JP2000327640A - Amine compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new amine compound improved in stability and durability, and useful e.g. for hole implantation and transportation materials in organic electroluminescence elements. SOLUTION: This new compound is expressed by formula I, wherein Ar1 to Ar6 are each an aryl; Z1 and Z2 are each H, a halogen or the like and; X1 and X2 are each an arylene and is e.g. a compound of formula II. The new compound is obtained e.g. by the reaction (Ullmann reaction) of a compound of formula III wherein Y1 and Y2 are each a halogen, preferably Cl produced from 2,7-dihalogenofluorene derivative and a compound of the formula HN-(Ar1)(Ar2) with a compound of the formula IV and a compound of formula V in the presence of a copper compound. The new compound is also obtained e.g. by the reaction (Ullmann reaction) of a compound of formula III and a compound of the formula VI in the presence of a copper compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a novel amine compound.

[0002]

2. Description of the Related Art Conventionally, amine compounds have been used as intermediates for producing various dyes or as various functional materials. As a functional material, for example, it has been used as a charge transport material for an electrophotographic photosensitive member. Furthermore, recently, it has been proposed to be useful as a hole injection / transport material for an organic electroluminescence device (organic electroluminescence device: organic EL device) using an organic material as a light emitting material [for example, App.
l. Phys. Lett., 51 , 913 (1987)]. It has been proposed to use 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl as a hole injection / transport material for organic electroluminescent devices [Jpn. J. Appl. Ph
ys., 27 , L269 (1988)]. Further, as a hole injection / transport material for an organic electroluminescent device, for example, a 9,9-dialkyl-2,7-bis (N, N-diphenylamino) fluorene derivative [eg, 9,9-dimethyl-2,7- It has been proposed to use bis (N, N-diphenylamino) fluorene] (JP-A-5-25473).
However, organic electroluminescent devices using these amine compounds as hole injecting and transporting materials have disadvantages such as poor stability and durability. At present, a novel amine compound is desired to obtain a more improved organic electroluminescent device.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a novel amine compound. More specifically, it is an object of the present invention to provide a novel amine compound suitable for a hole injection / transport material of an organic electroluminescent device.

[0004]

Means for Solving the Problems The present inventors have made intensive studies on various amine compounds, and as a result, completed the present invention. That is, the present invention provides an amine compound represented by the general formula (1):

Embedded image(Wherein, Ar₁~ Ar₆Is a substituted or unsubstituted aryl
A group represented by Ar ₁And Ar_Two, Ar_ThreeAnd Ar_FourYou
And Ar_FiveAnd Ar₆Is nitrogen containing together with the attached nitrogen atom
R may represent a heterocyclic ring;₁And R_Two
Represents a hydrogen atom, a linear, branched or cyclic alkyl group,
Or unsubstituted aryl group, or substituted or unsubstituted
Represents an aralkyl group of₁And Z_TwoIs a hydrogen atom,
A logen atom, a linear, branched or cyclic alkyl group,
Chain, branched or cyclic alkoxy groups, or substituted or
Represents an unsubstituted aryl group;₁And X_TwoIs replaced
Or an unsubstituted arylene group. In the compound represented by the general formula (1), X₁and
X_TwoWherein the amine is a group represented by the general formula (2)
Compounds. -(A₁-X₁₁)_m-A_Two-(2) (where A₁And A_TwoIs substituted or unsubstituted phenyle
Group, substituted or unsubstituted naphthylene group, or substituted
Or an unsubstituted fluorene-diyl group; ₁₁Is simply
Represents a bond, an oxygen atom or a sulfur atom, and m is 0 or 1
Represents )

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The present invention relates to an amine compound represented by the general formula (1).

Embedded image(Wherein, Ar₁~ Ar₆Is a substituted or unsubstituted aryl
A group represented by Ar ₁And Ar_Two, Ar_ThreeAnd Ar_FourYou
And Ar_FiveAnd Ar₆Is nitrogen containing together with the attached nitrogen atom
R may represent a heterocyclic ring;₁And R_Two
Represents a hydrogen atom, a linear, branched or cyclic alkyl group,
Or unsubstituted aryl group, or substituted or unsubstituted
Represents an aralkyl group of₁And Z_TwoIs a hydrogen atom,
A logen atom, a linear, branched or cyclic alkyl group,
Chain, branched or cyclic alkoxy groups, or substituted or
Represents an unsubstituted aryl group;₁And X_TwoIs replaced
Or an unsubstituted arylene group. )

In the general formula (1), Ar _{1 to} Ar ₆ represent a substituted or unsubstituted aryl group. Note that the aryl group represents a carbocyclic aromatic group such as a phenyl group, a naphthyl group, and an anthryl group, and a heterocyclic aromatic group such as a furyl group, a thienyl group, and a pyridyl group.

Ar _{1 to} Ar ₆ are preferably unsubstituted,
Alternatively, as the substituent, for example, a carbocyclic aromatic group having a total of 6 to 20 carbon atoms, which may be mono- or polysubstituted by a halogen atom, an alkyl group, an alkoxy group, or an aryl group, or a total of 3 to 3 20 heterocyclic aromatic groups, more preferably an unsubstituted or halogen atom, an alkyl group having 1 to 14 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, or an aryl group having 6 to 10 carbon atoms A total of 6 to 20 carbon atoms which may be mono- or polysubstituted
And more preferably an unsubstituted or halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or 6 to 6 carbon atoms.
It is a carbocyclic aromatic group having 6 to 16 carbon atoms, which may be mono- or polysubstituted with 10 aryl groups.

Specific examples of Ar _{1 to} Ar ₆ include, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group,
-Anthryl group, 9-anthryl group, 2-fluorenyl group, 4-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 3-furyl group, 2-furyl group, 3
-Thienyl group, 2-thienyl group, 2-oxazolyl group,
2-thiazolyl group, 2-benzooxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethyl Phenyl 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, 2-neopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl Group, 4-
(2′-ethylbutyl) phenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4- (2 ′
-Ethylhexyl) phenyl group, 4-tert-octylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-n-tetradecylphenyl group, 4-
Cyclopentylphenyl group, 4-cyclohexylphenyl group, 4- (4'-methylcyclohexyl) phenyl group, 4- (4'-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4- Ethyl-1-naphthyl group, 6-n
-Butyl-2-naphthyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2, 4-diethylphenyl group, 2,
3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group,
2,6-diethylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4
-Di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 4,6-di-tert-butyl-2-methylphenyl group, 5-tert-butyl-2-methylphenyl group, 4 A tert-butyl-2,6-dimethylphenyl group,
9-methyl-2-fluorenyl group, 9-ethyl-2-fluorenyl group, 9-n-hexyl-2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-
Diethyl-2-fluorenyl group, 9,9-di-n-propyl-2-fluorenyl group,

4-methoxyphenyl, 3-methoxyphenyl, 2-methoxyphenyl, 4-ethoxyphenyl, 3-ethoxyphenyl, 2-ethoxyphenyl, 4-n-propoxyphenyl, 3-n -Propoxyphenyl group, 4-isopropoxyphenyl group, 2-
Isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-
Isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 4-neopentyloxyphenyl group, 2
-Neopentyloxyphenyl group, 4-n-hexyloxyphenyl group, 2- (2'-ethylbutyl) oxyphenyl group, 4-n-octyloxyphenyl group, 4-n
-Decyloxyphenyl group, 4-n-dodecyloxyphenyl group, 4-n-tetradecyloxyphenyl group, 4
-Cyclohexyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-methoxy-1-naphthyl group,
4-methoxy-1-naphthyl group, 4-n-butoxy-1
-Naphthyl group, 5-ethoxy-1-naphthyl group, 6-methoxy-2-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butoxy-2-naphthyl group, 6-n-hexyloxy-2 -Naphthyl group, 7-methoxy-2-naphthyl group, 7-n-butoxy-2-naphthyl group, 2-methyl-4-methoxyphenyl group, 2-methyl-5-methoxyphenyl group, 3-methyl-5 Methoxyphenyl group,
3-ethyl-5-methoxyphenyl group, 2-methoxy-
4-methylphenyl group, 3-methoxy-4-methylphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group,
3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5-diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-ethoxyphenyl group, 2-methoxy -6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4'-methylphenyl) phenyl group, 4- (3′-methylphenyl) phenyl group, 4-
(4′-methoxyphenyl) phenyl group, 4- (4′-
n-butoxyphenyl) phenyl group, 2- (2′-methoxyphenyl) phenyl group, 4- (4′-chlorophenyl) phenyl group, 3-methyl-4-phenylphenyl group, 3-methoxy-4-phenylphenyl group A 9-phenyl-2-fluorenyl group,

4-fluorophenyl, 3-fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 2-chlorophenyl,
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, 3,4
-Dichlorophenyl group, 3,5-dichlorophenyl group,
2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2,4-dichloro-1-naphthyl group,
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, 2 -Methyl-4-fluorophenyl group, 2-methyl-5-fluorophenyl group, 3
-Methyl-4-fluorophenyl group, 2-chloro-4-
Methylphenyl group, 2-chloro-5-methylphenyl group, 2-chloro-6-methylphenyl group, 2-methyl-
3-chlorophenyl group, 2-methyl-4-chlorophenyl group, 3-methyl-4-chlorophenyl group, 2-chloro-4,6-dimethylphenyl group, 2-methoxy-4-fluorophenyl group, 2-fluoro-4 -Methoxyphenyl group, 2-fluoro-4-ethoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3-fluoro-4-
Examples thereof include an ethoxyphenyl group, a 3-chloro-4-methoxyphenyl group, a 2-methoxy-5-chlorophenyl group, a 3-methoxy-6-chlorophenyl group, and a 5-chloro-2,4-dimethoxyphenyl group. However, the present invention is not limited to these.

In the compound represented by the general formula (1),
Further, Ar ₁ and Ar ₂ , Ar ₃ and Ar ₄ and Ar ₅
And Ar ₆ may form a nitrogen-containing heterocyclic ring together with the nitrogen atom to which they are bonded, and is preferably —NAr ₁ Ar ₂ ,
-NAr ₃ Ar ₄ and -NAr ₅ Ar ₆ represents a substituted or unsubstituted -N- Karubazoriiru group, a substituted or unsubstituted -N- phenoxazinyl Niiru group or a substituted or unsubstituted -N- phenolate thia Gini yl group, Which is preferably unsubstituted or as a substituent, for example, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or 6 to 10 carbon atoms
May be mono- or polysubstituted with an aryl group of
An N-carbazolyyl group, a -N-phenoxazinyl group,
Or -N-phenothiadinyl group, more preferably unsubstituted or halogen atom, having 1 to 1 carbon atoms.
An -N-carbazolyyl group, -N-phenoxazinyl group, which may be mono- or polysubstituted with an alkyl group having 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms, or- It is an N-phenothiadinyl group, more preferably an unsubstituted -N-carbazolyyl group, an unsubstituted -N-phenoxazinyl group, or an unsubstituted -N-phenothiadinyl group.

[0012] _{-NAr 1 Ar 2, -NAr 3 Ar} 4 and -NAr ₅ Ar ₆ may form a nitrogen-containing heterocyclic ring, specific examples include, for example,-N-Karubazoriiru group, 2-methyl - N-carbazolyyl group, 3-methyl-
N-carbazolyyl group, 4-methyl-N-carbazolyyl group, 3-n-butyl-N-carbazolyyl group, 3-n
-Hexyl-N-carbazolyyl group, 3-n-octyl-N-carbazolyyl group, 3-n-decyl-N-carbazolyyl group, 3,6-dimethyl-N-carbazolyyl group, 2-methoxy-N-carbazolyyl group, 3-methoxy-N-carbazolyyl group, 3-ethoxy-N-carbazolyyl group, 3-isopropoxy-N-carbazolyyl group, 3-n-butoxy-N-carbazolyyl group, 3-n
-Octyloxy-N-carbazolyyl group, 3-n-decyloxy-N-carbazolyyl group, 3-phenyl-N
-Carbazolyyl group, 3- (4'-methylphenyl)-
N-carbazolyyl group, 3- (4'-tert-butylphenyl) -N-carbazolyyl group, 3-chloro-N-carbazolyyl group, -N-phenoxazinyl group, -N-phenothiazinyl group, 2- Methyl-N-phenothiadinyl group and the like can be mentioned.

In the compound represented by the general formula (1),
R ₁ and R ₂ represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, preferably a hydrogen atom, having 1 to 16 carbon atoms. A linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group having 4 to 16 carbon atoms, or a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms, more preferably a hydrogen atom, a carbon atom 1
-8 linear, branched or cyclic alkyl groups, 6-6 carbon atoms
A substituted or unsubstituted aryl group having 12 or a substituted or unsubstituted aralkyl group having 7 to 12 carbon atoms, and more preferably, R ₁ and R ₂ are linear, branched or cyclic having 1 to 8 carbon atoms. An alkyl group, a carbocyclic aromatic group having 6 to 10 carbon atoms, or a carbocyclic aralkyl group having 7 to 10 carbon atoms.

Specific examples of the substituted or unsubstituted aryl groups for R ₁ and R ₂ include, for example, Ar _{1 to} Ar ₆
The substituted or unsubstituted aryl group mentioned as a specific example can be exemplified. Specific examples of the linear, branched or cyclic alkyl group of R ₁ and R ₂ include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n
-Butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, cyclopentyl group, n-hexyl group, 2-ethylbutyl group, 3,3- Dimethylbutyl group, cyclohexyl group, n-heptyl group, cyclohexylmethyl group, n-octyl group, tert-octyl group, 2-
Ethylhexyl group, n-nonyl group, n-decyl group, n-
Examples include a dodecyl group, an n-tetradecyl group, an n-hexadecyl group, and the like, but are not limited thereto.

Specific examples of the substituted or unsubstituted aralkyl group of R ₁ and R ₂ include, for example, benzyl group, phenethyl group, α-methylbenzyl group, α, α-dimethylbenzyl group, 1-naphthylmethyl Group, 2-naphthylmethyl group, furfuryl group, 2-methylbenzyl group, 3
-Methylbenzyl group, 4-methylbenzyl group, 4-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert
-Butylbenzyl group, 4-n-hexylbenzyl group, 4
-Nonylbenzyl group, 3,4-dimethylbenzyl group, 3
-Methoxybenzyl group, 4-methoxybenzyl group, 4-
Ethoxybenzyl group, 4-n-butoxybenzyl group, 4
Aralkyl groups such as -n-hexyloxybenzyl group, 4-nonyloxybenzyl group, 4-fluorobenzyl group, 3-fluorobenzyl group, 2-chlorobenzyl group, and 4-chlorobenzyl group; It is not limited to these.

Z ₁ and Z ₂ represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group. Atom, halogen atom, C1-C16 linear, branched or cyclic alkyl group, C1-C16 linear, branched or cyclic alkoxy group, or C4-C20 substituted or unsubstituted aryl And more preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, or 6 carbon atoms. To 12 substituted or unsubstituted aryl groups, more preferably a hydrogen atom.

Specific examples of the linear, branched or cyclic alkyl groups of Z ₁ and Z ₂ include, for example, the linear, branched or cyclic alkyl groups mentioned as specific examples of R ₁ and R _2. can do. Z ₁ and Z ₂
As specific examples of the substituted or unsubstituted aryl group, there can be mentioned, for example, the substituted or unsubstituted aryl groups mentioned as specific examples of Ar _{1 to} Ar ₆ . Specific examples of the halogen atom of Z ₁ and Z ₂ , a linear, branched or cyclic alkoxy group include, for example, a halogen atom such as a fluorine atom, a chlorine atom and a bromine atom, for example, a methoxy group, an ethoxy group and an n-propoxy group. Group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, isopentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group, 2-ethylbutoxy group , 3,3-dimethylbutoxy, cyclohexyloxy, n-heptyloxy, cyclohexylmethyloxy, n-octyloxy, 2-ethylhexyloxy, n-nonyloxy, n-decyloxy, n-dodecyloxy Groups, n-tetradecyloxy group, n-hexadecyloxy group, etc. It can be mentioned carboxy group.

In the compound represented by the general formula (1),
X₁And X_TwoRepresents a substituted or unsubstituted arylene group
And preferably an arylene group represented by the general formula (2)
It is. -(A₁-X₁₁)_m-A_Two-(2) (where A₁And A_TwoIs substituted or unsubstituted phenyle
Group, substituted or unsubstituted naphthylene group, or substituted
Or an unsubstituted fluorene-diyl group; ₁₁Is simply
Represents a bond, an oxygen atom or a sulfur atom, and m is 0 or 1
Represents )

In the general formula (2), A ₁ and A ₂ represent a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorene-diyl group. Unsubstituted 1,3-phenylene group, substituted or unsubstituted 1,4-phenylene group, substituted or unsubstituted 1,4-naphthylene group, substituted or unsubstituted 1,5-naphthylene group, substituted or unsubstituted 2,6-naphthylene group, substituted or unsubstituted 2,7-naphthylene group, or substituted or unsubstituted fluorene-2,7-diyl group, more preferably substituted or unsubstituted 1,4- Phenylene group, substituted or unsubstituted 1,4-naphthylene group, substituted or unsubstituted 1,5-naphthylene group, substituted or unsubstituted 2,6-
It is a naphthylene group or a substituted or unsubstituted fluorene-2,7-diyl group. In the general formula (2), X
₁₁ represents a single bond, an oxygen atom or a sulfur atom. In the general formula (2), m represents 0 or 1. General formula (2)
In m, when m represents 1, more preferably A ₁ is a substituted or unsubstituted 1,4-phenylene group. In the compound represented by the general formula (1), X ₁ and X ₂ are more preferably represented by the general formulas (2-a) to (2)
An arylene group represented by -h).

[0020]

Embedded image (In the formula, Z ₁₁ and Z ₁₂ represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group.)

[0021]

Embedded image (In the formula, Z ₂₁ and Z ₂₂ represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group.)

[0022]

Embedded image (In the formula, Z ₃₁ and Z ₃₂ represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group.)

[0023]

Embedded image (In the formula, Z ₄₁ and Z ₄₂ represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group.)

[0024]

Embedded image (In the formula, Z ₅₁ and Z ₅₂ represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group.)

[0025]

Embedded image (Wherein, Z ₆₁ and Z ₆₂ is a hydrogen atom, a halogen atom, a straight-chain, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group or a substituted or unsubstituted aryl group,, R ₁₁ and R ₁₂ represents a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group.

[0026]

Embedded image (In the formula, Z ₇₁ and Z ₇₂ represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, or a substituted or unsubstituted aryl group.)

[0027]

Embedded image(Where Z₈₁And Z₈₂Is a hydrogen atom, a halogen atom,
Chain, branched or cyclic alkyl group, straight chain, branched or cyclic
Alkoxy group or substituted or unsubstituted aryl
Represents a hydroxyl group. In the general formulas (2-a) to (2-h), Z₁₁,
Z₁₂, Z_{twenty one}, Z_{twenty two}, Z ₃₁, Z₃₂, Z₄₁, Z₄₂, Z₅₁, Z
₅₂, Z₆₁, Z₆₂, Z₇₁, Z₇₂, Z₈₁And Z₈₂(Less than,
Z₁₁~ Z₈₂Abbreviated as) is a hydrogen atom, a halogen atom,
Chain, branched or cyclic alkyl group, straight chain, branched or cyclic
Alkoxy group or substituted or unsubstituted aryl
A hydrogen atom, a halogen atom,
A linear, branched or cyclic alkyl group having 1 to 16 primes,
A linear, branched or cyclic alkoxy group having a prime number of 1 to 16,
Alternatively, a substituted or unsubstituted aryl having 4 to 20 carbon atoms
Group, more preferably a hydrogen atom, a halogen atom,
A linear, branched or cyclic alkyl group having 1 to 8 carbon atoms,
A linear, branched or cyclic alkoxy group having a prime number of 1 to 8,
Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms
And more preferably a hydrogen atom.

Specific examples of the linear, branched or cyclic alkyl group of Z _{11 to} Z ₈₂ include, for example, the linear, branched or cyclic alkyl groups mentioned as specific examples of R ₁ and R _2. Can be. Specific examples of the substituted or unsubstituted aryl group of Z _{11 to} Z ₈₂ include, for example, Ar ₁
And substituted or unsubstituted aryl groups as specific examples of Ar ₆ to Ar ₆ .

Specific examples of the halogen atom, linear, branched or cyclic alkoxy group of Z _{11 to} Z ₈₂ include, for example, Z 11
_The halogen atom, linear, branched or cyclic alkoxy group mentioned as specific examples of ₁ and Z ₂ can be mentioned.

In the group represented by the general formula (2-f),
R ₁₁ and R ₁₂ represent a hydrogen atom, a linear, branched or cyclic alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group, preferably a hydrogen atom, a straight-chain having 1 to 16 carbon atoms. A chain, branched or cyclic alkyl group, a substituted or unsubstituted aryl group having 4 to 16 carbon atoms, or a substituted or unsubstituted aralkyl group having 5 to 16 carbon atoms, more preferably a hydrogen atom, 1 carbon atom;
-8 linear, branched or cyclic alkyl groups, 6-6 carbon atoms
A substituted or unsubstituted aryl group of 12 or a substituted or unsubstituted aralkyl group of 7 to 12 carbon atoms, and more preferably, R ₁₁ and R ₁₂ are linear, branched or cyclic of 1 to 8 carbon atoms. An alkyl group, a carbocyclic aromatic group having 6 to 10 carbon atoms, or a carbocyclic aralkyl group having 7 to 10 carbon atoms.

Specific examples of the substituted or unsubstituted aryl group of R ₁₁ and R ₁₂ include, for example, Ar _{1 to} Ar ₆
The substituted or unsubstituted aryl group mentioned as a specific example can be exemplified. Specific examples of the linear, branched or cyclic alkyl groups of R ₁₁ and R ₁₂ include, for example, the substituted or unsubstituted alkyl groups mentioned as specific examples of R ₁ and R ₂ . R ₁₁ and R ₁₂
Specific examples of the substituted or unsubstituted aralkyl group of
For example, substituted or unsubstituted aralkyl groups mentioned as specific examples of R ₁ and R ₂ can be exemplified.

Specific examples of the compound represented by the general formula (1) according to the present invention include, for example, the following compounds (Chem.
Chemical formula 58), but the present invention is not limited to these. In the formula, Ph represents a phenyl group, and Bz represents a benzyl group.

[0033]

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[0034]

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[0038]

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[0039]

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[0040]

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The compound represented by the general formula (1) according to the present invention can be produced by a method known per se.
That is, for example, a compound represented by the general formula (3) which can be produced from a 2,7-dihalogenofluorene derivative and HN-Ar ₁ Ar ₂ , a compound represented by the general formula (4), and It can be produced by reacting the compound represented by the general formula (5) in the presence of a copper compound (Ullman reaction). Further, it can also be produced by reacting a compound represented by the general formula (3) with a compound represented by the general formula (6) in the presence of a copper compound (Ullman reaction).

[0081]

Embedded image [Wherein Y ₁ and Y ₂ represent a halogen atom, and Ar ₁
To Ar ₆ , R ₁ , R ₂ , Z ₁ , Z ₂ , X ₁ and X ₂ have the same meaning as in formula (1). In the above formula, Y ₁ and Y ₂ represent a halogen atom, preferably a chlorine atom, a bromine atom or an iodine atom, more preferably a bromine atom or an iodine atom.

[0082]

The present invention will be described in more detail with reference to the following examples, which, of course, are not intended to limit the scope of the present invention. Example 1 Production of Compound of Exemplified Compound No. A-1 Under a nitrogen atmosphere, 2- [N, N-di (4′-methylphenyl) amino] -9,9-dimethyl-9H-7-iodofluorene 10.3 g, N, N-di [4- (N ', N'
10 g of [-diphenylamino) phenyl] amine, 10 g of metallic copper powder, and 20 g of anhydrous potassium carbonate were stirred in o-dichlorobenzene (100 g) at 190 ° C. for 8 hours. After the reaction mixture was cooled to 100 ° C. and filtered hot, methanol (200 g) was added to the filtrate, and the precipitated pale yellow solid was filtered and dried. The solid was treated by alumina column chromatography (eluent: toluene) and then recrystallized using a mixed solvent of toluene and n-hexane.
Thereafter, sublimation purification (350) under reduced pressure (10 ^-6 torr)
° C) to obtain 12 g of the compound of Exemplified Compound No. A-1 as pale yellow crystals. Glass transition temperature 117 ° C

Example 2 Preparation of Compound of Exemplified Compound No. A-2 Under a nitrogen atmosphere, 2- (N, N-diphenylamino)-
9,9-dimethyl-9H-7-iodofluorene 9.7
g, N, N-di [4- (N ', N'-di [4'-methylphenyl] amino) phenyl] amine, 11 g of metallic copper powder, and 20 g of anhydrous potassium carbonate in o-dichlorobenzene (100 g). The mixture was stirred at 190 ° C for 8 hours.
After the reaction mixture was cooled to 100 ° C. and filtered hot, methanol (200 g) was added to the filtrate, and the precipitated pale yellow solid was filtered and dried. The solid was treated by alumina column chromatography (eluent: toluene) and then recrystallized using a mixed solvent of toluene and n-hexane. Thereafter, sublimation purification (350 ° C.) under reduced pressure (10 ⁻⁶ torr)
Then, 12.5 g of the compound of Exemplified Compound No. A-2 was obtained as pale yellow crystals. Glass transition temperature 122 ° C

Example 3 Production of Compound of Exemplified Compound No. A-3 Under a nitrogen atmosphere, 2- [N- (3′-methylphenyl)
-N-phenylamino] -9,9-dimethyl-9H-7
-10.2 g of iodofluorene, N- [4- (N ',
N'-diphenylamino) phenyl] -N- [4-
10.6 g of (N ", N" -di [3'-methylphenyl] amino) phenyl] amine, 10 g of metallic copper powder, and 20 g of anhydrous potassium carbonate were added to o-dichlorobenzene (100 g).
In g), the mixture was stirred at 190 ° C. for 8 hours. Add 10 reaction mixtures
After cooling to 0 ° C and hot filtration, the filtrate was added with methanol (20%).
0 g) was added, and the precipitated pale yellow solid was filtered and dried. The solid was treated by alumina column chromatography (eluent: toluene) and then recrystallized using a mixed solvent of toluene and n-hexane. Then, under reduced pressure (1
Sublimation purification (350 ° C.) at 0 ⁻⁶ torr) afforded 12.3 g of Exemplified Compound No. A-3 as pale yellow crystals. Glass transition temperature 113 ° C

Example 4 Production of Compound of Exemplified Compound No. A-10 Under a nitrogen atmosphere, 2- [N- (1′-naphthyl) -N-
10.7 g of phenylamino] -9,9-dimethyl-9H-7-iodofluorene, N, N-di [4- (N ′-[
3′-Methylphenyl] -N′-phenylamino) phenyl] amine (10.6 g), metallic copper powder (10 g), and anhydrous potassium carbonate (20 g) were added to o-dichlorobenzene (100 g).
In g), the mixture was stirred at 190 ° C. for 8 hours. Add 10 reaction mixtures
After cooling to 0 ° C and hot filtration, the filtrate was added with methanol (20%).
0 g) was added, and the precipitated pale yellow solid was filtered and dried. The solid was treated by alumina column chromatography (eluent: toluene) and then recrystallized using a mixed solvent of toluene and n-hexane. Then, under reduced pressure (1
Sublimation purification (350 ° C.) at 0 ⁻⁶ torr), 11.8 g of the compound of Exemplified Compound No. A-10 as pale yellow crystals.
Obtained. Glass transition temperature 125 ° C

Example 5 Production of Compound of Exemplified Compound No. A-18 In Example 3, N- [4- (N ′, N′-diphenylamino) phenyl] -N- [4- (N ″, N "-di [
Instead of using 3'-methylphenyl] amino) phenyl] amine, N- [4- (N ', N'-diphenylamino) phenyl] -N- [4'-(N "-phenoxazinyl) phenyl A compound of Exemplified Compound No. A-18 was produced according to the method described in Example 3 except that an amine was used.

Example 6 Production of Compound of Exemplified Compound No. A-19 In Example 4, 2- [N- (1′-naphthyl) -N
-Phenylamino] -9,9-dimethyl-9H-7-iodofluorene, except that 2- (N-carbazolyyl) -9,9-dimethyl-9H-7-iodofluorene was used instead of using According to the method described in Example 4, compound of Exemplified Compound No. A-19 was produced. Glass transition temperature 122 ° C

Example 7 Preparation of Compound of Exemplified Compound No. B-4 In Example 1, instead of using N, N-di [4- (N ′, N′-diphenylamino) phenyl] amine, N- [4- (N ', N'-diphenylamino) -1
Example 1 except that -naphthyl] -N- [4 '-(N ", N" -diphenylamino) phenyl] amine was used.
The compound of Exemplified Compound No. B-4 was produced according to the method described in (1). Glass transition temperature 125 ° C

Example 8 Preparation of Compound of Exemplified Compound No. C-1 In Example 3, N- [4- (N ′, N′-diphenylamino) phenyl] -N- [4- (N ″, N "-di [
Instead of using 3'-methylphenyl] amino) phenyl] amine, N- [5- (N ', N'-diphenylamino) -1-naphthyl] -N- [4'-(N ", N"
-Diphenylamino) phenyl] amine, according to the method described in Example 3, except that Compound No. C-
One compound was prepared. Glass transition temperature 118 ° C

Example 9 Production of Compound of Exemplified Compound No. D-3 In Example 3, N- [4- (N ′, N′-diphenylamino) phenyl] -N- [4- (N ″, N "-di [
Instead of using 3'-methylphenyl] amino) phenyl] amine, N- [6- (N '-[3'-methylphenyl] -N'-phenylamino) -2-naphthyl]-
N- [4 "-(N"-[3 "'-methylphenyl]-
Exemplified compound No. D according to the method described in Example 3 except that N "-phenylamino) phenyl] amine was used.
The compound of No.-3 was prepared. Glass transition temperature 128 ° C

Example 10 Preparation of Compound of Exemplified Compound No. E-4 In Example 3, N- [4- (N ′, N′-diphenylamino) phenyl] -N- [4- (N ″, N "-di [
Instead of using 3'-methylphenyl] amino) phenyl] amine, N- [4- (N '-[3 "-methylphenyl] -N'-phenylamino) -4'-biphenyl] -N- [ The compound of Exemplified Compound No. E-4 was prepared according to the method described in Example 3 except that 4 "'-(N"-[3 ""-methylphenyl] -N "-phenyl) aminophenyl] amine was used. Manufactured. Glass transition temperature 135 ° C

Example 11 Exemplified Compound No. E-10
In Example 1, N- [4- (N '-[3 "-methyl) was used instead of using N, N-di [4- (N', N'-diphenylamino) phenyl] amine. Phenyl] −
N'-phenylamino) -4'-biphenyl] -N-
[4 "'-(N"-[3 ""-methylphenyl] -N "
-Phenyl) aminophenyl] amine, except that Exemplified Compound No. E-
Ten compounds were prepared. Glass transition temperature 133 ° C

Example 12 Exemplified Compound No. E-17
Preparation of a compound of the formula 2- [N, N-diphenylamino]-under a nitrogen atmosphere
9,9-diethyl-9H-7-iodofluorene10.
3 g, N- [4- (N ', N'-diphenylamino)-
11.5 g of 4'-biphenyl] -N- [4 "-(N" -carbazolyyl) phenyl] amine, 10 g of metallic copper powder,
And 20 g of anhydrous potassium carbonate was stirred in o-dichlorobenzene (100 g) at 190 ° C. for 8 hours. After the reaction mixture was cooled to 100 ° C. and filtered hot, methanol (200 g) was added to the filtrate, and the precipitated pale yellow solid was filtered.
Dried. This solid was subjected to alumina column chromatography (eluent: toluene), and then toluene and n-
Recrystallization was performed using a mixed solvent of hexane. Thereafter, it is purified by sublimation (350 ° C.) under reduced pressure (10 ⁻⁶ torr), and the compound of Exemplified Compound No. E-17 is obtained as pale yellow crystals.
g was obtained. Glass transition temperature 138 ° C

Example 13 Exemplified Compound No. E-25
In Example 2, N- [4- (N ′) was used instead of using N, N-di [4- (N ′, N′-di (4′-methylphenylamino) phenyl] amine). N'-diphenylamino) -4'-biphenyl] -N- [4 "-(N"-[
A compound of Exemplified Compound No. E-25 was produced according to the method described in Example 2 except that 4 "'-ethylphenyl] -N" -phenyl) -1-naphthyl] amine was used. Glass transition temperature 134 ° C

Example 14 Exemplified Compound No. E-28
In Example 2, N, N-di [4- (N ′, N′-di (4′-methylphenylamino) phenyl] amine was used in place of N, N-di [4- The compound of Exemplified Compound No. E-28 was produced according to the method described in Example 2 except that (N ′-[3 ″ -methylphenyl] -N′-phenylamino) -4′-biphenyl] amine was used. Glass transition temperature 145 ° C

Example 15 Exemplified Compound No. E-31
In Example 1, N, N-di [4- (N ′-[3] was used instead of using N, N-di [4- (N ′, N′-diphenylamino) phenyl] amine. Following the procedure described in Example 1 except that "-methylphenyl] -N'-phenylamino) -4'-biphenyl] amine was used.
The compound of Exemplified Compound No. E-31 was produced. Glass transition temperature 142 ° C

Example 16 Preparation of Compound of Exemplified Compound No. F-5 Under a nitrogen atmosphere, 2- (N, N-diphenylamino)-
9,9-dimethyl-9H-7-iodofluorene 9.7
g, 4- (N, N-diphenylamino) aniline 2.6
g, 10 g of metallic copper powder, and 20 g of anhydrous potassium carbonate were stirred in o-dichlorobenzene (100 g) at 190 ° C. for 8 hours. After the reaction mixture was cooled to 100 ° C. and filtered hot, methanol (200 g) was added to the filtrate, and the precipitated pale yellow solid was filtered and dried. The solid was treated by alumina column chromatography (eluent: toluene) and then recrystallized using a mixed solvent of toluene and n-hexane. Thereafter, the product was purified by sublimation (350 ° C.) under reduced pressure (10 ⁻⁶ torr) to obtain 7.5 g of the compound of Exemplified Compound No. F-5 as pale yellow crystals. Glass transition temperature 140 ° C

Example 17 Preparation of Compound of Exemplified Compound No. F-7 In Example 1, instead of using N, N-di [4- (N ′, N′-diphenylamino) phenyl] amine, N- [4- (N ', N'-diphenylamino) phenyl] -N- [2'-(N ", N" -diphenylamino) -9 ', 9'-dimethyl-9'H-7'- A compound of Exemplified Compound No. F-7 was produced according to the method described in Example 1 except that [fluorenyl] amine was used. Glass transition temperature 138 ° C

Example 18 Preparation of Compound of Exemplified Compound No. F-8 In Example 16, an alternative was to use 2- (N, N-diphenylamino) -9,9-dimethyl-9H-7-iodofluorene. Example compound number according to the method described in Example 16 except that 2- [N, N-di (4'-methylphenyl) amino] -9,9-dimethyl-9H-7-iodofluorene was used as the The compound of F-8 was prepared. Glass transition temperature 144 ° C

Example 19 Exemplified Compound No. F-13
In Example 16, instead of using 2- (N, N-diphenylamino) -9,9-dimethyl-9H-7-iodofluorene in Example 16, 2- [N- (3′-methoxyphenyl) -N-phenylamino] -9,9-dimethyl-9
Example 1 except that H-7-iodofluorene was used.
According to the method described in 6, the compound of Exemplified Compound No. F-13 was produced. Glass transition temperature 141 ° C

Example 20 Exemplified Compound No. F-14
In Example 16, instead of using 2- (N, N-diphenylamino) -9,9-dimethyl-9H-7-iodofluorene in Example 16, 2- [N- (1′-naphthyl)-
N-phenylamino] -9,9-dimethyl-9H-7-
A compound of Exemplified Compound No. F-14 was produced according to the method described in Example 16 except that iodofluorene was used. Glass transition temperature 148 ° C

Example 21 Exemplified Compound No. F-18
In Example 16, instead of using 2- (N, N-diphenylamino) -9,9-dimethyl-9H-7-iodofluorene in Example 16, 2- [N, N-di (4′- Compound of Exemplified Compound No. F-18 was produced according to the method described in Example 16 except that [ethylphenyl) amino] -9,9-diethyl-9H-7-iodofluorene was used. Glass transition temperature 150 ° C

Example 22 Exemplified Compound No. F-31
2- [N- (3′-methylphenyl) under a nitrogen atmosphere
-N-phenylamino] -9,9-dimethyl-9H-7
10 g of iodofluorene, 3.3 g of 4- (N, N-diphenylamino) -4′-biphenylamine, 10 g of metallic copper powder, and 20 g of anhydrous potassium carbonate in o-dichlorobenzene (100 g) at 190 ° C. for 8 hours Stirred.
After the reaction mixture was cooled to 100 ° C. and filtered hot, methanol (200 g) was added to the filtrate, and the precipitated pale yellow solid was filtered and dried. The solid was treated by alumina column chromatography (eluent: toluene) and then recrystallized using a mixed solvent of toluene and n-hexane. Then, sublimation purification (400 ° C) under reduced pressure (10 ^-6 torr)
Then, 7.2 g of the compound of Exemplified Compound No. F-31 was obtained as pale yellow crystals. Glass transition temperature 151 ° C

Example 23 Exemplified Compound No. F-33
In Example 2, N- [4- (N ′) was used instead of using N, N-di [4- (N ′, N′-di (4′-methylphenylamino) phenyl] amine). , N'-di [4 "-
Methylphenyl] amino) -4'-biphenyl] -N-
[2 "'-(N", N "-di [4""-methylphenyl] amino) -9"', 9 "'-dimethyl-9"' H-
Except that 7 "'-fluorenyl] amine was used, the compound of Exemplified Compound No. F-33 was produced according to the method described in Example 2. Glass transition temperature 156 ° C.

Example 24 Exemplified Compound No. F-37
In Example 22, instead of using 4- (N, N-diphenylamino) -4′-biphenylamine,
-[N, N-di (4'-methylphenyl) amino]-
A compound of Exemplified Compound No. F-37 was produced according to the method described in Example 22 except that 9,9-dimethyl-9H-7-aminofluorene was used. Glass transition temperature 160 ° C

Example 25 Exemplified Compound No. F-40
2- [N- (4'-methoxyphenyl) -N-phenylamino] -9,9-dimethyl-9H under a nitrogen atmosphere
10 g of -7-iodofluorene, 3.7 g of 2- (N, N-diphenylamino) -9,9-dimethyl-9H-7-aminofluorene, 10 g of metal copper powder, and 20 g of anhydrous potassium carbonate were added to o-dichlorobenzene ( 100g),
Stirred at 190 ° C. for 8 hours. After the reaction mixture was cooled to 100 ° C. and filtered hot, methanol (200 g) was added to the filtrate, and the precipitated pale yellow solid was filtered and dried. The solid was treated by alumina column chromatography (eluent: toluene) and then recrystallized using a mixed solvent of toluene and n-hexane. Then, under reduced pressure (10 ^-6 torr
) And sublimation purification (400 ° C), as pale yellow crystals,
6.9 g of compound of Exemplified Compound No. F-40 was obtained. Glass transition temperature 162 ° C

Example 26 Exemplified Compound No. F-42
In Example 25, 2- [N- (4'-methoxyphenyl) -N-phenylamino] -9,9-dimethyl-9
Instead of using H-7-iodofluorene,
[N- (1′-naphthyl) -N-phenylamino]-
A compound of Exemplified Compound No. F-42 was produced according to the method described in Example 25, except that 9,9-dimethyl-9H-7-iodofluorene was used. Glass transition temperature 165 ° C

Example 27 Preparation of Compound of Exemplified Compound No. G-8 In Example 22, 4- (N, N-diphenylamino) -4′-biphenylamine was used instead of 4- (N, N-diphenylamino) -4′-biphenylamine.
A compound of Exemplified Compound No. G-8 was produced according to the method described in Example 22 except that-[4 '-(N, N-diphenylamino) phenyloxy] aniline was used. Glass transition temperature 128 ° C

(Application Example 1) A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, and fixed to a substrate holder of a vapor deposition apparatus.
The pressure was reduced to × 10 ⁻⁶ Torr. First, on the ITO transparent electrode,
The compound of Exemplified Compound No. A-1 was deposited at a deposition rate of 0.2 nm.
/ Sec at a thickness of 75 nm to form a hole injection / transport layer. Then, on top of this, tris (8-quinolinolate)
Aluminum is deposited at 50 nm at a deposition rate of 0.2 nm / sec.
To form a light-emitting layer also serving as an electron injection / transport layer. Further, magnesium and silver were co-deposited thereon as a cathode at a deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio: 10: 1) to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. A DC voltage was applied to the produced organic electroluminescent device, and the device was continuously driven at 50 ° C. in a dry atmosphere at a constant current density of 10 mA / cm ² . Initially, 6.5 V, luminance 580
Green light emission of cd / m ² was confirmed. The half life of the luminance was 540 hours.

(Application Examples 2 to 7) In Application Example 1, instead of using the compound of Exemplified Compound No. A-1 in forming the hole injecting and transporting layer, the compound of Exemplified Compound No. A-10 (Applied Example 2) ), The compound of Exemplified Compound No. B-4 (Application Example 3), the compound of Exemplified Compound No. E-4 (Application Example 4), the compound of Exemplified Compound No. E-31 (Application Example 5),
An organic electroluminescent device was produced by the method described in Application Example 1 except that the compound of Exemplified Compound No. F-8 (Application Example 6) and the compound of Exemplified Compound No. F-31 (Application Example 7) were used. Green light emission was confirmed from each element. The characteristics were further examined, and the results are shown in Table 1.

(Comparative Examples 1 and 2) In Application Example 1, instead of using the compound of Exemplified Compound No. A-1 in forming the hole injecting and transporting layer, instead of using 4,4′-bis [N-phenyl-N -(3 "-methylphenyl) amino] biphenyl (Comparative Example 1), 9,9-dimethyl-2,7-bis (N,
An organic electroluminescent device was produced by the method described in Application Example 1 except that (N-diphenylamino) fluorene (Comparative Example 2) was used. Green light emission was confirmed from each element. The characteristics were further examined, and the results are shown in Table 1.

[0112]

[Table 1]

[0113]

According to the present invention, it has become possible to provide a novel amine compound. In particular, it has become possible to provide an amine compound having excellent characteristics as a hole injection / transport material for an organic electroluminescent device.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C07D 333/36 C07D 333/36 F term (Reference) 4C023 GA00 4C056 AA02 AB01 AC03 AD05 AE03 EA01 EB01 EC12 ED01 4C204 CB25 DB01 EB01 FB16 GB01 4H006 AA01 AB76 AB84 AB92 BJ50 BP30 BP60 BU48

Claims (2)

[Claims] 1. An amine compound represented by the general formula (1). Embedded image(Wherein, Ar₁~ Ar₆Is a substituted or unsubstituted aryl
A group represented by Ar ₁And Ar_Two, Ar_ThreeAnd Ar_FourYou
And Ar_FiveAnd Ar₆Is nitrogen containing together with the attached nitrogen atom
R may represent a heterocyclic ring;₁And R_Two
Represents a hydrogen atom, a linear, branched or cyclic alkyl group,
Or unsubstituted aryl group, or substituted or unsubstituted
Represents an aralkyl group of₁And Z_TwoIs a hydrogen atom,
A logen atom, a linear, branched or cyclic alkyl group,
Chain, branched or cyclic alkoxy groups, or substituted or
Represents an unsubstituted aryl group;₁And X_TwoIs replaced
Or an unsubstituted arylene group. ) 2. The compound represented by the general formula (1):
And X₁And X_TwoIs a group represented by the general formula (2)
The amine compound according to claim 1. -(A₁-X₁₁)_m-A_Two-(2) (where A₁And A_TwoIs substituted or unsubstituted phenyle
Group, substituted or unsubstituted naphthylene group, or substituted
Or an unsubstituted fluorene-diyl group; ₁₁Is simply
Represents a bond, an oxygen atom or a sulfur atom, and m is 0 or 1
Represents )