JP2005289921A - Anthracene compound and organic electroluminescent element containing the compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new anthracene compound suitably usable as a luminescent material of an organic electroluminescent element; and an organic electroluminescent element using the compound. <P>SOLUTION: The anthracene compound is represented by formula (1) [wherein Y<SB>1</SB>-Y<SB>10</SB>are each hydrogen, a halogen, or the like, provided that each of Y<SB>1</SB>-Y<SB>10</SB>may form a ring with its adjacent group and that at least one of Y<SB>1</SB>-Y<SB>10</SB>is a group represented by formula (2) (wherein X is oxygen, sulfur, or -N(R)-; and R<SB>1</SB>, R<SB>2</SB>, and R are each hydrogen, a halogen, or the like)]. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

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

Conventionally, an inorganic electroluminescent element has been used as a panel-type light source such as a backlight. However, in order to drive the light emitting element, an alternating high voltage is required. Recently, an organic electroluminescence device (organic electroluminescence device: organic EL device) using an organic material as a luminescent material has been developed [see, for example, Non-Patent Document 1].
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, and electrons and holes are injected into the thin film and recombined to form an exciton (exington). ) And emits light using light emitted when the exciton is deactivated. The organic electroluminescent element can emit light at a low direct current voltage of several volts to several tens of volts, and various colors (for example, red, blue, green) can be selected by selecting the type of the fluorescent organic compound. ) Can be emitted. The organic electroluminescent element having such characteristics is expected to be applied to various light emitting elements, display elements and the like. However, in general, the luminance is low, which is not sufficient for practical use.
As a method for improving the light emission luminance, an organic electroluminescent element using tris (8-quinolinolato) aluminum as a host material and a coumarin derivative or a pyran derivative as a guest compound (dopant) has been proposed as a light emitting layer. [See Non-Patent Document 2]. In addition, organic electroluminescent elements using anthracene derivatives as the material of the light emitting layer have been proposed (see, for example, Patent Document 1 and Patent Document 2). Furthermore, an organic electroluminescent element using an anthracene derivative as a guest compound of the light emitting layer has also been proposed (see, for example, Patent Document 3 and Patent Document 4).
However, it cannot be said that these light emitting elements also have sufficient light emission luminance and light emission lifetime, and at present, further higher luminance and longer life are desired.
Appl.Phys.lett., 51,913 (1987) J. Appl. Phys., 65, 3610 (1989) JP-A-8-12600 JP-A-11-111458 Japanese Patent Laid-Open No. 10-36832 JP-A-10-294179

  An object of the present invention is to provide a novel anthracene compound. More specifically, for example, it is to provide an anthracene compound that can be suitably used as a light-emitting material of an organic electroluminescent element. Another object of the present invention is to provide an organic electroluminescence device using the compound.

In order to solve the above-mentioned problems, the present inventors have intensively studied various anthracene compounds, in particular, anthracene compounds that can be suitably used as a light-emitting material of an organic electroluminescent device, and as a result, the present invention has been completed. It was. That is, the present invention
<1> relates to an anthracene compound represented by the formula (1),

[In the formula (1), Y _{1 to} Y ₁₀ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an ester group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, or an aralkyloxy group. A group, an aryl group or an aryloxy group, and the adjacent groups of Y _{1 to} Y ₁₀ may form a ring together with the adjacent groups, and at least one of Y _{1 to} Y ₁₀ is represented by the formula (2 Is a group represented by

[In the formula (2), X represents an oxygen atom, a sulfur atom or —N (R) —, and R ₁ , R ₂ and R each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, It represents an ester group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, an aralkyloxy group, an aryl group or an aryloxy group. ]

As a preferred embodiment,
<2>: An anthracene compound according to <1>, wherein in formula (1), at least one of Y ₉ and Y ₁₀ is a group represented by formula (2),
<3>: Anthracene compound according to <1> represented by the following formula (3):

In [Equation _(3), Y 1 to Y ₉ is the same atom or group as in formula _(1), adjacent groups of Y 1 to Y ₉ are also form a ring with each adjacent group Good. X, R ₁ and R ₂ represent the same atom or group as in formula (2). ]
<4>: The anthracene compound according to <1> represented by the following formula (4):

In [Equation _(4), Y 1 to Y ₈ are the same atom or group as in formula _(1), adjacent groups of Y 1 to Y ₈ are also form a ring with each adjacent group Good. X, R ₁ and R ₂ represent the same atom or group as in formula (2). ]
It is about.

In addition, the present invention
<5>: An organic electroluminescence device comprising at least one layer containing at least one anthracene compound represented by formula (1) between a pair of electrodes,
As a preferred embodiment,
<6>: The organic electroluminescent element according to <5>, wherein the layer containing the anthracene compound represented by the formula (1) is a light emitting layer.
<7>: The organic electroluminescence device according to <5>, wherein the layer containing the anthracene compound represented by the formula (1) is a hole injection transport layer,
<8>: The organic electroluminescence device according to any one of <5> to <7>, further comprising a hole injection transport layer between the pair of electrodes.
<9>: The organic electroluminescence device according to any one of <5> to <8>, further having an electron injection / transport layer between the pair of electrodes.
It is about.

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

  Hereinafter, the present invention will be described in detail.

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

[In the formula (1), Y _{1 to} Y ₁₀ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an ester group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, or an aralkyloxy group. A group, an aryl group or an aryloxy group, and the adjacent groups of Y _{1 to} Y ₁₀ may form a ring together with the adjacent groups, and at least one of Y _{1 to} Y ₁₀ is represented by the formula (2 Is a group represented by

[In the formula (2), X represents an oxygen atom, a sulfur atom or —N (R) —, and R ₁ , R ₂ and R each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, It represents an ester group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, an aralkyloxy group, an aryl group or an aryloxy group. ]
A preferred embodiment of the anthracene compound of the present invention includes a compound in which at least one of Y ₉ and Y _{10 in} the formula (1) is a group represented by the formula (2). More preferred specific embodiments include the compound of formula (3), and more preferred specific embodiments include the compound of formula (4).

In the anthracene compounds represented by the formulas (1), (3), and (4), Y _{1 to} Y ₁₀ are each independently a hydrogen atom or a halogen atom, a cyano group, a nitro group, an amino group, an ester group, or an alkylcarbonyl group. Represents an alkyl group, an alkoxy group, an aralkyl group, an aralkyloxy group, an aryl group or an aryloxy group. In this case, an amino group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, an aralkyloxy group, an aryl group, and an aryloxy group include a substituted or unsubstituted amino group, a linear, branched, or cyclic alkyl group, respectively. Carbonyl group, linear, branched or cyclic alkyl group, linear, branched or cyclic alkoxy group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aralkyloxy group, substituted or unsubstituted aryl group, substituted or unsubstituted Substituted aryloxy groups are included (hereinafter the same). The adjacent groups of Y _{1 to} Y ₁₀ may form a ring together with the adjacent groups.
Y _{1 to} Y ₁₀ are preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an ester group, an alkylcarbonyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or 1 carbon atom. Represents an alkoxy group having 10 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aralkyloxy group having 7 to 20 carbon atoms, an aryl group having 4 to 20 carbon atoms, or an aryloxy group having 4 to 20 carbon atoms, more preferably Hydrogen atom, halogen atom, cyano group, nitro group, amino group, alkylcarbonyl group having 1 to 8 carbon atoms, alkyl group having 1 to 8 carbon atoms, alkoxy group having 1 to 8 carbon atoms, aralkyl having 7 to 16 carbon atoms Group, an aralkyloxy group having 7 to 16 carbon atoms, an aryl group having 4 to 16 carbon atoms, or an aryloxy group having 4 to 16 carbon atoms. Here, the aryl group represents a carbocyclic aromatic group and a heterocyclic aromatic group.

In the anthracene compound represented by the formula (1) of the present invention, at least one of Y _{1 to} Y ₁₀ is a group represented by the formula (2).

[In the formula (2), X represents an oxygen atom, a sulfur atom or —N (R) —, and R ₁ , R ₂ and R each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, It represents an ester group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, an aralkyloxy group, an aryl group or an aryloxy group. ]
Specific examples of the halogen atom represented by Y _{1 to} Y ₁₀ include a fluorine atom, a chlorine atom, and a bromine atom.

Specific examples of the amino group of Y _{1 to} Y ₁₀ include an unsubstituted amino group, an N-methylamino group, an N-ethylamino group, an Nn-propylamino group, an N-isopropylamino group, and an Nn-butyl group. Amino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, Nn-pentylamino group, N-cyclopentylamino group, Nn-hexylamino group, N-cyclohexyl Amino 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, -(2-anthranyl) amino group, N- (9-anthranyl) amino group, N-carbazolyl group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-propylamino group N, N-di-isopropylamino group, N, N-di-n-butylamino group, N, N-di-isobutylamino group, N, N-di-sec-butylamino group, N, N-di -N-pentylamino group, N, N-dicyclopentylamino group, N, N-dicyclohexylamino group, N, N-dibenzylamino group, N, N-diphenethylamino group, N-methyl-N-ethylamino Group, N-methyl-Nn-propylamino group, N-methyl-N-isopropylamino group, N-methyl-Nn-butylamino group, N-methyl-N-tert-butylamino group, N- Methyl-N-cyclope Chiruamino 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 and the like can be mentioned.

Specific examples of the ester group of Y _{1 to} Y ₁₀ include methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, isopropyloxycarbonyl group, n-butyloxycarbonyl group, isobutyloxycarbonyl group, tert-butyloxy Carbonyl group, n-pentyloxycarbonyl group, cyclopentyloxycarbonyl group, cyclohexyloxycarbonyl group, benzyloxycarbonyl group, phenyloxycarbonyl group, 1-naphthyloxycarbonyl group, 2-naphthyloxycarbonyl group,
Acetyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, n-butylcarbonyloxy group, tert-butylcarbonyloxy group, cyclohexylcarbonyloxy group, benzylcarbonyloxy group, phenylcarbonyloxy group, 1-naphthylcarbonyloxy Group, 2-naphthylcarbonyloxy group and the like.

Specific examples of the alkylcarbonyl group represented by Y _{1 to} Y ₁₀ include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an isopropylcarbonyl group, an n-butylcarbonyl group, a tert-butylcarbonyl group, and an n-pentylcarbonyl group. , Cyclopentylcarbonyl group, n-hexylcarbonyl group, cyclohexylcarbonyl group, n-heptylcarbonyl group, n-octylcarbonyl group, n-nonylcarbonyl group, n-decylcarbonyl group and the like.

Specific examples of the alkyl group represented by Y _{1 to} Y ₁₀ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, and 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, -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, isobornel 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-methyl Cyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2 , 4,6-trime Rucyclohexyl group, 3,3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4-tert-butylcyclohexyl group, 3-tert-butylcyclohexyl group, 4-phenylcyclohexyl group, 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, 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-dodecyloxyethyl group, 2-n-tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxy Propyl group, 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-he Sill oxy-butyl group,

4-n-octyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl 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-isopropyloxidedecyl 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-allyl Oxyethyl group, 2- (4-pentenyloxy) ethyl group, 3-allyloxypropyl group, 3- (2-hexenyloxy) propyl group, 3- (2-heptenyloxy) propyl group, 3- (1-cyclohexenyl) Oxy) 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-fluorobenzyl) Oxy) ethyl group, 2- (4-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4-methoxybenzyloxy) propyl group, 4-benzyloxybutyl group, 2- (benzyloxymethoxy) An ethyl group, a 2- (4-methylbenzyloxymethoxy) ethyl group,

Phenyloxymethyl group, 4-methylphenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-fluorophenyloxymethyl group, 4-chlorophenyloxymethyl group Group, 2-chlorophenyloxymethyl 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-phenyl Oxypropyl group, 3- (2-naphthyloxy) propyl group, 4-phenyloxybut Group, 4- (2-ethylphenyloxy) butyl group, 5- (4-tert-butylphenyloxy) pentyl group, 6- (2-chlorophenyloxy) hexyl group, 8-phenyloxyoctyl group, 10-phenyl Oxydecyl 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, 2-base Jiruchioechiru group, 3- (4-methylbenzyl-thio) propyl group, 4-benzyl-thio-butyl group, 2- (2-benzyloxy-ethyl thio) ethyl group, 3- (3-benzyl thio propyl thio) 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, trifluoromethyl 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, 6-fluorohexyl group, 4-fluorocyclohexyl group, 1,1-dihydro-perfluoro-n-octyl group, 1,1- Hydro-perfluoro-n-decyl group, 1,1-dihydro-perfluoro-n-dodecyl group, 1,1-dihydro-perfluoro-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-trichloro Ethyl 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- Examples thereof include a hydroxydecyl group, a 12-hydroxydodecyl group, and a 2-hydroxycyclohexyl group.

Specific examples of the alkoxy group represented by Y _{1 to} Y ₁₀ include an alkoxy group represented by a form in which an oxygen atom is bonded to the above alkyl group.

Specific examples of the aralkyl group represented by Y _{1 to} Y ₁₀ include 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-methylbenzyl 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-phenethylbenzyl group, 4-phenylbenzyl group, 4- (4-methylpheny group) ) Benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxy benzyl group, 4-n-butoxybenzyl group, 4-n-heptyloxy benzyl 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, 4
-Hydroxy-3-methoxybenzyl group, 4-fluorobenzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group, 2-chlorobenzyl group, 3,4-dichlorobenzyl group, 2-furfuryl Group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group and the like.

Specific examples of the aralkyloxy group represented by Y _{1 to} Y ₁₀ include an aralkyloxy group represented by a form in which an oxygen atom is bonded to the above aralkyl group.

Specific examples of the aryl group represented by Y _{1 to} Y ₁₀ include, for example, a phenyl group, 1-naphthyl group, 2-naphthyl group, 2-phenyl-6-naphthyl group, 2-anthracenyl group, 9-anthracenyl group, 10- Phenylanthracen-9-yl group, 9-phenanthrenyl group, fluorenyl group, 9,9-dimethyl-9H-fluoren-2-yl group, 4-quinolyl group, 5-pyridyl group, 4-pyridyl group, 3-pyridyl group 2-pyridyl group, 2-pyrimidyl group, 4-pyrimidyl group, 5-pyrimidyl group, 2-pyridazinyl group, 2-pyrazinyl group, 3-furyl group, 2-furyl group, 3-thienyl group, 2-thienyl group 2-oxazolyl group, 2-thiazolyl group, 2-benzoxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl 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,
2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2, 3,5-trimethylphenyl group, 3,4,5-trimethylphenyl group, 2,4-diethylphenyl group, 2,3,6-trimethylphenyl group, 2,4,6-trimethylphenyl group, 2,6- Diethylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 3,5-di- tert-butylphenyl group, 2,4-dineopentylphenyl group, 2,5-di-tert-pentylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl- 2 Methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 2,3,5,6-tetramethyl-phenyl 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-isopropyloxy Phenyl group, 4-n-butyloxyphenyl group, 4-isobutyloxyphenyl group, 2-isobutyloxyphenyl group, 2-sec-butyloxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl Group, 2-isopentyloxyphenyl 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- - tetradecyloxyphenyl group, 4-n-hexadecyl oxyphenyl group, 4-n-octadecyloxyphenyl group, 4-cyclohexyloxy-phenyl group, 2-cyclohexyloxy-phenyl 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-methoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group,

4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group, 2-bromophenyl group, 4-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-trichloroph Group, 2,3,6-bromophenyl 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- Methoxyphenyl 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-allylphenyl 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-methoxy-3-phenylphenyl 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, 6-benzyloxy-2 -Naphthyl group, 6- (4-methylbenzyloxy) -2-naphthyl group, 7-benzyloxy-2-naphthyl group, 4- (benzyloxymethyl) phenyl group, 4- (2-benzyloxyethyloxy) phenyl Group,

4-phenyloxyphenyl group, 3-phenyloxyphenyl group, 2-phenyloxyphenyl group, 4- (4-methylphenyloxy) phenyl group, 4- (4-methoxyphenyloxy) phenyl group, 4- (4- Chlorophenyloxy) phenyl group, 4-phenyloxy-1-naphthyl group, 6-phenyloxy-2-naphthyl group, 7-phenyloxy-2-naphthyl group, 4-phenyloxymethylphenyl group, 4- (2-phenyl) Oxyethoxy) phenyl group, 4- [2- (4-methylphenyloxy) ethoxy] phenyl group, 4- [2- (4-methoxyphenyloxy) ethoxy] phenyl group, 4- [2- (4-chlorophenyloxy) ) Ethoxy] phenyl group,
4-acetylphenyl group, 3-acetylphenyl group, 2-acetylphenyl group, 4-ethylcarbonylphenyl group, 2-ethylcarbonylphenyl group, 4-n-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-allylcarbonyl Phenyl group, 4-benzylcarbonylphenyl group, 4- (4-methylbenzyl) carbonylphenyl group, 4-phenylcarbonylphenyl group, 4- (4-methylphenyl) carbonylphenyl group, 4- (4-chlorophenyl) carbonylphenyl The group 4-phenylcarbonyl-1-naphth Group,

4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-n-propyloxycarbonylphenyl group, 4-n-butyloxycarbonylphenyl group, 4- n-hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonyl-1-naphthyl group, 6-methoxycarbonyl-2-naphthyl group, 6-n- Butyloxycarbonyl-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) oxy A carbonylphenyl group, a 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-butylcarbonyloxy -1-naphthyl group, 5-acetyloxy-1-naphthyl group, 6-ethylcarbonyloxy-2-naphthyl group, 7-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4-benzylcarbonyloxy Phenyl group 4- phenethyl carbonyloxy phenyl group, 6-benzyloxy carbonyloxy-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-isobutylthiophenyl group, 2-neopentylthiophenyl group, 4-n-hexylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group,

4-benzylthiophenyl group, 3-benzylthiophenyl group, 2-benzylthiophenyl group, 4- (4-chlorobenzylthio) phenyl group, 4-phenylthiophenyl group, 3-phenylthiophenyl group, 2-phenyl Thiophenyl 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-formyl Phenyl group, 4-formyl-1-naphthyl group, 1-formyl-2-naphthyl group,

4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morpholinophenyl group, 4- (N-ethylpiperazino) 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 N-cyclohexyl-N-methylamino) phenyl group, 4- (N, N-diethylamino) -1-naphthyl group, 4- (N-benzyl-N-phenylamino) phenyl group, 4- (N, N-diphenyl) Amino) phenyl group, 4- [N-phenyl-N- (4-methylphenyl) amino] phenyl group, 4- [N-phenyl-N- (1-naphthyl) amino] phenyl group, 4- [N, N -Di (3-methylphenol L) 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- (4-N, N-dimethylaminophenyl) -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, etc. Rukoto can.

Specific examples of the aryloxy group represented by Y _{1 to} Y ₁₀ include an aryloxy group represented by a form in which an oxygen atom is bonded to the above aryl group.

In the formulas (2), (3) and (4), R ₁ , R ₂ and R are a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an ester group, an alkylcarbonyl group, an alkyl group or an alkoxy group. Represents an aralkyl group, an aralkyloxy group, an aryl group or an aryloxy group. In this case, an amino group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, an aralkyloxy group, an aryl group, and an aryloxy group include a substituted or unsubstituted amino group, linear, branched, or cyclic alkyl, respectively. Carbonyl group, linear, branched or cyclic alkyl group, linear, branched or cyclic alkoxy group, substituted or unsubstituted aralkyl group, substituted or unsubstituted aralkyloxy group, substituted or unsubstituted aryl group, substituted or Unsubstituted aryloxy groups are included (hereinafter the same).

R ₁ , R ₂ and R are preferably a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an ester group, an alkylcarbonyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, carbon Represents an alkoxy group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aralkyloxy group having 7 to 20 carbon atoms, an aryl group having 4 to 20 carbon atoms, or an aryloxy group having 4 to 20 carbon atoms, more preferably Is a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an alkylcarbonyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or 7 to 16 carbon atoms. A aralkyl group having 7 to 16 carbon atoms, an aryl group having 4 to 16 carbon atoms, or an aryloxy group having 4 to 16 carbon atoms. Here, the aryl group represents a carbocyclic aromatic group and a heterocyclic aromatic group.

Specific examples of the halogen atoms for R ₁ , R ₂ and R include the halogen atoms listed as specific examples of the halogen atoms for Y _{1 to} Y ₁₀ .

Specific examples of the amino groups of R ₁ , R ₂ and R include the amino groups mentioned as specific examples of the amino groups of Y _{1 to} Y ₁₀ .

Specific examples of the ester groups of R ₁ , R ₂ and R include the ester groups mentioned as specific examples of the ester groups of Y _{1 to} Y ₁₀ .

Specific examples of the alkylcarbonyl group for R ₁ , R ₂ and R include the alkylcarbonyl groups mentioned as specific examples of the alkylcarbonyl group for Y _{1 to} Y ₁₀ .

Specific examples of the alkyl group of R ₁ , R ₂ and R include the alkyl groups mentioned as specific examples of the alkyl group of Y _{1 to} Y ₁₀ .

Specific examples of the alkoxy group represented by R ₁ , R ₂ and R include an alkoxy group represented by a form in which an oxygen atom is bonded to the alkyl group exemplified as a specific example of the alkyl group represented by Y _{1 to} Y _10. .

Specific examples of R ₁ , R ₂ and R aralkyl groups include the aralkyl groups mentioned as specific examples of Y _{1 to} Y ₁₀ aralkyl groups.

Specific examples of the aralkyloxy group for R ₁ , R ₂ and R include an aralkyloxy group represented by a form in which an oxygen atom is bonded to the aralkyl group listed as specific examples of the aralkyl groups of Y _{1 to} Y _10. Can do.

Specific examples of the aryl group for R ₁ , R ₂ and R include the aryl groups mentioned as specific examples of the aryl group for Y _{1 to} Y ₁₀ .

Specific examples of the aryloxy group for R ₁ , R ₂ and R include an aryloxy group represented by a form in which an oxygen atom is bonded to the aryl group mentioned as a specific example of the aryl group for Y _{1 to} Y _10. Can do.

  Specific examples of the anthracene compound represented by the formula (1) according to the present invention include the following compounds (Chemical Formulas 12 to 50), but the present invention is not limited thereto. Absent.

The anthracene compound represented by the formula (1) of the present invention can be produced by, for example, the following steps.
[Production of anthracene compound (1-A) in which Y ₉ and Y ₁₀ are groups represented by formula (2) in formula (1) (Chemical Formula 51)]

[Wherein Y _{1 to} Y ₈ , X, R ₁ , R ₂ represent the same atom or group as in formula (1) and formula (2), and L ₁ and L ₂ represent a halogen atom, an arylsulfonyloxy group, and Represents a leaving group such as a trifluoromethanesulfonyloxy group)
An anthracene derivative represented by the formula (A) and a boronic acid derivative represented by 2 moles of the formula (B) are converted into a palladium catalyst [for example, tetrakis (triphenylphosphine) palladium, palladium acetate / tri-tert-butylphosphine. ] And a base (for example, organic bases such as triethylamine and pyridine, inorganic bases such as sodium carbonate and potassium carbonate) in the formula (1), Y ₉ and Y ₁₀ are represented by the formula (2). An anthracene compound (1-A) which is a group to be produced can be produced.
[Production of anthracene compound (1-B) in which Y ₉ is a group represented by formula (2) and Y ₁₀ is an alkyl group, an aralkyl group, or an aryl group (formula 52)]

[Wherein Y _{1 to} Y ₈ , X, R ₁ and R ₂ represent the same atom or group as in formula (1) and formula (2), Y ₁₀ represents an alkyl group, an aralkyl group or an aryl group, L ₁ and L ₂ represent a leaving group such as a halogen atom]
An anthracene compound represented by the formula (C) and a Grignard reagent represented by the formula (D) are converted into an iron catalyst (for example, tris (acetylacetonato) iron) or a nickel catalyst (for example, [1,3-bis (Diphenylphosphino) propane] nickel dichloride, etc.) to produce a compound represented by the formula (E) and then a halogenating agent (for example, N-bromosuccinimide, N-iodosuccinimide) To produce an anthracene derivative represented by the formula (F). Further, by reacting the anthracene derivative represented by the formula (F) and the boronic acid derivative represented by the formula (B) in the presence of a palladium catalyst and a base, Y ₉ is represented by the formula (2) in the formula (1). And an anthracene compound (1-B) in which Y ₁₀ is an alkyl group, an aralkyl group, or an aryl group.

The anthracene compound represented by the formula (C) is, for example, Y ₉ or Y ₁₀ in the formula (1).
Is a hydrogen atom and an equimolar halogenating agent (for example, N-bromosuccinimide, N-iodosuccinimide).
[Production of anthracene compound (1-B ′) in which Y ₁₀ is a group represented by formula (2) and Y ₉ is an amino group, an alkoxy group, an aralkyloxy group or an aryloxy group in formula (1) (Chemical Formula 53)]

[Wherein Y _{1 to} Y ₈ , X, R ₁ and R ₂ represent the same atom or group as in formula (1) and formula (2), and Y ₉ represents an amino group, an alkoxy group, an aralkyloxy group or an aryl group. Represents an oxy group, and L ₁ represents a leaving group such as a halogen atom]
An anthracene derivative represented by the formula (C) and a boronic acid derivative represented by the formula (B) are converted into a palladium catalyst [eg, tetrakis (triphenylphosphine) palladium, palladium acetate / tri-tert-butylphosphine] and a base. (For example, an organic base such as triethylamine or pyridine, or an inorganic base such as sodium carbonate or potassium carbonate) to produce an anthracene derivative represented by the formula (G), and then a halogenating agent (for example, N-bromosuccinimide and N-iodosuccinimide) are halogenated to produce an anthracene derivative represented by formula (H), and then a compound represented by formula (I) (wherein Y ₉ is an amino group, alkoxy In formula (1) by acting a group, aralkyloxy group or aryloxy group) _An anthracene compound (1-B ′) in which ₁₀ is a group represented by the formula (2) and Y ₉ is an amino group, an alkoxy group, an aralkyloxy group, or an aryloxy group can be produced. In addition, the compound represented by Formula (G) corresponds to the compound in which Y ₉ is a hydrogen atom in Formula (3), and the compound in which L _{1 in} Formula (H) is a halogen atom is in Formula (3). , Y ₉ corresponds to a halogen atom.

  The reaction between the anthracene derivative represented by the formula (H) and the compound represented by the formula (I) includes [1] an anthracene derivative represented by the formula (H), a compound represented by the formula (I), , In the presence of a copper catalyst (for example, copper powder, copper chloride, copper bromide), optionally using a polar solvent (for example, o-dichlorobenzene, sulfolane) as a solvent, [2] represented by formula (H) An anthracene derivative and a compound represented by the formula (I) are reacted with a palladium catalyst [for example, palladium acetate / tri-tert-butylphosphine, palladium acetate / triphenylphosphine, tris (dibenzylideneacetone) dipalladium / tri -Tert-butylphosphine] and a base (for example, sodium-tert-butoxide, potassium-tert-butoxide, sodium carbonate, potassium carbonate) It can be implemented by law.

  Next, the organic electroluminescent element of the present invention will be described.

  The organic electroluminescent element of the present invention comprises at least one layer containing at least one anthracene compound represented by the formula (1) between a pair of electrodes. When the layer containing the anthracene compound is a light emitting layer, the layer containing the anthracene compound is preferably a hole injection transport layer, and the layer containing the anthracene compound is more preferably a light emitting layer.

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

  In the organic electroluminescent element of the present invention, the anthracene compound represented by the 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 injection / transport layer / electron injection / transport layer / light-emitting layer / electron injection / transport layer / cathode-type device (FIG. 5) in which the light-emitting layer is sandwiched between electron injection / transport layers. You can also. In addition, the (EL-4) type element structure is an element of a type in which a light emitting component is sandwiched between a pair of electrodes as a light emitting layer, that is, (EL-6) a hole injecting and transporting component as a light emitting layer. A device of a type sandwiched between a pair of electrodes in a single layer form in which a light emitting component and an electron injection component are mixed (FIG. 6), (EL-7) A hole injection transport component and a light emitting component are mixed as a light emitting layer. An element of a type sandwiched between a pair of electrodes in a single layer form (FIG. 7), (EL-8) a type of 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 the elements (FIG. 8) may be used.

  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. In each type of device, a light emitting component is provided between the hole injecting and transporting layer and the light emitting layer, a mixed layer of the hole injecting and transporting component and the light emitting component, and / or between the light emitting layer and the electron injecting and transporting layer. 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 is preferably a transparent or translucent substrate, 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. A substrate made of a translucent plastic sheet, quartz, transparent ceramics, or a composite sheet combining these 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, an alloy or a conductive compound having a relatively large work function as an electrode material. Examples of the electrode material used for the anode include gold, platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In ₂ O ₃ ), tin oxide (SnO ₂ ), zinc oxide, ITO ( Indium tin oxide (Indium Tin Oxide), polythiophene, polypyrrole, etc. can be mentioned. These electrode materials may be used alone or in combination. For the anode, these electrode materials can be formed on the substrate by a method such as vapor deposition or sputtering. Further, the anode may have a single layer structure or a multilayer structure. The sheet electrical resistance of the anode is preferably set to several hundred Ω or less, more preferably about 5 to 50 Ω. The thickness of the anode is generally about 5 to 1000 nm, more preferably about 10 to 500 nm, although it depends on the material of the electrode material used.
The hole injection transport layer 3 is a layer containing a compound having a function of facilitating the injection of holes from the anode and a function of transporting the injected holes. The hole injecting and transporting layer may be an anthracene compound represented by the formula (1) or another compound having a hole injecting and transporting function (for example, phthalocyanine derivatives, triarylamine derivatives, triarylmethane derivatives, oxazole derivatives, hydrazone derivatives). , Stilbene derivatives, pyrazoline derivatives, polysilane derivatives, polyphenylene vinylene and derivatives thereof, polythiophene and derivatives thereof, poly-N-vinylcarbazole, 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 an anthracene compound represented by the formula (1) in the hole injection transport layer. Examples of the compound having a hole injecting and transporting function other than the anthracene compound represented by the 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] biphenyl, 4,4'-bis [N-phenyl-N- (3-methylphenyl) amino] biphenyl, 4,4'-bis [N -Phenyl-N- (3-methoxyphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (1-naphthyl) amino] biphenyl, 3,3'-dimethyl-4,4'-bis [N-phenyl-N- (3-methylphenyl) amino] biphenyl, 4,4′-bis [2- (4-N, N-diphenylaminophenyl) vinyl] biphenyl, 1,1-bis [ -[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′-N, N-di (4-methylphenyl) aminobiphenyl-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-tri (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-tris (4-diphenylamino) phenylbenzene, and the like, polythiophene and derivatives thereof, and poly-N-vinylcarbazole and derivatives thereof are more preferable.

When the anthracene compound represented by the formula (1) and another compound having a hole injection function are used in combination, the content of the anthracene compound represented by the formula (1) in the hole injection / transport layer is preferably 0.1 mass% or more, more preferably 0.5 to 99.9 mass%, still more preferably 3 to 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 may be formed using the anthracene compound represented by the formula (1) as a host material and at least one compound having a light emitting function other than the anthracene compound represented by the formula (1) as a guest material. In addition, a compound having a light emitting function other than the anthracene compound represented by the formula (1) may be used as at least one host material, and the anthracene compound represented by the formula (1) may be used as a guest material. it can.

  Examples of the compound (guest material / host material) having a light emitting function other than the anthracene compound represented by the formula (1) include 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 -Ethynylanthracenyl) 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) Examples of the compound include the above-mentioned compounds), organometallic complexes [for example, tris (8-quinolinolato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, zinc of 2- (2-hydroxyphenyl) benzothiazole Salt, zinc salt of 4-hydroxyacridine, zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivative [eg 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 (for example, Coumarin 1, Coumarin 6, Coumarin 7, Coumarin 30, Coumarin 106, Coumarin 38, coumarin 151, coumarin 152, coumarin 153, coumarin 307, coumarin 311, coumarin 314, coumarin 334, 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 ester derivatives, poly-N-vinylcarbazole and derivatives thereof, polythiophene and derivatives thereof, polyphenylene and derivatives thereof, polyfluorene and derivatives thereof, polyphenylene Vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and its derivatives It can be exemplified a derivative thereof, polythienylenevinylene and derivatives thereof.

Compounds having a light emitting function other than the anthracene compound represented by formula (1) (guest material / host material) include acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallic complexes, and stilbene derivatives. Are preferred, and polycyclic aromatic compounds and organometallic complexes are more preferred.
The organic electroluminescent element of the present invention preferably contains an anthracene compound represented by the formula (1) as a host material in the light emitting layer. When the anthracene compound represented by the formula (1) is used as a host material in combination with another compound having a light emitting function (guest material), the content of the anthracene compound represented by the formula (1) in the light emitting layer is , Preferably, it is 99.9-80 mass%, More preferably, it is 99-90 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 anthracene compound represented by the 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. is there.
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 the organometallic complex include an organoaluminum complex such as tris (8-quinolinolato) aluminum, an organic beryllium complex such as bis (10-benzo [h] quinolinolato) beryllium, a beryllium salt of 5-hydroxyflavone, 5- Examples thereof include an aluminum salt of hydroxyflavone. An organoaluminum complex is preferable, and an organoaluminum complex having an 8-quinolinolato ligand is more preferable. Examples of the organoaluminum complex having an 8-quinolylate ligand include compounds represented by formulas (a) to (c).

(Q) ₃ -Al (a)
(Wherein Q represents an 8-quinolinolate ligand)
(Q) ₂ -Al-OL '(b)
(Wherein Q represents an 8-quinolinolato ligand, OL ′ represents an aryloxy ligand, and L ′ represents an aryl group having 6 to 24 carbon atoms)
(Q) _2- Al-O-Al- (Q) ₂ (c)
(Wherein Q represents an 8-quinolinolate ligand)

Specific examples of the organoaluminum complex having an 8-quinolinolato ligand include, for example, tris (8-quinolinolato) aluminum, tris (4-methyl-8-quinolinolato) aluminum, and 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-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,3-dimethylphenolate) aluminum, Bis (2-methyl-8-quinolinolate) ( , 6-dimethyl phenolate) 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-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,6-diphenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (2 , 4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,4,4 5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (1- Phthalate) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2,4-dimethyl- 8-quinolinolato) (3-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (4-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato) (3,5 -Dimethylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di-tert-butylphenolate) 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. Here, the aryl group of L ′ represents a carbocyclic aromatic group.
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 take out light emitted from the organic electroluminescence device of the present invention with high efficiency, 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. Thus, 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 under a vacuum of about 10 ⁻⁵ Torr or less. Therefore, it is preferable to carry out at a deposition rate of about 0.005 to 50 nm / sec at a boat temperature (deposition source temperature) of about 50 to 500 ° C. and a substrate temperature of about −50 to 300 ° C. 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 (hexane 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. , Tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene,
Halogenated hydrocarbon solvents such as dichlorobenzene and chlorotoluene, ester solvents such as ethyl acetate, butyl acetate, amyl acetate, and ethyl lactate, methanol, propanol, butanol, pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve , Alcohol solvents such as ethylene glycol, ether solvents such as dibutyl ether, tetrahydrofuran, dioxane, dimethoxyethane, anisole, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1, And polar solvents such as 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 in 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 DC drive type element, but can also be used as an AC 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 an 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 7 Composed of 3.89 g (22 mmol) of 2-methylbenzoxazole-5-boronic acid, 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 4.66 g of sodium carbonate, 24 g of toluene and 24 g of water. Under a nitrogen stream, 170 mg of tetrakis (triphenylphosphine) palladium was added to the mixture, heated to 80 ° C., and stirred at the same temperature for 6 hours. The reaction mixture was cooled to room temperature, the toluene phase was separated, washed with water, and toluene was distilled off from the toluene phase under reduced pressure. The residue was purified by silica gel column chromatography and further recrystallized twice from toluene to obtain 3.8 g of the target compound of Exemplified Compound 7 as colorless crystals. Further, this compound was purified by sublimation at 340 ° C. and 2 × 10 ⁻⁴ Pa. Field desorption mass spectrum (FD-MS) m / z = 385

Preparation of Exemplified Compound 10 In Example 1, instead of using 7.33 g (22 mmol) of 10-bromo-9-phenylanthracene, 9.53 g (22 mmol) of 10-bromo-9- (9-phenanthryl) anthracene was used. Except for the above, according to the procedure described in Example 1, 4.1 g of the compound of Exemplified Compound 10 was obtained as colorless crystals. Further, this compound was purified by sublimation at 420 ° C. and 3 × 10 ⁻⁴ Pa.
FD-MS m / z = 485

Preparation of Exemplified Compound 57 To a mixture of 7.79 g (44 mmol) of 2-methylbenzoxazole-5-boronic acid, 7.39 g (22 mmol) of 9,10-dibromoanthracene, 9.32 g of sodium carbonate, 30 g of toluene and 24 g of water Under a nitrogen stream, 340 mg of tetrakis (triphenylphosphine) palladium was added, heated to 80 ° C., and heated and stirred at the same temperature for 6 hours. The reaction mixture was cooled to room temperature, the toluene phase was separated, washed with water, and toluene was distilled off from the toluene phase under reduced pressure. The residue was purified by silica gel column chromatography, and further recrystallized twice from toluene to obtain 3.9 g of the target Compound 57 as a pale yellow crystal. Further, this compound was purified by sublimation at 400 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 440

Preparation of Exemplary Compound 58 In Example 3, instead of using 7.79 g (44 mmol) of 2-methylbenzoxazole-5-boronic acid, 10.52 g of 2-phenylbenzoxazole-5-boronic acid
Except that g (44 mmol) was used, 5.1 g of the compound of Exemplified Compound 58 was obtained as pale yellow crystals according to the procedure described in Example 3. Further, this compound was purified by sublimation at 410 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 564

Preparation of Exemplified Compound 66 In Example 3, instead of using 7.79 g (44 mmol) of 2-methylbenzoxazole-5-boronic acid, 10.52 g (44 mmol) of 2-phenylbenzoxazole-6-boronic acid was used. Except that, according to the procedure described in Example 3, 4.7 g of the compound of Exemplified Compound 66 was obtained as pale yellow crystals. Further, this compound was purified by sublimation at 410 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 564

Production of Exemplified Compound 87 In Example 1, instead of using 3.89 g (22 mmol) of 2-methylbenzoxazole-5-boronic acid, 4.25 g (22 mmol) of 2-methylbenzothiazole-5-boronic acid was used. Except for the above, according to the procedure described in Example 1, 4.1 g of the compound of Exemplified Compound 87 was obtained as colorless crystals. Further, this compound was purified by sublimation at 340 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 401

Production of Exemplified Compound 91 In Example 1, instead of using 3.89 g (22 mmol) of 2-methylbenzoxazole-5-boronic acid, 5.61 g (22 mmol) of 2-phenylbenzothiazole-5-boronic acid was used. 3.9 g of the compound of exemplary compound 91 was obtained as colorless crystals according to the procedures described in Example 1. Further, this compound was purified by sublimation at 360 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 463

Preparation of Exemplified Compound 112 In Example 1, instead of using 3.89 g (22 mmol) of 2-methylbenzoxazole-5-boronic acid, 4.25 g (22 mmol) of 2-methylbenzothiazole-6-boronic acid was used. Except that, according to the procedure described in Example 1, 3.2 g of the compound of the exemplified compound 112 was obtained as colorless crystals. Further, this compound was purified by sublimation at 340 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 401

Production of Exemplified Compound 136 In Example 3, instead of using 7.79 g (44 mmol) of 2-methylbenzoxazole-5-boronic acid, 8.49 g (44 mmol) of 2-methylbenzothiazole-5-boronic acid was used. Except that, in accordance with the operation described in Example 3, 3.6 g of the compound of Exemplary Compound 136 was obtained as pale yellow crystals. Further, this compound was purified by sublimation at 400 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 472

Production of Exemplified Compound 137 In Example 3, instead of using 7.79 g (44 mmol) of 2-methylbenzoxazole-5-boronic acid, 11.22 g (44 mmol) of 2-phenylbenzothiazole-5-boronic acid was used. Except that, in accordance with the operation described in Example 3, 4.2 g of the compound of Exemplified Compound 137 was obtained as pale yellow crystals. Further, this compound was purified by sublimation at 430 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 596

Preparation of Exemplified Compound 138 In Example 3, instead of using 7.79 g (44 mmol) of 2-methylbenzoxazole-5-boronic acid, 8.49 g (44 mmol) of 2-methylbenzothiazole-6-boronic acid was used. 3.8 g of the compound of Exemplified Compound 138 was obtained as pale yellow crystals according to the procedure described in Example 3. Further, this compound was purified by sublimation at 400 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 472

Preparation of Exemplary Compound 152 In Example 1, instead of using 3.89 g (22 mmol) of 2-methylbenzoxazole-5-boronic acid, 4.18 g of 1,2-dimethyl-1H-benzimidazole-5-boronic acid 3.7 g of the compound of exemplary compound 152 was obtained as colorless crystals according to the procedure described in Example 1 except that (22 mmol) was used. Further, this compound was purified by sublimation at 340 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 398

Preparation of Exemplified Compound 187 In Example 3, instead of using 7.79 g (44 mmol) of 2-methylbenzoxazole-5-boronic acid, 8.36 g of 1,2-dimethyl-1H-benzimidazole-5-boronic acid Except that (44 mmol) was used, 3.6 g of the compound of Exemplified Compound 187 was obtained as pale yellow crystals according to the procedure described in Example 3. Further, this compound was purified by sublimation at 410 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 466

Preparation of Exemplified Compound 189 In Example 3, instead of using 7.79 g (44 mmol) of 2-methylbenzoxazole-5-boronic acid, 1-methyl-2-trifluoromethylbenzimidazole-5-boronic acid 10. Except that 12 g (44 mmol) was used, 3.9 g of the compound of Exemplified Compound 189 was obtained as pale yellow crystals according to the procedure described in Example 3. Further, this compound was purified by sublimation at 430 ° C. and 2 × 10 ⁻⁴ Pa.
FD-MS m / z = 574

Production of Organic Electroluminescent Device A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was subjected to ultrasonic cleaning using a neutral detergent, Semico Clean (manufactured by Furuuchi Chemical), ultrapure water, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (1-naphthyl) amino] biphenyl was deposited on the ITO transparent electrode to a thickness of 75 nm at a deposition rate of 0.2 nm / sec, and hole injection transport was performed. A layer was formed. Next, as a light emitting layer on the hole injecting and transporting layer, the compound of Exemplified Compound 7 and 4,4′-bis [2- (4-N, N-diphenylaminophenyl) vinyl] biphenyl are each deposited at a deposition rate of 2. A light emitting layer was formed by vapor deposition at a thickness of 40 nm at 0 nm / sec and 0.02 to 0.1 nm / sec. Further, tris (8-quinolinolato) aluminum was deposited on the light emitting layer at a deposition rate of 0.2 nm / sec to a thickness of 15 nm 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 at room temperature. Initially, the voltage value was 5.6 V, and blue light emission with a luminance of 920 cd / m ² was confirmed. The half life of luminance was 2000 hours.

In Example 15, when the light emitting layer was formed, an organic electroluminescent device was prepared according to the procedure described in Example 15 except that the compound of Exemplary Compound 10 was used instead of the compound of Exemplary Compound 7. Further, in the same manner as in Example 15, a DC voltage was applied to the device, and the characteristics of the device were measured. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

In Example 15, when the light emitting layer was formed, an organic electroluminescent device was prepared according to the procedure described in Example 15 except that the compound of Exemplified Compound 57 was used instead of the compound of Illustrated Compound 7. Further, in the same manner as in Example 15, a DC voltage was applied to the device, and the characteristics of the device were measured. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

In Example 15, when the light emitting layer was formed, an organic electroluminescent device was prepared according to the procedure described in Example 15 except that the compound of Exemplified Compound 58 was used instead of the compound of Illustrated Compound 7. Further, in the same manner as in Example 15, a DC voltage was applied to the device, and the characteristics of the device were measured. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

In Example 15, when the light emitting layer was formed, an organic electroluminescent device was prepared according to the procedure described in Example 15 except that the compound of Exemplified Compound 87 was used instead of the compound of Illustrated Compound 7. Further, in the same manner as in Example 15, a DC voltage was applied to the device, and the characteristics of the device were measured. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

In Example 15, when the light emitting layer was formed, an organic electroluminescent device was prepared according to the procedure described in Example 15 except that the compound of Exemplary Compound 91 was used instead of the compound of Exemplary Compound 7. Further, in the same manner as in Example 15, a DC voltage was applied to the device, and the characteristics of the device were measured. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

In Example 15, when the light emitting layer was formed, an organic electroluminescent device was produced according to the procedure described in Example 15 except that the compound of Exemplified Compound 136 was used instead of the compound of Illustrated Compound 7. Further, in the same manner as in Example 15, a DC voltage was applied to the device, and the characteristics of the device were measured. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

In Example 15, an organic electroluminescent device was prepared according to the procedure described in Example 15 except that the compound of Exemplified Compound 137 was used instead of the compound of Illustrated Compound 7 in forming the light emitting layer. Further, in the same manner as in Example 15, a DC voltage was applied to the device, and the characteristics of the device were measured. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

In Example 15, when the light emitting layer was formed, an organic electroluminescent device was prepared according to the procedure described in Example 15 except that the compound of exemplary compound 152 was used instead of using the compound of exemplary compound 7. Further, in the same manner as in Example 15, a DC voltage was applied to the device, and the characteristics of the device were measured. Blue light emission was confirmed from the device. The results are shown in Table 1 (Table 1).

Comparative Example 1:
In Example 15, Example 4 was used except that 4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl was used instead of the compound of Exemplary Compound 7 in forming the light emitting layer. According to the operation described in 15, an organic electroluminescent element was produced. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

Comparative Example 2:
In Example 15, when the light emitting layer was formed, an organic electroluminescent device was produced according to the procedure described in Example 15 except that 9,10-diphenylanthracene was used instead of using the compound of Exemplary Compound 7. Blue light emission was confirmed from the device. Further, the characteristics were examined, and the results are shown in Table 1 (Table 1).

Comparative Example 3:
In Example 15, the procedure described in Example 15 was followed except that 9,10-bis (3,5-diphenylphenyl) anthracene was used instead of the compound of Exemplary Compound 7 in forming the light emitting layer. An organic electroluminescent element was prepared. Blue-green light emission was confirmed from the device. Further, the characteristics were examined, and 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 washed with UV / ozone, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr.
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, and the second hole An injection transport layer was formed. Next, 4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl and the compound of Exemplified Compound 112 are deposited on the hole injecting and transporting layer at a deposition rate of 0.2 nm / sec. 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, green light emission of 5.7 V and luminance of 960 cd / m ² was confirmed. The half life of luminance was 2500 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 washed with UV / ozone, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. 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 to a thickness of 50 nm. Vapor deposition was performed to form a first hole injection transport layer, and then 4,4′-bis [N-phenyl-N- (1-naphthyl) amino] -1,1′-biphenyl was deposited at a deposition rate of 0.2 nm / The second hole injecting and transporting layer was formed by vapor deposition at a thickness of 20 nm in sec. Further, a compound represented by the exemplified compound 189 was vapor deposited at a thickness of 40 nm at 0.1 nm / sec to emit light. Next, tris (8-quinolinolato) aluminum was vapor-deposited to a thickness of 50 nm at a vapor deposition rate of 0.2 nm / sec to form an electron injecting and transporting layer. Steamed magnesium and silver An organic electroluminescent device was produced by co-evaporation (weight ratio 10: 1) to a thickness of 200 nm at a rate of 0.2 nm / sec to form a cathode, and a DC voltage was applied to the produced organic electroluminescent device, and the resultant was dried in a dry atmosphere. It was continuously driven at a constant current density of 10 mA / cm ^{2. In} the initial stage, blue light emission of 5.6 V and luminance of 760 cd / m ² was confirmed, and the luminance half-life was 1900 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 washed with UV / ozone, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. 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. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was again decompressed to 3 × 10 ⁻⁶ Torr. Next, the compound of Exemplified Compound 138 and rubrene were co-deposited from different vapor deposition sources to a thickness of 55 nm at a vapor deposition rate of 0.2 nm / sec (weight ratio 10: 1), and the second hole injection transport layer was also provided. A light emitting layer was formed. 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 5.4 V and luminance of 980 cd / m ² was confirmed. The half life of luminance was 2500 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 washed with UV / ozone, fixed to the substrate holder of the vapor deposition apparatus, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, Exemplified Compound 187 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. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was again decompressed to 3 × 10 ⁻⁶ Torr. Next, the compound of Exemplified Compound 136 and rubrene were co-deposited from different vapor deposition sources to a thickness of 55 nm at a vapor deposition rate of 0.2 nm / sec (weight ratio 10: 1), and the second hole injection transport layer was also provided. A light emitting layer was formed. 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 5.5 V and luminance of 950 cd / m ² was confirmed. The half life of luminance was 2600 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, a 40 nm hole is formed on the ITO transparent electrode by spin coating using a 3 wt% dichloroethane solution containing a compound of polycarbonate (weight average molecular weight 39000) and exemplary compound 91 in a weight ratio of 100: 50. An injection transport 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 Torr. 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 electroluminescent element in a dry atmosphere, a current of 87 mA / cm ² flowed. Green light emission with a luminance of 820 cd / m ² was confirmed. The luminance half-life was 500 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), the compound of exemplary compound 66, and tris (8-quinolinolato) aluminum are contained in a weight ratio of 100: 50: 0.5, respectively. A light emitting layer having a thickness of 100 nm was formed by spin coating using a weight% 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 Torr. 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 direct current voltage of 15 V was applied to the produced organic electroluminescent element in a dry atmosphere, a current of 82 mA / cm ² flowed. Green light emission with a luminance of 860 cd / m ² was confirmed. The half life of luminance was 450 hours.

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

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

Explanation of symbols

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

Claims (9)

An anthracene compound represented by the formula (1).

[In the formula (1), Y _{1 to} Y ₁₀ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an ester group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, or an aralkyloxy group. A group, an aryl group or an aryloxy group, and the adjacent groups of Y _{1 to} Y ₁₀ may form a ring together with the adjacent groups, and at least one of Y _{1 to} Y ₁₀ is represented by the formula (2 Is a group represented by

[In the formula (2), X represents an oxygen atom, a sulfur atom or —N (R) —, and R ₁ , R ₂ and R each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, It represents an ester group, an alkylcarbonyl group, an alkyl group, an alkoxy group, an aralkyl group, an aralkyloxy group, an aryl group or an aryloxy group. ] The anthracene compound according to claim 1, wherein in formula (1), at least one of Y ₉ and Y ₁₀ is a group represented by formula (2). The anthracene compound of Claim 1 represented by following formula (3).

In [Equation _(3), Y 1 to Y ₉ is the same atom or group as in formula _(1), adjacent groups of Y 1 to Y ₉ are also form a ring with each adjacent group Good. X, R ₁ and R ₂ represent the same atom or group as in formula (2). ] The anthracene compound of Claim 1 represented by following formula (4).

In [Equation _(4), Y 1 to Y ₈ are the same atom or group as in formula _(1), adjacent groups of Y 1 to Y ₈ are also form a ring with each adjacent group Good. X, R ₁ and R ₂ represent the same atom or group as in formula (2). ] An organic electroluminescence device comprising at least one layer containing at least one anthracene compound represented by the formula (1) between a pair of electrodes. The organic electroluminescent element according to claim 5, wherein the layer containing the anthracene compound represented by the formula (1) is a light emitting layer. The organic electroluminescent device according to claim 5, wherein the layer containing the anthracene compound represented by the formula (1) is a hole injection transport layer. The organic electroluminescent element according to any one of claims 5 to 7, further comprising a hole injecting and transporting layer between the pair of electrodes. The organic electroluminescent element according to claim 5, further comprising an electron injecting and transporting layer between the pair of electrodes.

Images