JP6083282B2 - 4-Aminocarbazole compounds and uses thereof - Google Patents

Description

  The present invention relates to a novel 4-aminocarbazole compound and an organic EL device using the same.

  An organic EL element is a surface-emitting element in which an organic thin film is held between a pair of electrodes, and has features such as a thin and light weight, a high viewing angle, and a high-speed response, and is expected to be applied to various display elements. . Recently, some practical applications such as mobile phone displays have begun.

  The organic EL element uses light emitted when holes injected from the anode and electrons injected from the cathode are recombined in the light emitting layer, and the structure thereof is a hole transport layer, a light emitting layer, A multilayer stack type in which an electron transport layer and the like are stacked is the mainstream. Here, the charge transport layer such as the hole transport layer and the electron transport layer does not emit light by itself, but facilitates the injection of charges into the light emitting layer, and the charge injected into the light emitting layer or the light emitting layer. It plays the role of confining the energy of the generated excitons. Therefore, the charge transport layer plays a very important role in lowering the driving voltage and improving the light emission efficiency of the organic EL element.

  As the hole transport material, an amine compound having an appropriate ionization potential and hole transport ability is used, and 4,4′-bis [N- (1-naphthyl) -N-phenyl] biphenyl is used as such an amine compound. (Hereinafter abbreviated as NPD) is well known. However, the driving voltage and luminous efficiency of an element using NPD for the hole transport layer are not sufficiently good, and development of a new material has been demanded.

  Against this background, recently, materials having a carbazole ring introduced in the molecule have been reported. Specific examples include 3-aminocarbazole compounds (for example, see Patent Documents 1 and 2) and 2-aminocarbazole compounds (for example, see Patent Document 3).

  However, according to the measurement by the inventors, the 3-aminocarbazole compound has a lower ionization potential than NPD. The ionization potential of the material is an important physical property value that affects the characteristics of the organic EL element. In particular, when used for a hole transport layer adjacent to the light emitting layer, the ionization potential of the material greatly affects the light emission efficiency of the organic EL element. For example, when a material having a low ionization potential is used for the hole transport layer adjacent to the light emitting layer, the light emission efficiency of the organic EL element decreases due to exciplex formation with the light emitting material (see, for example, Non-Patent Document 1). For this reason, in an organic EL device using a 3-aminocarbazole compound for the hole transport layer, a sufficiently high luminous efficiency could not be obtained. A hole transporting material having an ionization potential as high as NPD or higher is desired.

  On the other hand, the 2-aminocarbazole compound had a moderately high ionization potential equivalent to or higher than that of NPD. However, since the energy gap between HOMO-LUMO is small in 2-aminocarbazole compound, the energy of electrons injected into the light-emitting layer and the energy of excitons generated in the light-emitting layer are effectively insufficiently confined. Luminous efficiency could not be obtained.

  That is, in order to obtain an organic EL device exhibiting higher luminous efficiency than before, there has been a demand for the development of a compound having a moderately high ionization potential equal to or higher than that of NPD and having a larger energy gap than the conventional compound.

JP 2006-151979 A JP 2006-298895 A KR2010-0071723

Journal of Physical Chemistry C, 2008, 112, 7735

  The present invention has been made in view of the above-described background art, and has an object of having a reasonably high ionization potential and a larger energy gap than a conventionally known compound, and being excellent in luminous efficiency in an organic EL device. It is to provide a compound.

  As a result of intensive studies, the present inventors have found that the novel 4-aminocarbazole compound represented by the following general formula (1) has an appropriate ionization potential and has a larger energy gap than a conventionally known compound. . Moreover, it discovered that the luminous efficiency of the organic EL element which used this compound for the positive hole transport layer was excellent, and came to complete this invention.

(In the formula, Ar ^{1 to} Ar ³ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom or sulfur atom). [These groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear or branched chain having 3 to 18 carbon atoms. Or a cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a carbon number 1 to a substituent selected from the group consisting of a heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom. Species Represents an even or 'have.
Ar ⁴ is an aromatic hydrocarbon group having 6 to 17 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom, nitrogen atom, or sulfur atom. A methyl group, an ethyl group, a C3-C18 linear, branched or cyclic alkyl group, a methoxy group, an ethoxy group, a C3-C18 linear, branched or cyclic alkoxy group, a carbon number 1 to 3 halogenated alkyl groups, 1 to 3 halogenated alkoxy groups, 6 to 12 aryl groups, 6 to 18 aryloxy groups, 3 to 20 heteroaryl groups, carbon It may have one or more substituents selected from the group consisting of a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom] The Represent.
X is a bivalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, 18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C1-C3 halogenated alkyl group, carbon number 1 ~ 3 halogenated alkoxy group, C6-12 aryl group, C6-18 aryloxy group, C3-20 heteroaryl group, C3-18 trialkylsilyl group, carbon number It may have one or more substituents selected from the group consisting of 18 to 40 triarylsilyl groups, cyano groups, halogen atoms, and deuterium atoms].
R ^{1 to} R ⁷ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, ethyl group, Group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, and a halogenated group having 1 to 3 carbon atoms You may have 1 or more types of substituents chosen from the group which consists of an alkyl group, a C6-C20 aryl group, a C3-C20 heteroaryl group, a cyano group, a halogen atom, and a deuterium atom. ], Methyl group, ethyl group, linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group, ethoxy group, linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, carbon number 1 to 3 halogenated alkyl groups, Aryloxy group prime 6-18 represents a trialkylsilyl group having 3 to 18 carbon atoms, triarylsilyl group of 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom. )
That is, the present invention relates to a 4-aminocarbazole compound represented by the above general formula (1) and its use.

  The organic EL device using the 4-aminocarbazole compound of the present invention showed higher luminous efficiency (current efficiency) than conventional carbazole compounds, and was able to keep the driving voltage low.

  Therefore, according to the present invention, it is possible to provide an organic EL element with low voltage, high luminance, high durability, and high efficiency.

  Hereinafter, the present invention will be described in detail.

  General formula (1) of the present invention

In the 4-aminocarbazole compound represented by the formula ( ¹⁾ , Ar ^{1 to} Ar ³ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms, or at least one oxygen atom or sulfur atom containing 3 carbon atoms. -20 heteroaromatic groups [these groups are each independently a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a carbon number of 3 -18 linear, branched or cyclic alkoxy group, C1-C3 halogenated alkyl group, C1-C3 halogenated alkoxy group, C6-C20 aryl group, C6-C18 Aryloxy group, heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, triarylsilyl group having 18 to 40 carbon atoms, cyano group, halogen atom, and deuterium A substituent selected from the group consisting of children representing the a may be] 1 or more.

The aromatic hydrocarbon group having 6 to 20 carbon atoms in Ar ¹ to Ar ^3, although not particularly limited, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, benzofluorenyl Group, dibenzofluorenyl group, phenanthryl group, fluoranthenyl group, anthryl group, chrycenyl group, pyrenyl group, triphenylene group, perylenyl group and the like.

The at least one oxygen atom or hetero-aromatic groups of 3 to 20 carbon atoms containing a sulfur atom in Ar ¹ to Ar ^3, although not particularly limited, for example, thienyl group, furyl group, thiazolyl group, isothiazolyl Group, oxazolyl group, isoxazolyl group, benzothienyl group, benzofuranyl group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzoisoxazolyl group, 2 1,3-benzooxadiazolyl group, dibenzothienyl group, dibenzofuranyl group, phenoxazinyl group, phenothiazinyl group, thiantenyl group and the like.

The substitution which may be substituted by the C6-C20 aromatic hydrocarbon group or the C3-C20 heteroaromatic group containing at least one oxygen atom or sulfur atom in Ar < ¹ > -Ar < ³ > below. Group (methyl group, ethyl group, C3-C18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, carbon number 1 to 3 halogenated alkyl groups, 1 to 3 halogenated alkoxy groups, 6 to 20 aryl groups, 6 to 18 aryloxy groups, 3 to 20 heteroaryl groups, carbon A substituent selected from the group consisting of a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom will be described.

  Examples of the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms include, but are not limited to, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, and pentyl group. Hexyl group, heptyl group, octyl group, stearyl group, cyclopropyl group, cyclohexyl group and the like.

  The linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms is not particularly limited, and examples thereof include a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a tert-butoxy group. , A pentyloxy group, a hexyloxy group, a stearyloxy group, and the like.

  Although it does not specifically limit as a C1-C3 halogenated alkyl group, For example, a trifluoromethyl group, a trichloromethyl group, 2-fluoroethyl group etc. are mentioned.

  Although it does not specifically limit as a C1-C3 halogenated alkoxy group, For example, a trifluoromethoxy group, a trichloromethoxy group, 2-fluoroethoxy group etc. are mentioned.

  The aryl group having 6 to 20 carbon atoms is not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2-methoxyphenyl group, and a 3-methoxy group. Phenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,4-dimethylphenyl group, 2,6-dimethylphenyl group, biphenyl group, naphthyl group, 1 -Methylnaphthyl group, 2-methylnaphthyl group, phenanthryl group, 9,9-dimethylfluorenyl group and the like can be exemplified.

  Although it does not specifically limit as a C6-C18 aryloxy group, For example, a phenoxy group, 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2-methoxyphenoxy group, 3 -Methoxyphenoxy group, 4-methoxyphenoxy group, 2-cyanophenoxy group, 3-cyanophenoxy group, 4-cyanophenoxy group, 3,4-dimethylphenoxy group, 2,6-dimethylphenoxy group, biphenyloxy group, naphthyl An oxy group etc. are mentioned.

  Although it does not specifically limit as C3-C20 heteroaryl group, For example, pyrrolyl group, 1-methylpyrrolyl group, 1-phenylpyrrolyl group, thienyl group, 2-methylthienyl group, 2-cyanothienyl Group, 2-phenylthienyl group, furyl group, 2-phenylfuryl group, imidazolyl group, 1-methylimidazolyl group, 2-methylimidazolyl group, 1-phenylimidazolyl group, 2-phenyl-imidazolyl group, pyrazolyl group, thiazolyl group , Isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, 2,4-diphenyl-1,3,5-triazyl group, indolyl group, benzothienyl group, Benzofuranyl group, benzimidazolyl group, 2-methylbenzimidazolyl 2-phenylbenzimidazolyl group, 1-methylbenzimidazolyl group, 1-phenylbenzimidazolyl group, 1,2-diphenylbenzimidazolyl group, indazolyl group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group , Benzoxazolyl group, benzisoxazolyl group, 2,1,3-benzoxiadiazolyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolyl group, carbazolyl group, 9-methylcarbazolyl group, 9 -Ethylcarbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, dibenzofuranyl group, phenoxazinyl group, phenothiazinyl group, acridinyl group, phenanthroline group, phenazine group, thiantenyl group and the like.

  Although it does not specifically limit as a C3-C18 trialkylsilyl group, For example, a trimethylsilyl group, a triethylsilyl group, a tributylsilyl group etc. are mentioned.

  The triarylsilyl group having 18 to 40 carbon atoms is not particularly limited, and examples thereof include a triphenylsilyl group, a tri (2-methylphenyl) silyl group, a tri (3-methylphenyl) silyl group, and a tri ( 4-methylphenyl) silyl group, tri (4-biphenylyl) silyl group, and the like.

  Examples of the halogen atom include fluorine, chlorine, bromine, or iodine.

Specific examples of Ar ^{1 to} Ar ³ include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4-n-decylphenyl group, 4-n- Dodecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-tritylphenyl group, 3-trityl group Enyl group, 4-triphenylsilylphenyl group, 3-triphenylsilylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group 2-methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2- Isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphe Group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxy Phenyl group, 2- (2-ethylbutyl) oxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3-methyl -4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl 5-methoxyphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl Group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2 -Methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 3-cyanophenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-di Fluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 4-biphenyl group, 3-biphenyl group, 2-biphenyl group, 2-methyl-1,1′-biphenyl-4-yl group, 3-methyl-1,1′-biphenyl-4-yl group, 2′-methyl-1,1′-biphenyl-4-yl group, 3′-methyl-1,1′-biphenyl-4-yl group, 4'-methyl-1,1'-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl-4-yl group, 2,2'-dimethyl-1,1'-biphenyl-4 -Yl group, 2,3'-dimethyl-1,1'-biphenyl-4-yl group, 2,4'-dimethyl-1,1'-biphenyl-4-yl group, 3,2'-dimethyl-1 , 1′-biphenyl-4-yl group, 2 ′, 3′-dimethyl-1,1′-biphenyl-4-yl group, 2 ′, 4′-dimethyl-1,1′-biphenyl-4-yl group, 2 ′, 5′-dimethyl-1,1′-biphenyl-4-yl group, 2 ′, 6′-dimethyl-1, 1′-biphenyl-4-yl group, p-terphenyl group, m-terphenyl group, o-terphenyl group, 1-naphthyl group, 2-naphthyl group, 2-methylnaphthalen-1-yl group, 4- Methylnaphthalen-1-yl group, 6-methylnaphthalen-2-yl group, 4- (1-naphthyl) phenyl group, 4- (2-naphthyl) phenyl group, 3- (1-naphthyl) phenyl group, 3- (2-naphthyl) phenyl group, 3-methyl-4- (1-naphthyl) phenyl group, 3-methyl-4- (2-naphthyl) phenyl group, 4- (2-methylnaphthalen-1-yl) phenyl group , 3- (2-methylnaphthalen-1-yl) phenyl group, -Phenylnaphthalen-1-yl group, 4- (2-methylphenyl) naphthalen-1-yl group, 4- (3-methylphenyl) naphthalen-1-yl group, 4- (4-methylphenyl) naphthalene-1 -Yl group, 6-phenylnaphthalen-2-yl group, 4- (2-methylphenyl) naphthalen-2-yl group, 4- (3-methylphenyl) naphthalen-2-yl group, 4- (4-methyl) Phenyl) naphthalen-2-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diethyl-2-fluorenyl group, 9,9-di-n-propyl-2-fluorenyl group 9,9-di-n-octyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9′-spirobifluorenyl group, 9-phenanthryl group, 2-phenane Ryl group, 11,11′-dimethylbenzo [a] fluoren-9-yl group, 11,11′-dimethylbenzo [a] fluoren-3-yl group, 11,11′-dimethylbenzo [b] fluorene-9 -Yl group, 11,11'-dimethylbenzo [b] fluoren-3-yl group, 11,11'-dimethylbenzo [c] fluoren-9-yl group, 11,11'-dimethylbenzo [c] fluorene- 2-yl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 1-pyrenyl group, 2-pyrenyl group, 9-anthryl group, 2-anthryl group, 2-triphenylene group, 3-chrysenyl group, 6 -Chrysenyl group, 3-perylenyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2- Xazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7- Benzothiazolyl group, 3-benzoisothiazolyl group, 4-benzisothiazolyl group, 5-benzoisothiazolyl group, 6-benzoisothiazolyl group, 7-benzisothiazolyl group, 2,1,3-benzo Thiadiazol-4-yl group, 2,1,3-benzothiadiazol-5-yl group, 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl Group, 7-benzoxazolyl group, 3-benzisoxazolyl group, 4-benzisoxazolyl group 5-benzoisoxazolyl group, 6-benzoisoxazolyl group, 7-benzisoxazolyl group, 2,1,3-benzooxadiazolyl-4-yl group, 2,1,3- Benzooxadiazolyl-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group, 2-furanyl group, 3 -Furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group, 2-thianthryl group, 10-phenylphenothiazin-3-yl group, 10-phenylphenothiazine-2- Yl group, 10-phenylphenoxazin-3-yl group, 10-phenylphenoxazin-2-yl group, 4- (2-pyridyl) phenyl group, 4- (3- Lysyl) phenyl group, 4- (4-pyridyl) phenyl group, 3- (2-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (2- Phenylimidazol-1-yl) phenyl group, 4- (1-phenylimidazol-2-yl) phenyl group, 4- (2,3,4-triphenylimidazol-1-yl) phenyl group, 4- (1- Methyl-4,5-diphenylimidazol-2-yl) phenyl group, 4- (2-methylbenzimidazol-1-yl) phenyl group, 4- (2-phenylbenzimidazol-1-yl) phenyl group, 4- (1-methylbenzimidazol-2-yl) phenyl group, 4- (2-phenylbenzimidazol-1-yl) phenyl group, 3- (2-methylbenzimidazole) 1-yl) phenyl group, 3- (2-phenylbenzimidazol-1-yl) phenyl group, 3- (1-methylbenzimidazol-2-yl) phenyl group, 3- (2-phenylbenzimidazol-1- Yl) phenyl group, 4- (3,5-diphenyltriazin-1-yl) phenyl group, 4- (2-thienyl) phenyl group, 4- (2-furanyl) phenyl group, 5-phenylthiophen-2-yl Group, 5-phenylfuran-2-yl group, 4- (5-phenylthiophen-2-yl) phenyl group, 4- (5-phenylfuran-2-yl) phenyl group, 3- (5-phenylthiophene- 2-yl) phenyl group, 3- (5-phenylfuran-2-yl) phenyl group, 4- (2-benzothienyl) phenyl group, 4- (3-benzothienyl) phenyl group, 3- (2-benzothienyl) phenyl group, 3- (3-benzothienyl) phenyl group, 4- (2-dibenzothienyl) phenyl group, 4- (4-dibenzothienyl) phenyl group, 3- (2-dibenzo Thienyl) phenyl group, 3- (4-dibenzothienyl) phenyl group, 4- (2-dibenzofuranyl) phenyl group, 4- (4-dibenzofuranyl) phenyl group, 3- (2-dibenzofuranyl) phenyl Group, 3- (4-dibenzofuranyl) phenyl group, 4- (9-carbazolyl) phenyl group, 3- (9-carbazolyl) phenyl group and the like can be exemplified, but are not limited thereto. .

Ar ^{1 to} Ar ³ are each independently a phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, fluorenyl group, benzofluorenyl group, dibenzothienyl group because of excellent hole transport properties. Or a dibenzofuranyl group (these groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a carbon number of 3 to 18 linear, branched, or cyclic alkoxy groups, halogenated alkyl groups having 1 to 3 carbon atoms, aryl groups having 6 to 20 carbon atoms, aryloxy groups having 6 to 18 carbon atoms, heterogeneities having 3 to 20 carbon atoms A group consisting of an aryl group, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom. It may preferably have one or more selected substituents), and may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dibenzothienyl group, or a dibenzofuranyl group (these groups Each independently represents a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic group having 3 to 18 carbon atoms. An alkoxy group, a C1-C3 halogenated alkyl group, a C6-C20 aryl group, a C6-C18 aryloxy group, a C3-C20 heteroaryl group, a C3-C18 tri (It may have one or more substituents selected from the group consisting of alkylsilyl groups, triarylsilyl groups having 18 to 40 carbon atoms, cyano groups, halogen atoms, and deuterium atoms) More preferably, there are a phenyl group, 4-methylphenyl group, 3-methylphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 4- (4-dibenzothienyl) phenyl group, 4- (4-dibenzo). Furanyl) phenyl group, 4-biphenyl group, 3-biphenyl group, p-terphenyl group, m-terphenyl group, 1-naphthyl group, 2-naphthyl group, 9,9-dimethyl-2-fluorenyl group, 2 -It is more preferable that it is a dibenzothienyl group or a 2-dibenzofuranyl group.

In the 4-aminocarbazole compound represented by the general formula (1), Ar ⁴ is an aromatic hydrocarbon group having 6 to 17 carbon atoms, or at least one oxygen atom, nitrogen atom, or sulfur atom containing 3 carbon atoms. To 20 heteroaromatic groups (these groups are each independently a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a carbon number of 3). -18 linear, branched or cyclic alkoxy groups, C1-C3 halogenated alkyl groups, C1-C3 halogenated alkoxy groups, C6-C12 aryl groups, C6-C18 Aryloxy group, heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, triarylsilyl group having 18 to 40 carbon atoms, cyano group, halogen atom, and deuterium source It may have one or more substituents selected from the group consisting of children.

The aromatic hydrocarbon group having 6 to 17 carbon atoms in Ar ⁴ is not particularly limited, and examples thereof include a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, a phenanthryl group, and an anthryl group. , Pyrenyl group, or fluoranthenyl group.

The C3-C20 heteroaromatic group containing at least one oxygen atom, nitrogen atom, or sulfur atom in Ar ⁴ is not particularly limited, and examples thereof include a pyrrolyl group, a thienyl group, a furyl group, Imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrimidyl, pyrazyl, 1,3,5-triazyl, indolyl, benzothienyl, benzofuranyl, benzoimidazolyl, indazolyl Group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzoisoxazolyl group, 2,1,3-benzooxadiazolyl group, quinolyl group , Isoquinolyl group, quinoxalyl group, quinazolyl group, carba Examples include a zolyl group, a dibenzothienyl group, a dibenzofuranyl group, a phenoxazinyl group, a phenothiazinyl group, an acridinyl group, a phenanthroline group, a phenazine group, and a thiantenyl group.

Hereinafter, an aromatic hydrocarbon group or at least one oxygen atom 6-17 carbon atoms in the Ar ^4, nitrogen atoms, or may be substituted on heteroaromatic group having 3 to 20 carbon atoms containing a sulfur atom Substituents (methyl group, ethyl group, C3-C18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, carbon A halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, (Substituents selected from the group consisting of a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom).

Linear 3 to 18 carbon atoms in the Ar ^4, branch, or the alkyl group of cyclic, but not limited to, straight-chain having 3 to 18 carbon atoms shown in the above ^Ar 1 to Ar ^3, the branch Or the same substituent as the cyclic alkyl group.

Linear 3 to 18 carbon atoms in the Ar ^4, branched, or as a cyclic alkoxy group is not particularly limited, a straight-chain carbon atoms 3 to 18 shown in the above ^Ar 1 to Ar ^3, the branch Or the same substituent as the cyclic alkoxy group.

Examples of the halogenated alkyl group having 1 to 3 carbon atoms in the Ar ^4, is not particularly limited, include the same substituents as an alkyl halide group having 1 to 3 carbon atoms shown in Ar ¹ to Ar ³ of the It is done.

Examples of the halogenated alkoxy group having 1 to 3 carbon atoms in the Ar ^4, is not particularly limited, include the same substituents as halogenated alkoxy group having 1 to 3 carbon atoms shown in Ar ¹ to Ar ³ of the It is done.

The aryl group having 6 to 12 carbon atoms in Ar ⁴ is not particularly limited. 3-methoxyphenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 3,4-dimethylphenyl group, 2,6-dimethylphenyl group, biphenyl group, naphthyl Groups and the like.

Examples of the aryloxy group having 6 to 18 carbon atoms in the Ar ^4, is not particularly limited, the same substituent groups as aryloxy group having 6 to 18 carbon atoms shown in ^Ar 1 to Ar ³ of the.

The heteroaryl group having 3 to 20 carbon atoms in the Ar ^4, is not particularly limited, the same substituent groups as heteroaryl group having 3 to 20 carbon atoms shown in ^Ar 1 to Ar ³ of the.

The trialkylsilyl group having 3 to 18 carbon atoms in the Ar ^4, is not particularly limited, include the same substituents as trialkylsilyl group having a carbon number of 3 to 18 shown in ^Ar 1 to Ar ³ of the It is done.

The triarylsilyl group of 18 to 40 carbon atoms in the Ar ^4, is not particularly limited, include the same substituents as triaryl silyl group having a carbon number of 18 to 40 shown in ^Ar 1 to Ar ³ of the It is done.

As the halogen atom in Ar ^4, it is not particularly limited, include the same substituents as halogen atom shown in Ar ¹ to Ar ³ of the.

Specific examples of Ar ⁴ include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n -Propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 4-n -Pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-tritylphenyl group, 3-tritylphenyl group 4-triphenylsilylphenyl group, 3-triphenylsilylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2 , 6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2 -Methoxyphenyl group, 4-ethoxyphenyl group, 3-ethoxyphenyl group, 2-ethoxyphenyl group, 4-n-propoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2-isopropoxy group Phenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4 n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2-ethylbutyl) oxyphenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 4-cyclohexyloxy Phenyl group, 2-cyclohexyloxyphenyl group, 4-phenoxyphenyl group, 3-phenoxyphenyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3-methyl-4-methoxyphenyl Group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5- Toxiphenyl group, 2-methoxy-4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3, 4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6 -Ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 3-cyanophenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl Group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,6-difluorophenyl An phenyl group, a 3,4-difluorophenyl group, a 3,5-difluorophenyl group, a 4-biphenyl group, a 3-biphenyl group, a 2-biphenyl group, a 2-methyl-1,1′-biphenyl-4-yl group, 3-methyl-1,1′-biphenyl-4-yl group, 2′-methyl-1,1′-biphenyl-4-yl group, 3′-methyl-1,1′-biphenyl-4-yl group, 4'-methyl-1,1'-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl-4-yl group, 2,2'-dimethyl-1,1'-biphenyl-4 -Yl group, 2,3'-dimethyl-1,1'-biphenyl-4-yl group, 2,4'-dimethyl-1,1'-biphenyl-4-yl group, 3,2'-dimethyl-1 , 1′-biphenyl-4-yl group, 2 ′, 3′-dimethyl-1,1′-biphenyl-4-yl group, 2 ′, 4′- Dimethyl-1,1′-biphenyl-4-yl group, 2 ′, 5′-dimethyl-1,1′-biphenyl-4-yl group, 2 ′, 6′-dimethyl-1,1′-biphenyl-4 -Yl group, p-terphenyl group, m-terphenyl group, o-terphenyl group, 1-naphthyl group, 2-naphthyl group, 2-methylnaphthalen-1-yl group, 4-methylnaphthalen-1-yl Group, 6-methylnaphthalen-2-yl group, 4- (1-naphthyl) phenyl group, 4- (2-naphthyl) phenyl group, 3- (1-naphthyl) phenyl group, 3- (2-naphthyl) phenyl Group, 3-methyl-4- (1-naphthyl) phenyl group, 3-methyl-4- (2-naphthyl) phenyl group, 4- (2-methylnaphthalen-1-yl) phenyl group, 3- (2- Methylnaphthalen-1-yl) phenyl group, 4-phenyl Lunaphthalen-1-yl group, 4- (2-methylphenyl) naphthalen-1-yl group, 4- (3-methylphenyl) naphthalen-1-yl group, 4- (4-methylphenyl) naphthalene-1- Yl group, 6-phenylnaphthalen-2-yl group, 4- (2-methylphenyl) naphthalen-2-yl group, 4- (3-methylphenyl) naphthalen-2-yl group, 4- (4-methylphenyl) ) Naphthalen-2-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diethyl-2-fluorenyl group, 9,9-di-n-propyl-2-fluorenyl group, 9,9-di-n-octyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9′-spirobifluorenyl group, 9-phenanthryl group, 2-phenanthryl group, 11,11′-dimethylbenzo [a] fluoren-9-yl group, 11,11′-dimethylbenzo [a] fluoren-3-yl group, 11,11′-dimethylbenzo [b] fluoren-9-yl group 11,11′-dimethylbenzo [b] fluoren-3-yl group, 11,11′-dimethylbenzo [c] fluoren-9-yl group, 11,11′-dimethylbenzo [c] fluoren-2-yl Group, 3-fluoranthenyl group, 8-fluoranthenyl group, 1-pyrenyl group, 2-pyrenyl group, 9-anthryl group, 2-anthryl group, 1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl-3,4-dimethyl-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 2- (2-naphthyl) -3,4-dimethyl-1-imidazolyl group 2- (2-naphthyl) -3,4-diphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl group, 1-phenyl-2-imidazolyl group, 1-methyl- 4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dimethyl-2 -Imidazolyl group, 1-phenyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dibiphenylyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group Group, 1-methyl-4-pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-phenyl-5-pyrazolyl group, 2-thiol Zolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4- Isoxazolyl group, 5-isoxazolyl group, 2-pyridyl group, 3-methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 3 -Pyridyl group, 4-methyl-3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 2,2'-bipyridin-3-yl group, 2,2'-bipyridin-4-yl group, 2,2 '-Bipyridin-5-yl group, 2,3'-bipyridin-3-yl group, 2,3'-bipyridin-4-yl group, 2,3'-bipyridin-5-yl group, 5-pyrimidyl group, Pi Lazyl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazin-2-yl group, 1-benzimidazolyl group, 2-methyl-1-benzoimidazolyl group, 2-phenyl-1 -Benzimidazolyl group, 1-methyl-2-benzimidazolyl group, 1-phenyl-2-benzoimidazolyl group, 1-methyl-5-benzimidazolyl group, 1,2-dimethyl-5-benzimidazolyl group, 1-methyl-2-phenyl- 5-benzoimidazolyl group, 1-phenyl-5-benzimidazolyl group, 1,2-diphenyl-5-benzimidazolyl group, 1-methyl-6-benzoimidazolyl group, 1,2-dimethyl-6-benzimidazolyl group, 1-methyl-2 -Phenyl-6-benzimidazolyl group, 1-phenyl-6-benzimidazolyl group 1,2-diphenyl-6-benzimidazolyl group, 1-methyl-3-indazolyl group, 1-phenyl-3-indazolyl group, 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7 -Benzothiazolyl group, 3-benzisothiazolyl group, 4-benzisothiazolyl group, 5-benzoisothiazolyl group, 6-benzoisothiazolyl group, 7-benzisothiazolyl group, 2,1,3- Benzothiadiazol-4-yl group, 2,1,3-benzothiadiazol-5-yl group, 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxa Zolyl group, 7-benzoxazolyl group, 3-benzisoxazolyl group, 4-benzisoxazolyl group, 5-benzo Soxazolyl group, 6-benzoisoxazolyl group, 7-benzisoxazolyl group, 2,1,3-benzooxadiazolyl-4-yl group, 2,1,3-benzooxadiazolyl-5 Yl group, 2-quinolyl group, 3-quinolyl group, 5-quinolyl group, 6-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-quinoxalyl group, 3-phenyl-2-quinoxalyl Group, 6-quinoxalyl group, 2,3-dimethyl-6-quinoxalyl group, 2,3-diphenyl-6-quinoxalyl group, 2-quinazolyl group, 4-quinazolyl group, 2-acridinyl group, 9-acridinyl group, 1 , 10-phenanthroline-3-yl group, 1,10-phenanthroline-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-phenyl group, Nzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group, 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group, 9 -Methylcarbazol-2-yl group, 9-methylcarbazol-3-yl group, 9-methylcarbazol-4-yl group, 9-phenylcarbazol-2-yl group, 9-phenylcarbazol-3-yl group, 9 -Phenylcarbazol-4-yl group, 9-biphenylcarbazol-2-yl group, 9-biphenylcarbazol-3-yl group, 9-biphenylcarbazol-4-yl group, 2-thianthryl group, 10-phenylphenothiazine-3 -Yl group, 10-phenylphenothiazin-2-yl group, 10-phenylphenoxazine-3 Yl group, 10-phenylphenoxazin-2-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 9-phenylcarbazol-4-yl group, 1-methylindole-2 -Yl group, 1-phenylindol-2-yl group, 4- (2-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 4- (4-pyridyl) phenyl group, 3- (2-pyridyl) ) Phenyl group, 3- (3-pyridyl) phenyl group, 3- (4-pyridyl) phenyl group, 4- (2-phenylimidazol-1-yl) phenyl group, 4- (1-phenylimidazol-2-yl) ) Phenyl group, 4- (2,3,4-triphenylimidazol-1-yl) phenyl group, 4- (1-methyl-4,5-diphenylimidazol-2-yl) phenyl group 4- (2-methylbenzimidazol-1-yl) phenyl group, 4- (2-phenylbenzimidazol-1-yl) phenyl group, 4- (1-methylbenzimidazol-2-yl) phenyl group, 4- (2-phenylbenzimidazol-1-yl) phenyl group, 3- (2-methylbenzimidazol-1-yl) phenyl group, 3- (2-phenylbenzimidazol-1-yl) phenyl group, 3- (1 -Methylbenzimidazol-2-yl) phenyl group, 3- (2-phenylbenzimidazol-1-yl) phenyl group, 4- (3,5-diphenyltriazin-1-yl) phenyl group, 4- (2- Thienyl) phenyl group, 4- (2-furanyl) phenyl group, 5-phenylthiophen-2-yl group, 5-phenylfuran-2-yl group, 4- (5-phenylthiophen-2-yl) phenyl group, 4- (5-phenylfuran-2-yl) phenyl group, 3- (5-phenylthiophen-2-yl) phenyl group, 3- (5-phenylfuran) 2-yl) phenyl group, 4- (2-benzothienyl) phenyl group, 4- (3-benzothienyl) phenyl group, 3- (2-benzothienyl) phenyl group, 3- (3-benzothienyl) phenyl Group, 4- (2-dibenzothienyl) phenyl group, 4- (4-dibenzothienyl) phenyl group, 3- (2-dibenzothienyl) phenyl group, 3- (4-dibenzothienyl) phenyl group, 4- (2 -Dibenzofuranyl) phenyl group, 4- (4-dibenzofuranyl) phenyl group, 3- (2-dibenzofuranyl) phenyl group, 3- (4-dibenzofuranyl) phenyl group 5-phenylpyridin-2-yl group, 4-phenylpyridin-2-yl group, 5-phenylpyridin-3-yl group, 4- (9-carbazolyl) phenyl group, 3- (9-carbazolyl) phenyl group, etc. However, the present invention is not limited to these examples.

Ar ⁴ is a phenyl group, a biphenyl group, a naphthyl group, a dibenzothienyl group, or a dibenzofuranyl group (these groups are each independently a methyl group, an ethyl group, a carbon, A linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, C1-C3 halogenated alkoxy group, C6-C12 aryl group, C6-C18 aryloxy group, C3-C20 heteroaryl group, C3-C18 trialkylsilyl group And may have one or more substituents selected from the group consisting of a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom). A phenyl group, 4-methylphenyl group, 3-methylphenyl group, 4-cyanophenyl group, 3-cyanophenyl group, 4-biphenyl group, 2-naphthyl group, 3-dibenzothienyl group, or 3-dibenzofura. More preferred is a nyl group.

  In the 4-aminocarbazole compound represented by the general formula (1), X represents a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms or a divalent heteroaromatic group having 3 to 20 carbon atoms (these Each independently represents a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic group having 3 to 18 carbon atoms. Alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, 3 to 20 carbon atoms 1 or more types of substituents chosen from the group which consists of a heteroaryl group, a C3-C18 trialkylsilyl group, a C18-C40 triarylsilyl group, a cyano group, a halogen atom, and a deuterium atom May ).

  Although it does not specifically limit as a C6-C20 bivalent aromatic hydrocarbon group, A phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a phenylnaphthalene-diyl group, a binaphthylene group, a fluorene-diyl group Benzofluorene-diyl group, dibenzofluorene-diyl group, phenanthrene-diyl group, fluoranthene-diyl group, anthracene-diyl group, chrysene-diyl group, pyrene-diyl group, triphenylene-diyl group, or perylene-diyl group Can be mentioned.

  The divalent heteroaromatic group having 3 to 20 carbon atoms in X is not particularly limited, but pyrrole-diyl group, thiophene-diyl group, furan-diyl group, imidazole-diyl group, thiazole-diyl group, Isothiazole-diyl group, oxazole-diyl group, isoxazole-diyl group, pyridine-diyl group, pyrimidine-diyl group, pyrazine-diyl group, triazine-idyl group, indole-diyl group, benzothiophene-diyl group, benzofuran- Diyl group, benzimidazole-diyl group, benzothiazole-diyl group, benzoisothiazole-diyl group, 2,1,3-benzothiadiazole-diyl group, benzoxazole-diyl group, benzoisoxazole-diyl group, 2,1 , 3-Benzoxadiazole-diyl group Thienothiophene-diyl, dithienothiophene-diyl, benzodithiophene-diyl, quinoline-diyl, isoquinoline-diyl, quinoxaline-diyl, phenanthroline-diyl, dibenzothiophene-diyl, benzothienobenzothiophene -Diyl group, dibenzofuran-diyl group, carbazole-diyl group, phenoxazine-diyl group, phenothiazine-diyl group, thianthrene-diyl group, phenylthiophene-diyl group, diphenylthiophene-diyl group, phenylfuran-diyl group, diphenylfuran -Diyl group, bithiophene-diyl group, terthiophene-diyl group, phenylpyridine-diyl group, or bipyridine-diyl group.

  Hereinafter, a substituent (methyl group, ethyl group, carbon number 3) which may be substituted with a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms or a divalent heteroaromatic group having 3 to 20 carbon atoms in X. -18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C1-C3 halogenated alkyl group, carbon number 1 to 3 halogenated alkoxy groups, 6 to 12 aryl groups, 6 to 18 aryloxy groups, 3 to 20 heteroaryl groups, 3 to 18 trialkylsilyl groups, carbon (Substituents selected from the group consisting of triarylsilyl groups, cyano groups, halogen atoms, and deuterium atoms) represented by formulas 18 to 40 will be described.

Linear 3 to 18 carbon atoms in X, branched, or the alkyl group of cyclic, but are not particularly limited to, straight-chain carbon atoms 3 to 18 shown in ^Ar 1 to Ar ³ of the branching, Or the substituent same as a cyclic | annular alkyl group is mentioned.

Linear 3 to 18 carbon atoms in X, branched, or as a cyclic alkoxy group is not particularly limited, a straight-chain carbon atoms 3 to 18 shown in ^Ar 1 to Ar ³ of the branching, Or the same substituent as a cyclic alkoxy group is mentioned.

Examples of the halogenated alkyl group having 1 to 3 carbon atoms in X, is not particularly limited, include the same substituents as an alkyl halide group having 1 to 3 carbon atoms shown in Ar ¹ to Ar ³ of the .

Examples of the halogenated alkoxy group having 1 to 3 carbon atoms in X, is not particularly limited, include the same substituents as the halogenated alkoxy group having 1 to 3 carbon atoms shown in Ar ¹ to Ar ³ of the .

The aryl group having 6 to 12 carbon atoms in X, although not particularly limited, the same substituent group as the aryl group having 6 to 12 carbon atoms shown in the Ar ⁴ of the.

Examples of the aryloxy group having 6 to 18 carbon atoms in X, although not particularly limited, the same substituent groups as aryloxy group having 6 to 18 carbon atoms shown in Ar ¹ to Ar ³ of the.

Although it does not specifically limit as a C3-C20 heteroaryl group in X, The same substituent as the C3-C20 heteroaryl group shown in said Ar < ¹ > -Ar < ³ > is mentioned.

Although it does not specifically limit as a C3-C18 trialkylsilyl group in X, The same substituent as the C3-C18 trialkylsilyl group shown in said Ar < ¹ > -Ar < ³ > is mentioned. .

The triarylsilyl group of 18 to 40 carbon atoms in X, although not particularly limited, include the same substituents as triaryl silyl group having a carbon number of 18 to 40 shown in Ar ¹ to Ar ³ of the .

Although it does not specifically limit as a halogen atom in X, The same substituent as the halogen atom shown in said Ar < ¹ > -Ar < ³ > is mentioned.

Specific examples of X include 1,4-phenylene group, 2-methyl-1,4-phenylene group, 2-ethyl-1,4-phenylene group, 2-n-propyl-1,4-phenylene group, 2 -Isopropyl-1,4-phenylene group, 2-n-butyl-1,4-phenylene group, 2-n-hexyl-1,4-phenylene group, 2-n-octyl-1,4-phenylene group, 1 , 3-phenylene group, 5-methyl-1,3-phenylene group, 5-ethyl-1,3-phenylene group, 5-n-propyl-1,3-phenylene group, 5-isopropyl-1,3-phenylene Group, 5-n-butyl-1,3-phenylene group, 5-n-hexyl-1,3-phenylene group, 5-n-octyl-1,3-phenylene group, 2-methyl-1,3-phenylene Group, 2-ethyl-1,3-phenylene group, 4 Methyl-1,3-phenylene group, 4-ethyl-1,3-phenylene group, 1,2-phenylene group, 4-methyl-1,2-phenylene group, 4-ethyl-1,2-phenylene group, 4 -N-propyl-1,2-phenylene group, 4-isopropyl-1,2-phenylene group, 4-n-butyl-1,2-phenylene group, 4-n-hexyl-1,2-phenylene group, 4 -N-octyl-1,2-phenylene group, 3-methyl-1,2-phenylene group, 3-ethyl-1,2-phenylene group, 3,6-dimethyl-1,4-phenylene group, 3,6 -Diethyl-1,4-phenylene group, 3,6-di-n-butyl-1,4-phenylene group, 3,6-di-n-hexyl-1,4-phenylene group, 3,6-di- n-octyl-1,4-phenylene group, 2,3-dimethyl-1, -Phenylene group, 2,3-diethyl-1,4-phenylene group, 2-methoxy-1,4-phenylene group, 2-ethoxy-1,4-phenylene group, 2-n-propyloxy-1,4- Phenylene group, 2-isopropyloxy-1,4-phenylene group, 2-n-butoxy-1,4-phenylene group, 2-n-hexyloxy-1,4-phenylene group, 2-n-octyloxy-1 , 4-phenylene group, 5-methoxy-1,3-phenylene group, 5-ethoxy-1,3-phenylene group, 5-n-propyloxy-1,3-phenylene group, 5-isopropyloxy-1,3 -Phenylene group, 5-n-butoxy-1,3-phenylene group, 5-n-hexyloxy-1,3-phenylene group, 5-n-octyloxy-1,3-phenylene group, 2-methoxy-1 , 3-phenylene group, 2-ethoxy-1,3-phenylene group, 4-methoxy-1,3-phenylene group, 4-ethoxy-1,3-phenylene group, 4-methoxy-1,2-phenylene group, 4 -Ethoxy-1,2-phenylene group, 4-n-propyloxy-1,2-phenylene group, 4-isopropyloxy-1,2-phenylene group, 4-n-butoxy-1,2-phenylene group, 4 -N-hexyloxy-1,2-phenylene group, 4-n-octyloxy-1,2-phenylene group, 3-methoxy-1,2-phenylene group, 3-ethoxy-1,2-phenylene group, 3 , 6-Ditoxy-1,4-phenylene group, 3,6-diethoxy-1,4-phenylene group, 3,6-di-n-butoxy-1,4-phenylene group, 3,6-di-n- group Hexyloxy-1,4-fu Nylene group, 3,6-di-n-octyloxy-1,4-phenylene group, 2,3-dimethoxy-1,4-phenylene group, 2,3-diethoxy-1,4-phenylene group, 2-cyano -1,4-phenylene group, 5-cyano-1,3-phenylene group, 2-cyano-1,3-phenylene group, 4-cyano-1,3-phenylene group, 4-cyano-1,2-phenylene Group, 3-cyano-1,2-phenylene group, 3,6-dicyano-1,4-phenylene group, 2,3-dicyano-1,4-phenylene group, 2,5-dicyano-1,3-phenylene Group, 2,4-dicyano-1,3-phenylene group, 4,5-dicyano-1,3-phenylene group, 3,4-dicyano-1,2-phenylene group, 4,5-dicyano-1,2 -Phenylene group, 2-fluoro-1,4-phenylene 5-fluoro-1,3-phenylene group, 2-fluoro-1,3-phenylene group, 4-fluoro-1,3-phenylene group, 4-fluoro-1,2-phenylene group, 3-fluoro-1 , 2-phenylene group, 3,6-difluoro-1,4-phenylene group, 2,3-difluoro-1,4-phenylene group, 2,5-difluoro-1,3-phenylene group, 2,4-difluoro -1,3-phenylene group, 4,5-difluoro-1,3-phenylene group, 3,4-difluoro-1,2-phenylene group, 4,5-difluoro-1,2-phenylene group, 4,4 '-Biphenylene group, 3,4'-biphenylene group, 2,4'-biphenylene group, 3,3'-biphenylene group, 3,2'-biphenylene group, 2,2'-biphenylene group, 2-methyl-4 , 4′-biphenylene group, 3- Tyl-4,4′-biphenylene group, 2,2′-dimethyl-4,4′-biphenylene group, 3,3′-dimethyl-4,4′-biphenylene group, 2,3′-dimethyl-4,4 '-Biphenylene group, 3,5-dimethyl-4,4'-biphenylene group, 3,6-dimethyl-4,4'-biphenylene group, 2,5-dimethyl-4,4'-biphenylene group, 2,6 -Dimethyl-4,4'-biphenylene group, 2,5,2 ', 5'-tetramethyl-4,4'-biphenylene group, 2,6,2', 6'-tetramethyl-4,4'- Biphenylene group, 3,5,3 ′, 5′-tetramethyl-4,4′-biphenylene group, 2-methoxy-4,4′-biphenylene group, 3-methoxy-4,4′-biphenylene group, 2, 2'-dimethoxy-4,4'-biphenylene group, 3,3'-dimethoxy-4,4'-biphenylene group 2,3′-dimethoxy-4,4′-biphenylene group, 3,5-dimethoxy-4,4′-biphenylene group, 3,6-dimethoxy-4,4′-biphenylene group, 2,5-dimethoxy-4 , 4′-biphenylene group, 2,6-dimethoxy-4,4′-biphenylene group, 2,5,2 ′, 5′-tetramethoxy-4,4′-biphenylene group, 2,6,2 ′, 6 '-Tetramethoxy-4,4'-biphenylene group, 2,2'-ditrifluoromethyl-4,4'-biphenylene group, 2-fluoro-4,4'-biphenylene group, 3-fluoro-4,4' -Biphenylene group, 2,2'-difluoro-4,4'-biphenylene group, 3,3'-difluoro-4,4'-biphenylene group, 2,3'-difluoro-4,4'-biphenylene group, 3 , 5-Difluoro-4,4′-biphenylene group, 3,6-diph Fluoro-4,4′-biphenylene group, 2,5-difluoro-4,4′-biphenylene group, 2,6-difluoro-4,4′-biphenylene group, 2,5,2 ′, 5′-tetrafluoro -4,4'-biphenylene group, 2,6,2 ', 6'-tetrafluoro-4,4'-biphenylene group, 2-cyano-4,4'-biphenylene group, 3-cyano-4,4' -Biphenylene group, 2,2'-dicyano-4,4'-biphenylene group, 3,3'-dicyano-4,4'-biphenylene group, 2,3'-dicyano-4,4'-biphenylene group, 3 , 5-dicyano-4,4′-biphenylene group, 3,6-dicyano-4,4′-biphenylene group, 2,5-dicyano-4,4′-biphenylene group, 2,6-dicyano-4,4 '-Biphenylene group, 2,5,2', 5'-tetracyano-4,4'-biphenylene group 2,6,2 ′, 6′-tetracyano-4,4′-biphenylene group, 2-phenyl-4,4′-biphenylene group, 3-phenyl-4,4′-biphenylene group, 2,2′-diphenyl -4,4'-biphenylene group, 3,3'-diphenyl-4,4'-biphenylene group, 2,3'-diphenyl-4,4'-biphenylene group, 3,5-diphenyl-4,4'- Biphenylene group, 3,6-diphenyl-4,4′-biphenylene group, 2,5-diphenyl-4,4′-biphenylene group, 2,6-diphenyl-4,4′-biphenylene group, 2,5,2 ', 5'-tetraphenyl-4,4'-biphenylene group, 2,6,2', 6'-tetraphenyl-4,4'-biphenylene group, 2-methyl-3,4'-biphenylene group, 4 -Methyl-3,4'-biphenylene group, 5-methyl-3,4'-biphe Len group, 6-methyl-3,4'-biphenylene group, 2'-methyl-3,4'-biphenylene group, 3'-methyl-3,4'-biphenylene group, 2,2'-dimethyl-3, 4'-biphenylene group, 4,2'-dimethyl-3,4'-biphenylene group, 5,2'-dimethyl-3,4'-biphenylene group, 6,2'-dimethyl-3,4'-biphenylene group 2,3′-dimethyl-3,4′-biphenylene group, 4,3′-dimethyl-3,4′-biphenylene group, 5,3′-dimethyl-3,4′-biphenylene group, 6,3 ′ -Dimethyl-3,4'-biphenylene group, 2-methoxy-3,4'-biphenylene group, 4-methoxy-3,4'-biphenylene group, 5-methoxy-3,4'-biphenylene group, 6-methoxy -3,4'-biphenylene group, 2'-methoxy-3,4'-biphenylene group, 3'- Toxi-3,4'-biphenylene group, 2,2'-dimethoxy-3,4'-biphenylene group, 4,2'-dimethoxy-3,4'-biphenylene group, 5,2'-dimethoxy-3,4 '-Biphenylene group, 6,2'-dimethoxy-3,4'-biphenylene group, 2,3'-dimethoxy-3,4'-biphenylene group, 4,3'-dimethoxy-3,4'-biphenylene group, 5,3′-dimethoxy-3,4′-biphenylene group, 6,3′-dimethoxy-3,4′-biphenylene group, 2-fluoro-3,4′-biphenylene group, 4-fluoro-3,4 ′ -Biphenylene group, 5-fluoro-3,4'-biphenylene group, 6-fluoro-3,4'-biphenylene group, 2'-fluoro-3,4'-biphenylene group, 3'-fluoro-3,4 ' -Biphenylene group, 2,2'-difluoro-3,4'-biphenyl Len group, 4,2′-difluoro-3,4′-biphenylene group, 5,2′-difluoro-3,4′-biphenylene group, 6,2′-difluoro-3,4′-biphenylene group, 2, 3'-difluoro-3,4'-biphenylene group, 4,3'-difluoro-3,4'-biphenylene group, 5,3'-difluoro-3,4'-biphenylene group, 6,3'-difluoro- 3,4′-biphenylene group, 2-cyano-3,4′-biphenylene group, 4-cyano-3,4′-biphenylene group, 5-cyano-3,4′-biphenylene group, 6-cyano-3, 4'-biphenylene group, 2'-cyano-3,4'-biphenylene group, 3'-cyano-3,4'-biphenylene group, 2,2'-dicyano-3,4'-biphenylene group, 4,2 '-Dicyano-3,4'-biphenylene group, 5,2'-dicyano-3,4'-biphe Nylene group, 6,2′-dicyano-3,4′-biphenylene group, 2,3′-dicyano-3,4′-biphenylene group, 4,3′-dicyano-3,4′-biphenylene group, 5, 3'-dicyano-3,4'-biphenylene group, 6,3'-dicyano-3,4'-biphenylene group, 2-phenyl-3,4'-biphenylene group, 4-phenyl-3,4'-biphenylene Group, 5-phenyl-3,4'-biphenylene group, 6-phenyl-3,4'-biphenylene group, 2'-phenyl-3,4'-biphenylene group, 3'-phenyl-3,4'-biphenylene Group, 2,2′-diphenyl-3,4′-biphenylene group, 4,2′-diphenyl-3,4′-biphenylene group, 5,2′-diphenyl-3,4′-biphenylene group, 6,2 '-Diphenyl-3,4'-biphenylene group, 2,3'-diphenyl-3, '-Biphenylene group, 4,3'-diphenyl-3,4'-biphenylene group, 5,3'-diphenyl-3,4'-biphenylene group, 6,3'-diphenyl-3,4'-biphenylene group, 2-methyl-3,3′-biphenylene group, 4-methyl-3,3′-biphenylene group, 5-methyl-3,3′-biphenylene group, 6-methyl-3,3′-biphenylene group, 2, 2'-dimethyl-3,3'-biphenylene group, 4,4'-dimethyl-3,3'-biphenylene group, 2,4'-dimethyl-3,3'-biphenylene group, 2,5'-dimethyl- 3,3′-biphenylene group, 2,6-dimethyl-3,3′-biphenylene group, 2,5-dimethyl-3,3′-biphenylene group, 2,4-dimethyl-3,3′-biphenylene group, 2,4,2 ′, 4′-tetramethyl-3,3′-biphenylene group, 2,5 2 ′, 5′-tetramethyl-3,3′-biphenylene group, 2,6,2 ′, 6′-tetramethyl-3,3′-biphenylene group, 2-methoxy-3,3′-biphenylene group, 4-methoxy-3,3′-biphenylene group, 5-methoxy-3,3′-biphenylene group, 6-methoxy-3,3′-biphenylene group, 2,2′-dimethoxy-3,3′-biphenylene group 4,4′-dimethoxy-3,3′-biphenylene group, 2,4′-dimethoxy-3,3′-biphenylene group, 2,5′-dimethoxy-3,3′-biphenylene group, 2,6- Dimethoxy-3,3′-biphenylene group, 2,5-dimethoxy-3,3′-biphenylene group, 2,4-dimethoxy-3,3′-biphenylene group, 2,4,2 ′, 4′-tetramethoxy -3,3'-biphenylene group, 2,5,2 ', 5'-tetramethoxy- 3,3′-biphenylene group, 2,6,2 ′, 6′-tetramethoxy-3,3′-biphenylene group, 2-cyano-3,3′-biphenylene group, 4-cyano-3,3′- Biphenylene group, 5-cyano-3,3′-biphenylene group, 6-cyano-3,3′-biphenylene group, 2,2′-dicyano-3,3′-biphenylene group, 4,4′-dicyano-3 , 3′-biphenylene group, 2,4′-dicyano-3,3′-biphenylene group, 2,5′-dicyano-3,3′-biphenylene group, 2,6-dicyano-3,3′-biphenylene group 2,5-dicyano-3,3′-biphenylene group, 2,4-dicyano-3,3′-biphenylene group, 2,4,2 ′, 4′-tetracyano-3,3′-biphenylene group, 2 , 5,2 ', 5'-tetracyano-3,3'-biphenylene group, 2,6,2', 6'-tetra Ano-3,3′-biphenylene group, 2-fluoro-3,3′-biphenylene group, 4-fluoro-3,3′-biphenylene group, 5-fluoro-3,3′-biphenylene group, 6-fluoro- 3,3′-biphenylene group, 2,2′-difluoro-3,3′-biphenylene group, 4,4′-difluoro-3,3′-biphenylene group, 2,4′-difluoro-3,3′- Biphenylene group, 2,5′-difluoro-3,3′-biphenylene group, 2,6-difluoro-3,3′-biphenylene group, 2,5-difluoro-3,3′-biphenylene group, 2,4- Difluoro-3,3′-biphenylene group, 2,4,2 ′, 4′-tetrafluoro-3,3′-biphenylene group, 2,5,2 ′, 5′-tetrafluoro-3,3′-biphenylene The group 2,6,2 ′, 6′-tetrafluoro-3,3′-biphe Len group, 2-phenyl-3,3′-biphenylene group, 4-phenyl-3,3′-biphenylene group, 5-phenyl-3,3′-biphenylene group, 6-phenyl-3,3′-biphenylene group 2,2′-diphenyl-3,3′-biphenylene group, 4,4′-diphenyl-3,3′-biphenylene group, 2,4′-diphenyl-3,3′-biphenylene group, 2,5 ′ -Diphenyl-3,3'-biphenylene group, 2,6-diphenyl-3,3'-biphenylene group, 2,5-diphenyl-3,3'-biphenylene group, 2,4-diphenyl-3,3'- Biphenylene group, 2,4,2 ′, 4′-tetraphenyl-3,3′-biphenylene group, 2,5,2 ′, 5′-tetraphenyl-3,3′-biphenylene group, 2,6,2 ', 6'-tetraphenyl-3,3'-biphenylene group,
4,4 ″ -p-terphenylene group, 3,4 ″ -p-terphenylene group, 2,4 ″ -p-terphenylene group, 3,3 ″ -p-terphenylene group, 2, 3 "-p-terphenylene group, 2,2" -p-terphenylene group, 4,4 "-m-terphenylene group, 3,4" -m-terphenylene group, 2,4 ''-P-terphenylene group, 3,3''-m-terphenylene group, 2,3''-m-terphenylene group, 2,2''-m-terphenylene group, 4,4''- o-terphenylene group, 3,4 "-o-terphenylene group, 2,4" -o-terphenylene group, 3,3 "-o-terphenylene group, 2,3" -o- Terphenylene group, 2,2 ″ -o-terphenylene group, 1,4-naphthylene group, 1,5-naphthylene group, 2,6-naphthylene group, 2,7-naphthylene group, 1-phenylnaphthal group Talen-diyl group, 2-phenylnaphthalene-diyl group, 9,9-dimethylfluorene-2,7-diyl group, 9,9-dioctylfluorene-2,7-diyl group, 9,9-diphenylfluorene-2, 7-diyl group, 9,9′-spirobifluorene-2,7-diyl group, 11,11′-dimethylbenzo [a] fluorene-3,9-diyl group, 11,11′-dimethylbenzo [a] Fluorene-2,9-diyl group, 11,11′-dimethylbenzo [b] fluorene-3,9-diyl group, 11,11′-dimethylbenzo [c] fluorene-2,9-diyl group, fluoranthene-3 , 8-diyl group, pyrene-1,6-diyl group, pyrene-2,3-diyl group, pyrene-2,7-diyl group, pyrene-1,8-diyl group, anthracene-2,6-diyl group ,Ann Tracene-1,5-diyl group, anthracene-9,10-diyl group, triphenylene-2,7-diyl group, chrysene-2,8-diyl group, pyrrole-2,5-diyl group, 1-methylpyrrole- 2,5-diyl group, 1-phenylpyrrole-2,5-diyl group, thiophene-2,5-diyl group, 3-hexylthiophene-2,5-diyl group, 3,4-ethylenedioxythiophene-2 , 5-diyl group, thiophene-3,4-diyl group, furan-2,5-diyl group, furan-3,4-diyl group, thiazole-diyl group, isothiazole-diyl group, oxazole-diyl group, iso Oxazole-diyl group, pyridine-2,5-diyl group, pyridine-2,6-diyl group, pyrazine-2,5-diyl group, triazine-2,4-diyl group, benzothiophene -Diyl group, benzofuran-diyl group, benzothiazole-diyl group, benzoisothiazole-diyl group, 2,1,3-benzothiadiazole-diyl group, benzoxazole-diyl group, benzoisoxazole-diyl group, 2,1 , 3-Benzoxadiazol-diyl group, thieno [3,2-b] thiophene-2,5-diyl group, thieno [3,2-b] thiophene-3,6-diyl group, dithieno [3,2 -B: 2 ', 3'-c] thiophene-2,6-diyl group, benzodithiophene-diyl group, dibenzothiophene-2,8-diyl group, 9-methylcarbazole-2,7-diyl group, 9 -Phenylcarbazole-2,7-diyl group, 9-biphenylcarbazole-2,7-diyl group, 9-naphthylcarbazole-2,7-diyl group, Tylcarbazole-3,6-diyl group, 9-phenylcarbazole-3,6-diyl group, 9-biphenylcarbazole-3,6-diyl group, 9-naphthylcarbazole-3,6-diyl group, benzothienobenzothiophene -2,7-diyl group, dibenzofuran-2,8-diyl group, 10-methylphenoxazine-3,7-diyl group, 10-phenylphenoxazine-3,7-diyl group, 10-methylphenothiazine-3, 7-diyl group, 10-phenylphenothiazine-3,7-diyl group, thianthrene-1,9-diyl group, thianthrene-2,7-diyl group, 2-phenylthiophene-diyl group, 2,5-diphenylthiophene- Diyl group, 2-phenylfuran-diyl group, 2,5-diphenylfuran-diyl group, 2,2'-bithiophene- Examples include 5,5′-diyl group, 2,2′-bithiophene-3,3′-diyl group, terthiophene-5,5 ″ -diyl group, and the like. Absent.

  X is a phenylene group, biphenylene group, terphenylene group, naphthylene group, or fluorene-diyl group (these groups are each independently a methyl group, an ethyl group, 3-18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C 1-3 halogenated alkyl group, carbon A halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, And may have one or more substituents selected from the group consisting of a C18-40 triarylsilyl group, a cyano group, a halogen atom, and a deuterium atom. 1,4-phenylene group, 1,3-phenylene group, 4,4′-biphenylene group, 3,3′-biphenylene group, 3,4′-biphenylene group, 4,4 ″ -p-terphenylene group Group, 4,4 ″ -m-terphenylene group, 2,6-naphthylene group, or fluorene-2,7-diyl group (these groups are each independently a methyl group, an ethyl group, a carbon number of 3 -18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C1-C3 halogenated alkyl group, carbon number 1 to 3 halogenated alkoxy groups, 6 to 12 aryl groups, 6 to 18 aryloxy groups, 3 to 20 heteroaryl groups, 3 to 18 trialkylsilyl groups, carbon Number 18-40 bird More preferably, it may have one or more substituents selected from the group consisting of a reel silyl group, a cyano group, a halogen atom, and a deuterium atom), 1,4-phenylene group, 1,3- More preferred is a phenylene group or a 4,4′-biphenylene group.

In the 4-aminocarbazole compound represented by the general formula (1), R ^{1 to} R ⁷ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms. Groups (these groups are each independently a methyl group, an ethyl group, a straight chain of 3 to 18 carbon atoms, a branched or cyclic alkyl group, a methoxy group, an ethoxy group, a straight chain of 3 to 18 carbon atoms, It consists of a branched or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen atom, and a deuterium atom. May have one or more substituents selected from the group), methyl group, ethyl group, linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group, ethoxy group, and carbon number 3 ~ 18 straight, branched, or young Is a cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a trialkylsilyl group having 3 to 18 carbon atoms, a triarylsilyl group having 18 to 40 carbon atoms, cyano Represents a group, a halogen atom, a deuterium atom, or a hydrogen atom.

The aromatic hydrocarbon group having 6 to 20 carbon atoms in R ¹ to R ^7, is not particularly limited, and an aromatic hydrocarbon group having 6 to 20 carbon atoms shown in ^Ar 1 to Ar ³ of the The same substituents can be mentioned.

The hetero aromatic group having 3 to 20 carbon atoms in R ¹ to R ^7, is not particularly limited, for example, thienyl group, furyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, a benzothienyl group , Benzofuranyl group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzoisoxazolyl group, 2,1,3-benzooxadiazolyl group, Examples thereof include a dibenzothienyl group, a dibenzofuranyl group, a phenoxazinyl group, a phenothiazinyl group, and a thiantenyl group.

Linear 3 to 18 carbon atoms in R ¹ to R ^7, branch, or as a cyclic alkyl group is not particularly limited, straight of 3 to 18 carbon atoms shown in ^Ar 1 to Ar ³ of the Examples include the same substituent as the chain, branched, or cyclic alkyl group.

Linear 3 to 18 carbon atoms in R ¹ to R ^7, branch, or as a cyclic alkoxy group is not particularly limited, straight of 3 to 18 carbon atoms shown in ^Ar 1 to Ar ³ of the Examples include the same substituent as the chain, branched, or cyclic alkyl group.

Examples of the halogenated alkyl group having 1 to 3 carbon atoms in R ¹ to R ^7, is not particularly limited, the same substituents as the alkyl halide group having 1 to 3 carbon atoms shown in ^Ar 1 to Ar ³ of the Groups.

Examples of the aryloxy group having 6 to 18 carbon atoms in R ¹ to R ^7, is not particularly limited, the same substituents as aryloxy group having 6 to 18 carbon atoms shown in ^Ar 1 to Ar ³ of the Can be mentioned.

The trialkylsilyl group having 3 to 18 carbon atoms in R ¹ to R ^7, is not particularly limited, the same substituents as trialkylsilyl group having a carbon number of 3 to 18 shown in ^Ar 1 to Ar ³ of the Groups.

The triarylsilyl group having 18 to 40 carbon atoms in R ^{1 to} R ⁷ is not particularly limited, but is the same substitution as the triarylsilyl group having 18 to 40 carbon atoms shown in Ar ^{1 to} Ar ³ . Groups.

Although it does not specifically limit as a halogen atom, The same substituent as the halogen atom shown in said Ar < ¹ > -Ar < ³ > is mentioned.

Below, the substituent which may be substituted by the C6-C20 aromatic hydrocarbon group or C3-C20 heteroaromatic group in R < ¹ > -R < ⁷ > (these groups are each independently , Methyl group, ethyl group, linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group, ethoxy group, linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, carbon number 1 -3 halogenated alkyl groups, C6-C20 aryl groups, C3-C20 heteroaryl groups, cyano groups, halogen atoms, and substituents selected from the group consisting of deuterium atoms) will be described.

Although it does not specifically limit as a C3-C18 linear, branched, or cyclic alkyl group, The C3-C18 linear, branched, or cyclic shown in said Ar < ¹ > -Ar < ³ >. And the same substituent as the alkyl group of.

Linear 3 to 18 carbon atoms, branched, or as a cyclic alkoxy group is not particularly limited, a straight-chain carbon atoms 3 to 18 shown in ^Ar 1 to Ar ³ of the, branched or cyclic And the same substituents as the alkoxy group.

Examples of the halogenated alkyl group having 1 to 3 carbon atoms is not particularly limited, the same substituent group as a halogenated alkyl group having 1 to 3 carbon atoms shown in Ar ¹ to Ar ³ of the.

Examples of the aryl group having 6 to 20 carbon atoms is not particularly limited, the same substituent group as the aryl group having 6 to 20 carbon atoms shown in ^Ar 1 to Ar ³ of the.

The heteroaryl group having 3 to 20 carbon atoms is not particularly limited, the same substituent groups as heteroaryl group having 3 to 20 carbon atoms shown in Ar ¹ to Ar ³ of the.

Although it does not specifically limit as a halogen atom, The same substituent as the halogen atom shown in said Ar < ¹ > -Ar < ³ > is mentioned.

R ^{1 to} R ⁷ , a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a fluorenyl group (these groups are each independently a methyl group, an ethyl group, a carbon, A linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, (It may have one or more substituents selected from the group consisting of aryl groups having 6 to 20 carbon atoms, cyano groups, halogen atoms, and deuterium atoms) methyl groups, ethyl groups, 3 to 18 carbon atoms Linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, aryloxy group having 6 to 18 carbon atoms, cyano group, deuterium An atom or a hydrogen atom is preferable, and a phenyl group, a naphthyl group, or a biphenyl group (these groups are each independently a methyl group, an ethyl group, a straight-chain, branched, or cyclic group having 3 to 18 carbon atoms) Having at least one substituent selected from the group consisting of an alkyl group, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a cyano group, and a deuterium atom. Methyl group, ethyl group, C3-C18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, phenoxy It is more preferably a group, a cyano group, a deuterium atom, or a hydrogen atom, and further preferably a phenyl group, a methyl group, a methoxy group, a cyano group, a deuterium atom, or a hydrogen atom.

  Although the preferable compound is illustrated below about the 4-aminocarbazole compound represented by General formula (1), it is not limited to these compounds.

  The 4-aminocarbazole compound represented by the general formula (1) is obtained by, for example, aminating a halogenated carbazole intermediate by a known method (Tetrahedron Letters, 1998, Vol. 39, page 2367). Can be synthesized. Specifically, it can be synthesized according to the following scheme 1.

  A 9H-carbazole compound halogenated at the 4-position represented by the general formula (2) and a compound having a halogen atom represented by the general formula (3) are treated with a copper catalyst or a palladium catalyst in the presence of a base. And a 4-halogenated-9-substituted carbazole compound represented by the general formula (4) is obtained. The obtained 4-halogenated-9-substituted carbazole compound represented by the general formula (4) and the secondary amine compound represented by the general formula (5) are used in the presence of a base using a copper catalyst or a palladium catalyst. By reacting with each other, a 4-aminocarbazole compound represented by the general formula (1) can be obtained.

  Moreover, the 4-halogenated-9-substituted carbazole compound represented by the general formula (4) is obtained using a copper catalyst or a palladium catalyst in the presence of a primary amine compound represented by the general formula (6) and a base. By making it react, it can be induced to a secondary amine compound represented by the general formula (7). By reacting the obtained secondary amine compound represented by the general formula (7) and the compound having a halogen atom represented by the general formula (8) using a copper catalyst or a palladium catalyst in the presence of a base. A 4-aminocarbazole compound represented by the general formula (1) can be obtained.

(In the formula, Ar ^{1 to} Ar ⁵ , X and R ^{1 to} R ⁷ are as defined above, and Y ^{1 to} Y ³ each independently represent a halogen atom [iodine, bromine, chlorine, or fluorine].)
The method for synthesizing the 4-aminocarbazole compound represented by the general formula (1) is not limited to Scheme 1, and it can be synthesized by other routes.

  The 4-aminocarbazole compound represented by the general formula (1) of the present invention can be used as a light emitting layer, a hole transport layer or a hole injection layer of an organic EL device.

  In particular, the 4-aminocarbazole compound represented by the general formula (1) is any of a hole injection layer, a hole transport layer, and a light emitting layer in an element using a fluorescent light emitting material or a phosphorescent light emitting material for a light emitting layer. It can be preferably used in one or more layers.

  In the light-emitting layer when the 4-aminocarbazole compound represented by the general formula (1) is used as a hole injection layer and / or a hole transport layer of an organic EL device, a known fluorescence that has been conventionally used is used. Alternatively, a phosphorescent material can be used. The light emitting layer may be formed of only one kind of light emitting material, or one or more kinds of light emitting materials may be doped in the host material.

  Further, a substrate, an anode, a hole injection layer, and a hole transport when the 4-aminocarbazole compound represented by the general formula (1) is used as a hole injection layer and / or a hole transport layer of an organic EL element. As the layer, the electron transport layer, the electron injection layer, the cathode and the like, conventionally known materials can be used.

  When forming the hole injection layer and / or hole transport layer composed of the 4-aminocarbazole compound represented by the general formula (1), two or more kinds of materials are contained or laminated as necessary. For example, oxides such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane In addition, a known electron-accepting material such as hexacyanohexaazatriphenylene may be contained or laminated.

  Moreover, the 4-aminocarbazole compound represented by the general formula (1) of the present invention can also be used as a light emitting layer of an organic EL device. When the 4-aminocarbazole compound represented by the general formula (1) is used as a light emitting layer of an organic EL device, the 4-aminocarbazole compound is used alone, used by doping a known light emitting host material, Alternatively, it can be used by doping a known light-emitting dopant.

  Examples of a method for forming a hole injection layer, a hole transport layer, or a light emitting layer containing the 4-aminocarbazole compound represented by the general formula (1) include a vacuum deposition method, a spin coating method, and a casting method. The known methods can be applied.

  EXAMPLES Hereinafter, although this invention is demonstrated further in detail based on an Example, this invention is not limited by these Examples.

  FDMS measurement was performed using M-80B manufactured by Hitachi, Ltd.

  The triplet level was evaluated using an F2500 spectrofluorometer manufactured by Hitachi High-Technologies Corporation.

  The ionization potential was evaluated by cyclic voltammetry using HA-501 and HB-104 manufactured by Hokuto Denko.

  The UV / Vis spectrum was measured using U-2010 manufactured by Hitachi, Ltd.

  The light emission characteristics of the organic EL element were evaluated by applying a direct current to the element produced using a source meter (2400) manufactured by Keithley Instruments and using a luminance meter of LUMINANCEMETER (BM-9) manufactured by TOPCON.

Synthesis Example 1 (Synthesis of 2-nitro-6-chlorobiphenyl [formula (9)])
Under a nitrogen stream, in a 1 L three-necked flask, 75.0 g (390.6 mmol) of 2,3-dichloronitrobenzene, 47.6 g (390.6 mmol) of phenylboronic acid, 9.0 g of tetrakis (triphenylphosphine) palladium (7. 8 mmol), 250 mL of tetrahydrofuran, 518 g of 40 wt% tripotassium phosphate aqueous solution (976.5 mmol as tripotassium phosphate) were added, and the mixture was heated to reflux for 8 hours. After cooling to room temperature, the aqueous layer and the organic layer were separated, the organic layer was washed with a saturated aqueous ammonium chloride solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was recrystallized from ethanol to isolate 62.8 g of 2-nitro-6-chlorobiphenyl as pale yellow needles (yield 68%).

The compound was identified by ¹ H-NMR measurement and ¹³ C-NMR measurement.

¹ H-NMR (CDCl ₃ ); 7.66-7.74 (m, 2H), 7.41-7.45 (m, 4H), 7.22-7.27 (m, 2H)
¹³ C-NMR (CDCl ₃ ); 135.71, 134.68, 133.91, 133.29, 128.91, 128.71, 128.68, 128.55, 128.46, 121.96
Synthesis Example 2 (Synthesis of 4-chlorocarbazole [Formula (10)])
In a 500 mL eggplant-shaped flask under a nitrogen stream, 50.0 g (214.5 mmol) of 2-nitro-6-chlorobiphenyl obtained in Synthesis Example 1, 140.5 g (536.2 mmol) of triphenylphosphine, o-dichlorobenzene 200 mL was charged and stirred at 150 ° C. for 18 hours. O-Dichlorobenzene was distilled off under reduced pressure, and toluene was added to the residue, followed by purification by silica gel column chromatography (toluene) to isolate 36.6 g (182.3 mmol) of 4-chlorocarbazole white powder. (Yield 85%).

The compound was identified by ¹ H-NMR measurement and ¹³ C-NMR measurement.

¹ H-NMR (acetone-d6); 10.71 (br-s, 1H), 8.52 (d, 1H), 7.15-7.59 (m, 6H)
¹³ C-NMR (Acetone-d6); 141.80, 140.71, 128.37, 126.76, 126.61, 122.99, 122.33, 120.57, 119.88, 119.75, 111.45,110.15
Synthesis Example 3 (Synthesis of 4-chloro-9-phenylcarbazole)
In a 200 mL three-necked flask under a nitrogen stream, 17.0 g (84.3 mmol) of 4-chlorocarbazole obtained in Synthesis Example 2, 15.8 g (101.1 mmol) of bromobenzene, and 19.5 g (141.6 mmol) of potassium carbonate. ), 85 mL of o-xylene, 227 mg (1.0 mmol) of palladium acetate, and 714 mg (3.5 mmol) of tri (tert-butyl) phosphine were added and stirred at 130 ° C. for 24 hours. After cooling to room temperature, 60 mL of pure water was added and the organic layer was separated. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane), and 14.3 g (51.6 mmol) of colorless oily 4-chloro-9-phenylcarbazole was isolated (yield 61%).

The compound was identified by ¹ H-NMR measurement and ¹³ C-NMR measurement.

¹ H-NMR (CDCl ₃ ); 8.67 (d, 1H), 7.23-7.65 (m, 11H)
¹³ C-NMR (CDCl ₃ ); 142.04, 141.05, 137.15, 129.94, 128.73, 127.93, 127.39, 126.41, 126.06, 123.07, 122 21, 120.64, 120.51, 120.23, 109.56, 108.11
Synthesis Example 4 (Synthesis of 4-chloro-9- (2-dibenzothienyl) carbazole)
In a 50 mL three-necked flask under a nitrogen stream, 2.6 g (12.9 mmol) of 4-chlorocarbazole obtained in Synthesis Example 2, 3.4 g (12.9 mmol) of 2-bromodibenzothiophene, 3.5 g of potassium carbonate (25 0.9 mmol), o-xylene 13 mL, palladium acetate 29 mg (0.12 mmol), tri (tert-butyl) phosphine 91 mg (0.45 mmol) were added, and the mixture was stirred at 140 ° C. for 18 hours. After cooling to room temperature, 10 mL of pure water was added, and the organic layer was separated. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of toluene and hexane (volume ratio = 1: 2)), and 3.5 g (9 of brown glassy solid of 4-chloro-9- (2-dibenzothienyl) carbazole was obtained. 0.1 mmol) isolated (yield 70%).

The compound was identified by ¹ H-NMR measurement.

¹ H-NMR (CDCl ₃ ); 8.71 (d, 1H), 8.27 (d, 1H), 8.04-8.16 (m, 3H), 7.83-7.94 (m, 2H), 7.25-7.61 (m, 7H)
Synthesis Example 5 (Synthesis of 4-chloro-9- (4-biphenyl) carbazole)
Under a nitrogen stream, 10.0 g (49.5 mmol) of 4-chlorocarbazole obtained in Synthesis Example 2 in a 200 mL three-necked flask, 11.6 g (52.0 mmol) of 4-bromobiphenyl, 9.5 g of potassium carbonate (69. 4 mmol), 100 mL of o-xylene, 111 mg (0.49 mmol) of palladium acetate, and 349 mg (1.73 mmol) of tri (tert-butyl) phosphine were added and stirred at 130 ° C. for 14 hours. After cooling to room temperature, 50 mL of pure water was added, and the organic layer was separated. The organic layer was washed with pure water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained powder was washed with ethanol, and 12.5 g (35.4 mmol) of a light brown powder of 4-chloro-9- (4-biphenylyl) carbazole was isolated (yield 71%).

The compound was identified by ¹ H-NMR measurement and ¹³ C-NMR measurement.

¹ H-NMR (CDCl ₃ ); 8.68 (d, 1H), 7.80 (d, 2H), 7.67 (d, 2H), 7.22-7.59 (m, 11H)
¹³ C-NMR (CDCl ₃ ); 142.04, 141.05, 140.83, 140.08, 136.29, 128.97, 128.79, 128.58, 127.74, 127.61, 127 .14, 126.48, 126.13, 123.13, 122.32, 120.75, 120.62, 120.33, 109.65, 108.20
Synthesis Example 6 (Synthesis of 4-chloro-9- [4- (2-pyridyl) phenyl] carbazole)
Under a nitrogen stream, 5.0 g (24.7 mmol) of 4-chlorocarbazole obtained in Synthesis Example 2 in a 100 mL three-necked flask, 6.0 g (26.0 mmol) of 4- (2-pyridyl) bromobenzene, potassium carbonate 4 0.7 g (34.7 mmol), o-xylene 25 mL, palladium acetate 55 mg (0.24 mmol), tri (tert-butyl) phosphine 174 mg (0.86 mmol) were added, and the mixture was stirred at 140 ° C. for 14 hours. After cooling to room temperature, 20 mL of pure water was added, and the organic layer was separated. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 2: 1)) to obtain 4-chloro-9- [4- (2-pyridyl) phenyl] carbazole as a brown glassy solid. 0.5 g (12.7 mmol) was isolated (51% yield).

The compound was identified by ¹ H-NMR measurement and ¹³ C-NMR measurement.

¹ H-NMR (CDCl ₃ ); 8.66-8.75 (m, 2H) 8.20 (d, 2H), 7.77 (d, 2H), 7.61 (d, 2H), 7. 22-7.46 (m, 7H)
¹³ C-NMR (CDCl ₃ ); 156.33, 149.84, 141.92, 140.93, 138.93, 137.76, 136.92, 128.79, 128.49, 127.50, 126 53, 126.19, 123.15, 122.50, 122.39, 120.86, 120.69, 120.56, 120.42, 109.65, 108.20.
Synthesis Example 7 (Synthesis of 4-chloro-9- (3-quinolyl) carbazole)
Under a nitrogen stream, 5.0 g (24.7 mmol) of 4-chlorocarbazole obtained in Synthesis Example 2 in a 100 mL three-necked flask, 5.1 g (24.7 mmol) of 3-bromoquinoline, 4.7 g of potassium carbonate (34. 7 mmol), 25 mL of o-xylene, 276 mg (1.23 mmol) of palladium acetate and 869 mg (4.3 mmol) of tri (tert-butyl) phosphine were added and stirred at 140 ° C. for 24 hours. After cooling to room temperature, 20 mL of pure water was added, and the organic layer was separated. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 3: 1)), and 4.6 g (14. 14) of 4-chloro-9- (3-quinolyl) carbazole as a brown glassy solid. 0 mmol) isolated (56% yield).

The compound was identified by ¹ H-NMR measurement and ¹³ C-NMR measurement.

¹ H-NMR (CDCl ₃ ); 9.09 (s, 1H), 8.70 (d, 1H), 8.31 (s, 1H), 8.26 (d, 1H), 7.90 (d , 1H), 7.82 (d, 1H), 7.66 (t, 1H), 7.22-7.51 (m, 6H)
¹³ C-NMR (CDCl ₃ ); 183.45, 149.59, 147.23, 142.06, 141.07, 133.38, 130.84, 130.27, 129.59, 129.02, 128 .18, 127.78, 126.83, 126.48, 123.35, 122.61, 121.41, 120.95, 109.16, 107.73
Example 1 (Synthesis of Compound (A8))
In a 50 mL three-necked flask under a nitrogen stream, 1.6 g (5.8 mmol) of 4-chloro-9-phenylcarbazole obtained in Synthesis Example 3 and N-biphenyl-N ′, N′-bisbiphenyl-1,4 were obtained. -Phenylenediamine 3.0 g (5.3 mmol), sodium-tert-butoxide 0.74 g (7.4 mmol), o-xylene 15 mL, palladium acetate 12 mg (0.05 mmol), tri (tert-butyl) phosphine 37 mg (0 .18 mmol) was added and stirred at 140 ° C. for 10 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with pure water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 3: 5)), and 3.4 g (4.2 mmol) of a pale yellow glassy solid of compound (A8) was isolated (yield). 79%).

  The compound was identified by FDMS.

FDMS: 805
Example 2 (Synthesis of Compound (A33))
In a 50 mL three-necked flask under a nitrogen stream, 2.7 g (7.0 mmol) of 4-chloro-9- (2-dibenzothienyl) carbazole obtained in Synthesis Example 4 and N-phenyl-N ′, N′-bis. Biphenyl-1,4-phenylenediamine 3.4 g (7.0 mmol), sodium-tert-butoxide 0.94 g (9.8 mmol), o-xylene 15 mL, palladium acetate 47 mg (0.21 mmol), tri (tert-butyl) ) 148 mg (1.4 mmol) of phosphine was added and stirred at 140 ° C. for 12 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with pure water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1: 1)), and 4.7 g (5.7 mmol) of a pale yellow glassy solid of compound (A33) was isolated (recovery). 82%).

  The compound was identified by FDMS.

FDMS: 835
Example 3 (Synthesis of Compound (A37))
In a 50 mL three-necked flask under a nitrogen stream, 1.5 g (3.9 mmol) of 4-chloro-9- (2-dibenzothienyl) carbazole obtained in Synthesis Example 4 and N, N′-diphenyl-N ′-( 4- (4-Dibenzothienyl) phenyl) -1,4-phenylenediamine 2.0 g (3.9 mmol), sodium tert-butoxide 0.52 g (5.4 mmol), o-xylene 15 mL, palladium acetate 26 mg (0 .11 mmol) and 77 mg (0.38 mmol) of tri (tert-butyl) phosphine were added and stirred at 140 ° C. for 10 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with pure water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1: 1)), and 2.4 g (2.8 mmol) of a pale yellow glassy solid of compound (A37) was isolated (recovery). 72%).

  The compound was identified by FDMS.

FDMS: 865
Example 4 (Synthesis of Compound (A62))
In a 50 mL three-necked flask under a nitrogen stream, 2.0 g (5.6 mmol) of 4-chloro-9- (4-biphenyl) carbazole obtained in Synthesis Example 5 and N, N′-diphenyl-N ′-(2 -Dibenzothienyl) -1,3-phenylenediamine 2.4 g (5.6 mmol), sodium-tert-butoxide 0.75 g (7.8 mmol), o-xylene 15 mL, palladium acetate 12 mg (0.05 mmol), tri ( Tert-butyl) phosphine (35 mg, 0.17 mmol) was added, and the mixture was stirred at 140 ° C. for 6 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with pure water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1: 1)), and 3.6 g (4.8 mmol) of a colorless glassy solid of compound (A62) was isolated (yield) 87%).

  The compound was identified by FDMS.

FDMS: 759
Example 5 (Synthesis of Compound (A86))
In a 50 mL three-necked flask under a nitrogen stream, 1.0 g (2.8 mmol) of 4-chloro-9- [4- (2-pyridyl) phenyl] carbazole obtained in Synthesis Example 6 and N, N′-diphenyl- N ′-(p-terphenyl) -1,3-phenylenediamine 1.3 g (2.8 mmol), sodium tert-butoxide 0.37 g (3.9 mmol), o-xylene 10 mL, palladium acetate 6 mg (0. 03 mmol) and 21 mg (0.10 mmol) of tri (tert-butyl) phosphine were added and stirred at 140 ° C. for 8 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with pure water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of toluene and hexane (volume ratio = 1: 1)), and 1.7 g (2.2 mmol) of a pale yellow glassy solid of the compound (A86) was isolated (yield). 79%).

  The compound was identified by FDMS.

FDMS: 806
Example 6 (Synthesis of Compound (A87))
In a 50 mL three-necked flask under a nitrogen stream, 1.2 g (3.6 mmol) of 4-chloro-9- (3-quinolyl) carbazole obtained in Synthesis Example 7 and N- (p-tolyl) -N ′, N '-Bisbiphenyl-1,3-phenylenediamine (1.8 g, 3.6 mmol), sodium-tert-butoxide (0.48 g, 5.0 mmol), o-xylene (15 mL), palladium acetate (8 mg, 0.04 mmol), tri ( 24 mg (0.12 mmol) of tert-butyl) phosphine was added and stirred at 140 ° C. for 12 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with pure water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1: 1)), and 2.3 g (3.0 mmol) of a light brown glassy solid of compound (A87) was isolated (recovery). 86%).

  The compound was identified by FDMS.

FDMS: 794
Example 7 (Synthesis of Compound (A104))
In a 50 mL three-necked flask under a nitrogen stream, 2.0 g (7.2 mmol) of 4-chloro-9-phenylcarbazole obtained in Synthesis Example 3 and 2.9 g of N-phenyl-N ′, N′-diphenylbenzidine ( 7.2 mmol), 0.96 g (10.0 mmol) of sodium-tert-butoxide, 20 mL of o-xylene, 16 mg (0.07 mmol) of palladium acetate, and 70 mg (0.35 mmol) of tri (tert-butyl) phosphine The mixture was stirred at 140 ° C. for 10 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with pure water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1: 1)), and 3.6 g (5.5 mmol) of a pale yellow glassy solid of compound (A104) was isolated (recovery). Rate 77%).

  The compound was identified by FDMS.

FDMS: 653
Example 8 (Synthesis of Compound (A106))
In a 50 mL three-necked flask under a nitrogen stream, 1.5 g (5.4 mmol) of 4-chloro-9-phenylcarbazole obtained in Synthesis Example 3 and 3.0 g of N-phenyl-N ′, N′-bisbiphenylbenzidine. (5.4 mmol), 0.72 g (7.5 mmol) of sodium-tert-butoxide, 20 mL of o-xylene, 12 mg (0.05 mmol) of palladium acetate, and 35 mg (0.17 mmol) of tri (tert-butyl) phosphine were added. And stirred at 140 ° C. for 6 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The aqueous layer and the organic layer were separated, and the organic layer was washed with pure water and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixed solvent of toluene and hexane (volume ratio = 1: 1)), and 3.4 g (4.3 mmol) of a pale yellow glassy solid of compound (A106) was isolated (recovery). Rate 81%).

  The compound was identified by FDMS.

  FDMS: 805

Example 9 (Evaluation of ionization potential and energy gap of compound (A104))
The ionization potential was measured by cyclic voltammetry. Compound (A104) is dissolved in an anhydrous dichloromethane solution having a concentration of tetrabutylammonium perchlorate of 0.1 mol / L at a concentration of 0.001 mol / L. The working electrode is glassy carbon, the counter electrode is platinum wire, and the reference electrode is It was measured using a silver wire immersed in acetonitrile AgNO _3. Table 1 shows the ionization potential of the compound (A104) when ferrocene is used as a standard substance and the oxidation-reduction potential of ferrocene is used as a reference.

The energy gap was estimated from the wavelength of the absorption edge of the UV / Vis spectrum. Compound (A104) was dissolved in tetrahydrofuran at a concentration of 1 × 10 ⁻⁵ mol / L, and a UV / Vis spectrum was measured. Table 1 shows the energy gap estimated from the wavelength of the absorption edge.

Comparative Example 1 (Evaluation of ionization potential and energy gap of compound (a))
In the same manner as in Example 9, the ionization potential and energy gap of the compound (a) in which an amino group was bonded to the 3-position of the carbazole ring were evaluated. The results are shown in Table 1.

Comparative Example 2 (Evaluation of ionization potential and energy gap of compound (b))
In the same manner as in Example 9, the ionization potential and energy gap of the compound (b) in which an amino group was bonded to the 2-position of the carbazole ring were evaluated. The results are shown in Table 1.

Comparative Example 3 (Evaluation of ionization potential and energy gap of NPD)
NPD ionization potential and energy gap were evaluated in the same manner as in Example 9. The results are shown in Table 1.

  The 4-aminocarbazole compound of the present invention has an ionization potential equivalent to that of NPD and 2-aminocarbazole compound (compound (b)), and NPD, 3-aminocarbazole compound (compound (a)) and 2-aminocarbazole. Compared with the compound (compound (b)), the energy gap is large, which solves the problems of conventionally known compounds.

Example 10 (Device evaluation of compound (A8))
The glass substrate on which the ITO transparent electrode (anode) having a thickness of 200 nm was laminated was subjected to ultrasonic cleaning with acetone and pure water and boiling cleaning with isopropyl alcohol. Further, ultraviolet ozone cleaning was performed, and after evacuation with a vacuum pump until the pressure became 5 × 10 ⁻⁴ Pa or less after installation in a vacuum deposition apparatus. First, copper phthalocyanine was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / second to form a 10 nm hole injection layer. Thereafter, the compound (A8) was deposited to 40 nm at a deposition rate of 0.3 nm / second to form a hole transport layer. Subsequently, DPAVBi (4,4′-bis [2- (4-diphenylaminophenyl) vinyl] biphenyl) which is a blue light emitting dopant material and ADN (9,10-di (2-naphthyl) anthracene) which is a host material Was vapor-deposited at a vapor deposition rate of 0.33 nm / second so that the weight ratio was 1: 32.3 to obtain a 40 nm light-emitting layer. Next, Alq ₃ (tris (8-quinolinolato) aluminum) was vapor-deposited at 0.3 nm / second to form a 20 nm electron transport layer. Subsequently, lithium fluoride was deposited as an electron injection layer to a thickness of 0.5 nm at a deposition rate of 0.01 nm / second, and aluminum was further deposited to a thickness of 100 nm at a deposition rate of 0.25 nm / second to form a cathode. In a nitrogen atmosphere, a sealing glass plate was bonded with a UV curable resin to obtain an organic EL element for evaluation. A current of 20 mA / cm ² was applied to the device thus fabricated, and driving voltage and current efficiency were measured. The results are shown in Table 2.

Example 11 (Element evaluation of compound (A33))
An organic EL device was produced in the same manner as in Example 10 except that the compound (A8) was changed to (A33). Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

Example 12 (Element evaluation of compound (A37))
An organic EL device was produced in the same manner as in Example 10 except that the compound (A8) was changed to (A37). Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

Example 13 (Element evaluation of compound (A62))
An organic EL device was produced in the same manner as in Example 10 except that the compound (A8) was changed to (A62). Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

Example 14 (Device evaluation of compound (A86))
An organic EL device was produced in the same manner as in Example 10 except that the compound (A8) was changed to (A86). Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

Example 15 (Element Evaluation of Compound (A87))
An organic EL device was produced in the same manner as in Example 10 except that the compound (A8) was changed to (A87). Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

Example 16 (Element evaluation of compound (A104))
An organic EL device was produced in the same manner as in Example 10 except that the compound (A8) was changed to (A104). Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

Example 17 (Element evaluation of compound (A106))
An organic EL device was produced in the same manner as in Example 10 except that the compound (A8) was changed to (A106). Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

Comparative Example 4
An organic EL device was produced in the same manner as in Example 10 except that the compound (A8) was changed to NPD. Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

  The 4-aminocarbazole compound of the present invention showed higher current efficiency (luminous efficiency) than NPD, and the drive voltage of the organic EL device could be kept low.

Claims (7)

General formula (1)

(In the formula, Ar ^{1 to} Ar ³ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom or sulfur atom). [These groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear or branched chain having 3 to 18 carbon atoms. Or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, phenyl group, biphenyl group, naphthyl group, phenanthryl group , carbazolyl group, 9-phenylcarbazolyl It represents group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, a halogen atom, and a substituent may have one or more members selected from the group consisting of a deuterium atom.
Ar ⁴ is an aromatic hydrocarbon group having 6 to 17 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom, nitrogen atom, or sulfur atom. A methyl group, an ethyl group, a C3-C18 linear, branched or cyclic alkyl group, a methoxy group, an ethoxy group, a C3-C18 linear, branched or cyclic alkoxy group, a carbon number 1 to 3 halogenated alkyl groups, 1 to 3 carbon atoms halogenated alkoxy groups, phenyl groups, biphenyl groups, naphthyl groups , carbazolyl groups, 9-phenylcarbazolyl groups, dibenzothienyl groups, dibenzofuranyl groups, It may have one or more substituents selected from the group consisting of an ano group, a halogen atom, and a deuterium atom.
X is a bivalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, 18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C1-C3 halogenated alkyl group, carbon number 1 ~ 3 halogenated alkoxy group, a phenyl group, consisting of a biphenyl group, a naphthyl group, carbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, halogen atom, and deuterium atoms It may have one or more substituents selected from the group].
R ^{1 to} R ⁷ are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms. , a methoxy group, an ethoxy group, a straight chain 3 to 18 carbon atoms, branched, or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, shea Anomoto, halogen atom, a deuterium atom, or a hydrogen atom Represent. )
The 4-aminocarbazole compound represented by these. Ar ^{1 to} Ar ³ are each independently a phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthryl group, fluorenyl group, benzofluorenyl group, dibenzothienyl group, or dibenzofuranyl group [these groups Each independently represents a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic group having 3 to 18 carbon atoms. alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a carbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, It may have one or more substituents selected from the group consisting of halogen atoms and deuterium atoms]. 4-amino carbazole compound according to claim 1. Ar ⁴ is a phenyl group, a biphenyl group, a naphthyl group, a dibenzothienyl group, or a dibenzofuranyl group [these groups are each independently a methyl group, an ethyl group, a straight chain of 3 to 18 carbon atoms, branched, Or a cyclic alkyl group, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, or a halogenated alkoxy group having 1 to 3 carbon atoms. , a phenyl group, a biphenyl group, a naphthyl group, carbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, halogen atom, and a substituent selected from the group consisting of heavy hydrogen atom The 4-aminocarbazole compound according to any one of claims 1 to 2, which may have one or more kinds. X is a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a fluorene-diyl group (these groups are each independently a methyl group, an ethyl group, a straight chain having 3 to 18 carbon atoms, branched, or A cyclic alkyl group, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, a phenyl group, a biphenyl group, a naphthyl group, carbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, 1 halogen atom, and a substituent selected from the group consisting of heavy hydrogen atom The 4-aminocarbazole compound according to any one of claims 1 to 3, wherein the 4-aminocarbazole compound may be contained in at least one species. R ¹ to R ⁷ are each independently a phenyl group, ethyl group, main butoxy group, an ethoxy group, or is characterized by a hydrogen atom, one of the claims 1 to 4 The 4-aminocarbazole compound according to claim 1. General formula (1)

(In the formula, Ar ^{1 to} Ar ³ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom or sulfur atom). [These groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear or branched chain having 3 to 18 carbon atoms. Or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, phenyl group, biphenyl group, naphthyl group, phenanthryl group , carbazolyl group, 9-phenylcarbazolyl It represents group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, a halogen atom, and a substituent may have one or more members selected from the group consisting of a deuterium atom.
Ar ⁴ is an aromatic hydrocarbon group having 6 to 17 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom, nitrogen atom, or sulfur atom. A methyl group, an ethyl group, a C3-C18 linear, branched or cyclic alkyl group, a methoxy group, an ethoxy group, a C3-C18 linear, branched or cyclic alkoxy group, a carbon number 1 to 3 halogenated alkyl groups, 1 to 3 carbon atoms halogenated alkoxy groups, phenyl groups, biphenyl groups, naphthyl groups , carbazolyl groups, 9-phenylcarbazolyl groups, dibenzothienyl groups, dibenzofuranyl groups, It may have one or more substituents selected from the group consisting of an ano group, a halogen atom, and a deuterium atom.
X is a bivalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, 18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C1-C3 halogenated alkyl group, carbon number 1 ~ 3 halogenated alkoxy group, a phenyl group, consisting of a biphenyl group, a naphthyl group, carbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, halogen atom, and deuterium atoms It may have one or more substituents selected from the group].
R ^{1 to} R ⁷ are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms. , a methoxy group, an ethoxy group, a straight chain 3 to 18 carbon atoms, branched, or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, shea Anomoto, halogen atom, a deuterium atom, or a hydrogen atom Represent. )
An organic EL device comprising a 4-aminocarbazole compound represented by the formula: at least one of a light emitting layer, a hole transport layer, and a hole injection layer. General formula (1)

(In the formula, Ar ^{1 to} Ar ³ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom or sulfur atom). [These groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear or branched chain having 3 to 18 carbon atoms. Or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, phenyl group, biphenyl group, naphthyl group, phenanthryl group, carbazolyl group, 9-phenylcarbazolyl It represents group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, a halogen atom, and a substituent may have one or more members selected from the group consisting of a deuterium atom.
Ar ⁴ is an aromatic hydrocarbon group having 6 to 17 carbon atoms, or a heteroaromatic group having 3 to 20 carbon atoms containing at least one oxygen atom, nitrogen atom, or sulfur atom. A methyl group, an ethyl group, a C3-C18 linear, branched or cyclic alkyl group, a methoxy group, an ethoxy group, a C3-C18 linear, branched or cyclic alkoxy group, a carbon number 1 to 3 halogenated alkyl groups, 1 to 3 carbon atoms halogenated alkoxy groups, phenyl groups, biphenyl groups, naphthyl groups , carbazolyl groups, 9-phenylcarbazolyl groups, dibenzothienyl groups, dibenzofuranyl groups, It may have one or more substituents selected from the group consisting of an ano group, a halogen atom, and a deuterium atom.
X is a bivalent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a divalent heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, 18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C1-C3 halogenated alkyl group, carbon number 1 ~ 3 halogenated alkoxy group, a phenyl group, consisting of a biphenyl group, a naphthyl group, carbazolyl group, 9-phenylcarbazolyl group, dibenzothienyl group, a dibenzofuranyl group, shea Anomoto, halogen atom, and deuterium atoms It may have one or more substituents selected from the group].
R ^{1 to} R ⁷ are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms. , a methoxy group, an ethoxy group, a straight chain 3 to 18 carbon atoms, branched, or cyclic alkoxy group, a halogenated alkyl group having 1 to 3 carbon atoms, shea Anomoto, halogen atom, a deuterium atom, or a hydrogen atom Represent. )
A hole transport material, a hole injection material, or a light-emitting material containing a 4-aminocarbazole compound represented by the formula: