JPH09311489A - Electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To ensure superior wear resistance at the time of repetitive use and high sensitivity and to reduce residual potential by forming a photosensitive layer contg. a specified high molecular electric charge transferring material and a specified azo pigment. SOLUTION: This electrophotographic photoreceptor has a photosensitive layer contg. a high molecular electric charge transferring material represented by formula I and an azo pigment represented by formula II. In the formula I, each of R"1 -R"3 is optionally substd. alkyl or halogen, R"4 is H or optionally substd. alkyl, each of R1 and R2 is optionally substd. aryl, each of (o), (p) and (q) is an integer of 0-4, the ratio of k:j is (0.1-1):(0-0.9), (n) is an integer of 5-5,000 as the number of repeating units and X is a divalent aliphatic group, etc. In the formula II, each of Cp1 and Cp2 is a residue of a coupler and each of R'1 -R'3 is H, halogen, etc.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member, and more particularly to an electrophotographic photosensitive member which is preferably used in a copying machine, a laser printer, a laser facsimile and the like.

[0002]

2. Description of the Related Art As an electrophotographic method, the Carlson process and various deformation processes thereof are known, and are widely used in copying machines and printers. Among the photoconductors used in such an electrophotographic method, those using an organic photosensitive material have recently begun to be used because of advantages such as low cost, mass productivity, and pollution-free property.

[0003] Organic electrophotographic photoreceptors include a photoconductive resin represented by polyvinyl carbazole (PVK), P
VK-TNF (2,4,7-trinitrofluorenone)
A charge transfer complex type represented by, a pigment dispersion type represented by a phthalocyanine-binder, a function-separated type photoreceptor using a combination of a charge-generating substance and a charge-transporting substance are known. Electrophotographic photoreceptors of the type are receiving attention. The mechanism of electrostatic latent image formation in this function-separated type electrophotographic photoreceptor is that when the photoreceptor is charged and then irradiated with light, the light passes through the transparent charge transport layer and the charge-generating substance in the charge-generating layer. The charge-generating substance that is absorbed by the light and absorbs light generates charge carriers, which are injected into the charge-transporting layer and move in the charge-transporting layer according to the electric field generated by the charging, so that the charge on the surface of the photoreceptor is charged. To form an electrostatic latent image.

In the function-separated type electrophotographic photosensitive member,
It is known and useful to use a combination of a charge transporting substance having an absorption mainly in the ultraviolet region and a charge generating substance having an absorption mainly in the visible region. Many of the charge-transporting substances used in the charge-transporting layer have been developed as low-molecular weight compounds, but low-molecular weight compounds alone have no film-forming property.
It is usually used by dispersing and mixing it in an inert polymer.

However, the charge transport layer composed of a low molecular weight charge transport material and an inert polymer is generally soft, and has a drawback that film abrasion due to repeated use tends to occur in the Carlson process. In addition, the charge transport layer having this configuration has a limit in charge mobility, which has been an obstacle to speeding up or downsizing of the Carlson process. This is usually
This is because the low molecular weight charge transport material is used in the charge transport layer at a content of 50% by weight or less, and it is possible to increase the charge mobility to some extent by increasing the content of the low molecular weight charge transport material. However, when the content of the low-molecular weight charge transporting substance is increased, the film forming property is deteriorated and the film abrasion due to repeated use becomes large.

In order to remedy such drawbacks, attention has been paid to high-molecular-weight charge transport materials.
056, JP-A-51-73888, JP-A-54-8527, JP-A-54-11737, JP-A-56-150749, and JP-A-57-7-7
8402, JP-A-63-285552, JP-A-1-17228, JP-A-1-19049, and JP-A-3-50555 disclose polymer type charge transport materials. . When these polymer-type charge transporting substances are used, the charge transporting layer can be composed of only a polymer compound, so that the charge transporting layer has good film-forming properties, high mechanical strength, and excellent wear resistance. A transport layer can be obtained, and film scraping due to repeated use can be prevented. However, the function-separated type electrophotographic photoreceptor that uses a combination of charge generation and a polymer charge transport material has a lower photosensitivity and a higher residual potential than when a low molecular charge transport material is used. There are drawbacks.

[0007]

SUMMARY OF THE INVENTION Therefore, the object of the present invention is to solve such problems and to provide an electrophotographic apparatus comprising a conductive support and a photosensitive layer containing a charge generating substance and a polymer charge transporting substance. It is an object of the present invention to provide an electrophotographic photosensitive member which is excellent in abrasion resistance during repeated use, has high sensitivity, and has a small residual potential.

[0008]

The above object of the present invention is to provide an electrophotographic photosensitive member comprising a conductive support and a photosensitive layer, the photosensitive layer being represented by the following general formulas (1D) to (10D). And an azo pigment represented by the following general formulas (1P) to (10P).

By using the high molecular weight charge transporting substances represented by the general formulas (1D) to (10D), the electrophotographic photosensitive material has good film-forming property of the photosensitive layer and excellent abrasion resistance during repeated use. By using the azo pigments represented by the general formulas (1P) to (10P) together with these polymer charge-transporting substances, an electrophotographic photoconductor having high sensitivity and low residual potential can be obtained. Obtainable.

The polymer charge transport materials represented by the general formulas (1D) to (10D) used in the electrophotographic photoreceptor of the present invention will be described below.

Embedded image {In the formula, R ″ ₁ , R ″ ₂ and R ″ ₃ each independently represent a substituted or unsubstituted alkyl group or a halogen atom, and R ″ ₄ represents a hydrogen atom or a substituted or unsubstituted alkyl group. . R ₁ and R ₂ represent a substituted or unsubstituted aryl group. o, p, and q each independently represent an integer of 0 to 4. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula (A).

[Chemical 132] [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O—, —CO—O—Z—O—CO— (wherein Z represents an aliphatic divalent group) or the following general formula (B)

Embedded image (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]｝

The alkyl group of R ″ ₁ , R ″ ₂ and R ″ ₃ is preferably C _{1 to} C _12, especially C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight or branched chain alkyl. The base,
These alkyl groups are further substituted with a fluorine atom, a hydroxyl group, a cyano group, a C ₁ -C ₄ alkoxy group, a phenyl group, or a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. It may also contain a phenyl group.
Specifically, a methyl group, an ethyl group, an n-propyl group, i
-Propyl group, t-butyl group, s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group Group, benzyl group, 4-chlorobenzyl group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the substituted or unsubstituted alkyl group of R ″ ₄ include R ″ ₁ , R ″ ₂ and R ″ described above.
_{The same as 3} is mentioned. The aryl group of R ₁ and R ₂ is an aromatic hydrocarbon group such as phenyl group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group. Group, chrysenyl group, fluorenylidenephenyl group, condensed polycyclic group such as 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycyclic group such as biphenylyl group and terphenylyl group, cenyl group, benzocenyl group , A furyl group, a benzofuranyl group,
Heterocyclic groups such as a carbazolyl group may be mentioned.

The above aryl group may have the following groups as a substituent. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: The same groups as those shown above as the alkyl group for R ″ ₁ , R ″ ₂ , and R ″ ₃ are mentioned. (3) Alkoxy group (—OR ₄₁ ): R ₄₁ is the same as the above ( 2) represents an alkyl group, specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When X is polymerized with a diol compound having a triarylamino group represented by the following general formula (1D ') by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (C) is used in combination. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is also introduced into the repeating unit by a polymerization reaction of a diol compound having a triarylamino group of the following general formula (1D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0014]

Embedded image The following may be mentioned as specific examples of the diol compound of the general formula (C). l, 3-propanediol, 1,4
-Butanediol, 1,5-pentanediol, 1,6
-Hexanediol, 1,8-octanediol, 1,
10-decanediol, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-ethyl-1,3-propanediol, diethylene glycol, triethylene glycol, polyethylene glycol, poly Aliphatic diols such as tetramethylene ether glycol, 1,4-cyclohexanediol,
1,3-cyclohexanediol, cyclohexane-
Examples thereof include cycloaliphatic diols such as 1,4-dimethanol.

As the diol having an aromatic ring,
4,4'-dihydroxydiphenyl, bis (4-hydroxyphenyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, 1,1bis (4-hydroxyphenyl) -1-phenylethane, 2,2- Bis (4-hydroxyphenyl) propane, 2,2-bis (3-methyl-
4-hydroxyphenyl) propane, 1,1-bis (4
-Hydroxyphenyl) cyclohexane, 1,1-bis (4-hydroxyphenyl) cyclopentane, 2,2-
Bis (3-phenyl-4-hydroxyphenyl) propane, 2,2-bis (3-isopropyl-4-hydroxyphenyl) propane, 2,2-bis (4-hydroxyphenyl) butane, 2,2-bis (3 , 5-dimethyl-4
-Hydroxyphenyl) propane, 2,2-bis (3,
5-dibromo-4-hydroxyphenyl) propane,
4,4'-dihydroxydiphenyl sulfone, 4,4 '
-Dihydroxydiphenyl sulphoxide, 4,4'-dihydroxydiphenyl sulphide, 3,3'-dimethyl-4,4'-dihydroxydiphenyl sulphide, 4,
4'-dihydroxydiphenyl oxide, 2,2-bis (4-hydroxyphenyl) hexafluoropropane,
9,9-bis (4-hydroxyphenyl) fluorene,
9,9-bis (4-hydroxyphenyl) xanthene,
Ethylene glycol-bis (4-hydroxybenzoate), diethylene glycol-bis (4-hydroxybenzoate), triethylene glycol-bis (4-hydroxybenzoate), 1,3-bis (4-hydroxyphenyl) -tetramethyldisiloxane, Phenol-modified silicone oils and the like can be mentioned. Next, the polymer charge transport material represented by the general formula (2D) is shown.

[0016]

[Chemical 135] [Wherein, R ₃ and R ₄ represent a substituted or unsubstituted aryl group, and Ar ₁ , Ar ₂ , and Ar ₃ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. X represents the same group as in the general formula (1D). As the aryl group of R ₃ and R ₄ , an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, A condensed polycyclic group such as a triphenylenyl group, a chrysenyl group, a fluorenylidenephenyl group, a 5H-dibenzo [a, d] cycloheptenylidenephenyl group, a heterocyclic group such as a cenyl group, a benzocenyl group, a furyl group, a benzofuranyl group, and a carbazolyl group. Examples thereof include a cyclic group, a biphenylyl group, a terphenylyl group, and a non-fused polycyclic group represented by the following general formula (A).

[0017]

[Chemical 136] Wherein W is -O-, -S-, -SO-, -SO
_2- , -CO- and the following general formulas (b), (c),
(D) represents a divalent group shown in (e).

[0018]

[Chemical 137] (In the formula, c represents an integer of 1 to 12, and d, e, and f are 1 to 12.
Represents an integer of 3. )]

The arylene group of Ar ₁ , Ar ₂ and Ar ₃ includes the divalent group of the aryl group represented by R ₃ and R ₄ . R ₃ , R ₄ aryl group, Ar ₁ , Ar ₂ , Ar
The arylene group ₃ may have the following groups as substituents. Further, these substituents are represented by the above general formula (A),
It is also a specific example of R ₃₁ , R ₃₂ and R ₃₃ in (d) and (e). (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) A substituted amino group represented by the general formula -N ( _R42 ) ( _R43 ). (In the formula, R ₄₂ and R ₄₃ each independently represent the alkyl group shown in the above (2) or the aryl group shown in the above R ₃ and R ₄ , and preferable examples of the aryl group include a phenyl group and a biphenyl group. Or a naphthyl group, which may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent, and a ring together with a carbon atom on the aryl group. Specifically, a diethylamino group, an N-methyl-N-phenylamino group, an N, N-diphenylamino group, an N, N-di (p-tolyl) amino group, a dibenzylamino group may be formed. , A piperidino group, a morpholino group, a euroridyl group, etc. (7) An alkylenedioxy group or an alkylenedithio group such as a methylenedioxy group or a methylenedithio group.

When X is polymerized with a diol compound having a triarylamino group represented by the following general formula (2D ') by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (C) is used in combination. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is introduced into the repeating unit also by a polymerization reaction of a diol compound having a triarylamino group of the following general formula (2D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0021]

[Chemical 138] Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). Next, the polymer charge transport material represented by the general formula (3D) is shown.

[0022]

Embedded image [In the formula, R ₅ and R ₆ represent a substituted or unsubstituted aryl group, and Ar ₄ , Ar ₅ and Ar ₆ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. X represents the same group as in the general formula (1D). As the aryl group of R ₅ and R ₆ , an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, Condensed polycyclic group such as triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycyclic group such as biphenylyl group, terphenylyl group, cenyl group, benzocenyl Group, furyl group,
Heterocyclic groups such as a benzofuranyl group and a carbazolyl group are exemplified. Further, the arylene group of Ar ₄ , Ar ₅ and Ar ₆ includes the divalent group of the aryl group represented by R ₅ and R ₆ . Aryl group of R ₅ and R ₆ , Ar ₄ , Ar ₅ and A
The arylene group of r ₆ may have a group shown below as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When X is polymerized with a diol compound having a triarylamino group represented by the following general formula (3D ') by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (C) is used in combination. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is also introduced into the repeating unit by a polymerization reaction of a diol compound having a triarylamino group of the following general formula (3D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0025]

Embedded image Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). Next, the polymer charge transport material represented by the general formula (4D) is shown.

[0026]

[Chemical 141] [In the formula, R ₇ and R ₈ represent a substituted or unsubstituted aryl group, and Ar ₇ , Ar ₈ , and Ar ₉ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. r represents an integer of 1 to 5. X represents the same group as in the general formula (1D). As the aryl group of R ₇ and R ₈ , an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, Condensed polycyclic group such as triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycyclic group such as biphenylyl group, terphenylyl group, cenyl group, benzocenyl Group, furyl group,
Heterocyclic groups such as a benzofuranyl group and a carbazolyl group are exemplified. The arylene groups of Ar ₇ , Ar ₈ and Ar ₉ include the divalent groups of the aryl groups represented by R ₇ and R ₈ . R ₇ , R ₈ aryl groups, Ar ₇ , Ar ₈ , A
The arylene group of r ₉ may have a group shown below as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

When X is a diol compound having a triarylamino group represented by the following general formula (4D ') which is polymerized by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (C) is used in combination. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is also introduced into the repeating unit by a polymerization reaction of a diol compound having a triarylamino group represented by the following general formula (4D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0029]

[Chemical 142] Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). Next, the polymer charge transport material represented by the general formula (5D) is shown.

[0030]

[Chemical 143] [In the formula, R ₉ and R ₁₀ represent a substituted or unsubstituted aryl group, and Ar ₁₀ , Ar ₁₁ , and Ar ₁₂ represent the same or different arylene groups. X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group.
k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9.
And n represents the number of repeating units and is an integer of 5 to 5000. X represents the same group as in the general formula (1D). As the aryl group of R ₉ and R ₁₀ , an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, Condensed polycyclic groups such as triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycyclic groups such as biphenylyl group and terphenylyl group, cenyl group, benzocenyl And a heterocyclic group such as a furyl group, a benzofuranyl group and a carbazolyl group. Further, the arylene group of Ar ₁₀ , Ar ₁₁ and Ar ₁₂ includes 2 of the aryl groups represented by R ₉ and R _10.
Valence groups. Aryl group of R ₉ and R ₁₀ , A
The arylene groups of r ₁₀ , Ar ₁₁ and Ar ₁₂ may have the following groups as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group. Examples of the substituent of the ethylene group or the vinylene group of X ₁ and X ₂ include a cyano group, a halogen atom, a nitro group, the aryl group of R ₉ and R ₁₀ above, and the alkyl group of (2) above.

When X is polymerized with a diol compound having a triarylamino group represented by the following general formula (5D ') by the phosgene method, transesterification method or the like, a diol compound represented by the following general formula (C) is used in combination. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is introduced into the repeating unit also by a polymerization reaction of a diol compound having a triarylamino group represented by the following general formula (5D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0033]

[Chemical 144] Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). Next, the polymer charge transport material represented by the general formula (6D) is shown.

[0034]

Embedded image [Wherein, R ₁₁ , R ₁₂ , R ₁₃ , and R ₁₄ represent a substituted or unsubstituted aryl group, and Ar ₁₃ , Ar ₁₄ , Ar ₁₅ , Ar ₁₆
Represents the same or different arylene groups. Y ₁ , Y ₂ , Y ₃
Represents a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, a sulfur atom or a vinylene group, which may be the same or different Good. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦
0.9, and n represents the number of repeating units, and is 5 to 500
It is an integer of 0. X represents the same group as in the general formula (1D). ]

The aryl group of R ₁₁ , R ₁₂ , R ₁₃ and R ₁₄ is an aromatic hydrocarbon group such as phenyl group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group. Groups, azulenyl groups, anthryl groups, triphenylenyl groups, chrysenyl groups, fluorenylidenephenyl groups, condensed polycyclic groups such as 5H-dibenzo [a, d] cycloheptenylidenephenyl groups, non-condensed biphenylyl groups, terphenylyl groups, etc. Polycyclic group, cenyl group, benzocenyl group, furyl group, benzofuranyl group,
Heterocyclic groups such as a carbazolyl group may be mentioned. The arylene group of Ar ₁₃ , Ar ₁₄ , Ar ₁₅ and Ar ₁₆ is 2 of the aryl groups represented by R ₁₁ , R ₁₂ , R ₁₃ and R _14.
Valence groups. The above aryl group or arylene group may have a group shown below as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

As the alkylene group for Y ₁ , Y ₂ and Y ₃ ,
The divalent group derived from the alkyl group shown in the above (2) may be mentioned. Specifically, a methylene group, an ethylene group,
1,3-propylene group, 1,4-butylene group, 2-methyl-1,3-propylene group, difluoromethylene group, hydroxyethylene group, cyanoethylene group, methoxyethylene group, phenylmethylene group, 4-methylphenylmethylene group Group, 2,2-propylene group, 2,2-butylene group,
Examples thereof include a diphenylmethylene group. Examples of the cycloalkylene group include a 1,1-cyclopentylene group, a 1,1-cyclohexylene group and a 1,1-cyclooctylene group. Examples of the alkylene ether group include a dimethylene ether group, a diethylene ether group, an ethylene methylene ether group, a bis (triethylene) ether group, and a polytetramethylene ether group.

When X is a diol compound having a triarylamino group represented by the following general formula (6D ') is polymerized by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (C) is used in combination. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is introduced into the repeating unit also by a polymerization reaction of a diol compound having a triarylamino group of the following general formula (6D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0039]

[Chemical 146] Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). Next, the polymer charge transport material represented by the general formula (7D) is shown.

[0040]

[Chemical 147] [In the formula, R ₁₅ and R ₁₆ represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁₅ and R ₁₆ may form a ring. Ar ₁₇ , Ar ₁₈ and Ar ₁₉ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦ 1,
0 ≦ j ≦ 0.9, and n represents the number of repeating units.
It is an integer of ５5000. X represents the same group as in the general formula (1D). ]

The aryl group of R ₁₅ and R ₁₆ is an aromatic hydrocarbon group such as phenyl group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group. Group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, condensed polycyclic group such as 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycyclic group such as biphenylyl group, terphenylyl group, cenyl group And heterocyclic groups such as benzocenyl group, furyl group, benzofuranyl group and carbazolyl group. Examples of the case where R ₁₅ and R ₁₆ form a ring include 9-fluoridene and 5H-dibenzo [a, d] cycloheptenylidene. As the arylene group of Ar ₁₇ , Ar ₁₈ and Ar ₁₉ , the divalent group of the aryl group represented by R ₁₅ and R ₁₆ can be mentioned. Aryl groups for R ₁₅ and R ₁₆ , Ar ₁₇ , Ar ₁₈ , Ar
The arylene group of ₁₉ may have the following groups as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

X is obtained by using a diol compound of the following general formula (C) together when polymerizing a diol compound having a triarylamino group of the following general formula (7D ') by the phosgene method, transesterification method or the like. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is introduced into the repeating unit also by a polymerization reaction of a diol compound having a triarylamino group represented by the following general formula (7D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0044]

Embedded image Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). Next, the polymer charge transport material represented by the general formula (8D) is shown.

[0045]

Embedded image [Wherein, R ₁₇ represents a substituted or unsubstituted aryl group, and Ar ₂₀ , Ar ₂₁ , Ar ₂₂ , and Ar ₂₃ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k
≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X is the general formula (1
Represents the same groups as in D). ]

The aryl group of R ₁₇ includes aromatic hydrocarbon groups such as phenyl group, naphthyl group, pyrenyl group, 2-
Fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H
A condensed polycyclic group such as dibenzo [a, d] cycloheptenylidenephenyl group, a non-condensed polycyclic group such as biphenylyl group and terphenylyl group, a cenyl group, a benzocenyl group,
Heterocyclic groups such as furyl group, benzofuranyl group and carbazolyl group are exemplified. In addition, Ar ₂₀ , Ar ₂₁ , Ar
Examples of the arylene group of ₂₂ and Ar ₂₃ include the divalent group of the aryl group represented by R ₁₇ . An aryl group of R ₁₇ , Ar
The arylene groups of ₂₀ , Ar ₂₁ , Ar ₂₂ , and Ar ₂₃ may have the following groups as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

X is obtained by using a diol compound of the following general formula (C) together when polymerizing a diol compound having a triarylamino group of the following general formula (8D ') by the phosgene method, transesterification method or the like. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is introduced into the repeating unit also by a polymerization reaction of a diol compound having a triarylamino group represented by the following general formula (8D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0049]

[Chemical 150] Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). Next, the polymer charge transport material represented by the general formula (9D) is shown.

[0050]

Embedded image [Wherein, R ₁₈ , R ₁₉ , R ₂₀ , and R ₂₁ represent a substituted or unsubstituted aryl group, and Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , A
r ₂₇ and Ar ₂₈ represent the same or different arylene groups.
k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9.
And n represents the number of repeating units and is an integer of 5 to 5000. X represents the same group as in the general formula (1D). ] As an aryl group of R ₁₈ , R ₁₉ , R ₂₀ , and R ₂₁ , an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, Condensed polycyclic groups such as azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycycles such as biphenylyl group and terphenylyl group And a heterocyclic group such as a group, a cenyl group, a benzocenyl group, a furyl group, a benzofuranyl group, and a carbazolyl group. In addition, Ar ₂₄ , Ar
The arylene groups of ₂₅ , Ar ₂₆ , Ar ₂₇ and Ar ₂₈ include R
_The divalent group of the aryl group represented by ₁₈ , R ₁₉ , R ₂₀ , and R ₂₁ may be mentioned. The aryl group or the arylene group may have a group shown below as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

X is obtained by using a diol compound of the following general formula (C) together when polymerizing a diol compound having a triarylamino group of the following general formula (9D ') by the phosgene method, transesterification method or the like. It is introduced into the main chain. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also, X
Is introduced into the repeating unit also by a polymerization reaction of a diol compound having a triarylamino group represented by the following general formula (9D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0053]

[Chemical 152] Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). Next, the polymer charge transport material represented by the general formula (10D) is shown.

[0054]

Embedded image [In the formula, R ₂₂ and R ₂₃ represent a substituted or unsubstituted aryl group, and Ar ₂₉ , Ar ₃₀ , and Ar ₃₁ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦
1, 0 ≦ j ≦ 0.9, and n represents the number of repeating units, and is an integer of 5 to 5000. X is the general formula (1
Represents the same groups as in D). As the aryl group of R ₂₂ and R ₂₃ , an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, Condensed polycyclic groups such as triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycyclic groups such as biphenylyl group and terphenylyl group, cenyl group, benzocenyl And a heterocyclic group such as a furyl group, a benzofuranyl group and a carbazolyl group. The arylene groups of Ar ₂₉ , Ar ₃₀ , and Ar ₃₁ are the aryl groups represented by R ₂₂ and R _23.
Valence groups. Allyl groups of R ₂₂ and R ₂₃ , Ar ₂₉ ,
The arylene groups of Ar ₃₀ and Ar ₃₁ may have the following groups as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Alkyl group: preferably C ₁ -C _12, especially C ₁
To C ₈ , more preferably a C _{1 to} C ₄ linear or branched alkyl group, and these alkyl groups are furthermore a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group,
It may contain a phenyl group or a phenyl group substituted with a halogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ alkoxy group. Specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a t-butyl group,
s-butyl group, n-butyl group, i-butyl group, trifluoromethyl group, 2-hydroxyethyl group, 2-cyanoethyl group, 2-ethoxyethyl group, 2-methoxyethyl group, benzyl group, 4-chlorobenzyl Group, 4-methylbenzyl group, 4-methoxybenzyl group, 4-phenylbenzyl group and the like. (3) Alkoxy group (-OR ₄₁ ): R ₄₁ represents the alkyl group shown in the above (2). Specifically, a methoxy group,
Ethoxy, n-propoxy, i-propoxy, t
-Butoxy group, n-butoxy group, s-butoxy group, i-
Butoxy group, 2-hydroxyethoxy group, 2-cyanoethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like. (4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group or a halogen atom as a substituent. Specifically, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group,
4-methylphenoxy group, 4-methoxyphenoxy group,
4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. (5) Substituted mercapto group or arylmercapto group:
Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group. (6) alkyl-substituted amino group: the alkyl group is as defined in the above (2)
Represents an alkyl group represented by. Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group. (7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.

X is the following general formula (C) when the diol compound having a triarylamino group of the following general formula (10D ') is polymerized by the phosgene method, the transesterification method or the like.
It is introduced into the main chain by using the above diol compound in combination. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. Also,
X is also introduced into the repeating unit by a polymerization reaction of a diol compound having a triarylamino group represented by the following general formula (10D ′) and a bischloroformate derived from the following general formula (C). In this case, the polycarbonate produced is an alternating copolymer.

[0057]

Embedded image Specific examples of the diol compound of the general formula (C) are the same as those exemplified in the description of the general formula (1D). The polymer charge transport material used in the present invention does not necessarily have a high molecular weight and may be a so-called oligomer. Therefore, it is preferable that the weight average molecular weight of the high molecular weight charge transporting material is 1000 or more, and particularly 2000 to
2,000,000 is preferable.

The azo pigments represented by the general formulas (1P) to (10P) used in the electrophotographic photoreceptor of the present invention will be described below.

Embedded image

(In the formula, Cp ₁ and Cp ₂ represent a coupler residue, which may be the same or different. R ′ ₁ ,
R _'2, R' ₃ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. )

[0060]

[Chemical 156] (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. )

[0061]

[Chemical 157] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .)

[0062]

[Chemical 158] (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.)

[0063]

[Chemical 159] (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue and may be the same or different. R ′ ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.)

[0064]

[Chemical 160] (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue, and may be the same or different. In addition, n represents an integer of 1 to 5.)

[0065]

[Chemical 161] (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.)

[0066]

[Chemical 162] (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.)

[0067]

[Chemical formula 163] (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. It may be the same or different.)

[0068]

Embedded image (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.)

In the above general formulas (1P) to (10P), the halogen atom is a chlorine atom, a bromine atom, etc., the alkyl group is a methyl group, an ethyl group, a propyl group, a butyl group, etc., and the alkoxy group is a methoxy group. , An ethoxy group, a propoxy group, a butoxy group, and the like, and an aryl group includes a phenyl group, a naphthyl group, and the like.
Examples of the coupler residues Cp _{1 to} Cp ₂₁ in the general formulas (1P) to (10P) include compounds having a phenolic hydroxyl group such as phenols and naphthols, aromatic amino compounds having an amino group, or amino. Aminonaphthols having a group and a phenolic hydroxyl group, compounds having an aliphatic or aromatic enol ketone group (compounds having an active methylene group), and the like are used, and the following general formulas (1) to (13) are preferable. What is represented is mentioned.

[0070]

Embedded image X, Y ₁ , Z, m or n in the general formula (1), (2), (3) or (4) represents the following. That, X _{is, -OH, -N (R 1)} (R 2) or -NH
SO ₂ —R ₃ , R ₁ and R ₂ represent a hydrogen atom or a substituted or unsubstituted alkyl group, and R ₃ represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. Y ₁ is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a carboxy group, a sulfone group, a substituted or unsubstituted sulfamoyl group, or —CON (R ₄ ) Y ₂ Represent R ₄ is a hydrogen atom, an alkyl group or a substitution product thereof, a phenyl group or a substitution product thereof, Y ₂ is a hydrocarbon ring group or a substitution product thereof, a heterocyclic group or a substitution product thereof, or -N = C (R ₅₎ Represents (R ₆ ). R ₅ represents a hydrocarbon ring group or a substituted product thereof, a heterocyclic group or a substituted product thereof, or a styryl group or a substituted product thereof, and R ₆ represents a hydrogen atom, an alkyl group, a phenyl group or a substituted product thereof. R ₅ and R ₆ may form a ring with the carbon atom attached to them. Z represents a hydrocarbon ring or a substituted product thereof, or a heterocycle or a substituted product thereof. m or n represents an integer of 1 or 2.

[0071]

[Chemical 166] [In the formula (5), R ₇ represents a substituted or unsubstituted hydrocarbon group, and X represents the same group as described above. ]

[0072]

[Chemical 167] [In formula (6), A represents a divalent group of an aromatic hydrocarbon or a divalent group of a heterocycle containing a nitrogen atom in the ring, and these rings may have a substituent. X represents the same group as above. ]

[0073]

[Chemical 168] [In the formula (7), R ₈ represents an alkyl group, a carbamoyl group, a benzyl group or an ester thereof, and Ar ₁ represents a hydrocarbon ring group or a substituted product thereof. X represents the same group as above. ]

[0074]

[Chemical 169] [In the formula (8) or (9), R ₉ represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group, and Ar ₂ represents a hydrocarbon ring group or a substituted product thereof. X represents the same group as above. ]

As the hydrocarbon ring of Z in the above general formula (1), (2), (3) or (4), a benzene ring, a naphthalene ring and the like can be exemplified, and a heterocycle (even if it has a substituent) Examples of (good) include an indole ring, a carbazole ring, a benzofuran ring and a dibenzofuran ring. Examples of the substituent in the ring of Z include a halogen atom such as a chlorine atom and a bromine atom. The hydrocarbon ring group for Y ₂ or R ₅ is a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group or the like, and the heterocyclic group is a pyridyl group, a thienyl group, a furyl group, an indolyl group,
Examples thereof include a benzofuranyl group, a carbazolyl group, and a dibezofuranyl group. Further, examples of the ring formed by combining R ₅ and R ₆ include a fluorene ring. Y ₂
Or hydrocarbon ring group or a heterocyclic group or a substituent in ring formed by R ₅ and R ₆ in R _5, a methyl group, an ethyl group, a propyl group, an alkyl group such as butyl group, a methoxy group, an ethoxy group , Propoxy group,
Alkoxy group such as butoxy group, halogen atom such as chlorine atom, bromine atom, dialkylamino group such as dimethylamino group, diethylamino group, halomethyl group such as trifluoromethyl group, nitro group, cyano group, carboxyl group or ester thereof, Examples thereof include a hydroxyl group and a sulfonate group such as —SO ₃ Na. Examples of the substituent on the phenyl group of R ₄ include a halogen atom such as a chlorine atom or a bromine atom. Representative examples of the hydrocarbon group for R ₇ or R ₉ include alkyl groups such as methyl group, ethyl group, propyl group and butyl group, aryl groups such as phenyl group, and substituted products thereof. The substituent in the hydrocarbon group of R ₇ or R ₉ is a methyl group,
Examples thereof include alkyl groups such as ethyl group, propyl group and butyl group, alkoxy groups such as methoxy group, ethoxy group, propoxy group and butoxy group, halogen atoms such as chlorine atom and bromine atom, hydroxyl group and nitro group.

Typical examples of the hydrocarbon ring group in Ar ₁ or Ar ₂ include phenyl group and naphthyl group, and the substituents in these groups include methyl group, ethyl group, propyl group and butyl group. Groups such as alkyl groups, methoxy groups, ethoxy groups, propoxy groups, butoxy groups, and other alkoxy groups, nitro groups, halogen atoms such as chlorine and bromine atoms, cyano groups, dialkylamino groups such as dimethylamino and diethylamino groups, etc. Can be illustrated. Further, in X, a hydroxyl group is particularly suitable. Among the above-mentioned coupler residues, the above-mentioned general formulas (2), (5), (6), (7), (8) and (9) are preferable.
Wherein X in the general formula is a hydroxyl group. Of these, a coupler residue represented by the following general formula (10) is preferable, and a coupler residue represented by the following general formula (11) is more preferable.

[0077]

Embedded image [In the formula (10), Y ₁ and Z are the same as defined above. ]

[0078]

[Chemical 171] [In the formula (11), Z, Y ₂ and R ₂ are the same as defined above. Furthermore, among the above-mentioned preferred coupler residues, a coupler residue represented by the following general formula (12) or (13) is particularly preferable.

[0079]

Embedded image [In formulas (12) and (13), Z, R ₂ , R ₅ and R ₆ are the same as defined above, and examples of R ₁₀ include the substituents of Y ₂ described above. ]

Specific examples of the coupler residue are shown in Tables 1 to 20.

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

[Table 13]

[Table 14]

[Table 15]

[Table 16]

[Table 17]

[Table 18]

[Table 19]

[Table 20]

Next, the structure of the electrophotographic photosensitive member of the present invention will be described with reference to the drawings. FIG. 1 is a sectional view schematically showing an example of the electrophotographic photosensitive member of the present invention, in which a photosensitive layer 2 is formed on a conductive support 1. FIG. 2 is a cross-sectional view schematically showing an electrophotographic photosensitive member having another structure. A photosensitive layer 2 in which a charge generation layer 21 and a charge transport layer 22 are laminated in this order on a conductive support 1 is formed. ing. FIG. 3 is a cross-sectional view schematically showing an electrophotographic photosensitive member having another structure, in which the charge transport layer 22 and the charge generating layer 2 are provided on the conductive support 1.
A photosensitive layer 2 is formed by laminating 1 in this order. FIG.
FIG. 3 is a cross-sectional view schematically showing an electrophotographic photosensitive member having another configuration, in which an intermediate layer 3 is provided between the conductive support 1 and the photosensitive layer 2.

The conductive support has a volume resistance of 1 × 10.
Materials with a conductivity of ¹⁰ Ωcm or less, such as metals such as aluminum, nickel, chromium, copper, silver, gold and platinum,
Metal or metal oxides such as tin oxide and indium oxide coated on film or cylindrical plastic or paper by vapor deposition or sputtering, or plates of aluminum, aluminum alloy, nickel, stainless steel, etc. I. , I. I. For example, it is possible to use a tube which is formed into a tube by a method such as extrusion, drawing, or the like, and then surface-treated by cutting, superfinishing, polishing, or the like. As the photosensitive layer, the above general formulas (1D) to (10)
A photosensitive layer having a single-layer structure containing at least one kind of the polymer charge transporting material represented by D) and at least one kind of the azo pigments represented by the general formulas (1P) to (10P), or the general formula A charge generation layer containing at least one kind of azo pigments represented by (1P) to (10P) and at least one kind of polymer charge transport material represented by the above general formulas (1D) to (10D). It may be any of photosensitive layers having a laminated structure in which charge transport layers are laminated.

An example having a laminated photosensitive layer will be described below. The charge generation layer is a layer containing at least one of the azo pigments represented by the general formulas (1P) to (10P) as a main component, and a binder resin is used if necessary. The azo pigments represented by the general formulas (1P) to (10P) can be used alone or as a mixture of two or more kinds. As the binder resin used in the charge generation layer, polyamide, polyurethane, epoxy resin, polyketone, polycarbonate, silicone resin, acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, poly-N-vinylcarbazole, polyacrylamide, etc. Is mentioned. These binder resins can be used alone or as a mixture of two or more kinds. Further, as the binder resin for the charge generation layer, a polymer charge transport material can be used in addition to the above binder resin. As the polymer charge-transporting substance, the polymer charge-transporting substances represented by the above general formulas (1D) to (10D) are also preferably used, but other polymer charge-transporting substances include the following.

(A) A polymer having a carbazole ring in its main chain and / or side chain, for example, poly-N-vinylcarbazole, JP-A-50-82056 and JP-A-54.
The compounds described in JP-A-9632, JP-A-54-11737 and JP-A-4-183719 can be exemplified. (B) Polymers having a hydrazone structure in the main chain and / or side chain, for example, compounds described in JP-A-57-78402 and JP-A-3-50555 can be exemplified. (C) Polysilylene polymer, for example, JP-A-63-28
Examples include the compounds described in JP-A-5552, JP-A-5-19497, and JP-A-5-70595. (D) A polymer having a tertiary amine structure in the main chain and / or side chain, for example, N, N-bis (4-methylphenyl) -4-aminopolystyrene, JP-A-1-13061
JP, JP-A-1-19049, JP-A-1-17
No. 28, JP-A-1-105260, JP-A-2
JP-167335, JP-A-5-66598,
Examples thereof include the compounds described in JP-A-5-40350. (E) Other polymers, for example, formaldehyde condensation polymer of nitropyrene, JP-A-51-73888,
Examples thereof include compounds described in JP-A-56-150749.

Further, in addition to the above polymers, copolymers of known monomers as polymers having an electron donating group,
It is also possible to use a block polymer, a graft polymer, a star polymer, or a cross-linked polymer having an electron donating group as disclosed in JP-A-3-109406.

The method for forming the charge generating layer is roughly classified into a vacuum thin film forming method and a casting method from a solution dispersion system. In the vacuum thin film production method, a vacuum vapor deposition method, a glow discharge decomposition method, an ion plating method, a sputtering method, a reactive sputtering method, a CVD method or the like is used, and at least one of the above-mentioned azo pigments is used as a main component by these methods. The charge generation layer can be formed well. Further, in order to form the charge generation layer by the casting method, at least one kind of the above-mentioned azo pigment is optionally used together with a binder resin in tetrahydrofuran, cyclohexanone, dioxane, dichloroethane,
Ball mill, attritor, using solvent such as butanone
It may be dispersed by a sand mill or the like, and the dispersion may be appropriately diluted, applied, and dried. As a coating method, a dip coating method, a spray coating method, a bead coating method, or the like can be used. The film thickness of the charge generation layer thus formed is preferably about 0.01 to 5 μm, particularly 0.0
5 to 2 μm is preferred.

Next, the charge transport layer will be described. The charge transport layer is a layer containing at least one polymer charge transport material represented by the general formulas (1D) to (10D) as a main component. It may be dissolved or dispersed in an appropriate solvent, applied and dried. Further, if necessary, an appropriate binder resin, low molecular weight charge transport material, plasticizer or leveling agent may be added.

As the binder resin that can be used in combination with the charge transport layer, polycarbonate (bisphenol A type,
Bisphenol Z type), polyester, methacrylic resin, acrylic resin, polyethylene, vinyl chloride, vinyl acetate, polystyrene, phenol resin, epoxy resin, polyurethane, polyvinylidene chloride, alkyd resin, silicone resin, polyvinyl carbazole, polyvinyl butyral , Polyvinyl formal, polyacrylate, polyacrylamide, phenoxy resin and the like. These binder resins can be used alone or as a mixture of two or more kinds. The amount of the binder resin used is appropriately 0 to 150 parts by weight based on 100 parts by weight of the polymer charge transport material. The low molecular weight charge transport materials that can be used in combination with the charge transport layer include hole transport materials and electron transport materials.

Examples of the electron transport substance include chloranil, bromanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone. , 2,4,5,7-tetranitroxanthone,
2,4,8-trinitrothioxanthone, 2,6,8-
Examples thereof include electron-accepting substances such as trinitro-4H-indeno [1,2-b] thiophen-4one and 1,3,7-trinitrodibenzothiophene-5,5-dioxide. These electron transport materials can be used alone or as a mixture of two or more kinds.

Further, examples of the hole-transporting substance include the electron-donating substances shown below, which are favorably used. That is, oxazole derivative, oxadiazole derivative, imidazole derivative, triphenylamine derivative, 9- (p-diethylaminostyrylanthracene), 1,1-bis- (4-dibenzylaminophenyl) propane, styrylanthracene, styrylpyrazoline , Phenylhydrazones, α-phenylstilbene derivatives, thiazole derivatives, triazole derivatives, phenazine derivatives, acridine derivatives, benzofuran derivatives, benzimidazole derivatives, thiophene derivatives and the like. These hole transport materials may be used alone or
It can be used as a mixture of more than one species.

As the plasticizer which may be added to the charge transport layer, those which are used as plasticizers for general resins such as dibutyl phthalate and dioctyl phthalate can be used as they are, and the amount thereof used is 100
About 0 to 30 parts by weight is suitable with respect to parts by weight. As the leveling agent, silicone oils such as dimethyl silicone oil and methylphenyl silicone oil, and polymers or oligomers having a perfluoroalkyl group in the side chain are used, and the amount used is 0 with respect to 100 parts by weight of the binder resin. About 1 part by weight is suitable. The appropriate thickness of the charge transport layer is about 5 to 100 μm.

To form a photosensitive layer having a single-layer structure, at least one of the azo pigments represented by the general formulas (1P) to (10P) and the general formulas (1D) to (10D) are represented. At least one polymer charge transporting material is dispersed with a binder resin, if necessary, using a solvent such as tetrahydrofuran, cyclohexanone, dioxane, dichloroethane, butanone by a ball mill, attritor, sand mill, etc., and the dispersion liquid is appropriately diluted. Then, it can be applied and dried. As a coating method, a dip coating method, a spray coating method, a bead coating method, or the like can be used. If necessary, a low-molecular-weight charge transport substance, a plasticizer, a leveling agent, or the like can be added to the single-layer photosensitive layer.

The intermediate layer between the conductive support and the photosensitive layer is provided for the purpose of improving the adhesion between the conductive support and the photosensitive layer, and the material thereof is SiO ₂ , Al ₂ O ₃ Inorganic materials such as silane coupling agent, titanium coupling agent, and chromium coupling agent, or resins with good adhesiveness such as polyamide resin, alcohol-soluble polyamide resin, water-soluble polyvinyl butyral, polyvinyl butyral, and PVA are used. . In addition, it is also possible to use a resin in which ZnO, TiO ₂ , ZnS, or the like is dispersed in the resin having good adhesiveness. As a method for forming the intermediate layer, a method such as sputtering or vapor deposition is used when the inorganic material is used alone, and a usual coating method is used when the organic material is used. The thickness of the intermediate layer is suitably 5 μm or less.

Further, the electrophotographic photosensitive member according to the present invention has a single-layer photosensitive layer, a charge generating layer, a charge transporting layer for the purpose of improving environmental resistance, particularly for the purpose of preventing lowering of sensitivity and increase of residual potential. An antioxidant can be added to the layer or the intermediate layer. In particular, by adding an antioxidant to the layer containing the charge transport material, it is possible to better prevent a decrease in sensitivity and an increase in residual potential.

Examples of the antioxidant include 2,6-di-t-butyl-p-cresol, butylated hydroxyanisole, 2,6-di-t-butyl-4-ethylphenol, stearyl-β- (. 3,5-di-t-butyl-4
Monophenolic compounds such as -hydroxyphenyl) propionate, 2,2'-methylene-bis- (4-methyl-6-t-butylphenol), 2,2'-methylene-bis- (4-ethyl-6-t -Butylphenol), 4,4'-thiobis- (3-methyl-6-t-butylphenol), 4,4'-butylidenebis- (3-butylphenol)
Bisphenol compounds such as methyl-6-t-butylphenol) and 1,1,3-tris- (2-methyl-4)
-Hydroxy-5-t-butylphenyl) butane, 1,
3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxybenzyl) benzene, tetrakis- [methylene-3- (3 ', 5'-di-t-butyl) -4'-hydroxyphenyl) propionate] methane, bis [3,3'-bis (4'-hydroxy-3 '
-T-butylphenyl) butyric acid] glycol esters, high molecular weight phenolic compounds such as tocopherols, N-phenyl-N'-isopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p
-Phenylenediamine, N-phenyl-N-sec-butyl-p-phenylenediamine, N, N'-di-isopropyl-p-phenylenediamine, N, N'-dimethyl-N, N'-di-t-butyl Para-phenylenediamines such as -p-phenylenediamine, 2,5-di-t-octylhydroquinone, 2,6-didodecylhydroquinone, 2-dodecylhydroquinone, 2-dodecyl-5
-Chlorohydroquinone, 2-t-octyl-5-methylhydroquinone, 2- (2-octadecenyl) -5-
Hydroquinones such as methylhydroquinone, dilauryl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, ditetradecyl-
Organic sulfur compounds such as 3,3'-thiodipropionate, triphenylphosphine, tri (nonylphenyl)
Organic phosphorus compounds such as phosphine, tri (dinonylphenyl) phosphine, tricresylphosphine, and tri (2,4-dibutylphenoxy) phosphine.
These compounds are known as antioxidants for rubbers, plastics, oils and the like, and can be easily obtained as commercial products.

The amount of the antioxidant added is preferably 0.1 to 100 parts by weight, more preferably 2 to 30 parts by weight, based on 100 parts by weight of the charge transport material.

[0097]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited thereto. In addition, the part used in an Example represents a weight part unless there is particular notice.

Example 1-1 On a polyethylene terephthalate film on which aluminum was vapor-deposited, a charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially coated and dried to give a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

[Chemical 173] Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Example 1-2 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that the charge-generating substance having the following structural formula was used instead of the charge-generating substance in Example 1-1.

Embedded image

Example 1-3 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that the charge-generating substance having the following structural formula was used instead of the charge-generating substance in Example 1-1.

[Chemical 176]

Example 1-4 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that the charge generating substance in Example 1-1 was replaced by the charge generating substance having the following structural formula.

[Chemical 177]

Example 1-5 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that the charge generating substance in Example 1-1 was replaced by the charge generating substance having the following structural formula.

[Chemical 178]

Example 1-6 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that the charge generating substance in Example 1-1 was replaced with the charge generating substance having the following structural formula.

[Chemical 179]

Example 1-7 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that the charge generating substance in Example 1-1 was replaced by the charge generating substance having the following structural formula.

[Chemical 180]

Example 1-8 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that the charge generating substance in Example 1-1 was replaced by the charge generating substance having the following structural formula.

[Chemical 181]

Example 1-9 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that the charge generating substance in Example 1-1 was replaced with the charge generating substance having the following structural formula.

[Chemical 182]

Comparative Example 1-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-1, except that copper phthalocyanine was used instead of the charge generating substance in Example 1-1.

Example 1-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transporting layer coating solution having the following compositions were sequentially coated and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

[Chemical 183] Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Example 1-11 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10, except that the charge generating substance in Example 1-10 was replaced with the charge generating substance represented by the following structural formula.

[Chemical 185]

Example 1-12 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10, except that the charge generating substance in Example 1-10 was replaced with the charge generating substance having the following structural formula.

[Chemical 186]

Example 1-13 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10, except that the charge generating substance in Example 1-10 was replaced with the charge generating substance represented by the following structural formula.

[Chemical 187]

Example 1-14 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10 except that the charge generating substance in Example 1-10 was replaced with the charge generating substance having the following structural formula.

[Chemical 188]

Example 1-15 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10, except that the charge-generating substance having the following structural formula was used instead of the charge-generating substance in Example 1-10.

[Chemical 189]

Example 1-16 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10, except that the charge-generating substance having the following structural formula was used instead of the charge-generating substance in Example 1-10.

Embedded image

Example 1-17 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10, except that the charge generating substance in Example 1-10 was replaced with the charge generating substance having the following structural formula.

[Chemical 191]

Example 1-18 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10, except that the charge generating substance in Example 1-10 was replaced with the charge generating substance represented by the following structural formula.

[Chemical 192]

Comparative Example 1-2 An electrophotographic photosensitive member was prepared in the same manner as in Example 1-10, except that the charge generating layer coating liquid in Example 1-10 was replaced with the charge generating layer coating liquid having the following composition. did. [Charge generating layer coating liquid] 1 part of the charge generating substance having the following structural formula

[Chemical formula 193] Tetrahydrofuran 100 parts

Example 2-1 On a polyethylene terephthalate film on which aluminum was vapor-deposited, a charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially applied and dried to give a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

[Chemical 195] 100 parts of methylene chloride

Examples 2-2 to 2-9 Example 1-in place of the charge generating substance in Example 2-1
Example 2 except that the charge generating substances 2 to 1-9 were used.
In the same manner as in Example 1, electrophotographic photosensitive members of Examples 2-2 to 2-9 were prepared.

Comparative Example 2-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 2-1 except that copper phthalocyanine was used instead of the charge generating substance in Example 2-1.

Example 2-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transporting layer coating solution having the following compositions were sequentially coated and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

[Chemical 196] Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

[Chemical 197] 150 parts of toluene

Examples 2-11 to 2-18 Example 1 in place of the charge generating substance in Example 2-10
Electrophotographic photoreceptors of Examples 2-11 to 2-18 were prepared in the same manner as in Example 2-10 except that each of the charge generating substances of -11 to 1-18 was used.

Comparative Example 2-2 The charge generation layer coating liquid in Example 2-10 was used in Comparative Example 1-
An electrophotographic photoreceptor was prepared in the same manner as in Example 2-10, except that the coating liquid for charge generation layer No. 2 was used instead.

Example 3-1 A polyethylene terephthalate film on which aluminum was vapor-deposited, a charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially applied and dried to give a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

[Chemical formula 199] 100 parts of methylene chloride

Examples 3-2 to 3-9 Example 1-in place of the charge generating substance in Example 3-1
Example 3 except that each of the charge generating substances 2 to 1-9 was used.
In the same manner as in Example 1, electrophotographic photosensitive members of Examples 3-2 to 3-9 were prepared.

Comparative Example 3-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 3-1, except that copper phthalocyanine was used instead of the charge generating substance in Example 3-1.

Example 3-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

Embedded image Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Examples 3-11 to 3-18 Example 1 instead of the charge generating substance in Example 3-10
Electrophotographic photoreceptors of Examples 3-11 to 3-18 were prepared in the same manner as in Example 3-10 except that each of the charge generating substances of -11 to 1-18 was used.

Comparative Example 3-2 The charge generation layer coating liquid of Example 3-10 was used in Comparative Example 1-
An electrophotographic photoreceptor was prepared in the same manner as in Example 3-10, except that the coating liquid for charge generation layer No. 2 was used instead.

Example 4-1 A charge generating layer coating liquid and a charge transporting layer coating liquid having the following compositions were sequentially applied on a polyethylene terephthalate film on which aluminum was vapor-deposited, and dried to give a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Examples 4-2 to 4-9 Example 1-in place of the charge generating substance in Example 4-1
Example 4-except that the charge generating substances 2 to 1-9 were used.
In the same manner as in Example 1, electrophotographic photosensitive members of Examples 4-2 to 4-9 were prepared.

Comparative Example 4-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 4-1, except that copper phthalocyanine was used instead of the charge generating substance in Example 4-1.

Example 4-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution, and a charge transport layer coating solution having the following compositions were sequentially coated and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

Embedded image Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Examples 4-11 to 4-18 Example 1 is used instead of the charge generating substance in Example 4-10.
Electrophotographic photoreceptors of Examples 4-11 to 4-18 were prepared in the same manner as in Example 4-10 except that the charge generating substances of -11 to 1-18 were used.

Comparative Example 4-2 The charge generation layer coating liquid in Example 4-10 was used in Comparative Example 1-
An electrophotographic photosensitive member was prepared in the same manner as in Example 4-10 except that the coating liquid for charge generating layer No. 2 was used instead.

Example 5-1 A polyethylene terephthalate film vapor-deposited with aluminum was sequentially coated with a coating solution for the charge generation layer and a coating solution for the charge transport layer having the following compositions and dried to obtain a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Examples 5-2 to 5-9 Example 1-in place of the charge generating substance in Example 5-1
Example 5 except that each of the charge generating substances 2 to 1-9 was used
Electrophotographic photoreceptors of Examples 5-2 to 5-9 were prepared in the same manner as in Example 1.

Comparative Example 5-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 5-1 except that copper phthalocyanine was used instead of the charge generating substance in Example 5-1.

Example 5-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

Embedded image Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Examples 5-11 to 5-18 Example 1 in place of the charge generating substance in Example 5-10
Electrophotographic photoreceptors of Examples 5-11 to 5-18 were prepared in the same manner as in Example 5-10 except that each of the charge generating substances of -11 to 1-18 was used.

Comparative Example 5-2 The charge generation layer coating liquid in Example 5-10 was used in Comparative Example 1-
An electrophotographic photosensitive member was prepared in the same manner as in Example 5-10, except that the coating liquid for charge generation layer 2 was used instead.

Example 6-1 A polyethylene terephthalate film vapor-deposited with aluminum was sequentially coated with a coating solution for a charge generation layer and a coating solution for a charge transport layer having the following compositions and dried to give a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Examples 6-2 to 6-9 Example 1-in place of the charge generating substance in Example 6-1
Example 6-Aside from using the charge generating substances 2 to 1-9
Electrophotographic photoconductors of Examples 6-2 to 6-9 were prepared in the same manner as in Example 1.

Comparative Example 6-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 6-1 except that copper phthalocyanine was used instead of the charge generating substance in Example 6-1.

Example 6-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transporting layer coating solution having the following compositions were sequentially coated and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

Embedded image Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Examples 6-11 to 6-18 Example 1 instead of the charge generating substance in Example 6-10
Electrophotographic photoreceptors of Examples 6-11 to 6-18 were prepared in the same manner as in Example 6-10 except that the charge generating substances of -11 to 1-18 were used.

Comparative Example 6-2 The charge generation layer coating liquid in Example 6-10 was used in Comparative Example 1-
An electrophotographic photosensitive member was prepared in the same manner as in Example 6-10 except that the coating liquid for charge generating layer 2 was used instead.

Example 7-1 On a polyethylene terephthalate film vapor-deposited with aluminum, a charge generation layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied and dried to give a charge of 0.3 μm in thickness. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Examples 7-2 to 7-9 Example 1-instead of the charge generating material in Example 7-1
Example 7-Aside from using the charge generating substances 2 to 1-9.
Electrophotographic photoreceptors of Examples 7-2 to 7-9 were prepared in the same manner as in Example 1.

Comparative Example 7-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 7-1 except that copper phthalocyanine was used instead of the charge generating substance in Example 7-1.

Example 7-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transporting layer coating solution having the following compositions were sequentially applied and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

Embedded image Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Examples 7-11 to 7-18 Example 1 is used in place of the charge generating substance in Example 7-10.
Electrophotographic photoreceptors of Examples 7-11 to 7-18 were prepared in the same manner as in Example 7-10 except that each of the charge generating substances of -11 to 1-18 was used.

Comparative Example 7-2 The charge generation layer coating liquid of Example 7-10 was used in Comparative Example 1-
An electrophotographic photosensitive member was prepared in the same manner as in Example 7-10 except that the coating liquid for charge generating layer No. 2 was used instead.

Example 8-1 On a polyethylene terephthalate film on which aluminum was vapor-deposited, a charge generation layer coating liquid and a charge transport layer coating liquid having the following compositions were sequentially applied and dried to give a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Examples 8-2 to 8-9 Example 1-in place of the charge generating substance in Example 8-1
Example 8-Aside from using the charge generating substances 2 to 1-9
Electrophotographic photoreceptors of Examples 8-2 to 8-9 were prepared in the same manner as in Example 1.

Comparative Example 8-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 8-1, except that copper phthalocyanine was used instead of the charge generating substance in Example 8-1.

Example 8-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

Embedded image Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Examples 8-11 to 8-18 Example 1 is used instead of the charge generating substance in Example 8-10.
Electrophotographic photoreceptors of Examples 8-11 to 8-18 were prepared in the same manner as in Example 8-10 except that each of the charge generating substances of -11 to 1-18 was used.

Comparative Example 8-2 The charge generation layer coating liquid of Example 8-10 was used in Comparative Example 1-
An electrophotographic photoreceptor was prepared in the same manner as in Example 8-10 except that the coating liquid for charge generating layer No. 2 was used instead.

Example 9-1 A polyethylene terephthalate film vapor-deposited with aluminum was sequentially coated with a coating solution for a charge generation layer and a coating solution for a charge transport layer having the following compositions and dried to obtain a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Examples 9-2 to 9-9 Example 1-instead of the charge generating substance in Example 9-1
Example 9-Aside from using the charge generating substances 2 to 1-9
Electrophotographic photoreceptors of Examples 9-2 to 9-9 were prepared in the same manner as in Example 1.

Comparative Example 9-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 9-1 except that copper phthalocyanine was used instead of the charge generating substance in Example 9-1.

Example 9-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

Embedded image Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Examples 9-11 to 9-18 Example 1 is used instead of the charge generating substance in Examples 9-10.
Electrophotographic photoreceptors of Examples 9-11 to 9-18 were prepared in the same manner as in Example 9-10 except that each of the charge generating substances of -11 to 1-18 was used.

Comparative Example 9-2 The charge generation layer coating solution of Example 9-10 was used in Comparative Example 1-
An electrophotographic photoreceptor was prepared in the same manner as in Example 9-10, except that the coating liquid for charge generation layer No. 2 was used instead.

Example 10-1 A polyethylene terephthalate film vapor-deposited with aluminum was successively coated with a coating solution for a charge generation layer and a coating solution for a charge transport layer having the following compositions, and the coating solution was dried to give a charge having a thickness of 0.3 μm. A generation layer and a charge transport layer having a thickness of 20 μm were formed to prepare an electrophotographic photoreceptor. [Charge generating layer coating liquid] 5 parts of the charge generating substance having the following structural formula

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Examples 10-2 to 10-9 Example 1 is replaced with the charge generating substance in Example 10-1.
Example 1 except that each of the charge generating substances of −2 to 1-9 was used
Electrophotographic photoreceptors of Examples 10-2 to 10-9 were prepared in the same manner as in 0-1.

Comparative Example 10-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 10-1 except that copper phthalocyanine was used instead of the charge generating substance in Example 10-1.

Example 10-10 On a polyethylene terephthalate film provided with a Hastelloy conductive layer, an intermediate layer coating solution, a charge generating layer coating solution and a charge transport layer coating solution having the following compositions were sequentially applied and dried. Then, an intermediate layer having a thickness of 0.3 μm, a charge generating layer having a thickness of 0.2 μm, and a charge transporting layer having a thickness of 22 μm were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM4000, manufactured by Toray) 3 parts Methanol 60 parts Butanol 40 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 4 parts

Embedded image Polysulfone (P-1700, manufactured by Nissan Kagaku Co., Ltd.) 1 part Cyclohexanone 300 parts [Charge Transport Layer Coating Liquid] Polymer charge transport material of the following structural formula 7 parts

Embedded image 150 parts of toluene

Examples 10-11 to 10-18 The same as Examples 10-10 except that the charge generating substances of Examples 10-10 were replaced with the charge generating substances of Examples 1-11 to 1-18. Example 10-11 to 10-
18 electrophotographic photoconductors were prepared.

Comparative Example 10-2 The charge generation layer coating liquid in Example 10-10 was used in Comparative Example 1
Example 10-1 except that the charge generation layer coating solution of Example 2 was used instead.
An electrophotographic photosensitive member was prepared in the same manner as in No. 0.

The electrophotographic photoreceptors of Examples and Comparative Examples prepared as described above were subjected to the following procedure using an electrostatic copying paper test apparatus (Kawaguchi Denki Seisakusho, SP-428 type) as follows. The characteristics were evaluated. That is, first -6K
Corona discharge is performed for 20 seconds by a discharge voltage of V, and then dark decay is performed, and when the surface potential becomes −800 V, 6 lux of tungsten light is irradiated, and the surface potential becomes −2.
Exposure amount E200 (lux.se
c), and the potential V30 after 30 seconds of irradiation with tungsten light
(V) was measured. The results are shown in Tables 21 to 30.

[0173]

[Table 21]

[Table 22]

[Table 23]

[Table 24]

[Table 25]

[Table 26]

[Table 27]

[Table 28]

[Table 29]

[Table 30] As is clear from Tables 21 to 30, the electrophotographic photosensitive members of the examples have higher sensitivity and lower residual potential than the electrophotographic photosensitive members of the comparative example.

Example 11-1 On an aluminum drum having a diameter of 80 mm, an intermediate layer coating solution, a charge generating layer coating solution and a charge transport layer coating solution having the following compositions were sequentially coated and dried to a thickness of 0. A 0.3 μm intermediate layer, a 0.2 μm charge generation layer, and a 20 μm charge transport layer were formed to prepare an electrophotographic photoreceptor. [Intermediate layer coating liquid] Alcohol-soluble nylon (Alamine CM8000, manufactured by Toray) 3 parts Titanium oxide 0.5 part Methanol 70 parts Butanol 30 parts [Charge generating layer coating liquid] Charge generating substance of the following structural formula 5 parts

Embedded image Phenoxy resin (VYHH, Union Carbide Co., Ltd.) 1 part Tetrahydrofuran 400 parts [Charge transport layer coating liquid] Polymer charge transport substance of the following structural formula 6 parts

Embedded image 100 parts of methylene chloride

Example 11-2 Example 1-2 except that the polymer charge transporting material of the following structural formula was used in place of the polymer charge transporting material in Example 11-1.
An electrophotographic photosensitive member was prepared in the same manner as in 1-1.

Embedded image

Comparative Example 11-1 An electrophotographic photosensitive member was prepared in the same manner as in Example 11-1 except that the following charge transport layer coating liquid was used in place of the charge transport layer coating liquid in Example 11-1. Created. [Coating liquid for charge transport layer] 10 parts of low molecular weight charge transport material having the following structural formula

Embedded image Z-type polycarbonate (viscosity average molecular weight of about 40,000) 10 parts Methylene chloride 130 parts The electrophotographic photoreceptors of Examples 11-1 and 11-2 and Comparative Example 11-1 were mounted on a copying machine (Recopy FT3300, manufactured by Ricoh Company). Then, a running test of 70,000 sheets was performed, the images of the first and 70,000 sheets were visually evaluated, and the reduction amount (wear amount) of the thickness of the charge transport layer after the running test of 70,000 sheets was measured. I went. The results are shown in Table 31.

[0177]

[Table 31]

[0178]

INDUSTRIAL APPLICABILITY According to the present invention, in an electrophotographic photosensitive member having a photosensitive layer provided on a conductive support, the polymer charge transport represented by the above general formulas (1D) to (10D) is applied to the photosensitive layer. By containing at least one of the substances and at least one of the azo pigments represented by the general formulas (1P) to (10P), the film forming property of the photosensitive layer is good, and the abrasion resistance during repeated use is improved. It is possible to obtain an electrophotographic photosensitive member which is excellent in sensitivity, has high sensitivity, and has a small residual potential. Further, according to the present invention, the charge generation layer containing at least one kind of the azo pigments represented by the general formulas (1P) to (10P) and the high amount represented by the general formulas (1D) to (10D). By laminating a charge transporting layer containing at least one kind of molecular charge transporting substance to form a photosensitive layer, an electrophotographic photoreceptor having excellent abrasion resistance during repeated use, high sensitivity and low residual potential is obtained. be able to.

[Brief description of drawings]

FIG. 1 is a cross-sectional view schematically showing one example of an electrophotographic photoreceptor of the present invention.

FIG. 2 is a sectional view schematically showing another example of the electrophotographic photosensitive member of the present invention.

FIG. 3 is a sectional view schematically showing another example of the electrophotographic photosensitive member of the present invention.

FIG. 4 is a sectional view schematically showing still another example of the electrophotographic photosensitive member of the present invention.

[Explanation of symbols]

 1 Conductive Support 2 Photosensitive Layer 21 Charge Generation Layer 22 Charge Transport Layer 3 Intermediate Layer

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Koji Kishida 1-3-6 Nakamagome, Ota-ku, Tokyo Within Ricoh Co., Ltd. (72) Inventor, Eiichi Paper 1-3-6 Nakamagome, Ota-ku, Tokyo Shares Company Ricoh

Claims (11)

[Claims] 1. An electrophotographic photosensitive member comprising a photosensitive layer provided on a conductive support, wherein the photosensitive layer is at least one kind of polymer charge transporting substance represented by the following general formula (1D) and the following general formula (1D). An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image {In the formula, R ″ ₁ , R ″ ₂ and R ″ ₃ each independently represent a substituted or unsubstituted alkyl group or a halogen atom, and R ″ ₄ represents a hydrogen atom or a substituted or unsubstituted alkyl group. . R ₁ and R ₂ represent a substituted or unsubstituted aryl group. o, p, and q each independently represent an integer of 0 to 4. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula (A). Embedded image [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O—, —CO—O—Z—O—CO— (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical 4] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) [Chemical 7] (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (Wherein, Cp _10, Cp ₁₁ represents a coupler residue, it may be the same or different. Also, R _'9 represents a hydrogen atom or a substituted or unsubstituted alkyl group.) Embedded image (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 2. An electrophotographic photosensitive member comprising a photosensitive layer provided on a conductive support, wherein the photosensitive layer is at least one kind of polymer charge transporting material represented by the following general formula (2D) and the following general formula (2 An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image In the formula, R ₃ and R ₄ represent a substituted or unsubstituted aryl group, and Ar ₁ , Ar ₂ and Ar ₃ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula (A). Embedded image [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O—, —CO—O—Z—O—CO— (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical 17] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) [Chemical 19] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue, which may be the same or different.) (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue and may be the same or different. Further, R ′ ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.) (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 3. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided thereon, wherein the photosensitive layer is at least one kind of polymer charge transporting material represented by the following general formula (3D) and the following general formula An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image In the formula, R ₅ and R ₆ represent a substituted or unsubstituted aryl group, and Ar ₄ , Ar ₅ and Ar ₆ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula (A). Embedded image [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical formula 30] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue and may be the same or different. Further, R ′ ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.) (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 4. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided on the conductive support, wherein the photosensitive layer is at least one kind of polymer charge transporting material represented by the following general formula (4D) and the following general formula (4D). An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image In the formula, R ₇ and R _{8 each} represent a substituted or unsubstituted aryl group, and Ar ₇ , Ar ₈ , and Ar ₉ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. r represents an integer of 1 to 5. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula (A). Embedded image [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical 43] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) [Chemical 45] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (Wherein, Cp _10, Cp ₁₁ represents a coupler residue, it may be the same or different. Also, R _'9 represents a hydrogen atom or a substituted or unsubstituted alkyl group.) Embedded image (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 5. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided thereon, wherein the photosensitive layer is at least one polymer charge transporting material represented by the following general formula (5D) and the following general formula (5D). An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image In the formula, R ₉ and R ₁₀ represent a substituted or unsubstituted aryl group, and Ar ₁₀ , Ar ₁₁ , and Ar ₁₂ represent the same or different arylene groups. X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group.
k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9.
And n represents the number of repeating units and is an integer of 5 to 5000. X is an aliphatic divalent group, a cycloaliphatic divalent group,
Alternatively, it represents a divalent group represented by the following general formula (A). Embedded image [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical 56] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) [Chemical 58] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue and may be the same or different. Further, R ′ ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.) (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 6. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer formed thereon, wherein the photosensitive layer is at least one kind of polymeric charge transporting material represented by the following general formula (6D) and the following general formula (6D). An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image In the formula, R ₁₁ , R ₁₂ , R ₁₃ , and R ₁₄ represent a substituted or unsubstituted aryl group, and Ar ₁₃ , Ar ₁₄ , Ar ₁₅ , Ar ₁₆
Represents the same or different arylene groups. Y ₁ , Y ₂ , Y ₃
Represents a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, a sulfur atom or a vinylene group, which may be the same or different Good. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦
0.9, and n represents the number of repeating units, and is 5 to 500
It is an integer of 0. X is an aliphatic divalent group, a cycloaliphatic 2
A divalent group or a divalent group represented by the following general formula (A). Embedded image [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) [Chemical 71] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue, which may be the same or different. R ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.) (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 7. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided thereon, wherein the photosensitive layer is at least one kind of polymeric charge transporting material represented by the following general formula (7D) and the following general formula (7D). An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image 中 In the formula, R ₁₅ and R ₁₆ represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁₅ and R ₁₆ may form a ring. Ar ₁₇ , Ar ₁₈ and Ar ₁₉ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0
≦ j ≦ 0.9, n represents the number of repeating units, and
It is an integer of 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula (A). Embedded image [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical formula 82] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) [Chemical 84] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue and may be the same or different. Further, R ′ ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.) (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 8. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided thereon, wherein the photosensitive layer is at least one kind of polymeric charge transporting material represented by the following general formula (8D) and the following general formula (8D). An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image In the formula, R ₁₇ represents a substituted or unsubstituted aryl group, and Ar ₂₀ , Ar ₂₁ , Ar ₂₂ , and Ar ₂₃ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k
≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X is an aliphatic divalent group,
It represents a cyclic aliphatic divalent group or a divalent group represented by the following general formula (A). Embedded image [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical 95] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) [Chemical 97] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue and may be the same or different. Further, R ′ ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.) (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 9. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided thereon, wherein the photosensitive layer is at least one kind of polymeric charge transporting material represented by the following general formula (9D) and the following general formula (9D). An electrophotographic photoreceptor containing at least one kind of azo pigments represented by 1P) to (10P). Embedded image In the formula, R ₁₈ , R ₁₉ , R ₂₀ , and R ₂₁ represent a substituted or unsubstituted aryl group, and Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , A
r ₂₇ and Ar ₂₈ represent the same or different arylene groups.
k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9.
And n represents the number of repeating units and is an integer of 5 to 5000. X is an aliphatic divalent group, a cycloaliphatic divalent group,
Alternatively, it represents a divalent group represented by the following general formula (A). [Chemical formula 106] [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical 108] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) [Chemical 110] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue and may be the same or different. R ′ ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.) (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 10. An electrophotographic photoreceptor comprising a photosensitive layer provided on a conductive support, wherein the photosensitive layer has the following general formula (10):
An electrophotographic photoreceptor containing at least one kind of a polymer charge transporting material represented by D) and at least one kind of an azo pigment represented by the following general formulas (1P) to (10P). Embedded image In the formula, R ₂₂ and R ₂₃ represent a substituted or unsubstituted aryl group, and Ar ₂₉ , Ar ₃₀ , and Ar ₃₁ represent the same or different arylene groups. k and j represent compositions, and 0.1 ≦ k ≦
1, 0 ≦ j ≦ 0.9, and n represents the number of repeating units, and is an integer of 5 to 5000. X is an aliphatic divalent group,
It represents a cyclic aliphatic divalent group or a divalent group represented by the following general formula (A). [Chemical formula 119] [In the formula, R ₂₄ and R ₂₅ each independently represent a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represent an integer of 0 to 4. Y is a single bond, -C 1-12 linear, branched or cyclic alkylene group, -O -, - S -, - SO -, - SO 2 -, - C
O-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B): (Where a represents an integer of 1 to 20, b represents 1 to 2000
Represents the integer. R ₂₆ and R ₂₇ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. R ₂₄ and R ₂₅ ,
R ₂₆ and R ₂₇ may be the same or different. ]} [Chemical 121] (In the formula, Cp ₁ and Cp ₂ represent a coupler residue and may be the same or different. Further, R ′ ₁ , R ′ ₂ and R ′ ₃ are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or Represents a cyano group.) (In the formula, Cp ₃ , Cp ₄ , and Cp ₅ represent a coupler residue, which may be the same or different. R ′ ₄ ,
R _'5, R' ₆ represents a hydrogen atom, a halogen atom, an alkyl group,
Represents an alkoxy group or a cyano group. ) [Chemical 123] (In the formula, Cp ₆ and Cp ₇ represent a coupler residue and may be the same or different. R ′ ₇ and R ′ ₈ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a cyano group. .) (In the formula, Cp ₈ and Cp ₉ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₀ and Cp ₁₁ represent a coupler residue and may be the same or different. Further, R ′ ₉ represents a hydrogen atom or a substituted or unsubstituted alkyl group.) (In the formula, Cp ₁₂ and Cp ₁₃ represent a coupler residue and may be the same or different. In addition, n represents an integer of 1 to 5.) (In the formula, Cp ₁₄ and Cp ₁₅ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₆ and Cp ₁₇ represent a coupler residue and may be the same or different.) (In the formula, Cp ₁₈ and Cp ₁₉ represent a coupler residue and may be the same or different. A and B are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a substituted or unsubstituted aryl group. And may be the same or different.) (In the formula, Cp ₂₀ and Cp ₂₁ represent a coupler residue and may be the same or different. Ar ' ₁ and Ar' ₂ represent a substituted or unsubstituted biphenylyl group and may be the same or different. Ar ' ₃ represents a substituted or unsubstituted aryl group.) 11. The photosensitive layer comprises a laminate of a charge generation layer and a charge transport layer, and the charge generation layer is represented by the general formulas (1P) to (10).
P) and at least one azo pigment, and the charge transport layer contains at least one polymer charge transport material represented by the general formulas (1D) to (10D). The electrophotographic photosensitive member according to claim 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.