JP4388391B2 - Fluorene compound and organic electroluminescence device containing the fluorene compound - Google Patents

Description

  The present invention relates to a novel fluorene compound and an organic electroluminescence device comprising the fluorene 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, in general, the light emission luminance is low and the light emission lifetime is short, which is not sufficient for practical use.

As a method for improving the light emission luminance and the light emission lifetime, for example, an organic electroluminescent element using a fluorene compound has been proposed (for example, Patent Document 1). However, it cannot be said that these light-emitting elements also have sufficiently satisfactory light emission luminance and light emission lifetime, and at present, new and improved compounds are desired.
Appl.Phys.Lett., 51,913 (1987) JP 2002-154993 A

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

In order to solve the above problems, the present inventors have conducted extensive studies on various fluorene compounds, in particular, fluorene compounds that can be suitably used for charge injection and transport materials and light emitting layers of organic electroluminescent devices. It came to complete. That is, the present invention
<1>: A fluorene compound represented by the general formula (1),

[Wherein R ^{1 to} R ⁶ are each independently a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl. Represents a group, and R ^{1 to} R ⁶ may be bonded to each other to form a ring. A represents an anthracenediyl group. 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 It represents an aryl group or a substituted or unsubstituted aralkyl group, and Z ^{1 to} Z ⁶ may be bonded to each other to form a ring. ]

<2>: An organic electroluminescent device comprising at least one layer containing at least one fluorene 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 fluorene compound and an organic electroluminescence device having a long emission lifetime and excellent durability.

Hereinafter, the present invention will be described in detail.
The fluorene compound of the present invention is a compound represented by the general formula (1).

[Wherein R ^{1 to} R ⁶ are each independently a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl. Represents a group, and R ^{1 to} R ⁶ may be bonded to each other to form a ring. A represents an anthracenediyl group. 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 It represents an aryl group or a substituted or unsubstituted aralkyl group, and Z ^{1 to} Z ⁶ may be bonded to each other to form a ring. ]

In the fluorene compound represented by the general formula (1), R ^{1 to} R ⁶ are each independently a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, substituted or unsubstituted aryl. Represents a group, or a substituted or unsubstituted aralkyl group. The aryl group includes a carbocyclic aromatic group and a heterocyclic aromatic group. The aryl group of the aralkyl group similarly includes a carbocyclic aromatic group and a heterocyclic aromatic group.

R ^{1 to} R ⁶ are preferably a linear or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 5 to 25 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 16 carbon atoms. More preferably a linear alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, More preferably, it is a linear alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 11 carbon atoms. R ^{1 to} R ⁶ may be bonded to each other to form a ring.

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. 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), 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 by a substituted or unsubstituted aryl group, an amino group substituted by a substituted or unsubstituted aralkyl group having 7 to 13 carbon atoms, 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,

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 10 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 11 carbon atoms. Further, adjacent groups of Z ^{1 to} Z ⁶ may form a ring together with the adjacent groups.

In the compound represented by the general formula (1), specific examples of the linear, branched or cyclic alkyl group represented by R ^{1 to} R ⁶ 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-methyldecyl 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), specific examples of the substituted or unsubstituted aryl group of R ^{1 to} R ⁶ include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, anthracene-2- Yl, anthracen-9-yl, 9-phenanthryl, 9-fluorenyl, 4-quinolyl, 5-pyridyl, 4-pyridyl, 3-pyridyl, 2-pyridyl, 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-ethyl-1-naphthyl group, 6-n-butyl-2-naphthyl group, 1-phenyl-2-naphthyl group, 9 Methyl anthracen-10-yl group, 9-tert-butyl-anthracen-10-yl group, 9-methyl-10-phenanthryl group, 9-tert-butyl-10-phenanthryl group, 9-phenyl-10-phenanthryl group, 1-pyrenyl 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- Dimethylfe Nyl 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-1-naphthyl group, 4-methoxy-1 -Naphthyl group, 4-n-butyloxy-1-naphthyl group,

5-ethoxy-1-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butyloxy-2-naphthyl group, 6-n-hexyloxy-2-naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butyloxy-2-naphthyl 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-methoxyphenyl group, 3-ethyl-5-methoxypheny 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-chloro-1-naphthyl group, 4-chloro-2-naphthyl group, 6-bromo-2-naphthyl 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-1-naphthyl group, 1,6-dichloro-2-naphthyl 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- 1-naphthyl 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-benzyloxy-1-naphthyl group, 5- (4′-methylbenzyloxy) -1-naphthyl group, Zyloxy-2-naphthyl group, 6- (4′-methylbenzyloxy) -2-naphthyl group, 7-benzyloxy-2-naphthyl group, 4- (benzyloxymethyl) phenyl group, 4- (2′-benzyl) Oxyethyloxy) 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-phenyloxy-1-naphthyl group, 6- Phenyloxy-2-naphthyl group, 7-phenyloxy-2-naphthyl group, 4-phenyloxymethylphenyl group, 4- (2′-phenyloxyethoxy) phenyl group, 4- [2 ′-(4′-methyl) Phenyloxy) 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-ethylcarbonylphenyl group, 4- -Butylcarbonylphenyl group, 4-n-hexylcarbonylphenyl group, 4-n-octylcarbonylphenyl group, 4-cyclohexylcarbonylphenyl group, 4-acetyl-1-naphthyl group, 6-acetyl-2-naphthyl group, 6 -N-butylcarbonyl-2-naphthyl 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-phenylcarbonyl- 1-naphthyl group, 4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-n-propyloxycarbonylphenyl group, 4-n-butyloxycarbonyl Phenyl group, 4-n-hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonyl-1-naphthyl group, 6-methoxycarbonyl-2-naphthyl group , 6-n- Tyloxycarbonyl-2-naphthyl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4′-chlorobenzyl) oxycarbonylphenyl group, 4-phenethyloxycarbonylphenyl group, 6-benzyl Oxycarbonyl-2-naphthyl group, 4-phenyloxycarbonylphenyl group,

4- (4′-ethylphenyl) oxycarbonylphenyl group, 4- (4′-chlorophenyl) oxycarbonylphenyl group, 4- (4′-ethoxyphenyl) oxycarbonylphenyl group, 6-phenyloxycarbonyl-2-naphthyl 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-acetyloxy-1-naphthyl group, 4-n-butyl Carbonyl Xyl-1-naphthyl group, 5-acetyloxy-1-naphthyl group, 6-ethylcarbonyloxy-2-naphthyl group, 7-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4-benzylcarbonyl An oxyphenyl group, a 4-phenethylcarbonyloxyphenyl group, a 6-benzylcarbonyloxy-2-naphthyl 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-phenylcarbonyloxy-1-naphthyl group, 6-phenylcarbonyloxy-2-naphthyl group, 7-phenylcarbonyloxy-2-naphthyl 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-isobutylthio Phenyl group, 2-neopentylphenyl group, 4-n- Xylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group, 4-benzylthiophenyl group, 3-benzylthiophenyl group, 2-benzylthiophenyl group, 4- (4′-chlorobenzyl) Thio) 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-ethylthio-1-naphthyl group, 4-methylthio-1-naphthyl group, 6-ethylthio-2-naphthyl group, 6-phenylthio-2-naphthyl group, 4-nitrophenyl group, 3-nitrophenyl group, 2 -Nitrophenyl group, 3,5-dinitrophenyl group, 4-nitro-1-naphthyl group, 4-formylphenyl group, 3-formylphenyl group, 2-formylphenyl group, 4-formyl-1-naphthyl group, 1 -Formyl-2-naphthyl group, 4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morpholinophenyl group, 4- (N-ethylpiperazi ) Phenyl group, 4-pyrrolidino-1-naphthyl 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) -1-naphthyl group, 4 -(N-Benz -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- (1-naphthyl) -N-phenylamino] phenyl group, 4- [N- (anthracen-2-yl) -N-phenylamino] Phenyl group, 4- [N- (9-phenanthryl) -N-phenylamino] phenyl group, 4- [N, N-di (1-naphthyl) amino] phenyl group, 4- [N- (1-naphthyl) -N- (9-phenanthryl) amino] phenyl group, 4- [N- (2-methylphenyl) -N-phenylamino] phenyl group, 4- [N- (2-naphthyl) -N- (9-phenanthryl) ) Amino] phenyl group, 4- [N, N-diphenylamino] -1-naphthyl group,

4-hydroxyphenyl group, 3-hydroxyphenyl group, 2-hydroxyphenyl group, 4-methyl-3-hydroxyphenyl group, 6-methyl-3-hydroxyphenyl group, 2-hydroxy-1-naphthyl group, 8-hydroxy -1-naphthyl group, 4-hydroxy-1-naphthyl group, 1-hydroxy-2-naphthyl group, 6-hydroxy-2-naphthyl group, 4-cyanophenyl group, 2-cyanophenyl group, 4-cyano-1 -Naphthyl group, 6-cyano-2-naphthyl 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-diphenylfluorenefluoren-2-yl group, 9-naphthylfluorene -2-yl group, 9,9-dinaphthylfluoren-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-naphthyl fluoren-2-yl group, 4-phenyl-9,9-dinaphthyl 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-naphthylfluoren-2-yl group, 7-tert-butyl-9,9-dinaphthylfluoren-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-naphthyl fluoren-2-yl group, 7-phenyl-9,9-dinaphthyl 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,

9-trimethylsilylfluoren-2-yl group, 9,9-bis (trimethylsilyl) fluoren-2-yl group, 9-ethyldimethylsilylfluoren-2-yl group, 9,9-bis (ethyldimethylsilyl) fluorene-2 -Yl group, 9-tert-butyldimethylsilylfluoren-2-yl group, 9,9-bis (tert-butyldimethylsilyl) fluoren-2-yl group, 9-cyclohexyldimethylsilylfluoren-2-yl group, 9 , 9-bis (cyclohexyldimethylsilyl) fluoren-2-yl group, 9-dicyclohexyldimethylsilylfluoren-2-yl group, 9,9-bis (dicyclohexyldimethylsilyl) fluoren-2-yl group, 9-dimethylphenylsilyl Fluoren-2-yl group, 9,9-bis (dimethylphenylsilyl) Luolen-2-yl group, 4-fluoro-9-trimethylsilylfluoren-2-yl group, 4-fluoro-9,9-bis (trimethylsilyl) fluoren-2-yl group, 7-fluoro-9-trimethylsilylfluorene-2 -Yl group, 7-fluoro-9,9-bis (trimethylsilyl) fluoren-2-yl group,

4-trifluoromethyl-9-trimethylsilylfluoren-2-yl group, 4-trifluoromethyl-9,9-bis (trimethylsilyl) fluoren-2-yl group, 7-trifluoromethyl-9-trimethylsilylfluoren-2- Yl group, 7-trifluoromethyl-9,9-bis (trimethylsilyl) fluoren-2-yl group, 9-tert-butyldimethylsilyl-4-fluorofluoren-2-yl group, 9,9-bis (tert- Butyldimethylsilyl) -4-fluorofluoren-2-yl group, 9-cyclohexyldimethylsilyl-4-cyanofluoren-2-yl group, 9,9-bis (cyclohexyldimethylsilyl) -4-cyanofluoren-2-yl Group, 9-dicyclohexylmethylsilyl-4-cyanofluoren-2-yl group, 9,9- Sus (dicyclohexylmethylsilyl) -4-cyanofluoren-2-yl group, 9-dimethylphenylsilyl-4-trifluorofluoren-2-yl group, 9,9-bis (dimethylphenylsilyl) -4-trifluorofluorene 2-yl group,

10- [9,9-bis (trimethylsilyl) fluoren-2-yl] anthracen-9-yl group, 10- [9,9-bis (ethyldimethylsilyl) fluoren-2-yl] anthracen-9-yl group, 10 -[9,9-bis (tert-butyldimethylsilyl) fluoren-2-yl] anthracen-9-yl group, 10- [9,9-bis (cyclohexyldimethylsilyl) fluoren-2-yl] anthracene-9- Yl group, 10- [9,9-bis (dimethylphenylsilyl) fluoren-2-yl] anthracen-9-yl group,

10- [10 ′-[9 ″, 9 ″ -bis (trimethylsilyl) fluoren-2 ″ -yl] anthracen-9 ″ -yl] anthracen-9′-yl] anthracen-9-yl group, 10− [10 ′-[9 ″, 9 ″ -bis (ethyldimethylsilyl) fluoren-2 ″ -yl] anthracen-9′-yl] anthracen-9-yl group, 10- [10 ′-[9 ′ ', 9 ″ -bis (tert-butyldimethylsilyl) fluoren-2 ″ -yl] anthracene-9′-yl] anthracen-9-yl group, 10- [10 ′-[9 ″, 9 ″ -Bis (cyclohexyldimethylsilyl) fluoren-2 "-yl] anthracen-9'-yl] anthracen-9-yl group, 10- [10 '-[9", 9 "-bis (dimethylphenylsilyl) Fluorene-2 "-Il] Ant Sen-9'-yl] anthracene-9-yl group,

10- [3′-tert-butyl-10 ′-[9 ″, 9 ″ -bis (trimethylsilyl) fluoren-2 ″ -yl] anthracene-9 ″ -yl] anthracene-9′-yl] anthracene- 9-yl group, 10- [3′-tert-butyl-10 ′-[9 ″, 9 ″ -bis (ethyldimethylsilyl) fluoren-2 ″ -yl] anthracene-9′-yl] anthracene- 9-yl group, 10- [3′-tert-butyl-10 ′-[9 ″, 9 ″ -bis (tert-butyldimethylsilyl) fluoren-2 ″ -yl] anthracen-9′-yl] Anthracen-9-yl group, 10- [3′-tert-butyl-10 ′-[9 ″, 9 ″ -bis (cyclohexyldimethylsilyl) fluoren-2 ″ -yl] anthracene-9′-yl] Anthracen-9-yl group, 10- [3′-ter substituted or unsubstituted such as t-butyl-10 ′-[9 ″, 9 ″ -bis (dimethylphenylsilyl) fluoren-2 ″ -yl] anthracen-9′-yl] anthracen-9-yl group An aryl group can be mentioned.

In the compound represented by the general formula (1), specific examples of the substituted or unsubstituted aralkyl group of R ^{1 to} R ⁶ 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-phenethyl Benzyl 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-hydroxybenzyl group Zyl 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 substituted or unsubstituted aralkyl groups such as a diphenylmethyl group, a 1-naphthylmethyl group, a 2-naphthylmethyl group, a 2-pyridylmethyl group, a 3-pyridylmethyl group, and a 4-methylpyridyl group.

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 a linear, branched or cyclic alkyl group of R ^{1 to} R ^6. The linear, branched or cyclic alkyl group mentioned as a specific example of can be mentioned.

In the compound represented by the general formula (1), specific examples of the linear, branched or cyclic alkoxy group of Z ^{1 to} Z ⁸ include, for example, a linear, branched or cyclic group of R ^{1 to} R ⁶ . 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.

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-phenylamino group, N- (1-naphthyl) amino group, N- (2- Naphthyl) amino group, N- (4-phenylphenyl) amino group, N- (3-phenylphenyl) amino group, N- (2-phenylphenyl) amino group,

N- (4-methylphenyl) amino group, N- (2-methylphenyl) amino group, N- (2-anthranyl) amino group, N- (9-anthranyl) amino 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 Ru-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, N-diphenylamino group, N, N-di (1-naphthyl) amino group, N, N-di (2-naphthyl) 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-(1-naphthyl) amino group, N- phenyl-N-(2-naphthyl) amino group, N- phenyl -N- (4- phenylphenyl) amino group,

N-phenyl-N- (4-methylphenyl) amino group, N- (1-naphthyl) -N- (4′-phenylphenyl) amino group, N-phenyl-N- [4- (9′-fluorenyl) Phenyl] amino group, N- (2-tert-butyl-phenyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (3-tert-butyl-phenyl) -N- [ 4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (4-tert-butyl-phenyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (1- Naphthyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (2-naphthyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- ( Anthracen-9-yl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino Group, N- (10-methylanthracen-9-yl) -N- [4 '-(9' '-fluorenyl) phenyl] amino group, N- (10-anthracen-9-yl) -N- [4' -(9 ''-fluorenyl) phenyl] amino group,

N- (10-tert-butylanthracen-9-yl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (9-phenanthryl) -N- [4 ′-(9 ′ '-Fluorenyl) phenyl] amino group, N- (10-methylphenanthrene-9-yl) -N- [4'-(9 ''-fluorenyl) phenyl] amino group, N- (10-tert-butyl-phenanthrene) -9-yl) -N- [4 '-(9' '-fluorenyl) phenyl] amino group, N- (10-phenylphenanthrene-9-yl) -N- [4'-(9 ''-fluorenyl) Phenyl] amino group, N- (2-methylphenyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (3-methylphenyl) -N- [4 ′-(9 ′ '-Fluorenyl) phenyl] amino group, N- (4-methyl Enyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (2-methylphenyl) -N- [4 ′-(9 ″ -fluorenyl) -2′-methylphenyl] An amino group,

N- (2-methoxyphenyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (3-methoxyphenyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl ] Amino group, N- (4-methoxyphenyl) -N- [4 ′-(9 ″ -fluorenyl) phenyl] amino group, N- (2-fluorophenyl) -N- [4 ′-(9 ″) -Fluorenyl) phenyl] amino group, N- (3-fluorophenyl) -N- [4 '-(9' '-fluorenyl) phenyl] amino group, N- (4-fluorophenyl) -N- [4'- (9 ''-fluorenyl) phenyl] 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 are given as specific examples of the substituted or unsubstituted aryl group of R ^{1 to} R ⁶ . Mention may be made of substituted or unsubstituted aryl groups.

In the compound represented by the general formula (1), specific examples of the substituted or unsubstituted aralkyl group of Z ^{1 to} Z ⁸ are given as specific examples of the substituted or unsubstituted aralkyl group of R ^{1 to} R ⁶ . A substituted or unsubstituted aralkyl group can be mentioned.

  In the compound represented by the general formula (1), the anthracenediyl group of A includes anthracene-1,2-diyl group, anthracene-1,4-diyl group, anthracene-1,5-diyl group, anthracene-1 , 6-diyl group, anthracene-1,8-diyl group, anthracene-1,9-diyl group, anthracene-1,10-diyl group, anthracene-2,6-diyl group, anthracene-2,7-diyl group And anthracene-2,9-diyl group, anthracene-2,10-diyl group, and anthracene-9,10-diyl group.

  In the compound represented by the general formula (1), A is preferably anthracene-1,4-diyl group, anthracene-1,5-diyl group, anthracene-2,6-diyl group, anthracene-2,7- A diyl group, an anthracene-1,10-diyl group and an anthracene-9,10-diyl group, more preferably an anthracene-1,4-diyl group, anthracene-2,6-diyl group, anthracene-1,10- A diyl group and an anthracene-9,10-diyl group.

  Specific examples of the fluorene compound represented by the general formula (1) according to the present invention include the following compounds, but the present invention is not limited thereto.

The fluorene compound represented by the general formula (1) of the present invention can be produced by, for example, the following process (Chemical Formula 24).

[Wherein R ^{1 to} R ⁶ , Z ^{1 to} Z ⁸ and A represent the same meaning as in general formula (1), and X represents halogen. ]

That is, a fluorene derivative represented by the general formula (A) and a halogenoanthracene derivative represented by the general formula (B) are converted into a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium]. And the reaction in the presence of a base (for example, potassium carbonate, sodium carbonate, triethylamine, pyridine), a fluorene compound represented by the general formula (1) can be produced. Here, the compound represented by the general formula (B) is obtained by converting a monohalogenoanthracene compound and a compound represented by Z ⁸ -B (OH) ₂ into a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, tris (di- Benzylideneacetone) dipalladium] and a base [eg, potassium carbonate, sodium carbonate, triethylamine, pyridine] and then a halogenating agent [eg, bromine, N-chlorosuccinimide, N-bromosuccinimide, N -Iodosuccinimide] can be produced.

  Moreover, the fluorene derivative represented by general formula (A) can be manufactured by the following processes (chemical formula 25), for example.

[Wherein, R ^{1 to} R ⁶ , Z ^{1 to} Z ⁷ and A represent the same meaning as in the general formula (1), H represents a hydrogen atom, and X represents a halogen. ]

  That is, a halogenating agent [for example, bromine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide] is allowed to act on the fluorene derivative represented by the general formula (C) to represent the general formula (D). A halogenated fluorene derivative is produced, and then magnesium or n-butyl lithium is allowed to act on the halogenated fluorene derivative represented by the general formula (D), and then trialkyl borate [for example, trimethyl borate, boric acid A fluorene derivative represented by the general formula (A) can be produced by reacting triisopropyl] and further hydrolyzing with an acid. Here, the compound represented by the general formula (C) corresponds to a fluorene compound which is not substituted at the 9-position after acting a base [for example, n-butyllithium, potassium hydride, sodium hydride]. It can be produced by reacting with a chlorosilane compound.

  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 fluorene 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 fluorene 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 electroluminescence device of the present invention, the fluorene 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. Is more preferable.

  In the organic electroluminescent element of the present invention, the fluorene 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 is formed of a fluorene 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, hydrazones). Derivatives, stilbene derivatives, pyrazoline derivatives, polysilane derivatives, polyphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, poly-N-vinylcarbazole, and the like).
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 fluorene compound represented by the general formula (1) in the hole injecting and transporting layer. Examples of the compound having a hole injecting and transporting function other than the fluorene compound represented by the general formula (1) of the present invention that can be used in the organic electroluminescent device of the present invention include triarylamine derivatives (for example, 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 ″ -Naphtyl) 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] phenyl] 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 using together the fluorene compound represented by General formula (1) and the compound which has another hole injection function, content of the fluorene compound represented by General formula (1) which occupies in a hole injection transport layer is as follows. Preferably, it is 0.1 mass% or more, More preferably, it is 0.5-99.9 mass%, More preferably, it is 3-97 mass%.

  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 is formed using the fluorene compound represented by the general formula (1) as a host material and at least one compound having a light emitting function other than the fluorene compound represented by the general formula (1) as a guest material. In addition, a compound having a light emitting function other than the fluorene compound represented by the general formula (1) can be used as at least one kind of host material, and the fluorene compound represented by the general formula (1) can be used as a guest material. You can also

  As a compound (guest material / host material) having a light emitting function other than the fluorene 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 (for example, having a hole injection / transport function) The above-mentioned compounds can be mentioned), 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 fluorene compound represented by the general formula (1) (guest material / host material) include acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallic complexes, and stilbenes. Derivatives are preferred, and polycyclic aromatic compounds and organometallic complexes are more preferred.

The organic electroluminescent element of the present invention preferably contains a fluorene compound represented by the general formula (1) as a host material in the light emitting layer.
When the fluorene 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 inclusion of the fluorene compound represented by the general formula (1) in the light emitting layer The rate is preferably 99.9 to 80% by mass, and more preferably 99 to 90% by mass.
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 fluorene compound represented by the general formula (1) of the present invention to the entire host material is preferably 99 to 10% by mass, more preferably 90 to 20% by mass. It is.

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.
Examples of the compound having an electron injecting function used in the electron injecting and transporting layer include organometallic complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorenones. Derivatives, thiopyrandioxide derivatives and the like. Examples of organometallic complexes include organoaluminum complexes such as tris (8-quinolinolato) aluminum, organic beryllium complexes such as bis (10-benzo [h] quinolinolato) beryllium, beryllium salts of 5-hydroxyflavone, 5- Examples thereof include an aluminum salt of hydroxyflavone. 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 alloys, aluminum-calcium alloys, aluminum-magnesium alloys, and graphite thin films. 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).
As content of a singlet oxygen quencher, 0.01-50 mass% of the total quantity which comprises the layer (for example, hole injection transport layer) to contain, Preferably, 0.05-30 mass%, more Preferably, it is 0.1-20 mass%.

  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 the vacuum deposition are not particularly limited, but usually a vacuum of about 10 ⁻⁵ Pa or less. 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.

Although the density | concentration of a coating liquid is not specifically limited, It can set to the density | concentration range suitable for producing desired thickness with the apply | coating method to implement, Usually, 0.1-50 mass%, Preferably 1 to 30% by mass. 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. The binder resin is used so that the content of the binder resin is 5 to 99.9% by mass, preferably 10 to 99% by mass (relative to the total amount of each component when a single-layer element is formed).
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 Exemplified Compound 1 [1]: Production of 9,9-bis (trimethylsilyl) fluorene To 100 ml of a tetrahydrofuran solution of 30.0 g (0.18 mol) of fluorene, 138 ml of a 2.6 M n-butyllithium / hexane solution (0. 36 mol) was added dropwise at 5 ° C. After stirring at 5 ° C. for 2 hours, 100 ml of a tetrahydrofuran solution containing 58.0 g (0.54 mol) of chlorotrimethylsilane was added dropwise at 5 ° C. After stirring at 25 ° C. for 5 hours, 100 ml of water was added dropwise at 25 ° C. 700 ml of toluene was added and the organic layer was separated. Drying with magnesium sulfate and concentration gave 56.4 g of crude crystals. Further, the crude crystals were washed with 200 ml of ethanol to obtain 24.5 g of the intended 9,9-bis (trimethylsilyl) fluorene as colorless crystals.

[2]: Preparation of 2-bromo-9,9-bis (trimethylsilyl) fluorene In 200 ml of a carbon tetrachloride solution of 20.0 g (0.065 mol) of 9,9-bis (trimethylsilyl) fluorene, 10.2 g (0 0.063 mol) of carbon tetrachloride was added dropwise at 5 ° C. After stirring at 25 ° C. for 2 hours, 50 ml of a 50% hypophosphorous acid aqueous solution was added dropwise at 25 ° C. After stirring at 25 ° C. for 0.5 hour, the organic layer was separated, dried over magnesium sulfate, and concentrated to obtain 29 g of crude crystals. Further, the crude crystals were recrystallized with 400 ml of ethanol to obtain 16.1 g of 2-bromo-9,9-bis (trimethylsilyl) fluorene.

[3]: Preparation of 9,9-bis (trimethylsilyl) fluoren-2-ylboronic acid 200 ml of a tetrahydrofuran solution of 15.0 g (0.039 mol) of 2-bromo-9,9-bis (trimethylsilyl) fluorene was added to 1. 1 g (0.046 mol) was added dropwise at 60 ° C. with vigorous stirring. After stirring at 60 ° C. for 5 hours, the mixture was cooled to −40 ° C., and 200 ml of a terahydrofuran solution of 10.0 g (0.096 mol) of trimethyl borate was added dropwise at −40 ° C. After stirring at −40 ° C. for 3 hours, 50 ml of 25% aqueous sulfuric acid solution was added dropwise at −40 ° C. After raising the temperature to 25 ° C., 500 ml of ethyl acetate was added. The organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated to obtain 16.3 g of crude crystals. Further, the crude crystals were washed with 50 ml of hexane to obtain 5.3 g of 9,9-bis (trimethylsilyl) fluoren-2-yl boric acid.

[4]: Production of Exemplary Compound 1 9,9-bis (trimethylsilyl) fluoren-2-ylboric acid 5.0 g (0.014 mol), 9-bromo-10- (2-naphthyl) anthracene 4.6 g (0. 4) 012 mol), 0.13 g (0.0012 mol) of tetrakis (triphenylphosphine) palladium was added to a solution of 2.5 g (0.023 mol) of sodium carbonate in 60 ml of toluene and 30 ml of water, and the mixture was stirred at 90 ° C. for 16 hours. After cooling to 25 ° C., the reaction solution was filtered off, and the organic layer of the filtrate was separated. After washing with water, drying over magnesium sulfate and concentrating, 9.2 g of crude crystals were obtained. Further, the crude crystals were washed with 100 ml of methanol, purified by silica gel column chromatography (eluent: toluene), and recrystallized with toluene to obtain 6.1 g of Exemplified Compound 1. Further, this compound was purified by sublimation at 350 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 10 Instead of using 5.0 g (0.014 mol) of 9,9-bis (trimethylsilyl) fluoren-2-ylboric acid in [4] of Example 1, 9,9-bis (tert-butyl) According to the operation described in [4] of Example 1 except that 6.1 g (0.014 mmol) of (dimethylsilyl) fluoren-2-ylboric acid was used, 4.3 g of Exemplified Compound 10 was obtained. Further, this compound was purified by sublimation at 410 ° C. and 2 × 10 ⁻⁴ Pa.

Preparation of Exemplified Compound 13 Instead of using 5.0 g (0.014 mol) of 9,9-bis (trimethylsilyl) fluoren-2-ylboric acid in [4] of Example 1, 9,9-bis (cyclohexyldimethylsilyl) ) According to the operation described in [4] of Example 1 except that 6.9 g (0.014 mol) of fluoren-2-yl boric acid was used, 4.5 g of Exemplified Compound 13 was obtained. Further, this compound was purified by sublimation at 420 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 19 Instead of using 5.0 g (0.014 mol) of 9,9-bis (trimethylsilyl) fluoren-2-ylboric acid in [4] of Example 1, 9,9-bis (phenyldimethylsilyl) ) 4.6 g of Exemplified Compound 19 was obtained according to the procedure described in [4] of Example 1 except that 6.7 g (0.014 mol) of fluoren-2-yl boric acid was used. Further, this compound was purified by sublimation at 440 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 24 Instead of using 4.6 g (0.012 mol) of 9-bromo-10- (2-naphthyl) anthracene in [4] of Example 1, 4.0 g of 9-bromo-10-phenylanthracene ( Except for using 0.012 mol), 3.2 g of Exemplified Compound 24 was obtained according to the procedure described in [4] of Example 1. Further, this compound was purified by sublimation at 400 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 38 Instead of using 4.6 g (0.012 mol) of 9-bromo-10- (2-naphthyl) anthracene in [4] of Example 1, 9-bromo-10- (phenanthrene-9- Yl) Except that 5.2 g (0.012 mol) of anthracene was used, 4.8 g of Exemplified Compound 38 was obtained according to the procedure described in [4] of Example 1. Further, this compound was purified by sublimation at 430 ° C. and 2 × 10 ⁻⁴ Pa.

Production of Exemplified Compound 48 Instead of using 4.6 g (0.012 mol) of 9-bromo-10- (2-naphthyl) anthracene in [4] of Example 1, 9-bromo-10- (9 ′, 9 According to the operation described in [4] of Example 1 except that 5.4 g (0.012 mol) of '-dimethylfluoren-2-yl) anthracene was used, 3.5 g of Exemplified Compound 48 was obtained. Further, this compound was purified by sublimation at 380 ° 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 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′-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 deposited at a deposition rate of 2.0 nm / sec and 0.02 to 0.1 nm / sec to a thickness of 40 nm to form a light emitting layer, and tris (8-quinolinolate) was formed on the light emitting layer. ) Aluminum was vapor deposited at a deposition rate of 0.2 nm / sec to a thickness of 15 nm to form an electron injecting and transporting layer, and further, magnesium and silver as a cathode were deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm Co-evaporation (Weight ratio 10: 1) was used as a cathode to produce an organic electroluminescent device, and the deposition was carried out while maintaining the reduced pressure state of the vapor deposition tank. It was continuously driven at a constant current density of 10 mA / cm ^{2 in} a dry atmosphere at 25 ° C. Initially, the voltage value was 5.9 V, and blue light emission with a luminance of 970 cd / m ² was confirmed. The half life was 2300 hours.

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8 except that Exemplified Compound 10 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 1 (Table 1).

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8 except that Exemplified Compound 13 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 1 (Table 1).

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8 except that Exemplified Compound 19 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 1 (Table 1).

  In Example 8, when the light emitting layer was formed, an organic electroluminescent device was prepared according to the procedure described in Example 8, except that Exemplified Compound 24 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 1 (Table 1).

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8, except that Exemplified Compound 38 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 1 (Table 1).

  In Example 8, an organic electroluminescent device was prepared according to the procedure described in Example 8, except that Exemplified Compound 48 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 1 (Table 1).

(Comparative Example 1):
In Example 8, the procedure described in Example 8 was followed except that 4,4′-bis (2 ″, 2 ″ -diphenylvinyl) biphenyl 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 1 (Table 1).

(Comparative Example 2):
In Example 8, an organic electroluminescent device was produced according to the procedure described in Example 8 except that 9,10-diphenylanthracene was used instead of Example Compound 1 in forming the light emitting layer. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

(Comparative Example 3):
In Example 8, the formation of the light emitting layer was described in Example 8 except that instead of using Exemplified Compound 1, 9- (9,9-dimethylfluoren-2-yl) -10-phenylanthracene was used. An organic electroluminescent element was prepared according to the above procedure. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

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 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. Initially, blue light emission of 6.0 V and luminance of 950 cd / m ² was confirmed. The half life of luminance was 2150 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. Further, the exemplified compound 10 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 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. Initially, blue light emission of 6.2 V and luminance of 970 cd / m ² was confirmed. The half life of luminance was 1990 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, Example Compound 48 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, 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. While maintaining the reduced pressure state, magnesium and silver were further co-deposited as a cathode to a thickness of 200 nm at a deposition rate of 0.2 nm / sec (weight ratio 10: 1) to form a cathode, and an organic electroluminescent device Was made.

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. Initially, yellow light emission of 6.0 V and luminance of 990 cd / m ² was confirmed. The half life of luminance was 2000 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 48 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 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. Initially, yellow light emission of 6.1 V and luminance of 940 cd / m ² was confirmed. The luminance half-life was 2200 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, 40 nm hole injection transport is performed by spin coating using a 3 mass% 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 an organic electroluminescent device.

When a DC voltage of 10 V was applied to the produced organic electroluminescence device in a dry atmosphere, a current of 92 mA / cm ² flowed. Green light emission with a luminance of 830 cd / m ² was confirmed. The luminance half-life was 420 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 54 and Exemplified Compound 48, and Tris (8-quinolinolato) aluminum are respectively in a weight ratio of 100: 50: 0.5. A 100 nm light emitting layer was formed by spin coating using the contained 3% by mass dichloroethane solution. 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-deposited at a deposition rate of 0.2 nm / sec to a thickness of 200 nm as a cathode (weight ratio 10: 1) to form a cathode, and an organic electroluminescent device was produced.

When a DC voltage of 15 V was applied to the produced organic electroluminescent element in a dry atmosphere, a current of 92 mA / cm ² flowed. Green light emission with a luminance of 980 cd / m ² was confirmed. The half life of luminance was 580 hours.

According to the present invention, it is possible to provide a novel fluorene compound and an organic electroluminescence device using the fluorene compound, having 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 (10)

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

[Wherein, R ^{1 to} R ⁶ are each independently a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl. Represents a group, and R ^{1 to} R ⁶ may be bonded to each other to form a ring.
A represents an anthracenediyl group.
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 It represents an aryl group or a substituted or unsubstituted aralkyl group, and Z ^{1 to} Z ⁶ may be bonded to each other to form a ring. ] The fluorene compound according to claim 1, wherein Z ⁸ is a hydrogen atom, a halogen atom, a substituted or unsubstituted amino group, or a substituted or unsubstituted aryl group. The fluorene compound according to claim 1, wherein Z ⁸ is a substituted or unsubstituted aryl group. The fluorene compound according to claim 1, wherein A is an anthracene-9,10-diyl group and Z ⁸ is a substituted or unsubstituted aryl group. The fluorene compound according to claim 4, wherein Z ⁸ is a substituted or unsubstituted fluoren-2-yl group. An organic electroluminescence device comprising at least one layer containing at least one fluorene compound represented by the general formula (1) according to claim 1 interposed between a pair of electrodes.   The organic electroluminescent element according to claim 6, wherein the layer containing the fluorene compound represented by the general formula (1) is a light emitting layer.   The organic electroluminescence device according to claim 6, wherein the layer containing the fluorene compound represented by the general formula (1) is a charge injection transport layer.   The organic electroluminescent element according to claim 6, further comprising a hole injecting and transporting layer between the pair of electrodes.   The organic electroluminescent element according to claim 6, further comprising an electron injecting and transporting layer between the pair of electrodes.

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