JP5220429B2 - NOVEL DIPYLENE DERIVATIVE, ELECTRON TRANSPORT MATERIAL, LIGHT EMITTING MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE CONTAINING THE SAME - Google Patents

Description

  The present invention relates to a novel dipyrene derivative, an electron transport material comprising the same, a light emitting material, and an organic electroluminescent device including the same.

  Organic electroluminescence was developed in the 1960s by M.C. First, Pope et al. Observed light emission from anthracene by attaching an electrode with a silver paste to an anthracene single crystal having a thickness of 10 to 20 μm and applying a direct current of about 400 V (Non-patent Document 1). However, at this time, sufficient carrier injection was not possible, and the light emission was only weak. Thereafter, an attempt was made to improve the film formability by taking out planar light emission by reducing the injection type electroluminescence into an organic thin film, lowering the driving voltage.

1987 Kodak's C.I. W. Tang et al. Used an aluminum complex using 8-quinolinol as a ligand, which has been used as a reagent for quantitative analysis of metals in the field of analytical chemistry, as an electron transporting luminescent material, and TAPC, a triphenyldiamine derivative. Used as a hole-transporting material, by laminating an ultra-thin film of 1000 mm or less on a transparent electrode by a vacuum deposition method, green emission luminance of 1000 cd / m ² or more with a DC voltage drive of 10 V or less, luminous efficiency 1.5 lm / W A function-separated stacked organic electroluminescence device that exhibits planar light emission with practical characteristics has been reported (Non-Patent Document 2).
Following this, Adachi et al. Classified the potential characteristics of organic materials (potential characteristics of more electron transport or hole transport) due to the systematic difference in the behavior of the injection current of organic thin films. And it proposed that the structure of the organic electroluminescent element to be used needs to be changed by the property (nonpatent literatures 3 and 4).

There are two types of organic materials used for organic electroluminescence devices: low molecular materials and high molecular materials. In particular, the development of low molecular materials is remarkable. Examples of materials used for low molecules include hole transport materials and electron transport materials, organometallic complexes used for light-emitting layers, and fluorescent dyes used as dopants.
Most of the hole transport materials have an arylamine structure, and TPD (N, N′-ditolyl-N, N′-diphenyl-1), which is a tetraphenyldiamine derivative, is used as an organic electroluminescence device. , 1′-biphenyl), but the glass transition temperature (Tg) is as low as 63 ° C., which has a problem in heat resistance and causes deterioration of the device. In order to solve this problem, α-NPD [N, N′-di (1-naphthyl) -N, N′-diphenyl-1] having a Tg as high as 95 ° C. by introducing a naphthyl group to increase steric hindrance. , 1'-biphenyl] has been proposed and has been widely used.
At present, starburst type arylamines (Non-patent Documents 5 and 6) and spiro compounds (Hypertransport materials having a high Tg exceeding 100 ° C. having a rigid functional group or skeleton having a larger steric hindrance) Many non-patent documents 7) have been synthesized.

Regarding electron transport materials, in addition to organometallic complexes such as Alq ₃ , many oxadiazole derivatives (Non-Patent Documents 3 and 4), triazole derivatives (Non-Patent Document 8) and the like have been reported.
These compounds are suitable as electron transport materials because of their high ionization potential and high hole blocking effect. However, some compounds form intermolecular complexes with organic compounds in the light-emitting layer, and the original light-emitting color of the light-emitting layer cannot be obtained. Can be seen. Therefore, it was necessary to improve the electron transport material to prevent such complex formation.

W. Helfrich, W.H. G. Schneider Phys. Rev. Lett. , 14 229 (1965) C. W. Tang, Van Slyke Appl. Phys. Lett. , 55 931 (1987) C. Adachi, T .; Tsutsui and S.T. Saito Appl. Phys. Lett. , 55 1489 (1989) C. Adachi, T .; Tsutsui and S.T. Saito Appl. Phys. Lett. , 57 531 (1990) Y. Shirota, T .; Kobata and N.K. Noma, Chem. Lett. , 1145 (1989) Y. Kuwabara, H .; Ogawa, H .; Inada, N.A. Noma and Y.M. Shirota Adv. Mater. , 6 677 (1994) J. et al. Salbeck, N.M. Yu, J .; Bauer, F.A. Weissortel and H.M. Bestgen Synth. Met. , 91 209 (1997) J. et al. Kido M.M. Kimura and K.K. Nagai Science 267 1332 (1995)

  An object of the present invention is to provide a novel dipyrene derivative, an electron transport material comprising the same, a light emitting material, and an organic electroluminescence device including the same.

The first of the present invention is the following general formula (1)
(Where Q is
R ^{1 to} R ⁹ are groups selected from the group consisting of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, and the number of carbon atoms R ¹⁰ to R ²⁰ are groups independently selected from the group consisting of 1 to 6 linear or branched alkylamino groups, and R ¹⁰ to R ²⁰ are each selected from hydrogen and a linear or branched alkyl group having 1 to 6 carbon atoms. Each group is independently selected from the group
It is related with the dipyrene derivative shown by these.
The second of the present invention relates to an electron transport material comprising the dipylene derivative according to claim 1.
A third aspect of the present invention relates to a light emitting material comprising the dipylene derivative according to claim 1.
4th of this invention is related with the organic electroluminescent element containing the dipyrene derivative of Claim 1.
5th of this invention is related with the organic electroluminescent element which used the dipyrene derivative | guide_body of Claim 1 for the electron carrying layer.
6th of this invention is related with the organic electroluminescent element which used the dipyrene derivative of Claim 1 for the light emitting layer.

Examples of the linear or branched alkyl group having 1 to 6 carbon atoms in R ^{1 to} R ⁹ and R ¹⁰ to R ²⁰ in the present invention include methyl, ethyl, n-propyl, iso-propyl, n-butyl, and iso-butyl. , Sec-butyl, tert-butyl, n-pentyl, iso-pentyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2,2-dimethylbutyl, Examples include 2,3-dimethylbutyl and 3,3-dimethylbutyl.

The linear or branched alkoxy group having 1 to 6 carbon atoms in R ^{1 to} R ⁹ in the present invention is a type in which hydrogen of —OH is substituted with the alkyl group, and the linear chain having 1 to 6 carbon atoms. Alternatively, the alkylamino group having a branched alkyl group is a type in which part or all of the hydrogen of —NH ₂ is substituted with the alkyl group.

The compound of the present invention can be produced by the following reaction.
In the above formula, Q is
R ^{1 to} R ⁹ are groups selected from the group consisting of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, and the number of carbon atoms R ¹⁰ to R ²⁰ are groups independently selected from the group consisting of 1 to 6 linear or branched alkylamino groups, and R ¹⁰ to R ²⁰ are each selected from hydrogen and a linear or branched alkyl group having 1 to 6 carbon atoms. X is halogen, Pd ₂ (dba) ₃ is tris (dibenzylideneacetone) dipalladium represented by the following formula, and PCy ₃ is tricyclophosphine. .

Specific examples of the compound of the present invention are illustrated below.

The novel dipylene derivative of the present invention has high electron transport performance. Therefore, it can be used as an electron transport material. Further, since it has a pyrene skeleton, it can also be used as a light emitting material.
When the novel dipyrene derivative of the present invention is used for organic electroluminescence, it can be used in combination with a suitable light emitting material.
When the novel dipyrene derivative of the present invention is used for an electron transport layer, the compound of the present invention can be used as an electron transport material. It can also be used in combination with other electron transport materials.
When the novel dipyrene derivative of the present invention is used for a light emitting layer, the compound of the present invention can be used as a light emitting material. It can also be used in combination with other light emitting materials.

  Next, the organic electroluminescence element of the present invention will be described. The organic EL device of the present invention is a device in which a single layer or a multilayer organic compound is laminated between an anode and a cathode, and at least one layer of the organic compound layer contains the dipyrene derivative of the present invention. When the organic EL element is a single layer, a light emitting layer is provided between the anode and the cathode. The light-emitting layer contains the light-emitting material, and in addition to that, the compound of the present invention or the existing hole transport material or electron transport material is used for transporting holes injected from the anode or electrons injected from the cathode to the light-emitting material. It may contain. Examples of the configuration of the multilayer organic EL element include an anode (for example, ITO) / hole transport layer / light emitting layer / electron transport layer / cathode, anode (ITO) / hole transport layer / light emitting layer / electron transport layer / electron injection layer. / Cathode, anode (ITO) / Hole transport layer / light emitting layer / hole block layer / electron transport layer / cathode, anode (ITO) / hole transport layer / light emitting layer / hole block layer / electron transport layer / electron injection layer / cathode And those laminated in a multilayer structure such as anode (ITO) / hole injection layer / hole transport layer / light emitting layer / hole block layer / electron transport layer / electron injection layer / cathode. Moreover, you may have a sealing layer on a cathode as needed. The organic electroluminescence device of the present invention is preferably supported on a substrate.

Each of the hole transport layer, the electron transport layer, and the light emitting layer may have a single layer structure or a multilayer structure. In addition, the hole transport layer and the electron transport layer should be provided separately with a layer responsible for the injection function (hole injection layer and electron injection layer) and a layer responsible for the transport function (hole transport layer and electron transport layer). You can also.
The organic electroluminescence element of the present invention is not limited to the above configuration example, and can have various configurations. If necessary, a layer in which a hole transport component and a light emitting layer component or an electron transport layer component and a light emitting layer component are mixed may be provided.

Hereinafter, the constituent elements of the organic electroluminescence element of the present invention will be described by taking as an example an element structure composed of ITO (anode) / hole (hole) transport layer / light emitting layer / electron transport layer / cathode.
There is no restriction | limiting in particular about the raw material of a board | substrate, What is necessary is just used conventionally for the conventional organic electroluminescent element, For example, what consists of glass, quartz glass, a transparent plastic etc. can be used.

As an anode of the organic electroluminescence device of the present invention, an electrode material may be a single metal having a high work function (4 eV or more), an alloy of metals having a high work function (4 eV or more), a conductive substance, or a mixture thereof. preferable. Specific examples of such electrode materials include metals such as gold, silver, and copper, conductive transparent materials such as ITO (indium-tin oxide), tin oxide (SnO ₂ ), and zinc oxide (ZnO), polypyrrole, and polythiophene. Examples thereof include conductive polymer materials such as For the anode, these electrode materials can be formed by a method such as vapor deposition, sputtering, or coating. The sheet electrical resistance of the anode is preferably several hundred Ω / cm ² or less. The thickness of the anode depends on the material, but is generally about 5 to 1,000 nm, preferably 10 to 500 nm.

As the cathode, an electrode material is preferably a single metal having a low work function (4 eV or less), an alloy of small work functions (4 eV or less), a conductive substance, or a mixture thereof. Specific examples of such electrode materials include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, magnesium, magnesium-silver alloy, magnesium-indium alloy, aluminum, aluminum-lithium alloy, and aluminum-magnesium alloy. Can be mentioned. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet electrical resistance of the cathode is preferably several hundred Ω / cm ² or less. The thickness of the cathode depends on the material, but is generally about 5 to 1,000 nm, preferably 10 to 500 nm. In order to efficiently extract light emitted from the organic EL device of the present invention, at least one of the anode and the cathode is preferably transparent or translucent.

The hole transport layer of the organic electroluminescence device of the present invention is made of a hole transfer compound and has a function of transferring holes injected from the anode to the light emitting layer. A hole transport material having a hole mobility of at least 10 ⁻⁶ cm ² / V · sec when a hole transport compound is disposed between two electrodes to which an electric field is applied and holes are injected from an anode Is preferred. The hole transport material used for the hole transport layer of the organic electroluminescence device of the present invention is not particularly limited as long as it has the above-mentioned preferable performance. Any one of materials conventionally used as a hole charge injection material in a photoconductive material or a known material used for a hole transport layer of an organic electroluminescence element can be selected and used. .

  Examples of the hole transport material include phthalocyanine derivatives such as copper phthalocyanine, N, N, N ′, N′-tetraphenyl-1,4-phenylenediamine, and N, N′-di (m-tolyl) -N. , N′-diphenyl-4,4-diaminophenyl (TPD), N, N′-di (1-naphthyl) -N, N′-diphenyl-4,4-diaminophenyl (α-NPD), etc. Examples thereof include amine derivatives, polyphenylenediamine derivatives, polythiophene derivatives, and water-soluble PEDOT-PSS (polyethylenedioxathiophene-polystyrenesulfonic acid). The hole transport layer may be composed of one or more of these other hole transport compounds, and a hole transport layer composed of a compound different from the hole transport material is laminated. Things can be used.

Examples of the hole injection material include PEDOT-PSS (polymer mixture) and DNTPD represented by the following chemical formula. n indicates that a large number of polymer basic chains exist.
Examples of the hole transport material include TPD, DTASi, α-NPD, and the like represented by the following chemical formula.

The dipyrene derivative of the present invention can be used for the light emitting layer of the organic electroluminescence device of the present invention. Moreover, there is no restriction | limiting in particular also about the conventionally well-known material, Arbitrary things can be selected and used.
Examples of the light-emitting material include perylene derivatives, naphthacene derivatives, quinacridone derivatives, coumarin derivatives (eg, coumarin 1, coumarin 540, coumarin 545), pyran derivatives (eg, DCM-1, DCM-2, DCJTB, etc.), organometallic complexes, eg, tris. Fluorescent materials such as (8-hydroxyquinolinolato) aluminum complex (Alq ₃ ) and tris (4-methyl-8-hydroxyquinolinolato) aluminum complex (Almq ₃ ) and [2- (4,6-difluorophenyl) Pyridyl-N, C2 ′] iridium (III) picolylate (FIrpic), tris {1- [4- (trifluoromethyl) phenyl] -1H-pyrazolate-N, C2 ′} iridium (III) (Irtfmpppz ₃ ), bis [2- (4 ′, 6′-difluorophenyl) pyridina -N, C2 '] iridium (III) tetrakis (1-pyrazolyl) borate (FIr6), tris (2-phenylpyridinato) iridium (III) (Irppy ₃₎ and the like phosphorescent material such as.

  The light-emitting layer can also be formed of a host material and a guest material (dopant) [Appl. Phys. Lett. , 65 3610 (1989)]. In particular, when a phosphorescent material is used for the light emitting layer, it is necessary to use a host material. As the host material used at this time, 4,4′-di (N-carbazolyl) -1,1′-biphenyl (CBP) ), 1,4-di (N-carbazolyl) benzene-2,2′-di [4 ″-(N-carbazolyl) phenyl] -1,1′-biphenyl (4CzPBP) and the like.

The guest material is preferably 0.01 to 40% by weight, more preferably 0.1 to 20% by weight with respect to the host material. Examples of guest materials include conventionally known FIrpic, Irppy ₃ , FIr 6 and the like shown below.

  As a material for the electron transport layer of the organic electroluminescence device of the present invention, the novel dipyrene derivative of the present invention is preferable. Although this thing can be used independently, you may use together with another electron transport material.

  In the organic electroluminescence device of the present invention, an electron injection layer composed of a conductor may be further provided between the cathode and the organic layer for the purpose of further improving the electron injection property. As the conductor used here, it is preferable to use at least one metal compound selected from alkali metal halides, alkaline earth metal halides, and alkali metal organic complexes. Examples of the alkali metal halide include lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, and lithium chloride. Examples of the alkaline earth metal halide include magnesium fluoride, calcium fluoride, barium fluoride, and strontium fluoride. Examples of the alkali metal organic complex include 8-hydroxyquinolinolatolithium and 8-hydroxyquinolinolatocesium.

The method for forming the hole transport layer and the light emitting layer is not particularly limited. For example, a dry film forming method (for example, a vacuum vapor deposition method, an ionization vapor deposition method) or a wet film forming method [a solvent coating method (for example, a spin coating method, a casting method, an ink jet method, etc.)] can be used. The novel dipyrene derivative of the present invention is preferably a dry film forming method (for example, a vacuum deposition method, an ionization deposition method, etc.). The film formation of the electron transport layer is limited to a dry film formation method (for example, a vacuum vapor deposition method, an ionization vapor deposition method, etc.) because the lower layer may be eluted when the wet film formation method is used. For the production of the element, the above film forming method may be used in combination.
When forming each layer such as a hole transport layer, a light emitting layer, and an electron transport layer by a vacuum deposition method, the vacuum deposition conditions are not particularly limited. Usually, under a vacuum of about 10 ⁻⁵ Torr or less, a boat temperature (deposition source temperature) of about 50 to 500 ° C., a substrate temperature of about −50 to 300 ° C., and 0.01 to 50 nm / sec. Vapor deposition is preferred. When forming each layer of a positive hole transport layer, a light emitting layer, and an electron carrying layer using a some compound, it is preferable to co-evaporate the boat which put the compound, respectively controlling temperature.

  When forming the hole transport layer and the light emitting layer by a solvent coating method, the components constituting each layer are dissolved or dispersed in a solvent to obtain a coating solution. Solvents include hydrocarbon solvents (eg, heptane, toluene, xylene, cyclohexane, etc.), ketone solvents (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), halogen solvents (eg, dichloromethane, chloroform, chlorobenzene, dichlorobenzene, etc.) Ester solvents (eg, ethyl acetate, butyl acetate, etc.), alcohol solvents (eg, methanol, ethanol, butanol, methyl cellosolve, ethyl cellosolve, etc.), ether solvents (eg, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1 , 2-dimethoxyethane, etc.), aprotic solvents (eg, N, N′-dimethylacetamide, dimethyl sulfoxide, etc.), water and the like. The solvent may be used alone, or a plurality of solvents may be used in combination.

The thickness of each layer such as the hole transport layer, the light emitting layer, and the electron transport layer is not particularly limited, but is usually 5 to 5,000 nm.
The organic electroluminescence device of the present invention can be protected by providing a protective layer (sealing layer) for the purpose of blocking contact with oxygen, moisture, etc., or by enclosing the device in an inert material. Examples of the inert substance include paraffin, silicon oil, and fluorocarbon. Examples of the material used for the protective layer include fluororesin, epoxy resin, silicone resin, polyester, polycarbonate, and photocurable resin.

  The organic electroluminescence device of the present invention can be used as a normal DC drive device. When a DC voltage is applied, light emission is usually observed when about 1.5 to 20 V is applied with the positive polarity of the anode and the negative polarity of the cathode. The organic electroluminescence device of the present invention can also be used as an AC drive device. When an AC voltage is applied, light is emitted when the anode is in a positive state and the cathode is in a negative state. The organic electroluminescence device of the present invention includes, for example, a flat light emitter such as an electrophotographic photosensitive member and a flat panel display, a copying machine, a printer, a backlight of a liquid crystal display, a light source such as an instrument, various light emitting devices, various display devices, and various signs. It can be used for various sensors and various accessories.

48 to 61 show preferred examples of the organic electroluminescence element of the present invention.
FIG. 48 is a cross-sectional view showing an example of the organic electroluminescence element of the present invention. FIG. 48 shows a configuration in which an anode 2, a light emitting layer 3 and a cathode 4 are sequentially provided on a substrate 1. The light-emitting material used here is useful when it has a single hole-transporting property, electron-transporting property, and light-emitting function, or a mixture of compounds having the respective functions. The compound of the present invention can be used for the light emitting layer 3.

  FIG. 49 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 49 shows a configuration in which an anode 2, a hole transport layer 5, a light emitting layer 3, and a cathode 4 are sequentially provided on a substrate 1. In this case, the light emitting layer is useful when it has an electron transporting function, and the compound of the present invention can be used for the light emitting layer 3.

  FIG. 50 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 50 shows a structure in which an anode 2, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. In this case, the light emitting layer is useful when it has a hole transporting function, and the compound of the present invention can be used for the light emitting layer 3.

  FIG. 51 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 51 shows a structure in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. This is a separation of the functions of carrier transport and light emission, and the degree of freedom in material selection increases, so that the efficiency of light emission and the degree of freedom in light emission color increase. The compound of this invention can be used for a light emitting layer or an electron carrying layer.

  FIG. 52 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 52 shows a structure in which an anode 2, a hole injection layer 7, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6 and a cathode 4 are sequentially provided on a substrate 1. In this case, the provision of the hole injection layer 7 improves the adhesion between the anode 2 and the hole transport layer 5, improves the injection of holes from the anode, and is effective in lowering the voltage of the light emitting element. The compound of this invention can be used for a light emitting layer or an electron carrying layer.

  FIG. 53 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 53 shows a configuration in which an anode 2, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4 are sequentially provided on a substrate 1. In this case, injection of electrons from the cathode 4 is improved, which is effective for lowering the voltage of the light emitting element. The compound of this invention can be used for a light emitting layer or an electron carrying layer.

  FIG. 54 is a cross-sectional view showing another example of the organic electroluminescence element of the present invention. FIG. 54 shows a configuration in which an anode 2, a hole injection layer 7, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4 are sequentially provided on a substrate 1. In this case, the injection of holes from the anode 2 is improved and the injection of electrons from the cathode 4 is improved, which is the most effective for driving at a low voltage. The compound of this invention can be used for a light emitting layer or an electron carrying layer.

  55 to 61 are sectional views of a device in which a hole blocking layer is inserted. The hole blocking layer has an effect of preventing holes injected from the anode or excitons generated by recombination in the light emitting layer 3 from escaping to the cathode 4, thereby improving the light emission efficiency of the organic electroluminescence device. effective. The hole blocking layer 9 can be inserted between the light emitting layer 3 and the cathode 4, between the light emitting layer 3 and the electron transport layer 6, or between the light emitting layer 3 and the electron injection layer 8. More preferred is between the light emitting layer 3 and the electron transport layer 6.

55 to 61, each of the hole transport layer 5, the hole injection layer 7, the electron transport layer 6, the electron injection layer 8, the light emitting layer 3, and the hole blocking layer 9 has a single layer structure, but is a multilayer. It may be a structure.
48 to 61 show basic element configurations to the last, and the compound of the present invention can be used for a light emitting layer and an electron transport layer. The structure of the organic electroluminescent element using the compound of the present invention is not limited to this.

Examples of the electron injecting material used for the electron injecting layer include known compounds as well as compounds according to Japanese Patent Application No. 2006-292032 of the applicant, for example, the following compound group.

The novel dipyrene derivative of the present invention has a very large electron transport ability as compared with a conventional electron transport layer such as Alq ₃ . In addition, the mobility is large and the carrier balance with the holes in the element is excellent. In addition, when used as a light emitting material, it exhibits light emission from blue to green and is suitable as a full color or white material for the device, so that the novel dipyrene derivative of the present invention is extremely important industrially.

  Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited thereto.

Example 1
Synthesis of 3,8-di (1-pyrenyl) -1,10-phenanthroline (abbreviation DPpyre-Phen)
Pyrene-1-boric acid (PyrebAc) (6.75 mmol, 1.66 g) and 3,8-dibromo-1,10-phenanthroline (DBPhen) (3.07 mmol, 1.06 g) were added to 1,4-dioxane (100 ml). ), Potassium phosphate (9.21 mmol) and ion-exchanged water (7.5 ml) were added, and nitrogen bubbling was performed for 1 hour. Thereafter, tricyclophosphine [PCy ₃ ] (0.13 mmol:% in the formula is% relative to pyrene-1-boric acid) and tris (dibenzylideneacetone) dipalladium [Pd ₂ (dba) ₃ ] (0 0.06 mmol:% in the formula is% relative to pyrene-1-boric acid), and reacted at 100 ° C. for 16 hours under a nitrogen stream. After completion of the reaction, 1,4-dioxane was removed with an evaporator, extracted with chloroform, washed with ion-exchanged water and saturated saline, and the solvent was removed with an evaporator. Purification was performed by column chromatography (chloroform: methanol = 100: 1), followed by recrystallization (chloroform: n-hexane = 2: 1) and sublimation purification to obtain a yellow powder. Identification was performed by ¹ H-NMR spectrum and Mass spectrum. (Yield 0.82g, Yield 46%)
Table 1 shows the melting point (Tm), glass transition temperature (Tg) and decomposition temperature (Td) of the compound of Example 1.
As for Tm (melting point), an endothermic curve appears when a sample is added to DSC (Differential Scanning Calorimeter) and the temperature is raised, and the temperature at the maximum is read and Tm is defined as Tm.
As for Tg (glass transition temperature), a sample is added to DSC, the melted material is rapidly cooled, and if it is repeated 2 to 3 times, a curve representing the glass transition appears on the chart. The intersection is adopted as Tg.
When Td (decomposition temperature) is heated by adding a sample to DTA (Differential Thermal Analyzer), it decomposes by the heat of the sample and begins to decrease in weight. Read the temperature at which the phenomenon started, and let that temperature be Td.
FIG. 1 shows the DSC curve of the melting point before high vacuum sublimation purification, FIG. 2 shows an enlarged view of the third measurement, FIG. 3 shows the DSC curve of the melting point after high vacuum sublimation purification, and FIG. Shown in The ¹ H-NMR spectrum (using internal standard tetramethylsilane in a deuterated chloroform solvent, 400 MHz) (all regions) of this product is shown in FIG. 5, its enlarged view (7 to 10 ppm) is shown in FIG. 6, and the Mass spectrum is shown in FIG. .

Example 2
Synthesis of 3,5-di (1-pyrenyl) -pyridine (abbreviation 35PYREPY)
3,5-dibromopyridine (35DBPY) (4.0 mmol, 0.9 g) and pyrene-1-boric acid (PyrebAc) (8.8 mmol, 2.2 g) were dissolved in toluene (80 ml) / ethanol (40 ml). Potassium carbonate (24 mmol) and ion-exchanged water (12 ml) were added, and nitrogen bubbling was performed for 1 hour. Then, tetrakis (triphenylphosphine) palladium [Pd (ph ₃ P) ₄ ] (0.4 mmol) was added and reacted at 80 ° C. for 12 hours under a nitrogen stream. After completion of the reaction, chloroform was added to the reaction solution and stirred. Then, it extracted with toluene and wash | cleaned with ion-exchange water and a saturated salt solution. Then, after drying with anhydrous magnesium sulfate, the solvent was removed by an evaporator. Purification was performed by column chromatography (chloroform), followed by sublimation purification to obtain yellow crystals. Identification was performed by ¹ H-NMR spectrum and elemental analysis (yield 1.54 g, yield 80%).
Table 2 shows the results of elemental analysis of this product. In addition, ultraviolet-visible absorption spectrum (UV), excitation light spectrum (λex) and photoluminescence emission spectrum (λem) in chloroform (concentration 1 × 10 ⁻⁵ mol / l) and ultraviolet-film in a thin film (Film) form. Table 3 shows the visible absorption spectrum (UV), excitation light spectrum (λex), and photoluminescence emission spectrum (λem).
The ultraviolet-visible absorption spectrum of this product is shown in FIG. 8, and the excitation spectrum and emission spectrum are shown in FIG. Further, a ¹ H-NMR spectrum (using an internal standard tetramethylsilane in deuterated chloroform solvent, 400 MHz) (all regions) is shown in FIG. 10, and an enlarged view (7 to 10 ppm) is shown in FIG.
The error is represented by-when the measured value is smaller than the theoretical value.
λmax represents the maximum.

Example 3
Synthesis of 2,6-di (1-pyrenyl) -pyridine (abbreviation 26PYREPY)
2,6-dibromopyridine (26DBPY) (4.0 mmol, 0.9 g) and pyrene-1-boric acid (PyrebAc) (8.8 mmol, 2.2 g) were dissolved in toluene (80 ml) / ethanol (40 ml). Potassium carbonate (24 mmol) and ion-exchanged water (12 ml) were added, and nitrogen bubbling was performed for 1 hour. Then, tetrakis (triphenylphosphine) palladium (0.4 mmol) was added and reacted at 80 ° C. for 12 hours under a nitrogen stream. After completion of the reaction, chloroform was added to the reaction solution and stirred. Then, it extracted with toluene and wash | cleaned with ion-exchange water and a saturated salt solution. Then, after drying with anhydrous magnesium sulfate, the solvent was removed by an evaporator. Purification was performed by column chromatography (chloroform: hexane = 1: 1), followed by sublimation purification to obtain yellow crystals. Identification was performed by ¹ H-NMR spectrum and elemental analysis. (Yield 1.05 g, Yield 57%)
Table 4 shows the results of elemental analysis of this product. In addition, ultraviolet-visible absorption spectrum (UV), excitation light spectrum (λex) and photoluminescence emission spectrum (λem) in chloroform (concentration 1 × 10 ⁻⁵ mol / l) and ultraviolet-film in a thin film (Film) form. Table 5 shows the visible absorption spectrum (UV), excitation light spectrum (λex), and photoluminescence emission spectrum (λem).
The ultraviolet-visible absorption spectrum of this product is shown in FIG. 12, and the excitation spectrum and emission spectrum are shown in FIG. In addition, FIG. 14 shows a ¹ H-NMR spectrum (using an internal standard tetramethylsilane in deuterated chloroform solvent, 400 MHz) (all regions), and FIG. 15 shows an enlarged view (7 to 10 ppm).
The error is represented by-when the measured value is smaller than the theoretical value.
λmax represents the maximum.

Example 4
Synthesis of 4,6-di (1-pyrenyl) pyrimidine (abbreviation 46PYREPYM)
4,6-dichloropyrimidine (46DClPYM) (4.0 mmol, 0.4 g) and pyrene-1-boric acid (PyrebAc) (8.8 mmol, 2.2 g) were dissolved in acetonitrile (80 ml), and sodium carbonate (24 mmol) was dissolved. ) And ion-exchanged water (30 ml) were added, and nitrogen bubbling was performed for 1 hour. Then, bis (triphenylphosphine) palladium dichloride (0.16 mmol) was added and reacted at 60 ° C. for 12 hours under a nitrogen stream. After completion of the reaction, the reaction solution was filtered to collect the precipitate, and the precipitate was washed with ion-exchanged water and n-hexane. Thereafter, the solvent was removed with a vacuum dryer. Purification was performed by column chromatography (chloroform), followed by sublimation purification to obtain crystals. Identification was performed by ¹ H-MRN spectrum and elemental analysis. (Yield 0.27 g, yellow yield 14%)
Table 6 shows the results of elemental analysis of this product. In addition, ultraviolet-visible absorption spectrum (UV), excitation light spectrum (λex) and photoluminescence emission spectrum (λem) in chloroform (concentration 1 × 10 ⁻⁵ mol / l) and ultraviolet-film in the form of a thin film (film). Table 7 shows the visible absorption spectrum (UV), excitation light spectrum (λex), and photoluminescence emission spectrum (λem).
The ultraviolet-visible absorption spectrum of this product is shown in FIG. 16, and the excitation spectrum and emission spectrum are shown in FIG. In addition, FIG. 18 shows a ¹ H-NMR spectrum (using internal standard tetramethylsilane in deuterated chloroform solvent, 400 MHz) (all regions), and FIG. 19 shows an enlarged view (7 to 10 ppm).
The error is represented by-when the measured value is smaller than the theoretical value.
λmax represents the maximum.

Of 3,5-di (1-pyrenyl) -pyridine of Example 2, 2,6-di (1-pyrenyl) -pyridine of Example 3, 4,6-di (1-pyrenyl) pyrimidine of Example 4 Tm, Tg, and Td were measured to evaluate thermal characteristics. The results are shown in Table 8.
In addition, an ultraviolet-visible absorption spectrum, an emission spectrum and an ionization potential (AC-3) were measured to evaluate electrochemical characteristics. The results are shown in Table 9.
Ip: ionization potential Eg: energy gap Ea: energy affinity (electron affinity)
Regarding the energy gap (Eg), an absorption curve of the thin film prepared with a vapor deposition machine is measured with an ultraviolet-visible absorptiometer. A tangent line is drawn at the short-wavelength rising edge of the thin film, and the target wavelength is obtained by substituting the obtained wavelength W (nm) of the intersection into the following equation. The value obtained thereby becomes Eg.
Eg = 1240 ÷ W
For example, if the value W (nm) obtained by drawing a tangent is 470 nm, the value of Eg at this time is Eg = 1240 ÷ 470 = 2.63 (eV)
Would be said.
IP (ionization potential) is measured using an ionization potential measuring device (for example, Riken Keiki AC-3), and the value of the voltage (eV) at which the sample to be measured starts ionization is read.
Ea (electron affinity) is a value obtained by subtracting Eg from Ip.
Intensity au in this specification was measured at 4.2K in a cryostat using a streak camera manufactured by Hamamatsu Photonics.

Examples 5, 6, 7 and Comparative Example 1
As an electron transport material, 35PYREPY obtained in Example 2, 26PYREPY obtained in Example 3, 46PYREPYM obtained in Example 4 were used, and for comparison, an element having the following configuration using Alq ₃ was prepared. Performance was evaluated.
Device configuration comparison example 1
Device 1 (Δ): [ITO / NPD (40 nm) / Alq ₃ (60 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 5
Device 2 (●): [ITO / NPD (40 nm) / Alq ₃ (30 nm) / 35 PYREPY (30 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 6
Device 3 (◆): [ITO / NPD (40 nm) / Alq ₃ (30 nm) / 26 PYREPY (30 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 7
Device 4 (black triangle): [ITO / NPD (40 nm) / Alq ₃ (30 nm) / 46 PYREPYM (30 nm) / LiF (0.5 nm) / Al (100 nm)]
The electroluminescence (EL) spectra of these devices are shown in FIG.
The energy diagram is shown in FIG.
The current density-voltage characteristics are shown in FIGS.
Luminance-voltage characteristics are shown in FIG. 24. Luminous efficiency-voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The luminance-current density characteristics are shown in FIG.
Each is shown.
Although the vertical axis in FIG. 22 is a real number display, the current density in the low voltage portion is difficult to see, so the vertical axis is changed to a logarithmic display in FIG.
The electrochemical characteristics of the device are shown in Table 10.

Examples 8, 9, and 10 and Comparative Example 2
Using 35PYREPY obtained in Example 2 as an electron transport material, an element in which the thickness of the electron transport layer was changed to 40 nm, 30 nm, and 20 nm, and an element having the following configuration using Alq ₃ for comparison were prepared. Performance was evaluated.
Element configuration comparison example 2
Device 5 (Δ): [ITO / NPD (40 nm) / Alq ₃ (60 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 8
Device 6 (●): [ITO / NPD (40 nm) / Alq ₃ (20 nm) / 35 PYREPY (40 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 9
Device 7 (◆): [ITO / NPD (40 nm) / Alq ₃ (30 nm) / 35 PYREPY (30 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 10
Device 8 (black triangle): [ITO / NPD (40 nm) / Alq ₃ (40 nm) / 35 PYREPY (20 nm) / LiF (0.5 nm) / Al (100 nm)]
The electroluminescence (EL) spectra of these devices are shown in FIG.
The energy diagram is shown in FIG.
The current density-voltage characteristics are shown in FIGS.
Luminance-voltage characteristics are shown in FIG. 32. Luminous efficiency-voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The luminance-current density characteristics are shown in FIG.
Each is shown.
In addition, although the vertical axis | shaft of FIG. 30 is a real number display, since the current density of the part with a low voltage is hard to see, the vertical axis | shaft was changed into the logarithm display in FIG.
Table 11 shows the electrochemical characteristics of the device.

Examples 11, 12, 13 and Comparative Example 3
35PYREPY obtained in Example 2, 26PYREPY obtained in Example 3 and 46PYREPYM obtained in Example 4 were used as electron transporting and light-emitting materials, and an element having the following configuration using Alq ₃ was used for comparison. The performance was evaluated.
Device configuration comparison example 3
Device 9 (Δ): [ITO / NPD (40 nm) / Alq ₃ (60 nm) / LiF (0.5 nm) / Al (100 nm)]
Implementation 11
Device 10 (●): [ITO / NPD (40 nm) / 35 PYREPY (60 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 12
Device 11 (◆): [ITO / NPD (40 nm) / 26 PYREPY (60 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 13
Device 12 (black triangle): [ITO / NPD (40 nm) / 46 PYREPYM (60 nm) / LiF (0.5 nm) / Al (100 nm)]
The electroluminescence (EL) spectra of these devices are shown in FIG.
The current density-voltage characteristics are shown in FIGS.
Luminance-voltage characteristics are shown in FIG. 39. Luminous efficiency-voltage characteristics are shown in FIG.
The current efficiency vs. voltage characteristics are shown in FIG.
The luminance-current density characteristics are shown in FIG.
Each is shown.
Note that although the vertical axis in FIG. 37 is a real number display, the current density in the low voltage portion is difficult to see, so in FIG. 38 the vertical axis is changed to a logarithmic display.
Table 12 shows the electrochemical characteristics of the device.

Examples 14, 15, 16
Using 35 PYREPY obtained in Example 2, 26 PYREPY obtained in Example 3, and 46 PYREPYM obtained in Example 4, the fluorescence quantum yield in the vapor-deposited film of the dipyrene derivative was measured.
Using an organic EL quantum efficiency measurement device (C9920-01, manufactured by Hamamatsu Photonics), a single layer film formed by vacuum evaporation on a quartz substrate with a thickness of 50 nm is used to obtain an absolute emission quantum yield of the single layer film at an excitation wavelength of 325 nm. Was measured.
The measurement result is
1) Obtain the area of the absorption peak (mountain) at 325 nm of the blank quartz substrate.
2) The absorption peak (mountain) area of a single layer film on a quartz substrate at 325 nm is obtained.
3) Obtain the area of the peak (emission peak) newly formed from the measurement result of the single layer film on the quartz substrate.
4) The area obtained by subtracting 2) from 1) was spent to produce the area of the peak (luminescence peak) formed in 3).
From the values of 1) to 3), it can be obtained by the following equation.
Fluorescence quantum yield (%) = 3) area ÷ [1) area−2) area] × 100
The results are shown in Table 13. The measurement result of 35PYREPY is shown in FIG.
The measurement result of 26PYREPY is shown in FIG.
The measurement result of 46PYREPYM is shown in FIG.
Each is shown.
In addition, since quartz has no element that deactivates light, the incident light is directly converted into photons. Therefore, the photon efficiency of quartz is 0%. On the other hand, all of the light entering the organic thin film does not change to photons, and one part is inactivated by necessity, but the compound of the present invention has a low degree of inactivation.

Examples 17, 18, 19
Using 35 PYREPY obtained in Example 2, 26 PYREPY obtained in Example 3, and 46 PYREPYM obtained in Example 4, an electron-only device (Electron only device) was manufactured, and the ease of entering electrons was measured. An electron-only device is an element obtained by removing a hole transport (hole transport) layer from an organic electroluminescence element. In order to completely stop the entrance / exit of holes from the ITO, one hole block layer is provided on the ITO.
Example 17
Device 13 (●): [ITO / BCP (10 nm) / 35 PYREPY (100 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 18
Device 14 (◆): [ITO / BCP (10 nm) / 26 PYREPY (100 nm) / LiF (0.5 nm) / Al (100 nm)]
Example 19
Device 15 (black triangle): [ITO / BCP (10 nm) / 46 PYREPYM (100 nm) / LiF (0.5 nm) / Al (100 nm)]
The current density-voltage characteristics of these elements are shown in FIG.

Examples 20, 21, 22 and Comparative Example 4
In order to measure the electron mobility in the 35PYREPY obtained in Example 2, the 26PYREPY obtained in Example 3, and the 46PYREPYM obtained in Example 4, the following devices were prepared. For comparison, an Alq ₃ element was also produced in the same manner.
Example 20
Device 16 (●): [ITO / 35PYREPY (4 μm) / Al (100 nm)]
Example 21
Device 17 (◆): [ITO / 26PYREPY (4 μm) / Al (100 nm)]
Example 22
Device 18 (black triangle): [ITO / 46 PYREPYM (4 μm) / Al (100 nm)]
Comparative Example 4
Device 19: (Δ): [ITO / Alq ₃ (4 μm) / Al (100 nm)]
The mobility-electric field strength characteristics of these elements are shown in FIG.

Example 23
Synthesis of 2,5-di (pyren-1-yl) thiophene (abbreviation DPyreTh)
As shown in Table 14 below, 0.34 g of 2,5-dibromothiophene, 1.77 g of 1-pyreneboronic acid, 20 ml of toluene, 10 ml of ethanol, and an aqueous potassium carbonate solution (2M concentration) were added to a four-necked flask under a nitrogen stream. Nitrogen bubbling was performed for 4 hours. Then tetrakis (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ] 0. . 208 g was added and refluxed for 12 hours with stirring.
Dispersion washing was performed with chloroform, ion-exchanged water and saturated saline, and recrystallization was performed using toluene. Thereafter, rough purification was performed in a glass tube oven (GTO), followed by purification by sublimation. It was confirmed that the target product was synthesized by ¹ H-NMR / Mass spectra shown in FIGS. FIG. 63 is an enlarged view of FIG.
2,5-DBrTh = 2,5-dibromothiophene (2,5-Dibrothiophene)
PyreBAc = 1-pyreneboric acid
Pd (PPh ₃ ) ₄ = tetrakis (triphenylphosphine palladium) (0) [Tetrakis (triphenylphosphine) Palladium (0)]
FIG. 64 shows a mass spectrum of 2,5-di (pyren-1-yl) thiophene, and FIG. 65 shows one kind of melting curve showing its thermophysical evaluation.
The curve of (1) is a melting curve by the first heating using a differential scanning calorimeter (DSC) (Thermo plus EVO / DSC8230) of DPyTh,
The curve of (2) is a melting curve by the second heating,
The curve (3) is a melting curve by the third heating.
In the figure, the vertical axis is the amount of heat, and the horizontal axis is the temperature.
FIG. 66 shows a TGA (thermobalance), line (A) is a thermogravimetric decrease curve, and line (B) is a curve showing the heating state. The horizontal axis represents the temperature, the left vertical axis represents the degree of heating, and the right vertical axis represents the thermal weight reduction rate (corresponding to (i) above).
As seen from FIG. 66, the melting point, glass transition point, and decomposition temperature of 2,5-di (pyren-1-yl) thiophene are as shown in the following table.
FIG. 67 shows the evaluation of optical properties of 2,5-di (pyren-1-yl) thiophene. The results shown in FIG. 67 and Table 16 are the toluene solution of the compound (the concentration when measuring PL intensity is 1 × 10 ⁻⁷ mol / l, and the concentration when measuring UV intensity is 1 × 10 ⁻⁵ mol / l). l).
In FIG. 67, the vertical axis represents normalized PL intensity and UV intensity, and the horizontal axis represents wavelength.
FIG. 68 and Table 17 show a chloroform solution of 2,5-di (pyren-1-yl) thiophene (concentration when measuring PL intensity is 1 × 10 ⁻⁷ mol / l, and when measuring UV intensity. The optical property evaluation using a concentration of 1 × 10 ⁻⁵ mol / l) is shown.
The vertical axis in FIG. 68 shows the normalized PL intensity and UV intensity, and the horizontal axis is the wavelength.
FIG. 69 and Table 18 show the results of optical property evaluation using the film thickness (film thickness 622 nm) of 2,5-di (pyren-1-yl) thiophene.
FIG. 70 shows the photoluminescence intensity of 2,5-di (pyren-1-yl) thiophene in comparison with quartz.

Example 24
Using 2,5-di (pyren-1-yl) thiophene (DPyreTh) obtained in Example 23, an organic EL device having the following constitution was produced.
Device structure _{ITO / DPyreTh40nm / Alq 3 60nm /} LiF0.5nm / Al100nm
The fluorescence spectrum (EL spectrum) of this organic EL element is shown in FIG.
The current density-voltage characteristics are shown in FIG.
The luminance-voltage characteristics are shown in FIG.
The luminous efficiency-luminance characteristics are shown in FIG.
The current efficiency vs. luminance characteristics are shown in FIG.
FIG. 76 shows the luminance-current density characteristics.
Each is shown.
Also. The initial characteristics of the device are shown in Table 19 below.

Example 25
Using the DPyThh obtained in Example 23, an organic EL element having the following configuration was prepared.
Element configuration ITO / α-NPD 40 nm / Alq ₃ 30 nm / DPyTh 30 nm / LiF 0.5 nm / Al 100 nm
The fluorescence spectrum (EL spectrum) of this organic EL element is shown in FIG.
The current density-voltage characteristics are shown in FIG.
Fig. 79 shows the luminance-voltage characteristics.
The luminous efficiency-luminance characteristics are shown in FIG.
The current efficiency-luminance characteristics are shown in FIG.
The luminance-current density characteristics are shown in FIG.
Each is shown.
Also. The initial characteristics of the device are shown in Table 20 below.

The DSC curve of melting | fusing point before the high vacuum sublimation purification of 3,8- di (1-pyrenyl) -1,10-phenanthroline DPyre-Phen of Example 1 is shown. The enlarged view of the 3rd measurement of the DSC curve of FIG. 1 is shown. The DSC curve of melting | fusing point after the high vacuum sublimation refinement | purification of 3,8- di (1-pyrenyl) -1,10-phenanthroline DPyre-Phen of Example 1 is shown. The area surrounded by a circle represents a heat generation state, which is a phenomenon seen because the purity of this material has improved. The enlarged view of the 3rd measurement of the DSC curve of FIG. 3 is shown. 1 shows the ¹ H-NMR spectrum of 3,8-di (1-pyrenyl) -1,10-phenanthroline DPyre-Phen in Example 1 (using internal standard tetramethylsilane, 400 MHz in deuterated chloroform solvent) (all regions). . The ¹ H-NMR spectrum enlarged view (7-10 ppm) of FIG. 5 is shown. FIG. 7 shows the mass spectrum of 3,8-di (1-pyrenyl) -1,10-phenanthroline DPyre-Phen in Example 1. The ultraviolet-visible absorption spectrum measured in chloroform and the thin film form of 3,5-di (1-pyrenyl) -pyridine (35PYREPY) of Example 2 is shown. The excitation spectrum and emission spectrum of 3,5-di (1-pyrenyl) -pyridine (35PYREPY) of Example 2 measured in chloroform and in the form of a thin film are shown. 1 shows the ¹ H-NMR spectrum of 3,5-di (1-pyrenyl) -pyridine (35PYREPY) of Example 2 (using internal standard tetramethylsilane, 400 MHz in deuterated chloroform solvent) (all regions). The ¹ H-NMR spectrum enlarged view (7-10 ppm) of FIG. 10 is shown. The ultraviolet-visible absorption spectrum which measured the 2, 6- di (1-pyrenyl) -pyridine (26PYREPY) of Example 3 in chloroform and a thin film form, respectively is shown. The excitation spectrum and emission spectrum of 2,6-di (1-pyrenyl) -pyridine (26PYREPY) of Example 3 measured in chloroform and in the form of a thin film are shown. 1 shows the ¹ H-NMR spectrum of 2,6-di (1-pyrenyl) -pyridine (26PYREPY) of Example 3 (using internal standard tetramethylsilane, 400 MHz in deuterated chloroform solvent) (all regions). ¹ H-NMR spectrum enlarged view of FIG. 14 shows the (7~10ppm). The ultraviolet-visible absorption spectrum measured in chloroform and the thin film form of 4,6-di (1-pyrenyl) pyrimidine (46PYREPYM) of Example 4 is shown. The excitation spectrum and emission spectrum of 4,6-di (1-pyrenyl) pyrimidine (46PYREPYM) of Example 4 measured in chloroform and in the form of a thin film are shown. 1 shows the ¹ H-NMR spectrum of 4,6-di (1-pyrenyl) pyrimidine (46PYREPYM) in Example 4 (using internal standard tetramethylsilane, 400 MHz in deuterated chloroform solvent) (all regions). The enlarged view (7-10 ppm) of FIG. 18 is shown. The electroluminescence (EL) spectrum of Examples 5-7 and the organic electroluminescent element (organic EL element) of the comparative example 1 is shown. The energy diagram of the organic electroluminescent element (organic EL element) of Examples 5-7 and Comparative Example 1 is shown. The current density-voltage characteristic of the real number display of Examples 5-7 and the organic electroluminescent element (organic EL element) of Comparative Example 1 is shown. The current density-voltage characteristic of the semi logarithm display of the organic electroluminescent element (organic EL element) of Examples 5-7 and Comparative Example 1 is shown. The brightness | luminance-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 5-7 and Comparative Example 1 is shown. The luminous efficiency-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 5-7 and Comparative Example 1 is shown. The current efficiency-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 5 to 7 and Comparative Example 1 is shown. The brightness | luminance-current density characteristic of the organic electroluminescent element (organic EL element) of Examples 5-7 and Comparative Example 1 is shown. The electroluminescence (EL) spectrum of the organic electroluminescent element (organic EL element) of Examples 8 to 10 and Comparative Example 2 is shown. The energy diagram of the organic electroluminescent element (organic EL element) of Examples 8-10 and Comparative Example 2 is shown. The current density-voltage characteristic of the real number display of Examples 8-10 and the organic electroluminescent element (organic EL element) of Comparative Example 2 is shown. The current density-voltage characteristic of the semilog display of the organic electroluminescent element (organic EL element) of Examples 8 to 10 and Comparative Example 2 is shown. The brightness | luminance-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 8-10 and the comparative example 2 is shown. The luminous efficiency-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 8 to 10 and Comparative Example 2 is shown. The current efficiency-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 8 to 10 and Comparative Example 2 is shown. The brightness | luminance-current density characteristic of the organic electroluminescent element (organic EL element) of Examples 8-10 and Comparative Example 2 is shown. The electroluminescence (EL) spectrum of the organic electroluminescent element (organic EL element) of Examples 11-13 and Comparative Example 3 is shown. The current density-voltage characteristic of the real number display of the organic electroluminescent element (organic EL element) of Examples 11-13 and Comparative Example 3 is shown. The current density-voltage characteristic of the semi-log display of the organic electroluminescent element (organic EL element) of Examples 11-13 and Comparative Example 3 is shown. The brightness | luminance-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 11-13 and Comparative Example 3 is shown. The luminous efficiency-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 11-13 and Comparative Example 3 is shown. The current efficiency-voltage characteristic of the organic electroluminescent element (organic EL element) of Examples 11-13 and Comparative Example 3 is shown. The brightness | luminance-current density characteristic of the organic electroluminescent element (organic EL element) of Examples 11-13 and Comparative Example 3 is shown. The fluorescence quantum yield [photon number (photon number) -wavelength] of Example 14 (35PYREPY) is shown. The fluorescence quantum yield [photon number (photon number) -wavelength] of Example 15 (26PYREPY) is shown. The fluorescence quantum yield [photon number (photon number) -wavelength] of Example 16 (46PYREPYM) is shown. The current density-voltage characteristic of the electronic only device of Examples 17-19 is shown. The mobility-electric field strength of the electron mobility measuring elements of Examples 20 to 22 and Comparative Example 4 is shown. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. It is sectional drawing which shows an example of the organic electroluminescent element in this invention. ¹ shows the ¹ H-NMR spectrum of 2,5-di (pyren-1-yl) thiophene. FIG. 63 is an enlarged view of FIG. 62. 2 shows a mass spectrum (mass spectrum) of 2,5-di (pyren-1-yl) thiophene. It is the graph which evaluated the thermophysical property of 2, 5- di (pyren-1-yl) thiophene. It is TGA (thermobalance) of 2,5-di (pyren-1-yl) thiophene, line (A) is a thermogravimetric decrease curve, and line (B) is a curve showing the heating state. It is a graph which shows the optical physical-property evaluation of 2, 5- di (pyren- 1-yl) thiophene measured using the toluene solution of 2, 5- di (pyren- 1-yl) thiophene. It is a graph which shows the optical physical-property evaluation of 2, 5- di (pyren- 1-yl) thiophene measured using the chloroform solution of 2, 5- di (pyren- 1-yl) thiophene. It is a graph which shows the optical physical-property evaluation of the 2, 5- di (pyren- 1-yl) thiophene measured using the 2, 5- di (pyren- 1-yl) thiophene thin film. It is a graph which shows the photoluminescence intensity | strength (normalization) of quartz and 2, 5- di (pyren-1-yl) thiophene. The electroluminescent spectrum (fluorescence spectrum) of the organic electroluminescent element (organic EL element) of Example 24 is shown. The current density-voltage characteristic of the organic electroluminescent element (organic EL element) of Example 24 is shown. The luminance-voltage characteristic of the organic electroluminescent element (organic EL element) of Example 24 is shown. The luminous efficiency-luminance characteristic of the organic electroluminescent element (organic EL element) of Example 24 is shown. The current efficiency-luminance characteristic of the organic electroluminescent element (organic EL element) of Example 24 is shown. The luminance-voltage density characteristic of the organic electroluminescent element (organic EL element) of Example 24 is shown. The electroluminescent spectrum (fluorescence spectrum) of the organic electroluminescent element (organic EL element) of Example 25 is shown. The current density-voltage characteristic of the organic electroluminescent element (organic EL element) of Example 25 is shown. The luminance-voltage characteristic of the organic electroluminescent element (organic EL element) of Example 25 is shown. The luminous efficiency-luminance characteristic of the organic electroluminescent element (organic EL element) of Example 25 is shown. The current efficiency-luminance characteristic of the organic electroluminescent element (organic EL element) of Example 25 is shown. The luminance-voltage density characteristic of the organic electroluminescent element (organic EL element) of Example 25 is shown.

1 Substrate 2 Anode (ITO)
3 Light emitting layer 4 Cathode 5 Hole transport layer (hole transport layer)
6 Electron transport layer 7 Hole injection layer (hole injection layer)
8 Electron injection layer 9 Hole blocking layer (hole blocking layer)

Claims (6)

The following general formula (1)
(Where Q is
R ^{1 to} R ⁹ are groups selected from the group consisting of hydrogen, a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, and the number of carbon atoms R ¹⁰ to R ²⁰ are groups independently selected from the group consisting of 1 to 6 linear or branched alkylamino groups, and R ¹⁰ to R ²⁰ are each selected from hydrogen and a linear or branched alkyl group having 1 to 6 carbon atoms. Each group is independently selected from the group
A dipyrene derivative represented by   An electron transport material comprising the dipyrene derivative according to claim 1.   A luminescent material comprising the dipyrene derivative according to claim 1.   An organic electroluminescence device comprising the dipyrene derivative according to claim 1.   An organic electroluminescence device using the dipyrene derivative according to claim 1 for an electron transport layer.   An organic electroluminescence device using the dipyrene derivative according to claim 1 as a light emitting layer.