atoms, and α represents any one of the substituents represented by the general formula (1-1) to the general formula (1-4). In the general formulas (1-1) to (1-4), R ¹¹ and R ¹² are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl having 6 to 12 carbon atoms. Any one of the groups, R ^{13 to} R ¹⁹ and R ^{21 to} R ²⁹ and R ^{31 to} R ³⁹ and R ^{41 to} R ⁴⁹ each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

In General Formula (1), R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, substituents represented by structural formulas (13-1) to (13-12) can be given.

In general formula (1), ^{A 1} represents an arylene group having 6 to 25 carbon atoms. Specifically, substituents represented by structural formulas (14-1) to (14-6) can be given.

In the general formula (1), Ar ¹ represents an aryl group having 6 to 25 carbon atoms. Specifically, substituents represented by structural formulas (15-1) to (15-6) can be given.

  Of the aromatic amine compounds represented by the general formula (1), an aromatic amine compound represented by the general formula (3) is preferable.

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and Ar ¹ represents 6 to 25 carbon atoms. In addition, α represents any one of the substituents represented by the general formula (3-1) to the general formula (3-4), and the general formula (3-1) to the general formula (3). -4), R ¹¹ and R ¹² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{13 to} R ¹⁹ and R ^21. to R ²⁹ and ^R 31 ^{to R 39} and ^R 41 ^{to R 49} each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  More preferably, it is an aromatic amine compound represented by the general formula (5).

(In the formula, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{3 to} R ⁷ are each a hydrogen atom. Or an alkyl group having 1 to 4 carbon atoms or a phenyl group, and α represents any substituent represented by the general formula (5-1) to the general formula (5-4). In formulas (5-1) to (5-4), R ¹¹ and R ¹² are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms. R ^{13 to} R ¹⁹ and R ^{21 to} R ²⁹ and R ^{31 to} R ³⁹ and R ^{41 to} R ⁴⁹ each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  More preferably, it is an aromatic amine compound represented by the general formula (7).

(Wherein, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Α represents a general formula (7 -1) to any one of the substituents represented by the general formula (7-4), and in the general formula (7-1) to the general formula (7-4), R ¹¹ and R ¹² are each hydrogen. It represents either an atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{13 to} R ¹⁹ and R ^{21 to} R ²⁹ and R ^{31 to} R ³⁹ and R ^{41 to} R ^49. Each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  Moreover, it is preferable that it is an aromatic amine compound represented by General formula (9) or General formula (10).

(In the formula, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ¹¹ and R ¹² are each represented by: It represents either a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms.)

(Wherein R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ³⁰ represents a hydrogen atom or a carbon atom. Represents any one of the alkyl groups of formulas 1-4)

  Moreover, the aromatic amine compound of this invention is an aromatic amine compound represented by General formula (2).

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and A ¹ has 6 to 25 carbon atoms. Ar ¹ represents an aryl group having 6 to 25 carbon atoms, and α represents any one of the substituents represented by the general formula (2-1) to the general formula (2-2). In general formulas (2-1) to (2-2), R ⁵¹ and R ⁵² are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl having 6 to 12 carbon atoms. Any one of the groups, and R ^{53 to} R ⁵⁸ and R ^{61 to} R ⁶⁸ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

In General Formula (2), R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, substituents represented by structural formulas (13-1) to (13-12) can be given.

In the general formula (2), A ¹ represents an arylene group having 6 to 25 carbon atoms. Specifically, substituents represented by structural formulas (14-1) to (14-6) can be given.

In General Formula (2), Ar ¹ represents an aryl group having 6 to 25 carbon atoms. Specifically, substituents represented by structural formulas (15-1) to (15-6) can be given.

  Of the aromatic amine compounds represented by the general formula (2), an aromatic amine compound represented by the general formula (4) is preferable.

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and Ar ¹ represents 6 to 25 carbon atoms. Further, α represents a substituent represented by any one of the general formula (4-1) to the general formula (4-2), and the general formula (4-1) to the general formula (4). -2), R ⁵¹ and R ⁵² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{53 to} R ⁵⁸ and R ⁶¹ to R ⁶⁸ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  More preferably, it is an aromatic amine compound represented by the general formula (6).

(In the formula, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ^{3 to} R ⁷ are each a hydrogen atom. Or an alkyl group having 1 to 4 carbon atoms or a phenyl group, and α represents a substituent represented by any one of the general formula (6-1) to the general formula (6-2). In formulas (6-1) to (6-2), R ⁵¹ and R ⁵² are each a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms. R ^{53 to} R ⁵⁸ and R ^{61 to} R ⁶⁸ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.)

  More preferably, it is an aromatic amine compound represented by the general formula (8).

(Wherein, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Α represents a general formula (8 -1) to any one of the substituents represented by the general formula (8-2), and in the general formula (8-1) to the general formula (8-2), R ⁵¹ and R ⁵² are each hydrogen. It represents either an atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{53 to} R ⁵⁸ and R ^{61 to} R ⁶⁸ are respectively a hydrogen atom or 1 to C carbon atoms. 4 represents an alkyl group.)

  Moreover, it is preferable that it is an aromatic amine compound represented by General formula (11) or General formula (12).

(In the formula, R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and R ⁵¹ and R ⁵² are respectively It represents either a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms.)

(In the formula, each of R ¹ and R ² represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms.)

  Specific examples of the aromatic amine compound of the present invention include aromatic amine compounds represented by structural formulas (21) to (119). However, the present invention is not limited to these.

  The aromatic amine compound of the present invention represented by the general formula (1) is synthesized by a synthesis method represented by a synthesis scheme (A-1) and a synthesis scheme (B-1) to a synthesis scheme (B-4). be able to.

First, a compound (compound B) containing N- (halogenated aryl) carbazole in a skeleton is prepared by reacting a compound (compound A) containing carbazole in the skeleton with a dihalide of an aromatic compound by a coupling reaction using a metal catalyst. ) And then a compound C is obtained by further conducting a coupling reaction with an arylamine using a metal catalyst such as palladium. In the synthesis scheme (A-1), the halogen element (X ¹ , X ² ) of the dihalide of the aromatic compound is preferably iodine or bromine. X ¹ and X ² may be the same or different. R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms. The aromatic compound is preferably a compound having 6 to 25 carbon atoms. The arylamine is preferably an arylamine having 6 to 25 carbon atoms.

  The aromatic amine compound of the present invention can be synthesized by reacting compound C with a halide of a fluorene derivative or a halide of a biphenyl derivative by a coupling reaction using a palladium catalyst or an Ullmann reaction using copper. .

In Synthesis Scheme (B-1) to Synthesis Scheme (B-4), X ^{1 to} X ⁴ each represent a halogen atom. R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and A ¹ is arylene having 6 to 25 carbon atoms. Represents a group, and Ar ¹ represents an aryl group having 6 to 25 carbon atoms. R ¹¹ and R ¹² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{13 to} R ¹⁹ and R ^{21 to} R ^29. R ^{31 to} R ³⁹ and R ^{41 to} R ⁴⁹ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

  In Synthesis Scheme (B-1) to Synthesis Scheme (B-4), in the compound represented by General Formula (1-1a), α in General Formula (1) described above is represented by General Formula (1-1). The compound represented by the general formula (1-2a) corresponds to the case where α in the general formula (1) is the general formula (1-2), and the general formula (1- The compound represented by 3a) corresponds to the case where α in the general formula (1) is the general formula (1-3), and the compound represented by the general formula (1-4a) This corresponds to the case where α in Formula (1) is General Formula (1-4).

  In the synthesis scheme (B-1), the halide of the fluorene derivative and the compound C are subjected to a coupling reaction using a palladium catalyst, or are coupled by an Ullmann reaction using copper, whereby the compound represented by the general formula (1) The compound represented by -1a) can be synthesized. The halogen element of the halide of the fluorene derivative is preferably iodine or bromine.

  Similarly, in the synthesis scheme (B-2) to the synthesis scheme (B-4), a biphenyl derivative halide and the compound C are subjected to a coupling reaction using a palladium catalyst, or an Ullmann reaction using copper. The compounds represented by the general formula (1-2a) to the general formula (1-4a) can be synthesized. The halogen element of the halide of the biphenyl derivative is preferably iodine or bromine.

  Moreover, the aromatic amine compound of this invention represented by General formula (2) is compoundable by the synthesis method represented by the synthesis scheme (B-5)-the synthesis scheme (B-6).

In Synthesis Scheme (B-5) to Synthesis Scheme (B-6), X ^{5 to} X ⁸ each represent a halogen atom. R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and A ¹ is arylene having 6 to 25 carbon atoms. Represents a group, and Ar ¹ represents an aryl group having 6 to 25 carbon atoms. R ⁵¹ and R ⁵² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and R ^{53 to} R ⁵⁸ and R ^{61 to} R ^68. Each represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

  In (B-5) to Synthesis scheme (B-6), in the compound represented by General Formula (2-1a), α in General Formula (2) described above is General Formula (2-1). Corresponding to the case, the compound represented by the general formula (2-2a) corresponds to the case where α in the general formula (2) is the general formula (2-2).

  In the synthesis scheme (B-5), a halide of a fluorene derivative and compound C are subjected to a coupling reaction using a palladium catalyst or by an Ullmann reaction using copper, whereby a compound represented by the general formula (2) The compound represented by -1a) can be synthesized. The halogen element of the halide of the fluorene derivative is preferably iodine or bromine.

  Similarly, in the synthesis scheme (B-6), a halide of a biphenyl derivative and compound C are subjected to a coupling reaction using a palladium catalyst or coupled by an Ullmann reaction using copper. A compound represented by the formula (2-2a) can be synthesized. The halogen element of the halide of the biphenyl derivative is preferably iodine or bromine.

  In addition, in the synthesis schemes (B-5) to (B-6), by reacting compound C with 2 equivalents of a halide, the aromatic amine compound of the present invention represented by the general formula (2) is converted into one step. It can be obtained by reaction.

In the above-described synthesis scheme, a coupling reaction using a palladium catalyst can use tri (tert-butyl) phosphine ((tert-Bu) ₃ P) as a ligand. As the Pd catalyst, bis (dibenzylideneacetone) palladium (0) (abbreviation: Pd (dba) ₂ ) and (tert-Bu) ₃ P are mixed to form (tert-Bu) ₃ P to bis (dibenzylidene). A catalyst coordinated to acetone) palladium (0) can be used. As a ligand in the case of using a palladium catalyst, it may be used _(tert-Bu) except ₃ P ligand. For example, DPPF can be used in addition to (tert-Bu) ₃ P. As the palladium catalyst, Pd (dba) ₂ , palladium diacetate (Pd (OAc) ₂ ) or the like can be used. Preferably, Pd (dba) ₂ is used. The reaction temperature is preferably from room temperature to 130 ° C. More preferably, the heating temperature is 60 to 110 ° C. In addition, dba shows trans, trans-dibenzylideneacetone. DPPF refers to 1,1-bis (diphenylphosphino) ferrocene. As the solvent, toluene, xylene, or the like can be used. As the base, an alkali metal alkoxide such as tert-BuONa, or a base such as potassium carbonate (K ₂ CO ₃ ) can be used.

  Since the aromatic amine compound of the present invention has a large band gap, it can be used as a host material for a light-emitting material that emits light of a short wavelength. Further, it can be used for a layer in contact with a light-emitting material which emits light with a short wavelength.

  More specifically, it is effective to use the aromatic amine compound of the present invention as a host material for a fluorescent material exhibiting short wavelength fluorescence such as blue. Moreover, it is effective to use for the layer which touches the layer containing the fluorescent material which shows fluorescence of a short wavelength. This is because the aromatic amine compound of the present invention has a high triplet level and singlet level, and thus energy transfer from the excited fluorescent material to the aromatic amine compound of the present invention is unlikely to occur. Therefore, the excitation energy of the fluorescent material can be extracted efficiently as light emission. Further, when the aromatic amine compound of the present invention is excited, it is possible to transfer energy from the triplet level or singlet level of the excited aromatic amine compound to the fluorescent material, and the light emission efficiency of the light emitting element Can be improved. When the aromatic amine compound of the present invention is used for a layer in contact with the layer containing the fluorescent material, it is more effective if the light emitting region is closer to the layer containing the aromatic amine compound of the present invention. It is. Moreover, if it is a fluorescent material which shows longer wavelength light emission, the same effect can be acquired by using the aromatic amine compound of this invention.

Specifically, it is effective to use the aromatic amine compound of the present invention as a host material for a phosphorescent material exhibiting phosphorescence of a relatively short wavelength such as green. In addition, it is effective to use for a layer in contact with a layer containing a phosphorescent material exhibiting phosphorescence with a relatively short wavelength. This is because the aromatic amine compound of the present invention has a high triplet level, so that energy transfer from an excited phosphorescent material to the aromatic amine compound of the present invention hardly occurs. Therefore, the excitation energy of the phosphorescent material can be efficiently extracted as light emission. In addition, when the aromatic amine compound of the present invention is excited, it is possible to transfer energy from the triplet level of the excited aromatic amine compound to the triplet level of the phosphorescent material, and the light emission efficiency of the light emitting element Can be improved. When the aromatic amine compound of the present invention is used for a layer in contact with the layer containing the phosphorescent material, it is more effective if the light emitting region is closer to the layer containing the aromatic amine compound of the present invention. It is. Moreover, if it is a phosphorescent material which shows light emission of a longer wavelength, the same effect can be acquired by using the aromatic amine compound of this invention.

  In particular, among the aromatic amine compounds of the present invention, the aromatic amine compound represented by the general formula (1) having an asymmetric structure is preferable because the band gap is larger. In addition, the triplet level is high, which is preferable.

  Moreover, the aromatic amine compound of the present invention is excellent in hole transportability. Therefore, it can be used as a hole transport layer of a light-emitting element, and a light-emitting element having favorable characteristics can be obtained.

  The aromatic amine compound represented by the general formula (2) is excellent in heat resistance. Therefore, a device having excellent heat resistance can be obtained by using the aromatic amine compound represented by the general formula (2).

(Embodiment 2)
One mode of a light-emitting element using the aromatic amine compound of the present invention is described below with reference to FIG.

  The light-emitting element of the present invention has a plurality of layers between a pair of electrodes. The plurality of layers have a high carrier injecting property and a high carrier transporting property so that a light emitting region is formed at a distance from the electrode, that is, a carrier is recombined at a position away from the electrode. It is a combination of layers of materials.

  In this embodiment, the light-emitting element includes a first electrode 102, a first layer 103, a second layer 104, a third layer 105, and a fourth layer 106 that are sequentially stacked over the first electrode 102. And a second electrode 107 provided thereon. Note that in this embodiment mode, the first electrode 102 functions as an anode and the second electrode 107 functions as a cathode.

  The substrate 101 is used as a support for the light emitting element. As the substrate 101, for example, glass or plastic can be used. Note that other materials may be used as long as the light-emitting element functions as a support in the manufacturing process.

  As the first electrode 102, a metal, an alloy, a conductive compound, a mixture thereof, or the like with a high work function (specifically, 4.0 eV or more) is preferably used. Specifically, for example, indium tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium zinc oxide (IZO), tungsten oxide, and oxide. Examples thereof include indium oxide containing zinc (IWZO). These conductive metal oxide films are usually formed by sputtering, but may be formed by applying a sol-gel method or the like. For example, indium oxide-zinc oxide (IZO) can be formed by a sputtering method using a target in which 1 to 20 wt% of zinc oxide is added to indium oxide. Indium oxide containing tungsten oxide and zinc oxide (IWZO) is formed by sputtering using a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide with respect to indium oxide. can do. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), or a nitride of a metal material (for example, titanium nitride: TiN).

The first layer 103 is a layer containing a substance having a high hole injection property. Molybdenum oxide (MoOx), vanadium oxide (VOx), ruthenium oxide (RuOx), tungsten oxide (WOx), manganese oxide (MnOx), or the like can be used. In addition, phthalocyanine compounds such as phthalocyanine (abbreviation: H ₂ Pc) and copper phthalocyanine (CuPC), or polymers such as poly (ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS) Also, the first layer 103 can be formed.

  For the first layer 103, a composite material formed by combining an organic compound and an inorganic compound can be used. In particular, in a composite material including an organic compound and an inorganic compound that exhibits an electron accepting property with respect to the organic compound, electrons are transferred between the organic compound and the inorganic compound, so that the carrier density increases. Excellent injection and hole transport properties.

In the case where a composite material formed by combining an organic compound and an inorganic compound is used as the first layer 103, the first electrode 102 can be in ohmic contact. The material for forming the electrode can be selected.

  The inorganic compound used for the composite material is preferably a transition metal oxide. In addition, oxides of metals belonging to Groups 4 to 8 in the periodic table can be given. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferable because of their high electron accepting properties. Among these, molybdenum oxide is especially preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.

As the organic compound used for the composite material, various compounds such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, and a high molecular compound (such as an oligomer, a dendrimer, and a polymer) can be used. Note that the organic compound used for the composite material is preferably an organic compound having a high hole-transport property. Specifically, a substance having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher is preferable. Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Below, the organic compound which can be used for a composite material is listed concretely.

  For example, as an aromatic amine compound, N, N′-di (p-tolyl) -N, N′-diphenyl-p-phenylenediamine (abbreviation: DTDPPA), 4,4′-bis [N- (4- Diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 4,4′-bis (N- {4- [N- (3-methylphenyl) -N-phenylamino] phenyl} -N-phenyl Amino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), and the like can be given.

  Specific examples of the carbazole derivative that can be used for the composite material include 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3 , 6-Bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1-naphthyl) -N- (9- Phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) and the like.

  In addition, 4,4′-di (N-carbazolyl) biphenyl (abbreviation: CBP), 1,3,5-tris [4- (N-carbazolyl) phenyl] benzene (abbreviation: TCPB), 9- [4- ( N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA), 1,4-bis [4- (N-carbazolyl) phenyl] -2,3,5,6-tetraphenylbenzene, and the like can be used. .

Examples of aromatic hydrocarbons that can be used for the composite material include 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 2-tert-butyl-9. , 10-di (1-naphthyl) anthracene, 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 2-tert-butyl-9,10-bis (4-phenylphenyl) anthracene ( Abbreviations: t-BuDBA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth), 2-tert-butylanthracene (abbreviation: t-BuAnth), 9,10-bis (4-methyl-1-naphthyl) anthracene (abbreviation: DMNA), 2-tert-butyl-9, 0-bis [2- (1-naphthyl) phenyl] anthracene, 9,10-bis [2- (1-naphthyl) phenyl] anthracene, 2,3,6,7-tetramethyl-9,10-di (1 -Naphthyl) anthracene, 2,3,6,7-tetramethyl-9,10-di (2-naphthyl) anthracene, 9,9'-bianthryl, 10,10'-diphenyl-9,9'-bianthryl, 10 , 10′-bis (2-phenylphenyl) -9,9′-bianthryl, 10,10′-bis [(2,3,4,5,6-pentaphenyl) phenyl] -9,9′-bianthryl, Anthracene, tetracene, rubrene, perylene, 2,5,8,11-tetra (tert-butyl) perylene and the like can be mentioned. In addition, pentacene, coronene, and the like can also be used. Thus, it is more preferable to use an aromatic hydrocarbon having a hole mobility of 1 × 10 ⁻⁶ cm ² / Vs or more and having 14 to 42 carbon atoms.

  Note that the aromatic hydrocarbon that can be used for the composite material may have a vinyl skeleton. As the aromatic hydrocarbon having a vinyl group, for example, 4,4′-bis (2,2-diphenylvinyl) biphenyl (abbreviation: DPVBi), 9,10-bis [4- (2,2- Diphenylvinyl) phenyl] anthracene (abbreviation: DPVPA) and the like.

  Alternatively, a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can be used.

  The second layer 104 is a layer that contains a substance having a high hole-transport property. Since the aromatic amine compound of the present invention described in Embodiment Mode 1 is excellent in hole transportability, it can be preferably used for the second layer 104. By using the aromatic amine compound of the present invention for the second layer 104, a light-emitting element with favorable characteristics can be obtained.

The third layer 105 is a layer containing a light-emitting substance. Various materials can be used for the light-emitting substance without any particular limitation. For example, fluorescent materials that emit fluorescence include coumarin derivatives such as coumarin 6 and coumarin 545T, quinacridone derivatives such as N, N′-dimethylquinacridone and N, N′-diphenylquinacridone, N-phenylacridone and N-methyl. Acridone derivatives such as acridone, 2-tert-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,10-diphenylanthracene (abbreviation: DPhA), rubrene, perifuranthene, 2, Condensed aromatic compounds such as 5,8,11-tetra (tert-butyl) perylene (abbreviation: TBP), 4-dicyanomethylene-2- [p- (dimethylamino) styryl] -6-methyl-4H-pyran, etc. Pyran derivatives of 4- (2,2-diphenylvinyl) triphenylamine, 9- 4- {N- [4- (carbazol-9-yl) phenyl] -N- phenylamino} phenyl) -10-phenylanthracene (abbreviation: YGAPA), and the like amine derivatives such. As a phosphorescent material that emits phosphorescence, tris (2-phenylpyridinato) iridium (III) (abbreviation: Ir (ppy) ₃ ), bis (2-phenylpyridinato) iridium (III) acetylacetonate (abbreviation) : Ir (ppy) ₂ (acac)), bis {2- (p-tolyl) pyridinato} iridium (III) acetylacetonate (abbreviation: Ir (tpy) ₂ (acac)), bis {2- (2'- Benzothienyl) pyridinato} iridium (III) acetylacetonate (abbreviation: Ir (btp) ₂ (acac)), bis {2- (4,6-difluorophenyl) pyridinato} iridium (III) picolinate (abbreviation: FIrpic), etc. Iridium complex of 2,3,7,8,12,13,17,18-octaethyl-21H, 23H- Porphyrin - platinum complexes, such as platinum complex (pt (OEP)), 4,7-diphenyl-1,10-phenanthroline tris (2-thenoyl trifluoro acetonate) and rare earth complexes such as europium (III).

  The present invention is effective when the light-emitting substance contained in the third layer 105 is a material that emits blue fluorescence. Specifically, it is preferable to use a fluorescent material that emits blue light, such as the above-described t-BuDNA, DPhA, TBP, and YGAPA.

Further, the present invention is effective when the light-emitting substance contained in the third layer 105 is a material that emits green phosphorescence. Specifically, a phosphorescent material that emits green light such as Ir (ppy) ₃ , Ir (ppy) ₂ (acac), or Ir (tpy) ₂ (acac) described above, or a phosphorescent material that emits blue-green light such as FIrpic. Preferably used

The third layer 105 may be formed by dispersing the light-emitting substance described above. Various materials can be used for dispersing the light-emitting substance, and it is preferable to use a substance having a higher LUMO level and a lower HOMO level than the light-emitting substance. Specifically, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB), tris (8-quinolinolato) aluminum (abbreviation: Alq), bis (2-methyl) -8-quinolinolato) (4-phenylphenolato) aluminum (abbreviation: BAlq), bis [2- (2-hydroxyphenyl) benzoxazolate] zinc (abbreviation: Zn (BOX) ₂ ), 2-tert-butyl -9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA), 2- (4- {N -[4- (Carbazol-9-yl) phenyl] -N-phenylamino} phenyl) -5-phenyl-1,3,4-oxadiazole (abbreviation: YGAO11) Or the like can be used. In addition, a plurality of materials for dispersing the light-emitting substance can be used. For example, a substance that suppresses crystallization, such as rubrene, may be further added to suppress crystallization. Further, NPB, Alq, or the like may be further added in order to more efficiently transfer energy to the light emitting substance.

For the fourth layer 106, a substance having a high electron-transport property can be used. For example, tris (8-quinolinolato) aluminum (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), Bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (abbreviation: BAlq), and the like, a layer made of a metal complex having a quinoline skeleton or a benzoquinoline skeleton. In addition, bis [2- (2-hydroxyphenyl) benzoxazolate] zinc (abbreviation: Zn (BOX) ₂ ), bis [2- (2-hydroxyphenyl) benzthiazolate] zinc (abbreviation: Zn (BTZ) ₂ ) and other metal complexes having an oxazole-based or thiazole-based ligand can also be used. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5 -(P-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-biphenylyl) -4-phenyl-5- (4- tert-Butylphenyl) -1,2,4-triazole (abbreviation: TAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and the like can also be used. The substances mentioned here are mainly substances having an electron mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that other than the above substances, any substance that has a property of transporting more electrons than holes may be used for the electron-transport layer. Further, the electron-transport layer is not limited to a single layer, and two or more layers including the above substances may be stacked.

  As a material for forming the second electrode 107, a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) can be used. Specific examples of such a cathode material include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg), calcium (Ca), Examples thereof include alkaline earth metals such as strontium (Sr), alloys containing these (MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these. However, by providing a layer having a function of promoting electron injection between the second electrode 107 and the fourth layer 106 so as to be stacked with the second electrode, Al can be obtained regardless of the work function. Various conductive materials such as Ag, ITO, and ITO containing silicon can be used for the second electrode 107.

As a layer having a function of promoting electron injection, an alkali metal or an alkaline earth metal such as lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), or a compound thereof is used. Can be used. For example, a layer made of a substance having an electron transporting property containing an alkali metal or an alkaline earth metal or a compound thereof, for example, a layer containing magnesium (Mg) in Alq can be used. Note that by using an electron injection layer containing an alkali metal or an alkaline earth metal in a layer made of a substance having an electron transporting property, electron injection from the second electrode 107 is efficiently performed. More preferred.

  Further, as a method for forming the first layer 103, the second layer 104, the third layer 105, and the fourth layer 106, various methods such as an ink jet method or a spin coat method are used in addition to a vapor deposition method. Can do. Moreover, you may form using the different film-forming method for each electrode or each layer.

  The light-emitting element of the present invention having the above structure is a third layer that contains a highly light-emitting substance because a current flows due to a potential difference generated between the first electrode 102 and the second electrode 107. In the layer 105, holes and electrons recombine to emit light. That is, a light emitting region is formed in the third layer 105.

  Light emission is extracted outside through one or both of the first electrode 102 and the second electrode 107. Therefore, one or both of the first electrode 102 and the second electrode 107 is formed using a light-transmitting substance. In the case where only the first electrode 102 is formed using a light-transmitting substance, light emission is extracted from the substrate side through the first electrode 102 as illustrated in FIG. In the case where only the second electrode 107 is formed using a light-transmitting substance, light emission is extracted from the side opposite to the substrate through the second electrode 107 as illustrated in FIG. In the case where both the first electrode 102 and the second electrode 107 are made of a light-transmitting substance, light is emitted from the first electrode 102 and the second electrode 107 as shown in FIG. And is taken out from both the substrate side and the opposite side of the substrate.

  Note that the structure of the layers provided between the first electrode 102 and the second electrode 107 is not limited to the above. A structure in which a light emitting region in which holes and electrons are recombined is provided in a portion away from the first electrode 102 and the second electrode 107 so that quenching caused by the proximity of the light emitting region and the metal is suppressed. Anything other than the above may be used.

In other words, the layered structure of the layers is not particularly limited, and a substance having a high electron transporting property or a substance having a high hole transporting property, a substance having a high electron injecting property, a substance having a high hole injecting property, or a bipolar property (electron and hole) The layer made of a substance having a high transportability), a hole blocking material and the like may be freely combined with the aromatic amine compound of the present invention.

  A light-emitting element shown in FIG. 2 includes a first layer 303 made of a substance having a high electron-transport property, a second layer 304 containing a light-emitting substance, a hole-transport property, and the first electrode 302 functioning as a cathode. A third layer 305 made of a high substance, a fourth layer 306 made of a substance having a high hole-injecting property, and a second electrode 307 functioning as an anode are sequentially stacked. Reference numeral 301 denotes a substrate.

  In this embodiment mode, a light-emitting element is manufactured over a substrate made of glass, plastic, or the like. A passive light-emitting device can be manufactured by manufacturing a plurality of such light-emitting elements over one substrate. Alternatively, for example, a thin film transistor (TFT) may be formed over a substrate made of glass, plastic, or the like, and a light-emitting element may be formed over an electrode electrically connected to the TFT. Thus, an active matrix light-emitting device in which driving of the light-emitting element is controlled by the TFT can be manufactured. Note that the structure of the TFT is not particularly limited. A staggered TFT or an inverted staggered TFT may be used. Further, there is no particular limitation on the crystallinity of the semiconductor used for the TFT, and an amorphous semiconductor or a crystalline semiconductor may be used. Further, the driving circuit formed on the TFT substrate may be composed of N-type and P-type TFTs, or may be composed of only one of N-type and P-type.

  Since the aromatic amine compound of the present invention has a large band gap, a light-emitting element having favorable characteristics can be obtained by application to the light-emitting element.

  The aromatic amine compound of the present invention is effective for use in a layer in contact with a layer containing a fluorescent material exhibiting short wavelength fluorescence. This is because the aromatic amine compound of the present invention has a high triplet level and singlet level, and thus energy transfer from the excited fluorescent material to the aromatic amine compound of the present invention is unlikely to occur. Therefore, the excitation energy of the fluorescent material can be extracted efficiently as light emission. Further, when the aromatic amine compound of the present invention is excited, it is possible to transfer energy from the triplet level or singlet level of the excited aromatic amine compound to the fluorescent material, and the light emission efficiency of the light emitting element Can be improved. When the aromatic amine compound of the present invention is used for a layer in contact with the layer containing the fluorescent material, it is more effective if the light emitting region is closer to the layer containing the aromatic amine compound of the present invention. It is. Moreover, if it is a fluorescent material which shows longer wavelength light emission, the same effect can be acquired by using the aromatic amine compound of this invention.

In addition, the aromatic amine compound of the present invention is effective for use in a layer in contact with a layer containing a phosphorescent material exhibiting a relatively short wavelength phosphorescence. This is because the aromatic amine compound of the present invention has a high triplet level, so that energy transfer from an excited phosphorescent material to the aromatic amine compound of the present invention hardly occurs. Therefore, the excitation energy of the phosphorescent material can be efficiently extracted as light emission. In addition, when the aromatic amine compound of the present invention is excited, it is possible to transfer energy from the triplet level of the excited aromatic amine compound to the triplet level of the phosphorescent material, and the light emission efficiency of the light emitting element Can be improved. When the aromatic amine compound of the present invention is used for a layer in contact with the layer containing the phosphorescent material, it is more effective if the light emitting region is closer to the layer containing the aromatic amine compound of the present invention. It is. Moreover, if it is a phosphorescent material which shows light emission of a longer wavelength, the same effect can be acquired by using the aromatic amine compound of this invention.

  In particular, among the aromatic amine compounds of the present invention, the aromatic amine compound represented by the general formula (1) having an asymmetric structure is preferable because the band gap is larger. In addition, the triplet level is high, which is preferable.

  Further, since the light-emitting element of the present invention has high light emission efficiency, power consumption can be reduced.

  Moreover, the aromatic amine compound of the present invention is excellent in hole transportability. Therefore, it can be used as a hole transport layer of a light-emitting element, and a light-emitting element having favorable characteristics can be obtained.

  The aromatic amine compound represented by the general formula (2) is excellent in heat resistance. Therefore, a device having excellent heat resistance can be obtained by using the aromatic amine compound represented by the general formula (2).

(Embodiment 3)
In this embodiment, a light-emitting element having a structure different from that described in Embodiment 2 will be described.

  Since the aromatic amine compound of the present invention has a large band gap and a high triplet level and singlet level, it can be used as a host for dispersing a light-emitting material. That is, it can be used for the third layer 105 described in Embodiment Mode 2. As the luminescent substance dispersed in the aromatic amine compound of the present invention, various fluorescent materials and phosphorescent materials can be used.

In the case where the aromatic amine compound of the present invention is used for the third layer 105, various materials can be used as a substance for forming the second layer 104. For example, various aromatic amine compounds can be used. As a widely used material, 4,4′-bis [N- (3-methylphenyl) -N-phenylamino] biphenyl and its derivative 4,4′-bis [N- (1-naphthyl)- N-phenylamino] biphenyl (hereinafter referred to as NPB), 4,4 ′, 4 ″ -tris (N, N-diphenyl-amino) triphenylamine, 4,4 ′, 4 ″ -tris [N— And starburst aromatic amine compounds such as (3-methylphenyl) -N-phenylamino] triphenylamine. The substances described here are mainly substances having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Note that the second layer 104 is not limited to a single layer, and may be a mixed layer of the above substances or a stack of two or more layers.

  Since the aromatic amine compound of the present invention has a large band gap, it can be used as a host material for a light-emitting material that emits light of a short wavelength.

  The aromatic amine compound of the present invention is effectively used as a host material for a fluorescent material exhibiting short wavelength fluorescence such as blue. This is because the aromatic amine compound of the present invention has a high triplet level and singlet level, and thus energy transfer from the excited fluorescent material to the aromatic amine compound of the present invention is unlikely to occur. Therefore, the excitation energy of the fluorescent material can be extracted efficiently as light emission. Further, when the aromatic amine compound of the present invention is excited, it is possible to transfer energy from the triplet level or singlet level of the excited aromatic amine compound to the fluorescent material, and the light emission efficiency of the light emitting element Can be improved. Moreover, if it is a fluorescent material which shows longer wavelength light emission, the same effect can be acquired by using the aromatic amine compound of this invention.

In addition, the aromatic amine compound of the present invention is effectively used as a host material for phosphorescent materials that exhibit phosphorescence of a relatively short wavelength such as green. This is because the aromatic amine compound of the present invention has a high triplet level, so that energy transfer from an excited phosphorescent material to the aromatic amine compound of the present invention hardly occurs. Therefore, the excitation energy of the phosphorescent material can be efficiently extracted as light emission. In addition, when the aromatic amine compound of the present invention is excited, it is possible to transfer energy from the triplet level of the excited aromatic amine compound to the triplet level of the phosphorescent material, and the light emission efficiency of the light emitting element Can be improved. Moreover, if it is a phosphorescent material which shows light emission of a longer wavelength, the same effect can be acquired by using the aromatic amine compound of this invention.

  In particular, among the aromatic amine compounds of the present invention, the aromatic amine compound represented by the general formula (1) having an asymmetric structure is preferable because the band gap is larger. In addition, the triplet level is high, which is preferable.

  Further, since the light-emitting element of the present invention has high light emission efficiency, power consumption can be reduced.

  The aromatic amine compound represented by the general formula (2) is excellent in heat resistance. Therefore, a device having excellent heat resistance can be obtained by using the aromatic amine compound represented by the general formula (2).

(Embodiment 4)
In this embodiment, a light-emitting element having a structure different from the structures shown in Embodiments 2 to 3 will be described.

  By using the aromatic amine compound of the present invention for the third layer 105 shown in Embodiment Mode 2, light emission from the aromatic amine compound of the present invention can be obtained. Since the aromatic amine compound of the present invention exhibits purple to blue light emission, a light emitting element exhibiting purple to blue light emission can be obtained.

  The third layer 105 may be composed of only the aromatic amine compound of the present invention, or may be composed of the aromatic amine compound of the present invention dispersed in another substance. As the substance for dispersing the aromatic amine compound of the present invention, various materials can be used. In addition to the substance having a high hole transport and the substance having a high electron transport property described in Embodiment 2, 3- (4 -Biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole (abbreviation: TAZ), 4,4'-di (N-carbazolyl) biphenyl (abbreviation: CBP), 2,2 ′, 2 ″-(1,3,5-benzenetri-yl) -tris [1-phenyl-1H-benzimidazole] (abbreviation: TPBI), and the like.

  Since the aromatic amine compound of the present invention has a high glass transition point, a light-emitting element having excellent heat resistance can be obtained by using it in a light-emitting element.

  Moreover, the aromatic amine compound of the present invention is stable even when the oxidation reaction and the subsequent reduction reaction are repeated. That is, it is stable to repeated oxidation reactions. Therefore, a long-life light-emitting element can be obtained by using the aromatic amine compound of the present invention for a light-emitting element.

Note that the structures described in Embodiments 2 to 3 can be used as appropriate, except for the third layer 105.
(Embodiment 5)
In this embodiment, a light-emitting element having a structure different from the structures shown in Embodiments 2 to 4 will be described.

  Since the aromatic amine compound of the present invention has a hole injecting property, it can be used for the first layer 103 described in Embodiment Mode 2. In addition, a composite material in which the aromatic amine compound of the present invention and an inorganic compound are combined can be used for the first layer 103. The inorganic compound used for the composite material is preferably a transition metal oxide. In addition, oxides of metals belonging to Groups 4 to 8 in the periodic table can be given. Specifically, vanadium oxide, niobium oxide, tantalum oxide, chromium oxide, molybdenum oxide, tungsten oxide, manganese oxide, and rhenium oxide are preferable because of their high electron accepting properties. Among these, molybdenum oxide is especially preferable because it is stable in the air, has a low hygroscopic property, and is easy to handle.

  The composite material formed by combining the aromatic amine compound and the inorganic compound of the present invention transfers electrons between the organic compound and the inorganic compound, and increases the carrier density. Excellent transportability. In addition, when a composite material formed by combining the aromatic amine compound of the present invention and an inorganic compound is used as the first layer 103, it is possible to make ohmic contact with the first electrode 102, so that the work function is Regardless, the material for forming the first electrode can be selected.

When the aromatic amine compound of the present invention is used for the first layer 103, various materials can be used as a substance for forming the second layer 104. For example, a compound of an aromatic amine (that is, a compound having a benzene ring-nitrogen bond) can be used. As a widely used material, 4,4′-bis [N- (3-methylphenyl) -N-phenylamino] biphenyl and its derivative 4,4′-bis [N- (1-naphthyl)- N-phenylamino] biphenyl (hereinafter referred to as NPB), 4,4 ′, 4 ″ -tris (N, N-diphenyl-amino) triphenylamine, 4,4 ′, 4 ″ -tris [N— And starburst aromatic amine compounds such as (3-methylphenyl) -N-phenylamino] triphenylamine. The substances described here are mainly substances having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Note that the second layer 104 is not limited to a single layer, and may be a mixed layer of the above substances or a stack of two or more layers.

  In addition, the aromatic amine compound of the present invention may be used as the first layer 103 and the second layer 104.

  Since the aromatic amine compound of the present invention has a hole injection property, it can be used as a hole injection layer of a light emitting element.

  In addition, since the aromatic amine compound of the present invention has a high glass transition point, a light-emitting element having excellent heat resistance can be obtained by using it for a light-emitting element.

  Moreover, the aromatic amine compound of the present invention is stable even when the oxidation reaction and the subsequent reduction reaction are repeated. That is, it is stable to repeated oxidation reactions. Therefore, a long-life light-emitting element can be obtained by using the aromatic amine compound of the present invention for a light-emitting element.

  Note that the structures described in Embodiments 2 to 4 can be used as appropriate, except for the first layer 103.

(Embodiment 6)
In this embodiment, a mode of a light-emitting element having a structure in which a plurality of light-emitting units according to the present invention is stacked (hereinafter referred to as a stacked element) will be described with reference to FIG. This light-emitting element is a light-emitting element having a plurality of light-emitting units between a first electrode and a second electrode. As the light-emitting unit, a structure similar to that of the layer containing a light-emitting substance described in Embodiment 2 can be used. That is, the light-emitting element described in Embodiment 2 is a light-emitting element having one light-emitting unit, and in this embodiment, a light-emitting element having a plurality of light-emitting units will be described.

In FIG. 9, a first light emitting unit 511 and a second light emitting unit 512 are stacked between a first electrode 501 and a second electrode 502. The first electrode 501 and the second electrode 502 can be the same as those in Embodiment 2. In addition, the first light-emitting unit 511 and the second light-emitting unit 512 may have the same configuration or different configurations, and the configurations are the same as those in Embodiments 2 to 5. Can do.

The charge generation layer 513 includes a composite material of an organic compound and a metal oxide. This composite material of an organic compound and a metal oxide includes the organic compound described in Embodiment 2 and a metal oxide such as vanadium oxide, molybdenum oxide, or tungsten oxide. As the organic compound, various compounds such as an aromatic amine compound, a carbazole derivative, an aromatic hydrocarbon, and a high molecular compound (oligomer, dendrimer, polymer, etc.) can be used. As the organic compound, it is preferable to use a hole transporting organic compound having a hole mobility of 10 ⁻⁶ cm ² / Vs or more. Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Since a composite of an organic compound and a metal oxide is excellent in carrier injecting property and carrier transporting property, low voltage driving and low current driving can be realized.

Note that the charge generation layer 513 may be formed by combining a composite of an organic compound and a metal oxide with another material. For example, a layer including a composite of an organic compound and a metal oxide may be combined with a layer including one compound selected from electron donating substances and a compound having a high electron transporting property. Alternatively, a layer including a composite of an organic compound and a metal oxide may be combined with a transparent conductive film.

In any case, the charge generation layer 513 sandwiched between the first light-emitting unit 511 and the second light-emitting unit 512 is formed on one side when a voltage is applied to the first electrode 501 and the second electrode 502. Any device that injects electrons into the light emitting unit and injects holes into the other light emitting unit may be used.

  Although the light-emitting element having two light-emitting units has been described in this embodiment mode, the present invention can be similarly applied to a light-emitting element in which three or more light-emitting units are stacked. Like the light-emitting element according to the present embodiment, a plurality of light-emitting units are partitioned and arranged between a pair of electrodes by a charge generation layer, so that a long-life element in a high-luminance region can be obtained while maintaining a low current density. realizable. Further, when illumination is used as an application example, the voltage drop due to the resistance of the electrode material can be reduced, so that uniform light emission over a large area is possible. In addition, a light-emitting device that can be driven at a low voltage and has low power consumption can be realized.

  Note that this embodiment can be combined with any of the other embodiments as appropriate.

(Embodiment 7)
In this embodiment mode, a light-emitting device manufactured using the aromatic amine compound of the present invention will be described.

  In this embodiment mode, a light-emitting device manufactured using the aromatic amine compound of the present invention will be described with reference to FIGS. 3A is a top view illustrating the light-emitting device, and FIG. 3B is a cross-sectional view taken along lines A-A ′ and B-B ′ in FIG. 3A. This light-emitting device controls light emission of the light-emitting element. Reference numeral 601 indicated by a dotted line includes a driver circuit portion (source side driver circuit), 602 a pixel portion, and 603 a driver circuit portion (gate side driver circuit). It is out. Reference numeral 604 denotes a sealing substrate, reference numeral 605 denotes a sealing material, and the inside surrounded by the sealing material 605 is a space 607.

  Note that the routing wiring 608 is a wiring for transmitting a signal input to the source side driving circuit 601 and the gate side driving circuit 603, and a video signal, a clock signal, an FPC (flexible printed circuit) 609 serving as an external input terminal, Receives start signal, reset signal, etc. Although only the FPC is shown here, a printed wiring board (PWB) may be attached to the FPC. The light-emitting device in this specification includes not only a light-emitting device body but also a state in which an FPC or a PWB is attached thereto.

  Next, a cross-sectional structure will be described with reference to FIG. A driver circuit portion and a pixel portion are formed over the element substrate 610. Here, a source-side driver circuit 601 that is a driver circuit portion and one pixel in the pixel portion 602 are illustrated.

  Note that the source side driver circuit 601 is a CMOS circuit in which an n-channel TFT 623 and a p-channel TFT 624 are combined. The drive circuit may be formed of various CMOS circuits, PMOS circuits, or NMOS circuits. In this embodiment mode, a driver integrated type in which a driver circuit is formed over a substrate is shown; however, this is not necessarily required, and the driver circuit can be formed outside the substrate.

  The pixel portion 602 is formed by a plurality of pixels including a switching TFT 611, a current control TFT 612, and a first electrode 613 electrically connected to the drain thereof. Note that an insulator 614 is formed so as to cover an end portion of the first electrode 613. Here, a positive photosensitive acrylic resin film is used.

  In order to improve the coverage, a curved surface having a curvature is formed at the upper end or the lower end of the insulator 614. For example, when positive photosensitive acrylic is used as a material for the insulator 614, it is preferable that only the upper end portion of the insulator 614 has a curved surface with a curvature radius (0.2 μm to 3 μm). As the insulator 614, either a negative type that becomes insoluble in an etchant by light irradiation or a positive type that becomes soluble in an etchant by light irradiation can be used.

  Over the first electrode 613, a layer 616 containing a light-emitting substance and a second electrode 617 are formed. Here, as a material used for the first electrode 613 functioning as an anode, a material having a high work function is preferably used. For example, an ITO film or an indium tin oxide film containing silicon, an indium oxide film containing 2 to 20 wt% zinc oxide, a titanium nitride film, a chromium film, a tungsten film, a Zn film, a Pt film, or the like In addition, a stack of titanium nitride and a film containing aluminum as a main component, a three-layer structure including a titanium nitride film, a film containing aluminum as a main component, and a titanium nitride film can be used. Note that with a stacked structure, resistance as a wiring is low, good ohmic contact can be obtained, and a function as an anode can be obtained.

  The layer 616 containing a light-emitting substance is formed by various methods such as an evaporation method using an evaporation mask, an inkjet method, and a spin coating method. The layer 616 containing a light-emitting substance contains the aromatic amine compound of the present invention described in Embodiment Mode 1. Further, as another material constituting the layer 616 containing a light-emitting substance, a low molecular compound or a high molecular compound (including an oligomer and a dendrimer) may be used.

Further, as a material used for the second electrode 617 which is formed over the light-emitting substance-containing layer 616 and functions as a cathode, a material having a low work function (Al, Mg, Li, Ca, or an alloy or compound thereof such as MgAg, MgIn, AlLi, LiF, or is preferably used CaF _2, etc.). Note that in the case where light generated in the layer 616 containing a light-emitting substance passes through the second electrode 617, the second electrode 617 includes a thin metal film and a transparent conductive film (ITO, 2 to 20 wt. % Of indium oxide containing zinc oxide, indium tin oxide containing silicon, zinc oxide (ZnO), or the like is preferably used.

  Further, the sealing substrate 604 is bonded to the element substrate 610 with the sealant 605, whereby the light-emitting element 618 is provided in the space 607 surrounded by the element substrate 610, the sealing substrate 604, and the sealant 605. Yes. Note that the space 607 is filled with a filler, and may be filled with a sealant 605 in addition to an inert gas (such as nitrogen or argon).

  Note that an epoxy-based resin is preferably used for the sealant 605. Moreover, it is desirable that these materials are materials that do not transmit moisture and oxygen as much as possible. In addition to a glass substrate or a quartz substrate, a plastic substrate made of FRP (Fiberglass-Reinforced Plastics), PVF (polyvinyl fluoride), polyester, acrylic, or the like can be used as a material used for the sealing substrate 604.

  As described above, a light-emitting device manufactured using the aromatic amine compound of the present invention can be obtained.

  Since the aromatic amine compound described in Embodiment Mode 1 is used for the light-emitting device of the present invention, a light-emitting device having favorable characteristics can be obtained. Specifically, a light-emitting device with high light emission efficiency can be obtained.

  The aromatic amine compound represented by the general formula (2) is excellent in heat resistance. Therefore, a light emitting device having excellent heat resistance can be obtained by using the aromatic amine compound represented by the general formula (2).

  As described above, in this embodiment mode, an active light-emitting device that controls driving of a light-emitting element using a transistor has been described. In addition to this, a light-emitting element is driven without particularly providing a driving element such as a transistor. A passive light emitting device may be used. FIG. 4 is a perspective view of a passive light emitting device manufactured by applying the present invention. In FIG. 4, a layer 955 containing a light-emitting substance is provided between the electrode 952 and the electrode 956 over the substrate 951. An end portion of the electrode 952 is covered with an insulating layer 953. A partition layer 954 is provided over the insulating layer 953. The side wall of the partition wall layer 954 has an inclination such that the distance between one side wall and the other side wall becomes narrower as it approaches the substrate surface. That is, the cross section in the short side direction of the partition wall layer 954 has a trapezoidal shape, and the bottom side (the side facing the insulating layer 953 in the same direction as the surface direction of the insulating layer 953) is the top side (the surface of the insulating layer 953). The direction is the same as the direction and is shorter than the side not in contact with the insulating layer 953. In this manner, by providing the partition layer 954, defects in the light-emitting element due to static electricity or the like can be prevented. Further, even in a passive light emitting device, a light emitting device with high light emission efficiency can be obtained by including the light emitting element of the present invention with high light emission efficiency. In addition, a light emitting device having excellent heat resistance can be obtained. In addition, since the light emission efficiency is high, power consumption can be reduced.

(Embodiment 8)
In this embodiment mode, electronic devices of the present invention which include the light-emitting device described in Embodiment Mode 7 as a part thereof will be described. An electronic device of the present invention includes the aromatic amine compound of the present invention described in Embodiment Mode 1 and has a display portion with high heat resistance. In addition, the display portion has high emission efficiency. Further, since the luminous efficiency is high, there is an effect that power consumption can be reduced.

  As an electronic device having a light-emitting element manufactured using the aromatic amine compound of the present invention, a camera such as a video camera or a digital camera, a goggle type display, a navigation system, a sound reproduction device (car audio, audio component, etc.), a computer , A game device, a portable information terminal (mobile computer, mobile phone, portable game machine, electronic book, etc.), and an image playback device (specifically, Digital Versatile Disc (DVD)) provided with a recording medium. , A device provided with a display device capable of displaying the image). Specific examples of these electronic devices are shown in FIGS.

  FIG. 5A illustrates a television device according to the present invention, which includes a housing 9101, a supporting base 9102, a display portion 9103, a speaker portion 9104, a video input terminal 9105, and the like. In this television device, the display portion 9103 is formed by arranging light-emitting elements similar to those described in Embodiment Modes 2 to 6 in a matrix. The light-emitting element has a feature of high luminous efficiency. Moreover, it has the characteristic that heat resistance is high. Since the display portion 9103 including the light-emitting elements has similar features, this television set has little deterioration in image quality and low power consumption. With such a feature, the deterioration compensation function circuit and the power supply circuit can be significantly reduced or reduced in the television device; therefore, the housing 9101 and the support base 9102 can be reduced in size and weight. In the television device according to the present invention, low power consumption, high image quality, and reduction in size and weight are achieved, so that a product suitable for a living environment can be provided.

  FIG. 5B illustrates a computer according to the present invention, which includes a main body 9201, a housing 9202, a display portion 9203, a keyboard 9204, an external connection port 9205, a pointing device 9206, and the like. In this computer, the display portion 9203 includes light-emitting elements similar to those described in Embodiment Modes 2 to 6, arranged in a matrix. The light-emitting element has a feature of high luminous efficiency. Moreover, it has the characteristic that heat resistance is high. The display portion 9203 which includes the light-emitting elements has similar features. Therefore, in this computer, image quality is hardly deteriorated and low power consumption is achieved. With such a feature, deterioration compensation functional circuits and power supply circuits can be significantly reduced or reduced in the computer, so that the main body 9201 and the housing 9202 can be reduced in size and weight. In the computer according to the present invention, low power consumption, high image quality, and reduction in size and weight are achieved; therefore, a product suitable for the environment can be provided.

  FIG. 5C illustrates a cellular phone according to the present invention, which includes a main body 9401, a housing 9402, a display portion 9403, an audio input portion 9404, an audio output portion 9405, operation keys 9406, an external connection port 9407, an antenna 9408, and the like. . In this cellular phone, the display portion 9403 is formed by arranging light-emitting elements similar to those described in Embodiment Modes 2 to 6 in a matrix. The light-emitting element has a feature of high luminous efficiency. Moreover, it has the characteristic that heat resistance is high. Since the display portion 9403 including the light-emitting elements has similar features, the cellular phone has little deterioration in image quality and low power consumption. With such a feature, the deterioration compensation functional circuit and the power supply circuit can be significantly reduced or reduced in the mobile phone, so that the main body 9401 and the housing 9402 can be reduced in size and weight. Since the cellular phone according to the present invention has low power consumption, high image quality, and reduced size and weight, a product suitable for carrying can be provided.

  FIG. 5D illustrates a camera according to the present invention, which includes a main body 9501, a display portion 9502, a housing 9503, an external connection port 9504, a remote control receiving portion 9505, an image receiving portion 9506, a battery 9507, an audio input portion 9508, and operation keys 9509. , An eyepiece 9510 and the like. In this camera, the display portion 9502 includes light-emitting elements similar to those described in Embodiment Modes 2 to 6, arranged in a matrix. The light-emitting element has a feature of high luminous efficiency. Moreover, it has the characteristic that heat resistance is high. Since the display portion 9502 including the light-emitting elements has similar features, this camera has little deterioration in image quality and low power consumption. With such a feature, the deterioration compensation function circuit and the power supply circuit can be significantly reduced or reduced in the camera, so that the main body 9501 can be reduced in size and weight. Since the camera according to the present invention has low power consumption, high image quality, and small size and light weight, a product suitable for carrying can be provided.

  As described above, the applicable range of the light-emitting device of the present invention is so wide that the light-emitting device can be applied to electronic devices in various fields. By using the aromatic amine compound of the present invention, an electronic device having a display portion with high light emission efficiency and high heat resistance can be provided.

  The light-emitting device of the present invention can also be used as a lighting device. One mode in which the light-emitting element of the present invention is used as a lighting device will be described with reference to FIGS.

  FIG. 6 illustrates an example of a liquid crystal display device using the light-emitting device of the present invention as a backlight. The liquid crystal display device illustrated in FIG. 6 includes a housing 901, a liquid crystal layer 902, a backlight 903, and a housing 904, and the liquid crystal layer 902 is connected to a driver IC 905. The backlight 903 uses the light-emitting device of the present invention, and a current is supplied from a terminal 906.

  By using the light emitting device of the present invention as a backlight of a liquid crystal display device, a backlight having high luminous efficiency can be obtained. Further, the light-emitting device of the present invention is a surface-emitting illumination device and can have a large area, so that the backlight can have a large area and a liquid crystal display device can have a large area. Further, since the light-emitting device of the present invention is thin and has low power consumption, the display device can be thinned and the power consumption can be reduced. In addition, since the light emitting device of the present invention is excellent in heat resistance, a liquid crystal display device using the light emitting device of the present invention is also excellent in heat resistance.

  FIG. 7 illustrates an example in which the light-emitting device to which the present invention is applied is used as a table lamp which is a lighting device. A table lamp illustrated in FIG. 7 includes a housing 2001 and a light source 2002, and the light-emitting device of the present invention is used as the light source 2002. Since the light-emitting device of the present invention can emit light with high luminance, the hand can be brightly illuminated when performing fine work.

  FIG. 8 illustrates an example in which the light-emitting device to which the present invention is applied is used as an indoor lighting device 3001. Since the light-emitting device of the present invention can have a large area, it can be used as a large-area lighting device. In addition, since the light-emitting device of the present invention is thin and has low power consumption, it can be used as a lighting device with low thickness and low power consumption. In this manner, in the room where the light-emitting device to which the present invention is applied is used as an indoor lighting device 3001, the television set 3002 according to the present invention as described with reference to FIG. Can be appreciated. In such a case, since both devices have low power consumption, powerful images can be viewed in a bright room without worrying about electricity charges.

In this example, N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2-amine (abbreviation: YGAF) represented by the structural formula (21) The synthesis method will be described.

[Step 1]
A method for synthesizing 9- [4- (N-phenylamino) phenyl] carbazole (abbreviation: YGA) will be described.

(I) Synthesis of N- (4-bromophenyl) carbazole A synthesis scheme (C-1) of N- (4-bromophenyl) carbazole is shown below.

  First, a method for synthesizing N- (4-bromophenyl) carbazole will be described. In a 300 mL three-necked flask, 56.3 g (0.24 mol) of 1,4-dibromobenzene, 31.3 g (0.18 mol) of carbazole, 4.6 g (0.024 mol) of copper iodide, 66 of potassium carbonate .3 g (0.48 mol), 2.1 g (0.008 mol) of 18-crown-6-ether was added, and the atmosphere was replaced with nitrogen, and 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -Pyrimidinone (abbreviation: DMPU) 8mL was added and it stirred at 180 degreeC for 6 hours. The reaction mixture was cooled to room temperature, the precipitate was removed by suction filtration, and the filtrate was washed with diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine in that order, and dried over magnesium sulfate. After drying, the reaction mixture is naturally filtered, the filtrate is concentrated, and the resulting oily substance is purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to give a solid obtained by chloroform, hexane. As a result, 20.7 g of a light brown plate-like crystal of the target product N- (4-bromophenyl) carbazole was obtained in a yield of 35%. This compound was confirmed to be N- (4-bromophenyl) carbazole by nuclear magnetic resonance (NMR).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ = 8.14 (d, J = 7.8 Hz, 2H), δ = 7.73 (d, J = 8.7 Hz, 2H), δ = 7.46 ( d, J = 8.4 Hz, 2H), δ = 7.42-7.26 (m, 6H).

(Ii) Synthesis of 9- [4- (N-phenylamino) phenyl] carbazole (abbreviation: YGA) A synthesis scheme (C-2) of YGA is shown below.

  In a 200 mL three-necked flask, 5.4 g (17.0 mmol) of N- (4-bromophenyl) carbazole obtained in (i) above, 1.8 mL (20.0 mmol) of aniline, bis (dibenzylideneacetone) palladium 100 mg (0.17 mmol) of (0) and 3.9 g (40 mmol) of sodium tert-butoxide were added, and the atmosphere was replaced with nitrogen, and 0.1 mL of tri (tert-butyl) phosphine (10 wt% hexane solution) and 50 mL of toluene were added. And stirred at 80 ° C. for 6 hours. The reaction mixture was filtered through Florisil, celite, and alumina, and the filtrate was washed with water and saturated brine, and dried over magnesium sulfate. The reaction mixture was naturally filtered, and the oil obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1) to obtain the desired product, 9- [4- (N-phenyl). Amino) phenyl] carbazole (abbreviation: YGA) (4.1 g, yield 73%) was obtained. This compound was confirmed to be 9- [4- (N-phenylamino) phenyl] carbazole (abbreviation: YGA) by nuclear magnetic resonance (NMR).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 8.47 (s, 1H), δ = 8.22 (d, J = 7.8 Hz, 2H), δ = 7.44-7.16 ( m, 14H), [delta] = 6.92-6.87 (m, 1H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 10B is a chart in which the range of 6.7 ppm to 8.6 ppm in FIG.

[Step 2]
A method for synthesizing N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2-amine (abbreviation: YGAF) represented by the structural formula (21) is described. To do. The synthesis scheme is shown in (D-1).

  2-Bromo-9,9-dimethylfluorene 2.9 g (10 mmol), 4- (carbazol-9-yl) diphenylamine 3.34 g (10 mmol), bis (dibenzylideneacetone) palladium (0) 115 mg (0.2 mmol) Put 300 g (31.2 mmol) of tert-butoxy sodium into a 300 mL three-necked flask and purge with nitrogen, add 100 mL of toluene and 0.2 mL of tri (tert-butyl) phosphine (10 wt% hexane solution), and stir at 80 ° C. for 5 hours. did. After the reaction, the reaction solution was filtered through Celite, Florisil, and alumina, the filtrate was washed with water, and the aqueous layer was extracted with toluene. The extracted solution and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate. The solid obtained by naturally filtering the reaction mixture and concentrating the filtrate was purified by silica gel column chromatography (hexane: toluene = 7: 3). As a result, 3.6 g of the desired white solid was obtained in a yield of 64%. I got it. N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2 represented by the structural formula (21) by nuclear magnetic resonance (NMR). -It confirmed that it was an amine (abbreviation: YGAF).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 1.40 (s, 6H), 7.09-7.53 (m, 20H), 7.75-7.77 (m, 1H), 7 .81 (d, J = 8.4 Hz, 1H), 8.23 (d, J = 7.5 Hz, 2H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 11B is a chart in which the range of 6.0 ppm to 9.0 ppm in FIG.

  When 635 mg of the obtained YGAF was purified by sublimation at 200 Pa, 230 ° C. for 12 hours while flowing argon gas at 20.0 mL / min, 485 mg of a pale yellow solid of YGAF was obtained, and the recovery rate was 76%. .

  In addition, it was 313 degreeC when the decomposition temperature (Td) of YGAF was measured with the differential thermothermal weight simultaneous measuring apparatus (The Seiko Electronics Co., Ltd. make, TG / DTA320 type | mold).

Moreover, the glass transition point was measured using the differential scanning calorimeter (DSC, the Perkin Elmer company make, Pyris1). First, the sample was heated to 300 ° C. at 40 ° C./min, and then cooled to room temperature at 40 ° C./min. Thereafter, the temperature was raised to 300 ° C. at 10 ° C./min,
The DSC chart of FIG. 12 was obtained by cooling to room temperature at a temperature of ° C / min. In FIG. 12, the X axis shows temperature and the Y axis shows heat flow. On the Y axis, the upward direction indicates endotherm. From this chart, it was found that the glass transition point (Tg) of YGAF was 91 ° C.

  Moreover, the absorption spectrum of the toluene solution of YGAF is shown in FIG. Further, FIG. 14 shows an absorption spectrum of a thin film of YGAF. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. Samples were prepared by depositing the solution in a quartz cell and depositing the thin film on a quartz substrate. The absorption spectra obtained by subtracting the absorption spectrum of quartz are shown in FIGS. 13 and 14, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed near 326 to 362 nm, and in the case of the thin film, absorption was observed near 343 nm. Further, FIG. 15 shows an emission spectrum of a YGAF toluene solution (excitation wavelength: 340 nm). Further, FIG. 16 shows an emission spectrum of a YGAF thin film (excitation wavelength: 343 nm). 15 and 16, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 384 nm (excitation wavelength 340 nm) in the case of the toluene solution, and 396 nm (excitation wavelength 343 nm) in the case of the thin film.

  The HOMO level of YGAF in the thin film state was −5.39 eV as a result of measurement by atmospheric photoelectron spectroscopy (AC-2, manufactured by Riken Keiki Co., Ltd.). Furthermore, using the data of the absorption spectrum of the YGAF thin film in FIG. 14, the absorption edge was obtained from Tauc plot, and the absorption edge was estimated as the optical energy gap. The energy gap was 3.25 eV. Therefore, the LUMO level is −2.14 eV.

  Moreover, the oxidation reaction characteristic of YGAF was measured. The oxidation reaction characteristics were examined by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A) was used.

As a solution in CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (supporting electrolyte) ( n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the measurement target is further dissolved to a concentration of 1 mmol / L. did. In addition, as a working electrode, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode), and as an auxiliary electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)), and Ag / Ag ⁺ electrode (manufactured by BAS Co., Ltd., RE5 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature.

  The oxidation reaction characteristics of YGAF were examined as follows. A scan in which the potential of the working electrode with respect to the reference electrode was changed from −0.12 V to 0.8 V and then changed from 0.8 V to −0.12 V was taken as one cycle, and 100 cycles were measured. The scan speed for CV measurement was set to 0.1 V / s.

  The results of examining the oxidation reaction characteristics of YGAF are shown in FIG. In FIG. 17, the horizontal axis represents the potential (V) of the working electrode with respect to the reference electrode, and the vertical axis represents the current value (μA) flowing between the working electrode and the auxiliary electrode.

From FIG. 17, a current indicating oxidation was observed around 0.62 V (vs. Ag ^/ Ag ⁺ electrode). In addition, in spite of repeating 100 cycles of scanning, the oxidation reaction shows almost no change in the peak position or peak intensity of the CV curve. From this, it was found that the aromatic amine compound of the present invention is extremely stable with respect to oxidation reaction and subsequent reduction reaction (that is, repeated oxidation).

  Moreover, the optimal molecular structure in the ground state of YGAF was calculated by B3LYP / 6-311 (d, p) of density functional theory (DFT). DFT is used in this calculation because it has better calculation accuracy than the Hartree-Fock (HF) method, which does not take into account electronic correlation, and the calculation cost is lower than the perturbation method (MP) method, which is the same level of calculation accuracy. did. The calculation was performed using a high performance computer (HPC) (manufactured by SGI, Altix 3700 DX).

In addition, the triplet excitation energy (energy gap) of YGAF was calculated by applying B3LYP / 6-311 (d, p) of time-dependent density functional theory (TDDFT) in the molecular structure optimized by DFT. However, the triplet excitation energy was calculated to be 2.70 eV. Therefore, it was found from the calculation results that the aromatic amine compound of the present invention has high triplet excitation energy.

In this example, a method for synthesizing 4- (carbazol-9-yl) phenyl-4'-phenyltriphenylamine (abbreviation: YGA1BP) represented by the structural formula (52) will be described. The synthesis scheme is shown in (D-2).

2.Bromobiphenyl 2.33 g (10 mmol), 4- (carbazol-9-yl) diphenylamine 3.30 g (10 mmol), bis (dibenzylideneacetone) palladium (0) 56 mg (0.1 mmol) tert-butoxy sodium 0 g (31.2 mmol) was placed in a 300 mL three-necked flask and purged with nitrogen. Toluene 20 mL and tri (tert-butyl) phosphine (10 wt% hexane solution) 0.1 mL were added, and the mixture was stirred at 80 ° C. for 5 hours. After the reaction, the reaction solution was filtered through Celite, Florisil, and alumina, the filtrate was washed with water, and the aqueous layer was extracted with toluene. The extracted solution and the organic layer were combined, washed with saturated brine, and dried over magnesium sulfate. The reaction mixture was naturally filtered, and the solid obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane: toluene = 7: 3), and the resulting solid was recrystallized from toluene and hexane. The powdery white solid of 4.2 g was obtained with a yield of 86%. It was confirmed by nuclear magnetic resonance (NMR) that this compound was 4- (carbazol-9-yl) phenyl-4′-phenyltriphenylamine (abbreviation: YGA1BP) represented by the structural formula (52). .

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 7.12-7.47 (m, 18H), 7.53 (d, J = 8.7 Hz, 2H), 7.68-7.64 ( m, 4H), 8.23 (d, J = 7.8 Hz, 2H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 18B is a chart in which the range of 6.0 ppm to 9.0 ppm in FIG.

  When 694 mg of the obtained YGA1BP was purified by sublimation at 200 Pa, 280 ° C. for 5 hours while flowing argon gas at 20.0 mL / min, 544 mg of YGA1BP colorless solid was obtained, and the recovery rate was 78%.

Further, thermogravimetry-differential thermal analysis (TG-DTA) of YGA1BP was performed using a high vacuum differential type differential thermal balance (DTA 2410SA, manufactured by Bruker AXS Co., Ltd.). When measured at a rate of temperature increase of 10 ° C./min under normal pressure, the temperature at which the weight becomes 95% or less of the weight at the start of measurement was 398 ° C. from the relationship between the weight and temperature (thermogravimetry). It was.

  Further, FIG. 19 shows an absorption spectrum of a toluene solution of YGA1BP. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The solution was put in a quartz cell, and an absorption spectrum obtained by subtracting the absorption spectrum of quartz is shown in FIG. In FIG. 19, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 324 nm. Further, FIG. 20 shows an emission spectrum of a YGA1BP toluene solution (excitation wavelength: 340 nm). In FIG. 20, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, the maximum emission wavelength was 387 nm (excitation wavelength: 340 nm).

  Moreover, the optimal molecular structure in the ground state of YGA1BP was calculated by B3LYP / 6-311 (d, p) of density functional theory (DFT). DFT is used in this calculation because it has better calculation accuracy than the Hartree-Fock (HF) method, which does not take into account electronic correlation, and the calculation cost is lower than the perturbation method (MP) method, which is the same level of calculation accuracy. did. The calculation was performed using a high performance computer (HPC) (manufactured by SGI, Altix 3700 DX).

In addition, the triplet excitation energy (energy gap) of YGA1BP was calculated by applying B3LYP / 6-311 (d, p) of time-dependent density functional theory (TDDFT) in the molecular structure optimized by DFT. However, the triplet excitation energy was calculated to be 2.87 eV. Therefore, it was found from the calculation results that the aromatic amine compound of the present invention has high triplet excitation energy.

In this example, N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-diphenyl-9,9-dimethylfluorene-2,7 represented by the structural formula (71) -The synthesis | combining method of diamine (abbreviation: YGA2F) is demonstrated. The synthesis scheme is shown in (D-3).

  2,7-diiodo-9,9-dimethylfluorene 1.7 g (3.8 mmol), 4- (carbazol-9-yl) diphenylamine 2.5 g (7.6 mmol), bis (dibenzylideneacetone) palladium (0) 44 mg (0.2 mmol) and tert-butoxy sodium 2.0 g (20 mmol) were placed in a 300 mL three-necked flask and purged with nitrogen. Toluene 30 mL and tri (tert-butyl) phosphine (10 wt% hexane solution) 0.1 mL were added, Stir at 12 ° C. for 12 hours. After the reaction, the reaction solution was filtered through Celite, Florisil, and alumina, the filtrate was washed with water, and the aqueous layer was extracted with toluene. The extracted solution and the organic layer were combined and washed with saturated brine, and then the organic layer was dried over magnesium sulfate. The reaction mixture was naturally filtered, and the solid obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane: toluene = 6: 4). The obtained compound was recrystallized from toluene and hexane to obtain 2.9 g of the objective light yellow powdered solid in 89% yield. N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-diphenyl-9,9 represented by the structural formula (71) by nuclear magnetic resonance (NMR). -It was confirmed that it was dimethylfluorene-2,7-diamine (abbreviation: YGA2F).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 1.37 (s, 6H), 7.06-7.51 (m, 34H), 7.76 (d, J = 8.4 Hz, 2H) 8.22 (d, J = 7.8 Hz, 4H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 21B is a chart in which the range of 6.0 ppm to 9.0 ppm in FIG.

  When 670 mg of the obtained YGA2F was purified by sublimation under conditions of 200 Pa and 420 ° C. while flowing argon gas at 3.0 mL / min for 15 hours, 511 g of a light yellow solid of YGA2F was obtained, and the recovery rate was 76%. there were.

    In addition, when the decomposition temperature (Td) of YGA2F was measured with a differential thermothermal gravimetric simultaneous measurement device (Seiko Electronics Co., Ltd., TG / DTA320 type), it was found to be 500 ° C. or higher, and YGA2F showed high Td. .

  Moreover, the glass transition point was measured using the differential scanning calorimeter (DSC, the Perkin Elmer company make, Pyris1). First, the sample was heated to 400 ° C. at 40 ° C./min, and then cooled to room temperature at 40 ° C./min. Thereafter, the temperature was raised to 400 ° C. at 10 ° C./min and cooled to room temperature at 10 ° C./min to obtain the DSC chart of FIG. In FIG. 22, temperature is shown on the X axis and heat flow is shown on the Y axis. On the Y axis, the upward direction indicates endotherm. From this chart, it was found that the glass transition point (Tg) of YGA2F was 150 ° C. Therefore, it turned out that the aromatic amine compound of this invention is excellent in heat resistance.

  Moreover, the absorption spectrum of the toluene solution of YGA2F is shown in FIG. Moreover, the absorption spectrum of the thin film of YGA2F is shown in FIG. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. Samples were prepared by depositing the solution in a quartz cell and depositing the thin film on a quartz substrate. The absorption spectra obtained by subtracting the absorption spectrum of quartz are shown in FIGS. 23 and 24, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed near 327 nm and 377 nm, and in the case of the thin film, absorption was observed near 383 nm. An emission spectrum of a YGA2F toluene solution (excitation wavelength: 340 nm) is shown in FIG. In addition, an emission spectrum of a thin film of YGA2F (excitation wavelength: 383 nm) is shown in FIG. 25 and 26, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, peaks of emission spectrum were observed at 400 nm and 422 nm (excitation wavelength: 340 nm), and in the case of the thin film, peaks at 410 nm, 430 nm, and 537 nm (excitation wavelength: 383 nm).

  The HOMO level of YGA2F in the thin film state was −5.27 eV as a result of measurement by atmospheric photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-2). Furthermore, using the data of the absorption spectrum of the YGA2F thin film in FIG. 24, the absorption edge was obtained from the Tauc plot, and the absorption edge was estimated as the optical energy gap. The energy gap was 3.05 eV. Therefore, the LUMO level is −2.22 eV.

  Moreover, the oxidation reaction characteristic of YGA2F was measured. The oxidation reaction characteristics were examined by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A) was used.

As a solution in CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (supporting electrolyte) ( n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the measurement target is further dissolved to a concentration of 1 mmol / L. did. In addition, as a working electrode, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode), and as an auxiliary electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)), and Ag / Ag ⁺ electrode (manufactured by BAS Co., Ltd., RE5 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature.

  The oxidation reaction characteristics of YGA2F were examined as follows. A scan in which the potential of the working electrode with respect to the reference electrode was changed from −0.31 V to 1.0 V and then changed from 1.0 V to −0.31 V was taken as one cycle, and 100 cycles were measured. The scan speed for CV measurement was set to 0.1 V / s.

  The result of examining the oxidation reaction characteristic of YGA2F is shown in FIG. In FIG. 27, the horizontal axis represents the potential (V) of the working electrode with respect to the reference electrode, and the vertical axis represents the current value (μA) flowing between the working electrode and the auxiliary electrode.

From FIG. 27, a current indicating oxidation was observed around 0.40 V (vs. Ag ^/ Ag ⁺ electrode). In addition, in spite of repeating 100 cycles of scanning, the oxidation reaction shows almost no change in the peak position or peak intensity of the CV curve. From this, it was found that the aromatic amine compound of the present invention is extremely stable with respect to oxidation reaction and subsequent reduction reaction (that is, repeated oxidation).

In this example, N, N′-bis (4- (carbazol-9-yl) phenyl) -N, N′-diphenylbiphenyl-4,4′-diamine represented by the structural formula (102) (abbreviation: The synthesis method of (YGABP) will be described. The synthesis scheme is shown in (D-4).

  4,4′-diiodo-1,1′-biphenyl 2.0 g (5.0 mmol), 4- (carbazol-9-yl) diphenylamine 3.3 g (10.0 mmol), bis (dibenzylideneacetone) palladium (0 ) 65 mg (0.1 mmol) and 2.0 g (21.0 mmol) of tert-butoxy sodium were placed in a 200 mL three-necked flask and purged with nitrogen, followed by 50 mL of toluene, tri (tert-butyl) phosphine (10 wt% hexane solution) 0 0.1 mL was added and stirred at 80 ° C. for 6 hours. The reaction solution was cooled to room temperature, filtered through celite, Florisil and alumina, and the filtrate was washed with water and saturated brine. The mixture was naturally filtered to remove magnesium sulfate, and the white solid obtained by concentrating the filtrate was recrystallized from chloroform and hexane. As a result, 1.8 g of the target white powdery solid was obtained with a yield of 45%. Got in. This compound is represented by the structural formula (102) by N, N′-bis (4- (carbazol-9-yl) phenyl) -N, N′-diphenylbiphenyl-4,4′-diamine (abbreviation: YGABP). It was confirmed that.

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, DMSO-d ₆ ): δ = 7.12-7.17 (m, 2H), 7.20-7.30 (m, 16H), 7.38-7.47 (m, 12H), 7.52 (d, J = 8.7 Hz, 4H), 7.67 (d, J = 9.0 Hz, 4H), 8.22 (d, J = 7.8 Hz, 4H). ¹ H NMR charts are shown in FIGS. Note that FIG. 28B is a chart in which the range of 6.0 ppm to 9.0 ppm in FIG.

  When 1.8 g of the obtained YGABP was purified by sublimation under conditions of 7.8 Pa and 300 ° C. while flowing argon gas at 3.0 mL / min for 15 hours, 1.6 g of YGABP pale yellow solid was obtained and recovered. The rate was 89%.

  Moreover, when the decomposition temperature (Td) of YGABP was measured with a differential thermothermal gravimetric simultaneous measurement apparatus (Seiko Denshi Co., Ltd., TG / DTA320 type), it was found to be 500 ° C. or higher, and YGABP showed high Td. .

  Moreover, the glass transition point was measured using the differential scanning calorimeter (DSC, the Perkin Elmer company make, Pyris1). First, the sample was heated to 350 ° C. at 40 ° C./min, and then cooled to room temperature at 40 ° C./min. Thereafter, the temperature was raised to 350 ° C. at 10 ° C./min and cooled to room temperature at 10 ° C./min, whereby the DSC chart of FIG. 29 was obtained. In FIG. 29, the temperature is shown on the X axis and the heat flow is shown on the Y axis. On the Y axis, the upward direction indicates endotherm. From this chart, it was found that the glass transition point (Tg) of YGABP was 144 ° C. Therefore, it turned out that the aromatic amine compound of this invention is excellent in heat resistance.

  Further, FIG. 30 shows an absorption spectrum of a toluene solution of YGABP. Further, FIG. 31 shows an absorption spectrum of a thin film of YGABP. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. Samples were prepared by depositing the solution in a quartz cell and depositing the thin film on a quartz substrate. The absorption spectra obtained by subtracting the absorption spectrum of quartz are shown in FIG. 30 and FIG. 30 and 31, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed near 328 nm and 346 nm, and in the case of the thin film, absorption was observed near 349 nm. An emission spectrum of a YGABP toluene solution (excitation wavelength: 350 nm) is shown in FIG. Further, FIG. 33 shows an emission spectrum of a YGABP thin film (excitation wavelength: 350 nm). 32 and 33, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). The maximum emission wavelength was 400 nm (excitation wavelength 350 nm) in the case of the toluene solution, and 410 nm (excitation wavelength 350 nm) in the case of the thin film.

  The HOMO level of YGABP in a thin film state was −5.41 eV as a result of measurement by atmospheric photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-2). Furthermore, using the data of the absorption spectrum of the YGABP thin film in FIG. 31, the absorption edge was obtained from the Tauc plot, and the absorption edge was estimated as the optical energy gap. The energy gap was 3.13 eV. Therefore, the LUMO level is −2.28 eV.

  Moreover, the oxidation reaction characteristic of YGABP was measured. The oxidation reaction characteristics were examined by cyclic voltammetry (CV) measurement. For the measurement, an electrochemical analyzer (manufactured by BAS Co., Ltd., model number: ALS model 600A) was used.

As a solution in CV measurement, dehydrated dimethylformamide (DMF) (manufactured by Aldrich, 99.8%, catalog number: 22705-6) was used as a solvent, and tetra-n-butylammonium perchlorate (supporting electrolyte) ( n-Bu ₄ NClO ₄ ) (manufactured by Tokyo Chemical Industry Co., Ltd., catalog number: T0836) is dissolved to a concentration of 100 mmol / L, and the measurement target is further dissolved to a concentration of 1 mmol / L. did. In addition, as a working electrode, a platinum electrode (manufactured by BAS Co., Ltd., PTE platinum electrode), and as an auxiliary electrode, a platinum electrode (manufactured by BAS Inc., Pt counter electrode for VC-3 ( 5 cm)), and Ag / Ag ⁺ electrode (manufactured by BAS Co., Ltd., RE5 non-aqueous solvent system reference electrode) was used as a reference electrode. The measurement was performed at room temperature.

  The oxidation reaction characteristics of YGABP were examined as follows. A scan in which the potential of the working electrode with respect to the reference electrode was changed from −0.2 V to 1.0 V and then changed from 1.0 V to −0.2 V was set to one cycle, and 100 cycles were measured. The scan speed for CV measurement was set to 0.1 V / s.

  The results of examining the oxidation reaction characteristics of YGABP are shown in FIG. In FIG. 34, the horizontal axis represents the potential (V) of the working electrode with respect to the reference electrode, and the vertical axis represents the current value (μA) flowing between the working electrode and the auxiliary electrode.

From FIG. 34, a current indicating oxidation was observed around 0.66 V (vs. Ag ^/ Ag ⁺ electrode). In addition, in spite of repeating 100 cycles of scanning, the oxidation reaction shows almost no change in the peak position or peak intensity of the CV curve. From this, it was found that the aromatic amine compound of the present invention is extremely stable with respect to oxidation reaction and subsequent reduction reaction (that is, repeated oxidation).

  In this example, a light-emitting element of the present invention will be described with reference to FIG. The chemical formula of the material used in this example is shown below.

(Light emitting element 1)
First, indium tin oxide containing silicon oxide was formed over a glass substrate 2101 by a sputtering method, so that a first electrode 2102 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm.

Next, the substrate on which the first electrode is formed is fixed to a substrate holder provided in the vacuum evaporation apparatus so that the surface on which the first electrode is formed is downward, and the pressure is reduced to about 10 ⁻⁴ Pa. After that, NPB and molybdenum oxide (VI) were co-evaporated on the first electrode 2102 to form a layer 2103 including a composite material formed by combining an organic compound and an inorganic compound. The film thickness was 50 nm, and the weight ratio of NPB and molybdenum oxide (VI) was adjusted to 4: 1 (= NPB: molybdenum oxide). Note that the co-evaporation method is an evaporation method in which evaporation is performed simultaneously from a plurality of evaporation sources in one processing chamber.

  Next, N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9 represented by the structural formula (21) is formed on the layer 2103 containing the composite material by an evaporation method using resistance heating. 9-dimethylfluorenyl-2-amine (abbreviation: YGAF) was formed to a thickness of 10 nm, whereby a hole-transport layer 2104 was formed.

  Further, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) and 9- (4- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino } Phenyl) -10-phenylanthracene (abbreviation: YGAPA) was co-evaporated to form a light-emitting layer 2105 having a thickness of 30 nm on the hole-transport layer 2104. Here, the weight ratio of CzPA to YGAPA was adjusted to be 1: 0.04 (= CzPA: YGAPA).

  Then, tris (8-quinolinolato) aluminum (abbreviation: Alq) was formed to a thickness of 10 nm over the light-emitting layer 2105 by an evaporation method using resistance heating, so that an electron-transport layer 2106 was formed.

  Further, an electron injection layer 2107 having a thickness of 20 nm was formed on the electron transport layer 2106 by co-evaporation of Alq and lithium. Here, the weight ratio of Alq to lithium was adjusted to be 1: 0.01 (= Alq: lithium).

  Finally, a light-emitting element 1 was manufactured by forming a second electrode 2108 by depositing aluminum on the electron injection layer 2107 so as to have a thickness of 200 nm by using a resistance heating vapor deposition method. .

(Light emitting element 2)
As the hole-transport layer 2104, N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-diphenyl-9,9-dimethylfluorene-2 represented by the structural formula (71) , 7-diamine (abbreviation: YGA2F) was formed to a thickness of 10 nm. Except for the hole transport layer, the light-emitting element 1 was formed.

(Light emitting element 3)
As the hole-transporting layer 2104, N, N′-bis (4- (carbazol-9-yl) phenyl) -N, N′-diphenylbiphenyl-4,4′-diamine represented by the structural formula (102) ( (Abbreviation: YGABP) was formed to a thickness of 10 nm. Except for the hole transport layer, the light-emitting element 1 was formed.

(Comparative light emitting element 4)
As the hole transport layer 2104, NPB was formed to a thickness of 10 nm. Except for the hole transport layer, the light-emitting element 1 was formed.

  FIG. 36 shows current density-luminance characteristics of the light-emitting elements 1 to 3 and the comparative light-emitting element 4. In addition, FIG. 37 shows voltage-luminance characteristics. In addition, FIG. 38 shows luminance-current efficiency characteristics. As can be seen from FIG. 38, the light-emitting element using the aromatic amine compound of the present invention exhibits high current efficiency. In addition, from FIG. 37, the light-emitting element of the present invention can reduce a voltage necessary for obtaining a certain luminance. That is, the drive voltage can be reduced. Thus, power consumption of the light emitting element can be reduced.

  Thus, by using the aromatic amine compound of the present invention and the hole transport layer, a light-emitting element having favorable characteristics can be obtained.

  In this example, a light-emitting element of the present invention will be described with reference to FIG. The chemical formula of the material used in this example is shown below.

(Light emitting element 5)
First, indium tin oxide containing silicon oxide was formed over a glass substrate 2101 by a sputtering method, so that a first electrode 2102 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm.

Next, the substrate on which the first electrode is formed is fixed to a substrate holder provided in the vacuum evaporation apparatus so that the surface on which the first electrode is formed is downward, and the pressure is reduced to about 10 ⁻⁴ Pa. After that, NPB and molybdenum oxide (VI) were co-evaporated on the first electrode 2102 to form a layer 2103 including a composite material formed by combining an organic compound and an inorganic compound. The film thickness was 50 nm, and the weight ratio of NPB and molybdenum oxide (VI) was adjusted to 4: 1 (= NPB: molybdenum oxide). Note that the co-evaporation method is an evaporation method in which evaporation is performed simultaneously from a plurality of evaporation sources in one processing chamber.

  Next, N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9 represented by the structural formula (21) is formed on the layer 2103 containing the composite material by an evaporation method using resistance heating. 9-dimethylfluorenyl-2-amine (abbreviation: YGAF) was formed to a thickness of 10 nm, whereby a hole-transport layer 2104 was formed.

Furthermore, 2- (4- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} phenyl) -5-phenyl-1,3,4-oxadiazole (abbreviation: YGAO11) and A light emitting layer having a thickness of 30 nm is formed on the hole transport layer 2104 by co-evaporation of bis (2-phenylpyridinato) iridium (III) acetylacetonate (abbreviation: Ir (ppy) ₂ (acac)). 2105 was formed. Here, the weight ratio between YGAO11 and Ir _(ppy) 2 (acac) is 1: 0.05: was adjusted to (= YGAO11 _Ir (ppy) 2 (acac)).

  Thereafter, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (abbreviation: BAlq) is formed to a thickness of 10 nm over the light-emitting layer 2105 by a resistance heating vapor deposition method. Then, an electron transport layer 2106 was formed.

  Further, an electron injection layer 2107 having a thickness of 20 nm was formed on the electron transport layer 2106 by co-evaporation of Alq and lithium. Here, the weight ratio of Alq to lithium was adjusted to be 1: 0.01 (= Alq: lithium).

  Finally, a light emitting element 5 was manufactured by forming a second electrode 2108 by depositing aluminum on the electron injection layer 2107 so as to have a thickness of 200 nm using a resistance heating vapor deposition method. .

(Comparative light emitting element 6)
As the hole transport layer 2104, NPB was formed to a thickness of 10 nm. The layers other than the hole transport layer were formed in the same manner as the light emitting element 5.

  39 shows current density-luminance characteristics of the light-emitting element 5 and the comparative light-emitting element 6. In FIG. Further, FIG. 40 shows voltage-luminance characteristics. In addition, FIG. 41 shows luminance-current efficiency characteristics. As can be seen from FIG. 41, the light-emitting element using the aromatic amine compound of the present invention exhibits high current efficiency. In addition, it can be seen from FIG. 40 that the light-emitting element of the present invention exhibits substantially the same drive voltage as that of the comparative light-emitting element 6.

  Further, the triplet excitation energy (energy gap) of YGAF and YGA1BP, which are the aromatic amine compounds of the present invention, and NPB used in the comparative light-emitting element 6 was calculated. As a calculation method, the optimal molecular structure in the ground state was calculated by B3LYP / 6-311 (d, p) of density functional theory (DFT). DFT is used in this calculation because it has better calculation accuracy than the Hartree-Fock (HF) method, which does not take into account electronic correlation, and the calculation cost is lower than the perturbation method (MP) method, which is the same level of calculation accuracy. did. The calculation was performed using a high performance computer (HPC) (manufactured by SGI, Altix 3700 DX). Subsequently, the triplet excitation energy (energy gap) of these compounds is obtained by applying the time-dependent density functional theory (TDDFT) B3LYP / 6-311 (d, p) in the molecular structure optimized by DFT. Calculated. The corresponding wavelength was calculated from the triplet excitation energy (energy gap). The results are shown in Table 1 and FIG.

  As can be seen from Table 1 and FIG. 42, it can be seen that YGAF and YGA1BP, which are aromatic amine compounds of the present invention, have higher triplet excitation energy than NPB used in comparative light-emitting element 6. In particular, it can be seen that YGA1BP has a high triplet excitation energy. The wavelength corresponding to the triplet excitation energy of the aromatic amine compound of the present invention is around 450 nm, which corresponds to blue. The wavelength corresponding to the triplet excitation energy of NPB used in comparative light-emitting element 6 is 500 nm, which corresponds to green. Therefore, when NPB is used for the layer in contact with the green phosphorescent material, there is a possibility that energy is transferred to the NPB even when the green phosphorescent material is excited. Therefore, light emission from the phosphorescent material does not occur and the light emission efficiency is lowered. On the other hand, when the aromatic amine compound of the present invention is used in a layer in contact with a phosphorescent material that emits green phosphorescence, energy transfer does not occur from the excited green phosphorescent material to the aromatic amine compound of the present invention. . In addition, when the aromatic amine compound of the present invention is excited, energy can be transferred to the green phosphorescent material. Therefore, high luminous efficiency can be realized.

  The singlet excitation energy is higher than the triplet excitation energy. For this reason, not only phosphorescent materials but also fluorescent materials have the same effect. Specifically, since the wavelength corresponding to the triplet excitation energy of the aromatic amine compound of the present invention corresponds to blue, the wavelength corresponding to the singlet excitation energy is shorter than blue. Therefore, when an aromatic amine compound is used for the layer in contact with the blue fluorescent material, energy transfer does not occur from the excited blue fluorescent material to the aromatic amine compound of the present invention. In addition, when the aromatic amine compound of the present invention is excited, energy can be transferred to the fluorescent material. Therefore, high luminous efficiency can be realized.

  Thus, by using the aromatic amine compound of the present invention and the hole transport layer, a light-emitting element having favorable characteristics can be obtained.

In this example, a method for synthesizing 4- (carbazol-9-yl) phenyl-3'-phenyltriphenylamine (abbreviation: mYGA1BP) represented by Structural Formula (69) will be described. A synthesis scheme of mYGA1BP is shown in (J-1).

  4- (N-carbazolyl) diphenylamine (1.9 g, 5.8 mmol) and sodium tert-butoxide (2.0 g, 21 mmol) were placed in a 200 mL three-necked flask, and the atmosphere in the flask was replaced with nitrogen. To this mixture, 30 mL of toluene, 0.1 mL of tri (tert-butyl) phosphine (10 wt% hexane solution), and 1.4 g (5.8 mmol) of 3-bromobiphenyl were added. The mixture was deaerated while being stirred under reduced pressure. After deaeration, 33 mg (0.06 mmol) of bis (dibenzylideneacetone) palladium (0) was added. The mixture was stirred at 80 ° C. for 5 hours. After the reaction, the reaction mixture was suction filtered through Florisil, Celite, and alumina, and the filtrate was concentrated to obtain a white solid. When this solid was recrystallized with dichloromethane and hexane, 2.1 g of the objective white powdery solid was obtained in a yield of 98%. It was confirmed by nuclear magnetic resonance (NMR) that this compound was 4- (carbazol-9-yl) phenyl-3′-phenyltriphenylamine (abbreviation: mYGA1BP) represented by the structural formula (69). .

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ = 7.07-7.12 (m, 1H), 7.17-7.20 (m, 1H), 7.27-7.47 (m, 20H) 7.53-7.56 (m, 2H), 8.14 (d, J = 7.8 Hz, 2H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 46B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG.

  When 1.9 g of the obtained mYGA1BP was purified by sublimation at a pressure of 5.9 Pa, an argon flow rate of 3.0 mL / min, and a heating temperature of 225 ° C. for 15 hours, 1.7 g of white (colorless) needle-like crystals of the target product was obtained. The recovery rate was 90%.

  Thermogravimetry-differential thermal analysis (TG-DTA) of mYGA1BP was performed. A high vacuum differential type differential thermal balance (Bruker AXS Co., Ltd., DTA2410SA) was used for the measurement. When measured under a reduced pressure of 10 Pa, the temperature at which the weight became 95% or less with respect to the weight at the start of the measurement was 224 ° C. from the relationship between weight and temperature (thermogravimetry). Further, when measured at normal pressure, the temperature at which the weight became 95% or less with respect to the weight at the start of measurement was 391 ° C. The rate of temperature increase was 10 ° C./min in all measurements.

  In addition, FIG. 47 shows an absorption spectrum of a toluene solution of mYGA1BP. In addition, FIG. 48 shows an absorption spectrum of the thin film of mYGA1BP. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. Samples were prepared by depositing the solution in a quartz cell and depositing the thin film on a quartz substrate. The absorption spectra obtained by subtracting the absorption spectrum of quartz are shown in FIGS. 47 and 48, respectively. 47 and 48, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed near 294 nm and 313 nm, and in the case of the thin film, absorption was observed near 317 nm. In addition, FIG. 49 shows an emission spectrum of a toluene solution of mYGA1BP (excitation wavelength: 350 nm). Further, FIG. 50 shows an emission spectrum of the thin film (excitation wavelength: 317 nm) of mYGA1BP. 49 and 50, the horizontal axis represents wavelength (nm), and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, a peak of the emission spectrum was observed at 392 nm (excitation wavelength: 350 nm) and in the case of the thin film: 402 nm (excitation wavelength: 317 nm).

  The HOMO level of mYGA1BP in the thin film state was −5.57 eV as a result of measurement by atmospheric photoelectron spectroscopy (AC-2, manufactured by Riken Keiki Co., Ltd.). Furthermore, using the data of the absorption spectrum of the thin film of mYGA1BP in FIG. 48, the absorption edge was obtained from the Tauc plot, and the absorption edge was estimated as the optical energy gap. The energy gap was 3.45 eV. Therefore, the LUMO level is −2.12 eV.

In this example, a method for synthesizing 4- (carbazol-9-yl) phenyl-2'-phenyltriphenylamine (abbreviation: oYGA1BP) represented by Structural Formula (70) will be described. The synthesis scheme is shown in (K-1).

  4- (N-carbazolyl) diphenylamine (1.9 g, 5.8 mmol) and sodium tert-butoxide (2.0 g, 21 mmol) were placed in a 200 mL three-necked flask, and the atmosphere in the flask was replaced with nitrogen. To this mixture were added 30 mL of toluene, 0.1 mL of tri (tert-butyl) phosphine (10 wt% hexane solution), and 1.4 g (5.8 mmol) of 2-bromobiphenyl. The mixture was deaerated while being stirred under reduced pressure. After deaeration, 33 mg (0.06 mmol) of bis (dibenzylideneacetone) palladium (0) was added. The mixture was stirred at 80 ° C. for 5 hours. After the reaction, the reaction mixture was suction filtered through Florisil, Celite, and alumina, and the filtrate was concentrated to obtain a white solid. When this solid was recrystallized from dichloromethane and hexane, 2.3 g of the target white powdery solid was obtained in a yield of 82%. It was confirmed by nuclear magnetic resonance (NMR) that this compound was 4- (carbazol-9-yl) phenyl-2′-phenyltriphenylamine (abbreviation: oYGA1BP) represented by the structural formula (70). .

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ = 6.91-6.96 (m, 3H), 7.06-7.09 (m, 2H), 7.12 (d, 8.7 Hz, 2H) 7.18-7.44 (m, 17H), 8.10-8.13 (m, 2H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 51B is a chart in which the range of 6.5 ppm to 8.5 ppm in FIG.

  When 2.0 g of the obtained oYGA1BP was purified by sublimation at a pressure of 5.9 Pa, an argon flow rate of 3.0 mL / min, and a heating temperature of 210 ° C. for 15 hours, 1.9 g of white (colorless) needle-like crystals of the target product was obtained. The recovery rate was 87%.

  Thermogravimetry-differential thermal analysis (TG-DTA) of oYGA1BP was performed. A high vacuum differential type differential thermal balance (Bruker AXS Co., Ltd., DTA2410SA) was used for the measurement. When measured under a reduced pressure of 10 Pa, the temperature at which the weight became 95% or less with respect to the weight at the start of the measurement was 208 ° C. from the relationship between the weight and temperature (thermogravimetry). Further, when measured at normal pressure, the temperature at which the weight became 95% or less with respect to the weight at the start of the measurement was 370 ° C. The rate of temperature increase was 10 ° C./min in all measurements.

  In addition, FIG. 52 shows an absorption spectrum of a toluene solution of oYGA1BP. In addition, FIG. 53 shows an absorption spectrum of the thin film of oYGA1BP. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The solution was put in a quartz cell, and the thin film was deposited on a quartz substrate to prepare a sample. The absorption spectra obtained by subtracting the absorption spectrum of quartz are shown in FIG. 52 and FIG. 52 and 53, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed near 294 nm and 311 nm, and in the case of the thin film, absorption was observed near 317 nm. In addition, FIG. 54 shows an emission spectrum of a toluene solution (excitation wavelength: 350 nm) of oYGA1BP. Further, FIG. 55 shows an emission spectrum of the thin film (excitation wavelength: 317 nm) of oYGA1BP. 54 and 55, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, the peak of the emission spectrum was observed at 404 nm (excitation wavelength: 350 nm), and in the case of the thin film, the peak was 407 nm (excitation wavelength: 317 nm).

  The HOMO level of oYGA1BP in the thin film state was −5.56 eV as a result of measurement by atmospheric photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-2). Furthermore, using the data of the absorption spectrum of the oYGA1BP thin film in FIG. 53, the absorption edge was obtained from the Tauc plot, and the absorption edge was estimated as the optical energy gap. The energy gap was 3.46 eV. Therefore, the LUMO level is −2.10 eV.

In this example, N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-di (1-naphthyl) biphenyl-4,4 ′ represented by Structural Formula (107) A method for synthesizing diamine (abbreviation: YGNBP) will be described.

[Step 1]
A method for synthesizing N, N′-di (1-naphthyl) benzidine will be described. A synthesis scheme (L-1) of N, N｀-di (1-naphthyl) benzidine is shown below.

  In a 500 mL three-necked flask, 20 g (50 mmol) of 4,4′-diiodobiphenyl, 14 g (100 mmol) of 1-naphthylamine, 580 mg (1 mmol) of bis (dibenzylideneacetone) palladium (0), 12 g (12 mmol) of sodium tert-butoxide In addition, 100 mL of dehydrated toluene was added, and the inside of the three-necked flask was decompressed for 3 minutes, and deaeration was performed until no bubbles were generated. To this mixture was added 6.0 mL (3.0 mmol) of tri (tert-butyl) phosphine (10 wt% hexane solution), and the mixture was heated and stirred at 100 ° C. in a nitrogen atmosphere. After 3 hours, heating was stopped, about 700 mL of a mixed solution of warm toluene and ethyl acetate was added to the reaction suspension, and the suspension was filtered through Florisil, alumina, and Celite. The obtained filtrate was washed with water, and magnesium sulfate was added to the organic layer for drying. This suspension was filtered, and the resulting filtrate was concentrated. After adding hexane to the concentrated solution, recrystallization was performed by irradiating with ultrasonic waves. The resulting solid was collected by filtration and dried. The target product (13 g) as a white powder was obtained in a yield of 57%. The Rf value (developing solvent: hexane: ethyl acetate = 2: 1) in silica gel thin layer chromatography (TLC) was 0.53 for the target product and 0.36 for 1-naphthylamine.

[Step 2]
A method for synthesizing N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-di (1-naphthyl) biphenyl-4,4′-diamine (abbreviation: YGNBP) will be described. A synthesis scheme (L-2) of YGNBP is shown below.

  In a 100 mL three-necked flask, 3.5 g (11 mmol) of 4-bromophenylcarbazole, 2.2 g (5.0 mmol) of N, N｀-di (1-naphthyl) benzidine, 30 mg of bis (dibenzylideneacetone) palladium (0) (0.1 mmol), 1.5 g (15 mmol) of sodium tert-butoxide was added, 20 mL of dehydrated xylene was added, and the inside of the three-necked flask was depressurized for 3 minutes to perform deaeration until no bubbles appeared. Tri (tert-butyl) phosphine (10 wt% hexane solution) 0.6 mL (0.3 mmol) was added, and the mixture was heated and stirred at 130 ° C. in a nitrogen atmosphere. After 4 hours, heating was stopped, and about 200 mL of toluene was added to the reaction suspension, followed by filtration through Florisil, alumina, and celite. The obtained filtrate was washed with water, and magnesium sulfate was added to the organic layer for drying. This suspension was further filtered through Florisil, alumina, and celite, and the obtained filtrate was concentrated. Acetone and hexane were added to the concentrate, and then recrystallization was performed by irradiating ultrasonic waves. The resulting solid was collected by filtration and dried to obtain 2.0 g of the desired product as a pale yellow powder in a yield of 43%. N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-di (1-naphthyl) represented by the structural formula (107) by nuclear magnetic resonance (NMR). ) Biphenyl-4,4′-diamine (abbreviation: YGNBP) was confirmed.

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ (ppm) = 7.19-7.58 (m, 36H), 7.84 (d, J = 7.8, 2H), 7.93 (d, J = 7.8, 2H), 8.05 (d, J = 8.1, 2H), 8.12 (d, J = 7.2, 4H). In addition, ¹ H NMR charts are shown in FIGS. 56 (A) and 56 (B). Note that FIG. 56B is a chart in which the range of 6.0 ppm to 9.0 ppm in FIG.

In addition, ¹³ C NMR data of this compound is shown below. ¹³ C NMR (75.5 MHz, CDCl ₃ ): δ (ppm) = 109.82, 119.65, 120.23, 122.06, 122.47, 123.15, 124.10, 125.78, 126 .34, 126.45, 126.69, 126.99, 127.36, 127.47, 127.86, 128.55, 130.69, 131.26, 134.41, 135.40, 141.12 , 143.02, 146.85, 147.53. In addition, ¹³ C NMR charts are shown in FIGS. Note that FIG. 57B is a chart in which the range of 100 ppm to 160 ppm in FIG.

  Thermogravimetry-differential thermal analysis (TG-DTA) of YGNBP was performed. A high vacuum differential type differential thermal balance (Bruker AXS Co., Ltd., DTA2410SA) was used for the measurement. When measured under a reduced pressure of 10 Pa, the temperature at which the weight became 95% or less with respect to the weight at the start of the measurement was 390 ° C. from the relationship between weight and temperature (thermogravimetry). Further, when measured at normal pressure, it showed a weight of 99% with respect to the weight at the start of measurement at 500 ° C., and showed excellent heat resistance. The rate of temperature increase was 10 ° C./min in all measurements.

  Further, the glass transition point of YGNBP was measured using a differential scanning calorimeter (DSC, manufactured by Perkin Elmer, Pyris 1). The DSC chart of FIG. 72 was obtained by raising the temperature to 500 ° C. at 10 ° C./min. In FIG. 72, temperature is shown on the X-axis and heat flow is shown on the Y-axis. On the Y axis, the upward direction indicates endotherm. From this chart, it was found that the glass transition point (Tg) of YGNBP was 171 ° C., indicating a high glass transition point.

  Further, FIG. 58 shows an absorption spectrum of a toluene solution of YGNBP and an absorption spectrum of a thin film of YGNBP. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The solution was put in a quartz cell, and the thin film was deposited on a quartz substrate to prepare a sample. The absorption spectrum obtained by subtracting the absorption spectrum of quartz is shown in FIG. 58, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 345 nm, and in the case of the thin film, absorption was observed at around 349 nm. In addition, FIG. 59 shows an emission spectrum of a toluene solution of YGNBP (excitation wavelength: 350 nm) and an emission spectrum of a thin film of YGNBP (excitation wavelength: 349 nm). In FIG. 59, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, a peak of the emission spectrum was observed at 435 nm (excitation wavelength: 350 nm) and in the case of the thin film, at 526 nm (excitation wavelength: 349 nm).

  The HOMO level of YGNBP in a thin film state was −5.34 eV as a result of measurement by atmospheric photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-2). Further, using the data of the absorption spectrum of the YGNBP thin film in FIG. 58, the absorption edge was obtained from the Tauc plot, and the absorption edge was estimated as the optical energy gap. The energy gap was 3.19 eV. Therefore, the LUMO level is −2.15 eV.

In this example, N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-diphenylbiphenyl-4,4′-diamine represented by the structural formula (115) is used. A method for synthesizing (abbreviation: CNABP) will be described.

[Step 1]
A method for synthesizing 9- (4-bromo-1-naphthyl) carbazole will be described. A synthesis scheme (M-1) of 9- (4-bromo-1-naphthyl) carbazole is shown below.

  In a 300 mL three-necked flask, 14 g (50 mmol) of 1,4-dibromonaphthalene, 6.7 g (40 mmol) of carbazole, 1.9 g (10 mmol) of copper (I) iodide, 1 of 18-crown-6-ether 3 g (5.0 mmol), 10 g of potassium carbonate (72 mmol), 8 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone (abbreviation: DMPU) were added, and nitrogen atmosphere was added. The mixture was heated and stirred at 170 ° C. for about 30 hours. The reaction suspension was cooled to room temperature, and 300 mL of warm toluene was added, followed by filtration through celite. The obtained filtrate was washed with water, dilute hydrochloric acid, water, aqueous sodium hydrogen carbonate solution and water in this order, and dried over magnesium sulfate added to the organic layer. This suspension was filtered through Florisil and Celite, and the obtained filtrate was concentrated. The concentrated solution was fractionated by silica gel chromatography (toluene: hexane = 1: 1) to obtain 7.5 g of the desired product as a white powder in a yield of 50%. This compound was confirmed to be 9- (4-bromo-1-naphthyl) carbazole by nuclear magnetic resonance (NMR).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ (ppm) = 6.93-6.96 (m, 2H), 7.25-7.33 (m, 6H), 7.45 (d, J = 7 .8, 1H), 7.60 (t, J = 6.9, 1H), 7.94 (d, J = 7.8, 1H), 8.16-8.19 (m, 2H), 8 .38 (d, J = 8.7, 1H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 60B is a chart in which the range of 6.0 ppm to 9.0 ppm in FIG.

[Step 2]
A method for synthesizing N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-diphenylbiphenyl-4,4′-diamine (abbreviation: CNABP) will be described. A synthesis scheme (M-2) of CNABP is shown below.

  In a 100 mL three-necked flask, 3.4 g (9 mmol) of 9- (4-bromo-1-naphthyl) carbazole, 1.4 g (4 mmol) of N, N｀-diphenylbenzidine, 60 mg of bis (dibenzylideneacetone) palladium (0) (0.1 mmol), 1.5 g (15 mmol) of sodium tert-butoxide was added, 20 mL of dehydrated xylene was added, and the inside of the three-necked flask was depressurized for 3 minutes to perform deaeration until no bubbles appeared. Tri (tert-butyl) phosphine (10 wt% hexane solution) 0.6 mL (0.3 mmol) was added, and the mixture was heated and stirred at 120 ° C. in a nitrogen atmosphere. After 4 hours, heating was stopped, and about 200 mL of toluene was added to the reaction suspension, followed by filtration through Florisil, alumina, and celite. The obtained filtrate was washed with water and dried by adding magnesium sulfate. The suspension was further filtered through Florisil, alumina, and celite. The obtained filtrate was concentrated, acetone and hexane were added, and recrystallization was performed by irradiation with ultrasonic waves. The resulting solid was collected by filtration and dried. The target product (2.7 g) as a pale yellow powder was obtained in a yield of 73%. N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-diphenylbiphenyl represented by the structural formula (115) by nuclear magnetic resonance (NMR). It was confirmed that it was −4,4′-diamine (abbreviation: CNABP).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ (ppm) = 7.03 (t, J = 7.2, 2H), 7.09 (d, J = 7.8, 4H), 7.15-7 .19 (m, 8H), 7.25-7.43 (m, 18H), 7.48-7.53 (m, 6H), 7.63 (d, J = 7.8, 2H), 8 .12 (d, J = 8.4, 2H), 8.22 (d, J = 6.9, 4H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 61B is a chart in which the range of 6.0 ppm to 9.0 ppm in FIG.

  CNABP thermogravimetry-differential thermal analysis (TG-DTA) was performed. A high vacuum differential type differential thermal balance (Bruker AXS Co., Ltd., DTA2410SA) was used for the measurement. When measured under a reduced pressure of 10 Pa, the temperature at which the weight became 95% or less with respect to the weight at the start of measurement was 380 ° C. from the relationship between weight and temperature (thermogravimetry). When measured at normal pressure, it showed a weight of 94% with respect to the weight at the start of measurement at 500 ° C., indicating excellent heat resistance. The rate of temperature increase was 10 ° C./min in all measurements.

  Further, the glass transition point of CNABP was measured using a differential scanning calorimeter (DSC, manufactured by Perkin Elmer, Pyris 1). The DSC chart of FIG. 73 was obtained by heating up to 500 ° C. at 10 ° C./min. In FIG. 73, temperature is shown on the X axis and heat flow is shown on the Y axis. On the Y axis, the upward direction indicates endotherm. From this chart, it was found that the glass transition point (Tg) of CNABP was 183 ° C., indicating a high glass transition point.

  Further, FIG. 62 shows an absorption spectrum of a CNABP toluene solution and an absorption spectrum of a CNABP thin film. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The solution was put in a quartz cell, and the thin film was deposited on a quartz substrate to prepare a sample. The absorption spectrum obtained by subtracting the absorption spectrum of quartz was shown in FIG. In FIG. 62, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed near 338 nm and 380 nm, and in the case of the thin film, absorption was observed near 340 nm and 383 nm. Further, FIG. 63 shows an emission spectrum of a CNABP toluene solution (excitation wavelength: 340 nm) and an emission spectrum of a CNABP thin film (excitation wavelength: 383 nm). In FIG. 63, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, peaks of the emission spectrum were observed at 455 nm (excitation wavelength: 340 nm), and in the case of the thin film, at 499 nm and 522 nm (excitation wavelength: 383 nm).

  The HOMO level of CNABP in the thin film state was −5.43 eV as a result of measurement by atmospheric photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-2). Furthermore, using the data of the absorption spectrum of the CNABP thin film in FIG. 62, the absorption edge was obtained from the Tauc plot, and the absorption edge was estimated as the optical energy gap. The energy gap was 2.90 eV. Therefore, the LUMO level is −2.53 eV.

In this example, N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-di-1-naphthylbiphenyl-4, represented by the structural formula (120), A method for synthesizing 4′-diamine (abbreviation: CNNBP) will be described. A synthesis scheme (N-1) of CNNBP is shown below.

  In a 100 mL three-necked flask, 3.4 g (9 mmol) of 9- (4-bromo-1-naphthyl) carbazole, 1.8 g (4 mmol) of N, N｀-di (1-naphthyl) benzidine, bis (dibenzylideneacetone) Palladium (0) 60 mg (0.1 mmol) and sodium tert-butoxide 1.5 g (15 mmol) were added, dehydrated xylene 20 mL was added, and the inside of the three-necked flask was depressurized for 3 minutes until no bubbles were generated. Tri (tert-butyl) phosphine (10 wt% hexane solution) 0.6 mL (0.3 mmol) was added, and the mixture was heated and stirred at 130 ° C. in a nitrogen atmosphere. After 4 hours, heating was stopped, and about 200 mL of toluene was added to the reaction suspension, followed by filtration through Florisil, alumina, and celite. The obtained filtrate was washed with water, and magnesium sulfate was added to the organic layer for drying. The suspension was further filtered through Florisil, alumina, and celite. The obtained filtrate was concentrated, acetone and hexane were added, and recrystallization was performed by irradiation with ultrasonic waves. The resulting solid was collected by filtration and dried to obtain 0.8 g of the desired product as a pale yellow powder in a yield of 20%. N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-di- represented by the structural formula (120) by nuclear magnetic resonance (NMR). It was confirmed that it was 1-naphthylbiphenyl-4,4′-diamine (abbreviation: CNNBP).

¹ H NMR data of this compound is shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ (ppm) = 6.88 (d, J = 8.1, 4H), 7.05 (d, J = 7.8, 4H), 7.26-7 .53 (m, 30H), 7.76 (d, J = 7.8, 2H), 7.92 (d, J = 8.4, 2H), 8.14 (d, J = 7.8, 2H), 8.19-8.23 (m, 6H). In addition, ¹ H NMR charts are shown in FIGS. Note that FIG. 64B is a chart in which the range of 6.0 ppm to 9.0 ppm in FIG.

  CNNBP was subjected to thermogravimetry-differential thermal analysis (TG-DTA). A high vacuum differential type differential thermal balance (Bruker AXS Co., Ltd., DTA2410SA) was used for the measurement. When measured under a reduced pressure of 10 Pa, the temperature at which the weight became 95% or less with respect to the weight at the start of measurement was 400 ° C. from the relationship between weight and temperature (thermogravimetry). When measured at normal pressure, it showed a weight of 98% with respect to the weight at the start of measurement at 500 ° C., indicating excellent heat resistance. The rate of temperature increase was 10 ° C./min in all measurements.

  Moreover, the glass transition point of CNNNBP was measured using a differential scanning calorimeter (DSC, manufactured by PerkinElmer, Inc., Pyris 1). The DSC chart of FIG. 74 was obtained by heating up to 500 ° C. at 10 ° C./min. In FIG. 74, temperature is shown on the X axis and heat flow is shown on the Y axis. On the Y axis, the upward direction indicates endotherm. From this chart, it was found that the glass transition point (Tg) of CNNBP was 213 ° C., indicating a high glass transition point.

  In addition, FIG. 65 shows an absorption spectrum of a CNNNBP toluene solution and an absorption spectrum of a CNNNBP thin film. An ultraviolet-visible spectrophotometer (manufactured by JASCO Corporation, model V550) was used for the measurement. The solution was put in a quartz cell, and the thin film was deposited on a quartz substrate to prepare a sample. The absorption spectrum obtained by subtracting the absorption spectrum of quartz is shown in FIG. In FIG. 65, the horizontal axis represents wavelength (nm) and the vertical axis represents absorption intensity (arbitrary unit). In the case of the toluene solution, absorption was observed at around 370 nm, and in the case of the thin film, absorption was observed at around 374 nm. Further, FIG. 66 shows an emission spectrum of a CNNNBP toluene solution (excitation wavelength: 370 nm) and an emission spectrum of a CNNNBP thin film (excitation wavelength: 374 nm). In FIG. 66, the horizontal axis represents wavelength (nm) and the vertical axis represents emission intensity (arbitrary unit). In the case of the toluene solution, the peak of the emission spectrum was observed at 450 nm (excitation wavelength: 370 nm), and in the case of the thin film, the peak was 545 nm (excitation wavelength: 374 nm).

  The HOMO level of CNNBP in the thin film state was −5.45 eV as a result of measurement by atmospheric photoelectron spectroscopy (manufactured by Riken Keiki Co., Ltd., AC-2). Furthermore, using the data of the absorption spectrum of the CNNBP thin film in FIG. 65, the absorption edge was obtained from the Tauc plot, and the absorption edge was estimated as the optical energy gap. The energy gap was 3.00 eV. Therefore, the LUMO level is -2.45 eV.

  In this example, a light-emitting element of the present invention will be described with reference to FIG. The chemical formula of the material used in this example is shown below.

(Light emitting element 7)
First, indium tin oxide containing silicon oxide was formed over a glass substrate 2201 by a sputtering method, so that a first electrode 2202 was formed. The film thickness was 110 nm and the electrode area was 2 mm × 2 mm.

Next, the substrate on which the first electrode is formed is fixed to a substrate holder provided in the vacuum evaporation apparatus so that the surface on which the first electrode is formed is downward, and the pressure is reduced to about 10 ⁻⁴ Pa. After that, NPB and molybdenum oxide (VI) were co-evaporated on the first electrode 2202, so that a layer 2203 including a composite material formed by combining an organic compound and an inorganic compound was formed. The film thickness was 50 nm, and the weight ratio of NPB and molybdenum oxide (VI) was adjusted to 4: 1 (= NPB: molybdenum oxide). Note that the co-evaporation method is an evaporation method in which evaporation is performed simultaneously from a plurality of evaporation sources in one processing chamber.

  Next, 4- (carbazol-9-yl) phenyl-4′-phenyltriphenylamine represented by the structural formula (52) (abbreviation: abbreviation :) is formed over the layer 2203 containing the composite material by an evaporation method using resistance heating. YGA1BP) was formed to a thickness of 10 nm, whereby a hole transport layer 2204 was formed.

  Further, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) and N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N ′ A light-emitting layer 2205 having a thickness of 30 nm was formed on the hole-transport layer 2204 by co-evaporation with -diphenylstilbene-4,4′-diamine (abbreviation: YGA2S). Here, the weight ratio of CzPA to YGA2S was adjusted to be 1: 0.04 (= CzPA: YGA2S).

  Thereafter, Alq was deposited to a thickness of 20 nm on the light-emitting layer 2205 using a resistance heating vapor deposition method to form a first electron-transport layer 2206a.

  Further, using a vapor deposition method using resistance heating, bathophenanthroline (abbreviation: BPhen) was formed to a thickness of 10 nm over the first electron-transport layer 2206a, whereby a second electron-transport layer 2206b was formed.

  Further, an electron injection layer 2207 having a thickness of 1 nm was formed by vapor deposition of lithium fluoride on the second electron transport layer 2206b by using a resistance heating vapor deposition method.

  Finally, a light-emitting element 7 was manufactured by forming a second electrode 2208 by depositing aluminum on the electron injection layer 2207 so as to have a thickness of 200 nm using a resistance heating vapor deposition method. .

(Light emitting element 8)
As the hole-transport layer 2204, 4- (carbazol-9-yl) phenyl-2′-phenyltriphenylamine (abbreviation: oYGA1BP) represented by the structural formula (70) is formed to a thickness of 10 nm. did. The layers other than the hole transport layer were formed in the same manner as the light-emitting element 7.

(Light emitting element 9)
As the hole-transport layer 2204, 4- (carbazol-9-yl) phenyl-3′-phenyltriphenylamine (abbreviation: mYGA1BP) represented by the structural formula (69) is formed to a thickness of 10 nm. did. The layers other than the hole transport layer were formed in the same manner as the light-emitting element 7.

(Comparative light emitting element 10)
As the hole transport layer 2204, NPB was formed to a thickness of 10 nm. The layers other than the hole transport layer were formed in the same manner as the light-emitting element 7.

  68 shows current density-luminance characteristics of the light-emitting elements 7 to 9 and the comparative light-emitting element 10. In FIG. In addition, FIG. 69 shows voltage-luminance characteristics. In addition, FIG. 70 shows luminance-current efficiency characteristics. In addition, FIG. 71 shows an emission spectrum when a current of 1 mA is passed.

  As can be seen from FIG. 69, the light-emitting element using the aromatic amine compound of the present invention exhibits high current efficiency despite the chromaticity coordinates similar to those of the comparative light-emitting element 10. In addition, FIG. 68 shows that the light-emitting element of the present invention exhibits substantially the same drive voltage as that of the comparative light-emitting element 10. Therefore, by using the aromatic amine compound of the present invention, a light-emitting element with high power efficiency and low power consumption can be obtained.

Specifically, the comparative light-emitting element 10 has CIE chromaticity coordinates (x = 0.16, y = 0.17) at a luminance of 930 cd / m ² , and emitted blue light. The current efficiency at a luminance of 930 cd / m ² was 3.9 cd / A. In addition, when the luminance was 930 cd / m ² , the voltage was 4.8 V, the current density was 24 mA / cm ² , and the power efficiency was 2.6 lm / W.

On the other hand, the CIE chromaticity coordinates of the light-emitting element 7 at a luminance of 1090 cd / m ² were (x = 0.16, y = 0.17), and emitted blue light. In addition, the current efficiency at a luminance of 1090 cd / m ² was 7.2 cd / A, indicating high efficiency. In addition, when the luminance was 1090 cd / m ² , the voltage was 4.6 V, the current density was 15 mA / cm ² , and the power efficiency was 4.9 lm / W, which showed high power efficiency.

The light-emitting element 8 exhibited blue light emission with CIE chromaticity coordinates (x = 0.16, y = 0.17) at a luminance of 930 cd / m ² . The current efficiency at a luminance of 930 cd / m ² was 7.6 cd / A, indicating high efficiency. In addition, when the luminance was 930 cd / m ² , the voltage was 4.6 V, the current density was 12 mA / cm ² , and the power efficiency was 5.2 lm / W, which showed high power efficiency.

The light emitting element 9 emitted blue light. In addition, the current efficiency at a luminance of 930 cd / m ² was 7.4 cd / A, indicating high efficiency. In addition, when the luminance was 930 cd / m ² , the voltage was 4.8 V, the current density was 13 mA / cm ² , and the power efficiency was 4.8 lm / W, which showed high power efficiency.

  Further, as described above, YGA1BP, which is the aromatic amine compound of the present invention, has higher triplet excitation energy than NPB used in comparative light-emitting element 10. In particular, YGA1BP has a high triplet excitation energy that is an asymmetric structure. The wavelength corresponding to the triplet excitation energy of the aromatic amine compound of the present invention is around 450 nm, which corresponds to blue. The wavelength corresponding to the triplet excitation energy of NPB used in the comparative light-emitting element 10 is 500 nm, which corresponds to green. The singlet excitation energy is higher than the triplet excitation energy. That is, since the wavelength corresponding to the triplet excitation energy of the aromatic amine compound of the present invention corresponds to blue, the wavelength corresponding to the singlet excitation energy is shorter than blue. Therefore, when an aromatic amine compound is used for the layer in contact with the blue fluorescent material, energy transfer does not occur from the excited blue fluorescent material to the aromatic amine compound of the present invention. In addition, when the aromatic amine compound of the present invention is excited, energy can be transferred to the fluorescent material. Therefore, high luminous efficiency can be realized.

  As described above, by using the aromatic amine compound of the present invention as the hole transport layer, a light-emitting element having favorable characteristics can be obtained.

In this example, materials used in other examples will be described.

≪Synthesis example of YGAO11≫
Hereinafter, 2- (4- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} phenyl) -5-phenyl-1,3,4 represented by Structural Formula (201) A method for synthesizing oxadiazole (abbreviation: YGAO11) will be described.

[Step 1]
The synthesis of 2- (4-bromophenyl) -5-phenyl-1,3,4-oxadiazole (abbreviation: O11Br) will be described. In Step 1, O11Br was synthesized according to the following procedures (i) to (iii).

(I) Synthesis of 4-bromobenzohydrazide First, 3.0 g (13.9 mmol) of methyl-4-bromobenzoate was placed in a 100 mL three-necked flask, 10 mL of ethanol was added and stirred, and then 4.0 mL of hydrazine monohydrate. And heated and stirred at 78 ° C. for 5 hours. The obtained solid was washed with water and collected by suction filtration to obtain 2.0 g of a white solid of 4-bromobenzohydrazide as a target product (yield 67%).

(Ii) Synthesis of 1-benzoyl-2- (4-bromobenzoyl) hydrazine Next, 2.0 g (13.9 mmol) of 4-bromobenzohydrazide obtained in (i) above was placed in a 300 mL three-necked flask, and N- After adding 7 mL of methyl-2-pyrrolidone (abbreviation: NMP) and stirring, a mixture of 2.5 mL of N-methyl-2-pyrrolidone and 2.5 mL (21.5 mmol) of benzoyl chloride was added dropwise with a 50 mL dropping funnel, Stir at 0 ° C. for 3 hours. The obtained solid was washed with water and an aqueous sodium carbonate solution in this order, and collected by suction filtration. When recrystallization was performed with acetone, 3.6 g of a white solid of 1-benzoyl-2- (4-bromobenzoyl) hydrazine as a target product was obtained (yield 80%).

(Iii) Synthesis of O11Br Further, 15 g (47 mmol) of 1-benzoyl-2- (4-bromobenzoyl) hydrazine obtained by the method shown in (ii) above was placed in a 200 mL three-necked flask, and 100 mL of phosphoryl chloride was added, The mixture was heated and stirred at 100 ° C. for 5 hours. After the reaction, phosphoryl chloride was completely distilled off, and the resulting solid was washed with water and an aqueous sodium carbonate solution in this order, and collected by suction filtration. When recrystallization was performed with methanol, 13 g of a white solid of O11Br, which was the target product of Step 1, was obtained (yield 89%). The synthesis scheme of Step 1 described above is shown in the following scheme (E-1).

[Step 2]
Synthesis of <2- (4- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} phenyl) -5-phenyl-1,3,4-oxadiazole (abbreviation: YGAO11) >
O11Br (3.0 g, 10.0 mmol) obtained in Step 1, YGA (3.4 g, 10.0 mmol) obtained in Step 1 of Example 1 and sodium tert-butoxide (1.9 g, 19.9 mmol) were placed in a 100 mL three-necked flask. Then, 45 mL of toluene, 0.3 mL of a 10% hexane solution of tri (tert-butyl) phosphine, and 0.3 g (0.6 mmol) of bis (dibenzylideneacetone) palladium (0) were added, and the mixture was stirred at 120 ° C. for 5 hours. Stir with heating. After the reaction, the mixture was filtered through celite, and the filtrate was washed with water and dried over magnesium sulfate. After drying, the solution was filtered and the filtrate was concentrated. The obtained solid was dissolved in toluene and purified by silica column chromatography. Column purification was performed by first using toluene as a developing solvent and then using a mixed solvent of toluene: ethyl acetate = 1: 1 as a developing solvent. When recrystallization was performed with chloroform and hexane, 4.7 g of a light yellow solid of YGAO11, which was the target product of this synthesis example, was obtained (yield 85%). The synthesis scheme of Step 3 described above is shown in the following scheme (E-2).

Incidentally, it shows the analysis result by the obtained YGAO11 nuclear magnetic resonance spectroscopy ⁽¹ H NMR) below. A ¹ H NMR chart is shown in FIG. 43 (a), and an enlarged view thereof is shown in FIG. 43 (b).

¹ H NMR (300 MHz, CDCl ₃ ): δ = 7.14-7.53 (m, 19H), δ = 8.03 (d, J = 8.7, 2H), δ = 8.11-8. 15 (m, 4H).

≪YGAPA synthesis example≫
Hereinafter, 9- (4- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} phenyl) -10-phenylanthracene (abbreviation: YGAPA) represented by Structural Formula (202) The synthesis method will be described.

[Step 1]
A method for synthesizing 9-phenyl-10- (4-bromophenyl) anthracene (abbreviation: PA) will be described.
(I) Synthesis of 9-phenylanthracene A synthesis scheme (F-1) of 9-phenylanthracene is shown below.

5.4 g (21.1 mmol) of 9-bromoanthracene, 2.6 g (21.1 mmol) of phenylboronic acid, 60 mg (0.21 mmol) of palladium acetate (Pd (OAc) ₂ ), potassium carbonate (K ₂ CO ₃ ) 10 mL (20 mmol) of aqueous solution (2 mol / L), 263 mg (0.84 mmol) of tri (o-tolyl) phosphine (P (o-tolyl) ₃ ), 1,2-dimethoxyethane (abbreviation: DME) 20 mL was mixed and stirred at 80 ° C. for 9 hours. After the reaction, the precipitated solid was collected by suction filtration, dissolved in toluene, and filtered through Florisil, Celite, and alumina. The filtrate was washed with water and saturated brine, and dried over magnesium sulfate. After natural filtration, the filtrate was concentrated to obtain 21.5 g of a light brown solid of 9-phenylanthracene, which was the target product, in a yield of 85%.

(Ii) Synthesis of 10-bromo-9-phenylanthracene A synthesis scheme (F-2) of 10-bromo-9-phenylanthracene is shown below.

6.0 g (23.7 mmol) of 9-phenylanthracene was dissolved in 80 mL of carbon tetrachloride, and a solution of 3.80 g (21.1 mmol) of bromine in 10 mL of carbon tetrachloride was added dropwise to the reaction solution using a dropping funnel. . After completion of dropping, the mixture was stirred at room temperature for 1 hour. After the reaction, an aqueous sodium thiosulfate solution was added to stop the reaction. The organic layer was washed with aqueous sodium hydroxide (NaOH) solution and saturated brine, and dried over magnesium sulfate. After natural filtration, the solution was concentrated, dissolved in toluene, and filtered through Florisil, Celite, and alumina. The filtrate was concentrated and recrystallized with dichloromethane and hexane to obtain 7.0 g (yield 89%) of 10-bromo-9-phenylanthracene as a target product.

(Iii) Synthesis of 9-iodo-10-phenylanthracene A synthesis scheme (F-3) of 9-iodo-10-phenylanthracene is shown below.

After dissolving 3.33 g (10 mmol) of 9-bromo-10-phenylanthracene in 80 mL of tetrahydrofuran (abbreviation: THF) and setting to −78 ° C., n-BuLi (1.6 mol / L) was added to the reaction solution from the dropping funnel. 7.5 mL (12.0 mmol) was added dropwise and stirred for 1 hour. A solution prepared by dissolving 5 g (20.0 mmol) of iodine in 20 mL of THF was added dropwise, and the mixture was further stirred at −78 ° C. for 2 hours. After the reaction, an aqueous sodium thiosulfate solution was added to stop the reaction. The organic layer was washed with aqueous sodium thiosulfate solution and saturated brine, and dried over magnesium sulfate. The solution after natural filtration was concentrated and recrystallized with ethanol to obtain 3.1 g of a target substance, 9-iodo-10-phenylanthracene, which was a pale yellow solid in a yield of 83%.

(Iv) Synthesis of 9-phenyl-10- (4-bromophenyl) anthracene (abbreviation: PA) Synthesis scheme (F-4) of 9-phenyl-10- (4-bromophenyl) anthracene (abbreviation: PA) It is shown below.

1.0-g (2.63 mmol) of 9-iodo-10-phenylanthracene, 542 mg (2.70 mmol) of p-bromophenylboronic acid, tetrakis (triphenylphosphine) palladium (0) (Pd (PPh ₃ ) ₄ ) 46 mg (0.03 mmol), 3 mL (6 mmol) of 2 mol / L calcium carbonate (K ₂ CO ₃ ) aqueous solution and 10 mL of toluene were collected and mixed, and stirred at 80 ° C. for 9 hours. After the reaction, toluene was added, followed by filtration through Florisil, Celite, and alumina. The filtrate was washed with water and saturated brine, and dried over magnesium sulfate. After natural filtration, the filtrate was concentrated and recrystallized with chloroform and hexane to obtain 562 mg of a light brown solid of 9-phenyl-10- (4-bromophenyl) anthracene, which was the target product, in a yield of 45%.

[Step 2]
A method for synthesizing 9- (4- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} phenyl) -10-phenylanthracene (abbreviation: YGAPA) will be described. A synthesis scheme (F-5) of YGAPA is shown below.

409 mg (1.0 mmol) of 9-phenyl-10- (4-bromophenyl) anthracene, 339 mg (1.0 mmol) of YGA obtained in Step 1 of Example 1, bis (dibenzylideneacetone) palladium (0) 6 mg (0.01 mmol), sodium tert-butoxide 500 mg (5.2 mmol), tri (tert-butyl) phosphine (10 wt% hexane solution) 0.1 mL, toluene 10 mL were added and mixed. Stir for hours. After the reaction, the reaction solution was washed with water, the aqueous layer was extracted with toluene, combined with the organic layer, washed with saturated brine, and dried over magnesium sulfate. The oily product obtained by natural filtration and concentration was purified by silica gel column chromatography (hexane: toluene = 7: 3), and recrystallized from dichloromethane and hexane. As a result, 534 mg yield of YGAPA, a yellow powdered solid, was obtained. Obtained at 81%. When this compound was measured by a nuclear magnetic resonance method (NMR), 9- (4- {N- [4- (carbazol-9-yl) phenyl] -N-phenylamino} phenyl) -10-phenylanthracene (abbreviation) : YGAPA). ¹ H NMR of YGAPA is shown in FIGS. 44 (A) and (B).

≪CzPA synthesis example≫
Hereinafter, a method for synthesizing 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) represented by the structural formula (203) will be described.

  A synthesis scheme (H-1) of 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) is shown below.

1.3-g (3.2 mmol) of 9-phenyl-10- (4-bromophenyl) anthracene, 578 mg (3.5 mmol) of carbazole, 50 mg (0.10 mmol) of bis (dibenzylideneacetone) palladium (0), 1.0 g (10 mmol) of tert-butoxy sodium, 0.1 mL of tri (tert-butyl) phosphine (10 wt% hexane solution) and 30 mL of toluene were added and mixed, and the mixture was heated to reflux at 110 ° C. for 10 hours. After the reaction, the reaction solution was washed with water, the aqueous layer was extracted with toluene, combined with the organic layer, washed with saturated brine, and dried over magnesium sulfate. The oily substance obtained by natural filtration and concentration of the filtrate was purified by silica gel column chromatography (hexane: toluene = 7: 3) and recrystallized from dichloromethane and hexane to obtain the desired product 9- [4- (N -Carbazolyl)] phenyl-10-phenylanthracene (abbreviation: CzPA) was obtained in 1.5 g in a yield of 93%.

The NMR data of the obtained CzPA are shown below. ¹ H NMR (300 MHz, CDCl ₃ ): δ = 8.22 (d, J = 7.8 Hz, 2H), 7.86-7.82 (m, 3H), 7.61-7.36 (m, 20H). In addition, FIG. 45 shows a ¹ H NMR chart.

The obtained CzPA 5.50 g was purified by sublimation for 20 hours under the conditions of 270 ° C., argon stream (flow rate 3.0 mL / min) and pressure 6.7 Pa. 3.98 g was recovered and the recovery rate was 72%.

4A and 4B illustrate a light-emitting element of the present invention. 4A and 4B illustrate a light-emitting element of the present invention. 4A and 4B illustrate a light-emitting device of the present invention. 4A and 4B illustrate a light-emitting device of the present invention. 8A and 8B each illustrate an electronic device of the invention. 8A and 8B each illustrate an electronic device of the invention. 4A and 4B illustrate a light-emitting device of the present invention. 4A and 4B illustrate a light-emitting device of the present invention. 4A and 4B illustrate a light-emitting element of the present invention. It shows ¹ H NMR charts of 9- [4- (N- phenylamino) phenyl] carbazole. N- [4- (carbazol-9-yl) phenyl] -N- phenyl-9,9 diagram showing ¹ H NMR charts of dimethyl fluorenyl-2-amine. The figure which shows the DSC chart of N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2-amine. The figure which shows the absorption spectrum of the toluene solution of N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2-amine. FIG. 9 shows an absorption spectrum of a thin film of N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2-amine. The figure which shows the emission spectrum of the toluene solution of N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2-amine. FIG. 9 shows an emission spectrum of a thin film of N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2-amine. The figure which shows the CV measurement result of N- [4- (carbazol-9-yl) phenyl] -N-phenyl-9,9-dimethylfluorenyl-2-amine. 4- (carbazol-9-yl) shows a 4'phenyltriphenylamine ¹ H NMR charts. The figure which shows the DSC chart of 4- (carbazol-9-yl) phenyl-4'-phenyltriphenylamine. The figure which shows the emission spectrum of the toluene solution of 4- (carbazol-9-yl) phenyl-4'-phenyltriphenylamine. Shows N, N'- bis [4- (carbazol-9-yl) phenyl] -N, a N'- diphenyl-9,9 ¹ H NMR charts of dimethyl-2,7-diamine. The figure which shows the DSC chart of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-9,9-dimethylfluorene-2,7-diamine. The figure which shows the absorption spectrum of the toluene solution of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-9,9-dimethylfluorene-2,7-diamine. The figure which shows the absorption spectrum of the thin film of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-9,9-dimethylfluorene-2,7-diamine. The figure which shows the emission spectrum of the toluene solution of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-9,9-dimethylfluorene-2,7-diamine. The figure which shows the emission spectrum of the thin film of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-9,9-dimethylfluorene-2,7-diamine. The figure which shows the CV measurement result of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-9,9-dimethylfluorene-2,7-diamine. N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-4,4'-biphenyl - shows ¹ H NMR charts of diamine. The figure which shows the DSC chart of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-4,4'-biphenyl-diamine. The figure which shows the absorption spectrum of the toluene solution of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-4,4'-biphenyl-diamine. The figure which shows the absorption spectrum of the thin film of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-4,4'-biphenyl-diamine. The figure which shows the emission spectrum of the toluene solution of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-4,4'-biphenyl-diamine. The figure which shows the emission spectrum of the thin film of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-4,4'-biphenyl-diamine. The figure which shows the CV measurement result of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-diphenyl-4,4'-biphenyl-diamine. 6A and 6B illustrate a light-emitting element of Example 5. FIG. 10 shows current density-luminance characteristics of the light-emitting element manufactured in Example 5. FIG. 10 shows voltage-luminance characteristics of the light-emitting element manufactured in Example 5. FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element manufactured in Example 5. FIG. 13 shows current density-luminance characteristics of the light-emitting element manufactured in Example 6. FIG. 14 shows voltage-luminance characteristics of the light-emitting element manufactured in Example 6. FIG. 11 shows luminance-current efficiency characteristics of the light-emitting element manufactured in Example 6. The figure which shows the triplet excitation energy of the aromatic amine compound of this invention. Shows a ^2-1 H NMR chart of (4- {N- [4- (carbazol-9-yl) phenyl] -N- phenylamino} phenyl) -5-phenyl-1,3,4-oxadiazole . 9 shows ¹ H NMR charts of (4- {N- [4- (carbazol-9-yl) phenyl] -N- phenylamino} phenyl) -10-phenylanthracene. 9- [4- (N- carbazolyl)] shows ¹ H NMR charts of the phenyl-10-phenyl anthracene. FIG. 6 shows a ¹ H NMR chart of 4- (carbazol-9-yl) phenyl-3′-phenyltriphenylamine (abbreviation: mYGA1BP). FIG. 9 shows an absorption spectrum of a toluene solution of 4- (carbazol-9-yl) phenyl-3′-phenyltriphenylamine (abbreviation: mYGA1BP). FIG. 9 shows an absorption spectrum of a thin film of 4- (carbazol-9-yl) phenyl-3′-phenyltriphenylamine (abbreviation: mYGA1BP). FIG. 11 shows an emission spectrum of a toluene solution of 4- (carbazol-9-yl) phenyl-3′-phenyltriphenylamine (abbreviation: mYGA1BP). FIG. 9 shows an emission spectrum of a thin film of 4- (carbazol-9-yl) phenyl-3′-phenyltriphenylamine (abbreviation: mYGA1BP). FIG. 6 shows a ¹ H NMR chart of 4- (carbazol-9-yl) phenyl-2′-phenyltriphenylamine (abbreviation: oYGA1BP). FIG. 9 shows an absorption spectrum of a toluene solution of 4- (carbazol-9-yl) phenyl-2′-phenyltriphenylamine (abbreviation: oYGA1BP). FIG. 9 shows an absorption spectrum of a thin film of 4- (carbazol-9-yl) phenyl-2′-phenyltriphenylamine (abbreviation: oYGA1BP). FIG. 9 shows an emission spectrum of a toluene solution of 4- (carbazol-9-yl) phenyl-2′-phenyltriphenylamine (abbreviation: oYGA1BP). FIG. 9 shows an emission spectrum of a thin film of 4- (carbazol-9-yl) phenyl-2′-phenyltriphenylamine (abbreviation: oYGA1BP). ¹ shows a ¹ H NMR chart of N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-di (1-naphthyl) biphenyl-4,4′-diamine (abbreviation: YGNBP). Figure. ¹³ shows a ¹³ C NMR chart of N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-di (1-naphthyl) biphenyl-4,4′-diamine (abbreviation: YGNBP). Figure. FIG. 9 shows an absorption spectrum of N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-di (1-naphthyl) biphenyl-4,4′-diamine (abbreviation: YGNBP). FIG. 9 shows an emission spectrum of N, N′-bis [4- (carbazol-9-yl) phenyl] -N, N′-di (1-naphthyl) biphenyl-4,4′-diamine (abbreviation: YGNBP). 9- (4-bromo-1-naphthyl) shows ¹ H NMR charts of carbazole. FIG. 6 shows a ¹ H NMR chart of N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-diphenylbiphenyl-4,4′-diamine (abbreviation: CNABP). FIG. 9 shows an absorption spectrum of N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-diphenylbiphenyl-4,4′-diamine (abbreviation: CNABP). FIG. 13 shows an emission spectrum of N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-diphenylbiphenyl-4,4′-diamine (abbreviation: CNABP). ¹ H NMR chart of N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-di-1-naphthylbiphenyl-4,4′-diamine (abbreviation: CNNBP) FIG. The absorption spectrum of N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-di-1-naphthylbiphenyl-4,4′-diamine (abbreviation: CNNBP) is shown. Figure. The emission spectrum of N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-di-1-naphthylbiphenyl-4,4′-diamine (abbreviation: CNNBP) is shown. Figure. FIG. 20 illustrates a light-emitting element of Example 12. FIG. 14 shows current density-luminance characteristics of the light-emitting element manufactured in Example 12. FIG. 16 shows voltage-luminance characteristics of the light-emitting element manufactured in Example 12. FIG. 16 shows luminance-current efficiency characteristics of the light-emitting element manufactured in Example 12. FIG. 10 shows an emission spectrum of the light-emitting element manufactured in Example 12. The figure which shows the DSC chart of N, N'-bis [4- (carbazol-9-yl) phenyl] -N, N'-di- (1-naphthyl) biphenyl-4,4'-diamine (abbreviation: YGNBP) . The figure which shows the DSC chart of N, N'-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N'-diphenylbiphenyl-4,4'-diamine (abbreviation: CNABP). 1 shows a DSC chart of N, N′-bis [4- (carbazol-9-yl) -1-naphthyl] -N, N′-di-1-naphthylbiphenyl-4,4′-diamine (abbreviation: CNNBP). Figure.

Explanation of symbols

101 Substrate 102 1st electrode 103 1st layer 104 2nd layer 105 3rd layer 106 4th layer 107 2nd electrode 302 1st electrode 303 1st layer 304 2nd layer 305 3rd Layer 306 fourth layer 307 second electrode 501 first electrode 502 second electrode 511 first light emitting unit 512 second light emitting unit 513 charge generation layer 601 source side driving circuit 602 pixel portion 603 gate side driving Circuit 604 Sealing substrate 605 Sealing material 607 Space 608 Wiring 609 FPC (flexible printed circuit)
610 Element substrate 611 TFT for switching
612 Current control TFT
613 First electrode 614 Insulator 616 Layer containing light emitting substance 617 Second electrode 618 Light emitting element 623 n-channel TFT
624 p-channel TFT
901 Case 902 Liquid crystal layer 903 Backlight 904 Case 905 Driver IC
906 Terminal 951 Substrate 952 Electrode 953 Insulating layer 954 Partition layer 955 Layer containing light emitting material 956 Electrode 2001 Housing 2002 Light source 2101 Glass substrate 2102 First electrode 2103 Layer containing composite material 2104 Hole transport layer 2105 Light emitting layer 2106 Electron transport Layer 2107 Electron injection layer 2108 Second electrode 2201 Glass substrate 2202 First electrode 2203 Layer 2304 containing a composite material Hole transport layer 2205 Light emitting layer 2206a First electron transport layer 2206b Second electron transport layer 2207 Electron injection layer 2208 Second electrode 3001 Lighting device 3002 Television device 9101 Housing 9102 Support base 9103 Display unit 9104 Speaker unit 9105 Video input terminal 9201 Main body 9202 Housing 9203 Display unit 9204 Keyboard 9205 External connection port 9206 Input device 9401 main body 9402 housing 9403 display unit 9404 audio input unit 9405 audio output unit 9406 operation key 9407 external connection port 9408 antenna 9501 main body 9502 display unit 9503 case 9504 external connection port 9505 remote control receiving unit 9506 image receiving unit 9507 battery 9508 Voice input unit 9509 Operation key 9510 Eyepiece unit

Claims (3)

An aromatic amine compound represented by the general formula (2).

(Wherein R ¹ and R ² each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 25 carbon atoms, and A ¹ represents a structural formula (14- 2), Ar ¹ represents a substituent represented by the structural formula (15-1) , and α represents a substituent represented by the general formula (2-2). In the general formula (2-2), R ^{61 to} R ⁶⁸ each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.) An aromatic amine compound represented by the structural formula (115).
An aromatic amine compound represented by the structural formula (120).