JP2003048868A - Amine, method of producing the same, and organic electroluminescent element including the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel amine that is suitable as a hole injection transport material for an organic electroluminescent element and the organic electroluminescent element having excellent stability and durability by using the amine. SOLUTION: The amine is represented by following general formula (1). The organic electroluminescent element comprises at least one layer that includes at least one of the amine represented by general formula (1) sandwiched between a couple of electrodes.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel amine compound and an organic electroluminescent device containing the amine compound.

[0002]

2. Description of the Related Art Conventionally, amine compounds have been used as intermediates for producing various dyes or various functional materials.
As a functional material, for example, a charge transport material for an electrophotographic photoreceptor has been used. Recently, it has been proposed that it is useful as a hole injecting and transporting material for an organic electroluminescence device (organic electroluminescence device: organic EL device) using an organic material as a light emitting material [eg, Appl.Phys.le.
tt., 51 , 913 (1987)].

An organic electroluminescence 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 to excite them by recombining. This element emits light by using the light emitted when an exciton is deactivated by generating a child (exington). The organic electroluminescence device can emit light at a low DC voltage of about several V to several tens of V. Further, by selecting the type of the fluorescent organic compound, various colors (for example, red, blue, green) can be obtained. ) Is possible. The organic electroluminescent device having such characteristics is expected to be applied to various light emitting devices, display devices and the like. However, in general,
Organic electroluminescent devices have drawbacks such as poor stability and durability. In order to efficiently inject and transport holes into a thin film containing a fluorescent organic compound of an organic electroluminescence device,
It has been proposed to use 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl as a hole injecting and transporting material [Jpn.J.Appl.Phys., 2
7 , L269 (1988)].

As the hole injecting and transporting material, for example,
It is also proposed to use 9,9-dialkyl-2,7-bis (N, N-diphenylamino) fluorene derivative [for example, 9,9-dimethyl-2,7-bis (N, N-diphenylamino) fluorene]. (Japanese Patent Laid-Open No. 5-25
473).

However, the organic electroluminescence device using these amine compounds as the hole injecting and transporting material also has drawbacks such as poor stability and durability.

At present, there is a demand for an organic electroluminescent device having excellent stability and durability, and therefore, a novel amine compound exhibiting excellent properties when used as an organic electroluminescent device is desired.

[0007]

SUMMARY OF THE INVENTION An object of the present invention is to provide a novel amine compound and an organic electroluminescence device containing the compound. More specifically, the present invention provides a novel amine compound suitable as a hole injecting / transporting material of an organic electroluminescent device, and an organic electroluminescent device using the amine compound, which is excellent in stability and durability.

[0008]

In order to solve the above problems, the inventors of the present invention have conducted extensive studies on various amine compounds and organic electroluminescent devices, and as a result, have completed the present invention. That is, the present invention provides 1) an amine compound represented by the general formula (1) (chemical formula 4),

[0009]

[Chemical 4]

[Wherein X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅
And A _{21 to} A ₂₅ are a hydrogen atom, a halogen atom, an optionally substituted linear, branched or cyclic alkyl group,
A straight chain optionally having a substituent, a branched or cyclic alkoxy group, a straight chain optionally having a substituent, a branched or cyclic alkylthio group, a straight chain optionally having a substituent, A branched or cyclic alkenyl group, a linear, branched or cyclic alkenyloxy group which may have a substituent,
Linear, branched or cyclic alkenylthio group which may have a substituent, linear chain which may have a substituent, branched or cyclic aralkyl group, which may have a substituent A branched or cyclic aralkylthio group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a cyano group, a hydroxyl group, a mercapto group, a -COOR ₁ group (in the group, R ₁ represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl A group, or a substituted or unsubstituted aryl group), a —COR ₂ group (in the group, R ₂ is a hydrogen atom, a linear or branched alkyl group which may have a substituent, or a substituent) Even if you have There represents a linear, branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or an amino group,), - O
COR ₃ group (wherein R ₃ is a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkenyl group which may have a substituent) ,
A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group), or a group represented by the formula (2)

[0011]

[Chemical 5]

(In the group, Y ₁ and Y _{2 each} have a hydrogen atom, a linear or branched alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituent. Represents an optionally substituted aryl group, Y ₁ and Y ₂
Represents a substituted or unsubstituted aromatic ring or aliphatic ring which may be bonded to each other together with a nitrogen atom), A
Adjacent groups of _{11 to} A ₁₅ and A _{21 to} A ₂₅ are bonded to each other to form a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted carbocyclic aliphatic group together with a substituted carbon atom. A ring, a substituted or heterocyclic aromatic ring, a substituted or unsubstituted heterocyclic aliphatic ring may be formed, and at least one of A _{11 to} A ₁₅ and at least one of A _{21 to} A ₂₅ are represented by the formula: (2)
Represents a group represented by

2) The amine compound represented by the formula (1), wherein at least one of X ₁ , X ₂ , X ₃ and X ₄ is a substituted or unsubstituted aryl group, 3) In the group represented by the formula (2), Y ₁ and Y ₂ may have a linear, branched or cyclic alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituted or The amine compound according to 1) or 2) which is an unsubstituted aryl group, 4) In the group represented by the formula (2), Y ₁ and Y ₂ are substituted or unsubstituted aryl groups 1), 2) or 3) The amine compound described in 5), 5) The general formula (1), which comprises reacting the compound represented by the general formula (3) (formula 6) with the compound represented by the general formula (4) A method for producing an amine compound represented by

[0014]

[Chemical 6]

6) An organic electroluminescent device comprising at least one layer containing at least one amine compound represented by the general formula (1) sandwiched between a pair of electrodes, and 7) represented by the general formula (1). 6) The organic electroluminescent device according to 6), wherein the layer containing an amine compound is a hole injecting and transporting layer, and 8) the layer containing an amine compound represented by the general formula (1) is a light emitting layer. ) Described organic electroluminescent device, 9) further having a light emitting layer between a pair of electrodes 6) or
The organic electroluminescent device according to 7), 10) further including an electron injecting and transporting layer between the pair of electrodes.
The organic electroluminescence device according to any one of 6) to 9).

[0016]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below. The amine compound of the present invention is a compound represented by the general formula (1) (formula 7).

[0017]

[Chemical 7]

[In the formula, X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅
And A _{21 to} A ₂₅ are a hydrogen atom, a halogen atom, an optionally substituted linear, branched or cyclic alkyl group,
A straight chain optionally having a substituent, a branched or cyclic alkoxy group, a straight chain optionally having a substituent, a branched or cyclic alkylthio group, a straight chain optionally having a substituent, A branched or cyclic alkenyl group, a linear, branched or cyclic alkenyloxy group which may have a substituent,
Linear, branched or cyclic alkenylthio group which may have a substituent, linear chain which may have a substituent, branched or cyclic aralkyl group, which may have a substituent A branched or cyclic aralkylthio group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a cyano group, a hydroxyl group, a mercapto group, a -COOR ₁ group (in the group, R ₁ represents a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl A group, or a substituted or unsubstituted aryl group), a —COR ₂ group (in the group, R ₂ is a hydrogen atom, a linear or branched alkyl group which may have a substituent, or a substituent) Even if you have There represents a linear, branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group or an amino group,), - O
COR ₃ group (wherein R ₃ is a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkenyl group which may have a substituent) ,
A substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group) or a group represented by the formula (2)

[0019]

[Chemical 8]

(In the group, Y ₁ and Y _{2 each} have a hydrogen atom, a linear or branched or cyclic alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituent. Represents an optionally substituted aryl group, Y ₁ and Y ₂
Represents a substituted or unsubstituted aromatic ring or aliphatic ring which may be bonded to each other together with a nitrogen atom), A
Adjacent groups of _{11 to} A ₁₅ and A _{21 to} A ₂₅ are bonded to each other to form a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted carbocyclic aliphatic group together with a substituted carbon atom. A ring, a substituted or heterocyclic aromatic ring, a substituted or unsubstituted heterocyclic aliphatic ring may be formed, and at least one of A _{11 to} A ₁₅ and at least one of A _{21 to} A ₂₅ are represented by the formula: (2)
Represents a group represented by

In the amine compound represented by the general formula (1), X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅ and A _{21 to} A are included.
₂₅ is preferably a hydrogen atom, a halogen atom, a linear or branched or cyclic alkyl group having 1 to 16 carbon atoms which may have a substituent, and a carbon number 1 which may have a substituent.
16 straight-chain, branched or cyclic alkoxy group, optionally substituted C 2-16 straight-chain, branched or cyclic alkenyl group, C 7-24 substituted or unsubstituted aralkyl A group, a cyano group, a group represented by the formula (2),
Alternatively, it represents a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, more preferably a hydrogen atom, a halogen atom, a straight chain having 1 to 12 carbon atoms which may have a substituent,
A branched or cyclic alkyl group, a straight chain having 1 to 12 carbon atoms which may have a substituent, a branched or cyclic alkoxy group, a straight chain having 2 to 12 carbon atoms which may have a substituent,
A branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, a cyano group, a group represented by the formula (2), or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, Represent

The aryl group represents a carbocyclic aromatic group such as a phenyl group and a naphthyl group, and a heterocyclic aromatic group such as a furyl group, a thienyl group and a pyridyl group.

In the amine compound represented by the general formula (1), X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅ and A
Linear ₂₁ to A _25, branched or cyclic alkyl group, straight chain,
A branched or cyclic alkoxy group, a linear, branched or cyclic alkylthio group, a linear, branched or cyclic alkenyl group, a linear, branched or cyclic alkenyloxy group, and a linear, branched or cyclic alkenylthio group, It may have a substituent, for example, a halogen atom, a carbon number of 4 to
20 aryl group, C1-C20 alkoxy group, C2-C20 alkoxyalkoxy group, C2-C2
0 alkenyloxy group, C4-20 aralkyloxy group, C5-20 aralkyloxyalkoxy group, C3-20 aryloxy group, C4-4
20 aryloxyalkoxy group, C5-20 arylalkenyl group, C6-20 aralkylalkenyl group, C1-20 alkylthio group, C2-20 alkoxyalkylthio group, C2 20
Alkylthioalkylthio group, alkenylthio group having 2 to 20 carbon atoms, aralkylthio group having 4 to 20 carbon atoms, aralkyloxyalkylthio group having 5 to 20 carbon atoms, aralkylthioalkylthio group having 5 to 20 carbon atoms, and 3 carbon atoms
To C20 arylthio group, C4 to C20 aryloxyalkylthio group, C4 to C20 arylthioalkylthio group, C4 to C20 heteroatom-containing cyclic alkyl group, or mono- or poly-substituted with a hydroxyl group or the like. It may be substituted.

Further, the aryl group contained in these substituents further includes a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkyl group having 3 to 10 carbon atoms.
And an aralkyl group having 4 to 10 carbon atoms, or the like.

In the amine compound represented by the general formula (1), X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅ and A _{21 to} A are used.
_{The 25} aralkyl group, aralkyloxy group, aralkylthio group, aryl group, aryloxy group, and aryl group in the arylthio group may have a substituent, for example, an alkyl group having 1 to 20 carbon atoms, a carbon atom An alkenyl group having 2 to 20 carbon atoms, an aralkyl group having 4 to 20 carbon atoms, an aryl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxyalkyl group having 2 to 20 carbon atoms, and 2 carbon atoms
To 20 alkoxyalkyloxy groups, 2 to 20 carbon atoms
Alkenyloxy group, C3-20 alkenyloxyalkyl group, C3-20 alkenyloxyalkyloxy group, C4-20 aralkyloxy group, C5-20 aralkyloxyalkyl group, carbon Aralkyloxyalkyloxy group having 5 to 20 carbon atoms, aryloxy group having 3 to 20 carbon atoms, aryloxyalkyl group having 4 to 20 carbon atoms, aryloxyalkyloxy group having 4 to 20 carbon atoms, and 2 to 20 carbon atoms An alkylcarbonyl group, an alkenylcarbonyl group having 3 to 20 carbon atoms,
Aralkylcarbonyl group having 5 to 20 carbon atoms, 4 to carbon atoms
20 arylcarbonyl group, C2-20 alkoxycarbonyl group, C3-20 alkenyloxycarbonyl group, C5-20 aralkyloxycarbonyl group, C4-20 aryloxycarbonyl group An alkylcarbonyloxy group having 2 to 20 carbon atoms, an alkenylcarbonyloxy group having 3 to 20 carbon atoms, an aralkylcarbonyloxy group having 5 to 20 carbon atoms, and 4 to 4 carbon atoms.
An arylcarbonyloxy group having 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an aralkylthio group having 4 to 20 carbon atoms,
Arylthio group having 3 to 20 carbon atoms, nitro group, cyano group, formyl group, halogen atom, halogenated alkyl group, hydroxyl group, amino group, N-monosubstituted amino group having 1 to 20 carbon atoms, and 2 to 40 carbon atoms It may be mono- or poly-substituted with a substituent such as an N, N-disubstituted amino group.

Further, the aryl group contained in these substituents further includes a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkyl group having 6 to 10 carbon atoms.
And an aralkyl group having 7 to 10 carbon atoms may be substituted.

In the general formula (1), the alkyl group, alkenyl group, aralkyl group and aryl group of R ₁ , R ₂ and R ₃ may have a substituent, for example,
It may be mono- or poly-substituted by the substituents described for X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅ and A _{21 to} A ₂₅ .

R ₁ is preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, and a total carbon which may have a substituent. A linear, branched or cyclic alkenyl group having a number of 2 to 24, an aralkyl group having a total carbon number of 7 to 24 which may have a substituent, or a total carbon number 6 to 2 which may have a substituent.
4 aryl groups, more preferably a hydrogen atom, a linear or branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, and a total which may have a substituent. It is an aralkyl group having 7 to 24 carbon atoms or an aryl group having 6 to 24 carbon atoms which may have a substituent.

R ₂ is preferably a hydrogen atom, a linear or branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, and a total carbon which may have a substituent. A linear, branched or cyclic alkenyl group having 2 to 24 carbon atoms, an aralkyl group having 7 to 24 carbon atoms which may have a substituent, and a total alkenyl group having 6 to 24 carbon atoms which may have a substituent. An aryl group or an amino group, more preferably a hydrogen atom, a linear, branched or cyclic alkyl group having a total carbon number of 1 to 24, which may have a substituent, or a substituent. A good aralkyl group having 7 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms which may have a substituent, or an amino group.

R ₃ is preferably a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, and 2 to 2 carbon atoms which may have a substituent. 24 linear, branched or cyclic alkenyl groups, aralkyl groups having 7 to 24 carbon atoms which may have a substituent, or aryl groups having 6 to 24 carbon atoms which may have a substituent. And, more preferably, a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, and an aralkyl having 7 to 24 carbon atoms which may have a substituent. A group or an aryl group having 6 to 24 carbon atoms which may have a substituent.

Further, X ₁ , X ₂ , X ₃ and X ₄ are preferably at least one substituted or unsubstituted aryl group, more preferably X ₁ , X ₂ , X ₃ and X ₄ Of these, two or more are substituted or unsubstituted aryl groups,
More preferably, three or more of X ₁ , X ₂ , X ₃ and X ₄ are substituted or unsubstituted aryl groups.

X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅ and A
Specific examples of the group represented by _{21 to} A ₂₅ include, for example, a hydrogen atom, a halogen atom such as fluorine, chlorine, bromine and iodine,

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 , N-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group, n-heptyl group, 1-methylhexyl group, n-octyl group, 1-methylheptyl group,
2-ethylhexyl group, 2-propylpentyl group, n-
Nonyl group, 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, 1-ethyloctyl group, n-undecyl group, 1- Methyldecyl group, n-dodecyl group, n-
Tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group, 1-octylnonyl group, n-octadecyl group, 1-nonyldecyl group , 1-decylundecyl group, n-eicosyl group, n
-Docosyl group, n-tetracosyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, 2-cyclohexylethyl group, bornel group, isobornel group, 1-norbornyl group, 2-norbornanemethyl group, 1-bicyclo [2 2.2.2] Octyl group, 1-adamantyl group, 3-noradamantyl group, 1-adamantylmethyl group, cyclobutyl group, cyclopentyl group, 1
-Methylcyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 3-methylcyclohexyl group,
2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,
6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group,
2,4,6-trimethylcyclohexyl 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 Base,
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-propoxyethyl group, 2-isopropoxyethyl group , 2-n-butoxyethyl 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-methoxypropyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-n-propoxypropyl group, 3-isopropoxypropyl group, 3-
(N-butoxy) propyl group, 3- (n-pentyloxy) propyl group, 3- (n-hexyloxy) propyl group, 3- (2'-ethylbutoxy) 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-propoxybutyl group, 4-isopropoxybutyl group, 4-n-butoxybutyl group, 4-n-hexyloxybutyl group, 4 -N-octyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl group, 5-methoxypentyl group, 5-ethoxypentyl group, 5-n-propoxypentyl group, 6-ethoxyhexyl group Group, 6-isopropoxyhexyl group, 6-n-butoxyhexyl group, 6-
n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8-
Methoxyoctyl group, 10-methoxydecyl group, 10-
n-butoxydecyl group, 12-ethoxydodecyl group, 1
2-isopropoxide dodecyl group, tetrahydrofurfuryl group,

2- (2'-methoxyethoxy) ethyl group, 2- (2'-ethoxyethoxy) ethyl group, 2-
(2'-n-butoxyethoxy) ethyl group, 3- (2 '
-Ethoxyethoxy) propyl group, 2-allyloxyethyl group, 2- (4'-pentenyloxy) ethyl group, 3
-Allyloxypropyl group, 3- (2'-hexenyloxy) propyl group, 3- (2'-heptenyloxy) propyl group, 3- (1'-cyclohexenyloxy) propyl group, 4-allyloxybutyl group,

Benzyloxymethyl group, 2-benzyloxyethyl group, 2-phenethyloxyethyl group, 2-
(4'-methylbenzyloxy) ethyl group, 2- (2 '
-Methylbenzyloxy) ethyl group, 2- (4'-fluorobenzyloxy) ethyl group, 2- (4'-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4'-methoxybenzyloxy) ) Propyl group, 4-benzyloxybutyl group, 2- (benzyloxymethoxy) ethyl group, 2- (4'-methylbenzyloxymethoxy) ethyl group,

Phenyloxymethyl group, 4-methylphenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group, 4-methoxyphenyloxymethyl group, 4-fluorophenyloxymethyl group, 4- Chlorophenyloxymethyl 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-phenyloxypropyl group, 3- (2 '
-Naphthyloxy) propyl group, 4-phenyloxybutyl group, 4- (2'-ethylphenyloxy) butyl group, 5- (4'-tert-butylphenyloxy) pentyl group, 6- (2'-chlorophenyloxy) ) Hexyl group, 8-phenyloxyoctyl group, 10-phenyloxydecyl group, 10- (3'-chlorophenyloxy)
Decyl group, 2- (2'-phenyloxyethoxy) ethyl group, 3- (2'-phenyloxyethoxy) propyl group, 4- (2'-phenyloxyethoxy) butyl group,

N-butylthiomethyl group, n-hexylthiomethyl group, 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-butylthioethyl group, 2-n-hexylthioethyl group, 2- n-octylthioethyl 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-allylthio Ethyl group, 2-benzylthioethyl group, 3- (4'-methylbenzylthio) propyl group, 4-benzylthiobutyl group, 2- (2'-benzyloxyethylthio) ethyl group, 3- (3'- Benzylthiopropylthio) propyl group, 2-phenylthioethyl group, 2- (4'-methoxyphenylthio) ethyl group, 2
-(2'-phenyloxyethylthio) ethyl group, 3-
(2'-phenylthioethylthio) propyl group,

Fluoromethyl group, 3-fluoropropyl group, 6-fluorohexyl group, 8-fluorooctyl group, trifluoromethyl group, 1,1-dihydro-perfluoroethyl group, 1,1-dihydro-perfluoro- group. 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-dihydro-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-trichloroethyl group,

2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, 6-hydroxyhexyl group, 5-hydroxyheptyl group, 8-hydroxyoctyl group Linear, branched or cyclic alkyl groups such as 10-hydroxydecyl group, 12-hydroxydodecyl group and 2-hydroxycyclohexyl group,

For example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, cyclopentyl group. Oxy group, n-hexyloxy group, 2-ethylbutoxy group, 3,3-dimethylbutoxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-dodecyloxy group, n-tetradecyloxy group, n-hexadecyloxy group, n-octadecyloxy group, n-eicosyloxy group, n-docosyloxy group, n-tetracosyloxy group ,

Fluoromethoxy group, trifluoromethoxy group, 1,1-dihydroperfluoroethoxy group, perfluoroethoxy group, 1,1-dihydroperfluoro- group
n-propoxy group, 1,1,3-trihydroperfluoro-n-propoxy group, 1,1-dihydroperfluoro-n-butoxy group, 1,1-dihydroperfluoro-n
-Pentyloxy group, 1,1-dihydroperfluoro-
n-hexyloxy group, 4-chlorocyclohexyloxy group, 1,1-dihydroperfluoro-n-octyloxy group, 1,1-dihydroperfluoro-n-decyloxy group, 1,1-dihydroperfluoro-n- Dodecyloxy group, 1,1-dihydroperfluoro-n-hexadecyloxy group,

Ethoxymethoxy group, 1-methoxyethoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-n-propoxyethoxy group, 2-isopropoxyethoxy group, 2-n-butoxyethoxy group, 2- n-
Hexyloxyethoxy group, 2-n-octyloxyethoxy group, 2- (2'-ethylhexyloxy) ethoxy group, 2-n-decyloxyethoxy group, 2-methoxypropoxy group, 3-methoxypropoxy group, 3-ethoxy Propoxy group, 3-isopropoxypropoxy group, 3
-N-butoxypropoxy group, 3-n-hexyloxypropoxy group, 3-n-octyloxypropoxy group,
2-methoxybutoxy group, 3-methoxybutoxy group, 4
-Methoxybutoxy group, 4-ethoxybutoxy group, 4-
Isopropoxybutoxy group, 4-n-butoxybutoxy group, 4-n-hexyloxybutoxy group, 4-n-decyloxybutoxy group, 4-n-dodecyloxybutoxy group, 5-ethoxypentyloxy group, 6-methoxy Hexyloxy group, 6-ethoxyhexyloxy group, 6-isopropoxyhexyloxy group, 4-methoxycyclohexyloxy group, 7-methoxyheptyloxy group, 8-
Ethoxyoctyloxy group, 10-methoxydecyloxy group, 12-ethoxydodecyloxy group, 2- (2'-
Methoxyethyloxy) ethoxy group, 3- (2′-ethoxyethyloxy) propoxy group,

2-benzyloxyethoxy group, 2- (4
-Methylbenzyloxy) ethoxy group, 2- (4-methoxybenzyloxy) ethoxy group, 3- (4-ethylbenzyloxy) propoxy group, 4- (3-fluorobenzyloxy) butoxy group, 4- (4-chloro) Benzyloxy) butoxy group, 6- (3-methylbenzyloxy)
Hexyloxy group,

Phenyloxymethoxy group, 2-phenyloxyethoxy group, 2- (1'-naphthyloxy) ethoxy group, 2- (2'-naphthyloxy) ethoxy group, 2
-(4'-methylphenyloxy) ethoxy group, 2-
(4'-methoxyphenyloxy) ethoxy group, 2-
(3′-ethoxyphenyloxy) ethoxy group, 2-
(4'-chlorophenyloxy) ethoxy group, 3-phenyloxypropoxy group, 3- (4'-ethylphenyloxy) propoxy group, 3- (4'-chlorophenyloxy) propoxy group, 3- (2'-naphthyloxy) ) A linear, branched or cyclic alkoxy group such as a propoxy group, a 4-phenyloxybutoxy group, a 6-phenyloxyhexyloxy group, an 8-phenyloxyoctyloxy group and a 10-phenyloxydecyloxy group,

For example, methylthio group, ethylthio group, n
-Propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, n-pentylthio group, neopentylthio group, isopentylthio group, cyclopentylthio group, n-hexylthio group, 2-
Ethylbutylthio group, 3,3-dimethylbutylthio group,
Cyclohexylthio group, n-heptylthio group, n-octylthio group, 2-ethylhexylthio group, n-nonylthio group, n-decylthio group, n-dodecylthio group, n-tetradecylthio group, n-hexadecylthio group, n-octadecyl group Thio group, n-eicosylthio group, n-docosylthio group, n-tetracosylthio group,

Fluoromethylthio group, trifluoromethylthio group, 1,1-dihydroperfluoroethylthio group, perfluoroethylthio group, 1,1-dihydroperfluoro-n-propylthio group, 1,1,3-trihydro Perfluoro-n-propylthio group, 1,1-dihydroperfluoro-n-butylthio group, 1,1-dihydroperfluoro-n-pentylthio group, 1,1-dihydroperfluoro-n-hexylthio group, 4-chloro Cyclohexylthio group, 1,1-dihydroperfluoro-n-
Octylthio group, 1,1-dihydroperfluoro-n-
Decylthio group, 1,1-dihydroperfluoro-n-dodecylthio group, 1,1-dihydroperfluoro-n-hexadecylthio group,

Ethoxymethylthio group, 1-methoxyethylthio group, 2-methoxyethylthio group, 2-ethoxyethylthio group, 2-n-propoxyethylthio group, 2-isopropoxyethylthio group, 2-n-butoxy group. Ethylthio group, 2-n-hexyloxyethylthio group, 2-n-
Octyloxyethylthio group, 2- (2'-ethylhexyloxy) ethylthio group, 2-n-decyloxyethylthio group, 2-methoxypropylthio group, 3-methoxypropylthio group, 3-ethoxypropylthio group, 3 -Isopropoxypropylthio group, 3-n-butoxypropylthio group, 3-n-hexyloxypropylthio group, 3
-N-octyloxypropylthio group, 2-methoxybutylthio group, 3-methoxybutylthio group, 4-methoxybutylthio group, 4-ethoxybutylthio group, 4-isopropoxybutylthio group, 4-n-butoxy group Butylthio group, 4-n-hexyloxybutylthio group, 4-n-decyloxybutylthio group, 4-n-dodecyloxybutylthio group, 5-ethoxypentylthio group, 6-methoxyhexylthio group, 6- Ethoxyhexylthio group, 6-isopropoxyhexylthio group, 4-methoxycyclohexylthio group, 7-methoxyheptylthio group, 8-ethoxyoctylthio group, 10-methoxydecylthio group, 12
-Ethoxydodecylthio group, 2-[(2'-methoxyethyl) oxy] ethylthio group, 3-[(2'-ethoxyethyl) oxy] propylthio group,

2-benzyloxyethylthio group, 2-
(4-methylbenzyloxy) ethylthio group, 2- (4
-Methoxybenzyloxy) ethylthio group, 3- (4-
Ethylbenzyloxy) propylthio group, 4- (3-fluorobenzyloxy) butylthio group, 4- (4-chlorobenzyloxy) butylthio group, 6- (3-methylbenzyloxy) hexylthio group,

Phenyloxymethylthio group, 2-phenyloxyethylthio group, 2- (1'-naphthyloxy)
Ethylthio group, 2- (2'-naphthyloxy) ethylthio group, 2- (4'-methylphenyloxy) ethylthio group, 2- (4'-methoxyphenyloxy) ethylthio group, 2- (3'-ethoxyphenyloxy) ) Ethylthio group, 2- (4'-chlorophenyloxy) ethylthio group, 3-phenyloxypropylthio group, 3- (4'-
Ethylphenyloxy) propylthio group, 3- (4'-
Chlorophenyloxy) propylthio group, 3- (2'-
Naphthyloxy) propylthio group, 4-phenyloxybutylthio group, 6-phenyloxyhexylthio group, 8
-A linear, branched or cyclic alkylthio group such as a phenyloxyoctylthio group or a 10-phenyloxydecylthio group,

For example, vinyl group, allyl group, 2-butenyl group, 3-butenyl group, 1-methyl-4-pentenyl group, 2-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2 -Hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 2-heptenyl group, 1-vinylhexyl group, 3-nonenyl group, 6-
Nonenyl group, 9-decenyl group, 10-undecenyl group,
13-tetradecenyl group, 15-hexadecenyl group, 1
7-octadecenyl group, 23-n-tetracosenyl group,
1-cyclopentenyl group, 1-cyclohexenyl group, ethoxyvinyl group, n-butoxyvinyl group, benzylvinyl group, styryl group, styrylmethyl group, 2-styrylethyl group, 2,2-diphenylvinyl group, 2- ( 4′-methylphenyl) vinyl group, 2- (3′-methylphenyl) vinyl group, 2- (4′-methoxyphenyl) vinyl group, 2- (4′-chlorophenyl) vinyl group, phenyloxyvinyl group, etc. Linear, branched or cyclic alkenyl group,

For example, vinyloxy group, allyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1
-Methyl-4-pentenyloxy group, 2-pentenyloxy group, 4-pentenyloxy group, 1-methyl-2-butenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5- Hexenyloxy group, 2-heptenyloxy group, 1-vinylhexyloxy group, 3-nonenyloxy group, 6-nonenyloxy group, 9-decenyloxy group, 10-undecenyloxy group, 13-tetradecenyloxy group, 15- Hexadecenyloxy group, 17-octadecenyloxy group, 2
3-tetracocenyloxy group, 1-cyclopentenyloxy group, 1-cyclohexenyloxy group, ethoxyvinyloxy group, n-butoxyvinyloxy group, benzylvinyloxy group, styryloxy group, phenyloxyvinyloxy group, etc. A linear, branched or cyclic alkenyloxy group,

For example, vinylthio group, allylthio group, 2
-Butenylthio group, 3-butenylthio group, 4-pentenylthio group, 5-hexenylthio group, 9-decenylthio group, 13-tetradecenylthio group, 15-hexadecenylthio group, 17-octadecenylthio group, A linear, branched or cyclic alkenylthio group such as a 23-tetracocenylthio group, a 1-cyclohexenylthio group or an n-butoxyvinylthio group,

For example, benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethylphenethyl group. , 4-
Methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-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'-methylphenyl) benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxybenzyl group, 4-n-
Butoxybenzyl group, 4-n-heptyloxybenzyl group, 4-n-decyloxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group,

3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl 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,
An aralkyl group which may have a substituent such as a 2-furfuryl group, a diphenylmethyl group, a 1-naphthylmethyl group and a 2-naphthylmethyl group,

For example, benzyloxy group, phenethyloxy group, β-methylphenethyloxy group, 4-methylphenethyloxy group, 4-methylbenzyloxy group, 3-
Methylbenzyloxy group, 2-methylbenzyloxy group, 4-ethylbenzyloxy group, 4-isopropylbenzyloxy group, 4-tert-butylbenzyloxy group,
4-cyclohexylbenzyloxy group, 4-n-octylbenzyloxy group, 4-allylbenzyloxy group, 4
-Benzylbenzyloxy group, 4-phenylbenzyloxy group, 4- (4'-methylphenyl) benzyloxy group, 4-methoxybenzyloxy group, 2-methoxybenzyloxy group, 2-ethoxybenzyloxy group, 4-n
-Butoxybenzyloxy group, 4-n-heptyloxybenzyloxy group, 4-n-decyloxybenzyloxy group, 4-n-tetradecyloxybenzyloxy group,
4-n-heptadecyloxybenzyloxy group, 3,4
-Dimethoxybenzyloxy group, 4-methoxymethylbenzyloxy group, 4-isobutoxymethylbenzyloxy group, 4-allyloxybenzyloxy group, 4-vinyloxymethylbenzyloxy group, 4-benzyloxybenzyloxy group, 4- Phenethyloxybenzyloxy group, 4-phenyloxybenzyloxy group, 3-phenyloxybenzyloxy group, 4-hydroxybenzyloxy group, 4-fluorobenzyloxy group, 4-chlorobenzyloxy group, 3-chlorobenzyloxy group, 3,4
An aralkyloxy group which may have a substituent such as a dichlorobenzyloxy group, a 1-naphthylmethyloxy group or a 2-naphthylmethyloxy group,

For example, benzylthio group, phenethylthio group, β-methylphenethyloxy group, 4-methylphenethylthio group, 4-methylbenzylthio group, 3-methylbenzylthio group, 4-ethylbenzylthio group, 4-isopropyl Benzylthio group, 4-tert-butylbenzylthio group, 4-cyclohexylbenzylthio group, 4-n-octylbenzylthio group, 4-allylbenzylthio group, 4-
Benzylbenzylthio group, 4-phenylbenzylthio group, 4- (4'-methylphenyl) benzylthio group, 4
-Methoxybenzylthio group, 2-methoxybenzylthio group, 2-ethoxybenzylthio group, 4-n-butoxybenzylthio group, 4-n-heptyloxybenzylthio group, 4-n-decyloxybenzylthio group, 4 -N-tetradecyloxybenzylthio group, 4-n-heptadecyloxybenzylthio group, 3,4-dimethoxybenzylthio group, 4-methoxymethylbenzylthio group, 4-allyloxybenzylthio group, 4-benzyloxy Benzylthio group, 4-phenethyloxybenzylthio group, 4-phenyloxybenzylthio group, 3-phenyloxybenzylthio group, 4-hydroxybenzylthio group, 4-fluorobenzylthio group, 4-chlorobenzylthio group, 1 −
Aralkylthio groups which may have a substituent such as naphthylmethylthio group and 2-naphthylmethylthio group, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 2
-Anthracenyl group, 9-anthracenyl group, 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-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 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-tetramethylphenyl group, 5-
Indanyl group, 1,2,3,4-tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group,

4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 2-ethoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2- Isopropoxyphenyl group, 4-n-butoxyphenyl group,
4-isobutoxyphenyl group, 2-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 2-neo Pentyloxyphenyl 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-n-hexadecyloxyphenyl group, 4-n-octadecyloxyphenyl group, 4-cyclohexyloxyphenyl group,
2-cyclohexyloxyphenyl group, 2-methoxy-
1-naphthyl group, 4-methoxy-1-naphthyl group, 4-
n-butoxy-1-naphthyl group, 5-ethoxy-1-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,

2,3-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-butoxyphenyl 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-trichlorophenyl group, 2,3,6
-Tribromophenyl group, 3,4,5-trifluorophenyl group, 2,4-dichloro-1-naphthyl group, 1,6
-Dichloro-2-naphthyl group,

2-fluoro-4-methylphenyl group, 2
-Fluoro-5-methylphenyl group, 3-fluoro-2
-Methylphenyl group, 3-fluoro-4-methylphenyl group, 4-fluoro-2-methylphenyl group, 5-fluoro-2-methylphenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5 -Methylphenyl group, 2-
Chloro-6-methylphenyl group, 3-chloro-2-methylphenyl group, 4-chloro-2-methylphenyl group, 4
-Chloro-3-methylphenyl group, 2-chloro-4,6
-Dimethylphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3
-Fluoro-4-ethoxyphenyl group, 5-chloro-2
-Methoxyphenyl group, 6-chloro-3-methoxyphenyl group, 5-chloro-2,4-dimethoxyphenyl group,
2-chloro-4-nitrophenyl group, 4-chloro-2-
Nitrophenyl group, 4-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 2-trifluoromethylphenyl group, 3,5-bis (trifluoromethyl) phenyl group, 4-trifluoromethyloxyphenyl group,

4-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-butoxymethylphenyl group, 3-methoxymethylphenyl group, 4- (2'-methoxyethyl) phenyl group, 4- (2 ' -Ethoxyethyloxy) phenyl group, 4- (2'-n-butoxyethyloxy) phenyl group, 4- (3'-ethoxypropyloxy) phenyl group, 4-vinyloxyphenyl group, 4
-Allyloxyphenyl group, 3-allyloxyphenyl group, 4- (4'-pentenyloxy) phenyl group, 4-
Allyloxy-1-naphthyl group, 4-allyloxymethylphenyl group, 4- (2′-allyloxyethyloxy) phenyl group,

4-benzyloxyphenyl group, 2-benzyloxyphenyl group, 4-phenethyloxyphenyl group, 4- (4'-chlorobenzyloxy) phenyl group,
4- (4'-methylbenzyloxy) phenyl group, 4-
(4'-methoxybenzyloxy) phenyl group, 4-
(3′-Ethoxybenzyloxy) phenyl group, 4-benzyloxy-1-naphthyl group, 5- (4′-methylbenzyloxy) -1-naphthyl group, 6-benzyloxy-2-naphthyl group, 6- ( 4'-methylbenzyloxy) -2-naphthyl group, 7-benzyloxy-2-naphthyl group, 4- (benzyloxymethyl) phenyl group, 4
A-(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 '
-Phenyloxyethyloxy) phenyl group, 4-
[2 '-(4'-methylphenyloxy) ethyloxy] phenyl group, 4- [2'-(4'-methoxyphenyloxy) ethyloxy] phenyl group, 4- [2'-
(4'-Chlorophenyloxy) ethyloxy] 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-
Allylcarbonylphenyl group, 4-benzylcarbonylphenyl group, 4- (4'-methylbenzyl) carbonylphenyl group, 4-phenylcarbonylphenyl group, 4-
(4'-methylphenyl) carbonylphenyl group, 4-
(4'-chlorophenyl) carbonylphenyl group, 4-
Phenylcarbonyl-1-naphthyl group,

4-methoxycarbonylphenyl group, 2-
Methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4
-N-propoxycarbonylphenyl group, 4-n-butoxycarbonylphenyl group, 4-n-hexyloxycarbonylphenyl group, 4-n-decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonyl- 1-naphthyl group, 6
-Methoxycarbonyl-2-naphthyl group, 6-n-butoxycarbonyl-2-naphthyl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4'-chlorobenzyl) oxycarbonylphenyl group , 4-phenethyloxycarbonylphenyl group, 6-benzyloxycarbonyl-2-naphthyl group, 4-phenyloxycarbonylphenyl group, 4-
(4'-Ethylphenyl) oxycarbonylphenyl group, 4- (4'-chlorophenyl) oxycarbonylphenyl group, 4- (4'-ethoxyphenyl) oxycarbonylphenyl group, 6-phenyloxycarbonyl-2
-Naphthyl group,

4-acetyloxyphenyl group, 3-acetyloxyphenyl group, 2-acetyloxyphenyl group, 4-ethylcarbonyloxyphenyl group, 2-ethylcarbonyloxyphenyl group, 4-n-propylcarbonyloxyphenyl group, 4-n-pentylcarbonyloxyphenyl group, 4-n-octylcarbonyloxyphenyl group, 4-cyclohexylcarbonyloxyphenyl group, 3-cyclohexylcarbonyloxyphenyl group, 4-acetyloxy-1-naphthyl group, 4-n- Butylcarbonyloxy-1-naphthyl group, 5-acetyloxy-1-naphthyl group, 6-ethylcarbonyloxy-2-naphthyl group, 7-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4- Benzyl carbonyl oki Phenyl group, 4-phenethylcarbonyloxyphenyl group, 6-benzylcarbonyloxy-2-naphthyl group, 4-phenylcarbonyloxyphenyl group, 4- (4'-methylphenyl) carbonyloxyphenyl group, 4- (2'- Methylphenyl) carbonyloxyphenyl group, 4- (4'-chlorophenyl)
Carbonyloxyphenyl group, 4- (2'-chlorophenyl) carbonyloxyphenyl group, 4-phenylcarbonyloxy-1-naphthyl group, 6-phenylcarbonyloxy-2-naphthyl group, 7-phenylcarbonyloxy-2-naphthyl group ,

4-methylthiophenyl group, 2-methylthiophenyl group, 2-ethylthiophenyl group, 3-ethylthiophenyl group, 4-n-propylthiophenyl group, 2
-Isopropylthiophenyl group, 4-n-butylthiophenyl group, 2-isobutylthiophenyl group, 2-neopentylphenyl group, 4-n-hexylthiophenyl group,
4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group, 4-benzylthiophenyl group, 3-benzylthiophenyl group, 2-benzylthiophenyl group,
4- (4'-chlorobenzylthio) phenyl group, 4-phenylthiophenyl group, 3-phenylthiophenyl group,
2-phenylthiophenyl group, 4- (4'-methylphenylthio) phenyl group, 4- (3'-methylphenylthio) phenyl group, 4- (4'-methoxyphenylthio)
Phenyl group, 4- (4'-chlorophenylthio) phenyl group, 2-ethylthio-1-naphthyl group, 4-methylthio-1-naphthyl group, 6-ethylthio-2-naphthyl group, 6-phenylthio-2-naphthyl group ,

4-nitrophenyl group, 3-nitrophenyl group, 2-nitrophenyl group, 3,5-dinitrophenyl group, 4-nitro-1-naphthyl group, 4-formylphenyl group, 3-formylphenyl group, 2-formylphenyl group, 4-formyl-1-naphthyl group, 1-formyl-
2-naphthyl group,

4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morpholinophenyl group, 4- (N
-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- (N-n-octylamino) phenyl group, 4- (N-n-dodecylamino) phenyl group, 4-
(N-benzylamino) phenyl group, 4- (N-phenylamino) phenyl group, 2- (N-phenylamino) phenyl group,

4- (N, N-dimethylamino) phenyl group, 3- (N, N-dimethylamino) phenyl group, 4-
(N, N-diethylamino) phenyl group, 2- (N, N
-Dimethylamino) phenyl group, 2- (N, N-diethylamino) phenyl group, 4- (N, N-di-n-butylamino) phenyl group, 4- (N, N-di-n-hexylamino) Phenyl group, 4- (N-cyclohexyl-N-
Methylamino) phenyl group, 4- (N, N-diethylamino) -1-naphthyl group, 4- (N-benzyl-N-phenylamino) phenyl group, 4- (N, N-diphenylamino) phenyl group, 4 -[N-phenyl-N- (4-
Methylphenyl) amino] phenyl group, 4- [N, N-
Di (3'-methylphenyl) amino] phenyl group, 4-
[N, N-di (4′-methylphenyl) amino] phenyl group, 4- [N, N-di (4′-methoxyphenyl) amino] phenyl group, 2- (N, N-diphenylamino)
Phenyl group,

4-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
An aryl group which may have a substituent such as a cyano-2-naphthyl group,

For example, phenyloxy group, 2-methylphenyloxy group, 3-methylphenyloxy group, 4-methylphenyloxy group, 4-ethylphenyloxy group,
4-n-propylphenyloxy group, 4-isopropylphenyloxy group, 4-n-butylphenyloxy group,
4-tert-butylphenyloxy group, 4-isopentylphenyloxy group, 4-tert-pentylphenyloxy group, 4-n-hexylphenyloxy group, 4-cyclohexylphenyloxy group, 4-n-octylphenyloxy group , 4-n-decylphenyloxy group, 4-n-octadecylphenyloxy group,

2,3-dimethylphenyloxy group, 2,
4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 5
-Indanyloxy group, 1,2,3,4-tetrahydro-5-naphthyloxy group, 1,2,3,4-tetrahydro-6-naphthyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group Group, 4-methoxyphenyloxy group, 3-ethoxyphenyloxy group, 4-
Ethoxyphenyloxy group, 4-n-propoxyphenyloxy group, 4-isopropoxyphenyloxy group, 4
-N-butoxyphenyloxy group, 4-n-pentyloxyphenyloxy group, 4-n-hexyloxyphenyloxy group, 4-cyclohexyloxyphenyloxy group, 4-n-heptyloxyphenyloxy group, 4-n
-Octyloxyphenyloxy group, 4-n-decyloxyphenyloxy group, 2,3-dimethoxyphenyloxy group, 2,5-dimethoxyphenyloxy group, 3,4
-Dimethoxyphenyloxy group, 2-methoxy-5-methylphenyloxy group, 3-methyl-4-methoxyphenyloxy group, 2-fluorophenyloxy group, 3-fluorophenyloxy group, 4-fluorophenyloxy group, 2 -Chlorophenyloxy group, 3-chlorophenyloxy group, 4-chlorophenyloxy group, 4-bromophenyloxy group, 4-trifluoromethylphenyloxy group, 3,4-dichlorophenyloxy group, 2-methyl-4-chlorophenyloxy group , 2-chloro-4-methylphenyloxy group, 3-chloro-4-methylphenyloxy group, 2-chloro-4-methoxyphenyloxy group, 4-phenylphenyloxy group, 3-phenylphenyloxy group, 4- (4'-methylphenyl) phenyloxy group, 4- (4 ' Methoxyphenyl) phenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-ethoxy-1-naphthyloxy group, 6-methoxy-2-naphthyloxy group, 7-ethoxy-2-naphthyloxy group, 2 -Furyloxy group, 2-thienyloxy group, 3-thienyloxy group, 2-pyridyloxy group, 3
An aryloxy group which may have a substituent such as a -pyridyloxy group or a 4-pyridyloxy group,

For example, phenylthio group, 3-methylphenylthio group, 4-methylphenylthio group, 4-ethylphenylthio group, 4-n-propylphenylthio group, 4-
n-butylphenylthio group, 4-tert-butylphenylthio group, 4-n-hexylphenylthio group, 4-cyclohexylphenylthio group, 4-n-octylphenylthio group, 4-n-dodecylphenylthio group, 4-n-octadecylphenylthio group, 2,3-dimethylphenylthio group, 3,4-dimethylphenylthio group, 3-methoxyphenylthio group, 4-methoxyphenylthio group, 3-ethoxyphenylthio group, 4- Ethoxyphenylthio group,
4-n-propoxyphenylthio group, 4-n-butoxyphenylthio group, 4-n-hexyloxyphenylthio group, 4-n-octyloxyphenylthio group, 4-n-
Decyloxyphenylthio group, 3,4-dimethoxyphenylthio group, 3-methyl-4-methoxyphenylthio group, 3-fluorophenylthio group, 4-fluorophenylthio group, 4-chlorophenylthio group, 2-methyl- Four
-Chlorophenylthio group, 2-chloro-4-methoxyphenylthio group, 4-phenylphenylthio group, 4-
(4'-methylphenyl) phenylthio group, 4- (4 '
-Methoxyphenyl) phenylthio group, 1-naphthylthio group, arylthio group which may have a substituent such as 2-naphthylthio group, cyano group, hydroxyl group, nitro group,

For example, carboxyl group, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, n-octyl group. Oxycarbonyl group, 2-ethylhexyloxycarbonyl group, n-decyloxycarbonyl group, n-dodecyloxycarbonyl group, n-tetradecyloxycarbonyl group, n-hexadecyloxycarbonyl group, n-octadecyloxycarbonyl group, cyclohexyloxy Carbonyl group,

Benzyloxycarbonyl group, phenethyloxycarbonyl group, (4-methylbenzyloxy) carbonyl group, (3-methylbenzyloxy) carbonyl group, (4-tert-butylbenzyloxy) carbonyl group, (4-methoxybenzyl) An oxy) carbonyl group,
(4-chlorobenzyloxy) carbonyl group, phenyloxycarbonyl group, (4-methylphenyloxy) carbonyl group, (3-methylphenyloxy) carbonyl group, (4-ethylphenyloxy) carbonyl group, (4
-Tert-butylphenyloxy) carbonyl group, (4-
-COOR ₁ group such as (methoxyphenyloxy) carbonyl group, (2-methoxyphenyloxy) carbonyl group, (4-ethoxyphenyloxy) carbonyl group, (4-fluorophenyloxy) carbonyl group (in the group, R ₁
Represents the same meaning as above),

For example, formyl group, methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group,
n-butylcarbonyl group, n-hexylcarbonyl group,
n-octylcarbonyl group, 2-ethylhexylcarbonyl group, n-decylcarbonyl group, n-dodecylcarbonyl group, n-tetradecylcarbonyl group, n-hexadecylcarbonyl group, n-octadecylcarbonyl group, cyclohexylcarbonyl group, benzylcarbonyl Group, phenethylcarbonyl group, (4-methylbenzyl) carbonyl group, (4-tert-butylbenzyl) carbonyl group,
(4-methoxybenzyl) carbonyl group, (4-chlorobenzyl) carbonyl group, phenylcarbonyl group, (4
-Methylphenyl) carbonyl group, (3-methylphenyl) carbonyl group, (4-ethylphenyl) carbonyl group, (4-tert-butylphenyl) carbonyl group, (4
-Methoxyphenyl) carbonyl group, (2-methoxyphenyl) carbonyl group, (4-ethoxyphenyl) carbonyl group, (4-fluorophenyl) carbonyl group, amide, substituted amide and the like -COR ₂ group (in the group, R ₂ Represents the same meaning as above),

For example, methylcarbonyloxy group, ethylcarbonyloxy group, n-propylcarbonyloxy group, n-butylcarbonyloxy group, n-pentylcarbonyloxy group, n-hexylcarbonyloxy group, n
-Octylcarbonyloxy group, 2-ethylhexylcarbonyloxy group, n-decylcarbonyloxy group, n
-Dodecylcarbonyloxy group, n-tetradecylcarbonyloxy group, n-hexadecylcarbonyloxy group, n-octadecylcarbonyloxy group, cyclohexylcarbonyloxy group, benzylcarbonyloxy group, phenethylcarbonyloxy group, (4'-methylbenzyl Carbonyl) oxy group, (4′-tert-butylbenzylcarbonyl) oxy group, (4′-methoxybenzylcarbonyl) oxy group, (4′-chlorobenzylcarbonyl) oxy group, phenylcarbonyloxy group,
(4'-methylphenylcarbonyl) oxy group, (3 '
-Methylphenylcarbonyl) oxy group, (4'-ethylphenylcarbonyl) oxy group, (4'-tert-butylphenylcarbonyl) oxy group, (4'-methoxyphenylcarbonyl) oxy group, (2'-methoxyphenylcarbonyl) ) An oxy group, a (4′-ethoxyphenylcarbonyl) oxy group, a (4′-fluorophenylcarbonyl) oxy group and the like, —OCOR ₃ group (in which R ₃ has the same meaning as described above), an amino group, N -Methylamino group, N-ethylamino group, N-isopropylamino group,
N-n-butylamino group, N-n-hexylamino group,
N-n-decylamino group, N-n-tetradecylamino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-di-n-butylamino group, N, N-di-
n-hexylamino group, N, N-di-n-dodecylamino group, N-phenylamino group, N- (4-methylphenyl) amino group, N, N-diphenylamino group, N-methyl-N-phenyl Amino group, N-n-butyl-N-phenylamino group, N, N-di-1-naphthylamino group,
N, N-di-2-naphthylamino group, N-phenyl-N
-1-naphthylamino group, N-phenyl-N-2-naphthylamino group, N-1-naphthyl-N-2'-naphthylamino group, N-phenyl-N-9-anthracenylamino group, N- Phenyl-N-2-anthracenyl group, N-
Phenyl-N-9-phenanthrenyl group, N-phenyl-N-1-pyrenyl group, N-1-naphthyl-N-2'-
Anthracenyl group, N-1-naphthyl-N-9'-anthracenyl group, N-1-naphthyl-N-9'-phenanthrenyl group, N-1-naphthyl-N-1'-pyrenyl group, N-2-naphthyl -N-9'-anthracenyl group,
N-2-naphthyl-N-9'-phenanthrenyl group, N
-2-naphthyl-N-1'-pyrenyl group, N-2-naphthyl-N-2-quinolinyl group, N, N-di (4-ethylphenyl) amino group, N, N-di (4-methoxyphenyl) ) A group represented by general formula (2) (Chemical Formula 9) such as an amino group,

[0083]

[Chemical 9]

(In the group, Y ₁ and Y ₂ have the same meanings as described above).

In the formula (2), Y ₁ and Y ₂ are a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted It represents an unsubstituted aryl group, and Y ₁ and Y ₂ may combine with each other to form a substituted or unsubstituted aromatic ring or aliphatic ring together with a nitrogen atom.

Specific examples of the linear, branched or cyclic alkyl group which may have a substituent of Y ₁ and Y ₂ , a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group include: X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅
And a straight chain, branched or cyclic alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted group which is mentioned as a specific example of the group represented by A _{21 to} A ₂₅ . The example of an aryl group can be given.

At least one of A _{11 to} A ₁₅ and A _{21 to} A
_At least one of ₂₅ is a group represented by the formula (2),
Preferably, a formula (2) in which Y ₁ and Y ₂ are a linear, branched or cyclic alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group ) Is a group represented by the formula (2), more preferably a group represented by the formula (2) in which Y ₁ and Y ₂ are substituted or unsubstituted aryl groups.

The amino compound represented by the general formula (1) of the present invention has the following formula (1) depending on the substitution position of the group represented by the formula (2).
0) 9 structures.

[0089]

[Chemical 10]

[Wherein, Q ₁ and Q ₂ represent a group represented by the formula (2), X ₁ , X ₂ , X ₃ and X ₄ , A _{11 to} A ₁₅ and A _{21 to} A ₂₅ are as described above. Preferably represents (1-A1), (1-B2), (1-B3), (1-C2) and (1
-C3), and more preferably (1-B3), (1-C2) and (1
-C3). In addition, general formula (1-A1) ~ (1-A3), (1-B1) ~
In the amine compounds represented by (1-B3) and (1-C1) to (1-C3), Q ₁ and Q ₂ may be the same or different.

The amino acid represented by the general formula (1) according to the present invention
Specific examples of the compound include, for example, the compounds shown below.
However, the present invention is not limited to these.
Not a thing. 1.1,2-bis (N-phenyl-N-2 "-naphthyl
-4'-aminophenyl) -3,4,5,6-tetraf
Phenylbenzene 2.1,2-bis (N, N-diphenyl-4′-amino)
Phenyl) -3,4,5,6-tetraphenylbenzene 3.1,2-bis (N, N-di-2 "-naphthyl-4 '
-Aminophenyl) -3,4,5,6-tetraphenyl
Benzene 4.1,2-bis (N, N-di-1 "-naphthyl-4 '
-Aminophenyl) -3,4,5,6-tetraphenyl
Benzene 5.1,2-bis (N-phenyl-N-1 "-naphthyl
-4'-aminophenyl) -3,4,5,6-tetraf
Phenylbenzene 6.1,2-bis (N-phenyl-N-4 "-phenyl
Phenyl-4′-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 7.1,2-bis (N-phenyl-N-3 "-phenyl
Phenyl-4′-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 8.1,2-bis (N-phenyl-N-2 "-phenyl
Phenyl-4′-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 9.1,2-bis (N-phenyl-N-4 "-cyclohexyl
Xylphenyl-4'-aminophenyl) -3,4
5,6-Tetraphenylbenzene 10.1,2-bis (N-phenyl-N-3 "-cyclo
Hexylphenyl-4'-aminophenyl) -3,4
5,6-Tetraphenylbenzene 11.1,2-bis (N-phenyl-N-2 "-ant
Racenyl-4'-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 12.1,2-bis (N-phenyl-N-9 "-ant
Racenyl-4'-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 13.1,2-bis (N-phenyl-N-9 "-phena
Ntrenyl-4'-aminophenyl) -3,4,5,6
-Tetraphenylbenzene 14.1,2-bis (N-phenyl-N-2 "-quinoli
Nyl-4′-aminophenyl) -3,4,5,6-teto
Laphenylbenzene 15.1,2-bis (N-phenyl-N-1 "-pyrene
Ru-4'-aminophenyl) -3,4,5,6-tetra
Phenylbenzene 16.1,2-bis (N-2 "-naphthyl-N-4"'
-Phenylphenyl-4'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 17.1,2-bis (N-2 "-naphthyl-N-4"'
-Cyclohexylphenyl-4'-aminophenyl)-
3,4,5,6-Tetraphenylbenzene 18.1,2-bis (N-2 "-naphthyl-N-1"'
-Naphthyl-4'-aminophenyl) -3,4,5,6
-Tetraphenylbenzene 19.1,2-bis (N-2 "-naphthyl-N-9"'
-Anthracenyl-4'-aminophenyl) -3,4
5,6-Tetraphenylbenzene 20.1,2-bis (N-2 "-naphthyl-N-9"'
-Phenanthrenyl-4'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 21.1,2-bis (N-2 "-naphthyl-N-9"'
-Pyrenyl-4'-aminophenyl) -3,4,5,6
-Tetraphenylbenzene 22.1,2-bis (N-1 "-naphthyl-N-4"'
-Phenylphenyl-4'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 23.1,2-bis (N-1 "-naphthyl-N-4"'
-Cyclohexylphenyl-4'-aminophenyl)-
3,4,5,6-Tetraphenylbenzene 24.1,2-bis (N-1 "-naphthyl-N-2"'
-Phenylphenyl-4'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 25.1,2-bis (N-1 "-naphthyl-N-9"'
-Anthracenyl-4'-aminophenyl) -3,4
5,6-Tetraphenylbenzene 25.1,2-bis (N-1 "-naphthyl-N-9"'
-Phenanthrenyl-4'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 26.1,2-bis (N-1 "-naphthyl-N-1"'
-Pyrenyl-4'-aminophenyl) -3,4,5,6
-Tetraphenylbenzene 27.1,2-bis (N-phenyl-N-2 "-naphthyl
Ru-3'-aminophenyl) -3,4,5,6-tetra
Phenylbenzene 28.1,2-bis (N-phenyl-N-2 "-naphthyl
Ru-2'-aminophenyl) -3,4,5,6-tetra
Phenylbenzene 29.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-3'-aminophenyl) -3,4,5,6-tetra
Phenylbenzene 30.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-2'-aminophenyl) -3,4,5,6-tetra
Phenylbenzene 31.1,2-bis (N-3 "-methylphenyl-N-
1 "'-naphthyl-4'-aminophenyl) -3,4
5,6-Tetraphenylbenzene 32.1,2-bis (N-2 ", 5" -dimethylphenyl
Ru-N-2 "'-naphthyl-4'-aminophenyl)-
3,4,5,6-Tetraphenylbenzene 33.1,2-bis (N-3 "-ethoxyphenyl-N
-1 "'-naphthyl-4'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 34.1,2-bis (N-2 "-fluorophenyl-N
-1 "'-naphthyl-4'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 35.1,2-bis (N-methyl-N-1 "-naphthyl
-4'-aminophenyl) -3,4,5,6-tetraf
Phenylbenzene 36.1,2-bis (Nn-butyl-N-1 "-naphth
Tyl-4′-aminophenyl) -3,4,5,6-teto
Raphenylbenzene 37.1,2-bis (N-benzyl-N-1 "-naphthyl
Ru-4'-aminophenyl) -3,4,5,6-tetra
Phenylbenzene 38.1,2-bis (N-cyclohexyl-N-1 "-
Naphthyl-4'-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 39.1,2-bis (N-isopropyl-N-2 "-na
Futyl-4'-aminophenyl) -3,4,5,6-te
Traphenylbenzene 40.1,2-bis (N-phenyl-4′-aminophen)
Nyl) -3,4,5,6-tetraphenylbenzene 41.1,2-bis (N-1 "-naphthyl-4'-ami
Nophenyl) -3,4,5,6-tetraphenylbenze
42.1,2-bis (Nn-hexyl-4′-amino)
Phenyl) -3,4,5,6-tetraphenylbenzene 43.1,2-bis (N-4 "-bromobenzyl-4 '
-Aminophenyl) -3,4,5,6-tetraphenyl
Benzene 44.1,2-bis (4'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 45.1,2-bis (3'-aminophenyl) -3,
4,5,6-tetraphenylbenzene 46.1,2-bis (2'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 47.1,2-bis (N-phenyl-N-2 "-naphthyl
Ru-4'-amino-1'-naphthyl) -3,4,5,6
-Tetraphenylbenzene 48.1,2-bis (N, N-diphenyl-4'-ami
No-1'-naphthyl) -3,4,5,6-tetrapheni
Rubenzene 49.1,2-bis (N, N-diphenyl-4′-ami)
No-1'-naphthyl) -3,4,5,6-tetrapheni
Rubenzene 50.1,2-bis (N, N-di-2 "-naphthyl-
4'-amino-2'-naphthyl) -3,4,5,6-te
Traphenylbenzene 51.1,2-bis (N, N-di-1 ″ -naphthyl-
4'-amino-1'-naphthyl) -3,4,5,6-te
Traphenylbenzene 52.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-3'-amino-2'-naphthyl) -3,4,5,6
-Tetraphenylbenzene 53.1,2-bis (N-phenyl-N-4 "-phenyl
Ruphenyl-4'-amino-1'-naphthyl) -3,
4,5,6-Tetraphenylbenzene 54.1,2-bis (N-phenyl-N-3 "-phenyl
Ruphenyl-3'-amino-2'-naphthyl) -3,
4,5,6-Tetraphenylbenzene 55.1,2-bis (N-phenyl-N-2 "-phenyl
Ruphenyl-2'-amino-1'-naphthyl) -3,
4,5,6-Tetraphenylbenzene 56.1,2-bis (N-phenyl-N-4 "-cyclo
Hexylphenyl-3'-amino-2'-naphthyl)-
3,4,5,6-Tetraphenylbenzene 57.1,2-bis (N-phenyl-N-3 "-cyclo
Hexylphenyl-4'-amino-1'-naphthyl)-
3,4,5,6-Tetraphenylbenzene 58.1,2-bis (N-phenyl-N-2 "-ant
Racenyl-3'-amino-1'-naphthyl) -3,4
5,6-Tetraphenylbenzene 59.1,2-bis (N-phenyl-N-9 "-ant
Racenyl-3'-amino-2'-naphthyl) -3,4
5,6-Tetraphenylbenzene 60.1,2-bis (N-phenyl-N-9 "-phena
Ntrenyl-4'-amino-1'-naphthyl) -3,
4,5,6-Tetraphenylbenzene 61.1,2-bis (N-2 "-naphthyl-N-4"'
-Phenylphenyl-4'-amino-1'-naphthyl)
-3,4,5,6-tetraphenylbenzene 62.1,2-bis (N-2 "-naphthyl-N-4"'
-Cyclohexylphenyl-4'-amino-1'-naphth
Cyl) -3,4,5,6-tetraphenylbenzene 63.1,2-bis (N-2 "-naphthyl-N-1"'
-Naphthyl-4'-amino-1'-naphthyl) -3,
4,5,6-Tetraphenylbenzene 64.1,2-bis (N-1 "-naphthyl-N-4"'
-Phenylphenyl-4'-amino-1'-naphthyl)
-3,4,5,6-Tetraphenylbenzene 65.1,2-bis (N-1 "-naphthyl-N-4"'
-Cyclohexylphenyl-4'-amino-1'-na
Futyl) -3,4,5,6-tetraphenylbenzene 66.1,2-bis (N-1 "-naphthyl-N-2"'
-Phenylphenyl-4'-amino-1'-naphthyl)
-3,4,5,6-Tetraphenylbenzene 67.1,2-bis (N-1 "-naphthyl-N-9"'
-Anthracenyl-4'-amino-1'-naphthyl)
-3,4,5,6-Tetraphenylbenzene 68.1,2-bis (N-1 "-naphthyl-N-9"'
-Phenanthrenyl-4'-amino-1'-naphthyl)
-3,4,5,6-Tetraphenylbenzene 69.1,2-bis (N-phenyl-N-2 "-naphthyl
Ru-9'-amino-10'-anthracenyl) -3,
4,5,6-Tetraphenylbenzene 70.1,2-bis (N-phenyl-N-2 "-naphthyl
Ru-4'-amino-1'-naphthyl) -3,4,5,6
-Tetraphenylbenzene 71.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-9'-amino-10'-anthracenyl) -3,
4,5,6-Tetraphenylbenzene 72.1,2-bis (N-3 "-methylphenyl-N-
1 "'-naphthyl-4'-amino-1'-naphthyl)
-3,4,5,6-Tetraphenylbenzene 73.1,2-bis (N-2 ", 5" -dimethylphenyl
Ru-N-2 "'-naphthyl-4'-amino-1'-na
Futyl) -3,4,5,6-tetraphenylbenzene 74.1,2-bis (N-methyl-N-1 "-naphthyl
-4'-amino-1'-naphthyl) -3,4,5,6
-Tetraphenylbenzene 75.1,2-bis (Nn-butyl-N-1 "-naphth
Tyl-4'-amino-1'-naphthyl) -3,4
5,6-Tetraphenylbenzene 76.1,2-bis (N-benzyl-N-1 "-naphthyl
Ru-4'-amino-1'-naphthyl) -3,4,5,
6-Tetraphenylbenzene 77.1,2-bis (N-cyclohexyl-N-1 "-
Naphthyl-4'-amino-1'-naphthyl) -3,
4,5,6-Tetraphenylbenzene 78.1,2-bis (N-isopropyl-N-2 "-na
Futyl-4'-amino-1'-naphthyl) -3,4
5,6-Tetraphenylbenzene 79.1,2-bis (N-phenyl-4'-amino-
1'-naphthyl) -3,4,5,6-tetraphenylbe
Nzen 80.1,2-bis (N-1 "-naphthyl-9'-ami
No-10′-anthracenyl) -3,4,5,6-teto
Raphenylbenzene 81.1,2-bis (Nn-hexyl-4′-amino)
-1'-naphthyl) -3,4,5,6-tetraphenyl
Benzene 82.1,2-bis (N-4 "-fluorobenzyl-
4'-amino-1'-naphthyl) -3,4,5,6-te
Traphenylbenzene 83.1,2-bis (4'-amino-1'-naphthyl)
-3,4,5,6-Tetraphenylbenzene 84.1,2-bis (9'-amino-10'-anthra
Cenyl) -3,4,5,6-tetraphenylbenzene 85.1,2-bis (N-phenyl-N-2 "-naphthyl
Ru-4'-amino-2 ', 5'-dimethylphenyl)-
3,4,5,6-Tetraphenylbenzene 86.1,2-bis (N-phenyl-N-2 "-naphthyl
Ru-3'-amino-5'-phenylphenyl) -3,
4,5,6-Tetraphenylbenzene 87.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-4'-amino-2'-phenylphenyl) -3,
4,5,6-Tetraphenylbenzene 88.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-4'-amino-2'-tert-butylphenyl)-
3,4,5,6-Tetraphenylbenzene 89.1,2-bis (N-phenyl-N-4 "-phenyl
Luphenyl-2'-amino-4'-tert-butylpheny
) -3,4,5,6-Tetraphenylbenzene 90.1,2-bis (N-phenyl-N-9 "-phena
Nthrenyl-4'-amino-5'-benzyloxyphene
Nyl) -3,4,5,6-tetraphenylbenzene 91.1,2-bis (N, N-di-1 "-naphthyl-
4'-amino-2'-methyl-1'-naphthyl) -3,
4,5,6-Tetraphenylbenzene 92.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-4'-aminophenyl) -4,5-diphenylben
Zen 93.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-4'-aminophenyl) -3,6-diphenylben
Zen 94.1,2-bis (N-phenyl-N-1 "-naphthyl
Lu-4'-aminophenyl) benzene 95.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-4'-aminophenyl) -4,5-dimethylbenze
96.1,2-bis (N-phenyl-N-1 "-naphthy
Ru-4'-aminophenyl) -3-fluoro-4,5,
6-triphenylbenzene 97.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-4'-aminophenyl) -3,6-dicyanobenze
98.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-4'-aminophenyl) -3,6-di-tert-butyl
Benzene 99.1,2-bis (N-phenyl-N-1 "-naphthyl
Ru-4'-aminophenyl) -3,6-dicyclohexyl
Le-4,5-diphenylbenzene 100.1,2-bis (N-phenyl-N-1 "-naphth
Cyl-4′-aminophenyl) -3,5-di-n-noni
Rubenzene 101.1,2-bis (N-phenyl-N-1 "-naphth
Cyl-4'-aminophenyl) -3,6-diphenyl-
4,5-Dimethylbenzene 102.1,2-bis (N-phenyl-N-1 "-naphth
Tyl-4'-aminophenyl) -3,6-di (4 "'-
Phenylphenyl) -4,5-diphenylbenzene 103.1,2-bis (N-phenyl-N-1 "-naphth
Tyl-4'-aminophenyl) -3,6-di (4 "'-
Methylphenyl) -4,5-diphenylbenzene 104.1,2-bis (N-phenyl-N-1 "-naphth
Tyl-4'-aminophenyl) -3,6-di (4 "'-
Fluorophenyl) -4,5-diphenylbenzene 105.1,2-bis (N-phenyl-N-1 "-naphth
Tyl-4'-aminophenyl) -3,6-di (3 "'-
Ethoxyphenyl) -4,5-diphenylbenzene 106.1,2-bis (N-phenyl-N-1 "-naphth
Cyl-4'-aminophenyl) -3,6-diphenyl-
4,5-di (4 "'-benzyloxyphenyl) benze
107.1,2-bis (N-phenyl-N-1 "-naphth
Tyl-4'-aminophenyl) -3,6-di (3 "'-
Phenylphenyl) -4,5-diphenylbenzene 108.1,2-bis (N-phenyl-N-1 "-naphth
Tyl-4'-aminophenyl) -3,6-di (1 "'-na
Futyl) -4,5-diphenylbenzene 109.1,2-bis (N-phenyl-N-1 "-naphth
Tyl-4′-aminophenyl) -3-phenylbenzene 110.1- (N-phenyl-N-2 ″ -naphthyl-
4'-aminophenyl) -2- (N'-phenyl-N '
-1 ""-naphthyl-4 "'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 111.1- (N, N-diphenyl-4'-aminophen
Nyl) -2- (N ', N'-diphenyl-3-amino
Phenyl) -3,4,5,6-tetraphenylbenzene 112.1- (N, N-di-2 "-naphthyl-4'-a
Minophenyl) -2- (N ', N'-diphenyl-
4 "'-aminophenyl) -3,4,5,6-tetraf
Phenylbenzene 113.1- (N, N-di-1 ″ -naphthyl-4′-a
Minophenyl) -2- (N ', N'-diphenyl-
3 "'-aminophenyl) -3,4,5,6-tetraf
Phenylbenzene 114.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N'-phenyl-
4 "'-aminophenyl) -3,4,5,6-tetraf
Phenylbenzene 115.1- (N-phenyl-N-4 "-phenylphene
Nyl-4'-aminophenyl) -2- (N'-phenyl
-N'-4 ""-phenylphenyl-3 "'-aminoph
Phenyl) -3,4,5,6-tetraphenylbenzene 116.1- (N-phenyl-N-3 "-phenylphen
Nyl-4'-aminophenyl) -2- (N'-phenyl
-N'-1 ""-naphthyl-4 "'-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 117.1- (N-phenyl-N-2 "-phenylphen
Nyl-4′-aminophenyl) -2- (N ′, N′-di
Phenyl-"'-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 118.1- (N-phenyl-N-4 "-cyclohexyl
Ruphenyl-4′-aminophenyl) -2- (N ′,
N'-diphenyl-4 "'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 119.1- (N-phenyl-N-3 "-cyclohexyl
Ruphenyl-4'-aminophenyl) -2- (N'-f
Phenyl-N'-1 ""-naphthyl-4 "'-aminophen
Nyl) -3,4,5,6-tetraphenylbenzene 120.1- (N-phenyl-N-2 "-naphthyl-
4'-aminophenyl) -2- (N'-phenyl-N '
-2 ""-naphthyl-3 "'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 121.1- (N-phenyl-N-9 "-anthraceni
Ru-4′-aminophenyl) -2- (N ′, N′-diff
Phenyl-4 "'-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 122.1- (N-phenyl-N-9 "-anthraceni
Ru-4'-aminophenyl) -2- (N'-phenyl-
N'-9 ""-anthracenyl-3 "'-aminopheni
) -3,4,5,6-Tetraphenylbenzene 123.1- (N-phenyl-N-9 "-phenanthre
Nyl-4'-aminophenyl) -2- (N'-phenyl
-N'-9 ""-phenanthrenyl-3 "'-aminoph
Phenyl) -3,4,5,6-tetraphenylbenzene 124.1- (N-phenyl-N-2 "-quinolinyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3,4,5,6-teto
Laphenylbenzene 125.1- (N-phenyl-N-1 "-pyrenyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-aminophenyl) -3,4,5,6-teto
Laphenylbenzene 126.1- (N-2 "-naphthyl-N-4"'-phen
Nylphenyl-4′-aminophenyl) -2- (N ′,
N'-diphenyl-4 ""-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 127.1- (N-2 "-naphthyl-N-4"'-shik
Lohexylphenyl-4'-aminophenyl) -2-
(N ', N'-diphenyl-4 ""-aminophenyl)
-3,4,5,6-tetraphenylbenzene 128.1- (N-2 "-naphthyl-N-1"'-naphth
Cyl-4′-aminophenyl) -2- (N ′, N′-di
-1 ""'-naphthyl-3""-aminophenyl)-
3,4,5,6-Tetraphenylbenzene 129.1- (N-2 "-naphthyl-N-9"'-an
Toracenyl-4′-aminophenyl) -2- (N ′,
N'-diphenyl-4 ""-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 130.1- (N-2 "-naphthyl-N-9"'-phen
Nanthrenyl-4'-aminophenyl) -2- (N ',
N'-di-4 ""'-phenylphenyl-4""-ami
Nophenyl) -3,4,5,6-tetraphenylbenze
131.1- (N-2 "-naphthyl-N-9"'-pyre
Nyl-4′-aminophenyl) -2- (N ′, N′-di
Phenyl-3 ""-aminophenyl) -3,4,5,6
-Tetraphenylbenzene 132.1- (N-1 "-naphthyl-N-4"'-phen
Nylphenyl-4′-aminophenyl) -2- (N ′,
N'-di-3 ""'-phenylphenyl-4""-ami
Nophenyl) -3,4,5,6-tetraphenylbenze
133.1- (N-1 "-naphthyl-N-4"'-shik
Lohexylphenyl-4'-aminophenyl) -2-
(N ', N'-diphenyl-4 ""-aminophenyl)
-3,4,5,6-tetraphenylbenzene 134.1- (N-1 "-naphthyl-N-2"'-phen
Nylphenyl-4′-aminophenyl) -2- (N ′,
N'-diphenyl-4 ""-amino-3 ""-methyl
Phenyl) -3,4,5,6-tetraphenylbenzene 135.1- (N-1 "-naphthyl-N-9"'-an
Toracenyl-4′-aminophenyl) -2- (N ′,
N'-diphenyl-4 ""-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 136.1- (N-1 "-naphthyl-N-9"'-phen
Nanthrenyl-4'-aminophenyl) -2- (N'-
1 ""'-naphthyl-N'-9"""-phenanthreni
Ru-3 """'-aminophenyl) -3,4,5,6-
Tetraphenylbenzene 137.1- (N-1 "-naphthyl-N-1"'-pyre
Nyl-4'-aminophenyl) -2- (N'-phenyl
-N'-1 ""'-pyrenyl-4""-aminopheni
) -3,4,5,6-Tetraphenylbenzene 138.1- (N-phenyl-N-2 "-naphthyl-
3'-aminophenyl) -2- (N ', N'-dipheni
Ru-2 "'-aminophenyl) -3,4,5,6-teto
Laphenylbenzene 139.1,2-bis (N-phenyl-N-2 "-naphth
Cyl-2'-aminophenyl) -2- (N ', N'-di
Phenyl-2 "'-aminophenyl) -3,4,5,6
-Tetraphenylbenzene 140.1,2-bis (N-phenyl-N-1 "-naphth
Cyl-3'-aminophenyl) -2- (N ', N'-di
Phenyl-3 "'-aminophenyl) -3,4,5,6
-Tetraphenylbenzene 141.1,2-bis (N-phenyl-N-1 "-naphth
Cyl-2'-aminophenyl) -2- (N ', N'-di
Phenyl-2 "'-aminophenyl) -3,4,5,6
-Tetraphenylbenzene 142.1- (N-3 "-methylphenyl-N-1"'
-Naphthyl-4'-aminophenyl) -2- (N ',
N'-diphenyl-3 ""-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 143.1- (N-2 ", 5" -dimethylphenyl-N
-2 "'-naphthyl-4'-aminophenyl) -2-
(N ', N'-diphenyl-4 ""-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 144.1- (N-3 "-cyclobutyloxyphenyl
-N-1 "'-naphthyl-4'-aminophenyl) -2
-(N ', N'-diphenyl-4 ""-aminophen
) -3,4,5,6-Tetraphenylbenzene 145.1- (N-2 "-fluorophenyl-N-
1 "'-naphthyl-4'-aminophenyl) -2-
(N ', N'-diphenyl-4 ""-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 146.1- (N-methyl-N-1 "-naphthyl-4 '
-Aminophenyl) -2- (N'-ethyl-N'-phen
Nyl-4 "'-aminophenyl) -3,4,5,6-te
Traphenylbenzene 147.1- (Nn-butyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-aminophenyl) -3,4,5,6-teto
Raphenylbenzene 148.1- (N-benzyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dimethyl
-3 "'-aminophenyl) -3,4,5,6-tetra
Phenylbenzene 149.1- (N-cyclohexyl-N-1 "-naphthyl
Ru-4'-aminophenyl) -2- (N'-cyclohexyl)
Sil-N'-1 "'-naphthyl-3""-aminopheni
) -3,4,5,6-Tetraphenylbenzene 150.1- (N-isopropyl-N-2 "-naphthyl
-4'-aminophenyl) -2- (N ', N'-dife
Nyl-4 "'-aminophenyl) -3,4,5,6-te
Traphenylbenzene 151.1- (N-phenyl-4'-aminophenyl)
-2- (N ', N'-di-1 "'-naphthyl-3" -a
Minophenyl) -3,4,5,6-tetraphenylben
Zen 152.1- (N-1 "-naphthyl-4'-aminophen
Nil) -2- (N ', N'-di-1 ""-naphthyl-
3 "'-aminophenyl) -3,4,5,6-tetraf
Phenylbenzene 153.1- (N-n-hexyl-4'-aminophenyl
) -2- (N ', N'-diphenyl-3 "-aminoph
Phenyl) -3,4,5,6-tetraphenylbenzene 154.1- (N-4 "-bromobenzyl-4'-ami
Nophenyl) -2- (N ', N'-diphenyl-4 "'
-Aminophenyl) -3,4,5,6-tetraphenyl
Benzene 155.1- (4'-aminophenyl) -2- (3 "-
Aminophenyl) -3,4,5,6-tetraphenyl ester
Nzen 156.1- (3'-aminophenyl) -2- (N ',
N'-diphenyl-3 "-aminophenyl) -3,4
5,6-Tetraphenylbenzene 157.1- (2'-aminophenyl) -2- (N ',
N'-dicyclohexyl-3 "-aminophenyl)-
3,4,5,6-Tetraphenylbenzene 158.1- (N-phenyl-N-2 "-naphthyl-
4'-amino-1'-naphthyl) -2- (N ', N'-
Diphenyl-4 "'-aminophenyl) -3,4,5,
6-Tetraphenylbenzene 159.1- (N, N-diphenyl-4'-amino-
1'-naphthyl) -2- (N ', N'-diphenyl-
3 "-aminophenyl) -3,4,5,6-tetraphe
Nylbenzene 160.1- (N, N-diphenyl-4'-amino-
1'-naphthyl) -2- (N ', N'-diphenyl-
3 "-amino-1" -naphthyl) -3,4,5,6-te
Traphenylbenzene 161.1- (N, N-di-2 "-naphthyl-4'-a
Mino-2'-naphthyl) -2- (N ', N'-di-
2 ""-naphthyl-3 "'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 162.1- (N, N-di-1 "-naphthyl-4'-a
Mino-1'-naphthyl) -2- (N ', N'-dipheni
Ru-3 "'-aminophenyl) -3,4,5,6-teto
Laphenylbenzene 163.1,2-bis (N-phenyl-N-1 "-naphth
Tyl-3′-amino-2′-naphthyl) -2- (N ′,
N'-diphenyl-4 "'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 164.1- (N-phenyl-N-4 "-phenylphene
Nyl-4′-amino-1′-naphthyl) -2- (N ′,
N'-diphenyl-4 "'-amino-1"'-phenyl
) -3,4,5,6-Tetraphenylbenzene 165.1- (N-phenyl-N-3 "-phenylphen
Nyl-3′-amino-2′-naphthyl) -2- (N ′,
N'-diphenyl-4 "'-amino-1"'-naphthyl
) -3,4,5,6-Tetraphenylbenzene 166.1- (N-phenyl-N-2 "-phenylphen
Nyl-2'-amino-1'-naphthyl) -2- (N ',
N'-diphenyl-4 "'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 167.1- (N-phenyl-N-4 "-cyclohexyl
Ruphenyl-3'-amino-2'-naphthyl) -2-
(N ', N'-di-4 ""-cyclohexylphenyl-
4 "'-aminophenyl) -3,4,5,6-tetraf
Phenylbenzene 168.1- (N-phenyl-N-3 "-cyclohexyl
Ruphenyl-4'-amino-1'-naphthyl) -2-
(N ', N'-diphenyl-3 "'-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 169.1- (N-phenyl-N-2 "-anthraceni
Ru-3′-amino-1′-naphthyl) -2- (N ′,
N'-diphenyl-4 ""-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 170.1- (N-phenyl-N-9 "-anthraceni
Ru-3′-amino-2′-naphthyl) -2- (N′-fu)
Phenyl-N'-9 ""-diphenyl-4 "'-amino-
1 "'-naphthyl) -3,4,5,6-tetraphenyl
Benzene 171.1- (N-phenyl-N-9 "-phenanthre
Nyl-4′-amino-1′-naphthyl) -2- (N ′,
N'-diphenyl-4 "'-amino-2"'-phenyl
Phenyl) -3,4,5,6-tetraphenylbenzene 172.1- (N-2 "-naphthyl-N-4"'-phen
Nylphenyl-4'-amino-1'-naphthyl) -2-
(N ', N'-diphenyl-3 ""-aminophenyl)
-3,4,5,6-tetraphenylbenzene 173.1- (N-2 "-naphthyl-N-4"'-shik
Rohexylphenyl-4'-amino-1'-naphthyl)
-2- (N ', N'-diphenyl-4 ""-aminophen
Nyl) -3,4,5,6-tetraphenylbenzene 174.1- (N-2 "-naphthyl-N-1"'-naphth
Tyl-4'-amino-1'-naphthyl) -2-
(N ', N'-diphenyl-4 ""-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 175.1- (N-1 "-naphthyl-N-4"'-phen
Nylphenyl-4'-amino-1'-naphthyl) -2
-(N ', N'-diphenyl-4 ""-aminophen
) -3,4,5,6-Tetraphenylbenzene 176.1- (N-1 "-naphthyl-N-4"'-shik
Rohexylphenyl-4'-amino-1'-naphthyl)
-2- (N ', N'-diphenyl-4 ""-aminophen
Nyl) -3,4,5,6-tetraphenylbenzene 177.1- (N-1 "-naphthyl-N-2"'-phen
Nylphenyl-4'-amino-1'-naphthyl) -2
-(N ', N'-di-1 ""'-naphthyl-4 ""-a
Minophenyl) -3,4,5,6-tetraphenylben
Zen 178.1- (N-1 "-naphthyl-N-9"'-un
Toracenyl-4'-amino-1'-naphthyl) -2-
(N ', N'-diphenyl-4 ""-aminophenyl)
-3,4,5,6-tetraphenylbenzene 179.1- (N-1 "-naphthyl-N-9"'-phen
Nanthrenyl-4'-amino-1'-naphthyl) -2
-(N ', N'-diphenyl-4 ""-aminophen
) -3,4,5,6-Tetraphenylbenzene 180.1- (N-phenyl-N-2 "-naphthyl-
9'-amino-10'-anthracenyl) -2-
(N ', N'-diphenyl-4 "'-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 181.1- (N-phenyl-N-2 "-naphthyl-
4'-amino-1'-naphthyl) -2- (N'-phenyl)
Ru-N'-2 ""-naphthyl-9 "'-amino-1
0 "'-anthracenyl) -3,4,5,6-tetraf
Phenylbenzene 182.1- (N-phenyl-N-1 "-naphthyl-
9'-amino-10'-anthracenyl) -2-
(N ', N'-diphenyl-3 "'-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 183.1- (N-3 "-methylphenyl-N-1"'
-Naphthyl-4'-amino-1'-naphthyl) -2-
(N ', N'-diphenyl-4 ""-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 184.1- (N-2 ", 5" -dimethylphenyl-N
-2 "'-naphthyl-4'-amino-1'-naphthyl)
-2- (N ', N'-diphenyl-4 ""-aminophen
Nyl) -3,4,5,6-tetraphenylbenzene 185.1- (N-methyl-N-1 "-naphthyl-
4'-amino-1'-naphthyl) -2- (N ', N'-
Diphenyl-4 "'-aminophenyl) -3,4,5,
6-Tetraphenylbenzene 186.1- (N-n-butyl-N-1 "-naphthyl-
4'-amino-1'-naphthyl) -2- (N ', N'
-Di-n-butyl-3 "'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 187.1- (N-benzyl-N-1 "-naphthyl-
4'-amino-1'-naphthyl) -2- (N ', N'-
Diphenyl-4 ""-aminophenyl) -3,4,5,
6-Tetraphenylbenzene 188.1- (N-cyclohexyl-N-1 "-naphthyl
Ru-4'-amino-1'-naphthyl) -2- (N ',
N'-dicyclohexyl-3 ""-aminophenyl)-
3,4,5,6-Tetraphenylbenzene 189.1- (N-isopropyl-N-2 "-naphthyl
-4'-amino-1'-naphthyl) -2- (N ', N'
-Diphenyl-4 "'-aminophenyl) -3,4
5,6-Tetraphenylbenzene 190.1- (N-phenyl-4'-amino-1'-na
Futyl) -2- (N ', N'-diphenyl-4 "-ami
Nophenyl) -3,4,5,6-tetraphenylbenze
191.1- (N-1 "-naphthyl-9'-amino-1
0'-anthracenyl) -2- (N ', N'-dipheny
Ru-4 "-amino-1" -naphthyl) -3,4,5,6
-Tetraphenylbenzene 192.1- (Nn-hexyl-4'-amino-1 '
-Naphthyl) -2- (N ', N'-diphenyl-4 "-
Aminophenyl) -3,4,5,6-tetraphenyl ester
Nzen 193.1- (N-4 "-fluorobenzyl-4'-a
Mino-1'-naphthyl) -2- (N ', N'-dipheni
Ru-9 "-amino-10" -anthracenyl) -3,
4,5,6-Tetraphenylbenzene 194.1- (4'-amino-1'-naphthyl) -2-
(N ', N'-diphenyl-9 "-amino-10" -a
(Ntracenyl) -3,4,5,6-tetraphenylben
Zen 195.1- (9'-amino-10'-anthraceni
) -2- (N ', N'-diphenyl-4 "-aminoph
Phenyl) -3,4,5,6-tetraphenylbenzene 196.1- (N-phenyl-N-2 "-naphthyl-
4'-amino-2 ', 5'-dimethylphenyl) -2-
(N ', N'-diphenyl-4 "'-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 197.1- (N-phenyl-N-2 "-naphthyl-
3'-amino-5'-phenylphenyl) -2-
(N ', N'-diphenyl-4 "'-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 198.1- (N-phenyl-N-1 "-naphthyl-
4'-amino-2'-phenylphenyl) -2-
(N ', N'-diphenyl-3 "'-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 199.1- (N-phenyl-N-1 "-naphthyl-
4'-amino-2'-tert-butylphenyl) -2-
(N ', N'-diphenyl-3 "'-aminophenyl)
-3,4,5,6-Tetraphenylbenzene 200.1- (N-phenyl-N-4 "-phenylphen
Nyl-2'-amino-4'-sec-butylphenyl)-
2- (N ', N'-di-1 ""-naphthyl-3 "'-a
Minophenyl) -3,4,5,6-tetraphenylben
Zen 201.1- (N-phenyl-N-9 "-phenanthre
Nyl-4'-amino-5'-benzyloxyphenyl)
-2- (N ', N'-diphenyl-4 "'-amino-
2 "-methylphenyl) -3,4,5,6-tetraphe
Nylbenzene 202.1- (N, N-di-1 "-naphthyl-4'-a
Mino-2'-methyl-1'-naphthyl) -2- (N ',
N'-diphenyl-4 "'-aminophenyl) -3,
4,5,6-Tetraphenylbenzene 203.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-aminophenyl) -4,5-diphenyl ester
Nzen 204.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3,6-diphenylbe
Nzen 205.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-aminophenyl) benzene 206.1- (N-phenyl-N-1" -naphthyl-
4'-aminophenyl) -2- (3 "'-aminopheni
) -4,5-Dimethylbenzene 207.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3-fluoro-4,
5,6-Triphenylbenzene 208.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3,6-dicyanoben
Zen 209.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-amino-1"'-naphthyl) -3,6-di
-tert-butylbenzene 210.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3,6-dicyclohexyl
Sil-4,5-diphenylbenzene 211.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3,5-di-n-noni
Rubenzene 212.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-aminophenyl) -3,6-diphenyl-
4,5-Dimethylbenzene 213.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-aminophenyl) -3,6-di (4""-
Phenylphenyl) -4,5-diphenylbenzene 214.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3,6-di (4""-
Methylphenyl) -4,5-diphenylbenzene 215.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-aminophenyl) -3,6-di (4""-
Fluorophenyl) -4,5-diphenylbenzene 216.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3,6-di (3""-
Ethoxyphenyl) -4,5-diphenylbenzene 217.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-3 "'-aminophenyl) -3,6-diphenyl-
4,5-di (4 ""-benzyloxyphenyl) benze
218.1- (N-phenyl-N-1 "-naphthyl-
4'-aminophenyl) -2- (N ', N'-dipheny
Ru-4 "'-amino-1"'-naphthyl) -3,6-di
(3 ""-phenylphenyl) -4,5-diphenyl ester
Nzen

The amine compound represented by the general formula (1) of the present invention can be produced, for example, by the following steps.

Production of amine compound represented by the general formula (1)

[0094]

[Chemical 11]

That is, it can be produced by reacting the diphenylacetylene derivative represented by the general formula (3) with the cyclopentadienone derivative represented by the general formula (4). The reaction is carried out in a solvent (for example, an aromatic solvent such as toluene, benzene, xylene, naphthalene, tetralin, chlorobenzene, dichlorobenzene, nitrobenzene, N, N-dimethylimidazolidinone, N-methylpyrrolidone, diethylene glycol dimethyl ether, diethylene glycol). It may be carried out in a polar solvent such as monomethyl ether or diethylene glycol), or may be carried out without solvent. The reaction temperature can be any temperature from room temperature to the decomposition temperature of the product, but is preferably 100 ° C. or higher and the decomposition temperature of the product or lower, more preferably 150 ° C. or higher. Three
It is not higher than 00 ° C.

In the amine compound represented by the general formula (1), at least one of A _{11 to} A ₁₅ and A _{21 to} A ₂₅ is a group represented by the general formula (2). ) May be produced from the diphenylacetylene derivative represented by the formula (1), and a group (for example, a halogen atom, a nitro group or a hydroxy group) which can be converted into an amino group represented by the formula (2) is represented by A ₁₁ to.
A precursor represented by the general formula (1 ′) is produced from a diphenylacetylene derivative represented by the general formula (3 ′) having at least one in A ₁₅ and A _{21 to} A ₂₅ , and then produced by a known method. A method for producing a compound represented by the general formula (1) by converting a group convertible to the amino group represented by the formula (2) into an amino group represented by the formula (2) (Chemical Formula 12) May be manufactured by.

[0097]

[Chemical 12]

[Wherein A ′ _{11 to} A ′ ₁₅ and A ′ ₂₁ to
A ′ ₂₅ has the same meaning as A _{11 to} A ₁₅ and A _{21 to} A ₂₅ , and at least one of A ′ _{11 to} A ′ ₁₅ and A ′ ₂₁ to
At least one of A ′ ₂₅ represents a group convertible to an amino group represented by the formula (2), and X ₁ , X ₂ , X ₃ and X ₄ , A ₁₁
To A ₁₅ and A _{21 to} A ₂₅ have the above-mentioned meanings] That is, in the general formula (1 ′), at least one of A ′ _{11 to} A ′ ₁₅ and at least one of A ′ _{21 to} A ′ ₂₅ are When it is a halogen atom, a compound represented by the general formula (1 ′) is reacted with an amine derivative represented by the general formula (5) (wherein Y ₁ and Y ₂ represent the above meanings). By doing so, the compound represented by the general formula (1) can be produced (Chemical Formula 13).

[0099]

[Chemical 13]

The reaction between the compound represented by the general formula (5) and the compound represented by the general formula (1 ′) is carried out, for example, by a base (eg potassium carbonate, sodium carbonate, potassium tert-butoxide). And a copper catalyst (for example, copper powder,
Method (Ullmann reaction) carried out in a polar solvent (eg sulfolane, N, N-dimethylformaldehyde, dichlorobenzene, nitrobenzene) in the presence of copper / bronze powder, copper chloride, copper bromide, copper iodide), palladium catalyst [For example, palladium acetate / tri-t-butylphosphine, palladium acetate / triphenylphosphine, tris (dibenzylideneacetone) dipalladium / tri-tert-butylphosphine, tris (dibenzylideneacetone) dipalladium / di-tert-butyl- o-biphenylphosphine,
Tris (dibenzylideneacetone) dipalladium / dicyclohexyl-o-biphenylphosphine, tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium] and bases (eg potassium carbonate, sodium carbonate, cerium carbonate, potassium-tert- Butoxide, sodium-tert-butoxide) and the like in a solvent (for example, toluene, xylene, 1,4-dioxane, tetrahydrofuran) in the presence of an inert gas stream, and the like.

In the general formula (1 '), A'₁₁~
A ’₁₅At least one of A, and A ' _{twenty one}~ A '_{twenty five}Little
When at least one is a nitro group, it can be prepared by a known method.
Reduction of nitro group (for example, isopropanol etc.
Reduction with reduced iron in coal solvent, under hydrogen atmosphere,
Reduction with a palladium catalyst such as radium / carbon)
After forming a mino group, a general formula (6) or a general formula (6 ')
Represented halogenated compound (wherein Y₁And Y₂Is the above
And X'represents a halogen atom).
A compound represented by the general formula (1) according to the method (Chemical formula 14)
Can be manufactured.

[0102]

[Chemical 14]

Further, in the general formula (1 ′), A ′ ₁₁
If to A _'15 and A' ₂₁ ~A _'25 at least one by one of such hydroxy, trifluoromethanesulfonic acid ester, after conversion to p- toluenesulfonic acid ester, tables in the general formula (5) The amine compound represented by the general formula (1) can be produced by reacting with the amine compound.

Next, the organic electroluminescent device of the present invention will be described. The organic electroluminescent element of the present invention, between a pair of electrodes,
At least one layer containing at least one kind of the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) is sandwiched. An organic electroluminescent device is usually one in which at least one light emitting layer containing at least one light emitting component is sandwiched between a pair of electrodes. Considering the respective functional levels of hole injection and hole transport, electron injection and electron transport of the compound used for the light emitting layer, and if desired, a hole injection transport layer and / or electron injection containing a hole injection component. An electron injecting and transporting layer containing a transporting component can also be provided.

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

Further, 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 are In each layer, a layer having an injection function and a layer having a transport function may be separately provided.

In the organic electroluminescent device of the present invention, the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) is used in the hole injecting and transporting layer and / or the light emitting layer. It is preferably used as a constituent component, and more preferably used as a constituent component of the hole injecting and transporting layer. In the organic electroluminescent device of the present invention, the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) may be used alone or in combination. Good.

The constitution of the organic electroluminescent element of the present invention is not particularly limited, but for example, (A) anode / hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element (see FIG. 1), (B) anode / hole injecting / transporting layer / light emitting layer /
Examples include a cathode type device (FIG. 2), (C) anode / light emitting layer / electron injecting / transporting layer / cathode type device (FIG. 3), (D) anode / light emitting layer / cathode type device (FIG. 4), and the like. it can. Further, (E) anode / hole injecting / transporting layer / electron injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element (FIG. 5) in which the light emitting layer is sandwiched between electron injecting and transporting layers may be used. it can. The (D) type element structure is a type element in which a light emitting component is sandwiched between a pair of electrodes in a single layer as a light emitting layer,
(F) A device of a type in which a hole injection / transport component, a light emitting component and an electron injection component are mixed as a light emitting layer and sandwiched between a pair of electrodes (FIG. 6), and (G) a hole injection is performed as a light emitting layer. An element of a type in which a transport component and a light emitting component are mixed and sandwiched between a pair of electrodes (FIG. 7), and (H) a pair of electrodes in a single layer in which a light emitting component and an electron injection component are mixed as a light emitting layer. It may be any of the types of elements sandwiched between them (FIG. 8).

The organic electroluminescent device of the present invention is not limited to these device configurations, and a plurality of hole injecting and transporting layers, light emitting layers, and electron injecting and transporting layers may be provided in each type of device. Is. Further, in each type of device, the hole injecting and transporting layer is provided between the light emitting layer, the mixed layer of the hole injecting and transporting component and the light emitting component and / or the light emitting component is provided between the light emitting layer and the electron injecting and transporting layer. It is also possible to provide a mixed layer of the electron injecting and transporting component.

The preferable structure of the organic electroluminescent device is as follows.
(A) type element, (B) type element, (E) type element, (F) type element or (G) type element, and more preferably,
It is an (A) type element, a (B) type element or a (G) type element.

The constituent elements of the organic electroluminescent element of the present invention will be described in detail below. As an example, (A) anode / hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode type element 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 on the substrate 1. The substrate is not particularly limited, but a transparent or semitransparent substrate is preferable, and the material is soda. Examples thereof include glass such as lime glass and borosilicate glass, and transparent polymers such as polyester, polycarbonate, polysulfone, polyether sulfone, polyacrylate, polymethylmethacrylate, polypropylene and polyethylene.
It is also possible to use a substrate made of a semitransparent plastic sheet, quartz, transparent ceramics, or a composite sheet in which these are combined. Further, the substrate can be combined with, for example, a color filter film, a color conversion film, or a dielectric reflection film 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. As the electrode material used for the anode, for example, gold,
Platinum, silver, copper, cobalt, nickel, palladium, vanadium, tungsten, indium oxide (In2O
3), tin oxide (SnO2), zinc oxide, ITO (Indium Tin Ox)
ide), polythiophene, polypyrrole and the like. These electrode materials may be used alone or in combination.

The anode can be formed on the substrate by using these electrode materials by a method such as a vapor deposition method or a sputtering method.

The anode may have a monolayer structure or a multilayer structure. The sheet electrical resistance of the anode is preferably several hundred Ω / □ or less, more preferably 5 or less.
Set to about 50Ω / □.

Although the thickness of the anode depends on the material of the electrode material used, it is generally set to about 5 to 1000 nm, more preferably about 10 to 500 nm.

The hole injecting and transporting 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 comprises the compound represented by the general formula (1), the compound represented by the general formula (2) and / or another compound having a hole injecting and transporting function (for example, a phthalocyanine derivative, Triarylamine derivative, triarylmethane derivative, oxazole derivative, hydrazone derivative, stilbene derivative, pyrazoline derivative, polysilane derivative, polyphenylene vinylene and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole, etc.) Can be formed. The compound having a hole injection / transport function is
They may be used alone or in combination.

The organic electroluminescent device of the present invention preferably contains the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) in the hole injecting and transporting layer. It has a hole injecting and transporting function other than the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) of the present invention, which can be used in the organic electroluminescence device of the present invention. Examples of the compound 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,
1,1-bis [4 '-[N, N-di (4 "-methylphenyl) amino] phenyl] cyclohexane, 9,10-
Bis [N- (4'-methylphenyl) -N- (4 "-n
-Butylphenyl) amino] phenanthrene, 3,8-
Bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-N, N-bis [4 ″,
4 "'-bis [N', N'-di (4-methylphenyl)
Amino] biphenyl-4-yl] aniline, N, N'-
Bis [4- (diphenylamino) phenyl] -N, N '
-Diphenyl-1,3-diaminobenzene, N, N'-
Bis [4- (diphenylamino) phenyl] -N, N '
-Diphenyl-1,4-diaminobenzene, 5,5 "-
Bis [4- (bis [4-methylphenyl] amino] phenyl-2,2 ′: 5 ′, 2 ″ -terthiophene, 1,
3,5-tris (diphenylamino) benzene, 4,
4 ', 4 "-tris (N-carbazolyyl) triphenylamine, 4,4', 4" -tris [N, N-bis (4 "'-tert-butylbiphenyl-4""-yl) amino] tri Phenylamine, 1,3,5-tris [N-
More preferred are polythiophene and its derivatives, such as (4′-diphenylamino] benzene, and poly-N-vinylcarbazole and its derivatives.

When the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) is used in combination with another compound having a hole injecting function, the compound is added in the hole injecting and transporting layer. The content of the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) is preferably 0.1% by weight or more, and more preferably 0.5 to 99. 1.9% by weight, more preferably 3 to
It is 97% by weight. The light emitting layer 4 is a layer containing a compound having a function of injecting holes and electrons, a function of transporting them, and a function of generating excitons by recombination of holes and electrons.

The light emitting layer uses the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) as a host material, and the amine compound represented by the general formula (1) and the general compound A compound having a light emitting function other than the amine compound represented by the formula (2) can be used as at least one guest material to be formed.

Examples of the compound (guest material) having a light emitting function other than the amine compound represented by the general formula (1) and the amine compound represented by the general formula (2) include, for example, acridone derivatives, quinacridone derivatives and diketo. Pyrrolopyrrole derivatives, polycyclic aromatic compounds (for example, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene,
9,10-Diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthocenyl) benzene, 4,4'-
Bis (9 "-ethynylanthracenyl) biphenyl, dibenzo [f, f] diindeno [1,2,3-cd: 1 ', 2', 3'-lm] perylene derivative], triarylamine derivative (for example,
Examples of the compound having a hole injecting / transporting function include the compounds described above), organometallic complexes [eg, tris (8-quinolinolato) aluminum, bis (10-
Benzo [h] quinolinolato) beryllium, 2- (2 '
Zinc salt of -hydroxyphenyl) benzothiazole, 4
-Zinc salt of 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 derivative (for example, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 13)
8, coumarin 151, coumarin 152, coumarin 15
3, coumarin 307, coumarin 311, coumarin 31
4, coumarin 334, coumarin 338, coumarin 34
3, coumarin 500), pyran derivative (eg DCM
1, DCM2), oxazone derivative (for example, Nile red), benzothiazole derivative, benzoxazole derivative, benzimidazole derivative, pyrazine derivative,
Cinnamic acid ester derivative, poly-N-vinylcarbazole and its derivative, polythiophene and its derivative, polyphenylene and its derivative, polyfluorene and its derivative, polyphenylenevinylene and its derivative, polybiphenylenevinylene and its derivative,
Examples thereof include polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and its derivatives, polythienylene vinylene and its derivatives, and the like. Examples of the compound (guest material) having a light emitting function other than the amine compound represented by the general formula (1) and the amine compound represented by the general formula (2) include acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, and triatomic compounds. A reel amine derivative, an organometallic complex and a stilbene derivative are preferable, and a polycyclic aromatic compound and an organometallic complex are more preferable.

The organic electroluminescent element of the present invention preferably contains the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) as a host material in the light emitting layer.

When the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) is used as a host material in combination with another compound having a light emitting function, it occupies in the light emitting layer. The content of the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2) is preferably 40.0% to 99.9%.
And more preferably 60.0 to 99.9% by weight.

The amount of the guest material used is 0.001 to 40% by weight, preferably 0, based on the amine compound represented by the general formula (1) and / or the amine compound represented by the general formula (2). 0.05 to 30% by weight, more preferably
It is 0.1 to 20% by weight. The guest materials may be used alone or in combination of two or more. The electron injection / transport layer 5 is a layer containing a compound having a function of facilitating the injection of electrons from the cathode and / or a function of transporting the injected electrons.

Examples of the compound having an electron injecting function used in the electron injecting and transporting layer include organic metal complexes, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, Examples thereof include nitro-substituted fluorenone derivatives and thiopyrandioxide derivatives. As the organometallic complex, for example, 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 aluminum salt of hydroxyflavone. It is preferably an organoaluminum complex, and more preferably
It is an organoaluminum complex having a substituted or unsubstituted 8-quinolinolato ligand. 8-substituted or unsubstituted
Examples of the organoaluminum complex having a quinolylate ligand include compounds represented by the general formulas (a) to (c).

(Q) ₃ -Al (a) (wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand) (Q) ₂ -Al-OL '(b) (wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand, OL ′ represents a phenolate ligand,
L ′ represents a hydrocarbon group having a phenyl group and having 6 to 24 carbon atoms. (Q) ₂ —Al—O—Al— (Q) ₂ (c) (In the formula, Q is a substituted or unsubstituted 8- Represents a quinolinolato ligand)

Specific examples of the organoaluminum complex having a substituted or unsubstituted 8-quinolinolate ligand include:
For example, tris (8-quinolinolato) aluminum,
Tris (4-methyl-8-quinolinolato) aluminum, tris (5-methyl-8-quinolinolato) aluminum, tris (3,4-dimethyl-8-quinolinolato) aluminum, tris (4,5-dimethyl-8-quinolinolato) Aluminum, tris (4,6-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-8-quinolinolato) (phenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-
Methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(4-Methylphenolate) aluminum, bis (2-
Methyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenolato) aluminum,
Bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,3-dimethylphenolate)
Aluminum, bis (2-methyl-8-quinolinolato) (2,6-dimethylphenolate) aluminum,
Bis (2-methyl-8-quinolinolato) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8-) Quinolinolato) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolato)
(2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-
Triphenylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8)
-Quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate ) Aluminum, bis (2,4-dimethyl-8-quinolinolato) (2-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolato)
(3-Phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate ) Aluminum, bis (2,4-dimethyl-8-
Quinolinolato) (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, bis (2- Methyl-5-trifluoromethyl-8-quinolinolate)
Aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum can be mentioned.

The compound having an electron injection function may be used alone or in combination of two or more.

For the cathode 6, it is preferable to use a metal, alloy or conductive compound having a relatively small work function as an electrode material. As the electrode material used for the cathode,
For example, lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium, manganese, yttrium, aluminum, aluminum-lithium alloy, aluminum-calcium. Alloys, aluminum-magnesium alloys, and graphite thin can be mentioned. 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, the vapor deposition method, the sputtering method, the ion vapor deposition method, the ion plating method or the cluster ion beam method.

The cathode may have a single-layer structure or a multi-layer structure. Sheet electric resistance of the cathode is several hundred Ω
/ □ or less is preferable. The thickness of the cathode depends on the electrode material used, but is usually 5 to 1000 nm, preferably 10 to 500 nm. In order to extract 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 semitransparent, and generally the transmittance of emitted light is 70% or more. Thus, it is preferable to set the material and thickness of the anode or cathode.

In the organic electroluminescent device of the present invention, at least one of the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer may contain a singlet oxygen quencher. The singlet oxygen quencher is not particularly limited, but examples thereof include rubrene, nickel complex, and diphenylisobenzofuran, and rubrene is preferable.

The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injecting and transporting layer, more preferably a hole injecting and transporting layer. is there. When the hole injecting and transporting layer contains a singlet oxygen quencher, 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 included in the vicinity of the electron injecting and transporting layer).

The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.0 to 50% by weight based on the total amount of the layer (eg, the hole injecting and transporting layer).
5 to 30% by weight, more preferably 0.1 to 20% by weight
Is.

Hole injection / transport layer, light emitting layer, electron injection / transport layer
The method of forming is not particularly limited,
For example, vacuum deposition method, ionization deposition method, solution coating method (example
For example, spin coating, casting, dip coating
Method, bar coat method, roll coat method, Langmuir Bou
Can be used.
Wear. Hole injecting and transporting layer, emitting layer, electron by vacuum evaporation method
When forming each layer such as injecting and transporting layer, vacuum deposition conditions
Ha. , But is not particularly limited, usually 10 ^-FiveT
Under a vacuum of about orr or less, a bow of about 50 to 500 ° C
Temperature (deposition source temperature), substrate temperature of about -50 to 300 ° C
Deposition rate of 0.005 to 50 nm / sec.
It is preferable to apply. In this case, the hole injection transport layer
Each layer such as the light layer and the electron injecting and transporting layer is continuously placed under vacuum.
It is preferably formed. By continuously forming
It is possible to manufacture organic electroluminescent devices with excellent characteristics.
Become. By vacuum evaporation method, hole injection transport layer, light emitting layer,
Each layer such as child injection transport layer is formed using multiple compounds
Temperature control for each boat containing compound
Therefore, co-evaporation is preferable.

When each layer is formed by the solution coating method, the component forming each layer or the component and the binder resin are dissolved or dispersed in a solvent to prepare a coating liquid. As the solvent, for example, an organic solvent (hexane, octane, decane, toluene, xylene, ethylbenzene, a hydrocarbon solvent such as 1-methylnaphthalene, a ketone solvent such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dichloromethane, chloroform) ,
Tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene, halogenated hydrocarbon solvents such as chlorotoluene, ethyl acetate, butyl acetate, amyl acetate, ester solvents such as ethyl lactate, methanol, propanol, butanol, Alcohol solvents such as pentanol, hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, ethylene glycol, dibutyl ether,
Tetrahydrofuran, dioxane, dimethoxyethane,
Ether solvent such as anisole, polar solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide), water Can be mentioned. The solvent may be used alone or in combination of two or more. 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 to form a fine particle. Can be used.

Further, as the binder resin which can be used for each layer such as the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer,
Poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethylmethacrylate, polymethylacrylate, polyether, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene, polyphenylene oxide, polyether sulfone , Polyaniline and its derivatives, polythiophene and its derivatives, polyphenylene vinylene and its derivatives, polyfluorene and its derivatives, polythienylene vinylene and its derivatives, and the like. The binder resins may be used alone or in combination of two or more. The concentration of the coating liquid is not particularly limited, but can be set within a concentration range suitable for producing a desired thickness by the coating method to be performed, and is usually 0.1 to 50% by weight, preferably , 1 to 30% by weight
Set to. When a binder resin is used, the amount thereof is not particularly limited, but is usually relative to the total amount of the component and the binder resin forming each layer such as the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer. The binder resin content (based on the total amount of each component in the case of forming a one-layer type element) is 5 to 99.9% by weight, preferably 10 to 9
It is used so as to be 9% by weight.

The film pressure of each layer such as the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting 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) or is inactive for the purpose of preventing contact with oxygen, moisture and the like. It can be protected by enclosing it in a substance (for example, paraffin, liquid paraffin, silicone oil, fluorocarbon oil, zeolite-containing fluorocarbon oil). Examples of the material used for the protective layer include organic polymer materials (for example, fluororesin, epoxy resin, silicone resin, epoxysilicone 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),
Furthermore, a photocurable resin can be mentioned. The materials 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.

Further, in the organic electroluminescent element of the present invention, a metal oxide film (eg, aluminum oxide film) or a metal fluoride film can be provided on the electrode as a protective film.

In the organic electroluminescent element of the present invention, an interface layer (intermediate layer) may be provided on the surface of the anode. Examples of the material of the interface layer include organic phosphorus compounds, polysilanes, aromatic amine derivatives, and phthalocyanine derivatives.

Furthermore, an electrode, for example, an anode, can be used by treating the surface with an acid, ammonia / hydrogen peroxide or plasma.

The organic electroluminescent device of the present invention can be usually used as a DC drive type device, but can also be used as an AC drive type device. Further, the organic electroluminescent element of the present invention may be of a passive drive type such as a segment type or a simple matrix drive type, or an active drive type such as a TFT (thin film transistor) type or a MIM (metal-insulator-metal) type. May be The drive voltage is usually 2 to 30V. The organic electroluminescent device of the present invention includes a panel type light source (for example, a backlight such as a watch and a liquid crystal panel), various light emitting devices (for example, a light emitting device such as an LED), and various display devices [for example, information display. It can be used for devices (PC monitors, display devices for mobile phones and mobile terminals), various signs, various sensors, etc.

[0145]

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples.

(Example 1) Production of Exemplified Compound 1: Production of 1,2-bis (4'-bromophenyl) acetylene A) 4-Bromoiodobenzene 283 g, 3-methyl-
126 g of 1-butyn-3-ol, 5.5 g of dichlorobis (triphenylphosphine) palladium, copper iodide 2
g, 4 g of triphenylphosphine and 500 g of triethylamine were added to 70 ° C. under a nitrogen atmosphere at 1 ° C.
The mixture was heated and stirred at 80 ° C. for 6 hours. Then, toluene was added to the mixture, the mixture was cooled to room temperature, the insoluble matter was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the desired product, 1-
(4'-Bromophenyl) -3-methyl-1-butyne-
201 g of 3-ol was obtained. Next, 1- (4'-bromophenyl) -3-methyl-1-butyn-3-ol 2
01 g, 900 g of toluene and 20 g of powdered potassium hydroxide were heated and stirred at 110 ° C. for 2 hours while removing acetone. Then the reaction mixture was cooled to room temperature and the reaction was filtered over Celite. The filtrate was washed with water, and toluene was distilled off under reduced pressure to obtain 160 g of the target 1- (4'-bromophenyl) acetylene. B) 90 g of 1- (4'-bromophenyl) acetylene,
141 g of 4-bromoiodobenzene, 2 g of dichlorobis (triphenylphosphine) palladium, copper iodide 0.
A mixture of 5 g, 2 g of triphenylphosphine and 300 g of triethylamine was heated and stirred at 80 ° C. for 5 hours under a nitrogen atmosphere. Then, toluene was added to the mixture, the mixture was cooled to room temperature, and the insoluble material was filtered off. The filtrate was evaporated under reduced pressure and purified by silica gel column chromatography to obtain the target 1,2-bis (4'-bromophenyl) acetylene (134 g). 1,2-bis (N-phenyl-N-2 "-naphthyl-
Production of 4'-aminophenyl) acetylene. 16.5 g of N-phenyl-N-2-naphthylamine,
1,2-bis (4'-bromophenyl) acetylene 12
g, sodium-tert-butoxide 9.6 g, palladium acetate 0.18 g, tri-tert-butylphosphine 0.6
A mixture of 5 g and 96 g of toluene was heated and stirred under a nitrogen atmosphere at 100 ° C. for 5 hours, and then discharged into methanol to give 1,2-bis (N-phenyl-N) as crude crystals.
22 g of -2 "-naphthyl-4'-aminophenyl) acetylene was obtained. 3,4,5,6-totetraphenyl-1,2-bis (N-phenyl-N-2" -naphthyl-4-amino Preparation of phenyl) benzene 1,2-bis (N-phenyl-N-2 "-naphthyl-4
-Aminophenyl) benzene (7.7 g) and tetraphenylcyclopentadienone (5.1 g) at 265 to 275 ° C.
Then, the mixture was heated and melted at, and then heated at the same temperature for 30 minutes, and it was confirmed that the generation of gas was completed. Then, the reaction mixture was cooled and recrystallized from toluene to obtain the desired 1,2-bis (N-phenyl-N-2 "-naphthyl-4-aminophenyl) -3,4,5,6-tetraphenyl. 10.6 g of benzene (Exemplary Compound 1) was obtained, and this compound was further purified by sublimation at 350 ° C. and 1 × 10 ⁻⁴ Pa.

Example 2 Production of Exemplified Compound 2 In Example 1, except that 16.5 g of N-phenyl-N-2-naphthylamine was used, 12.7 g of N, N-diphenylamine was used. According to the procedure described in Example 1, 9.3 g of the compound of Exemplified Compound 2 was obtained.
Further, this compound was purified by sublimation at 340 ° C. and 1 × 10 ⁻⁴ Pa.

Example 3 Production of Exemplified Compound 5 Instead of using 16.5 g of N-phenyl-N-2-naphthylamine in Example 1, 16.5 g of N-phenyl-N-1-naphthylamine was used. Compound 1 of Exemplified Compound 5 according to the procedure described in Example 1 except that it was used
1.2 g was obtained. Furthermore, this compound was heated at 350 ° C, 1 x 1
Sublimation purification was performed at 0 ⁻⁴ Pa.

Example 4 Production of Exemplified Compound 6 Instead of using 16.5 g of N-phenyl-N-2-naphthylamine in Example 1, 18-fold of N-phenyl-N-4-phenylphenylamine was used. By following the procedure described in Example 1 except that 0.4 g was used, 11.2 g of Exemplified Compound 6 was obtained. Furthermore, this compound was
Sublimation purification was performed at 1 × 10 ⁻⁴ Pa.

(Example 5) Production of Exemplified Compound 20 Instead of using 16.5 g of N-phenyl-N-2-naphthylamine in Example 1, N-1-naphthyl-N-9'-phenanthate was used. 23.9 g of renylamine
Compound 13.5 g of Exemplified Compound 20 was obtained by following the procedure described in Example 1 except that the compound was used. Furthermore, this compound 3
Sublimation purification was performed at 80 ° C. and 1 × 10 ⁻⁴ Pa.

Example 6 Preparation of Exemplified Compound 120 Described in Example 1 except that 141 g of 3-bromoiodobenzene was used instead of 141 g of 4-bromoiodobenzene in -B) of Example 1. 11.2 g of the compound of Exemplified Compound 120 was obtained in accordance with the procedure of. Further, this compound was purified by sublimation at 330 ° C. and 1 × 10 ⁻⁴ Pa.

(Example 7) Production of Exemplified Compound 123 Instead of using 141 g of 4-bromoiodobenzene in -B) of Example 1, 141 g of 3-bromoiodobenzene was used, and N-phenyl- N
-2- Instead of using 16.5 g of naphthylamine,
N-phenyl-N-9-phenanthrenylamine was added to 2
According to the procedure described in Example 1 except that 0.2 g was used, 14.1 g of Exemplified Compound 123 was obtained. Further, this compound was purified by sublimation at 370 ° C. and 1 × 10 ⁻⁴ Pa.

Example 8 Preparation of Organic Electroluminescent Device Glass with ITO transparent electrode (anode) of 200 nm thickness
Substrate, neutral detergent, semicoclean (Furuuchi Chemical
), Ultrasonic cleaning with ultrapure water, acetone, ethanol
Clean This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, fixed to the substrate holder of the vapor deposition device
Then, the evaporation tank is 3 × 10^-6The pressure was reduced to Torr. First, ITO
The compound of Exemplified Compound 1 was deposited on the transparent electrode at a deposition rate of 0.2.
Hole injection and transport by vapor deposition to a thickness of 75 nm at nm / sec
Layers were formed. Next, on the hole injecting and transporting layer, tris (8
-Quinolinolato) aluminum vapor deposition rate 0.2 nm
/ Sec to a thickness of 50 nm to form an electron injecting and transporting layer.
A light emitting layer having the combined function was formed. Furthermore, on top of that, the cathode
And silver vapor deposition rate of 0.2 nm / sec as
Co-deposition (weight ratio 10: 1) to a thickness of 200 nm
An organic electroluminescence device was prepared by using the electrode as a pole. The vapor deposition is
It was carried out while maintaining the reduced pressure in the tank. Organic electricity produced
DC voltage is applied to the field emission device, 50 ° C, dry atmosphere
Below 10 mA / cm ²It was continuously driven at a constant current density of.
Initially, 5.9V, brightness 510 cd / m²Green departure
The light was confirmed. The half-life of brightness was 640 hours.

(Examples 9 to 12) Production of organic electroluminescent device In Example 8, instead of using the compound of Exemplified Compound 1 in the formation of the hole injecting and transporting layer, Exemplified Compound 2 was used.
Example 8 except that the compound of Example 4 (Example 9), the compound of Example Compound 5 (Example 10), the compound of Example Compound 6 (Example 11), and the compound of Example Compound 20 (Example 12) were used. An organic electroluminescent device was produced according to the operation described. Green light emission was confirmed from each element. Further, its characteristics were examined, and the results are shown in Table 1 (Table 1).

Comparative Example 1 In Example 8, instead of using the compound of Exemplified Compound 1 in forming the hole injecting and transporting layer, 4,4′-bis [N-phenyl-N-
An organic electroluminescent device was produced by following the procedure described in Example 8 except that (3 ″ -methylphenyl) amino] biphenyl was used. Green luminescence was confirmed from the device. Is shown in Table 1 (Table 1).

Comparative Example 2 In Example 8, instead of using the compound of Exemplified Compound 1 in the formation of the hole injecting and transporting layer, 9,9-dimethyl-2,7-bis (N, N) was used.
An organic electroluminescent device was produced by following the procedure described in Example 8 except that -diphenylamino) fluorene was used. Green light emission was confirmed from each element. Further, its characteristics were examined, and the results are shown in Table 1 (Table 1).

[0157]

[Table 1]

Example 13 Preparation of Organic Electroluminescent Device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was treated with neutral detergent, semicoclean (manufactured by Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. Used for ultrasonic cleaning. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, ITO
Poly (thiophene-2,5-diyl) was deposited on the transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injecting and transporting layer. Then, the compound of Exemplified Compound 120 was deposited at a deposition rate of 0.2 nm / sec to 55
The second hole injecting and transporting layer was formed by vapor deposition to a thickness of nm.
Next, tris (8-quinolinolato) aluminum is deposited on the hole injecting and transporting layer at a deposition rate of 0.2 nm / sec.
It was vapor-deposited to a thickness of nm to form a light emitting layer which also serves as an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. A direct current voltage was applied to the produced organic electroluminescent device, and it was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. Initially, green light emission of 6.1 V and a luminance of 530 cd / m ² was confirmed. The half-life of brightness was 1600 hours.

Example 14 Preparation of Organic Electroluminescent Device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was treated with neutral detergent, semicoclean (Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. Used for ultrasonic cleaning. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, ITO
On the transparent electrode, 4,4 ', 4 "-tris [N- (3"-
Methylphenyl) -N-phenylamino] triphenylamine was deposited at a deposition rate of 0.1 nm / sec to a thickness of 50 nm to form a first hole injecting and transporting layer. Then
A compound of Exemplified Compound 2 and rubrene were co-evaporated from different vapor deposition sources to a thickness of 20 nm at a vapor deposition rate of 0.2 nm / sec (weight ratio 10: 1), and a light emitting layer also serving as a second hole injecting and transporting layer. Was formed. Then add Tris (8
-Quinolinolato) aluminum vapor deposition rate 0.2 nm
/ Sec to a thickness of 50 nm to form a light emitting layer which also serves as an electron injecting and transporting layer. Furthermore, magnesium and silver as a cathode are vapor-deposited thereon with a deposition rate of 0.2 nm / sec.
Was co-evaporated to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. A direct current voltage is applied to the produced organic electroluminescent device in a dry atmosphere for 10 m.
It was continuously driven at a constant current density of A / cm ² . In the early days,
Yellow light emission at 6.1 V and a brightness of 540 cd / m ² was confirmed. The half-life of brightness was 1700 hours.

Example 15 Preparation of Organic Electroluminescent Device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was treated with neutral detergent, semicoclean (manufactured by Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. Used for ultrasonic cleaning. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, ITO
Poly (thiophene-2,5-diyl) was deposited on the transparent electrode at a deposition rate of 0.1 nm / sec to a thickness of 20 nm to form a first hole injecting and transporting layer. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was depressurized again to 3 × 10 ⁻⁶ Torr.
Then, the compound of Exemplified Compound 123 and rubrene were deposited from different vapor deposition sources at 55 nm at a vapor deposition rate of 0.2 nm / sec.
Was co-evaporated to a thickness of 10 (weight ratio 10: 1) to form a light emitting layer which also served as a second hole injecting and transporting layer. While maintaining the reduced pressure, tris (8-quinolinolato) aluminum was then vapor-deposited thereon at a vapor deposition rate of 0.2 nm / sec. To a thickness of 50 nm to form an electron injecting and transporting layer. While maintaining the reduced pressure state, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, which was used as an organic electroluminescence device. Was produced. A direct current voltage was applied to the produced organic electroluminescent device, and it was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. Initially 6.0V, brightness 5
A yellow emission of ²⁰ cd / m ² was confirmed. The half-life of brightness was 1600 hours.

Example 16 Preparation of Organic Electroluminescent Device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was treated with neutral detergent, semicoclean (manufactured by Furuuchi Chemical Co., Ltd.), ultrapure water, acetone, and ethanol. Used for ultrasonic cleaning. This substrate is dried using nitrogen gas, and further U
After V / ozone cleaning, the substrate was fixed to a substrate holder of a vapor deposition device, and the vapor deposition tank was depressurized to 3 × 10 ⁻⁶ Torr. First, ITO
Exemplified Compound 120 is deposited on the transparent electrode at a deposition rate of 0.1 nm.
/ Sec to a thickness of 20 nm to form a first hole injecting and transporting layer. After returning the vapor deposition tank to atmospheric pressure, the vapor deposition tank was depressurized again to 3 × 10 ⁻⁶ Torr. Next, Exemplified Compound 6
And rubrene were co-evaporated from different vapor deposition sources at a vapor deposition rate of 0.2 nm / sec to a thickness of 55 nm (weight ratio 10: 1) to form a light emitting layer also serving as a second hole injecting and transporting layer. . Then, tris (8-quinolinolato) aluminum is deposited thereon at a deposition rate of 0.2 nm / sec.
It was vapor-deposited to a thickness of nm to form an electron injecting and transporting layer. Further, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. The vapor deposition was carried out while keeping the vacuum state of the vapor deposition tank. A direct current voltage was applied to the produced organic electroluminescence device, and it was continuously driven at a constant current density of 10 mA / cm ² in a dry atmosphere. Initially, yellow light emission of 6.0 V and a luminance of 520 cd / m ² was confirmed. The half-life of brightness was 1700 hours.

Example 17 Preparation of Organic Electroluminescent Device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was treated with a neutral detergent, semicoclean (manufactured by Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. Used for ultrasonic cleaning. This substrate is dried using nitrogen gas, and further U
V / ozone cleaning was performed. Next, by using a 3 wt% dichloroethane solution containing polycarbonate (weight average molecular weight 39000) and the compound of Exemplified compound 20 in a weight ratio of 100: 50 on the ITO transparent electrode, a hole of 40 nm was formed by spin coating. An injection transport layer was formed. Next, the glass substrate having the hole injecting and transporting layer was fixed to a substrate holder of a vapor deposition device, and the vapor deposition layer was depressurized to 3 × 10 ⁻⁶ Torr. Next, tris (8-quinolinolato) aluminum was vapor-deposited thereon at a vapor deposition rate of 0.2 nm / sec. To a thickness of 50 nm 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 vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to form a cathode, and an organic electroluminescence device was produced. When a direct current voltage of 10 V was applied to the produced organic electroluminescent device in a dry atmosphere, it was 96 mA / c.
An electric current of m ² flowed. Green light emission with a luminance of 960 cd / m ² was confirmed. The half-life of brightness was 280 hours.

Example 18 Preparation of Organic Electroluminescent Device A glass substrate having a 200 nm thick ITO transparent electrode (anode) was treated with a neutral detergent, semicoclean (manufactured by Furuuchi Chemical Co., Ltd.), ultrapure water, acetone and ethanol. Used for ultrasonic cleaning. This substrate is dried using nitrogen gas, and further U
V / ozone cleaning was performed. Next, on the ITO transparent electrode, polymethylmethacrylate (weight average molecular weight 25,000),
Compound of Exemplified Compound 5, Tris (8-quinolinolato)
A 100-nm light emitting layer was formed by spin coating using a 3 wt% dichloroethane solution containing aluminum in a weight ratio of 100: 50: 0.5, respectively.
Next, the glass substrate having this light emitting layer was fixed to a substrate holder of a vapor deposition apparatus, and the vapor deposition layer was depressurized to 3 × 10 ⁻⁶ Torr. On the light emitting layer, magnesium and silver were co-deposited as a cathode at a vapor deposition rate of 0.2 nm / sec to a thickness of 200 nm (weight ratio 10: 1) to serve as a cathode, and an organic electroluminescence device was produced. In the prepared organic electroluminescent device in a dry atmosphere,
When a DC voltage of 15 V was applied, 82 mA / cm ²
Current flowed. Green light emission with a luminance of 540 cd / m ² was confirmed. The half-life of brightness was 490 hours.

[0164]

Industrial Applicability According to the present invention, it is possible to provide a novel amine compound and an organic electroluminescent device having a long emission life and excellent durability.

[Brief description of drawings]

FIG. 1 is a schematic cross-sectional view of an example of an organic electroluminescent device.

FIG. 2 is a schematic cross-sectional view of an example of an organic electroluminescent device.

FIG. 3 is a schematic cross-sectional view of an example of an organic electroluminescent device.

FIG. 4 is a schematic cross-sectional view of an example of an organic electroluminescent device.

FIG. 5 is a schematic cross-sectional view of an example of an organic electroluminescent device.

FIG. 6 is a schematic cross-sectional view of an example of an organic electroluminescent device.

FIG. 7 is a schematic cross-sectional view of an example of an organic electroluminescent device.

FIG. 8 is a schematic cross-sectional view of an example of an organic electroluminescent device.

[Explanation of symbols]

1: substrate 2: Anode 3: Hole injection transport layer 3a: hole injecting and transporting component 4: Light emitting layer 4a: luminous component 5: Electron injection transport layer 5 ": electron injection transport layer 5a: electron injection transport component 6: Cathode 7: Power supply

[Procedure amendment]

[Submission date] March 13, 2002 (2002.3.1)
3)

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be corrected] Claim 1

[Correction method] Change

[Correction content]

[Chemical 1] [In the formula, X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅ and A ₂₁ to
A ₂₅ represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkoxy group which may have a substituent, or a substituent. Linear chain optionally having, branched or cyclic alkylthio group, linear chain optionally having substituent, branched or cyclic alkenyl group, linear chain optionally having substituent,
A branched or cyclic alkenyloxy group, a linear or branched alkenylthio group which may have a substituent,
A linear, branched or cyclic aralkyl group which may have a substituent, a linear, branched or cyclic aralkylthio group which may have a substituent, a substituted or unsubstituted aryl group, a substituted or unsubstituted A substituted aryloxy group, a substituted or unsubstituted arylthio group, a cyano group, a hydroxyl group, a mercapto group, a -COOR ₁ group (in the group, R ₁ is a hydrogen atom, a straight chain which may have a substituent, a branched or Cyclic alkyl group,
A linear, branched or cyclic alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group) and a -COR ₂ group (wherein R ₂ is Hydrogen atom, linear or branched or cyclic alkyl group which may have a substituent, linear or branched or cyclic alkenyl group which may have a substituent, substituted or unsubstituted aralkyl group, substituted Or an unsubstituted aryl group or an amino group), an —OCOR ₃ group (in the group, R ₃ is a hydrogen atom, a straight chain which may have a substituent,
It represents a branched or cyclic alkyl group, a linear or branched alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group), or a formula ( 2) Group represented by (Chemical Formula 2)

[Chemical 2] (In the group, Y ₁ and Y ₂ are each a hydrogen atom, a linear or branched alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituent which may have a substituent. Represents a good aryl group, Y ₁ and Y ₂ may combine with each other to form a substituted or unsubstituted aromatic ring or aliphatic ring together with a nitrogen atom), A _{11 to} A ₁₅ and A ₂₁ to The adjacent groups of A ₂₅ are bonded to each other to form a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted carbocyclic aliphatic ring, a substituted or unsubstituted carbon atom with a carbon atom which is substituted.
An unsubstituted heterocyclic aromatic ring or a substituted or unsubstituted heterocyclic aliphatic ring may be formed, and at least one of A _{11 to} A ₁₅ and at least one of A _{21 to} A ₂₅ are represented by the formula ( 2) represents a group represented by

[Procedure Amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0012

[Correction method] Change

[Correction content]

(In the group, Y ₁ and Y _{2 each} have a hydrogen atom, a linear or branched alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituent. Represents an optionally substituted aryl group, Y ₁ and Y ₂
Represents a substituted or unsubstituted aromatic ring or aliphatic ring which may be bonded to each other together with a nitrogen atom), A
Adjacent groups of _{11 to} A ₁₅ and A _{21 to} A ₂₅ are bonded to each other to form a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted carbocyclic aliphatic group together with a carbon atom which is substituted. A ring, a substituted or unsubstituted heterocyclic aromatic ring, a substituted or unsubstituted heterocyclic aliphatic ring may be formed, and A _{11 to} A _11
At least one of ₁₅ and at least one of A _{21 to} A ₂₅ represents a group represented by the formula (2)]

[Procedure 3]

[Document name to be amended] Statement

[Correction target item name] 0020

[Correction method] Change

[Correction content]

(In the group, Y ₁ and Y _{2 each} have a hydrogen atom, a linear or branched or cyclic alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituent. Represents an optionally substituted aryl group, Y ₁ and Y ₂
Represents a substituted or unsubstituted aromatic ring or aliphatic ring which may be bonded to each other together with a nitrogen atom), A
Adjacent groups of _{11 to} A ₁₅ and A _{21 to} A ₂₅ are bonded to each other to form a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted carbocyclic aliphatic group together with a carbon atom which is substituted. A ring, a substituted or unsubstituted heterocyclic aromatic ring, a substituted or unsubstituted heterocyclic aliphatic ring may be formed, and A _{11 to} A _11
At least one of ₁₅ and at least one of A _{21 to} A ₂₅ represents a group represented by the formula (2)]

[Procedure amendment 4]

[Document name to be amended] Statement

[Correction target item name] 0104

[Correction method] Change

[Correction content]

Next, the organic electroluminescent device of the present invention will be described. The organic electroluminescent element of the present invention, between a pair of electrodes,
At least one layer containing at least one amine compound represented by the general formula (1) is sandwiched.
An organic electroluminescent device usually has at least one electrode between a pair of electrodes.
At least one light emitting layer containing two kinds of light emitting components is sandwiched. Considering the respective functional levels of hole injection and hole transport, electron injection and electron transport of the compound used for the light emitting layer, and if desired, a hole injection transport layer and / or electron injection containing a hole injection component. An electron injecting and transporting layer containing a transporting component can also be provided.

[Procedure Amendment 5]

[Document name to be amended] Statement

[Correction target item name] 0107

[Correction method] Change

[Correction content]

In the organic electroluminescent device of the present invention, the amine compound represented by the general formula (1) is preferably used as a constituent component of the hole injecting and transporting layer and / or the light emitting layer, and the hole injecting and transporting layer. More preferably, it is used as a constituent component of In the organic electroluminescent device of the present invention,
The amine compound represented by the general formula (1) may be used alone or in combination.

[Procedure correction 6]

[Document name to be amended] Statement

[Correction target item name] 0118

[Correction method] Change

[Correction content]

The hole injecting / transporting layer comprises the compound represented by the general formula (1) and / or another compound having a hole injecting / transporting function (eg, phthalocyanine derivative, triarylamine derivative, triarylmethane derivative, oxazole). Derivative, hydrazone derivative, stilbene derivative, pyrazoline derivative, polysilane derivative, polyphenylene vinylene and its derivative, polythiophene and its derivative, poly-N-vinylcarbazole, etc.)
It can be formed by using one kind. The compounds having a hole injection / transport function may be used alone or in combination of two or more.

[Procedure Amendment 7]

[Document name to be amended] Statement

[Name of item to be corrected] 0119

[Correction method] Change

[Correction content]

The organic electroluminescent device of the present invention preferably contains the amine compound represented by the general formula (1) in the hole injecting and transporting layer. As the compound having a hole injecting and transporting function other than the amine compound represented by the general formula (1) of the present invention which can be used in the organic electroluminescent device of the present invention, a triarylamine derivative (for example, 4,4) is used. '-
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,
1,1-bis [4 '-[N, N-di (4 "-methylphenyl) amino] phenyl] cyclohexane, 9,10-
Bis [N- (4'-methylphenyl) -N- (4 "-n
-Butylphenyl) amino] phenanthrene, 3,8-
Bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-N, N-bis [4 ″,
4 "'-bis [N', N'-di (4-methylphenyl)
Amino] biphenyl-4-yl] aniline, N, N'-
Bis [4- (diphenylamino) phenyl] -N, N '
-Diphenyl-1,3-diaminobenzene, N, N'-
Bis [4- (diphenylamino) phenyl] -N, N '
-Diphenyl-1,4-diaminobenzene, 5,5 "-
Bis [4- (bis [4-methylphenyl] amino] phenyl-2,2 ′: 5 ′, 2 ″ -terthiophene, 1,
3,5-tris (diphenylamino) benzene, 4,
4 ', 4 "-tris (N-carbazolyyl) triphenylamine, 4,4', 4" -tris [N, N-bis (4 "'-tert-butylbiphenyl-4""-yl) amino] tri Phenylamine, 1,3,5-tris [N-
More preferred are polythiophene and its derivatives, such as (4′-diphenylamino] benzene, and poly-N-vinylcarbazole and its derivatives.

[Procedure Amendment 8]

[Document name to be amended] Statement

[Correction target item name] 0120

[Correction method] Change

[Correction content]

When the amine compound represented by the general formula (1) and another compound having a hole injecting function are used in combination, the amine compound represented by the general formula (1) is contained in the hole injecting and transporting layer. The amount is preferably 0.1% by weight or more, more preferably 0.5 to 99.9% by weight, further preferably 3 to 97% by weight. The light emitting layer 4 is a layer containing a compound having a function of injecting holes and electrons, a function of transporting them, and a function of generating excitons by recombination of holes and electrons.

[Procedure Amendment 9]

[Document name to be amended] Statement

[Correction target item name] 0121

[Correction method] Change

[Correction content]

In the light emitting layer, an amine compound represented by the general formula (1) is used as a host material, and a compound having a light emitting function other than the amine compound represented by the general formula (1) is used as at least one guest material. Can be formed.

[Procedure Amendment 10]

[Document name to be amended] Statement

[Name of item to be corrected] 0122

[Correction method] Change

[Correction content]

As the compound (guest material) having a light emitting function other than the amine compound represented by the general formula (1), for example, acridone derivative, quinacridone derivative, diketopyrrolopyrrole derivative, polycyclic aromatic compound [eg, Rubrene, anthracene, tetracene, pyrene, perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10
-Bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthocenyl) benzene, 4,4 '
-Bis (9 "-ethynylanthracenyl) biphenyl,
Dibenzo [f, f] diindeno [1,2,3-cd: 1 ', 2', 3'-lm]
Perylene derivative], a triarylamine derivative (for example, the compound described above can be mentioned as a compound having a hole injecting and transporting function), an organometallic complex [for example,
Tris (8-quinolinolato) aluminum, bis (1
0-benzo [h] quinolinolato) beryllium, 2-
Zinc salt of (2′-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine, zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone],
Stilbene derivatives [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 derivative (for example, coumarin 1, coumarin 6, coumarin 7, coumarin 30, coumarin 106, coumarin 138) , Coumarin 151, Coumarin 152, Coumarin 153, Coumarin 307, Coumarin 311, Coumarin 314, Coumarin 334, Coumarin 338, Coumarin 3
43, coumarin 500), pyran derivative (eg DC
M1, DCM2), oxazone derivative (for example, Nile red), benzothiazole derivative, benzoxazole derivative, benzimidazole derivative, pyrazine derivative, cinnamic acid ester derivative, poly-N-vinylcarbazole and its derivative, polythiophene and its derivative. , Polyphenylene and its derivatives, polyfluorene and its derivatives, polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and its derivatives, polythienylene vinylene and its derivatives, etc. Can be mentioned.
As the compound (guest material) having a light emitting function other than the amine compound represented by the general formula (1), acridone derivative, quinacridone derivative, polycyclic aromatic compound, triarylamine derivative, organometallic complex and stilbene derivative are preferable. More preferred are polycyclic aromatic compounds and organometallic complexes.

[Procedure Amendment 11]

[Document name to be amended] Statement

[Name of item to be corrected] 0123

[Correction method] Change

[Correction content]

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

[Procedure Amendment 12]

[Document name to be amended] Statement

[Correction target item name] 0124

[Correction method] Change

[Correction content]

When the amine compound represented by the general formula (1) is used as a host material in combination with another compound having a light emitting function, the content of the amine compound represented by the general formula (1) in the light emitting layer. Is preferably 40.0% to 99.
It is 9%, and more preferably 60.0 to 99.9% by weight.

[Procedure Amendment 13]

[Document name to be amended] Statement

[Name of item to be corrected] 0125

[Correction method] Change

[Correction content]

The amount of the guest material used is 0.001 to 40% by weight based on the amine compound represented by the general formula (1).
Preferably 0.05 to 30% by weight, more preferably
It is 0.1 to 20% by weight. The guest materials may be used alone or in combination of two or more.

Front page continuation (51) Int.Cl. ⁷ Identification code FI theme code (reference) H05B 33/22 H05B 33/22 B (72) Inventor Yoshiyuki Toya 580-32 Nagaura, Sodegaura-shi, Chiba Mitsui Chemicals Co., Ltd. (72) Inventor Masakatsu Nakatsuka 580-32 Nagaura, Sodegaura-shi, Chiba Mitsui Chemicals Co., Ltd. F-term (reference) 3K007 AB00 AB04 AB13 BA06 BB06 CA01 CA02 CA05 CA06 CB01 DA00 EB00 FA01 4H006 AA01 AA02 AA03 AB78 AC23 AC28 AC52 AD17 BA05 BA25 BA37 BA48 BB11 BC10 BC19 BE10

Claims (10)

[Claims] 1. An amine compound represented by the general formula (1) (formula 1). [Chemical 1] [In the formula, X ₁ , X ₂ , X ₃ , X ₄ , A _{11 to} A ₁₅ and A ₂₁ to
A ₂₅ represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkoxy group which may have a substituent, or a substituent. Linear chain optionally having, branched or cyclic alkylthio group, linear chain optionally having substituent, branched or cyclic alkenyl group, linear chain optionally having substituent,
A branched or cyclic alkenyloxy group, a linear or branched alkenylthio group which may have a substituent,
A linear, branched or cyclic aralkyl group which may have a substituent, a linear, branched or cyclic aralkylthio group which may have a substituent, a substituted or unsubstituted aryl group, a substituted or unsubstituted A substituted aryloxy group, a substituted or unsubstituted arylthio group, a cyano group, a hydroxyl group, a mercapto group, a -COOR ₁ group (in the group, R ₁ is a hydrogen atom, a straight chain which may have a substituent, a branched or Cyclic alkyl group,
A linear, branched or cyclic alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group) and a -COR ₂ group (wherein R ₂ is Hydrogen atom, linear or branched or cyclic alkyl group which may have a substituent, linear or branched or cyclic alkenyl group which may have a substituent, substituted or unsubstituted aralkyl group, substituted Or an unsubstituted aryl group or an amino group), an —OCOR ₃ group (in the group, R ₃ is a hydrogen atom, a straight chain which may have a substituent,
It represents a branched or cyclic alkyl group, a linear or branched alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group), or a formula ( 2) Group represented by (Chemical formula 2) (In the group, Y ₁ and Y ₂ are each a hydrogen atom, a linear or branched alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or a substituent which may have a substituent. Represents a good aryl group, Y ₁ and Y ₂ may combine with each other to form a substituted or unsubstituted aromatic ring or aliphatic ring together with a nitrogen atom), A _{11 to} A ₁₅ and A ₂₁ to The adjacent groups of A ₂₅ are bonded to each other to form a substituted or unsubstituted carbocyclic aromatic ring, a substituted or unsubstituted carbocyclic aliphatic ring, a substituted or heterocyclic aromatic group together with a substituted carbon atom. A group ring, a substituted or unsubstituted heterocyclic aliphatic ring may be formed, and at least one of A _{11 to} A ₁₅
At least one of A _{21 to} A ₂₅ represents a group represented by the formula (2)] 2. An amine compound represented by the general formula (1)
X₁, X₂, X ₃And X_FourAt least one of
The aryl group according to claim 1, which is a substituted or unsubstituted aryl group.
Min compound. 3. In the group represented by the formula (2), Y ₁ and Y ₂ may be a linear, branched or cyclic alkyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or A substituted or unsubstituted aryl group.
Or the amine compound described in 2. 4. The amine compound according to claim 1, 2 or 3, wherein Y ₁ and Y ₂ in the group represented by the formula (2) are substituted or unsubstituted aryl groups. 5. A compound represented by the general formula (3) (Chemical Formula 3):
A method for producing an amine compound represented by the general formula (1), which comprises reacting a compound represented by the general formula (4) (formula 3). [Chemical 3] 6. An organic electroluminescent device comprising a pair of electrodes and at least one layer containing at least one amine compound represented by the general formula (1) sandwiched between the pair of electrodes. 7. The organic electroluminescent device according to claim 6, wherein the layer containing the amine compound represented by the general formula (1) is a hole injecting and transporting layer. 8. The organic electroluminescent device according to claim 6, wherein the layer containing the amine compound represented by the general formula (1) is a light emitting layer. 9. The organic electroluminescent device according to claim 6, further comprising a light emitting layer between the pair of electrodes. 10. The organic electroluminescent device according to claim 6, further comprising an electron injecting and transporting layer between the pair of electrodes.