JP4377783B2 - Triarylamine compound and organic electroluminescent device containing the triarylamine compound - Google Patents

Description

  The present invention relates to a novel triarylamine compound and an organic electroluminescent device comprising the triarylamine compound.

  In recent years, with the development of displays, display materials with high definition, high brightness, high-speed response, low power consumption, and wide viewing angles are required. As one of them, it has been proposed that an organic electroluminescence element (organic electroluminescence element: organic EL element) using an organic material as a light emitting material is useful.

An organic electroluminescent device has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode. By injecting electrons and holes into the thin film and recombining them, an exciton (Exington) ) And emits light using light emitted when the exciton is deactivated [Non-Patent Document 1]. An organic electroluminescent element can emit light at a low direct current voltage of about several volts to several tens of volts, and is expected to be applied to various light emitting elements, display elements, and the like. However, organic electroluminescent elements generally have a short light emission life and are not sufficiently practical in durability. As one of the reasons, it is known that the organic electroluminescent element generates heat when driven, and the organic material in the element is deteriorated by the heat. Therefore, in order to improve the durability of the organic electroluminescence device, it is considered that increasing the glass transition point (Tg) of each organic material is effective for improving the durability of the device and extending the light emission lifetime. ing. As a method for improving the emission lifetime and durability, for example, organic electroluminescent elements using a triarylamine compound have been proposed (for example, Patent Documents 1 and 2). However, it cannot be said that these light-emitting elements also have a sufficiently satisfying light-emission lifetime and durability, and at present, new and improved compounds are desired.
JP 2004-203765 A WO02 / 30159 A1 Appl.Phys.Lett., 51,913 (1987)

  An object of the present invention is to provide a novel triarylamine compound and a novel light-emitting device containing the compound. More specifically, for example, it is to provide a triarylamine compound that can be suitably used for a light-emitting material of an organic electroluminescent device, and an organic electroluminescent device containing the compound.

In order to solve the above-mentioned problems, the present inventors have intensively studied various triarylamine compounds, in particular, triarylamine compounds that can be suitably used for charge injection transport materials and light emitting layers of organic electroluminescent devices. As a result, the present invention has been completed. That is, the present invention
<1>: Triarylamine compound represented by the general formula (1),

[Wherein, Ar ^{1 to} Ar ³ each independently represents a substituted or unsubstituted aryl group, and Z ^{1 to} Z ⁸ each independently represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, It represents a chain, branched or cyclic alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group. Moreover, the adjacent groups of Z ^{1 to} Z ⁸ may form a ring together with the adjacent groups. ]

<2>: An organic electroluminescent device comprising at least one layer containing at least one triarylamine compound represented by the general formula (1) between a pair of electrodes,
It is about.

  According to the present invention, it is possible to provide a novel triarylamine compound and an organic electroluminescence device having a long emission lifetime and excellent durability.

  Hereinafter, the present invention will be described in detail.

  The triarylamine compound of the present invention is a compound represented by the general formula (1).

[Wherein, Ar ^{1 to} Ar ³ each independently represents a substituted or unsubstituted aryl group, and Z ^{1 to} Z ⁸ each independently represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, It represents a chain, branched or cyclic alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group. Moreover, the adjacent groups of Z ^{1 to} Z ⁸ may form a ring together with the adjacent groups. ]

In the compound represented by the general formula (1), Ar ^{1 to} Ar ³ each independently represents a substituted or unsubstituted aryl group. Ar ^{1 to} Ar ³ are preferably each independently a substituted or unsubstituted aryl group having 5 to 38 carbon atoms, and more preferably a substituted or unsubstituted aryl group having 6 to 32 carbon atoms. More preferably, it is a substituted or unsubstituted aryl group having 6 to 26 carbon atoms.

In the compound represented by the general formula (1), specific examples of the substituted or unsubstituted aryl group of Ar ^{1 to} Ar ³ include, for example, a phenyl group, a naphthalen-1-yl group, a naphthalen-2-yl group, Anthracen-2-yl group, anthracen-9-yl group, phenanthren-2-yl group, phenanthren-9-yl group, fluoren-9-yl group, quinolin-4-yl group, pyridin-5-yl group, pyridine -4-yl group, pyridin-3-yl group, pyridin-2-yl group, 2-benzothiophenyl group, 2-benzofuryl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzoimidazolyl 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, 2-sec-butylphenyl group, 4-tert-butylphenyl group, 3-tert-butylphenyl Group, 2-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group,

4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2'-ethylhexyl) phenyl group, 4-tert-octylphenyl group 4-n-nonylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-n-hexadecylphenyl group, 4-n-octadecylphenyl group 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 4- (4′-methylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group ,

4-ethylnaphthalen-1-yl group, 6-n-butylnaphthalen-2-yl group, 1-phenylnaphthalen-2-yl group, 9-methylanthracen-10-yl group, 9-tert-butylanthracene-10 -Yl group, 1-phenylphenanthren-2-yl group, 10-phenylphenanthren-9-yl group, 2,10-diphenylphenanthren-9-yl group, 5,10-diphenylphenanthren-9-yl group, 9, 10-diphenylphenanthren-2-yl group, 9,10-diphenylphenanthren-3-yl group, 10- (naphthalen-1′-yl) phenanthren-9-yl group, 10- (naphthalen-2′-yl) phenanthrene -9-yl group, 10- (phenanthrene-9'-yl) phenanthren-9-yl group, 10- (2'-methoxy) Ciphenyl) phenanthren-9-yl group, 10- (3′-methoxyphenyl) phenanthren-9-yl group, 10- (4′-methoxyphenyl) phenanthren-9-yl group, 10- (2′-methylphenyl) Phenanthren-9-yl group, 10- (3′-methylphenyl) phenanthren-9-yl group, 10- (4′-methylphenyl) phenanthren-9-yl group, pyren-1-yl group, pyren-2- Il group,

6-phenylpyren-1-yl group, 4-phenylnaphthalen-1-yl group, 5-phenylnaphthalen-2-yl group, 7-phenylanthracen-2-yl group, 10-phenylanthracen-9-yl group,

2,3-dimethylphenyl 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, 3,4,5-trimethylphenyl group, 2,4-diethylphenyl group, 2,3,6-trimethylphenyl group, 2,4,6-trimethylphenyl group, 2,6- Diethylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 3,5-di- tert-butylphenyl group, 2,4-dineopentylphenyl group, 2,5-di-tert-pentylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl- 2 Methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 5-indanyl group, 1,2,3,4-tetrahydro-5-naphthyl group 1,2,3,4-tetrahydro-6-naphthyl group, 4-methoxyphenyl group,

3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 2-ethoxyphenyl group, 3-n-propyloxyphenyl group, 4-isopropyloxyphenyl group, 2-isopropyloxyphenyl group, 4-n -Butyloxyphenyl group, 4-isobutyloxyphenyl group, 2-isobutyloxyphenyl group, 2-sec-butyloxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyl Oxyphenyl group, 2-neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2′-ethylbutyloxy) phenyl group, 4-n-octyloxyphenyl group, 4-n-decyloxyphenyl Group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxy Phenyl group, 4-n-hexadecyloxyphenyl group, 4-n-octadecyloxyphenyl group, 4-cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-methoxy-naphthalen-1-yl group, 4-methoxy -Naphthalen-1-yl group, 4-n-butyloxy-naphthalen-1-yl group,

5-ethoxynaphthalen-1-yl group, 6-ethoxynaphthalen-2-yl group, 6-n-butyloxynaphthalen-2-yl group, 6-n-hexyloxynaphthalen-2-yl group, 7-methoxynaphthalene 2-yl group, 7-n-butyloxynaphthalen-2-yl group, 2,3-dimethoxyphenyl 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-butyloxyphenyl group, 2-methoxy-4-methylphenyl group, 2 -Methoxy-5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxypheny Group, 3-ethyl-5-methoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-fluorophenyl group, 3 -Fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group,

2-bromophenyl group, 4-chloronaphthalen-1-yl group, 4-chloronaphthalen-2-yl group, 6-bromonaphthalen-2-yl group, 2,3-difluorophenyl group, 2,4-difluorophenyl Group, 2,5-difluorophenyl group, 2,6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2, 5-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2,3,6- Tribromophenyl group, 3,4,5-trifluorophenyl group, 2,4-dichloro-naphthalen-1-yl group, 1,6-dichloronaphth Len-2-yl group, 2-fluoro-4-methylphenyl group, 2-fluoro-5-methylphenyl group, 3-fluoro-2-methylphenyl group, 3-fluoro-4-methylphenyl group, 4-fluoro -2-methylphenyl group, 5-fluoro-2-methylphenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5-methylphenyl group,

2-chloro-6-methylphenyl group, 3-chloro-2-methylphenyl group, 4-chloro-2-methylphenyl group, 4-chloro-3-methylphenyl group, 2-chloro-4,6-dimethylphenyl Group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3-fluoro-4-ethoxyphenyl group, 5-chloro-2-methoxyphenyl group, 6-chloro-3-methoxyphenyl Group, 5-chloro-2,4-dimethoxyphenyl group, 2-chloro-4-nitrophenyl group, 4-chloro-2-nitrophenyl group, 4-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 2-trifluoromethylphenyl group, 3,5-bis (trifluoromethyl) phenyl group, 4-trifluoromethyloxyphenyl group, 4-a Ruphenyl group, 2-allylphenyl group, 2-isopropenylphenyl group, 4-benzylphenyl group, 2-benzylphenyl group, 4- (4′-methylbenzyl) phenyl group, 4-cumylphenyl group, 4- (4 ′ -Methoxycumyl) phenyl group,

4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4′-methylphenyl) phenyl group, 4- (4′-ethylphenyl) phenyl group, 4- (4′-isopropylphenyl) ) Phenyl group, 4- (4′-tert-butylphenyl) phenyl group, 4- (4′-n-hexylphenyl) phenyl group, 4- (4′-n-octylphenyl) phenyl group, 4- (4 '-Methoxyphenyl) phenyl group, 4- (4'-ethoxyphenyl) phenyl group, 4- (4'-n-butoxyphenyl) phenyl group, 2- (2'-methoxyphenyl) phenyl group, 4- (4 '-Fluorophenyl) phenyl group, 4- (4'-chlorophenyl) phenyl group, 3-methyl-4-phenyl group, 2-methoxy-5-phenylphenyl group, 3-methoxy -4-phenylphenyl group, 4-methoxymethylphenyl group, 4-ethoxymethylphenyl group, 4-n-butyloxymethylphenyl group, 3-methoxymethylphenyl group, 4- (2'-methoxyethyl) phenyl group, 4- (2′-ethoxyethyloxy) phenyl group, 4- (2′-n-butyloxyethyloxy) phenyl group,

4- (3′-ethoxypropyloxy) phenyl group, 4-vinyloxyphenyl group, 4-allyloxyphenyl group, 3-allyloxyphenyl group, 4- (4′-pentenyloxy) phenyl group, 4-allyloxy Naphthalen-1-yl group, 4-allyloxymethylphenyl group, 4- (2′-allyloxyethyloxy) phenyl group, 4-benzyloxyphenyl group, 2-benzyloxyphenyl group, 4-phenethyloxyphenyl group, 4- (4′-chlorobenzyloxy) phenyl group, 4- (4′-methylbenzyloxy) phenyl group, 4- (4′-methoxybenzyloxy) phenyl group, 4- (3′-ethoxybenzyloxy) phenyl Group, 4-benzyloxynaphthalen-1-yl group, 5- (4′-methylbenzyloxy) naphthalene- -Yl group, 6-benzyloxynaphthalen-2-yl group, 6- (4'-methylbenzyloxy) naphthalen-2-yl group, 7-benzyloxynaphthalen-2-yl group, 4- (benzyloxymethyl) Phenyl group, 4- (2′-benzyloxyethyloxy) phenyl group, 4-phenyloxyphenyl group, 3-phenyloxyphenyl group, 2-phenyloxyphenyl group,

4- (4′-methylphenyloxy) phenyl group, 4- (4′-methoxyphenyloxy) phenyl group, 4- (4′-chlorophenyloxy) phenyl group, 4-phenyloxynaphthalen-1-yl group, 6 -Phenyloxynaphthalen-2-yl group, 7-phenyloxynaphthalen-2-yl group, 4-phenyloxymethylphenyl group, 4- (2'-phenyloxyethoxy) phenyl group, 4- [2 '-(4 '-Methylphenyloxy) ethoxy] phenyl group, 4- [2'-(4'-methoxyphenyloxy) ethoxy] phenyl group, 4- [2 '-(4'-chlorophenyloxy) ethoxy] phenyl group, 4- Acetylphenyl group, 3-acetylphenyl group, 2-acetylphenyl group, 4-ethylcarbonylphenyl group, 2-ethylcarbonyl Phenyl group, 4-n-butylcarbonylphenyl group, 4-n-hexylcarbonylphenyl group, 4-n-octylcarbonylphenyl group, 4-cyclohexylcarbonylphenyl group, 4-acetylnaphthalen-1-yl group, 6-acetyl Naphthalen-2-yl group, 6-n-butylcarbonylnaphthalen-2-yl group, 4-allylcarbonylphenyl group, 4-benzylcarbonylphenyl group,

4- (4′-methylbenzyl) carbonylphenyl group, 4-phenylcarbonylphenyl group, 4- (4′-methylphenyl) carbonylphenyl group, 4- (4′-chlorophenyl) carbonylphenyl group, 4-phenylcarbonylnaphthalene -1-yl group, 4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-n-propyloxycarbonylphenyl group, 4-n-butyloxy Carbonylphenyl group, 4-n-hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonylnaphthalen-1-yl group, 6-methoxycarbonylnaphthalene-2 Yl group, 6-n-butyloxycarbonylnaphthalen-2-yl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4′-chlorobenzyl) oxycarbonylphenyl group, 4-phenethyl Oxycarbonylphenyl group, 6-benzyloxycarbonylnaphthalen-2-yl group, 4-phenyloxycarbonylphenyl group,

4- (4′-ethylphenyl) oxycarbonylphenyl group, 4- (4′-chlorophenyl) oxycarbonylphenyl group, 4- (4′-ethoxyphenyl) oxycarbonylphenyl group, 6-phenyloxycarbonylnaphthalene-2- Yl group, 4-acetyloxyphenyl group, 3-acetyloxyphenyl group, 2-acetyloxyphenyl group, 4-ethylcarbonyloxyphenyl group, 2-ethylcarbonyloxyphenyl group, 4-n-propylcarbonyloxyphenyl group, 4-n-pentylcarbonyloxyphenyl group, 4-n-octylcarbonyloxyphenyl group, 4-cyclohexylcarbonyloxyphenyl group, 3-cyclohexylcarbonyloxyphenyl group, 4-acetyloxynaphthalen-1-yl group, 4-n -Buchi Carbonyloxynaphthalen-1-yl group, 5-acetyloxynaphthalen-1-yl group, 6-ethylcarbonyloxynaphthalen-2-yl group, 7-acetyloxynaphthalen-2-yl group, 4-allylcarbonyloxyphenyl group 4-benzylcarbonyloxyphenyl group, 4-phenethylcarbonyloxyphenyl group, 6-benzylcarbonyloxy-naphthalen-2-yl group,

4-phenylcarbonyloxyphenyl group, 4- (4′-methylphenyl) carbonyloxyphenyl group, 4- (2′-methylphenyl) carbonyloxyphenyl group, 4- (4′-chlorophenyl) carbonyloxyphenyl group, 4 -(2'-chlorophenyl) carbonyloxyphenyl group, 4-phenylcarbonyloxynaphthalen-1-yl group, 6-phenylcarbonyloxynaphthalen-2-yl group, 7-phenylcarbonyloxynaphthalen-2-yl group, 4- Methylthiophenyl group, 2-methylthiophenyl group, 2-ethylthiophenyl group, 3-ethylthiophenyl group, 4-n-propylthiophenyl group, 2-isopropylthiophenyl group, 4-n-butylthiophenyl group, 2 -Isobutylthiophenyl group, 2-neopentylph Nyl group, 4-n-hexylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group, 4-benzylthiophenyl group, 3-benzylthiophenyl group, 2-benzylthiophenyl group, 4 -(4'-chlorobenzylthio) phenyl group, 4-phenylthiophenyl group, 3-phenylthiophenyl group, 2-phenylthiophenyl group,

4- (4′-methylphenylthio) phenyl group, 4- (3′-methylphenylthio) phenyl group, 4- (4′-methoxyphenylthio) phenyl group, 4- (4′-chlorophenylthio) phenyl group 2-ethylthionaphthalen-1-yl group, 4-methylthionaphthalen-1-yl group, 6-ethylthionaphthalen-2-yl group, 6-phenylthionaphthalen-2-yl group, 4-nitrophenyl group, 3-nitrophenyl group, 2-nitrophenyl group, 3,5-dinitrophenyl group, 4-nitronaphthalen-1-yl group, 4-formylphenyl group, 3-formylphenyl group, 2-formylphenyl group, 4- Formylnaphthalen-1-yl group, 1-formylnaphthalen-2-yl group, 4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morph Linophenyl group, 4- (N-ethylpiperazino) phenyl group, 4-pyrrolidinonaphthalen-1-yl group, 4-aminophenyl group, 3-aminophenyl group, 2-aminophenyl group, 4- (N-methylamino) Phenyl group, 3- (N-methylamino) phenyl group, 4- (N-ethylamino) phenyl group, 2- (N-isopropylamino) phenyl group, 4- (Nn-butylamino) phenyl group,

2- (Nn-butylamino) phenyl group, 4- (Nn-octylamino) phenyl group, 4- (Nn-dodecylamino) phenyl group, 4- (N-benzylamino) phenyl group, 4- (N-phenylamino) phenyl group, 2- (N-phenylamino) phenyl group, 4- (N, N-dimethylamino) phenyl group, 3- (N, N-dimethylamino) phenyl group, 4- (N, N-diethylamino) phenyl group, 2- (N, N-dimethylamino) phenyl group, 2- (N, N-diethylamino) phenyl group, 4- (N, N-di-n-butylamino) phenyl Group, 4- (N, N-di-n-hexylamino) phenyl group, 4- (N-cyclohexyl-N-methylamino) phenyl group, 4- (N, N-diethylamino) -naphthalen-1-yl group , 4- (N Benzyl-N-phenylamino) phenyl group, 4- (N, N-diphenylamino) phenyl group, 4- [N-phenyl-N- (4-methylphenyl) amino] phenyl group, 4- [N, N- Di (3′-methylphenyl) amino] phenyl group, 4- [N, N-di (4′-methylphenyl) amino] phenyl group, 4- [N, N-di (4′-methoxyphenyl) amino] Phenyl group,

2- (N, N-diphenylamino) phenyl group, 4- [N- (naphthalen-1-yl) -N-phenylamino] phenyl group, 4- [N- (anthracen-2-yl) -N-phenyl Amino] phenyl group, 4- [N- (9-phenanthryl) -N-phenylamino] phenyl group, 4- [N, N-di (naphthalen-1-yl) amino] phenyl group, 4- [N- ( Naphthalen-1-yl) -N- (9-phenanthryl) amino] phenyl group, 4- [N- (2-methylphenyl) -N-phenylamino] phenyl group, 4- [N- (naphthalen-2-yl) ) -N- (9-phenanthryl) amino] phenyl group, 4- [N, N-diphenylamino] -naphthalen-1-yl group,

4-hydroxyphenyl group, 3-hydroxyphenyl group, 2-hydroxyphenyl group, 4-methyl-3-hydroxyphenyl group, 6-methyl-3-hydroxyphenyl group, 2-hydroxynaphthalen-1-yl group, 8- Hydroxynaphthalen-1-yl group, 4-hydroxynaphthalen-1-yl group, 1-hydroxynaphthalen-2-yl group, 6-hydroxynaphthalen-2-yl group, 4-cyanophenyl group, 2-cyanophenyl group, 4-cyanonaphthalen-1-yl group, 6-cyanonaphthalen-2-yl group,

Fluoren-2-yl group, 9-methylfluoren-2-yl group, 9,9-dimethylfluoren-2-yl group, 9-ethylfluoren-2-yl group, 9,9-diethylfluoren-2-yl group 9-isopropylfluoren-2-yl group, 9,9-diisopropylfluoren-2-yl group, 9-tert-butylfluoren-2-yl group, 9,9-di-tert-butylfluoren-2-yl group 9-cyclohexylfluoren-2-yl group, 9,9-dicyclohexylfluoren-2-yl group, 9-phenylfluoren-2-yl group, 9,9-diphenylfluorenfluoren-2-yl group, 9- (naphthalene) -1′-yl) fluoren-2-yl group, 9,9-di (naphthalen-1′-yl) fluoren-2-yl group,

4-phenylfluoren-2-yl group, 9-methyl-4-phenylfluoren-2-yl group, 9,9-dimethyl-4-phenylfluoren-2-yl group, 9-ethyl-4-phenylfluorene-2 -Yl group, 9,9-diethyl-4-phenylfluoren-2-yl group, 9-isopropyl-4-phenylfluoren-2-yl group, 9,9-diisopropyl-4-phenylfluoren-2-yl group, 9-tert-butyl-4-phenylfluoren-2-yl group, 9,9-di-tert-butyl-4-phenylfluoren-2-yl group, 9-cyclohexyl-4-phenylfluoren-2-yl group, 9,9-dicyclohexyl-4-phenylfluoren-2-yl group, 4,9-diphenylfluoren-2-yl group, 4,9,9-triphenylfluorenefluor Ren-2-yl group, 4-phenyl-9- (naphthalen-1'-yl) fluoren-2-yl group, 4-phenyl-9,9-di (naphthalen-1'-yl) fluoren-2-yl Group,

7-tert-butylfluoren-2-yl group, 7-tert-butyl-9-methylfluoren-2-yl group, 7-tert-butyl-9,9-dimethylfluoren-2-yl group, 7-tert- Butyl-9-ethylfluoren-2-yl group, 7-tert-butyl-9,9-diethylfluoren-2-yl group, 7-tert-butyl-9-isopropylfluoren-2-yl group, 7-tert- Butyl-9,9-diisopropylfluoren-2-yl group, 7,9-di-tert-butylfluoren-2-yl group, 7,9,9-tri-tert-butylfluoren-2-yl group, 7- tert-butyl-9-cyclohexylfluoren-2-yl group, 7-tert-butyl-9,9-dicyclohexylfluoren-2-yl group, 7-tert-butyl-9-phenylfluoren-2-yl group, 7- tert-butyl-9 , 9-diphenylfluorenefluoren-2-yl group, 7-tert-butyl-9- (naphthalen-1′-yl) fluoren-2-yl group, 7-tert-butyl-9,9-di (naphthalene-1) '-Yl) fluoren-2-yl group,

7-phenylfluoren-2-yl group, 7-phenyl-9-methylfluoren-2-yl group, 7-phenyl-9,9-dimethylfluoren-2-yl group, 7-phenyl-9-ethylfluorene-2 -Yl group, 7-phenyl-9,9-diethylfluoren-2-yl group, 7-phenyl-9-isopropylfluoren-2-yl group, 7-phenyl-9,9-diisopropylfluoren-2-yl group, 7-phenyl-9-tert-butylfluoren-2-yl group, 7-phenyl-9,9-di-tert-butylfluoren-2-yl group, 7-phenyl-9-cyclohexylfluoren-2-yl group, 7-phenyl-9,9-dicyclohexylfluoren-2-yl group, 7,9-diphenylfluoren-2-yl group, 7,9,9-triphenylfluorenefluor Ren-2-yl group, 7-phenyl-9- (naphthalen-1′-yl) fluoren-2-yl group, 7-phenyl-9,9-di (naphthalen-1′-yl) fluoren-2-yl Group,

  4-methoxyfluoren-2-yl group, 4-methoxy-9-methylfluoren-2-yl group, 4-methoxy-9,9-dimethylfluoren-2-yl group, 5-methoxyfluoren-2-yl group, 5-methoxy-9-methylfluoren-2-yl group, 5-methoxy-9,9-dimethylfluoren-2-yl group, 7-methoxyfluoren-2-yl group, 7-methoxy-9-methylfluorene-2 -Yl group, 7-methoxy-9,9-dimethylfluoren-2-yl group, 4-cyanofluoren-2-yl group, 4-cyano-9-methylfluoren-2-yl group, 4-cyano-9, 9-dimethylfluoren-2-yl group, 4-fluorofluoren-2-yl group, 4-fluoro-9-methylfluoren-2-yl group, 4-fluoro-9,9-dimethylfluorine N-2-yl group, 7-trifluoromethylfluoren-2-yl group, 7-trifluoromethyl-9-methylfluoren-2-yl group, 7-trifluoromethyl-9,9-dimethylfluorene-2- Yl group, 4-trifluoromethylfluoren-2-yl group, 4-trifluoromethyl-9-methylfluoren-2-yl group, 4-trifluoromethyl-9,9-dimethylfluoren-2-yl group, etc. And substituted or unsubstituted aryl groups.

As a preferred form of the triarylamine compound represented by the general formula (1), a triarylamine compound in which Ar ¹ or Ar ² is a phenanthryl group substituted with an aryl group, or Ar ¹ and Ar ² are substituted or unsubstituted A triarylamine compound which is a substituted or unsubstituted aryl group which is not a phenanthryl group.

In the compound represented by the general formula (1), when Ar ¹ or Ar ² is a phenanthryl group substituted with an aryl group, Ar ¹ and Ar ² are preferably each independently having a carbon number of 38 or less. A phenanthren-2-yl group substituted at the 1-position with a substituted or unsubstituted aryl group, a phenanthren-2-yl group substituted at the 9-position and the 10-position with a substituted or unsubstituted aryl group having 38 or less carbon atoms, Phenanthrene-3-yl substituted at 9th and 10th positions with a substituted or unsubstituted aryl group having 38 or less carbon atoms, Phenanthrene-substituted at 10th position with a substituted or unsubstituted aryl group having 38 or less carbon atoms 9-yl group, phenanthren-9-yl group substituted with 5- or 10-position with a substituted or unsubstituted aryl group having 38 or less carbon atoms or carbon number A phenanthren-9-yl group substituted at the 2-position and the 10-position with 38 or less substituted or unsubstituted aryl groups, and more preferably at the 9-position and 10-position with a substituted or unsubstituted aryl group having 32 or less carbon atoms. Substituted phenanthren-2-yl group, substituted or unsubstituted aryl group having 32 or less carbon atoms, substituted phenanthren-3-yl group substituted at 9 and 10 positions with substituted or unsubstituted aryl group, substituted or unsubstituted 32 or less carbon atoms A phenanthren-9-yl group substituted at the 10-position with an aryl group, and more preferably a phenanthren-2-yl substituted at the 9-position and the 10-position with a substituted or unsubstituted aryl group having 26 or less carbon atoms A phenanthren-3-yl group substituted at the 9-position and the 12-position with a substituted or unsubstituted aryl group having 26 or less carbon atoms, 10 position with an unsubstituted aryl group is phenanthrenes-9-yl group substituted.

In the compound represented by the general formula (1) according to the present invention, when Ar ¹ or Ar ² is a phenanthryl group substituted with an aryl group, specific examples of Ar ¹ or Ar ² include 1-phenylphenanthrene- 2-yl group, 10-phenylphenanthren-9-yl group, 2,10-diphenylphenanthren-9-yl group, 5,10-diphenylphenanthren-9-yl group, 9,10-diphenylphenanthren-2-yl group 9,10-diphenylphenanthren-3-yl group, 10- (naphthalen-1′-yl) phenanthren-9-yl group, 10- (naphthalen-2′-yl) phenanthren-9-yl group, 10- ( Phenanthrene-9′-yl) phenanthren-9-yl group, 10- (2′-methoxyphenyl) phenanthrene-9-i A group, 10- (3′-methoxyphenyl) phenanthren-9-yl group, 10- (4′-methoxyphenyl) phenanthren-9-yl group, 10- (2′-methylphenyl) phenanthren-9-yl group, A 10- (3′-methylphenyl) phenanthren-9-yl group and a 10- (4′-methylphenyl) phenanthren-9-yl group can be exemplified.

In the compound represented by the general formula (1), when Ar ¹ and Ar ² are substituted or unsubstituted aryl groups that are not substituted or unsubstituted phenanthryl groups, Ar ¹ and Ar ² are preferably Independently, it is a substituted or unsubstituted aryl group having 5 to 38 carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 32 carbon atoms, and further preferably a substituted group having 6 to 26 carbon atoms. Or it is an unsubstituted aryl group. However, in this case, a substituted or unsubstituted phenanthryl group is excluded.

In the compound represented by the general formula (1) according to the present invention, when Ar ¹ and Ar ² are a substituted or unsubstituted aryl group that is not a substituted or unsubstituted phenanthryl group, the substitution of Ar ^{1 to} Ar ³ or Specific examples of the unsubstituted aryl group include the substituted or unsubstituted aryl groups listed as the aforementioned Ar ^{1 to} Ar ³ . However, in this case, a substituted or unsubstituted phenanthryl group is excluded.

Z ^{1 to} Z ⁸ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted An aryl group or a substituted or unsubstituted aralkyl group is represented, and the adjacent groups of Z ^{1 to} Z ⁸ may form a ring together with the adjacent groups.

  The aryl group represents a carbocyclic aromatic compound and a heterocyclic aromatic group. The aryl group of the aralkyl group similarly includes a carbocyclic aromatic compound and a heterocyclic aromatic group.

In the compound represented by the general formula (1), Z ^{1 to} Z ⁸ are preferably each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, A linear, branched or cyclic alkoxy group having 1 to 10 carbon atoms, an unsubstituted amino group, an amino group substituted with a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, Amino group substituted with 20 substituted or unsubstituted aryl groups, or an amino group substituted with a substituted or unsubstituted aralkyl group having 6 to 21 carbon atoms, or a substituted or unsubstituted aryl group with 5 to 25 carbon atoms Or a substituted or unsubstituted aralkyl group having 6 to 16 carbon atoms,

  More preferably, a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, or a 6 to 12 carbon atom. An amino group substituted with a substituted or unsubstituted aryl group, an amino group substituted with a substituted or unsubstituted aralkyl group having 7 to 19 carbon atoms, a substituted or unsubstituted aryl group with 6 to 18 carbon atoms, or A substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms,

  More preferably, a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 4 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 4 carbon atoms, and a C 6 to 10 carbon atom. An amino group substituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms.

In the compound represented by the general formula (1), examples of the halogen atom represented by Z ^{1 to} Z ⁸ include a fluorine atom, a chlorine atom, and a bromine atom.

In the compound represented by the general formula (1), specific examples of the linear, branched or cyclic alkyl group of Z ^{1 to} Z ⁸ include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2 -Pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2 -Dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, 1-ethyloctyl group, n-undecyl group, 1-methyl Sil group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonyl group N-octadecyl group, 1-nonyldecyl group,

1-decylundecyl group, n-eicosyl group, n-docosyl group, n-tetracosyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, 2-cyclohexylethyl group, bornel group, isobornyl group, 1-norbornyl group, 2-norbornanemethyl group, 1-bicyclo [2.2.2] octyl group, 1-adamantyl group, 3-noradamantyl group, 1-adamantylmethyl group, cyclobutyl group, cyclopentyl group, 1-methylcyclopentyl group, cyclohexyl group 4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group 3,5-di Tylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 3,3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4-tert-butylcyclohexyl group, 3-tert-butylcyclohexyl group, 4- A phenylcyclohexyl group, a 2-phenylcyclohexyl group,

Cycloheptyl group, cyclooctyl group, cyclodecyl group, cyclododecyl group, cyclotetradecyl group, methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group N-octyloxymethyl group, n-decyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-n-propyloxyethyl group, 2-isopropyloxyethyl group, 2-n-butyloxyethyl group Group, 2-n-pentyloxyethyl group, 2-n-hexyloxyethyl group, 2- (2′-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group 2- (2′-ethylhexyloxy) ethyl group, 2-n-decyloxyethyl group, 2-n-dodecyl Kishiechiru group, 2-n-tetradecyloxy ethyl, 2-cyclohexyloxy ethyl, 2-methoxypropyl, 3-methoxypropyl group,

3-ethoxypropyl group, 3-n-propyloxypropyl group, 3-isopropyloxypropyl group, 3- (n-butyloxy) propyl group, 3- (n-pentyloxy) propyl group, 3- (n-hexyloxy) ) Propyl group, 3- (2′-ethylbutyloxy) propyl group, 3- (n-octyloxy) propyl group, 3- (2′-ethylhexyloxy) propyl group, 3- (n-decyloxy) propyl group, 3- (n-dodecyloxy) propyl group, 3- (n-tetradecyloxy) propyl group, 3-cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4-n-propyloxybutyl group 4-isopropyloxybutyl group, 4-n-butyloxybutyl group, 4-n-hexyloxybutyl group, 4-n-octyl Ruokishibuchiru group, 4-n-decyloxy-butyl group, 4-n-dodecyloxy-butyl group, 5-methoxypentyl group, 5-ethoxypentyl group,

5-n-propyloxypentyl group, 6-ethoxyhexyl group, 6-isopropyloxyhexyl group, 6-n-butyloxyhexyl group, 6-n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4 -Methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropyloxyheptyl group, 8-methoxyoctyl group, 10-methoxydecyl group, 10-n-butyloxydecyl group, 12-ethoxydodecyl group, 12-isopropyloxide decyl Group, tetrahydrofurfuryl group, 2- (2′-methoxyethoxy) ethyl group, 2- (2′-ethoxyethoxy) ethyl group, 2- (2′-n-butyloxyethoxy) ethyl group, 3- (2 '-Ethoxyethoxy) propyl group, 2-allyloxyethyl group, 2- (4'-pentenyl) ) Ethyl group, 3- allyloxy propyl, 3- (2'-hexenyl) propyl group, 3- (2'-heptenyloxy) propyl group,

3- (1′-cyclohexenyloxy) propyl group, 4-allyloxybutyl group, benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2- (4′-methylbenzyloxy) ethyl Group, 2- (2′-methylbenzyloxy) ethyl group, 2- (4′-fluorobenzyloxy) ethyl group, 2- (4′-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4′-methoxybenzyloxy) propyl group, 4-benzyloxybutyl group, 2- (benzyloxymethoxy) ethyl group, 2- (4′-methylbenzyloxymethoxy) ethyl group, phenyloxymethyl group, 4-methyl Phenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group, 4-metho Shi phenyloxymethyl group, 4-fluorophenyl oxymethyl group, 4-chlorophenyl oxymethyl group, 2-chlorophenyl oxymethyl group,

2-phenyloxyethyl group, 2- (4′-methylphenyloxy) ethyl group, 2- (4′-ethylphenyloxy) ethyl group, 2- (4′-methoxyphenyloxy) ethyl group, 2- (4 '-Chlorophenyloxy) ethyl group, 2- (4'-bromophenyloxy) ethyl group, 2- (1'-naphthyloxy) ethyl group, 2- (2'-naphthyloxy) ethyl group, 3-phenyloxypropyl Group, 3- (2′-naphthyloxy) propyl group, 4-phenyloxybutyl group, 4- (2′-ethylphenyloxy) butyl group, 5- (4′-tert-butylphenyloxy) pentyl group, 6 -(2'-chlorophenyloxy) hexyl group, 8-phenyloxyoctyl group, 10-phenyloxydecyl group, 10- (3'-chlorophenyloxy) decyl Group, 2- (2'-phenyloxyethoxy) ethyl group, 3- (2'-phenyloxyethoxy) propyl group, 4- (2'-phenyloxyethoxy) butyl group,

n-butylthiomethyl group, n-hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-butylthioethyl group, 2-n-hexylthioethyl group, 2-n-octyl Thioethyl group, 2-n-decylthioethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-n-butylthiopropyl group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group 4-n-butylthiobutyl group, 5-ethylthiopentyl group, 6-methylthiohexyl group, 6-ethylthiohexyl group, 6-n-butylthiohexyl group, 8-methylthiooctyl group, 2- (2 ′ -Methoxyethylthio) ethyl group, 4- (3'-ethoxypropylthio) butyl group, 2- (2'-ethylthioethylthio) ethyl group, 2-allylthioethyl group, - benzyl thioethyl group, 3- (4'-methylbenzyl-thio) propyl group, 4-benzyl-thio-butyl group,

2- (2′-benzyloxyethylthio) ethyl group, 3- (3′-benzylthiopropylthio) propyl group, 2-phenylthioethyl group, 2- (4′-methoxyphenylthio) ethyl group, 2- (2′-phenyloxyethylthio) ethyl group, 3- (2′-phenylthioethylthio) propyl group, fluoromethyl group, 3-fluoropropyl group, 6-fluorohexyl group, 8-fluorooctyl group, trifluoro Methyl group, 1,1-dihydro-perfluoroethyl group, 1,1-dihydro-perfluoro-n-propyl group, 1,1,3-trihydro-perfluoro-n-propyl group, 1,1-dihydro- Perfluoro-n-butyl group, 1,1-dihydro-perfluoro-n-pentyl group, 1,1-dihydro-perfluoro-n-hexyl group, Orohekishiru group, 4-fluoro-cyclohexyl group,

1,1-dihydro-perfluoro-n-octyl group, 1,1-dihydro-perfluoro-n-decyl group, 1,1-dihydro-perfluoro-n-dodecyl group, 1,1-dihydro-perfluoro group -N-tetradecyl group, 1,1-dihydro-perfluoro-n-hexadecyl group, perfluoro-n-hexyl group, dichloromethyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7 -Chloroheptyl group, 8-chlorooctyl group, 2,2,2-trichloroethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group , 6-hydroxyhexyl group, 5-hydroxyheptyl group, 8-hydroxyoctyl group, 10-hydroxydecyl group 12-hydroxy-dodecyl group, 2-hydroxy-linear, such as a cyclohexyl group, and a branched-chain or cyclic alkyl group.

In the compound represented by the general formula (1), linear Z ¹ to Z ^8, Specific examples of the branched chain or cyclic alkoxy group, for example, straight chain Z ¹ to Z ^8, branched chain or cyclic Specific examples of the alkyl group include straight-chain, branched-chain, or cyclic alkoxy groups represented by a form in which an oxygen atom is bonded to a straight-chain, branched-chain, or cyclic alkyl group.

When Z ^{1 to} Z ⁸ are amino groups, the amino group may have a substituent, and an alkyl group having 1 to 20 carbon atoms, an aryl group having 5 to 20 carbon atoms, or 6 to 21 carbon atoms. May be mono- or di-substituted with a substituent such as an aralkyl group.

In the compound represented by the general formula (1), examples of the substituted or unsubstituted amino group represented by Z ^{1 to} Z ⁸ include an amino group, an N-methylamino group, an N-ethylamino group, and an Nn-propyl group. Amino group, N-isopropylamino group, Nn-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, Nn-pentylamino group, N-cyclopentyl Amino group, Nn-hexylamino group, N-cyclohexylamino group, N-benzylamino group, N-phenethylamino group,

N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino group, N, N-di-isopropylamino group, N, N-di-n-butylamino group, N , N-di-isobutylamino group, N, N-di-sec-butylamino group, N, N-di-n-pentylamino group, N, N-dicyclopentylamino group, N, N-dicyclohexylamino group, N, N-dibenzylamino group, N, N-diphenethylamino group, N-methyl-N-ethylamino group, N-methyl-Nn-propylamino group, N-methyl-N-isopropylamino group, N-methyl-Nn-butylamino group, N-methyl-N-tert-butylamino group, N-methyl-N-cyclopentylamino group, N-methyl-N-cyclohexylamino group, N-methyl-N- Benzylamino group

N-methyl-N-phenethylamino group, N-ethyl-N-tert-butylamino group, N-ethyl-N-cyclohexylamino group, N-ethyl-N-benzylamino group, N-isopropyl-N-cyclopentylamino Group, N-isopropyl-N-cyclohexylamino group, N-isopropyl-N-benzylamino group, N-tert-butyl-N-cyclohexylamino group, N-tert-butyl-N-benzylamino group, N-cyclopentyl- N-benzylamino group, N-cyclohexyl-N-benzylamino group,

N-phenylamino group, N- (naphthalen-1-yl) amino group, N- (naphthalen-2-yl) amino group, N- (anthracen-2-yl) amino group, N- (anthracen-9-yl) ) Amino group, N- (pyren-1-yl) amino group, N- (pyren-2-yl) amino group, N- (phenanthren-9-yl) amino group, N- (phenanthren-2-yl) group N- (4-phenylphenyl) amino group, N- (3-phenylphenyl) amino group, N- (2-phenylphenyl) amino group,

N- (4-methylphenyl) amino group, N- (3-methylphenyl) amino group, N- (2-methylphenyl) amino group, N- (4-methoxyphenyl) amino group, N- (3-methoxy Phenyl) amino group, N- (2-methoxyphenyl) amino group, N- (4-fluorophenyl) amino group, N- (3-fluorophenyl) amino group, N- (2-fluorophenyl) amino group,

N, N-diphenylamino group, N, N-di (naphthalen-1-yl) amino group, N, N-di (naphthalen-2-yl) amino group, N, N-di (4-phenylphenyl) amino Group, N, N- (4-methylphenyl) amino group, N, N-di (3-methylphenyl) amino group, N-phenyl-N- (naphthalen-1-yl) amino group, N-phenyl-N -(Naphthalen-2-yl) amino group, N-phenyl-N- (4-phenylphenyl) amino group, N- (phenanthrene-9-yl) -N-phenylamino group, N- (phenanthren-2-yl) ) -N-phenylamino group, N- (naphthalen-1-yl) -N- (naphthalen-2-yl) amino group, N- (anthracen-2-yl) -N-phenylamino group, N- (anthracene) -9-yl) -N Phenylamino group, N-phenyl-N- (pyren-1-yl) amino group, N- (anthracen-2-yl) -N- (naphthalen-1-yl) amino group, N- (anthracen-9-yl) ) -N- (naphthalen-1-yl) amino group, N-carbazolyl group, 3-tert-butyl-N-carbazolyl group.

In the compound represented by the general formula (1), specific examples of the substituted or unsubstituted aryl group of Z ^{1 to} Z ⁸ include specific examples of the substituted or unsubstituted aryl group of Ar ^{1 to} Ar ³ described above. Mention may be made of the substituted or unsubstituted aryl groups mentioned.

In the compound represented by the general formula (1), specific examples of the substituted or unsubstituted aralkyl group of Z ^{1 to} Z ⁸ include, for example, benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group. , Α-methylphenethyl group, β-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethylphenethyl group, 4-methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methyl Benzyl group, 4-ethylbenzyl group, 2-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 2-tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group 4-n-octylbenzyl group, 4-tert-octylbenzyl group, 4-allylbenzyl group, 4-benzylbenzyl group, 4-phene Rubenzyl group, 4-phenylbenzyl group, 4- (4′-methylphenyl) benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxybenzyl group, 4-n-butoxybenzyl group, 4-n -Heptyloxybenzyl group, 4-n-decyloxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutyloxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4-phenethyloxybenzyl group, 4-phenyloxybenzyl group, 3-phenyloxybenzyl group 4-hydroxybenzyl group, 3-hydroxybenzyl group, 2-hydroxy Benzyl group, 4-hydroxy-3-methoxybenzyl group, 4-fluorobenzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group And a substituted or unsubstituted aralkyl group such as a diphenylmethyl group.

  Among the triarylamine compounds represented by the general formula (1) according to the present invention, the compound having a relatively high heat resistance, for example, a compound having a glass transition point (Tg) of 130 ° C. to 300 ° C. Exists. Such a compound is suitable as a material used for an organic electroluminescent element, for example.

  When the triarylamine compound represented by the general formula (1) according to the present invention is used as a material for the organic electroluminescent device, Tg is preferably 130 ° C to 300 ° C, and preferably 135 ° C to 300 ° C. More preferably, it is 140 to 250 degreeC.

  Specific examples of the triarylamine compound represented by the general formula (1) according to the present invention include compounds shown in the following Tables 1 to 15 (Tables 1 to 15). However, the present invention is not limited to these.

The triarylamine compound represented by the general formula (1) of the present invention can be produced by, for example, the following process (Chemical Formula 3).

[Wherein, Ar ^{1 to} Ar ³ and Z ^{1 to} Z ⁸ represent the same meaning as in the general formula (1), and X represents a halogen atom. ]

  That is, a halogenophenanthrene derivative represented by the general formula (A) and an arylamine derivative represented by the general formula (B) are converted into a palladium catalyst [eg, palladium acetate / tri-tert-butylphosphine, palladium acetate / triphenylphosphine. , Tris (dibenzylideneacetone) dipalladium / tri-tert-butylphosphine] and a base (for example, sodium-tert-butoxide, potassium carbonate, cesium carbonate, potassium-tert-butoxide). be able to. Alternatively, it is produced by reacting in the presence of a copper compound [eg, copper powder, copper chloride, copper iodide] and a base (eg, sodium tert-butoxide, potassium carbonate, cesium carbonate, potassium tert-butoxide). be able to.

  In addition, the compound represented by general formula (A) can be manufactured by the following processes (chemical formula 4), for example.

[Wherein, Ar ^{1 to} Ar ³ and Z ^{1 to} Z ⁸ represent the same meaning as in the general formula (1), H represents a hydrogen atom, and X represents a halogen atom. ]

  That is, a halogenophenanthrene derivative represented by the general formula (C) and an arylboric acid derivative represented by the general formula (D) are converted into a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium. And an arylphenanthrene derivative represented by the general formula (E) can be produced by the reaction in the presence of a base (for example, potassium carbonate, sodium carbonate, triethylamine, pyridine). Thereafter, a halogenating agent [for example, bromine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide] is allowed to act on the arylphenanthrene derivative represented by the general formula (E) in the general formula (A) The represented halogenophenanthrene derivatives can be produced.

  Next, the organic electroluminescent element of the present invention will be described. An organic electroluminescent element is usually formed by sandwiching at least one light emitting layer containing at least one light emitting component between a pair of electrodes. A hole injection / transport layer and / or an electron injection containing a hole injection component as desired, considering the functional level of the hole injection and hole transport, electron injection and electron transport of the compound used in the light emitting layer. An electron injecting and transporting layer containing a transporting component can also be provided.

  The organic electroluminescent element of the present invention comprises at least one layer containing at least one triarylamine compound represented by the general formula (1) between a pair of electrodes. In the organic electroluminescent element of the present invention, the layer containing the triarylamine compound represented by the general formula (1) is preferably a light emitting layer or a charge injection transport layer. In the organic electroluminescent device of the present invention, the charge injection transport layer represents a hole injection transport layer and an electron injection transport layer.

  For example, when the hole injection function, the hole transport function and / or the electron injection function, and the electron transport function of the compound used in the light emitting layer are good, the light emitting layer is a hole injection transport layer and / or an electron injection transport layer. As a type of element configuration that also serves as a single layer type element configuration. Further, when the light emitting layer is poor in the hole injection function and / or the hole transport function, a two-layer device configuration in which a hole injection transport layer is provided on the anode side of the light emitting layer, the light emitting layer has an electron injection function and / or Alternatively, when the electron transport function is poor, a two-layer device structure in which an electron injection transport layer is provided on the cathode side of the light emitting layer can be obtained. Furthermore, a three-layer device structure in which the light-emitting layer is sandwiched between a hole injecting and transporting layer and an electron injecting and transporting layer can be used.

  In addition, each of the hole injecting and transporting layer, the electron injecting and transporting layer, and the light emitting layer may have a single layer structure or a multilayer structure, and the hole injecting and transporting layer and the electron injecting and transporting layer The layer having an injection function and the layer having a transport function can be separately provided.

  In the organic electroluminescent device of the present invention, the triarylamine compound represented by the general formula (1) is preferably used as a component of the hole injection transport layer and / or the light emitting layer, and used as a component of the light emitting layer. More preferably.

  In the organic electroluminescent element of the present invention, the triarylamine compound represented by the general formula (1) may be used alone or in combination.

  The configuration of the organic electroluminescent device of the present invention is not particularly limited. For example, (EL-1) anode / hole injection transport layer / light emitting layer / electron injection transport layer / cathode type device (FIG. 1). ), (EL-2) anode / hole injection transport layer / light emitting layer / cathode type device (FIG. 2), (EL-3) anode / light emitting layer / electron injection transport layer / cathode type device (FIG. 3), EL-4) Anode / light emitting layer / cathode type element (FIG. 4), and the like. Further, an EL (EL-5) anode / hole injecting / transporting layer / electron injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element (FIG. 5) in which the light emitting layer is sandwiched between electron injecting and transporting layers. You can also. The (EL-4) type element structure includes an element of a type in which a light emitting component is sandwiched between a pair of electrodes as a light emitting layer, (EL-6) a hole injection transport component as a light emitting layer, A device of a type in which a light emitting component and an electron injection component are mixed and sandwiched between a pair of electrodes (FIG. 6), (EL-7) a layer in which a hole injection transport component and a light emitting component are mixed as a light emitting layer Type element sandwiched between a pair of electrodes in a form (FIG. 7), (EL-8) type element sandwiched between a pair of electrodes in a single layer form in which a light emitting component and an electron injection component are mixed as a light emitting layer Any of (FIG. 8) may be sufficient.

  The organic electroluminescent device of the present invention is not limited to these device configurations, and each type of device can be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers. Further, in each type of device, the hole injection / transport layer is disposed between the light emitting layer, the hole injection / transport component and the light emitting component mixed layer and / or the light emitting layer and the electron injection / transport layer between the light emitting component And a mixed layer of electron injecting and transporting components can be provided.

  A preferred organic electroluminescent element is an (EL-1) type element, an (EL-2) type element, an (EL-5) type element, an (EL-6) type element or an (EL-7) type element. More preferably, it is an (EL-1) type element, an (EL-2) type element or an (EL-7) type element.

  Hereinafter, the components of the organic electroluminescence device of the present invention will be described in detail. As an example, (EL-1) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode type device shown in FIG. 1 will be described.

  In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injecting and transporting layer, 4 is a light emitting layer, 5 is an electron injecting and transporting layer, 6 is a cathode, and 7 is a power source.

  The organic electroluminescent element of the present invention is preferably supported by the substrate 1, and the substrate is not particularly limited, but a transparent or translucent substrate is preferable, and the material is soda lime glass, Examples thereof include glass such as borosilicate glass and transparent polymers such as polyester, polycarbonate, polysulfone, polyethersulfone, polyacrylate, polymethyl methacrylate, polypropylene, and polyethylene. Further, a substrate made of a translucent plastic sheet, quartz, transparent ceramics, or a composite sheet in which these are combined can also be used. Furthermore, for example, a color filter film, a color conversion film, and a dielectric reflection film can be combined with the substrate to control the emission color.

As the anode 2, it is preferable to use a metal, alloy or conductive compound having a relatively large work function as an electrode material. Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In ₂ O ₃ ), tin oxide (SnO ₂ ), zinc oxide, ITO ( Indium tin oxide (Indium Tin Oxide), polythiophene, polypyrrole, etc. can be mentioned. These electrode materials may be used alone or in combination.
For the anode, these electrode materials can be formed on the substrate by a method such as vapor deposition or sputtering.

Further, the anode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the anode is preferably set to several hundred Ω or less, more preferably about 5 to 50 Ω.
The thickness of the anode is generally about 5 to 1000 nm, more preferably about 10 to 500 nm, although it depends on the material of the electrode material used.

  The hole injection transport layer 3 is a layer containing a compound having a function of facilitating the injection of holes from the anode and a function of transporting the injected holes.

The hole injecting and transporting layer may be a triarylamine compound represented by the general formula (1), or other compounds having a hole injecting and transporting function (for example, phthalocyanine derivatives, triarylamine derivatives, triarylmethane derivatives, oxazole derivatives). , Hydrazone derivatives, stilbene derivatives, pyrazoline derivatives, polysilane derivatives, polyphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, poly-N-vinylcarbazole, etc.).
The compounds having a hole injecting and transporting function may be used alone or in combination.

  The organic electroluminescent element of the present invention preferably contains a triarylamine compound represented by the general formula (1) in the hole injecting and transporting layer. It can be used in the organic electroluminescent device of the present invention. Examples of the compound having a hole injecting and transporting function other than the triarylamine compound represented by the general formula (1) of the present invention include triarylamine derivatives such as 4,4′-bis [N-phenyl-N- ( 4 "-methylphenyl) amino] -1,1'-biphenyl, 4,4'-bis [N-phenyl-N- (3" -methylphenyl) amino] -1,1'-biphenyl, 4,4 ' -Bis [N-phenyl-N- (3 "-methoxyphenyl) amino] -1,1'-biphenyl, 4,4'-bis [N-phenyl-N- (1" -naphthyl) amino] -1, 1'-biphenyl, 3,3'-dimethyl-4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] -1,1'-biphenyl, 1,1-bis [4 ' -[N, N-di (4 "-methylphenyl) amino] fur Nyl] cyclohexane, 9,10-bis [N- (4′-methylphenyl) -N- (4 ″ -n-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6 -Phenylphenanthridine,

4-methyl-N, N-bis [4 ", 4" '-bis [N', N'-di (4-methylphenyl) amino] biphenyl-4'-yl] aniline, N, N'-bis [ 4- (Diphenylamino) phenyl] -N, N′-diphenyl-1,3-diaminobenzene, N, N′-bis [4- (diphenylamino) phenyl] -N, N′-diphenyl-1,4- Diaminobenzene, 5,5 ″ -bis [4- (bis [4-methylphenyl] amino) phenyl-2,2 ′: 5 ′, 2 ″ -terthiophene, 1,3,5-tris (diphenylamino) benzene 4,4 ', 4 "-tris (N-carbazolyl) triphenylamine, 4,4', 4" -tris [N, N-bis (4 "'-tert-butylbiphenyl-4" "-yl) Amino] triphenylamine, 1,3,5-tri More preferred are polythiophene and its derivatives, poly-N-vinylcarbazole and its derivatives, such as su [(4'-diphenylaminophenyl] benzene.

  When the triarylamine compound represented by the general formula (1) and another compound having a hole injection function are used in combination, the triarylamine compound represented by the general formula (1) in the hole injection transport layer The content is preferably 0.1% by weight or more, more preferably 0.5 to 99.9% by weight, and still more preferably 3 to 97% by weight.

  The light emitting layer 4 is a layer containing a compound having a function of injecting holes and electrons, a function of transporting them, and a function of generating excitons by recombination of holes and electrons.

  The light emitting layer uses the triarylamine compound represented by the general formula (1) as a host material, and uses at least one compound having a light emitting function other than the triarylamine compound represented by the general formula (1) as a guest material. The triarylamine compound represented by the general formula (1) can be formed using at least one compound having a light emitting function other than the triarylamine compound represented by the general formula (1) as a host material. Can be used as a guest material.

  As a compound (guest material / host material) having a light emitting function other than the triarylamine compound represented by the general formula (1), for example, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [ For example, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4- Bis (9′-ethynylanthcenyl) benzene, 4,4′-bis (9 ″ -ethynylanthracenyl) biphenyl, dibenzo [f, f] diindeno [1,2,3-cd: 1 ′, 2 ′ , 3'-lm] perylene derivatives], triarylamine derivatives (eg hole injection transport) Examples of the compound having a function include the compounds described above), organometallic complexes [for example, tris (8-quinolinolato) aluminum,

Bis (10-benzo [h] quinolinolato) beryllium, zinc salt of 2- (2′-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine, zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone , Aluminum salt of 5-hydroxyflavone], stilbene derivatives [for example, 1,1,4,4-tetraphenyl-1,3-butadiene, 4,4′-bis (2,2-diphenylvinyl) biphenyl, 4, 4′-bis [(1,1,2-triphenyl) ethenyl] biphenyl], coumarin derivatives (eg, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138, coumarin 151, coumarin 152, coumarin. 153, Coumarin 307, Coumarin 311, Coumarin 314, Coumarin 34, coumarin 338, coumarin 343, coumarin 500), pyran derivatives (eg DCM1, DCM2), oxazone derivatives (eg Nile Red), benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamic acid esters Derivatives, poly-N-vinylcarbazole and derivatives thereof,

  Polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polybiphenylene vinylene and derivatives thereof, polyterphenylene vinylene and derivatives thereof, polynaphthylene vinylene and derivatives thereof, polythienylene vinylene and Examples thereof include derivatives thereof. Compounds having a light emitting function other than the triarylamine compound represented by the general formula (1) (guest material / host material) include acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallic complexes. And stilbene derivatives are preferred, and polycyclic aromatic compounds and organometallic complexes are more preferred.

  The organic electroluminescent element of the present invention preferably contains a triarylamine compound represented by the general formula (1) as a host material in the light emitting layer.

When the triarylamine compound represented by the general formula (1) is used as a host material in combination with another compound having a light emitting function (guest material), the triaryl represented by the general formula (1) in the light emitting layer The content of the amine compound is preferably 99.9 to 80% by weight, and more preferably 99 to 90% by weight.
A host material may be used independently and may be used together.

Moreover, a guest material may be used independently and may be used together.
When a plurality of host materials are used in combination, the ratio of the triarylamine compound represented by the general formula (1) of the present invention to the entire host material is preferably 99 to 10% by weight, more preferably 90 to 20%. % By weight.

  The electron injection / transport layer 5 is a layer containing a compound having a function of facilitating injection of electrons from the cathode and / or a function of transporting injected electrons.

  For example, organometallic complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorenone derivatives, thiopyrandioxide derivatives, etc. are used for the electron injecting and transporting layer. It can be mentioned as a compound having an electron injection function. Examples of the organometallic complex having an electron injecting function used in the electron injecting and transporting layer include organic aluminum complexes such as tris (8-quinolinolato) aluminum and organic compounds such as bis (10-benzo [h] quinolinolato) beryllium. Examples thereof include a beryllium complex, a beryllium salt of 5-hydroxyflavone, and an aluminum salt of 5-hydroxyflavone. As the compound having an electron injecting function used in the electron injecting and transporting layer, an organoaluminum complex is preferable, and an organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand is more preferable.

  Examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolylate ligand include compounds represented by general formula (a) to general formula (c).

(Q) ₃ -Al (a)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand)

(Q) ₂ -Al-OL '(b)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolato ligand, OL ′ represents an aryloxy ligand, and L ′ represents a hydrocarbon group having 6 to 24 carbon atoms)

(Q) _2- Al-O-Al- (Q) ₂ (c)
(Wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand)

Specific examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand include, for example, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl- 8-quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum,
Bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-methylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-methylphenolate) ) Aluminum, bis (2-methyl-8-quinolinolato) (4-methylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolato) aluminum,

Bis (2-methyl-8-quinolinolato) (3-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (2 , 3-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,6-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum Bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-di-tert-butylphenolato) aluminum, bis (2 -Methyl-8-quinolinolate) (2,6-diphenylphenolate) alumini Arm, bis (2-methyl-8-quinolinolato) (2,4,6-phenylphenolato) aluminum,

Bis (2-methyl-8-quinolinolato) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-Methyl-8-quinolinolato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenylphenol) Lat) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2, 4-Dimethyl-8-quinolinolate) (3,5-dimethylphenolate) Miniumu, bis (2,4-dimethyl-8-quinolinolato) (3,5-di -tert- butyl phenolate) aluminum,

Bis (2-methyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) aluminum-μ-oxo-bis (2, 4-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-4-ethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2- Methyl-4-methoxy-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum-μ- Oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bi (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum.
A compound having an electron injection function may be used alone or in combination.

As the cathode 6, it is preferable to use a metal, an alloy or a conductive compound having a relatively small work function as an electrode material. Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium, manganese, yttrium, and aluminum. , Aluminum-lithium alloy, aluminum-calcium alloy, aluminum-magnesium alloy, lithium fluoride-aluminum alloy, and graphite thin film. These electrode materials may be used alone or in combination.
For the cathode, these electrode materials can be formed on the electron injecting and transporting layer by, for example, vapor deposition, sputtering, ion vapor deposition, ion plating, or cluster ion beam.

  The cathode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the cathode is preferably several hundred Ω or less. The thickness of the cathode is usually 5 to 1000 nm, preferably 10 to 500 nm, although it depends on the electrode material used. In order to efficiently extract light emitted from the organic electroluminescent device of the present invention, at least one of the anode and the cathode is preferably transparent or translucent, and generally has a transmittance of emitted light of 70% or more. It is preferable to set the material and thickness of the anode or cathode.

  The organic electroluminescent device of the present invention may contain a singlet oxygen quencher in at least one of the hole injection transport layer, the light emitting layer, and the electron injection transport layer. Although it does not specifically limit as a singlet oxygen quencher, For example, rubrene, a nickel complex, diphenylisobenzofuran is mentioned, Preferably it is rubrene.

The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injection transport layer, and more preferably a hole injection transport layer. When a singlet oxygen quencher is contained in the hole injecting and transporting layer, it may be uniformly contained in the hole injecting and transporting layer, and a layer adjacent to the hole injecting and transporting layer (for example, a light emitting layer, a light emitting function). May be contained in the vicinity of the electron injecting and transporting layer).
The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.05 to 30% by weight, based on the total amount constituting the layer to be contained (for example, hole injection transport layer). Preferably, it is 0.1 to 20% by weight.

  The formation method of the hole injection transport layer, the light emitting layer, and the electron injection transport layer is not particularly limited. For example, a vacuum deposition method, an ionization deposition method, a solution coating method (for example, a spin coating method, a casting method, A dip coat method, a bar coat method, a roll coat method, a Langmuir-Blodget method, an ink jet method) can be used.

When forming each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer by a vacuum deposition method, the conditions for vacuum deposition are not particularly limited, but a vacuum of about 10 ⁻³ Pa or less is usually used. Below, it is preferable to carry out at a boating temperature (deposition source temperature) of about 50 to 500 ° C., a substrate temperature of about −50 to 300 ° C., and a deposition rate of about 0.005 to 50 nm / sec. In this case, each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer is preferably formed continuously under vacuum. It becomes possible to manufacture an organic electroluminescent element excellent in various characteristics by forming continuously. When each layer such as hole injection transport layer, light emitting layer, electron injection transport layer, etc. is formed using a plurality of compounds by vacuum deposition, the temperature of each boat containing the compounds is individually controlled and co-evaporated. It is preferable to do.

  When each layer is formed by a solution coating method, the component forming each layer or the component and a binder resin are dissolved or dispersed in a solvent to obtain a coating solution. Examples of the solvent include organic solvents (hydrocarbon solvents such as hexane, octane, decane, toluene, xylene, ethylbenzene, and 1-methylnaphthalene, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, dichloromethane, and chloroform. , Halogenated hydrocarbon solvents such as tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, ester solvents such as ethyl acetate, butyl acetate, amyl acetate, ethyl lactate, methanol, propanol, butanol , Pentanol, hexanol, cyclohexanol, methyl cellosolve,

Alcohol solvents such as ethyl cellosolve and ethylene glycol, ether solvents such as dibutyl ether, tetrahydrofuran, dioxane, dimethoxyethane, anisole, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, And polar solvents such as 1,3-dimethyl-2-imidazolidinone and dimethyl sulfoxide) and water. A solvent may be used independently and may be used together. When the components of the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer are dispersed in a solvent, for example, a ball mill, a sand mill, a paint shaker, an attritor, a homogenizer or the like is used as a dispersion method. Can be used.

  Examples of binder resins that can be used for each layer such as a hole injecting and transporting layer, a light emitting layer, and an electron injecting and transporting layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl methacrylate, poly Methyl acrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and derivatives thereof, polythiophene and derivatives thereof, polyphenylene vinylene and derivatives thereof, polyfluorene and derivatives thereof, Examples thereof include polymer compounds such as polythienylene vinylene and its derivatives. Binder resins may be used alone or in combination.

The concentration of the coating solution is not particularly limited, but can be set to a concentration range suitable for producing a desired thickness by the coating method to be carried out, usually 0.1 to 50% by weight, preferably 1 to 30% by weight. When a binder resin is used, the amount used is not particularly limited, but it is usually based on the total amount of components and binder resin that form each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer. It is used such that the content of the binder resin is 5 to 99.9% by weight, preferably 10 to 99% by weight (relative to the total amount of each component in the case of forming a single-layer element).
The thickness of each layer such as the hole injection transport layer, the light emitting layer, and the electron injection transport layer is not particularly limited, but is usually 5 nm to 5 μm.

The organic electroluminescent device of the present invention produced under the above conditions is provided with a protective layer (sealing layer) for the purpose of preventing contact with oxygen, moisture, etc. For example, it can be protected by enclosing it in paraffin, liquid paraffin, silicon oil, fluorocarbon oil, zeolite-containing fluorocarbon oil). Examples of the material used for the protective layer include organic polymer materials (for example, fluorine resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, Polyphenylene oxide), inorganic materials (for example, diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide, metal sulfide), and photocurable resin. The material used for the protective layer may be used alone or in combination. The protective layer may have a single layer structure or a multilayer structure.
Moreover, the organic electroluminescent element of this invention can also provide a metal oxide film (for example, aluminum oxide film) and a metal fluoride film as a protective film in an electrode.

The organic electroluminescent element of the present invention can also be provided with an interface layer (intermediate layer) on the surface of the anode. Examples of the material for the interface layer include organic phosphorus compounds, polysilanes, aromatic amine derivatives, and phthalocyanine derivatives.
Furthermore, the surface of an electrode, for example, an anode, can be used by treating the surface with acid, ammonia / hydrogen peroxide, or plasma.

  The organic electroluminescent element of the present invention can be usually used as a direct current drive type element, but can also be used as an alternating current drive type element. Further, the organic electroluminescence device of the present invention may be a segment type, a passive drive type such as a simple matrix drive type, or an active drive type such as a TFT (thin film transistor) type or a MIM (metal-insulator-metal) type. It may be. The driving voltage is usually 2 to 30V. The organic electroluminescent element of the present invention includes a panel-type light source (for example, a backlight for a clock, a liquid crystal panel, etc.), various light-emitting elements (for example, an alternative to a light-emitting element such as an LED), and various display elements [for example, information display Element (PC monitor, mobile phone / mobile terminal display element)], various signs, various sensors, and the like.

  EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not limited to a following example.

Production of Illustrative Compound 1 [1]: Production of 9-phenylphenanthrene 9-Bromophenanthrene 100 g (0.40 mol), phenylboric acid 50 g (0.40 mol), sodium carbonate 84.8 g (0.80 mol), toluene (600 ml) , Water (300 ml) and tetrakis (triphenylphosphine) palladium 3.16 g (0.0027 mol) were stirred at 50 ° C. for 6 hours. After stirring, the mixture was cooled to room temperature, and the organic layer was separated. By drying with magnesium sulfate and concentrating, 114.4 g of crude crystals were obtained. Furthermore, 88.0 g of the intended 9-phenylphenanthrene was obtained as white crystals by recrystallizing the crude crystals with 1000 ml of ethanol.

[2]: Production of 9-bromo-10-phenylphenanthrene To a carbon tetrachloride solution (500 ml) of 9-phenylphenanthrene 75 g (0.30 mol), 48.0 g (0.30 mol) of bromine was added under reflux. The mixture was refluxed for 4 hours, and further 48.0 g (0.30 mol) of bromine was added under reflux and refluxed for 2 hours. After cooling to room temperature, 50% phosphinic acid aqueous solution (250 ml) was added and stirred at room temperature for 30 minutes. After stirring, the organic layer was separated and washed with water. Drying with magnesium sulfate and concentration gave 60.5 g of crude crystals. Further, the crude crystals were washed with 200 ml of hexane and recrystallized with 600 ml of hexane to obtain 52.9 g of the intended 9-bromo-10-phenylphenanthrene as white crystals.

[3]: Preparation of 9- (N-phenyl) amino-10-phenylphenanthrene 9-Bromo-10-phenylphenanthrene 40.0 g (0.12 mol), aniline 56.0 g (0.60 mol), sodium-tert- Butoxide 13.8 g (0.14 mol), 1,1′-bis (diphenylphosphinoferrocene) palladium dichloromethane complex 4.08 g (0.0050 mol), 1,1′-bis (diphenylphosphinoferrocene) 7.98 g ( 0.014 mol) was stirred at 90 ° C. for 3 hours. After cooling to 25 ° C., methanol (100 ml) was added, and the precipitated crystals were collected by filtration. The crude crystal was washed with methanol (600 ml) to obtain 38.3 g of the intended 9- (N-phenyl) amino-10-phenylphenanthrene as white crystals.

[4]: Production of Exemplified Compound 1 9- (N-phenyl) amino-10-phenylphenanthrene 20.0 g (0.058 mol), iodobenzene 23.7 g (0.116 mol), palladium acetate 0.34 g (0. 002 mol), 0.1 g (0.005 mol) of tri-tert-butylphosphine, and 11.1 g (0.116 mol) of sodium tert-butoxide in xylene (50 ml) were stirred at 110 ° C. for 6 hours. After cooling, methanol (500 ml) was added, and the precipitated crude product was collected by filtration and suspended in an acetonitrile (700 ml) solution. After refluxing for 30 minutes, the precipitated crude crystals were filtered off. After drying, the residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from toluene to obtain 10.6 g of the objective exemplified compound 1 as colorless crystals. Further, this compound was purified by sublimation at 320 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 2 In [4] of Example 1, Example 1 except that 29.5 g (0.116 mol) of 1-iodonaphthalene was used instead of 23.7 g (0.116 mol) of iodobenzene. According to the operation described in [4], 8.60 g of Exemplified Compound 2 was obtained. Further, this compound was purified by sublimation at 360 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 6 In [4] of Example 1, Example 3 was used except that 30.0 g (0.116 mol) of 9-bromophenanthrene was used instead of 23.7 g (0.116 mol) of iodobenzene. In accordance with the operation described in [4], 9.37 g of Exemplified Compound 6 was obtained. Further, this compound was purified by sublimation at 360 ° C. and 2 × 10 ⁻⁴ Pa. Tg was 135.7 ° C.

Production of Exemplified Compound 7 In [4] of Example 1, in place of using 23.7 g (0.116 mol) of iodobenzene, 32.6 g (0.116 mol) of 1-bromopyrene was used. 4] According to the operation described in 7.], 7.89 g of Exemplified Compound 7 was obtained. Further, this compound was purified by sublimation at 400 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 62 In [4] of Example 1, Example 2 except that 27.1 g (0.116 mol) of 4-iodoanisole was used instead of 23.7 g (0.116 mol) of iodobenzene. According to the operation described in [4], 6.53 g of Exemplified Compound 62 was obtained. Further, this compound was purified by sublimation at 400 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplary Compound 94 In [4] of Example 1, except that 23.7 g (0.116 mol) of iodobenzene was used, 38.6 g (0.116 mol) of 9-bromo-10-phenylphenanthrene was used. In accordance with the operation described in [4] of Example 1, 11.2 g of Exemplified Compound 94 was obtained. Further, this compound was purified by sublimation at 360 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 138 [1]: Production of 2-amino-4′-chlorobiphenyl 4-chlorophenylboric acid 50.0 g (0.32 mol), 2-iodoaniline 70.0 g (0.32 mol), sodium carbonate 85 A solution consisting of 0.0 g (0.80 mol), toluene (200 ml), water (100 ml) and tetrakis (triphenylphosphine) palladium 1.0 g (0.0032 mol) was stirred at 80 ° C. for 8 hours. After stirring, the mixture was cooled to room temperature, and the organic layer was separated. This was concentrated, 35% aqueous hydrochloric acid solution (500 ml) was added, and the mixture was stirred for 30 min. The precipitated crystals were separated by filtration, washed with water, and then washed with toluene. The obtained crude crystals (51.2 g) were suspended in toluene (500 ml), and a saturated aqueous sodium hydrogen carbonate solution (500 ml) was added dropwise. After stirring for 1 hour, the organic layer was separated and washed with water. By drying with magnesium sulfate and concentrating, 47.4 g of the desired 2-amino-4′-chlorobiphenyl was obtained as a yellow liquid.

[2]: Production of 4-chloro-2′-iodobiphenyl To 47.0 g (0.23 mol) of 2-amino-4′-chlorobiphenyl, a 25% aqueous sulfuric acid solution (100 ml) was added dropwise at 5 ° C. After stirring for 30 minutes, a 25% aqueous sodium nitrite solution (100 ml) was added dropwise thereto at 5 ° C. After stirring for 30 minutes, 1.0 g (0.016 mol) of copper powder was added, and a 53% potassium iodide aqueous solution (100 ml) was added dropwise at 5 ° C. After stirring for 6 hours, chloroform (1 L) was added. After stirring for 30 minutes, the organic layer was separated, washed with water, washed with 10% aqueous sodium hydroxide (500 ml) and 50% aqueous phosphinic acid (100 ml), dried over magnesium sulfate, and concentrated. 51.0 g of the obtained crude product was purified by silica gel column chromatography (eluent: toluene) to obtain 50.0 g of the target 4-chloro-2′-iodobiphenyl as a yellow liquid.

[3]: Production of 2-chloro-9,10-diphenylphenanthrene 4-chloro-2'-iodobiphenyl 50.0 g (0.16 mol), diphenylacetylene 31.2 g (0.18 mol), lithium chloride 6.74 g (0.16 mol), sodium acetate 26.1 g (0.32 mol), palladium acetate 1.78 g (0.0080 mol) and dimethylformamide (200 ml) were stirred at 100 ° C. for 144 hours. After cooling to 25 ° C., water (1 L) and dichloromethane (1 L) were added, the organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated. The crude product was washed with methanol (600 ml) and recrystallized with toluene to obtain 52.7 g of the desired 2-chloro-9,10-diphenylphenanthrene as white crystals.

[4] Production of Exemplified Compound 138 In [4] of Example 1, instead of using 23.7 g (0.116 mol) of iodobenzene, 42.2 g (0.116 mol) of 2-chloro-9,10-diphenylphenanthrene was used. According to the procedure described in [4] of Example 1, except that was used, 15.3 g of Exemplified Compound 138 was obtained. Further, this compound was purified by sublimation at 410 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁴ Pa. First, 4,4′-bis (N-phenyl-N-1 ″ -naphthylamino) -1,1′-biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec. Next, as a light emitting layer on the hole injection / transport layer, Exemplified Compound 1 and 4,4′-bis [2 ″-(4 ″ ′-N, N-diphenylamino) Phenyl) vinyl] biphenyl was co-deposited to a thickness of 40 nm at a deposition rate of 0.2 nm / sec and 0.02 to 0.1 nm / sec, respectively (weight ratio 10: 1) to form a light emitting layer. Tris (8-quinolinolato) aluminum was deposited on the layer at a deposition rate of 0.2 nm / sec to a thickness of 15 nm to form an electron injecting and transporting layer, and magnesium and silver were deposited thereon as a cathode. 2 at 0.2 nm / sec A cathode was formed by co-evaporation to a thickness of 00 nm (weight ratio 10: 1) to produce an organic electroluminescent device, and the vapor deposition was carried out while maintaining the reduced pressure state of the vapor deposition tank. A direct current voltage was applied to the light emitting element, and it was continuously driven at a constant current density of 10 mA / cm ^{2 in} a dry atmosphere at 50 ° C. Initially, the initial voltage value of the organic electroluminescent element was 4.8V. The emission of blue light with a luminance of 500 cd / m ² was confirmed, and the half life of the luminance of the organic electroluminescent element was 840 hours.

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8 except that Exemplified Compound 2 was used instead of Exemplified Compound 1 in forming the light emitting layer. Further, in the same manner as in Example 8, a DC voltage was applied to the device, and the characteristics of the device were measured. The results are shown in Table 16 (Table 16).

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8 except that Exemplified Compound 6 was used instead of Exemplified Compound 1 in forming the light emitting layer. Further, in the same manner as in Example 8, a DC voltage was applied to the device, and the characteristics of the device were measured. The results are shown in Table 16 (Table 16).

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8 except that Exemplified Compound 7 was used instead of Exemplified Compound 1 in forming the light emitting layer. Further, in the same manner as in Example 8, a DC voltage was applied to the device, and the characteristics of the device were measured. The results are shown in Table 16 (Table 16).

  In Example 8, when the light emitting layer was formed, an organic electroluminescent device was produced according to the procedure described in Example 8, except that Exemplified Compound 62 was used instead of Exemplified Compound 1. Further, in the same manner as in Example 8, a DC voltage was applied to the device, and the characteristics of the device were measured. The results are shown in Table 16 (Table 16).

  In Example 8, an organic electroluminescent element was produced according to the procedure described in Example 8 except that Exemplified Compound 94 was used instead of Exemplified Compound 1 in forming the light emitting layer. Further, in the same manner as in Example 8, a DC voltage was applied to the device, and the characteristics of the device were measured. The results are shown in Table 16 (Table 16).

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8 except that Exemplified Compound 138 was used instead of Exemplified Compound 1 in forming the light emitting layer. Further, in the same manner as in Example 8, a DC voltage was applied to the device, and the characteristics of the device were measured. The results are shown in Table 16 (Table 16).

(Comparative Example 1):
In Example 8, the formation of the light emitting layer was carried out except that 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was used instead of Example Compound 1. According to the operation described in Example 8, an organic electroluminescent device was produced. Blue light emission was confirmed from the device. The results are shown in Table 16 (Table 16).

(Comparative Example 2):
In Example 8, the procedure described in Example 8 was followed except that N, N-diphenyl-4- (1,2-diphenylethynyl) aniline was used in place of Exemplified Compound 1 in forming the light emitting layer. An organic electroluminescent element was produced. Blue light emission was confirmed from the device. The results are shown in Table 16 (Table 16).

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Pa.

  First, poly (thiophene-2,5-diyl) was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injection transport layer. Next, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] -1,1′-biphenyl was deposited to a thickness of 55 nm at a deposition rate of 0.2 nm / sec. A hole injection transport layer was formed. Next, 4,4′-bis (2 ″, 2 ″ -diphenylvinyl) -1,1′-biphenyl and Exemplified Compound 1 are deposited on the hole injecting and transporting layer at a deposition rate of 0.2 nm / sec and 0. A light emitting layer was formed by vapor deposition at 02 nm / sec to a thickness of 40 nm. Further, tris (8-quinolinolato) aluminum was deposited on the light emitting layer to a thickness of 50 nm at a deposition rate of 0.2 nm / sec. An injection transport layer was formed. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was implemented, maintaining the pressure reduction state of a vapor deposition tank.

A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. The initial voltage value of this organic electroluminescent element was 5.1 V and the emission of blue light with a luminance of 510 cd / m ² was confirmed. The half life of the luminance of this organic electroluminescent element was 1640 hours.

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Pa.

  First, 4,4 ′, 4 ″ -tris [N- (3 ″ -methylphenyl) -N-phenylamino] triphenylamine is deposited on an ITO transparent electrode at a deposition rate of 0.1 nm / sec and a thickness of 50 nm. To form a first hole injection transport layer. Next, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] -1,1′-biphenyl was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec. A hole injection transport layer was formed. Furthermore, exemplary compound 1 was vapor-deposited thereon at a thickness of 40 nm at 0.1 nm / sec to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was vapor-deposited thereon to a thickness of 50 nm at a vapor deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, thereby producing an organic electroluminescent device.

A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. As a result, it was confirmed that the organic electroluminescent element emitted blue light with an initial voltage value of 4.9 V and a luminance of 490 cd / m ² . The luminance half life of this organic electroluminescent element was 1710 hours.

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Pa.

First, poly (thiophene-2,5-diyl) was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a hole injection transport layer. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was again depressurized to 3 × 10 ⁻⁶ Pa. Next, Exemplified Compound 6 and rubrene were co-deposited to a thickness of 55 nm from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec (weight ratio 10: 1) to form a light emitting layer. Next, while maintaining the reduced pressure state, tris (8-quinolinolato) aluminum was deposited thereon to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Further, while maintaining the reduced pressure state, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode. A light emitting element was manufactured.

A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. The initial voltage value of this organic electroluminescent element was confirmed to be yellow light emission with 5.8 V and luminance of 610 cd / m ² . The half life of the luminance of this organic electroluminescent element was 1780 hours.

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further UV / ozone cleaned, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Pa.

First, Exemplified Compound 6 was deposited on an ITO transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a hole injecting and transporting layer. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was again depressurized to 3 × 10 ⁻⁶ Pa. Next, Exemplified Compound 1 and rubrene were co-deposited (weight ratio 10: 1) to a thickness of 55 nm from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited thereon to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was implemented, maintaining the pressure reduction state of a vapor deposition tank.

A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. The initial voltage value of the organic electroluminescent element was 6.1 V, and yellow light emission with a luminance of 580 cd / m ² was confirmed. The half life of luminance of this organic electroluminescent element was 1790 hours.

(Comparative Example 3)
As described in Example 18, except that N, N-di (phenanthren-9-yl) -N-phenylamine was used in place of Example Compound 6 in forming the hole injecting and transporting layer in Example 18. According to the operation, an organic electroluminescent device was produced. A DC voltage was applied to the produced organic electroluminescence device, and the organic electroluminescence device was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. The initial voltage value of the organic electroluminescence element was confirmed to be yellow light emission of 6.7 V and luminance of 520 cd / m ² . The half life of the luminance of this organic electroluminescent element was 1015 hours.

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas and further UV / ozone cleaned. Next, on the ITO transparent electrode, a 40 nm hole injection transport is carried out by spin coating using a 3 wt% dichloroethane solution containing polycarbonate (weight average molecular weight 39000) and Exemplified Compound 1 at a weight ratio of 100: 50. A layer was formed. Next, the glass substrate having this hole injecting and transporting layer was fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition layer was decompressed to 3 × 10 ⁻⁶ Pa. Next, tris (8-quinolinolato) aluminum was vapor-deposited thereon to a thickness of 50 nm at a vapor deposition rate of 0.2 nm / sec to form a light-emitting layer also serving as an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, thereby producing an organic electroluminescent device.

When a DC voltage of 10 V was applied to the produced organic electroluminescent element in a dry atmosphere, a current of 84 mA / cm ² flowed, and green light emission with a luminance of 670 cd / m ² was confirmed. The half time of luminance of this organic electroluminescent element was 380 hours.

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas and further UV / ozone cleaned. Next, on the ITO transparent electrode, polymethyl methacrylate (weight average molecular weight 25000), a mixture of Exemplified Compound 94 and Exemplified Compound 138 (mixing ratio 1: 1), and tris (8-quinolinolato) aluminum are respectively in a weight ratio of 100: 50. : A light emitting layer having a thickness of 100 nm was formed by a spin coating method using a 3 wt% dichloroethane solution contained in a ratio of 0.5. Next, the glass substrate having the light emitting layer was fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition layer was decompressed to 3 × 10 ⁻⁶ Pa. On the light emitting layer, magnesium and silver were co-evaporated to a thickness of 200 nm at a deposition rate of 0.2 nm / sec (weight ratio 10: 1) as a cathode to form a cathode, and an organic electroluminescent device was produced.

Fabricated organic electroluminescent dry atmosphere to the light emitting element, upon application of a direct current voltage of 15V, current flows in 85mA / cm ^2, green light emission luminance 820 cd / ^{m 2} was observed. The half life of the luminance of this organic electroluminescent element was 515 hours.

  According to the present invention, it is possible to provide a novel triarylamine compound and an organic electroluminescence device using the triarylamine compound, which has a long emission lifetime and excellent durability.

It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element. It is a cross-sectional schematic diagram of an example of an organic electroluminescent element.

Explanation of symbols

1: Substrate 2: Anode 3: Hole injection / transport layer 3a: Hole injection / transport component 4: Light emitting layer 4a: Light emission component 5: Electron injection / transport layer 5 ″: Electron injection / transport layer 5a: Electron injection / transport component 6: Cathode 7: Power supply

Claims (8)

A triarylamine compound represented by the general formula (1).

[Wherein, Ar ¹ and Ar ² each independently represent a substituted or unsubstituted aryl group having 5 to 38 carbon atoms,
Ar ³ represents a phenyl group, a naphthyl group or a phenanthryl group which may be unsubstituted or substituted with a methyl group or a methoxy group;
Z ^{1 to} Z ⁸ are each independently a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 4 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 4 carbon atoms, carbon It represents an amino group substituted with a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, or a substituted or unsubstituted aralkyl group with 7 to 13 carbon atoms.
Moreover, the adjacent groups of Z ^{1 to} Z ⁸ may form a ring together with the adjacent groups.
Here, the substituent that the aryl group of Ar ¹ and Ar ² may have and the substituent that the aryl group of Z ^{1 to} Z ⁸ may have are a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. , Isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, tert-pentyl group, hexyl group, ethylhexyl group, heptyl group, octyl group, tert-octyl group, nonyl group, decyl group, dodecyl group Tetradecyl group, hexadecyl group, octadecyl group, cyclopentyl group, cyclohexyl group, tert-butylcyclohexyl group, neopentyl group,
Phenyl group, naphthalen-1-yl group, naphthalen-2-yl group, phenanthren-9-yl group,
Methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, isopentyloxy group, neopentyloxy group, hexyloxy group, ethylbutyloxy group, octyl Oxy group, decyloxy group, dodecyloxy group, tetradecyloxy group, hexadecyloxy group, octadecyloxy group, cyclohexyloxy group,
Fluoro atom, chloro atom, bromo atom, trifluoromethyl group, trifluoromethyloxy group,
Nitro group, allyl group, isopropenyl group, benzyl group, methylbenzyl group, cumyl group, methoxycumyl group,
Methylphenyl, ethylphenyl, isopropylphenyl, tert-butylphenyl, hexylphenyl, octylphenyl, methoxyphenyl, ethoxyphenyl, butoxyphenyl, fluorophenyl, chlorophenyl, methoxymethyl, ethoxy Methyl group, butyloxymethyl group, methoxymethyl group, methoxyethyl group,
Ethoxyethyloxy group, butyloxyethyloxy group, ethoxypropyloxy group, vinyloxy group, allyloxy group, pentenyloxy group, allyloxymethyl group, allyloxyethyloxy group, benzyloxy group, phenethyloxy group, chlorobenzyloxy group, Methylbenzyloxy group, methoxybenzyloxy group, ethoxybenzyloxy group, benzyloxymethyl group, benzyloxyethyloxy group, phenyloxy group, methylphenyloxy group, methoxyphenyloxy group, chlorophenyloxy group,
Phenyloxymethyl group, phenyloxyethoxy group, methylphenyloxyethoxy group, methoxyphenyloxyethoxy group, chlorophenyloxyethoxy group,
Acetyl group, ethylcarbonyl group, butylcarbonyl group, hexylcarbonyl group, octylcarbonyl group, cyclohexylcarbonyl group, allylcarbonyl group, benzylcarbonyl group, methylbenzylcarbonyl group, phenylcarbonyl group, methylphenylcarbonyl group, chlorophenylcarbonyl group,
Methoxycarbonyl group, ethoxycarbonyl group, propyloxycarbonyl group, butyloxycarbonyl group, hexyloxycarbonyl group, decyloxycarbonyl group, cyclohexyloxycarbonyl group, butyloxycarbonyl group, allyloxycarbonyl group, benzyloxycarbonyl group, chlorobenzyl An oxycarbonyl group, a phenethyloxycarbonyl group, a phenyloxycarbonyl group,
Ethylphenyloxycarbonyl group, chlorophenyloxycarbonyl group, ethoxyphenyloxycarbonyl group,
Acetyloxy group, ethylcarbonyloxy group, propylcarbonyloxy group, pentylcarbonyloxy group, octylcarbonyloxy group, cyclohexylcarbonyloxy group, butylcarbonyloxy group, allylcarbonyloxy group, benzylcarbonyloxy group, phenethylcarbonyloxy group,
Phenylcarbonyloxy group, methylphenylcarbonyloxy group, chlorophenylcarbonyloxy group,
Methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, hexylthio group, octylthio group, cyclohexylthio group, benzylthio group, chlorobenzylthio group, phenylthio group, methylphenylthio group, methoxyphenylthio group , Chlorophenylthio group,
Formyl group, pyrrolidino group, piperidino group, morpholino group, N-ethylpiperazino group,
Amino group, N-methylamino group, N-ethylamino group, N-isopropylamino group, N-butylamino group, N-octylamino group, N-dodecylamino group, N-benzylamino group, N-phenylamino group N, N-dimethylamino group, N, N-diethylamino group, N, N-dibutylamino group, N, N-dihexylamino group, N-cyclohexyl-N-methylamino group, N-benzyl-N-phenylamino Group, N, N-diphenylamino group, N-phenyl-N- (methylphenyl) amino group, N, N-di (methylphenyl) amino group, N, N-di (methoxyphenyl) amino group,
N- (naphthalen-1-yl) -N-phenylamino group, N- (anthracen-2-yl) -N-phenylamino group, N- (9-phenanthryl) -N-phenylamino group, N, N- Di (naphthalen-1-yl) amino group, N- (naphthalen-1-yl) -N- (9-phenanthryl) amino group, N- (methylphenyl) -N-phenylamino group, N- (naphthalene-2 -Yl) -N- (9-phenanthryl) amino group,
One or more groups selected from the group consisting of a hydroxy group and a cyano group.
The substituent that the aryl group in the amino group of Z ^{1 to} Z ⁸ has is one or more groups selected from the group consisting of a methyl group, a methoxy group, and a fluoro group .
The substituents that the aralkyl group of Z ^{1 to} Z ⁸ may have are a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a tert-pentyl group, a cyclohexyl group, an allyl group, a phenyl group, a methoxy group, and an ethoxy group. One or more groups selected from the group consisting of n-butoxy group, heptyloxy group, methoxymethyl group, isobutyloxymethyl group, allyloxy group, vinyloxymethyl group, phenyloxy group, hydroxy group, fluoro atom and chloro atom is there. ] The triarylamine compound according to claim 1, wherein Ar ¹ or Ar ² is a phenanthryl group substituted with an aryl group. The triarylamine compound according to claim 1, wherein Ar ¹ and Ar ² are the substituted or unsubstituted aryl group having 5 to 38 carbon atoms which is not a substituted or unsubstituted phenanthryl group. An organic electroluminescence device comprising at least one layer containing at least one triarylamine compound represented by the general formula (1) according to any one of claims 1 to 3 between a pair of electrodes. The organic electroluminescent element of Claim 4 whose layer containing the triarylamine compound represented by the said General formula (1) is a light emitting layer. Formula (1) a layer containing a triarylamine compound represented by the organic electroluminescent device according to claim 4, wherein a hole injection transport layer.   The organic electroluminescent element according to any one of claims 4 to 6, further comprising a hole injection transport layer between the pair of electrodes. The organic electroluminescent element according to claim 4, further comprising an electron injecting and transporting layer between the pair of electrodes.

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