JP2019508410A - Nitrogen-containing compound and organic light emitting device containing the same - Google Patents

Abstract

  The present specification provides a nitrogen-containing compound and an organic light emitting device including the same.

Description

  The present specification relates to a nitrogen-containing compound and an organic light emitting device including the same.

  This specification claims the benefit of the filing date of Korean Patent Application No. 10-2016-0024290, filed Feb. 29, 2016, to the Korean Patent Office, the entire content of which is incorporated herein.

  In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic light emitting device utilizing an organic light emitting phenomenon usually has a structure including an anode and a cathode, and an organic layer between them. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer often has a multilayer structure made of different materials, for example, a hole injection layer, a hole transport layer, and a light emitting layer. , Electron transport layer, electron injection layer and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer, and the injected holes and the electrons come into contact with each other. , An exciton is formed and emits light when the exciton falls back to the ground state again.

  There is a continuing need to develop new materials for organic light emitting devices as described above.

  Described herein are nitrogen-containing compounds and organic light emitting devices comprising the same.

前記化学式１において、
Ｒ１、Ｒ２およびＲ７は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；シアノ基；ニトロ基；置換もしくは非置換のアルキル基；置換もしくは非置換のアリール基；またはＮ、Ｏ、およびＳのうちの１個以上を含む置換もしくは非置換のヘテロ環基であり、
Ｒ３とＲ４が結合して環を形成するか、Ｒ５とＲ６は結合して環を形成し、環を形成しない基は、Ｒ１、Ｒ２およびＲ７の定義と同じであり、
Ｌ１は、直接結合；置換もしくは非置換のアリーレン基；または置換もしくは非置換のヘテロアリーレン基であり、
Ａｒ_１〜Ａｒ_３は、互いに同一または異なり、それぞれ独立に、ニトロ基；置換もしくは非置換のシリル基；置換もしくは非置換のホスフィンオキシド基；置換もしくは非置換のアルキル基；置換もしくは非置換のアリールアミン基；置換もしくは非置換のアリール基；またはＮ、Ｏ、およびＳのうちの１個以上を含む置換もしくは非置換のヘテロ環基である。 One embodiment of the present specification provides a nitrogen-containing compound represented by the following chemical formula 1:
[Chemical formula 1]

In the above Chemical Formula 1,
R 1, R 2 and R 7 are the same or different from each other and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or N, O And a substituted or unsubstituted heterocyclic group containing one or more of S and
Groups in which R3 and R4 combine to form a ring, or R5 and R6 combine to form a ring and do not form a ring are as defined in R1, R2 and R7,
L 1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar _{1 to} Ar ₃ are the same or different from each other, each independently a nitro group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl An amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group containing one or more of N, O, and S.

  In one embodiment of the present invention, a first electrode, a second electrode provided opposite to the first electrode, and a single layer provided between the first electrode and the second electrode An organic light emitting device comprising the above organic layer, wherein one or more layers of the organic layer contain the nitrogen-containing compound of the chemical formula 1.

  The nitrogen-containing compound described in the present specification is used as a material of the organic layer of the organic light emitting device. The compounds according to at least one embodiment can improve the efficiency, improve the low driving voltage and / or improve the life characteristics in the organic light emitting device.

The example of the organic light emitting element which consists of the board | substrate 1, the anode 2, the light emitting layer 3, and the cathode 4 is shown. The example of the organic light emitting element which consists of the board | substrate 1, the anode 2, the positive hole injection layer 5, the positive hole transport layer 6, the light emitting layer 7, the electron carrying layer 8, and the cathode 4 is shown.

  Hereinafter, the present specification will be described in more detail.

  One embodiment of the present specification provides a nitrogen-containing compound represented by the above Chemical Formula 1.

  Examples of the substituent are described below, but are not limited thereto.

  In the present specification, the term "substituted or unsubstituted" is a halogen group, a cyano group, a nitro group, an amine group, a silyl group, a phosphine oxide group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocycle An alkyl group; an alkyl aryl group; an alkyl amine group; a heteroaryl amine group; and an aryl amine group, which is substituted or unsubstituted with one or more substituents, or It means that two or more substituents of the exemplified substituents are linked substituted or unsubstituted. For example, the “substituent in which two or more substituents are linked” may be a biphenyl group. That is, the biphenyl group may be an aryl group, and is interpreted as a substituent in which two phenyl groups are linked.

  As used herein, a halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the amine group is —NH ₂ ; a monoalkylamine group; a dialkylamine group; an N-alkylarylamine group; a monoarylamine group; a diarylamine group; an N-arylheteroarylamine group; The arylamine group may be selected from the group consisting of a monoheteroarylamine group and a diheteroarylamine group, and the number of carbon atoms is not particularly limited but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, Ditolylamine group, N-phenyltrilamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group , N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, etc. The present invention is not limited to.

  In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. In one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1 -Ethyl-propyl, 1,1-dimethyl-propane Pills, isohexyl, 4-methylhexyl, 5-methylhexyl there are such as, but not limited to.

  In the present specification, the alkenyl group may be linear or branched and the number of carbon atoms is not particularly limited but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2-20. According to another embodiment, the carbon number of the alkenyl group is 2-10. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3- Butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-one Yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but it is not limited thereto.

  In the present specification, the cycloalkyl group is not particularly limited, but one having 3 to 60 carbon atoms is preferable, and according to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethyl Examples include, but are not limited to, cyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.

  In the present specification, the silyl group is, specifically, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group Etc., but it is not limited to these.

  In the present specification, the phosphine oxide group specifically includes, but is not limited to, a diphenyl phosphine oxide group, dinaphthyl phosphine oxide and the like.

  In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6-30. According to one embodiment, the carbon number of the aryl group is 6-20. Although the said aryl group may turn into a phenyl group, a biphenyl group, terphenyl group etc. as a monocyclic aryl group, it is not limited to these. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group and the like, but is not limited thereto.

などになってもよい。ただし、これらに限定されるものではない。 When the fluorenyl group is substituted,

And so on. However, it is not limited to these.

  In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, S, Si, and Se as different elements, and the number of carbon atoms is not particularly limited. 60 are preferred. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine Group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzo Thiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, And the like dibenzofuranyl group, but is not limited thereto.

  In the present specification, as for the aryl group in the aralkyl group, the alkenyl group, the alkylaryl group, and the arylamine group, the descriptions regarding the aryl group described above are applicable.

  In the present specification, as for the alkyl group in the aralkyl group, the alkylaryl group and the alkylamine group, the descriptions regarding the alkyl group described above are applicable.

  In the present specification, the description of the aforementioned heterocyclic group is applicable to heteroaryl in heteroarylamine.

  In the present specification, as for the alkenyl group in the alkenyl group, the descriptions regarding the alkenyl group described above are applicable.

  In the present specification, except for arylene being a divalent group, the descriptions regarding the aforementioned aryl group are applicable.

  In the present specification, except for the fact that heteroarylene is a divalent group, the descriptions regarding the aforementioned heterocyclic group are applicable.

  In the present specification, the meaning of bonding to each other to form a ring means that adjacent groups bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; It means forming a substituted aliphatic heterocycle; or a substituted or unsubstituted aromatic heterocycle.

  In the present specification, the aliphatic hydrocarbon ring means a ring which is not aromatic and which consists only of carbon and hydrogen atoms.

  In the present specification, examples of the aromatic hydrocarbon ring include, but not limited to, benzene, naphthalene, anthracene and the like.

  In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of hetero atoms.

  In the present specification, the aromatic heterocycle means an aromatic ring containing one or more of hetero atoms.

  In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle may be monocyclic or polycyclic.

［化学式３］

前記化学式２および３において、
前記Ｒ１〜Ｒ７、Ｌ１およびＡｒ_１〜Ａｒ_３は、化学式１における定義と同じであり、
Ｒ１１〜Ｒ１８は、前記Ｒ１、Ｒ２およびＲ７の定義と同じである。 In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 2 or 3.
[Chemical formula 2]

[Chemical formula 3]

In the above formulas 2 and 3,
R 1 to R 7, L 1 and Ar _{1 to} Ar ₃ are the same as defined in Chemical Formula 1,
R11 to R18 are the same as the definitions of R1, R2 and R7.

In one embodiment of the present specification, Ar _{1 to} Ar ₃ are the same or different from each other, and each independently a cyano group; a nitro group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; Or unsubstituted C1-C30 alkyl group; substituted or unsubstituted C6-C60 arylamine group; substituted or unsubstituted C6-C60 aryl group; or N, O, and S It is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms which contains one or more of them.

  In one embodiment of the present specification, in the chemical formula 1, L 1 is a direct bond; substituted or unsubstituted phenylene group; substituted or unsubstituted naphthylene group; substituted or unsubstituted divalent phenothiazine group (phenothiazine); A substituted or unsubstituted divalent phenoxazine group (phenoxazine); a substituted or unsubstituted divalent carbazole group; a substituted or unsubstituted divalent benzocarbazole group; a substituted or unsubstituted divalent benzimidazole group; Substituted or unsubstituted divalent thiophene group; substituted or unsubstituted divalent furan group; substituted or unsubstituted divalent dibenzofuran group; substituted or unsubstituted divalent dibenzothiophene group; substituted or unsubstituted A divalent triazine group; a substituted or unsubstituted divalent pyridine group; Is a substituted or unsubstituted divalent quinazoline group; substituted or unsubstituted divalent pyrimidine group; a substituted or unsubstituted divalent quinoline group.

  In one embodiment of the present specification, in the chemical formula 1, L 1 is a direct bond; substituted or unsubstituted phenylene group; substituted or unsubstituted divalent phenothiazine group (substituted or unsubstituted divalent) Phenoxazine group (phenoxazine); substituted or unsubstituted divalent carbazole group; substituted or unsubstituted divalent benzocarbazole group; substituted or unsubstituted divalent benzimidazole group; substituted or unsubstituted divalent A dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; a substituted or unsubstituted divalent triazine group; or a substituted or unsubstituted divalent quinazoline group.

  In one embodiment of the present specification, in the chemical formula 1, L1 is a direct bond; a phenylene group; a naphthylene group; a divalent phenothiazine group; a divalent phenoxazine group; a divalent carbazole group A divalent benzocarbazole group, a divalent benzimidazole group, a divalent thiophene group, a divalent furan group, a divalent dibenzofuran group, a divalent dibenzothiophene group, a divalent triazine group, a divalent pyridine A divalent pyrimidine group; a divalent quinoline group; or a divalent quinazoline group.

  In one embodiment of the present specification, in the chemical formula 1, L1 is a direct bond; a phenylene group; a divalent phenothiazine group; a divalent phenoxazine group; a divalent carbazole group; Or a bivalent benzimidazole group; a bivalent dibenzofuran group; a bivalent dibenzothiophene group; a bivalent triazine group; or a bivalent quinazoline group.

  In one embodiment of the present specification, in the chemical formula 1, L1 is a direct bond; a phenylene group; a divalent carbazole group; a divalent dibenzofuran group; a divalent dibenzothiophene group; a divalent triazine group; Valence quinazoline group.

  In one embodiment of the present specification, L1 is a direct bond.

  In one embodiment of the present specification, it is a substituted or unsubstituted arylene group.

  In one embodiment of the present specification, L 1 is a substituted or unsubstituted heteroarylene group.

  In one embodiment of the present specification, L 1 is a phenylene group; a biphenylylene group; a bivalent terphenyl group; a bivalent quaterphenyl group; a naphthalene group; a bivalent anthracene group; a bivalent fluorene group; A phenanthrene group; a divalent pyrene group; or a divalent triphenylene group.

  In one embodiment of the present specification, L 1 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; a substituted or unsubstituted bivalent terphenyl group; a substituted or unsubstituted bivalent quaternary phenyl A substituted or unsubstituted naphthalene group; a substituted or unsubstituted divalent anthracene group; a substituted or unsubstituted divalent fluorene group; a substituted or unsubstituted divalent phenanthrene group; a substituted or unsubstituted bivalent Or a substituted or unsubstituted divalent triphenylene group.

  In one embodiment of the present specification, L 1 is a substituted or unsubstituted divalent phenothiazine group (substituted or unsubstituted divalent phenoxazine group); a substituted or unsubstituted divalent carbazole A substituted or unsubstituted divalent benzocarbazole group; a substituted or unsubstituted divalent benzimidazole group; a substituted or unsubstituted divalent thiophene group; a substituted or unsubstituted divalent furan group; Unsubstituted bivalent dibenzofuran group; substituted or unsubstituted bivalent dibenzothiophene group; substituted or unsubstituted bivalent triazine group; substituted or unsubstituted bivalent pyridine group; substituted or unsubstituted bivalent A pyrimidine group of: substituted or unsubstituted divalent quinoline group; or substituted or unsubstituted It is a divalent quinazoline group.

  In one embodiment of the present specification, L 1 represents a divalent phenothiazine group; a divalent phenoxazine group; a divalent carbazole group; a divalent benzocarbazole group; a divalent benzimidazole group A divalent thiophene group, a divalent furan group, a divalent dibenzofuran group, a divalent dibenzothiophene group, a divalent triazine group, a divalent pyridine group, a divalent pyrimidine group, a divalent quinoline group; Or a divalent quinazoline group.

In one embodiment of the present specification, in the chemical formula 1, Ar ₁ represents a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl A substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; substituted or unsubstituted benzonaphthofuran group; substituted or unsubstituted benzonaphthothiophene group; substituted or unsubstituted phenothiazine group (substituted or unsubstituted phenoxazine group (phen) oxazine); substituted or unsubstituted quinazole group; substituted or unsubstituted pyridine group; substituted or unsubstituted pyrimidine group; substituted or unsubstituted triazine group; substituted or unsubstituted phenanthroline group; substituted or unsubstituted benzimidazole A substituted or unsubstituted benzothiazole group; or a substituted or unsubstituted benzoxazole group.

In one embodiment of the present specification, in the chemical formula 1, Ar ₁ represents a phosphine oxide group; a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a phenanthrene group; a triphenylene group; a fluorene group; a carbazole group; Dibenzothiophene group; benzonaphthofuran group; benzonaphthothiophene group; phenothiazine group; phenoxazine group (phenoxazine); quinazole group; pyridine group; pyrimidine group; triazine group; phenanthroline group; benzimidazole group; Or a benzoxazole group.

In one embodiment of the present specification, in the chemical formula 1, Ar ₁ is a phenyl group; a phenyl group substituted or unsubstituted with a substituent selected from the group consisting of a cyano group, a silyl group, and an alkyl group; Terphenyl group; Naphthyl group; Fluorene group; Carbazole group substituted or unsubstituted with aryl group; Dibenzofuran group; Dibenzothiophene group; Quinazole group substituted or unsubstituted with aryl group; or Triazine group substituted or unsubstituted with aryl group It is.

In one embodiment of the present specification, in the chemical formula 1, -L ₁ -Ar ₁ is selected from the following structural formulas.

In one embodiment of the present specification, in the chemical formula 1, Ar ₂ and Ar ₃ are the same or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or N, O, and It is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms which contains one or more of S.

In one embodiment of the present specification, in the chemical formula 1, Ar ₂ and Ar ₃ are the same or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, in the chemical formula 1, Ar ₂ and Ar ₃ are the same or different from each other, and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted A substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; or a substituted or unsubstituted fluorene group.

In one embodiment of the present specification, in the chemical formula 1, Ar ₂ and Ar ₃ are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with an aryl group; biphenyl substituted or unsubstituted with an aryl group An aryl group substituted or unsubstituted terphenyl group; an aryl group substituted or unsubstituted naphthyl group; an aryl group substituted or unsubstituted phenanthrene group; an aryl group substituted or unsubstituted triphenylene group; or an aryl group Or a substituted or unsubstituted fluorene group with an alkyl group.

In one embodiment of the present specification, Ar ₂ and Ar ₃ in the chemical formula 1 are the same or different from each other, and each independently a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a phenanthrene group; It is a dimethyl fluorene group.

In one embodiment of the present specification, in the chemical formula 1, -N (Ar ₂ Ar ₃ ) is selected from the following structural formulas.

  In one embodiment of the present specification, R 1, R 2 and R 7 are hydrogen, and the group which does not form a ring among R 3 and R 4 or R 5 and R 6 is hydrogen.

  In one embodiment of the present specification, R11 to R18 are hydrogen.

In one embodiment of the present specification, the chemical formula 1 may be selected from the following structural formulas.

The nitrogen-containing compound according to one embodiment of the present specification is produced by the production method described later.
[Reaction Formula 1]

  The reaction conditions and materials described in Reaction Scheme 1 can be those known in the art, and the type or number of substituents not described in the reaction scheme are also known in the art. It can be changed depending on the reaction conditions and materials.

In the reaction formula 1, Ar1 can mean a substituent excluding a halogen atom of a compound selected from the following compounds.

  In addition, the present specification provides an organic light emitting device including the compound represented by Formula 1 above.

  In one embodiment of the present specification, a first electrode, a second electrode provided opposite to the first electrode, and one or more layers provided between the first electrode and the second electrode. An organic light emitting device including an organic layer, wherein one or more layers of the organic layer include the nitrogen-containing compound of the chemical formula 1.

  The organic layer of the organic light emitting device of the present specification may have a single layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as the organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

  In one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, the hole transport layer, or the positive electrode layer. The layer that simultaneously performs hole injection and transport contains the nitrogen-containing compound of Formula 1.

  In another embodiment, the organic layer includes a light emitting layer, and the light emitting layer includes the nitrogen-containing compound of Formula 1.

  In one embodiment of the present specification, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the nitrogen-containing compound of Formula 1.

  In one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer includes the nitrogen-containing compound of Formula 1.

  In one embodiment of the present specification, the electron transport layer, the electron injection layer, or a layer simultaneously performing electron transport and electron injection includes the nitrogen-containing compound of the formula 1.

  In another embodiment, the organic layer includes a light emitting layer and an electron transport layer, and the electron transport layer includes the nitrogen-containing compound of Formula 1.

  In another embodiment, the organic light emitting device may be an organic light emitting device of a normal type in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

  In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

  For example, the structure of the organic light emitting device according to one embodiment of the present specification is illustrated in FIGS.

  FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4. In this structure, the nitrogen-containing compound may be included in the light emitting layer.

  FIG. 2 shows an example of the organic light emitting device comprising the substrate 1, the anode 2, the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, the electron transport layer 8 and the cathode 4. In this structure, the compound may be contained in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

  The organic light-emitting device of the present invention is a material and method known in the art except that one or more of the organic layers contain the compound of the present invention, ie, the nitrogen-containing compound of Formula 1 above. Manufactured by

  When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same or different materials.

  The organic light emitting device of the present invention is known in the art except that one or more of the organic layers contain the nitrogen-containing compound of the formula 1, ie, the compound represented by the formula 1. Manufactured with materials and methods.

  For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a metal or a conductive metal oxide or an alloy thereof on the substrate using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation. Is formed to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a substance usable as a cathode is vapor deposited thereon Manufactured by In addition to such a method, an organic light emitting element can be formed by depositing a cathode material, an organic material layer and an anode material in this order on a substrate.

  In addition, the compound of Chemical Formula 1 is formed on the organic layer by the solution coating method as well as the vacuum deposition method when manufacturing the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, ink jet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.

  In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

  In another embodiment, the first electrode is a cathode and the second electrode is an anode.

As the anode substance, usually, a substance having a large work function is preferable so that hole injection into the organic layer becomes smooth. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; zinc oxide, indium oxide, indium tin oxide (ITO), indium Metal oxides such as zinc oxide (IZO); combinations of metals such as ZnO: Al or SnO ₂ : Sb with oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1) And (2-dioxy) thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, etc., but not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, metals such as aluminum, silver, tin and lead, or alloys thereof; LiF / Al or LiO ₂ / There is a multilayer structure such as Al, but it is not limited thereto.

  The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, has the ability to transport holes, and the hole injection effect from the anode, the light emitting layer or the light emitting material Compounds having an excellent hole injection effect, preventing migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and having excellent thin film forming ability are preferable. It is preferable that the hole injecting material HOMO (highest occupied molecular orbital) be between the work function of the anode material and the HOMO of the peripheral organic layer. Specific examples of the hole injecting material include metal porphyrin (porphyrin), oligothiophene, organic substance of arylamine type, organic substance of hexanitrile hexaazatriphenylene type, organic substance of quinacridone type, organic substance of perylene type, There are anthraquinone and conductive polymers of polyaniline and polythiophene, but not limited thereto.

  The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and as a hole transport material, the light emitting layer receives hole transport from the anode or the hole injection layer The substance which can be transferred to the organic substance is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

The light-emitting substance is a substance capable of emitting light in the visible light region by receiving and combining holes and electron transport from the hole transport layer and the electron transport layer, respectively, and having high quantum efficiency with respect to fluorescence and phosphorescence. Is preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzthiazole, and the like Benzimidazole compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorenes, rubrenes and the like, but not limited thereto.

  The light emitting layer can include a host material and a dopant material. Host materials include fused aromatic ring derivatives or heterocycle containing compounds. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds and the like, and as the heterocycle-containing compounds, carbazole derivatives, dibenzofuran derivatives, ladder type furan There is a compound, a pyrimidine derivative and the like, but it is not limited thereto.

  The dopant material includes aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes and the like. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene having an arylamino group, anthracene, chrysene, periflanthene, etc., and a styrylamine compound Is a compound in which at least one arylvinyl group is substituted by a substituted or unsubstituted arylamine, and one or two members selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group The substituent selected above is substituted or unsubstituted. Specific examples include, but are not limited to, styrylamine, styryl diamine, styryl triamine, styryl tetraamine and the like. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a substance that can smoothly receive the electron injection from the cathode and transfer it to the light emitting layer. Substances with high mobility for are preferred. Specific examples thereof include Al complexes of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used by the prior art. In particular, examples of suitable cathode materials are the usual materials which have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.

  The electron injection layer is a layer for injecting electrons from the electrode, has an ability to transport electrons, has an electron injection effect from the cathode, and an excellent electron injection effect for the light emitting layer or the light emitting material, The compound which prevents the movement to the hole injection layer of the exciton produced | generated by these, and is excellent in the thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone and derivatives thereof, metal complex compounds, And nitrogen-containing 5-membered ring derivatives, but not limited thereto.

  As the metal complex compound, 8-hydroxyquinolinatolithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinato) Linato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] Quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholate) aluminum , Bis (2-methyl-8-quinolinato) (2-naphth) Acrylate), and the like gallium, but are not limited to these.

  The organic light emitting device according to the present specification may be of a front side light emitting type, a back side light emitting type, or a double side light emitting type, depending on the material used.

  In one embodiment of the present specification, the nitrogen-containing compound represented by Formula 1 is included in an organic solar cell or an organic transistor other than the organic light emitting device.

  Hereinafter, in order to specifically describe the present specification, the present invention will be described in detail by way of examples. However, the embodiments according to the present specification can be transformed into various different forms, and the scope of the present specification is not interpreted as being limited to the embodiments detailed below. The examples herein are provided to more fully illustrate the present specification to those of average skill in the art.

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝フェニルを用いると、前記化合物Ａ−１を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−１（１０．０ｇ、３０．５８ｍｍｏｌ）、ジ（［１，１'−ビフェニル］−４−イル）アミン（１０．８０ｇ、３３．６４ｍｍｏｌ）をキシレン１８０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．８２ｇ、３９．７６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１６ｇ、０．３１ｍｍｏｌ）を入れた後、３時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート２５０ｍｌで再結晶して、前記化合物１（１３．３８ｇ、収率：７１％）を製造した。 Preparation Example 1 Synthesis of Compound 1 Following Compound 1

The compound A-1 can be obtained by using A as a starting material and using Ar1 = phenyl in step 3 of the reaction formula 1. Compound A-1 (10.0 g, 30.58 mmol) and di ([1,1'-biphenyl] -4-yl) amine (10.80 g, 33.64 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolved in 180 ml of xylene, sodium tert-butoxide (3.82 g, 39.76 mmol) is added, and bis (tri-tert-butylphosphine) palladium (0) (0.16 g, 0.31 mmol) is added. The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 250 ml of ethyl acetate to produce Compound 1 (13.38 g, yield: 71%).

MS [M + H] ⁺ = 613

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝フェニルを用いると、前記化学物Ａ−１を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−１（１０．０ｇ、３０．５８ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−ｙｌ）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（１２．１４ｇ、３８．５３ｍｍｏｌ）をキシレン１６０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．８２ｇ、３９．７６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１６ｇ、０．３１ｍｍｏｌ）を入れた後、２時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート２００ｍｌで再結晶して、前記化合物２（１２．２７ｇ、収率：６１％）を製造した。 Preparation Example 2 Synthesis of Compound 2 Following Compound 2

The chemical substance A-1 can be obtained by using A as the starting material and using Ar1 = phenyl in step 3 of the reaction formula 1. Compound A-1 (10.0 g, 30.58 mmol), N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving -2-amine (12.14 g, 38.53 mmol) in 160 ml of xylene, sodium tert-butoxide (3.82 g, 39.76 mmol) is added and bis (tri-tert-butylphosphine) palladium is added. After adding (0) (0.16 g, 0.31 mmol), the mixture was heated and stirred for 2 hours. The temperature was lowered to normal temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 200 ml of ethyl acetate to produce the above compound 2 (12.27 g, yield: 61%).

MS [M + H] ⁺ = 653

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝ビフェニルを用いると、前記化合物Ａ−２を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−２（１０．０ｇ、２４．８１ｍｍｏｌ）、ジ（［１，１'−ビフェニル］−４−イル）アミン（８．７６ｇ、２７．３０ｍｍｏｌ）をキシレン２４０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．１０ｇ、３２．２６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１３ｇ、０．２５ｍｍｏｌ）を入れた後、６時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン２２０ｍｌで再結晶して、前記化合物３（１５．９２ｇ、収率：９３％）を製造した。 <Production Example 3> Synthesis of Compound of the Following Compound 3

The compound A-2 can be obtained by using A as a starting material and using Ar1 = biphenyl in step 3 of the reaction formula 1. Compound A-2 (10.0 g, 24.81 mmol) and di ([1,1'-biphenyl] -4-yl) amine (8.76 g, 27.30 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolved in 240 ml of xylene, sodium tert-butoxide (3.10 g, 32.26 mmol) is added, and bis (tri-tert-butylphosphine) palladium (0) (0.13 g, 0.25 mmol) is added. The mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 220 ml of tetrahydrofuran to produce the compound 3 (15.92 g, yield: 93%).

MS [M + H] ⁺ = 689

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝ビフェニルを用いると、前記化合物Ａ−２を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−２（１０．０ｇ、２４．８１ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（８．７６ｇ、２７．３０ｍｍｏｌ）をキシレン２２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．１０ｇ、３２．２６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１３ｇ、０．２５ｍｍｏｌ）を入れた後、４時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート３５０ｍｌで再結晶して、前記化合物４（１４．６４ｇ、収率：８１％）を製造した。 <Production Example 4> Synthesis of Compound of the Following Compound 4

The compound A-2 can be obtained by using A as a starting material and using Ar1 = biphenyl in step 3 of the reaction formula 1. Compound A-2 (10.0 g, 24.81 mmol), N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving -2-amine (8.76 g, 27.30 mmol) in 220 ml of xylene, sodium tert-butoxide (3.10 g, 32.26 mmol) is added and bis (tri-tert-butylphosphine) palladium is added. After adding (0) (0.13 g, 0.25 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 350 ml of ethyl acetate to produce the above compound 4 (14.64 g, yield: 81%).

MS [M + H] ⁺ = 729

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝２−ナフチルを用いると、前記化合物Ａ−５を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−５（１０．０ｇ、２６．５３ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（１０．５３ｇ、３４．４８ｍｍｏｌ）をキシレン１８０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．３１ｇ、４７．７１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１４ｇ、０．２７ｍｍｏｌ）を入れた後、２時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート２００ｍｌで再結晶して、前記化合物５（１２．３５ｇ、収率：６６％）を製造した。 Production Example 5 Synthesis of Compound 5 Following Compound 5

The compound A-5 can be obtained by using A as a starting material and using Ar1 = 2-naphthyl in step 3 of the reaction formula 1. Compound A-5 (10.0 g, 26.53 mmol), N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving -2-amine (10.53 g, 34.48 mmol) in 180 ml of xylene, sodium tert-butoxide (3.31 g, 47.71 mmol) is added and bis (tri-tert-butylphosphine) palladium is added. After adding (0) (0.14 g, 0.27 mmol), the mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 200 ml of ethyl acetate to produce the above compound 5 (12.35 g, yield: 66%).

MS [M + H] ⁺ = 703

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝２−ナフチルを用いると、前記化合物Ａ−５を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−５（１０．０ｇ、２６．５３ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−［１，１'：４'，１''−ターフェニル］−４−アミン（１１．５８ｇ、２９．１８ｍｍｏｌ）をキシレン２６０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．３１ｇ、４７．７１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１４ｇ、０．２７ｍｍｏｌ）を入れた後、９時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン３００ｍｌで再結晶して、前記化合物６（１７．７１ｇ、収率：９１％）を製造した。 Preparation Example 6 Synthesis of Compound 6 Following Compound 6

The compound A-5 can be obtained by using A as a starting material and using Ar1 = 2-naphthyl in step 3 of the reaction formula 1. Compound A-5 (10.0 g, 26.53 mmol), N-([1,1′-biphenyl] -4-yl)-[1,1 ′: 4 ′, in a 500 ml round bottom flask under a nitrogen atmosphere. After completely dissolving 1 ′ ′-terphenyl] -4-amine (11.58 g, 29.18 mmol) in 260 ml of xylene, sodium tert-butoxide (3.31 g, 47.71 mmol) is added to give bis (triol). After adding -tert-butylphosphine) palladium (0) (0.14 g, 0.27 mmol), the mixture was heated and stirred for 9 hours. The temperature was lowered to normal temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 300 ml of tetrahydrofuran to produce the above-mentioned compound 6 (17.71 g, yield: 91%).

MS [M + H] ⁺ = 703

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝ターフェニルを用いると、前記化合物Ａ−７を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−７（１０．０ｇ、２４．８１ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（８．７６ｇ、２７．３０ｍｍｏｌ）をキシレン２２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．６２ｇ、２７．３１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１１ｇ、０．２１ｍｍｏｌ）を入れた後、４時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート３５０ｍｌで再結晶して、前記化合物７（１４．２６ｇ、収率：８４％）を製造した。 Preparation Example 7 Synthesis of Compound 7 Following Compound 7

The compound A-7 can be obtained by using A as a starting material and using Ar1 = terphenyl in step 3 of the reaction formula 1. Compound A-7 (10.0 g, 24.81 mmol), N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving -2-amine (8.76 g, 27.30 mmol) in 220 ml of xylene, sodium tert-butoxide (2.62 g, 27.31 mmol) is added and bis (tri-tert-butylphosphine) palladium is added. After adding (0) (0.11 g, 0.21 mmol), the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, xylene was concentrated under reduced pressure and recrystallized with 350 ml of ethyl acetate to produce the compound 7 (14.26 g, yield: 84%).

MS [M + H] ⁺ = 805

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝ターフェニルを用いると、前記化合物Ａ−７を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−７（１０．０ｇ、２４．８１ｍｍｏｌ）、Ｎ−フェニル−［１，１'−ビフェニル］−４−アミン（５．６６ｇ、２３．１１ｍｍｏｌ）をキシレン２８０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．６２ｇ、２７．３１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１１ｇ、０．２１ｍｍｏｌ）を入れた後、６時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート３５０ｍｌで再結晶して、前記化合物８（１０．０８ｇ、収率：７０％）を製造した。 Preparation Example 8 Synthesis of Compound 8 Following Compound 8

The compound A-7 can be obtained by using A as a starting material and using Ar1 = terphenyl in step 3 of the reaction formula 1. Compound A-7 (10.0 g, 24.81 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (5.66 g, 23.11 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving in 280 ml of xylene, sodium tert-butoxide (2.62 g, 27.31 mmol) is added, and bis (tri-tert-butylphosphine) palladium (0) (0.11 g, 0.21 mmol) is added. The mixture was heated and stirred for 6 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, xylene was concentrated under reduced pressure and recrystallized with 350 ml of ethyl acetate to produce the above compound 8 (10.08 g, yield: 70%).

MS [M + H] ⁺ = 689

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝フェニルナフチルを用いると、前記化合物Ａ−９を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−９（１０．０ｇ、２２．０８ｍｍｏｌ）、Ｎ−フェニル−［１，１'−ビフェニル］−４−アミン（５．９５ｇ、２４．２８ｍｍｏｌ）をキシレン２３０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．６２ｇ、２７．３１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１１ｇ、０．２１ｍｍｏｌ）を入れた後、８時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート３５０ｍｌで再結晶して、前記化合物９（９．４７ｇ、収率：６５％）を製造した。 <Production Example 9> Synthesis of Compound of the Following Compound 9

The compound A-9 can be obtained by using A as a starting material and using Ar1 = phenylnaphthyl in step 3 of the reaction formula 1. Compound A-9 (10.0 g, 22.08 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (5.95 g, 24.28 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolved in 230 ml of xylene, add sodium tert-butoxide (2.62 g, 27.31 mmol) and add bis (tri-tert-butylphosphine) palladium (0) (0.11 g, 0.21 mmol). The mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 350 ml of ethyl acetate to produce the above compound 9 (9.47 g, yield: 65%).

MS [M + H] ⁺ = 663

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝フェニルを用いると、前記化合物Ｂ−１を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−１（１０．０ｇ、３０．５８ｍｍｏｌ）、ジ（［１，１'−ビフェニル］−４−イル）アミン（１０．８０ｇ、３３．６４ｍｍｏｌ）をキシレン２２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．８２ｇ、３９．７６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１６ｇ、０．３１ｍｍｏｌ）を入れた後、５時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート２６０ｍｌで再結晶して、前記化合物１０（１２．０５ｇ、収率：６３％）を製造した。 <Production Example 10> Synthesis of Compound of the Following Compound 10

The compound B-1 can be obtained by using B as a starting material and using Ar1 = phenyl in step 3 of the reaction formula 1. Compound B-1 (10.0 g, 30.58 mmol) and di ([1,1'-biphenyl] -4-yl) amine (10.80 g, 33.64 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolved in 220 ml of xylene, add sodium tert-butoxide (3.82 g, 39.76 mmol) and add bis (tri-tert-butylphosphine) palladium (0) (0.16 g, 0.31 mmol). The mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 260 ml of ethyl acetate to produce the above compound 10 (12.05 g, yield: 63%).

MS [M + H] ⁺ = 613

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝フェニルを用いると、前記化学物Ｂ−１を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−１（１０．０ｇ、３０．５８ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（１２．１４ｇ、３８．５３ｍｍｏｌ）をキシレン２００ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．８２ｇ、３９．７６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１６ｇ、０．３１ｍｍｏｌ）を入れた後、４時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート２１０ｍｌで再結晶して、前記化合物１１（１１．０５ｇ、収率：５５％）を製造した。 <Production Example 11> Synthesis of Compound of the Following Compound 11

The chemical substance B-1 can be obtained by using B as a starting material and using Ar1 = phenyl in step 3 of the reaction formula 1. Compound B-1 (10.0 g, 30.58 mmol), N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving -2-amine (12.14 g, 38.53 mmol) in 200 ml of xylene, sodium tert-butoxide (3.82 g, 39.76 mmol) is added and bis (tri-tert-butylphosphine) palladium is added. After adding (0) (0.16 g, 0.31 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 210 ml of ethyl acetate to produce the above-mentioned compound 11 (11.05 g, yield: 55%).

MS [M + H] ⁺ = 653

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝４−ビフェニルを用いると、前記化合物Ｂ−２を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−２（１０．０ｇ、２４．８１ｍｍｏｌ）、ジ（［１，１'−ビフェニル］−４−ｙｌ）アミン（８．７６ｇ、２７．３０ｍｍｏｌ）をキシレン２８０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．１０ｇ、３２．２６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１３ｇ、０．２５ｍｍｏｌ）を入れた後、８時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン２３０ｍｌで再結晶して、前記化合物１２（１４．３３ｇ、収率：８４％）を製造した。 <Production Example 12> Synthesis of Compound of the Following Compound 12

The compound B-2 can be obtained by using B as a starting material and using Ar1 = 4-biphenyl in step 3 of the reaction formula 1. Compound B-2 (10.0 g, 24.81 mmol) and di ([1,1'-biphenyl] -4-yl) amine (8.76 g, 27.30 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving in 280 ml of xylene, sodium tert-butoxide (3.10 g, 32.26 mmol) is added, and bis (tri-tert-butylphosphine) palladium (0) (0.13 g, 0.25 mmol) is added. The mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 230 ml of tetrahydrofuran to produce the compound 12 (14.33 g, yield: 84%).

MS [M + H] ⁺ = 689

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝４−ビフェニルを用いると、前記化合物Ｂ−２を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−２（１０．０ｇ、２４．８１ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−ｙｌ）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（８．７６ｇ、２７．３０ｍｍｏｌ）をキシレン２６０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．１０ｇ、３２．２６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１３ｇ、０．２５ｍｍｏｌ）を入れた後、６時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート３６０ｍｌで再結晶して、前記化合物１３（１３．１８ｇ、収率：７２％）を製造した。 <Production example 13> Synthesis of the following compound 13

The compound B-2 can be obtained by using B as a starting material and using Ar1 = 4-biphenyl in step 3 of the reaction formula 1. Compound B-2 (10.0 g, 24.81 mmol), N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving -2-amine (8.76 g, 27.30 mmol) in 260 ml of xylene, sodium tert-butoxide (3.10 g, 32.26 mmol) is added and bis (tri-tert-butylphosphine) palladium is added. After adding (0) (0.13 g, 0.25 mmol), the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 360 ml of ethyl acetate to produce the compound 13 (13.18 g, yield: 72%).

MS [M + H] ⁺ = 729

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝２−ナフチルを用いると、前記化合物Ｂ−５を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−５（１０．０ｇ、２６．５３ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（１０．５３ｇ、３４．４８ｍｍｏｌ）をキシレン２２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．３１ｇ、４７．７１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１４ｇ、０．２７ｍｍｏｌ）を入れた後、４時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート２１０ｍｌで再結晶して、前記化合物１４（１２．３５ｇ、収率：６６％）を製造した。 Preparation Example 14 Synthesis of Compound 14 Following Compound 14

The compound B-5 can be obtained by using B as a starting material and using Ar1 = 2-naphthyl in step 3 of the reaction formula 1. Compound B-5 (10.0 g, 26.53 mmol), N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving -2-amine (10.53 g, 34.48 mmol) in 220 ml of xylene, sodium tert-butoxide (3.31 g, 47.71 mmol) is added and bis (tri-tert-butylphosphine) palladium is added. After adding (0) (0.14 g, 0.27 mmol), the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, xylene was concentrated under reduced pressure and recrystallized with 210 ml of ethyl acetate to produce the compound 14 (12.35 g, yield: 66%).

MS [M + H] ⁺ = 703

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝２−ナフチルを用いると、前記化合物Ｂ−５を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−５（１０．０ｇ、２６．５３ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−［１，１'：４'，１''−ターフェニル］−４−アミン（１１．５８ｇ、２９．１８ｍｍｏｌ）をキシレン３００ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．３１ｇ、４７．７１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１４ｇ、０．２７ｍｍｏｌ）を入れた後、１１時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン３１０ｍｌで再結晶して、前記化合物１５（１５．９４ｇ、収率：８２％）を製造した。 Preparation Example 15 Synthesis of Compound 15 Following Compound 15

The compound B-5 can be obtained by using B as a starting material and using Ar1 = 2-naphthyl in step 3 of the reaction formula 1. Compound B-5 (10.0 g, 26.53 mmol), N-([1,1′-biphenyl] -4-yl)-[1,1 ′: 4 ′, in a 500 ml round bottom flask under a nitrogen atmosphere. After completely dissolving 1 ′ ′-terphenyl] -4-amine (11.58 g, 29.18 mmol) in 300 ml of xylene, add sodium tert-butoxide (3.31 g, 47.71 mmol) to give bis (triol). After adding -tert-butylphosphine) palladium (0) (0.14 g, 0.27 mmol), the mixture was heated and stirred for 11 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 310 ml of tetrahydrofuran to produce the compound 15 (15.94 g, yield: 82%).

MS [M + H] ⁺ = 703

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝ターフェニルを用いると、前記化合物Ｂ−７を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−７（１０．０ｇ、２４．８１ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（８．７６ｇ、２７．３０ｍｍｏｌ）をキシレン２６０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．６２ｇ、２７．３１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１１ｇ、０．２１ｍｍｏｌ）を入れた後、６時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート３６０ｍｌで再結晶して、前記化合物１６（１２．８２ｇ、収率：７６％）を製造した。 Preparation Example 16 Synthesis of Compound of the Following Compound 16

The compound B-7 can be obtained by using B as a starting material and using Ar1 = terphenyl in step 3 of the reaction formula 1. Compound B-7 (10.0 g, 24.81 mmol), N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving -2-amine (8.76 g, 27.30 mmol) in 260 ml of xylene, sodium tert-butoxide (2.62 g, 27.31 mmol) is added and bis (tri-tert-butylphosphine) palladium is added. After adding (0) (0.11 g, 0.21 mmol), the mixture was heated and stirred for 6 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, xylene was concentrated under reduced pressure and recrystallized with 360 ml of ethyl acetate to produce Compound 16 (12.82 g, yield: 76%).

MS [M + H] ⁺ = 805

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝ターフェニルを用いると、前記化合物Ｂ−７を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−７（１０．０ｇ、２４．８１ｍｍｏｌ）、Ｎ−フェニル−［１，１'−ビフェニル］−４−アミン（５．６６ｇ、２３．１１ｍｍｏｌ）をキシレン３２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．６２ｇ、２７．３１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１１ｇ、０．２１ｍｍｏｌ）を入れた後、８時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート３６０ｍｌで再結晶して、前記化合物１７（９．９７ｇ、収率：６２％）を製造した。 Preparation Example 17 Synthesis of Compound 17 Following Compound 17

The compound B-7 can be obtained by using B as a starting material and using Ar1 = terphenyl in step 3 of the reaction formula 1. Compound B-7 (10.0 g, 24.81 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (5.66 g, 23.11 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolved in 320 ml of xylene, add sodium tert-butoxide (2.62 g, 27.31 mmol) and add bis (tri-tert-butylphosphine) palladium (0) (0.11 g, 0.21 mmol) The mixture was heated and stirred for 8 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, xylene was concentrated under reduced pressure and recrystallized with 360 ml of ethyl acetate to produce Compound 17 (9.97 g, yield: 62%).

MS [M + H] ⁺ = 689

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝２−フェニルナフタレンを用いると、前記化合物Ｂ−９を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−９（１０．０ｇ、２２．０８ｍｍｏｌ）、Ｎ−フェニル−［１，１'−ビフェニル］−４−アミン（５．９５ｇ、２４．２８ｍｍｏｌ）をキシレン２７０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．６２ｇ、２７．３１ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１１ｇ、０．２１ｍｍｏｌ）を入れた後、１０時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート３７０ｍｌで再結晶して、前記化合物１８（１０．４２ｇ、収率：７２％）を製造した。 Preparation Example 18 Synthesis of Compound 18 Following Compound 18

The compound B-9 can be obtained by using B as a starting material and using Ar1 = 2-phenylnaphthalene in step 3 of the reaction formula 1. Compound B-9 (10.0 g, 22.08 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (5.95 g, 24.28 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolved in 270 ml of xylene, add sodium tert-butoxide (2.62 g, 27.31 mmol) and add bis (tri-tert-butylphosphine) palladium (0) (0.11 g, 0.21 mmol). The mixture was heated and stirred for 10 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, xylene was concentrated under reduced pressure and recrystallized with 370 ml of ethyl acetate to produce Compound 18 (10.42 g, yield: 72%).

MS [M + H] ⁺ = 663

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝フェニルを用いると、前記化合物Ａ−１を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−１（１０．０ｇ、３０．５８ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−［１，１'−ビフェニル］−２−アミン（１０．８０ｇ、３３．６４ｍｍｏｌ）をキシレン１８０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．８２ｇ、３９．７６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１６ｇ、０．３１ｍｍｏｌ）を入れた後、３時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート２５０ｍｌで再結晶して、前記化合物１９（１４．７２ｇ、収率：７８％）を製造した。 <Production Example 19> Synthesis of Compound of the Following Compound 19

The compound A-1 can be obtained by using A as a starting material and using Ar1 = phenyl in step 3 of the reaction formula 1. Compound A-1 (10.0 g, 30.58 mmol), N-([1,1′-biphenyl] -4-yl)-[1,1′-biphenyl]-in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving 2-amine (10.80 g, 33.64 mmol) in 180 ml of xylene, sodium tert-butoxide (3.82 g, 39.76 mmol) is added and bis (tri-tert-butylphosphine) palladium ( 0) (0.16 g, 0.31 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 250 ml of ethyl acetate to produce the above compound 19 (14.72 g, yield: 78%).

MS [M + H] ⁺ = 613

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝フェニルを用いると、前記化合物Ｂ−１を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−１（１０．０ｇ、３０．５８ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−［１，１'−ビフェニル］−２−アミン（１０．８０ｇ、３３．６４ｍｍｏｌ）をキシレン２２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．８２ｇ、３９．７６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１６ｇ、０．３１ｍｍｏｌ）を入れた後、５時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、エチルアセテート２７０ｍｌで再結晶して、前記化合物２０（１４．７２ｇ、収率：７８％）を製造した。 Preparation Example 20 Synthesis of Compound of the Following Compound 20

The compound B-1 can be obtained by using B as a starting material and using Ar1 = phenyl in step 3 of the reaction formula 1. Compound B-1 (10.0 g, 30.58 mmol), N-([1,1′-biphenyl] -4-yl)-[1,1′-biphenyl]-in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving 2-amine (10.80 g, 33.64 mmol) in 220 ml of xylene, sodium tert-butoxide (3.82 g, 39.76 mmol) is added and bis (tri-tert-butylphosphine) palladium ( 0) (0.16 g, 0.31 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 270 ml of ethyl acetate to produce the above compound 20 (14.72 g, yield: 78%).

MS [M + H] ⁺ = 613

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝４−ビフェニルを用いると、前記化合物Ａ−２を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−２（１０．０ｇ、２４．８１ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−［１，１'−ビフェニル］−２−アミン（８．７６ｇ、２７．３０ｍｍｏｌ）をキシレン２７０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．１０ｇ、３２．２６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１３ｇ、０．２５ｍｍｏｌ）を入れた後、５時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン２３０ｍｌで再結晶して、前記化合物２１（１４．３３ｇ、収率：８３％）を製造した。 Preparation Example 21 Synthesis of Compound of the Following Compound 21

The compound A-2 can be obtained by using A as a starting material and using Ar1 = 4-biphenyl in step 3 of the reaction formula 1. Compound A-2 (10.0 g, 24.81 mmol), N-([1,1′-biphenyl] -4-yl)-[1,1′-biphenyl]-in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving 2-amine (8.76 g, 27.30 mmol) in 270 ml of xylene, sodium tert-butoxide (3.10 g, 32.26 mmol) is added and bis (tri-tert-butylphosphine) palladium ( 0) (0.13 g, 0.25 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to normal temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 230 ml of tetrahydrofuran to produce the aforementioned compound 21 (14.33 g, yield: 83%).

MS [M + H] ⁺ = 689

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝４−ビフェニルを用いると、前記化合物Ｂ−２を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−２（１０．０ｇ、２４．８１ｍｍｏｌ）、Ｎ−（［１，１'−ビフェニル］−４−イル）−［１，１'−ビフェニル］−２−アミン（８．７６ｇ、２７．３０ｍｍｏｌ）をキシレン２７０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（３．１０ｇ、３２．２６ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１３ｇ、０．２５ｍｍｏｌ）を入れた後、４時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン２３０ｍｌで再結晶して、前記化合物２２（１１．５１ｇ、収率：６７％）を製造した。 Preparation Example 22 Synthesis of Compound of the Following Compound 22

The compound B-2 can be obtained by using B as a starting material and using Ar1 = 4-biphenyl in step 3 of the reaction formula 1. Compound B-2 (10.0 g, 24.81 mmol), N-([1,1′-biphenyl] -4-yl)-[1,1′-biphenyl]-in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolving 2-amine (8.76 g, 27.30 mmol) in 270 ml of xylene, sodium tert-butoxide (3.10 g, 32.26 mmol) is added and bis (tri-tert-butylphosphine) palladium ( 0) (0.13 g, 0.25 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to normal temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 230 ml of tetrahydrofuran to produce the above-mentioned compound 22 (11.51 g, yield: 67%).

MS [M + H] ⁺ = 689

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝２−フルオレンを用いると、前記化合物Ａ−１５を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−１５（１０．０ｇ、２２．５７ｍｍｏｌ）、ジ（［１，１'−ビフェニル］−４−イル）アミン（７．９７ｇ、２４．８３ｍｍｏｌ）をキシレン２００ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．８２ｇ、２９．３５ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１２ｇ、０．２３ｍｍｏｌ）を入れた後、４時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン２２０ｍｌで再結晶して、前記化合物２３（１０．７８ｇ、収率：６６％）を製造した。 <Production Example 23> Synthesis of Compound of the Following Compound 23

The compound A-15 can be obtained by using A as a starting material and using Ar1 = 2-fluorene in step 3 of the reaction formula 1. Compound A-15 (10.0 g, 22.57 mmol) and di ([1,1'-biphenyl] -4-yl) amine (7.97 g, 24.83 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolved in 200 ml of xylene, add sodium tert-butoxide (2.82 g, 29.35 mmol) and add bis (tri-tert-butylphosphine) palladium (0) (0.12 g, 0.23 mmol). The mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 220 ml of tetrahydrofuran to produce the aforementioned compound 23 (10.78 g, yield: 66%).

MS [M + H] ⁺ = 729

前記反応式１のｓｔｅｐ３において、出発物質としてＡを用い、Ａｒ１＝２−９−フェニル−９Ｈ−カルバゾールを用いると、前記化合物Ａ−２１を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ａ−２１（１０．０ｇ、２０．３３ｍｍｏｌ）、９，９−ジメチル−Ｎ−フェニル−９Ｈ−フルオレン−２−アミン（６．３７ｇ、２２．３６ｍｍｏｌ）をキシレン２２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．５４ｇ、２６．４２ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１０ｇ、０．２０ｍｍｏｌ）を入れた後、４時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン２６０ｍｌで再結晶して、前記化合物２４（１１．５９ｇ、収率：７７％）を製造した。 Preparation Example 24 Synthesis of Compound of the Following Compound 24

The compound A-21 can be obtained by using A as a starting material and using Ar1 = 2-9-phenyl-9H-carbazole in step 3 of the reaction formula 1. Compound A-21 (10.0 g, 20.33 mmol) and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (6.37 g, 22.36 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere Is completely dissolved in 220 ml of xylene, then sodium tert-butoxide (2.54 g, 26.42 mmol) is added, and bis (tri-tert-butylphosphine) palladium (0) (0.10 g, 0.20 mmol) is added. After putting, it heat-stirred for 4 hours. The temperature was lowered to room temperature, and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 260 ml of tetrahydrofuran to produce the aforementioned compound 24 (11.59 g, yield: 77%).

MS [M + H] ⁺ = 742

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝２−フルオレンを用いると、前記化合物Ｂ−１５を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−１５（１０．０ｇ、２２．５７ｍｍｏｌ）、ジ（［１，１'−ビフェニル］−４−イル）アミン（７．９７ｇ、２４．８３ｍｍｏｌ）をキシレン２２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．８２ｇ、２９．３５ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１２ｇ、０．２３ｍｍｏｌ）を入れた後、３時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン２００ｍｌで再結晶して、前記化合物２５（８．６６ｇ、収率：５５％）を製造した。 <Production example 25> Synthesis of the compound of the following compound 25

The compound B-15 can be obtained by using B as a starting material and using Ar1 = 2-fluorene in step 3 of the reaction formula 1. Compound B-15 (10.0 g, 22.57 mmol) and di ([1,1'-biphenyl] -4-yl) amine (7.97 g, 24.83 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere After completely dissolved in 220 ml of xylene, add sodium tert-butoxide (2.82 g, 29.35 mmol) and add bis (tri-tert-butylphosphine) palladium (0) (0.12 g, 0.23 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature and the salt was removed by filtration, and then xylene was concentrated under reduced pressure and recrystallized with 200 ml of tetrahydrofuran to produce the aforementioned compound 25 (8.66 g, yield: 55%).

MS [M + H] ⁺ = 729

前記反応式１のｓｔｅｐ３において、出発物質としてＢを用い、Ａｒ１＝２−９−フェニル−９Ｈ−カルバゾールを用いると、前記化合物Ｂ−２１を得ることができる。窒素雰囲気下、５００ｍｌの丸底フラスコに化合物Ｂ−２１（１０．０ｇ、２０．３３ｍｍｏｌ）、９，９−ジメチル−Ｎ−フェニル−９Ｈ−フルオレン−２−アミン（６．３７ｇ、２２．３６ｍｍｏｌ）をキシレン２２０ｍｌに完全に溶かした後、ソジウムｔｅｒｔ−ブトキシド（２．５４ｇ、２６．４２ｍｍｏｌ）を添加し、ビス（トリ−ｔｅｒｔ−ブチルホスフィン）パラジウム（０）（０．１０ｇ、０．２０ｍｍｏｌ）を入れた後、３時間加熱撹拌した。常温に温度を下げて、濾過して塩を除去した後、キシレンを減圧濃縮させ、テトラヒドロフラン２３５ｍｌで再結晶して、前記化合物２６（１０．４４ｇ、収率：６９％）を製造した。 Preparation Example 26 Synthesis of Compound of the Following Compound 26

The compound B-21 can be obtained by using B as a starting material and using Ar 1 = 2-9-phenyl-9H-carbazole in step 3 of the reaction formula 1. Compound B-21 (10.0 g, 20.33 mmol) and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (6.37 g, 22.36 mmol) in a 500 ml round bottom flask under a nitrogen atmosphere Is completely dissolved in 220 ml of xylene, then sodium tert-butoxide (2.54 g, 26.42 mmol) is added, and bis (tri-tert-butylphosphine) palladium (0) (0.10 g, 0.20 mmol) is added. After charging, the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the salt was removed by filtration, xylene was concentrated under reduced pressure and recrystallized with 235 ml of tetrahydrofuran to produce the aforementioned compound 26 (10.44 g, yield: 69%).

MS [M + H] ⁺ = 742

<Experimental Example 1-1>
A glass substrate thin film coated with ITO (indium tin oxide) to a thickness of 1,000 Å was placed in detergent-dissolved distilled water and subjected to ultrasonic cleaning. At this time, a Fischer (Fischer Co.) product was used as a detergent, and distilled water secondary filtered with a filter (filter) of a Millipore (Millipore Co.) product was used as distilled water. After the ITO was washed for 30 minutes, ultrasonic cleaning was allowed to proceed for 10 minutes twice with distilled water. After completion of the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol for drying, and then transported to a plasma washing machine. After cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporation machine.

On the ITO transparent electrode thus prepared, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

The following compound 4-4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 Å), which is a substance that transports holes, is vacuum deposited on the hole injection layer to obtain positive A hole transport layer was formed.

Next, on the hole transporting layer, the following compound 1 was vacuum deposited to a film thickness of 100 Å to form an electron blocking layer.

Next, on the electron blocking layer, BH and BD were vacuum deposited at a film thickness of 300 Å at a weight ratio of 25: 1 to form a light emitting layer.

  The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer to a thickness of 300 Å. Lithium fluoride (LiF) was deposited to a thickness of 12 Å and aluminum was deposited to a thickness of 2,000 Å on the electron injection and transport layer to form a cathode.

In the above process, the deposition rate of the organic substance is maintained at 0.4 to 0.7 Å / sec, the lithium fluoride of the cathode is maintained at 0.3 Å / sec, and the deposition rate of aluminum is maintained at 2 Å / sec. The organic light emitting device was manufactured while maintaining a degree of 2 × 10 ^{−7 to} 5 × 10 ⁻⁶ torr.

<Experimental Example 1-2>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 2 was used instead of the compound 1 in Experimental Example 1-1.

<Experimental Example 1-3>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 3 was used instead of the compound 1 in Experimental Example 1-1.

Experimental Example 1-4
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 4 was used instead of the compound 1 in Experimental Example 1-1.

Experimental Example 1-5
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 6 was used instead of the compound 1 in Experimental Example 1-1.

Experimental Example 1-6
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 8 was used instead of the compound 1 in Experimental Example 1-1.

Experimental Example 1-7
An organic light emitting device was manufactured in the same manner as in Experimental Example 1 except that the compound 9 was used instead of the compound 1 in Experimental Example 1-1.

<Experimental Example 1-8>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 10 was used instead of the compound 1 in Experimental Example 1-1.

Experimental Example 1-9
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 12 was used instead of the compound 1 in Experimental Example 1-1.

<Experimental Example 1-10>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 15 was used instead of the compound 1 in Experimental Example 1-1.

<Experimental Example 1-11>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 17 was used instead of the compound 1 in Experimental Example 1-1.

<Experimental Example 1-12>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 22 was used instead of the compound 1 in Experimental Example 1-1.

<Experimental Example 1-13>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 23 was used instead of the compound 1 in Experimental Example 1-1.

Experimental Example 1-14
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound 24 was used instead of the compound 1 in Experimental Example 1-1.

Comparative Example 1
An organic light emitting diode was manufactured in the same manner as in Experimental Example 1-1 except that the compound of the following EB1 was used instead of the compound 1 in Experimental example 1-1.

Comparative Example 2
An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the following compound EB2 was used instead of compound 1 in Experimental Example 1-1.

Comparative Example 3
An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the compound of the following EB3 was used instead of the compound 1 in Experimental example 1-1.

Comparative Example 4
An organic light emitting diode was manufactured in the same manner as in Experimental Example 1-1 except that the compound of the following EB4 was used instead of the compound 1 in Experimental example 1-1.

When current was applied to the organic light emitting devices manufactured by Experimental Examples 1-1 to 14 and Comparative Examples 1 to 4, the results in Table 1 were obtained.

  As is apparent from Table 1 above, an organic light emitting device manufactured using the compound of the present invention as an electron blocking layer is Comparative Example 1 in which a substituent is linked to another position of the core of the present invention, and as a linker The compound of the present invention plays a role of electron blocking when compared with the case of using the materials of Comparative Examples 2 and 3 in which a phenyl group and a biphenyl group are substituted, so the efficiency, driving voltage and / or stability of the organic light emitting device It shows excellent characteristics in terms of sex.

  In Experimental Examples 1-1 to 1-14, the voltage decreases by 10% to 12% and the efficiency is 10% or more higher than the comparative example.

  As shown in the results of Table 1, it was possible to confirm that the compound according to the present invention has excellent electron blocking ability and is applicable to an organic light emitting device.

<Experimental Example 2-1 to 2-14>
The same experiment was conducted except that the following EB5 substance was used as the electron blocking layer in Experimental Example 1-1 and the compounds of Experimental Examples 1-1 to 1-14 were used instead of NPB as the hole transport layer. did.

Comparative Example 5
An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that the following HT1 compound was used instead of Compound 1 in Experimental Example 2-1.

Comparative Example 6
An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that the following HT2 compound was used instead of Compound 1 in Experimental Example 2-1.

When current was applied to the organic light emitting devices manufactured by Experimental Examples 2-1 to 2-14 and Comparative Examples 5 and 6, the results in Table 2 were obtained.

  As apparent from Table 2 above, an organic light emitting device manufactured using the compound of the present invention as a hole transport layer is a comparative example in which a substituent is linked to another position of the core of the present invention, phenyl as a linker The compound of the present invention plays a role of hole transport when compared with the case of using the substances of Comparative Examples 5 and 6 in which the group and the biphenyl group are substituted, so the efficiency, driving voltage and / or stability of the organic light emitting device It shows excellent characteristics in terms of sex.

  Specifically, in the experimental examples 2-1 to 2-14, the voltage decreases by 10% or more and the efficiency is 7 to 10% or more higher than the comparative example.

  As shown in the results of Tables 1 and 2, it was possible to confirm that the compound according to the present invention is excellent not only in the electron blocking ability but also in the hole transporting ability and is applicable to the organic light emitting device.

  Although the preferred embodiments (electron blocking layer and hole transport layer) of the present invention have been described above, the present invention is not limited thereto, and various modifications may be made within the scope of the claims and the detailed description of the invention. It is possible to implement in a modified form, which also belongs to the category of the invention.

1: Substrate 2: Anode 3: Light emitting layer 4: Cathode 5: Hole injection layer 6: Hole transport layer 7: Light emitting layer 8: Electron transport layer

Claims (15)

Nitrogen-containing compounds represented by the following chemical formula 1:
[Chemical formula 1]

In the above Chemical Formula 1,
R 1, R 2 and R 7 are the same or different from each other and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or not A substituted heterocyclic group,
Groups in which R3 and R4 combine to form a ring, or R5 and R6 combine to form a ring and do not form a ring are as defined in R1, R2 and R7,
L 1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar _{1 to} Ar ₃ are the same or different from each other, each independently a nitro group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl An amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group. The nitrogen-containing compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2 or 3.
[Chemical formula 2]

[Chemical formula 3]

In the above formulas 2 and 3,
R 1 to R 7, L 1 and Ar _{1 to} Ar ₃ are the same as defined in Chemical Formula 1,
R11 to R18 are the same as the definitions of R1, R2 and R7. The nitrogen-containing compound according to claim 1, wherein in the chemical formula 1, -L 1 -Ar ₁ is selected from the following structural formulas:

The nitrogen-containing compound according to claim 1, wherein in the chemical formula 1, -N (Ar ₂ Ar ₃ ) is selected from the following structural formulas:

  The nitrogen-containing compound according to claim 1, wherein the L1 is a direct bond.   The nitrogen-containing compound according to claim 1, wherein L1 is a substituted or unsubstituted arylene group.   L 1 is a phenylene group; a biphenylylene group; a bivalent terphenyl group; a bivalent quaternary phenyl group; a naphthalene group; a bivalent anthracene group; a bivalent fluorene group; a bivalent phenanthrene group; a bivalent pyrene group The nitrogen-containing compound according to claim 1, which is a divalent triphenylene group.   The nitrogen-containing compound according to claim 1, wherein the L1 is a heteroarylene group.   L 1 represents a divalent phenothiazine group; a divalent phenoxazine group; a divalent carbazole group; a divalent benzocarbazole group; a divalent benzimidazole group; a divalent thiophene group; A divalent furan group; a divalent dibenzofuran group; a divalent dibenzothiophene group; a divalent triazine group; a divalent pyridine group; a divalent pyrimidine group; a divalent quinoline group; or a divalent quinazoline group The nitrogen-containing compound according to claim 1. R1, R2 and R7 are hydrogen,
The nitrogen-containing compound according to claim 1, wherein the group which does not form a ring among R3 and R4 or R5 and R6 is hydrogen. The nitrogen-containing compound according to claim 1, wherein the chemical formula 1 is selected from the following structural formulas:

  An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode An organic light-emitting device, wherein one or more of the organic layers contain the nitrogen-containing compound according to any one of claims 1 to 11.   The organic layer includes a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and hole transport, and the hole injection layer, the hole transport layer, or hole injection and hole transport The organic light-emitting device according to claim 12, wherein the layer to be simultaneously performed includes the nitrogen-containing compound.   The organic light emitting device according to claim 12, wherein the organic substance layer includes a light emitting layer, and the light emitting layer includes the nitrogen-containing compound.   The organic light emitting device according to claim 12, wherein the organic layer comprises an electron blocking layer, and the electron blocking layer comprises the nitrogen-containing compound.

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