JP6032107B2 - 2,5-Diaminocarbazole compound and use thereof - Google Patents

Description

  The present invention relates to a novel 2,5-diaminocarbazole 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 reducing the driving voltage and increasing the light emission efficiency of the organic EL element.

  In recent years, as a hole transport material, a material having a moderately high ionization potential and a high triplet level suitable for a phosphorescent light emitting device has been developed. This is because a hole transport material having a low ionization potential forms an exciplex with an adjacent light emitting layer to lower the light emission efficiency of the organic EL device, and a phosphorescent light emitting material is used for a compound having a low triplet level. This is because excitation energy confinement in the light emitting layer is insufficient and a highly efficient organic EL device cannot be obtained.

  NPD is known as a hole transport material having a moderately high ionization potential. However, NPD has a problem that the triplet level is low and the light emission efficiency in the phosphorescent light emitting device is not so high.

  As a hole transport material having a moderately high ionization potential and a high triplet level, 2-aminocarbazole compounds (see, for example, Patent Documents 1 and 2) are known. A 2-aminocarbazole compound exhibits higher luminous efficiency than NPD in a green phosphorescent device, but has a problem in that oxidation stability is not sufficiently high, and development of a material excellent in oxidation stability has been demanded.

KR2009-0129799 JP 2011-001349 A

  The present invention has been made in view of the above-mentioned background art, and has an object of having an appropriate ionization potential and a high triplet level, and is more oxidized than a conventionally known 2-aminocarbazole compound. The object is to provide a compound having excellent stability.

  As a result of intensive studies, the present inventors have found that the 2,5-diaminocarbazole compound represented by the following general formula (1) has an appropriate ionization potential and a high triplet level, and is excellent in oxidation stability. The present invention has been completed.

（式中、
Ａｒ^１〜Ａｒ^４は、各々独立して、炭素数６〜２０の芳香族炭化水素基又は炭素数３〜２０のヘテロ芳香族基［これらの基は、各々独立して、メチル基、エチル基、炭素数３〜１８の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数３〜１８の直鎖、分岐、若しくは環状のアルコキシ基、炭素数１〜３のハロゲン化アルキル基、炭素数１〜３のハロゲン化アルコキシ基、炭素数６〜２０のアリール基、炭素数６〜１８のアリールオキシ基、炭素数３〜２０のヘテロアリール基、炭素数３〜１８のトリアルキルシリル基、炭素数１８〜４０のトリアリールシリル基、シアノ基、ハロゲン原子、及び重水素原子からなる群より選ばれる置換基を１種以上有していてもよい］を表す。
Ａｒ^５は炭素数６〜１７の芳香族炭化水素基又は炭素数３〜２０のヘテロ芳香族基［これらの基は、各々独立して、メチル基、エチル基、炭素数３〜１８の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数３〜１８の直鎖、分岐、若しくは環状のアルコキシ基、炭素数１〜３のハロゲン化アルキル基、炭素数１〜３のハロゲン化アルコキシ基、炭素数６〜１２のアリール基、炭素数６〜１８のアリールオキシ基、炭素数３〜２０のヘテロアリール基、炭素数３〜１８のトリアルキルシリル基、炭素数１８〜４０のトリアリールシリル基、シアノ基、ハロゲン原子、及び重水素原子からなる群より選ばれる置換基を１種以上有していてもよい］を表す。
Ｒ^１〜Ｒ^６は、各々独立して、炭素数６〜２０の芳香族炭化水素基、炭素数３〜２０のヘテロ芳香族基［これらの基は、各々独立して、メチル基、エチル基、炭素数３〜１８の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数３〜１８の直鎖、分岐、若しくは環状のアルコキシ基、炭素数１〜３のハロゲン化アルキル基、炭素数６〜２０のアリール基、シアノ基、ハロゲン原子、及び重水素原子からなる群より選ばれる置換基を１種以上有していてもよい］、メチル基、エチル基、炭素数３〜１８の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数３〜１８の直鎖、分岐、若しくは環状のアルコキシ基、炭素数１〜３のハロゲン化アルキル基、炭素数６〜１８のアリールオキシ基、炭素数３〜１８のトリアルキルシリル基、炭素数１８〜４０のトリアリールシリル基、シアノ基、ハロゲン原子、重水素原子、又は水素原子を表す。）
即ち本発明は、上記の一般式（１）で表される２，５−ジアミノカルバゾール化合物、及びその用途に関する。

(Where
Ar ^{1 to} Ar ⁴ 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 or 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 alkoxy group having 3 to 18 carbon atoms, or an alkyl halide having 1 to 3 carbon atoms Group, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, trialkyl having 3 to 18 carbon atoms And may have one or more substituents selected from the group consisting of a silyl group, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom].
Ar ⁵ is an aromatic hydrocarbon group having 6 to 17 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, or a straight chain having 3 to 18 carbon atoms. A branched or 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 halogen having 1 to 3 carbon atoms Alkoxy group, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, 18 to 40 carbon atoms It may have one or more substituents selected from the group consisting of a triarylsilyl group, a cyano group, a halogen atom, and a deuterium atom].
R ^{1 to} R ⁶ 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 or 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 alkoxy group having 3 to 18 carbon atoms, or an alkyl halide having 1 to 3 carbon atoms Group, an aryl group having 6 to 20 carbon atoms, a cyano group, a halogen atom, and one or more substituents selected from the group consisting of deuterium atoms may be present], a methyl group, an ethyl group, and 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 6-18 aryloxy groups, carbon Trialkylsilyl group having 3 to 18, 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 2,5-diaminocarbazole compound represented by the above general formula (1) and its use.

  The organic EL device using the 2,5-diaminocarbazole compound of the present invention is superior in oxidation stability as compared with a material in which a conventionally known carbazole ring is introduced, and further has high luminous efficiency (current efficiency) and low driving voltage. It showed a remarkable effect of excellent durability.

  ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to provide an organic EL element with a high brightness | luminance and efficiency and a long lifetime.

  Hereinafter, the present invention will be described in detail.

In the 2,5-diaminocarbazole compound represented by the general formula (1), Ar ^{1 to} Ar ⁴ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heterogeneity having 3 to 20 carbon atoms. Aromatic groups (these 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, Branched or cyclic 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 20 carbon atoms, aryloxy group having 6 to 18 carbon atoms, carbon 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; It represents a may have seeds or higher).

The aromatic hydrocarbon group having 6 to 20 carbon atoms in Ar ^{1 to} Ar ⁴ is not particularly limited, and examples thereof include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, and a benzofluorenyl group. Group, dibenzofluorenyl group, phenanthryl group, fluoranthenyl group, anthryl group, chrycenyl group, pyrenyl group, triphenylene group, perylenyl group and the like.

Although it does not specifically limit as a C3-C20 heteroaromatic group in Ar < ¹ > -Ar < ⁴ >, For example, C3-C20 containing at least 1 oxygen atom, a nitrogen atom, or a sulfur atom The heteroaromatic group can be raised and is not particularly limited.For example, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, Pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, indolyl group, benzothienyl group, benzofuranyl group, benzoimidazolyl group, indazolyl group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl Group, benzoxazolyl group, benzoisoxazolyl group, 2,1,3 Benzoxadiazolyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolyl group, carbazolyl group, dibenzothienyl group, a dibenzofuranyl group, phenoxazinyl group, phenothiazinyl group, a phenazine group, thianthrenyl group, and the like.

The straight-chain, branched or cyclic alkyl group having 3 to 18 carbon atoms that Ar ^{1 to} Ar ⁴ may have as a substituent is not particularly limited, and examples thereof include a propyl group, an isopropyl group, Examples thereof include a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, a cyclopropyl group, and a cyclohexyl group.

The straight-chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms that Ar ^{1 to} Ar ⁴ may have as a substituent is not particularly limited, and examples thereof include a propoxy group and an isopropoxy group. N-butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, stearyloxy group and the like.

Although it does not specifically limit as a C1-C3 halogenated alkyl group which Ar < ¹ > -Ar < ⁴ > may have as a substituent, For example, a trifluoromethyl group, a trichloromethyl group, 2-fluoro An ethyl group etc. are mentioned.

The C1-C3 halogenated alkoxy group that Ar ^{1 to} Ar ⁴ may have as a substituent is not particularly limited, and examples thereof include a trifluoromethoxy group, a trichloromethoxy group, and 2-fluoro An ethoxy group etc. are mentioned.

The aryl group having 6 to 20 carbon atoms that Ar ^{1 to} Ar ⁴ may have as a substituent is not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, and a 3-methylphenyl group. 4-methylphenyl group, 2-methoxyphenyl group, 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 group and the like.

The aryloxy group having 6 to 18 carbon atoms that Ar ^{1 to} Ar ⁴ may have as a substituent is not particularly limited, and examples thereof include a phenoxy group, a 2-methylphenoxy group, and 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 Group, 2,6-dimethylphenoxy group, biphenyloxy group, naphthyloxy group and the like.

The C3-C20 heteroaryl group that Ar ^{1 to} Ar ⁴ may have as a substituent is not particularly limited, and examples thereof include a pyrrolyl group, a 1-methylpyrrolyl group, and 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-phenyl Imidazolyl, 2-phenyl-imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrimidyl, pyrazyl, 1,3,5-triazyl, 2,4-diphenyl-1 , 3,5-triazyl group, indolyl group, benzothienyl group, benzofuranyl group, ben Imidazolyl group, 2-methylbenzimidazolyl group, 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, benzoisoxazolyl group, 2,1,3-benzoxazodiazolyl 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, thianthre Group, and the like.

The trialkylsilyl group having 3 to 18 carbon atoms that Ar ^{1 to} Ar ⁴ may have as a substituent is not particularly limited, and examples thereof include a trimethylsilyl group, a triethylsilyl group, and a tributylsilyl group. Can be mentioned.

Although it does not specifically limit as a C1-C40 triarylsilyl group which Ar < ¹ > -Ar < ⁴ > may have as a substituent, For example, a triphenylsilyl group, a tri (2-methylphenyl) Examples thereof include a silyl group, a tri (3-methylphenyl) silyl group, a tri (4-methylphenyl) silyl group, and a tri (4-biphenyl) silyl group.

Examples of the halogen atom that Ar ^{1 to} Ar ⁴ may have as a substituent include fluorine, chlorine, bromine, and iodine.

Specific examples of Ar ^{1 to} 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-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, 1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl-3,4-dimethyl-1-imidazolyl group, 2,3,4-trif Nyl-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-Dibiphenyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group, 1-methyl-4-pyrazolyl group, 1-phenyl-4- Pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-phenyl-5-pyrazolyl group, 2-thiazolyl 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, pyrazyl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3, 5-triazin-2-yl group, 1-benzimidazolyl group, 2-methyl-1-benzimidazolyl group, 2-phenyl-1-benzoimidazolyl group, 1-methyl-2-benzoimidazolyl group, 1-phenyl-2-benzoimidazolyl group, 1-methyl-5-benzimidazolyl group, 1,2-dimethyl-5-benzimidazolyl group, 1-methyl-2-phenyl-5-benzimidazolyl group, 1-phenyl-5-benzimidazolyl group, 1,2-diphenyl-5 Benzoimidazolyl group, 1-methyl-6-benzimidazolyl group, 1,2-dimethyl-6-benzimidazolyl group, 1-methyl Ru-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-benzoisothiazolyl 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-benzoxazolyl group, 7-benzoxyl Sazolyl group, 3-benzoisoxazolyl 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-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-phenanthrolin-3-yl group, 1,10-phena Trolin-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, 9-methylcarbazol-2-yl group, 9-methylcarbazol-3-yl group, 9-methylcarbazole- 4-yl group, 9-phenylcarbazol-2-yl group, 9-phenylcarbazol-3-yl group, 9-phenylcarbazol-4-yl group, 9-biphenylcarbazol-2-yl group, 9-biphenylcarbazole- 3-yl group, 9-biphenylcarbazol-4-yl group, 2-thianthryl group, 10-phenylphenothiazine-3 Yl group, 10-phenylphenothiazin-2-yl group, 10-phenylphenoxazin-3-yl group, 10-phenylphenoxazin-2-yl group, 1-methylindol-2-yl group, 1-phenylindole- 2-yl group, 9-phenylcarbazol-4-yl group, 1-methylindol-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-phenylbenzimidazole-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-benzo Thienyl) 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) pheny Group, 3- (2-dibenzofuranyl) phenyl group, 3- (4-dibenzofuranyl) phenyl group, 5-phenylpyridin-2-yl group, 4-phenylpyridin-2-yl group, 5-phenylpyridine Examples thereof include, but are not limited to, a 3-yl group, a 4- (9-carbazolyl) phenyl group, and a 3- (9-carbazolyl) phenyl group.

Ar ^{1 to} Ar ⁴ are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a dibenzothienyl group, because of excellent hole transport properties. Dibenzofuranyl group or carbazolyl 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 3-18 linear, branched or cyclic alkoxy groups, C1-C3 halogenated alkyl groups, C1-C3 halogenated alkoxy groups, C6-C20 aryl groups, C6-C6 18 aryloxy groups, C3-C20 heteroaryl groups, C3-C18 trialkylsilyl groups, C18-C40 triarylsilyl groups, And may have one or more substituents selected from the group consisting of a group, a halogen atom, and a deuterium atom), and each independently represents a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group. Group, fluorenyl group, dibenzothienyl group, dibenzofuranyl group (these groups are each independently a methyl group, an ethyl group, a C3-C18 linear, branched or 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, and an aryl group having 6 to 20 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, a triarylsilyl group having 18 to 40 carbon atoms, More preferably one or more substituents selected from the group consisting of an ano group, a halogen atom, and a deuterium atom), and each independently, a phenyl group, a 4-methylphenyl group, 3-methylphenyl 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, 3 More preferably, it is a -dibenzothienyl group or 3-dibenzofuranyl group.

In the 2,5-diaminocarbazole compound represented by the general formula (1), Ar ⁵ is an aromatic hydrocarbon group having 6 to 17 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms (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, branched, or cyclic alkoxy group having 3 to 18 carbon atoms. Group, C1-C3 halogenated alkyl group, C1-C3 halogenated alkoxy group, C6-C12 aryl group, C6-C18 aryloxy group, C3-C20 hetero It has at least one substituent selected from the 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. Even A).

The aromatic hydrocarbon group of 6 to 17 carbon atoms in Ar ^5, although not particularly limited, for example, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, benzofluorenyl group, a phenanthryl group, an anthryl group , Pyrenyl group, fluoranthenyl group and the like.

The hetero aromatic group having 3 to 20 carbon atoms in Ar ^5, is not particularly ^limited, be exemplified the same substituents as heteroaromatic group having 3 to 20 carbon atoms shown by Ar 1 to Ar ⁴ Can do.

The following substituents that Ar ⁵ may have as a substituent are not particularly limited, and examples thereof include the same substituents as those shown in the aforementioned Ar ^{1 to} Ar ⁴ .
・ C3-C18 straight chain, branched or cyclic alkyl group ・ C3-C18 straight chain, branched or cyclic alkoxy group ・ C1-C3 halogenated alkyl group ・ C1-C1 3 halogenated alkoxy groups, C6-C18 aryloxy groups, C3-C20 heteroaryl groups, C3-C18 trialkylsilyl groups, C18-C40 triarylsilyl groups, halogens The aryl group having 6 to 12 carbon atoms that the atom Ar ⁵ may have as a substituent is not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, and 4 -Methylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl , 3,4-dimethylphenyl group, 2,6-dimethylphenyl group, a biphenyl group, a naphthyl group, and the like.

Specific examples of Ar ⁵ 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-dibiphenyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3- Pyrazolyl group, 1-methyl-4-pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-phenyl-5-pyrazolyl group, 2-thia Ryl 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, Pila Zyl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazin-2-yl group, 1-benzimidazolyl group, 2-methyl-1-benzimidazolyl 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, , 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-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-benzoy Oxazolyl 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-benen Zothienyl 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- 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, -(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- Methylbenzoimidazol-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, -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. Although it can illustrate, it is not limited to these.

Ar ⁵ is a phenyl group, a biphenyl group, a naphthyl group, a dibenzothienyl group from the viewpoint that the 2,5-diaminocarbazole compound represented by the general formula (1) has high molecular planarity and 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, 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 heavy water It may preferably have one or more substituents selected from the group consisting of elementary atoms), and each independently represents a phenyl group, 4-methylphenyl group, 3-methylphenyl group, 4-biphenyl. It is more preferably a group, a 2-naphthyl group, a 3-dibenzothienyl group, or a 3-dibenzofuranyl group.

In the 2,5-diaminocarbazole compound represented by the general formula (1), R ^{1 to} R ⁶ are each independently an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heteroaromatic group having 4 to 20 carbon atoms. Group (these groups are each independently a methyl group, an ethyl group, a straight chain having 3 to 18 carbon atoms, a branched or cyclic alkyl group, a methoxy group, an ethoxy group, or a straight chain having 3 to 18 carbon atoms). A substituent selected from the group consisting 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 cyano group, a halogen atom, and a deuterium atom Or 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, carbon number 1 3 halogenated alkyl groups, aryloxy groups having 6 to 18 carbon atoms, trialkylsilyl groups having 3 to 18 carbon atoms, triarylsilyl groups having 18 to 40 carbon atoms, cyano groups, halogen atoms, deuterium atoms, or Represents a hydrogen atom.

The aromatic hydrocarbon group having 6 to 20 carbon atoms in R ¹ to R ^6, is not particularly limited, and an aromatic hydrocarbon group having 6 to 20 carbon atoms shown in ^Ar 1 to Ar ⁴ of the The same substituents can be mentioned.

The hetero aromatic group having 3 to 20 carbon atoms in R ¹ to R ^6, is not particularly limited, the same substituents as the hetero-aromatic groups of 3 to 20 carbon atoms shown in the above ^Ar 1 to Ar ⁴ Groups.

As the following substituents that the aromatic hydrocarbon group having 6 to 20 carbon atoms and the heteroaromatic group having 3 to 20 carbon atoms in R ^{1 to} R ⁶ may have as a substituent, the above Ar ¹ to The same substituents as those shown for Ar ⁴ can be exemplified.
・ C3-C18 linear, branched, or cyclic alkyl group ・ C3-C18 linear, branched, or cyclic alkoxy group ・ C1-C3 halogenated alkyl group ・ C6-C 20 linear 3 to 18 carbon atoms in the aryl group, a halogen atom R ¹ to R ^6, branched, or the alkyl group of cyclic, but not limited to, illustrated in ^Ar 1 to Ar ⁴ of the Examples thereof include the same substituent as the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms.

Linear 3 to 18 carbon atoms in R ¹ to R ^6, branched, or as a cyclic alkoxy group is not particularly limited, a straight carbon atoms 3 to 18 shown in ^Ar 1 to Ar ⁴ of the Examples include the same substituent as the chain, branched, or cyclic alkoxy group.

Although it does not specifically limit as a C1-C3 halogenated alkyl group in R < ¹ > -R < ⁶ >, The same substitution as the C1-C3 halogenated alkyl group shown in said Ar < ¹ > -Ar < ⁴ >. Groups.

Examples of the aryloxy group having 6 to 18 carbon atoms in R ¹ to R ^6, is not particularly limited, the same substituents as aryloxy group having 6 to 18 carbon atoms shown in ^Ar 1 to Ar ⁴ of the Can be mentioned.

The trialkylsilyl group having 3 to 18 carbon atoms in R ^{1 to} R ⁶ is not particularly limited, but is the same substitution as the trialkylsilyl group having 3 to 18 carbon atoms shown in Ar ^{1 to} Ar ⁴ . Groups.

The triarylsilyl group of 18-40 carbon atoms in R ¹ to R ^6, is not particularly limited, the same substituents as the triarylsilyl group having a carbon number of 18 to 40 shown in ^Ar 1 to Ar ⁴ of the Groups.

Although it does not specifically limit as a halogen atom in R < ¹ > -R < ⁶ >, The same substituent as the halogen atom shown in the said Ar < ¹ > -Ar < ⁴ > is mentioned.

R ^{1 to} R ⁶ are each 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, C3-C18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, C3-C18 linear, branched, or cyclic alkoxy group, C1-C3 halogenated alkyl group And optionally having one or more substituents selected from the group consisting of an aryl group having 6 to 20 carbon atoms, a cyano group, a halogen atom, and a deuterium atom), a methyl group, an ethyl group, and a 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, heavy water 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 More preferably a group, a cyano group, a deuterium atom, or a hydrogen atom, and even more 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 2, 5- diaminocarbazole compound represented by General formula (1), it is not limited to these compounds.

前記一般式（１）で表される２，５−ジアミノカルバゾール化合物は、例えば、ハロゲン化されたカルバゾール中間体を公知の方法（Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ，１９９８年，第３９巻，２３６７頁）でアミノ化することによって合成することができる。具体的には、下記のルートａ及びルートｂにより合成することができる。

For the 2,5-diaminocarbazole compound represented by the general formula (1), for example, a halogenated carbazole intermediate is aminated by a known method (Tetrahedron Letters, 1998, Vol. 39, page 2367). Can be synthesized. Specifically, it can be synthesized by the following route a and route b.

  (Route a) A 9H-carbazole compound having halogenated at the 2-position and 5-position represented by the general formula (2) and a compound having a halogen atom represented by the general formula (3) in the presence of a base The reaction is carried out using a copper catalyst or a palladium catalyst to obtain a 2,5-halogenated-9-substituted carbazole compound represented by the general formula (4). Further, the obtained 2,5-halogenated-9-substituted carbazole compound represented by the general formula (4) and the secondary amine compound represented by the general formula (5) are added with a copper catalyst or The reaction is carried out using a palladium catalyst.

（式中、Ａｒ^１、Ａｒ^２、Ａｒ^５及びＲ^１〜Ｒ^６は前記と同義であり、Ｘ^１〜Ｘ^３は各々独立してハロゲン原子［ヨウ素、臭素、塩素、又はフッ素］を表す。）
（ルートｂ）一般式（６）で表される５位がハロゲン化された２−アリールアミノ−９Ｈ−カルバゾール化合物と、一般式（７）で表されるハロゲン原子を有する化合物とを、塩基の存在下、銅触媒又はパラジウム触媒を用いて反応させ、一般式（８）で表される２−アリールアミノ−５−ハロゲン化−９−置換カルバゾール化合物を得る。更に、得られた一般式（８）で表される２−アリールアミノ−５−ハロゲン化−９−置換カルバゾール化合物と、一般式（９）で表される２級アミン化合物を塩基の存在下、銅触媒又はパラジウム触媒を用いて反応させる。

(In the formula, Ar ¹ , Ar ² , Ar ⁵ and R ^{1 to} R ⁶ are as defined above, and X ^{1 to} X ³ each independently represent a halogen atom [iodine, bromine, chlorine, or fluorine]. )
(Route b) A 2-arylamino-9H-carbazole compound in which the 5-position represented by the general formula (6) is halogenated and a compound having a halogen atom represented by the general formula (7) In the presence, the reaction is performed using a copper catalyst or a palladium catalyst to obtain a 2-arylamino-5-halogenated-9-substituted carbazole compound represented by the general formula (8). Further, the obtained 2-arylamino-5-halogenated-9-substituted carbazole compound represented by the general formula (8) and the secondary amine compound represented by the general formula (9) are added in the presence of a base. The reaction is carried out using a copper catalyst or a palladium catalyst.

（式中、Ａｒ^１〜Ａｒ^５及びＲ^１〜Ｒ^６は前記と同義であり、Ｘ^４及びＸ^５は各々独立してハロゲン原子［ヨウ素、臭素、塩素、又はフッ素］を表す。）
一般式（１）で表される２，５−ジアミノカルバゾール化合物の合成方法は、ルートａ及びルートｂに限定されるものでなく、他のルートによって合成することも可能である。

(In the formula, Ar ^{1 to} Ar ⁵ and R ^{1 to} R ⁶ are as defined above, and X ⁴ and X ⁵ each independently represent a halogen atom [iodine, bromine, chlorine, or fluorine].)
The method for synthesizing the 2,5-diaminocarbazole compound represented by the general formula (1) is not limited to the route a and the route b, and can be synthesized by other routes.

  The 2,5-diaminocarbazole 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 2,5-diaminocarbazole compound represented by the general formula (1) is an element using a fluorescent light-emitting material or a phosphorescent light-emitting material as a light-emitting layer, and includes a hole injection layer, a hole transport layer, and a light-emitting layer. It can be preferably used in any one or more layers.

  The light-emitting layer used when the 2,5-diaminocarbazole 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 is conventionally known. Fluorescent or phosphorescent materials 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.

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

  The 2,5-diaminocarbazole 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 2,5-diaminocarbazole compound represented by the general formula (1) is used as the light emitting layer of the organic EL device, the 2,5-diaminocarbazole compound is used alone, and the known light emitting host material is doped. Or can be used by doping with 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 2,5-diaminocarbazole compound represented by the general formula (1) include a vacuum deposition method, a spin coating method, and a cast method. A known method such as a method can be applied.

The result of the cyclic voltammetry measurement of the compound (A16) obtained in Example 9 is shown. The result of the cyclic voltammetry measurement of the compound (a) obtained in Reference Example 1 is shown.

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

¹ H-NMR and ¹³ C-NMR measurements were performed using Gemini 200 manufactured by Varian.

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

合成例１ （２−ニトロ−６，４’−ジクロロビフェニル［式（１０）］の合成）
窒素気流下、１Ｌの三口フラスコに、２，３−ジクロロニトロベンゼン ５０．０ｇ（２６０．４ｍｍｏｌ）、４−クロロフェニルボロン酸 ４０．７ｇ（２６０．４ｍｍｏｌ）、テトラキス（トリフェニルホスフィン）パラジウム ３．０ｇ（２．６ｍｍｏｌ）、テトラヒドロフラン ２００ｍＬ、４０ｗｔ％のりん酸三カリウム水溶液 ３４５ｇ（６５１．０ｍｍｏｌ）を加え、１０時間加熱還流した。室温まで冷却した後、水層と有機層を分液し、有機層を飽和塩化アンモニウム水溶液と飽和塩化ナトリウム水溶液で洗浄した後、無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣にトルエンを加え、シリカゲルカラムクロマトグラフィー（トルエン）で精製することにより、２−ニトロ−６，４’−ジクロロビフェニルの黄色オイルを６５．０ｇ（２４３．４ｍｍｏｌ）単離した（収率９３％）。

Synthesis Example 1 (Synthesis of 2-nitro-6,4′-dichlorobiphenyl [Formula (10)])
In a 1 L three-necked flask under a nitrogen stream, 2,3-dichloronitrobenzene 50.0 g (260.4 mmol), 4-chlorophenylboronic acid 40.7 g (260.4 mmol), tetrakis (triphenylphosphine) palladium 3.0 g ( 2.6 mmol), tetrahydrofuran (200 mL) and 40 wt% tripotassium phosphate aqueous solution (345 g, 651.0 mmol) were added, and the mixture was heated to reflux for 10 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. Toluene was added to the residue and purified by silica gel column chromatography (toluene) to isolate 65.0 g (243.4 mmol) of yellow oil of 2-nitro-6,4′-dichlorobiphenyl (yield 93%). ).

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

¹ H-NMR (CDCl ₃ ); 7.73 (t, 2H), 7.45 (t, 1H), 7.42 (d, 2H), 7.19 (d, 2H)
¹³ C-NMR (CDCl ₃ ); 135.21, 134.37, 132.94, 131.84, 129.63, 128.75, 128.31, 121.63
Synthesis Example 2 (Synthesis of 2,5-dichlorocarbazole [Formula (11)])
In a 1 L three-necked flask under a nitrogen stream, 61.0 g (228.4 mmol) of 2-nitro-6,4′-dichlorobiphenyl obtained in Synthesis Example 1, 149.6 g (571.17 mmol) of triphenylphosphine, o- 300 ml of dichlorobenzene was charged and stirred at 150 ° C. for 16 hours. O-Dichlorobenzene was distilled off under reduced pressure, toluene was added to the residue, and the residue was purified by silica gel column chromatography (toluene). The obtained pale yellow powder was further washed with hexane, and 40.2 g (171.3 mmol) of a white powder of 2,5-dichlorocarbazole was isolated (yield 75%).

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

¹ H-NMR (CDCl ₃ ); 8.41 (d, 1H), 7.97 (br-s, 1H), 7.16-7.33 (m, 5H)
¹³ C-NMR (CDCl ₃ ); 140.07, 139.31, 131.57, 128.03, 125.97, 123.27, 120.34, 120.20, 119.90, 109.87, 108 .57
Synthesis Example 3 (Synthesis of 2,5-dichloro-9-phenylcarbazole [Formula (12)])
Under a nitrogen stream, 7.0 g (29.7 mmol) of 2,5-dichlorocarbazole obtained in Synthesis Example 2 in a 100 mL three-necked flask, 5.1 g (32.7 mmol) of bromobenzene, 9.0 g of potassium carbonate (65. 5 mmol), o-xylene 40 mL, palladium acetate 73 mg (0.32 mmol), tri (tert-butyl) phosphine 231 mg (1.14 mmol) were added, and the mixture was stirred at 140 ° C. for 12 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 pure 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 = 1: 5)), and 8.3 g (26.6 mmol) of white powder of 2,5-dichloro-9-phenylcarbazole was isolated. (89% yield).

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

¹ H-NMR (CDCl ₃ ); 8.54 (d, 1H), 7.45-7.64 (m, 5H), 7.18-7.31 (m, 5H)
¹³ C-NMR (CDCl ₃ ); 141.86, 141.15, 136.07, 131.86, 129.63, 128.13, 127.85, 126.83, 125.91, 123.38, 120 58, 120.27, 109.16, 107.82
Example 1 (Synthesis of Compound (A16))
In a 200 mL three-necked flask under a nitrogen stream, 5.0 g (16.0 mmol) of 2,5-dichloro-9-phenylcarbazole obtained in Synthesis Example 3 and 10.8 g (33.7 mmol) of N, N-bisbiphenylamine were obtained. ), 4.3 g (44.9 mmol) of sodium-tert-butoxide, 60 mL of o-xylene, 72 mg (0.32 mmol) of palladium acetate, and 226 mg (1.12 mmol) of tri (tert-butyl) phosphine at 140 ° C. Stir for 6 hours. After cooling to room temperature, 30 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: 2)), and the obtained solid was recrystallized from toluene to obtain 10 white compound (A16) powder. 0.1 g (11.4 mmol) was isolated (71% yield).

  The compound was identified by FDMS measurement.

FDMS: 881
Example 2 (Synthesis of Compound (A20))
In a 100 mL three-necked flask under a nitrogen stream, 3.1 g (10.0 mmol) of 2,5-dichloro-9-phenylcarbazole obtained in Synthesis Example 3 and N- (p-tolyl) -N-biphenylamine 5. 4 g (21.0 mmol), sodium-tert-butoxide 2.6 g (28.0 mmol), o-xylene 40 mL, palladium acetate 44 mg (0.20 mmol), tri (tert-butyl) phosphine 141 mg (0.70 mmol) were added. And stirred at 140 ° C. for 4 hours. After cooling to room temperature, 20 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: 2)), and 6.2 g (8.2 mmol) of glassy solid of compound (A20) was isolated (yield 82 %).

  The compound was identified by FDMS measurement.

FDMS: 757
Example 3 (Synthesis of Compound (A35))
In a 50 mL three-neck flask under a nitrogen stream, 1.5 g (4.8 mmol) of 2,5-dichloro-9-phenylcarbazole obtained in Synthesis Example 3 and 3.2 g (10 of N-phenyl-N-terphenylamine) 0.1 mmol), 1.3 g (13.4 mmol) of sodium-tert-butoxide, 15 mL of o-xylene, 20 mg (0.09 mmol) of palladium acetate, 63 mg (0.31 mmol) of tri (tert-butyl) phosphine and 140 Stir at 4 ° C. for 4 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: 2)), and 3.6 g (4.1 mmol) of a glassy solid of the compound (A35) was isolated (yield 86 %).

  The compound was identified by FDMS measurement.

FDMS: 881
Example 4 (Synthesis of Compound (A61))
In a 100 mL three-necked flask under a nitrogen stream, 4.0 g (12.8 mmol) of 2,5-dichloro-9-phenylcarbazole obtained in Synthesis Example 3 and N-phenyl-N- (2-dibenzothienyl) amine 7 .3 g (26.8 mmol), sodium-tert-butoxide 3.4 g (35.8 mmol), o-xylene 40 mL, palladium acetate 57 mg (0.25 mmol), tri (tert-butyl) phosphine 176 mg (0.87 mmol) The mixture was added and stirred at 140 ° C. for 6 hours. After cooling to room temperature, 20 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: 2)), and 7.9 g (10.1 mmol) of a glassy solid of compound (A61) was isolated (yield 79 %).

  The compound was identified by FDMS measurement.

FDMS: 789
Example 5 (Evaluation of Triplet Level of Compound (A16))
A solution in which the compound (A16) was dissolved in 2-methyltetrahydrofuran at a concentration of 0.0001 mol / L was prepared, and the phosphorescence spectrum was measured under liquid nitrogen cooling. The maximum wavelength of the phosphorescence spectrum was 485 nm. The triplet level estimated from the maximum wavelength was 2.55 eV, which was higher than the triplet level of NPD (2.36 eV) estimated by the same method.

Example 6 (Evaluation of Triplet Level of Compound (A20))
With respect to compound (A20), a phosphorescence spectrum was measured by the same method as in Example 5. The maximum wavelength of the phosphorescence spectrum was 483 nm. The triplet level estimated from the maximum wavelength was 2.56 eV, which was higher than the triplet level (2.36 eV) of NPD estimated by the same method.

Example 7 (Evaluation of Triplet Level of Compound (A35))
With respect to compound (A35), a phosphorescence spectrum was measured by the same method as in Example 5. The maximum wavelength of the phosphorescence spectrum was 511 nm. The triplet level estimated from the maximum wavelength was 2.42 eV, which was higher than the triplet level (2.36 eV) of NPD estimated by the same method.

Example 8 (Evaluation of Triplet Level of Compound (A61))
With respect to compound (A61), a phosphorescence spectrum was measured by the same method as in Example 5. The maximum wavelength of the phosphorescence spectrum was 467 nm. The triplet level estimated from the maximum wavelength was 2.65 eV, which was higher than the triplet level of NPD (2.36 eV) estimated by the same method.

Example 9 (Evaluation of ionization potential of compound (A16))
Compound (A16) was dissolved at a concentration of 0.001 mol / L in an anhydrous dichloromethane solution having a tetrabutylammonium perchlorate concentration of 0.1 mol / L, and the ionization potential was measured by cyclic voltammetry. Glassy carbon was used for the working electrode, platinum wire was used for the counter electrode, and silver wire immersed in an acetonitrile solution of AgNO ₃ was used for the reference electrode. Ferrocene is used as the standard substance, and the ionization potential of the compound (A16) based on the oxidation-reduction potential of ferrocene is 0.31 V vs. Fc / Fc ⁺ . This value is equivalent to the ionization potential (0.32 V vs. Fc / Fc ⁺ ) of NPD conventionally known as a hole transport material, and was a preferable ionization potential as a hole transport material. In addition, a cyclic voltammogram of the compound (A16) is shown in FIG. The compound (A16) was reversible in both one-electron oxidation and two-electron oxidation, and the dicationic state subjected to two-electron oxidation was also stable.

Example 10 (Evaluation of ionization potential of compound (A20))
The ionization potential of the compound (A20) was evaluated in the same manner as in Example 9. The ionization potential of the compound (A20) based on the oxidation-reduction potential of ferrocene is 0.30 V vs. Fc / Fc ^+, which is equivalent to the ionization potential (0.31 V vs. Fc / Fc ⁺ ) of NPD that has been conventionally known as a hole transport material, and was a preferable ionization potential as a hole transport material. Compound (A20) was reversible in both one-electron oxidation and two-electron oxidation, and the dicationic state after two-electron oxidation was stable.

Example 11 (Evaluation of ionization potential of compound (A35))
The ionization potential of the compound (A35) was evaluated in the same manner as in Example 9. The ionization potential of the compound (A35) based on the oxidation-reduction potential of ferrocene is 0.35 V vs. Fc / Fc ^+, which is equivalent to the ionization potential (0.31 V vs. Fc / Fc ⁺ ) of NPD that has been conventionally known as a hole transport material, and was a preferable ionization potential as a hole transport material. In addition, compound (A35) was reversible in both one-electron oxidation and two-electron oxidation, and the dicationic state subjected to two-electron oxidation was also stable.

Example 12 (Evaluation of ionization potential of compound (A61))
The ionization potential of the compound (A61) was evaluated in the same manner as in Example 9. The ionization potential of the compound (A61) based on the oxidation-reduction potential of ferrocene is 0.31 V vs. Fc / Fc ^+, which is equivalent to the ionization potential (0.31 V vs. Fc / Fc ⁺ ) of NPD that has been conventionally known as a hole transport material, and was a preferable ionization potential as a hole transport material. Compound (A61) was reversible in both one-electron oxidation and two-electron oxidation, and the dicationic state subjected to two-electron oxidation was also stable.

参考例１ （化合物（ａ）のイオン化ポテンシャルの評価）
実施例９と同様の方法でカルバゾール環の２位にアミノ基が結合した化合物（ａ）のイオン化ポテンシャルを評価した。化合物（ａ）のイオン化ポテンシャルは０．３５Ｖ ｖｓ．Ｆｃ／Ｆｃ^＋であり、従来から正孔輸送材料として知られているＮＰＤのイオン化ポテンシャル（０．３１Ｖ ｖｓ．Ｆｃ／Ｆｃ^＋）と同等であった。また、化合物（ａ）のサイクリックボルタモグラムを図２に示す。化合物（ａ）は、１電子酸化に対しては可逆であったが、２電子酸化に対しては不可逆であった。

Reference Example 1 (Evaluation of ionization potential of compound (a))
The ionization potential of the compound (a) having an amino group bonded to the 2-position of the carbazole ring was evaluated in the same manner as in Example 9. The ionization potential of the compound (a) is 0.35 V vs. Fc / Fc ⁺ , which was equivalent to the ionization potential (0.31 V vs. Fc / Fc ⁺ ) of NPD, which has been conventionally known as a hole transport material. Moreover, the cyclic voltammogram of a compound (a) is shown in FIG. Compound (a) was reversible for one-electron oxidation but irreversible for two-electron oxidation.

比較例１ （化合物（ｂ）のイオン化ポテンシャルの評価）
実施例９と同様の方法でカルバゾール環の３位にアミノ基が結合した化合物（ｂ）のイオン化ポテンシャルを評価した。化合物（ｂ）のイオン化ポテンシャルは０．１３Ｖ ｖｓ．Ｆｃ／Ｆｃ^＋であり、従来から正孔輸送材料として知られているＮＰＤのイオン化ポテンシャル（０．３１Ｖ ｖｓ．Ｆｃ／Ｆｃ^＋）と比較すると低く、正孔輸送材料としては好ましくないイオン化ポテンシャルであった。

Comparative Example 1 (Evaluation of ionization potential of compound (b))
In the same manner as in Example 9, the ionization potential of the compound (b) having an amino group bonded to the 3-position of the carbazole ring was evaluated. The ionization potential of the compound (b) is 0.13 V vs. Compared to the ionization potential of NPD (0.31 V vs. Fc / Fc ⁺ ), which is conventionally known as a hole transport material, it is an Fc / Fc ⁺ and is an unfavorable ionization potential as a hole transport material. It was.

Example 13 (Element evaluation of compound (A16))
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. Subsequently, NPD was deposited at a deposition rate of 0.3 nm / second to 25 nm, and then compound (A16) was deposited at a deposition rate of 0.1 nm / second to 5 nm to form two hole transport layers. Subsequently, tris (2-phenylpyridine) iridium (Ir (ppy) ₃ ) as a phosphorescent dopant material and 4,4′-bis (N-carbazolyl) biphenyl (CBP) as a host material have a weight ratio of 1:11. Co-deposited at a deposition rate of 0.25 nm / second to obtain a 30 nm emission layer. Next, BAlq (bis (2-methyl-8-quinolinolato) (p-phenylphenolato) aluminum) was deposited at a deposition rate of 0.3 nm / second to form a 5 nm exciton block layer, and then Alq ₃ (Tris). (8-quinolinolato) aluminum) was deposited at 0.3 nm / second to form a 45 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 1.

Example 14 (Device Evaluation of Compound (A20))
An organic EL device was produced in the same manner as in Example 13 except that the compound (A16) was changed to the compound (A20). Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm ² was applied.

Example 15 (Element Evaluation of Compound (A35))
An organic EL device was produced in the same manner as in Example 13 except that the compound (A16) was changed to the compound (A35). Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm ² was applied.

Example 16 (Element Evaluation of Compound (A61))
An organic EL device was produced in the same manner as in Example 13 except that the compound (A16) was changed to the compound (A61). Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm ² was applied.

Comparative Example 2
An organic EL device was produced in the same manner as in Example 13 except that the compound (A16) was changed to NPD. Table 1 shows the driving voltage and current efficiency when a current of 20 mA / cm ² was applied.

Comparative Example 3
An organic EL device was produced in the same manner as in Example 13 except that the compound (A16) was changed to the compound (b). Table 1 shows the drive voltage and current efficiency when a current of 20 mA / cm ² was applied.

  The 2,5-diaminocarbazole compound of the present invention showed higher current efficiency (luminous efficiency) than NPD and compound (b). In the device using the 2,5-diaminocarbazole compound, the driving voltage could be suppressed low.

Claims (6)

General formula (1)

(Where
Ar ^{1 to} Ar ⁴ 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 or 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 alkoxy group having 3 to 18 carbon atoms, or an alkyl halide having 1 to 3 carbon atoms Group, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, trialkyl having 3 to 18 carbon atoms And may have one or more substituents selected from the group consisting of a silyl group, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom].
Ar ⁵ is an aromatic hydrocarbon group having 6 to 17 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, or a straight chain having 3 to 18 carbon atoms. A branched or 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 halogen having 1 to 3 carbon atoms Alkoxy group, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, 18 to 40 carbon atoms It may have one or more substituents selected from the group consisting of a triarylsilyl group, a cyano group, a halogen atom, and a deuterium atom].
R ^{1 to} R ⁶ 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 or 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 alkoxy group having 3 to 18 carbon atoms, or an alkyl halide having 1 to 3 carbon atoms Group, an aryl group having 6 to 20 carbon atoms, a cyano group, a halogen atom, and one or more substituents selected from the group consisting of deuterium atoms may be present], a methyl group, an ethyl group, and 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 6-18 aryloxy groups, carbon Trialkylsilyl group having 3 to 18, triarylsilyl group of 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom. )
The 2,5-diaminocarbazole compound represented by these. Ar ^{1 to} Ar ⁴ each independently represents a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a dibenzothienyl group, a dibenzofuranyl group, or a carbazolyl 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 linear or branched group having 3 to 18 carbon atoms, Or a cyclic alkoxy group, a C1-C3 halogenated alkyl group, a C1-C3 halogenated alkoxy group, a C6-C20 aryl group, a C6-C18 aryloxy group, a C3-C3 ˜20 heteroaryl group, C 3-18 trialkylsilyl group, C 18-40 triarylsilyl group, cyano group, halogen atom, and heavy water Characterized in that a substituent selected from the group consisting of atoms have one or more also may), 2,5-aminocarbazole compound according to claim 1. Ar ⁵ 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 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, or 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 a triarylsilyl group having 18 to 40 carbon atoms 3 or 3 which may have one or more substituents selected from the group consisting of a group, a cyano group, a halogen atom, and a deuterium atom). 2,5-diaminocarbazole compound. R ^{1 to} R ⁶ are each independently 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, or a carbon number of 3 to 18). A linear, branched or 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 carbon number of 6 to (May have one or more substituents selected from the group consisting of 20 aryl groups, cyano groups, halogen atoms, and deuterium atoms) Methyl group, ethyl group, C3-C18 straight chain, 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, an aryloxy group having 6 to 18 carbon atoms, a cyano group, a deuterium atom, or a hydrogen atom Characterized in that there, 2,5-aminocarbazole compound according to any one of claims 1 to 3. General formula (1)

(Where
Ar ^{1 to} Ar ⁴ 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 or 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 alkoxy group having 3 to 18 carbon atoms, or an alkyl halide having 1 to 3 carbon atoms Group, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, trialkyl having 3 to 18 carbon atoms And may have one or more substituents selected from the group consisting of a silyl group, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom].
Ar ⁵ is an aromatic hydrocarbon group having 6 to 17 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, or a straight chain having 3 to 18 carbon atoms. A branched or 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 halogen having 1 to 3 carbon atoms Alkoxy group, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, 18 to 40 carbon atoms It may have one or more substituents selected from the group consisting of a triarylsilyl group, a cyano group, a halogen atom, and a deuterium atom].
R ^{1 to} R ⁶ 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 or 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 alkoxy group having 3 to 18 carbon atoms, or an alkyl halide having 1 to 3 carbon atoms Group, an aryl group having 6 to 20 carbon atoms, a cyano group, a halogen atom, and one or more substituents selected from the group consisting of deuterium atoms may be present], a methyl group, an ethyl group, and 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 6-18 aryloxy groups, carbon Trialkylsilyl group having 3 to 18, triarylsilyl group of 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom. )
An organic EL device comprising a 2,5-diaminocarbazole 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)

(Where
Ar ^{1 to} Ar ⁴ 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 or 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 alkoxy group having 3 to 18 carbon atoms, or an alkyl halide having 1 to 3 carbon atoms Group, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, trialkyl having 3 to 18 carbon atoms And may have one or more substituents selected from the group consisting of a silyl group, a triarylsilyl group having 18 to 40 carbon atoms, a cyano group, a halogen atom, and a deuterium atom].
Ar ⁵ is an aromatic hydrocarbon group having 6 to 17 carbon atoms or a heteroaromatic group having 3 to 20 carbon atoms [these groups are each independently a methyl group, an ethyl group, or a straight chain having 3 to 18 carbon atoms. A branched or 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 halogen having 1 to 3 carbon atoms Alkoxy group, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, trialkylsilyl group having 3 to 18 carbon atoms, 18 to 40 carbon atoms It may have one or more substituents selected from the group consisting of a triarylsilyl group, a cyano group, a halogen atom, and a deuterium atom].
R ^{1 to} R ⁶ 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 or 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 alkoxy group having 3 to 18 carbon atoms, or an alkyl halide having 1 to 3 carbon atoms Group, an aryl group having 6 to 20 carbon atoms, a cyano group, a halogen atom, and one or more substituents selected from the group consisting of deuterium atoms may be present], a methyl group, an ethyl group, and 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 6-18 aryloxy groups, carbon Trialkylsilyl group having 3 to 18, triarylsilyl group of 18 to 40 carbon atoms, a cyano group, a halogen atom, a deuterium atom, or a hydrogen atom. )
A hole transport material, a hole injection material, or a light-emitting material containing a 2,5-diaminocarbazole compound represented by the formula:

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