JPH09319114A - Electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an electrophotographic photoreceptor having high sensitivity and low residual potential, by interposing an electric changed injection layer based on a low molecular electric charge transferring material between an electric charge generating layer and a specified electric charge transferring layer. SOLUTION: An electric charge generating layer and an electric charge transferring layer contg. at least one kind of high molecular electric charge transferring material represented by the formula are laminated on an electrically conductive substrate, and an electric charge injection layer based on a low molecular electric charge transferring material is interposed between the laminated layers. In the formula, each of R1 -R3 is an optionally substd. alkyl or a halogen, R4 is H or an optionally substd. alkyl, each of R5 and R6 is an 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, a divalent alicyclic group, 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 used in copying machines, facsimiles, laser printers and the like. More specifically, it relates to a high-sensitivity electrophotographic photoreceptor having a photosensitive layer containing a polymer charge transport material.

[0002]

2. Description of the Related Art As the electrophotographic method, the Carlson process and various other deformation processes are known, and they are widely used in copying machines and printers. Among the photoconductors used in such electrophotography, those using organic photosensitive materials have been used in recent years because of their advantages such as low cost, mass productivity, and pollution-free property. The organic electrophotographic photoreceptor includes a photoconductive resin typified by polyvinylcarbazole (PVK), a charge transfer complex type typified by PVK-TNF (2,4,7-trinitrofluorenone), and phthalocyanine-. Pigment dispersion type typified by a binder, function-separated type photoconductor using a combination of a charge generating substance and a charge transport substance, and the like are known, and in particular, a function-separated type photoconductor is drawing attention.

The mechanism of electrostatic latent image formation in this function-separated type photoconductor is that, when the photoconductor is irradiated with light after being charged, the light passes through the transparent charge transport layer and is caused by the charge generating substance in the charge generating layer. Is absorbed, which generates charge carriers,
This charge carrier is injected into the charge transport layer, moves in the charge transport layer along the electric field generated by charging, and neutralizes the charge on the surface of the photoconductor to form an electrostatic latent image. In the function-separated type photoreceptor, it is known to be used in combination with 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 to the near-infrared region, and is useful. is there. Many low molecular weight compounds have been developed as charge transport materials, but since low molecular weight compounds alone do not provide a self-supporting film, they are usually used by being dispersed and mixed in an inert polymer.

However, for example, in the function-separated type laminated photoreceptor, the charge transport layer composed of a low molecular charge transport material and an inert polymer is generally soft, and in the Carlson process, there is a drawback that film abrasion is likely to occur due to repeated use. . Further, the charge transport layer having this structure has a limit in charge mobility, which has been an obstacle to speeding up or downsizing the Carlson process. This is because the content of the low molecular weight charge transport material is usually 100 parts by weight or less based on 100 parts by weight of the polymer component. That is, the charge mobility can certainly be increased by increasing the content of the low-molecular-weight charge transport material, but at the same time, the film-forming property is lowered.

In order to overcome these problems, attention has been paid to a polymer type charge transport material, for example, JP-A-50-8205.
6, JP-A-51-73888, JP-A-54.
-8527, JP 54-11737, JP 56-150749, and JP 57-7840.
No. 2, JP-A-63-285552, JP-A-1
It is disclosed in Japanese Patent Laid-Open No. 1728, Japanese Patent Laid-Open No. 3-50555, and the like. Although the abrasion resistance of the photosensitive layer is improved by these techniques, the photosensitivity of the photoconductor in which the charge transporting layer composed of these polymer charge transporting materials and the charge generating layer is combined is It is significantly inferior to the case where a transport material and an inert polymer material are used, and further, it is not satisfactory in terms of generation and accumulation of residual potential, and improvements in these points have been strongly desired.

[0006]

As described above, when the charge transport layer of the function-separated type laminated photoreceptor is formed of the low molecular charge transport material and the inert polymer material, the charge mobility, that is, the response speed is limited. In addition, there is a problem that the charge transport layer is scraped by repeated use. Further, when a polymer charge transport material is used alone in the charge transport layer, there is a fatal defect that the sensitivity of the photoreceptor is low. The present invention has been made in view of such circumstances, and an object of the present invention is to provide an electrophotographic photosensitive member having a high sensitivity and a small residual potential, which uses a polymer charge transport material.

[0007]

According to the present invention, a charge generating layer and at least one polymer charge transporting material represented by the following general formulas (1) to (10) are provided on a conductive support. Provided is an electrophotographic photosensitive member comprising a charge transport layer laminated, and a charge injection layer containing a low molecular charge transport material as a main component provided between the charge generation layer and the charge transport layer.

[0008]

Embedded image In the formula, R ₁ , R ₂ , and R ₃ are each independently a substituted or unsubstituted alkyl group or a halogen atom, R ₄ is a hydrogen atom, or a substituted or unsubstituted alkyl group, and R ₅ and R ₆ are substituted. Or an unsubstituted aryl group, o, p, and q are each independently an integer of 0 to 4, k and j represent the composition, 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 an aliphatic divalent group, a cyclic aliphatic divalent group, or a divalent group represented by the following general formula (1-1).

[0009]

Embedded image In the formula, R ₁₀₁ and R ₁₀₂ each independently represent a substituted or unsubstituted alkyl group, aryl group, or halogen atom.
l and m are integers of 0 to 4; Y is a single bond;
2, a linear, branched or cyclic alkylene group, -O
-, - S -, - SO -, - SO 2 -, - CO -, - CO
—O—Z—O—CO— (wherein Z represents an aliphatic divalent group) or a group represented by general formula (1-2) shown below.

[0010]

[Chemical formula 26] In the formula, a is an integer of 1 to 20, b is an integer of 1 to 2000,
R ₁₀₃ and R ₁₀₄ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. Where R ₁₀₁ and R ₁₀₂ ,
R ₁₀₃ and R ₁₀₄ may be the same or different.

[0011]

Embedded image In the formula, R ₇ and R ₈ are substituted or unsubstituted aryl groups, A
r ₁ , Ar ₂ and Ar ₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of the general formula (1).

[0012]

Embedded image In the formula, R ₉ and R ₁₀ are substituted or unsubstituted aryl groups,
Ar ₄ , Ar ₅ and Ar ₆ represent the same or different arylene groups. X, k, j and n are the same as in the case of the general formula (1).

[0013]

[Chemical 29] In the formula, R ₁₁ and R ₁₂ are substituted or unsubstituted aryl groups,
Ar ₇ , Ar ₈ and Ar ₉ are the same or different arylene groups,
p represents an integer of 1 to 5. X, k, j and n are the same as in the case of the general formula (1).

[0014]

Embedded image In the formula, R ₁₃ and R ₁₄ are substituted or unsubstituted aryl groups,
Ar ₁₀ , Ar ₁₁ and Ar ₁₂ represent the same or different arylene groups, and X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group. X, k, j and n are the same as in the case of the general formula (1).

[0015]

[Chemical 31] In the formula, R ₁₅ , R ₁₆ , R ₁₇ , and R ₁₈ are substituted or unsubstituted aryl groups, Ar ₁₃ , Ar ₁₄ , Ar ₁₅ , and Ar ₁₆ are the same,
Or different arylene groups, Y ₁ , Y ₂ and Y ₃ are 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 They represent a vinylene group and may be the same or different. X, k, j and n
Is the same as in the case of the general formula (1).

[0016]

Embedded image In the formula, R ₁₉ and R _{20 each} represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁₉ and R ₂₀ may form a ring. Ar ₁₇ , Ar ₁₈ and Ar ₁₉ represent the same or different arylene groups. X, k, j and n are represented by the general formula (1)
Is the same as

[0017]

[Chemical 33] In the formula, R ₂₁ is a substituted or unsubstituted aryl group, A ₂₁
r ₂₀ , Ar ₂₁ , Ar ₂₂ , and Ar ₂₃ represent the same or different arylene groups. X, k, j and n are represented by the general formula (1)
Is the same as

[0018]

Embedded image In the formula, R ₂₂ , R ₂₃ , R ₂₄ and R ₂₅ are substituted or unsubstituted aryl groups, Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , Ar ₂₇ and Ar _28.
Represent the same or different arylene groups. X, k, j and n are the same as in the case of the general formula (1).

[0019]

Embedded image In the formula, R ₂₆ and R ₂₇ are substituted or unsubstituted aryl groups,
Ar ₂₉ , Ar ₃₀ , and Ar ₃₁ represent the same or different arylene groups. X, k, j and n are the same as in the case of the general formula (1).

[0020]

Embedded image In the formula, R ₂₀₁ , R ₂₀₂ , R ₂₀₃ , and R ₂₀₄ represent a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a substituted or unsubstituted aryl group, and Ar ₁₀₁ represents a substituted or unsubstituted aryl group. , Ar ₁₀₂ represents a substituted or unsubstituted arylene group, Ar ₁₀₁ and R ₂₀₁ may together form a ring, and n ₁ is 0 or an integer of 1.

[0021]

Embedded image In the formula, R ₂₀₅ represents a lower alkyl group, a lower alkoxy group or a halogen atom, n ₂ represents an integer of 0 to 4,
₂₀₆ and R ₂₀₇ may be the same or different and each represents a hydrogen atom,
It represents a lower alkyl group, a lower alkoxy group, or a halogen atom.

[0022]

Embedded image In the formula, R ₂₀₈ represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic residue, and R _208
209 and R ₂₁₀ may be the same or different and include a hydrogen atom,
A lower alkyl group, a hydroxyalkyl group having 1 to 4 carbon atoms, a chloroalkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aralkyl group, and R ₂₀₉ and R ₂₁₀ jointly contain a nitrogen-containing compound ring R ₂₁₁ , R ₂₁₂
May be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom.

[0023]

Embedded image In the formula, R ₂₁₃ represents a hydrogen atom or a halogen atom, and R _213
214 is a substituted or unsubstituted aromatic residue, or a heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, It is either a lower alkoxy group or a nitro group).

[0024]

Embedded image In the formula, R ₂₁₅ , R ₂₁₆ , and R ₂₁₇ each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a heterocyclic group, and at least two of R ₂₁₅ , R ₂₁₆ , and R ₂₁₇ are represented. Represents an aryl group or a heterocyclic group.

[0025]

Embedded image In the formula, Ar ₁₀₃ and Ar ₁₀₄ each represent a substituted or unsubstituted aryl group or a heteroaromatic ring.

[0026]

Embedded image In the formula, Ar ₁₀₅ represents a substituted or unsubstituted aryl group or a heteroaromatic ring, and R ₂₁₈ and R ₂₁₉ are a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a heterocyclic group, respectively. , R ₂₁₈ , and R ₂₁₉ are at least one of an aryl group or a heterocyclic group.

[0027]

Embedded image In the formula, R ₂₂₀ and R ₂₂₂ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R _220
221 is a hydrogen atom, a lower alkyl group, a lower alkoxy group,
Represents a halogen atom or a nitro group, n ₃ is 0 or 1
Represents the integer.

[0028]

Embedded image In the formula, R ₂₂₃ is a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group,
Or an anthryl group (provided that the substituent is any one of a di-lower alkylamino group, a lower alkyl group, a lower alkoxy group, a halogen atom, an aralkylamino group, and an amino group).

[0029]

Embedded image In the formula, Ar ₁₀₆ represents a substituted or unsubstituted biphenylene group, R ₂₂₄ , R ₂₂₅ , and R ₂₂₆ represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl group, an alkoxy group, It represents an aryloxy group, an alkylmercapto group, a methylenedioxy group, a methylenedithio group, or an aryl group, and R ₂₂₄ , R ₂₂₅ , and R ₂₂₆ may be the same or different. U, v, and w each represent an integer of 1 to 5, and when each is an integer of 2 to 5, R ₂₂₄ and R
₂₂₅ and R ₂₂₆ may be the same or different.

[0030]

Embedded image In the formula, R ₂₂₇ and R ₂₂₈ represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and R _227
At least one of ₂₂₇ and R ₂₂₈ represents a substituted or unsubstituted aryl group.

The present invention will be described in detail below. The electrophotographic photosensitive member according to the present invention having the above structure has high sensitivity, a small residual potential, and excellent high-speed response. The reason for this is not clear at this time, but it is believed that it is due to the following circumstances. That is, since the polymer charge transport material itself is a polymer, it is excellent in mechanical durability, but its structural freedom limits the three-dimensional degree of freedom. Therefore, when it is used as a charge transport substance, contact with the charge generation substance is not sufficiently secured, and the number of carrier generation sites is insufficient. On the other hand, in the electrophotographic photoreceptor having the above structure, by providing the charge injection layer containing a low-molecular charge transport material as a main component, it is possible to sufficiently maintain contact with the charge generation material in the charge generation layer, Therefore, since the number of carrier generation sites is sufficient, high sensitivity can be expressed. Further, in the photoconductor of the present invention, since the charge transport material in the charge transport layer is composed of a polymer charge transport material as a main component, high density of charge transport sites can be achieved while maintaining high mechanical durability. Based on the above, high mobility can be expressed. Therefore, it has a high-speed photoresponsiveness which cannot be realized by the low molecular weight charge transport material-inert polymer alone system.

Next, the structure of the electrophotographic photosensitive member of the present invention will be described with reference to the drawings. FIG. 1 is a cross-sectional view showing an electrophotographic photoreceptor of the present invention, which is composed of a photosensitive layer 20 in which a charge generation layer 21, a charge injection layer 23 and a charge transport layer 25 are laminated on a conductive support 11. Is taking. FIG. 2 is a cross-sectional view showing an electrophotographic photosensitive member having still another structure, in which an intermediate layer 15 is provided between the conductive support 11 and the photosensitive layer 20. FIG. 3 is a cross-sectional view showing an electrophotographic photosensitive member having still another structure, in which the protective layer 17 is provided on the photosensitive layer 20.

[0033]

BEST MODE FOR CARRYING OUT THE INVENTION As described above, the polymer charge transport material used in the present invention has the general formulas (1) to (1) shown above.
0). First, specific examples of the polymer charge transport material represented by the general formula (1) are shown. However, the present invention is not limited to these.

[0034]

Embedded image

Specific examples of the general formula (1) R ₁ , R ₂ and R ₃ each independently represent a substituted or unsubstituted alkyl group or a halogen atom. Specific examples thereof include the following. And can be the same or different. The alkyl group is preferably C ₁
-C ₁₂ especially C ₁ -C _8, more preferably a straight chain or branched chain alkyl group of C ₁ -C _4, these alkyl groups may be further substituted fluorine atom, a hydroxyl group, a cyano group, C ₁ -C ₄
Alkoxy group, phenyl group, or halogen atom, C ₁
It may contain a phenyl group substituted with a C ₄ to C ₄ alkyl group or a C _{1 to} C ₄ alkoxy group. In particular,
Methyl group, ethyl group, 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, benzyl group, 4-chlorobenzyl group, 4-methylbenzyl group, 4-methoxybenzyl group,
4-phenylbenzyl group etc. are mentioned. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

R ₄ represents a hydrogen atom or a substituted or unsubstituted alkyl group, and specific examples of the alkyl group include those similar to the above R ₁ , R ₂ and R ₃ .

R ₅ and R ₆ represent a substituted or unsubstituted aryl group, and specific examples thereof include the following, which may be the same or different. As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, a triphenylenyl group, a chrysenyl group, Examples thereof include a fluorenylidenephenyl group, a 5H-dibenzo [a, d] cycloheptenylidenephenyl group, and a non-condensed polycyclic group such as a biphenylyl group and a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzthienyl group, a furyl group, a benzofuranyl group and a carbazolyl group.

The above aryl group may have the following groups as a substituent. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) Examples of the alkyl group include those similar to the above R ₁ , R ₂ and R ₃ . (3) As the alkoxy group (-OR ₁₀₅ ), R ₁₀₅ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group, the C _{1 to} C ₄ alkyl group, or the halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be Specific examples of the substituted mercapto group or arylmercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, an N, N-dibenzylamino group, and the like. (7) Specific examples of the acyl group 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 (A), which is polymerized by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (B) is used in combination with the main chain. Introduced in. In this case, the produced polycarbonate resin is a random copolymer or a block copolymer. 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 (A) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0040]

Embedded image

[0041]

Embedded image

Specific examples of the diol compound of the general formula (B) include the following. 1,3-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,
Examples thereof include aliphatic diols such as polyethylene glycol and polytetramethylene ether glycol, and cyclic aliphatic diols such as 1,4-cyclohexanediol, 1,3-cyclohexanediol, and cyclohexane-1,4-dimethanol.

As the diol having an aromatic ring,
4,4'-dihydroxydiphenyl, bis (4-hydroxyphenyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, 1,1-bis (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′-dihydroxydiphenylsulfone,
4'-dihydroxydiphenylsulfoxide, 4,4 '
-Dihydroxydiphenyl sulfide, 3,3'-dimethyl-4,4'-dihydroxydiphenyl sulfide,
4,4'-dihydroxydiphenyl oxide, 2,2-
Bis (4-hydroxyphenyl) hexafluoroproban, 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 oil and the like.

Tables 1 to 3 show synthetic examples of compounds of the general formula (1).

[0045]

[Table 1]

[0046]

[Table 2]

[0047]

[Table 3]

Next, specific examples of the polymer charge transport material represented by the general formula (2) will be shown. However, the present invention is not limited to these.

[0049]

Embedded image

Specific examples of the general formula (2) R ₇ and R ₈ represent a substituted or unsubstituted aryl group,
Specific examples thereof include the following, which may be the same or different. As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, a triphenylenyl group, a chrysenyl group, Examples thereof include a fluorenylidenephenyl group, a 5H-dibenzo [a, d] cycloheptenylidenephenyl group, a biphenylyl group, a terphenylyl group as a non-condensed polycyclic group, or a group represented by the following general formula (2-1). .

[0051]

[Chemical 51] Wherein, W is -O -, - S -, - SO -, - SO 2 -, -
CO- and the following general formulas (2-2), (2-3), (2
-4) and represents a divalent group represented by (2-5).

[0052]

Embedded image In the formula, c represents an integer of 1 to 12.

[0053]

Embedded image In the formula, d represents an integer of 1 to 3.

[0054]

Embedded image In the formula, e represents an integer of 1 to 3.

[0055]

Embedded image In the formula, f represents an integer of 1 to 3.

Examples of the heterocyclic group include thienyl group, benzothienyl group, furyl group, benzofuranyl group and carbazolyl group. In addition, Ar ₁ , Ar ₂ , and Ar ₃
Examples of the arylene group represented by are the divalent groups of R ₇ and the aryl group represented by R ₈ , and they may be the same or different.

The above-mentioned aryl group and arylene group may have the following groups as a substituent. Further, these substituents are represented as specific examples of R ₁₀₆ , R ₁₀₇ and R _{108 in} the above general formula. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
In particular, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight chain,
Or a branched chain alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group, a phenyl group, a halogen atom, a C _{1 to} C ₄ alkyl group or C ₁ It may contain a phenyl group substituted with a C ₄ -alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, 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) Examples of the alkoxy group (-OR _109), R ₁₀₉ represents an alkyl group specified in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group of, a C ₁ -C ₄ alkyl group, or a halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be Specific examples of the substituted mercapto group or arylmercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) Group represented by the following general formula (2-6)

[0058]

Embedded image In the formula, R ₁₁₀ and R ₁₁₁ each independently represent an alkyl group or an aryl group defined in (2), and examples of the aryl group include a phenyl group, a biphenyl group, and a naphthyl group, and these are C ₁ To C ₄ alkoxy groups, C _{1 to} C ₄
The above alkyl group or halogen atom may be contained as a substituent. Further, a ring may be formed together with a carbon atom on the aryl group. Specifically, diethylamino group, N-methyl-N-phenylamino group, N, N-diphenylamino group, N, N-di (p-tolyl) amino group, dibenzylamino group, piberidino group, morpholino group, Examples thereof include a urolydyl group. (7) An alkylenedioxy group such as a methylenedioxy group or a methylenedithio group, or an alkylenedithio group.

When X is a diol compound having a triarylamino group represented by the following general formula (C), which is polymerized by the phosgene method, transesterification method or the like, a diol compound represented by the following general formula (B) is used in combination to form a main chain. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (C) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0060]

Embedded image

[0061]

Embedded image

Specific examples of the diol compound of the general formula (B) are the same as those of the general formula (1).

Tables 4 to 6 show synthetic examples of the compound of the general formula (2).

[0064]

[Table 4]

[0065]

[Table 5]

[0066]

[Table 6]

Next, specific examples of the polymer charge transport substance represented by the general formula (3) will be shown. However, the present invention is not limited to these.

[0068]

Embedded image

Specific examples of the general formula (3) R ₉ and R ₁₀ represent a substituted or unsubstituted aryl group, and specific examples thereof include the following, which may be the same or different. Good. The aromatic hydrocarbon group is a phenyl group, the condensed polycyclic group is a naphthyl group,
Pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-
2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group,
And a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group and a carbazolyl group. Also,
Examples of the arylene group represented by Ar ₄ , Ar ₅ and Ar ₆ include the divalent groups of the aryl groups represented by R ₉ and R ₁₀ , and they may be the same or different.

The above aryl group and arylene group may have the following groups as a substituent.

(1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
In particular, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight chain,
Or a branched chain alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group, a phenyl group, a halogen atom, a C _{1 to} C ₄ alkyl group or C ₁ It may contain a phenyl group substituted with a C ₄ -alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, 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) As the alkoxy group (-OR ₁₁₂ ), R ₁₁₂ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group of, a C ₁ -C ₄ alkyl group, or a halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be Specific examples of the substituted mercapto group or arylmercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specific examples include dimethylamido / group, diethylamino group, N-methyl-N-propylamino group, N, N-dibenzylamino group and the like. (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 (D), which is polymerized by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (B) is used in combination with the main chain. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (D) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0073]

Embedded image

[0074]

[Chemical formula 61]

As the diol compound of the general formula (B), the same ones as in the case of the general formula (1) can be mentioned.

Tables 7 to 8 show synthesis examples of the general formula (3).

[0077]

[Table 7]

[0078]

[Table 8]

Next, specific examples of the polymer charge transport material represented by the general formula (4) will be shown. However, the present invention is not limited to these.

[0080]

Embedded image

Specific examples of the general formula (4) R ₁₁ and R ₁₂ represent a substituted or unsubstituted aryl group, and specific examples thereof include the following, which may be the same or different. Good. The aromatic hydrocarbon group is a phenyl group, the condensed polycyclic group is a naphthyl group,
Pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-
2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group,
And a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group and a carbazolyl group. Also,
Examples of the arylene group represented by Ar ₇ , Ar ₈ and Ar ₉ include the divalent groups of the aryl groups represented by R ₁₁ and R ₁₂ , which may be the same or different.

The above aryl group and arylene group may have the following groups as a ring-positioning group. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
In particular, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight chain,
Or a branched chain alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group, a phenyl group, a halogen atom, a C _{1 to} C ₄ alkyl group or C ₁ It may contain a phenyl group substituted with a C ₄ -alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, 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. As the alkoxy group (—OR ₁₁₃ ), R ₁₁₃ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group, the C _{1 to} C ₄ alkyl group, or the halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be Specific examples of the substituted mercapto group or arylmercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, an N, N-dibenzylamino group, and the like. (7) Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group and a benzoyl group.

X is a main chain obtained by using a diol compound of the following general formula (B) in combination when a diol compound having a triarylamino group of the following general formula (E) is polymerized by the phosgene method, transesterification method or the like. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (E) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0084]

Embedded image

[0085]

Embedded image

As the diol compound of the general formula (B), the same ones as in the case of the general formula (1) can be mentioned.

Tables 9 to 10 show synthesis examples of the general formula (4).

[0088]

[Table 9]

[0089]

[Table 10]

Next, specific examples of the polymer charge transport material represented by the general formula (5) will be shown. However, the present invention is not limited to these.

[0091]

Embedded image

Specific examples of the general formula (5) R ₁₃ and R _{14 each} represent a substituted or unsubstituted aryl group, and specific examples thereof include the following, which may be the same or different. Good. The aromatic hydrocarbon group is a phenyl group, the condensed polycyclic group is a naphthyl group,
Pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-
2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group,
And a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group and a carbazolyl group. Also,
Examples of the arylene group represented by Ar ₁₀ , Ar ₁₁ and Ar ₁₂ include the divalent groups of the aryl groups represented by R ₁₃ and R ₁₄ , which may be the same or different.

The above aryl group and arylene group may have the following groups as a substituent. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
In particular, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight chain,
Or a branched chain alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group, a phenyl group, a halogen atom, a C _{1 to} C ₄ alkyl group or C ₁ It may contain a phenyl group substituted with a C ₄ -alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, 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) As the alkoxy group (-OR ₁₁₄ ), R ₁₁₄ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group, the C _{1 to} C ₄ alkyl group, or the halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be Specific examples of the substituted mercapto group or arylmercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, an N, N-dibenzylamino group, and the like. (7) Specific examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, a malonyl group and a benzoyl group.

X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group, and examples of the substituent include a cyano group, a halogen atom, a nitro group, R ₁₃ and R ₁₄ above. Examples thereof include an aryl group and the alkyl group described in (2) above.

When X is a diol compound having a triarylamino group represented by the following general formula (F), which is polymerized by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (B) is used in combination with the main chain. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (F) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0096]

Embedded image

[0097]

Embedded image

As the diol compound of the general formula (B), the same ones as in the case of the general formula (1) can be mentioned.

Tables 11 to 13 show synthesis examples of the general formula (5).

[0100]

[Table 11]

[0101]

[Table 12]

[0102]

[Table 13]

Next, specific examples of the polymer charge transport material represented by the general formula (6) will be shown. However, the present invention is not limited to these.

[0104]

Embedded image

Specific examples of the general formula (6) R ₁₅ , R ₁₆ , R ₁₇ and R _{18 each} represent a substituted or unsubstituted aryl group. Specific examples thereof include the following and are the same. It may or may not be. As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, a triphenylenyl group, a chrysenyl group, Examples thereof include a fluorenylidenephenyl group, a 5H-dibenzo [a, d] cycloheptenylidenephenyl group, and a non-condensed polycyclic group such as a biphenylyl group and a terphenylyl group. As the heterocyclic group, a thienyl group, a benzothienyl group, a furyl group,
Examples thereof include a benzofuranyl group and a carbazolyl group.
Examples of the arylene group represented by Ar ₁₃ , Ar ₁₄ , Ar ₁₅ and Ar ₁₆ include the divalent groups of the above aryl groups represented by R ₁₅ , R ₁₆ , R ₁₇ and R _18, which are the same. Or may be different.

The above-mentioned aryl group and arylene group may have the following groups as a ring-positioning group. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
Particularly, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ linear or branched alkyl groups, and these alkyl groups further include 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, methyl, ethyl, n-propyl, i-propyl, 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) As the alkoxy group (-OR ₁₁₅ ), R ₁₁₅ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group, the C _{1 to} C ₄ alkyl group, or the halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be

Y ₁ , Y ₂ and Y ₃ are 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. They may be the same or different. The alkylene group represents a divalent group derived from the alkyl group shown in (2) above. Specifically, methylene group, 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,
2,2-propylene group, 2,2-butylene group, diphenylmethylene group and the like can be mentioned. As the cycloalkylene group, 1,1-cyclopentylene group, 1,1-
Examples thereof include a cyclohexylene group and a 1,1-cyclooctylene group. As the alkylene ether group,
Examples thereof include a dimethylene ether group, a diethylene ether group, an ethylenemethylene ether group, a bis (triethylene) ether group, and a polytetramethylene ether group.

X is a main chain obtained by using a diol compound of the following general formula (B) in combination when a diol compound having a triarylamino group of the following general formula (G) is polymerized by the phosgene method, transesterification method or the like. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (G) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0109]

Embedded image

[0110]

Embedded image

As the diol compound of the general formula (B), the same ones as in the case of the general formula (1) can be mentioned.

Tables 14 to 15 show synthesis examples of the general formula (6).

[0113]

[Table 14]

[0114]

[Table 15]

Next, specific examples of the polymer charge transport material represented by the general formula (7) will be shown. However, the present invention is not limited to these.

[0116]

Embedded image

Specific examples of the general formula (7) R ₁₉ and R _{20 each} represent a substituted or unsubstituted aryl group, and specific examples thereof include the following, which may be the same or different. Good. The aromatic hydrocarbon group is a phenyl group, the condensed polycyclic group is a naphthyl group,
Pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-
2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group,
And a terphenylyl group. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group and a carbazolyl group. Also,
When R ₁₉ and R ₂₀ form a ring, examples thereof include 9-fluorenylidene and 5H-dibenzo [a, d] cycloheptenylidene. The arylene groups represented by Ar ₁₇ , Ar ₁₈ and Ar ₁₉ include the divalent groups of the aryl groups represented by R ₁₉ and R ₂₀ , which may be the same or different.

The above aryl group and arylene group may have the following groups as a substituent. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
In particular, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight chain,
Or a branched chain alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group, a phenyl group, or a halogen atom, a C _{1 to} C ₄ alkyl group or C ₁ It may contain a phenyl group substituted with a C ₄ -alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, 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) As the alkoxy group (-OR ₁₁₆ ), R ₁₁₆ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2-
Examples thereof include a cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group and a trifluoromethoxy group. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. It may contain a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkyl group, or a halogen atom as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be Specific examples of the substituted mercapto group or aryl mercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, an N, N-dibenzylamino group, and the like. Specific examples of the acyl group (7) 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 (H), which is polymerized by a phosgene method, a transesterification method or the like, a diol compound represented by the following general formula (B) is used in combination to form a main chain. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (H) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0120]

Embedded image

[0121]

Embedded image

As the diol compound of the general formula (B), the same ones as in the case of the general formula (1) can be mentioned.

Tables 16 to 17 show synthesis examples of the general formula (7).

[0124]

[Table 16]

[0125]

[Table 17]

Specific examples of the polymeric charge transporting material represented by the general formula (8) are shown below. However, the present invention is not limited to these.

[0127]

Embedded image

Specific Examples of General Formula (8) R ₂₁ represents a substituted or unsubstituted aryl group, and specific examples thereof include the following, which may be the same or different. As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group, a pyrenyl group,
2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5
Examples thereof include H-dibenzo [a, d] cycloheptenylidenephenyl group, and non-condensed polycyclic group such as biphenylyl group and terphenylyl group. As the heterocyclic group, a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group,
Examples thereof include a carbazolyl group. In addition, Ar ₂₀ , Ar
Examples of the arylene group represented by ₂₁ , Ar ₂₂ and Ar ₂₃ include the divalent group of the aryl group represented by R ₂₁ , and they may be the same or different.

The above-mentioned aryl group and arylene group may have the following groups as a substituent. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
In particular, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight chain,
Or a branched chain alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group, a phenyl group, a halogen atom, a C _{1 to} C ₄ alkyl group or C ₁ It may contain a phenyl group substituted with a C ₄ -alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, 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) As the alkoxy group (-OR ₁₁₇ ), R ₁₁₇ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group of, a C ₁ -C ₄ alkyl group, or a halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be Specific examples of the substituted mercapto group or arylmercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, an N, N-dibenzylamino group, and the like. Specific examples of the acyl group (7) 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 (J), which is polymerized by a phosgene method, a transesterification method, etc., a diol compound represented by the following general formula (B) is used in combination to form a main chain. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (J) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0131]

Embedded image

[0132]

[Chemical 76]

Examples of the diol compound of the general formula (B) include the same ones as in the case of the general formula (1).

Tables 18 to 21 show synthesis examples of the general formula (8).

[0135]

[Table 18]

[0136]

[Table 19]

[0137]

[Table 20]

[0138]

[Table 21]

Next, specific examples of the polymer charge transport material represented by the general formula (9) will be shown. However, the present invention is not limited to these.

[0140]

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Specific examples of the general formula (9) R ₂₂ , R ₂₃ , R ₂₄ and R _{25 each} represent a substituted or unsubstituted aryl group, and specific examples thereof include the following and are the same. It may or may not be. As the aromatic hydrocarbon group, a phenyl group, a naphthyl group as a condensed polycyclic group, a pyrenyl group, a 2-fluorenyl group, a 9,9-dimethyl-2-fluorenyl group, an azulenyl group, an anthryl group, a triphenylenyl group, a chrysenyl group, Examples thereof include a fluorenylidenephenyl group, a 5H-dibenzo [a, d] cycloheptenylidenephenyl group, and a non-condensed polycyclic group such as a biphenylyl group and a terphenylyl group. As the heterocyclic group, a thienyl group, a benzothienyl group, a furyl group,
Examples thereof include a benzofuranyl group and a carbazolyl group.
Examples of the arylene group represented by Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , Ar ₂₇ , and Ar ₂₈ include the divalent groups of the above aryl groups represented by R ₂₂ , R ₂₃ , R ₂₄ , and R _25. And may be the same or different.

The above-mentioned aryl group and arylene group may have the following groups as a substituent. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
In particular, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight chain,
Or a branched chain alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group, a phenyl group, a halogen atom, a C _{1 to} C ₄ alkyl group or C ₁ It may contain a phenyl group substituted with a C ₄ -alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, 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. As the alkoxy group (-OR ₁₁₈ ) (3), R ₁₁₈ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group, the C _{1 to} C ₄ alkyl group, or the halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group and a 6-methyl-2naphthyloxy group. Specific examples of the substituted mercapto group or arylmercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, an N, N-dibenzylamino group, and the like. Specific examples of the acyl group (7) include an acetyl group, a propionyl group, a butyryl group, a malonyl group and a benzoyl group.

X is a main chain obtained by using a diol compound of the following general formula (B) in combination when a diol compound having a triarylamino group of the following general formula (L) is polymerized by the phosgene method, transesterification method or the like. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (L) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0144]

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[0145]

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As the diol compound of the general formula (B), the same ones as in the case of the general formula (1) can be mentioned.

Tables 22 to 23 show synthesis examples of the general formula (9).

[0148]

[Table 22]

[0149]

[Table 23]

Next, specific examples of the polymer charge transport material represented by the general formula (10) will be shown. However, the present invention is not limited to these.

[0151]

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Specific examples of the general formula (10): R ₂₆ and R _{27 each} represent a substituted or unsubstituted aryl group, and specific examples thereof include the following, which may be the same or different. Good. Phenyl group as aromatic hydrocarbon group, naphthyl group as condensed polycyclic group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2
-Fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, biphenylyl group as a non-condensed polycyclic group, terphenylyl group, etc. Is mentioned. Examples of the heterocyclic group include a thienyl group, a benzothienyl group, a furyl group, a benzofuranyl group and a carbazolyl group. Also, A
Examples of the arylene group represented by r ₂₉ , Ar ₃₀ , and Ar ₃₁ include the divalent groups of the aryl group represented by R ₂₆ and R ₂₇ , which may be the same or different.

The above-mentioned aryl group and arylene group may have the following groups as a substituent. (1) Halogen atom, trifluoromethyl group, cyano group, nitro group. (2) The alkyl group is preferably C _{1 to} C ₁₂ ,
In particular, C _{1 to} C ₈ , more preferably C _{1 to} C ₄ straight chain,
Or a branched chain alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, a C _{1 to} C ₄ alkoxy group, a phenyl group, a halogen atom, a C _{1 to} C ₄ alkyl group or C ₁ It may contain a phenyl group substituted with a C ₄ -alkoxy group. Specifically, methyl, ethyl, n-propyl, i-propyl, 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) As the alkoxy group (-OR ₁₁₉ ), R ₁₁₉ represents the alkyl group defined in (2). Specifically, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, t-butoxy group, n-butoxy group, s-butoxy group, i-butoxy group, 2-hydroxyethoxy group, 2
-A cyanoethoxy group, a benzyloxy group, a 4-methylbenzyloxy group, a trifluoromethoxy group and the like. (4) The aryloxy group includes a phenyl group and a naphthyl group as the aryl group. This is C _{1 to} C ₄
The alkoxy group, the C _{1 to} C ₄ alkyl group, or the halogen atom may be contained as a substituent. Specific examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methylphenoxy group, a 4-methoxyphenoxy group, a 4-chlorophenoxy group, a 6-methyl-2-naphthyloxy group, and the like. Can be Specific examples of the substituted mercapto group or arylmercapto group (5) include a methylthio group, an ethylthio group, a phenylthio group and a p-methylphenylthio group. (6) As the alkyl-substituted amino group, the alkyl group represents the alkyl group defined in (2). Specific examples thereof include a dimethylamino group, diethylami / group, N-methyl-N-propylamino group, N, N-dibenzylamino group and the like. Specific examples of the acyl group (7) include an acetyl group, a propionyl group, a butyryl group, a malonyl group and a benzoyl group.

X is a main chain obtained by using a diol compound of the following general formula (B) in combination when a diol compound having a triarylamino group of the following general formula (M) is polymerized by the phosgene method, transesterification method or the like. Introduced in. In this case, the produced polycarbonate resin becomes a random copolymer or a block copolymer. 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 (M) and a bischloroformate derived from the following general formula (B). In this case, the polycarbonate produced is an alternating copolymer.

[0155]

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[0156]

[Chemical formula 82]

As the diol compound of the general formula (B), the same ones as in the case of the general formula (1) can be mentioned.

Tables 24 to 26 show synthesis examples of the general formula (10).

[0159]

[Table 24]

[0160]

[Table 25]

[0161]

[Table 26]

Next, the conductive support 11 has conductivity with a volume resistance of 10 ¹⁰ Ωcm or less, for example, metals such as aluminum, nickel, chromium, copper, silver, gold and platinum, tin oxide and indium oxide. Film- or cylindrical plastics or papers coated with metal oxides such as metal oxides by vapor deposition or sputtering, or plates of aluminum, aluminum alloys, nickel, stainless steel, etc., and D. I. , I. I. Extruded,
It is possible to use a tube or the like which is made into a raw tube by a method such as drawing and then surface-treated by cutting, superfinishing, polishing or the like.

Next, the laminated photosensitive layer will be described. The laminated photosensitive layer includes a charge generation layer 21, a charge injection layer 23 and a charge transport layer 25. The charge generation layer 21 is a layer containing a charge generation substance as a main component. As the charge generation substance, an inorganic material and an organic material can be used. Examples of the inorganic material include crystalline selenium, amorphous selenium, selenium-tellurium, selenium-tellurium-halogen, selenium-arsenic compounds, and amorphous silicon. As amorphous silicon, a material obtained by terminating a dangling bond with a hydrogen atom or a halogen atom, or a material doped with a boron atom, a phosphorus atom, or the like is preferably used. On the other hand, a known material can be used as the organic material. For example, phthalocyanine-based pigments such as metal phthalocyanine and metal-free phthalocyanine, azurenium salt pigments, squalic acid methine pigments, azo pigments having a carbazole skeleton, azo pigments having a triphenylamine skeleton, azo pigments having a diphenylamine skeleton, and dibenzothiophene skeletons. Having an azo pigment, an azo pigment having a fluorenone skeleton, an azo pigment having an oxadiazole skeleton, an azo pigment having a bisstilbene skeleton, an azo pigment having a distyryl oxadiazole skeleton, an azo pigment having a distyrylcarbazole skeleton, a perylene-based pigment Pigment, anthraquinone-based or polycyclic quinone-based pigment, quinone imine-based pigment, diphenylmethane, and triphenylmethane-based pigment, benzoquinone, and naphthoquinone-based pigment,
Examples include cyanine and azomethine pigments, indigoid pigments, and bisbenzimidazole pigments.
These charge generating substances can be used alone or as a mixture of two or more kinds.

As the binder resin used as necessary, in addition to the polymer compounds represented by the above general formulas (1) to (10), polyamide, polyurethane, epoxy resin, polyketone, polycarbonate, silicone resin,
Acrylic resin, polyvinyl butyral, polyvinyl formal, polyvinyl ketone, polystyrene, poly-N-
Vinylcarbazole, polyacrylamide, etc. are used. These binder resins can be used alone or as a mixture of two or more kinds.

As a method for forming the charge generation layer 21, a vacuum thin film forming method and a casting method from a solution dispersion system can be largely cited. For the former 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, etc. are used.
As the charge generation layer 17, the above-mentioned inorganic material and organic material can be favorably formed. Further, in order to provide the charge generation layer by the casting method described below, a ball mill using a solvent such as tetrahydrofuran, cyclohexanone, dioxane, dichloroethane, butanone together with the above-mentioned inorganic or organic charge generation substance together with a binder resin if necessary. , An attritor, a sand mill or the like, and the dispersion is appropriately diluted and applied. The coating can be performed by a dip coating method, a spray coating method, a bead coating method, or the like.

The film thickness of the charge generation layer provided as described above is suitably about 0.01 to 5 μm, preferably 0.05 to 2 μm.

Examples of the charge generating substance which absorbs light having a wavelength longer than 700 nm and generates charges include trisazo pigments, squaric acid type dyes, phthalocyanine type pigments, naphthalocyanine type pigments, azurenium salt type dyes and amorphous silicon. Used. Charge generating substances that absorb light having a wavelength shorter than 500 nm and generate charges include monoazo pigments, disazo pigments, trisazo pigments, perylene pigments,
Perinone pigments, quinacridone pigments, quinone condensed polycyclic compounds, squaric acid dyes, phthalocyanine pigments, naphthalocyanine pigments, azurenium salt dyes,
Selenium, selenium-tellurium, selenium-arsenic compounds, amorphous silicon and the like can be mentioned and used.

The charge transport layer 25 is a layer containing as a main component at least one of the polymer charge transport substances represented by the general formulas (1) to (10). Charge transport layer 2
5 can be formed by dissolving or dispersing a polymer charge transporting substance in a suitable solvent such as tetrahydrofuran, dioxane, toluene, monochlorobenzene, dichloroethane, methylene chloride, cyclohexanone, and coating and drying. In addition, the charge transport layer 25, if necessary,
A plasticizer, a leveling agent, etc. may be added, and a binder resin may be used in combination, if necessary.

The binder resin used as required includes polystyrene, styrene-acrylonitrile copolymer, styrene-butadiene copolymer, styrene-maleic anhydride copolymer, polyester, polyvinyl chloride, vinyl chloride-acetic acid. Vinyl copolymer, polyvinyl acetate, polyvinylidene chloride, polyarylate resin, phenoxy resin, polycarbonate, cellulose acetate resin, ethyl cellulose resin, polyvinyl butyral, polyvinyl formal, polyvinyl toluene, acrylic resin, silicone resin, epoxy resin, melamine resin, Urethane resin,
Thermoplastic or thermosetting resins such as phenolic resins and alkyd resins may be mentioned. The amount of binder resin used is
Generally, it is 0 to 1 with respect to 100 parts by weight of the polymer charge transporting substance, although it depends on the polymer charge transporting substance used.
50 parts by weight is suitable.

As the plasticizer which may be added to the charge transport layer 25, 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 is the polymer component. About 0 to 30 parts by weight is suitable for 100 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.
About 0 to 1 part by weight is suitable for 0 part by weight. A suitable thickness of the charge transport layer 25 is about 5 to 100 μm.

A charge injection layer in which the low molecular weight charge transport material represented by the general formulas (11) to (21) is contained alone or as a mixture of two or more kinds between the charge generation layer and the charge transport layer. Is provided.

The charge injection layer 23 is a layer containing a low molecular charge transport material as a main component. The low molecular weight charge transport material used for the charge injection layer 23 includes a hole transport material and an electron transport material. Examples of the electron transport material include chloranil, bromanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro-9-fluorenone, and 2,4. , 5,7-Tetranitroxanthone, 2,
4,8-Trinitrothioxanthone, 2,6,8-trinitro-4H-indeno [1,2-b] thiophene-4
On, 1,3,7-trinitrodibenzothiophene-
Examples thereof include electron accepting substances such as 5,5-dioxide. These electron transport materials can be used alone or as a mixture of two or more kinds. Examples of the hole-transporting substance include the electron-donating substances shown below, which are preferably used. For example, 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,
Examples thereof include benzimidazole derivatives and thiophene derivatives. These hole transport materials can be used alone or as a mixture of two or more kinds.

Among these low molecular weight charge transporting substances, the low molecular weight charge transporting substances represented by the above general formulas (11) to (21) are particularly preferably used. Since the low molecular weight charge transporting substances represented by the above general formulas (11) to (21) have almost no self-supporting property by themselves, a binder resin is used if necessary. As the binder resin which is preferably used, the materials listed for the charge transport layer and the above-mentioned general formulas (1) to
Examples thereof include the polymer charge transport substance represented by (10).

The appropriate amount of the low-molecular-weight charge transport material added to the charge injection layer according to the present invention differs depending on the material, and if the amount added is large, the self-supporting property and the mechanical durability of the layer itself are deteriorated. On the contrary, if the amount is small, the effect obtained may be small because the contact with the charge generating substance is not sufficient, and therefore it is desirable to determine by a preliminary test. Generally, an appropriate amount of the low-molecular charge transport material added is 5 to 200 parts by weight based on 100 parts by weight of the binder resin.

Further, in the electrophotographic photosensitive member of the present invention, an undercoat layer 15 can be provided between the conductive support 11 and the charge generation layer 21. The undercoat layer 15 generally contains a resin as a main component, but considering that the resin is applied to the charge generation layer 21 on the resin, the undercoat layer 15 is a resin having a high solubility in a general organic solvent. Is desirable. Such resins include polyvinyl alcohol, casein,
Water-soluble resin such as sodium polyacrylate, copolymer nylon, alcohol-soluble resin such as methoxymethylated nylon, polyurethane, melamine resin, alkyd-melamine resin, epoxy resin, curable resin that forms a three-dimensional network structure, etc. Can be mentioned. Further, in order to prevent moire and reduce the residual potential, the undercoat layer 15 may be added with a fine powder of a metal oxide such as titanium oxide, silica, alumina, zirconium oxide, tin oxide or indium oxide. These undercoat layers can be formed by using an appropriate solvent and coating method like the above-mentioned charge generation layer. Further, as the undercoat layer of the present invention, a metal oxide layer formed by a sol-gel method or the like using a silane coupling agent, a titanium coupling agent, a chromium coupling agent, etc. is also useful. In addition to this, the undercoat layer of the present invention may be formed of Al ₂
O ₃ provided by anodic oxidation, organic substances such as polyparaxylylene (parylene), SiO ₂ , SnO ₂ , TiO ₂ .
Those provided with an inorganic substance such as ₂ , ITO, CeO ₂ by a vacuum thin film forming method can also be favorably used. The thickness of the undercoat layer is 0 to 5
μm is suitable.

In the electrophotographic photosensitive member of the present invention, the protective layer 17 may be provided on the charge transport layer 25 for the purpose of protecting the photosensitive layer. The material used for this is ABS
Resin, ACS resin, olefin-vinyl monomer copolymer, chlorinated polyether, allyl resin, phenol resin, polyacetal, polyamide, polyamideimide,
Polyacrylate, polyallyl sulfone, polybutylene, polybutylene terephthalate, polycarbonate,
Polyether sulfone, polyethylene, polyethylene terephthalate, polyimide, acrylic resin, polymethylpentene, polypropylene, polyphenylene oxide,
Examples thereof include resins such as polysulfone, AS resin, AB resin, BS resin, polyurethane, polyvinyl chloride, polyvinylidene chloride, and epoxy resin. In addition to the protective layer, a fluororesin such as polytetrafluoroethylene, a silicone resin, and a dispersion of an inorganic material such as titanium oxide, tin oxide, or potassium titanate in these resins for the purpose of improving wear resistance. Can be added. As a method for forming the protective layer, a usual coating method is adopted. The thickness of the protective layer is preferably about 0.5 to 10 μm. In addition to the above, i-C formed by the vacuum thin film manufacturing method,
Known materials such as a-SiC can also be used as the protective layer.

Further, in the present invention, an antioxidant can be added for the purpose of improving the environment resistance, particularly for the purpose of preventing the sensitivity from lowering and the residual potential from rising. The antioxidant may be added to any layer containing an organic substance, but good results can be obtained by adding it to a layer containing a charge transporting substance. The following may be mentioned as antioxidants that can be used in the present invention.

Monophenol compounds 2,6-di-t-butyl-p-cresol, butylated hydroxyanisole, 2,6-di-t-butyl-4-ethylphenol, stearyl-β- (3,5- The-t-
Butyl-4-hydroxyphenyl) propionate and the like.

Bisphenol compounds 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'-butylidene bis- (3-methyl-6-t-butylphenol) and the like.

Polymer Phenolic Compound 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 ester, tocopherols and the like.

Para-phenylenediamines N-phenyl-N'-isoprovir-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-p-phenylenediamine and the like.

Hydroquinones 2,5-di-t-octylhydroquinone, 2,6-didodecylhydroquinone, 2-dodecylhydroquinone, 2-dodecyl-5-chlorohydroquinone, 2-t
-Octyl-5-methylhydroquinone, 2- (2-octadecenyl) -5-methylhydroquinone and the like.

Organic Sulfur Compounds Dilauryl-3,3′-thiodipropionate, distearyl-3,3′-thiodipropionate, ditetradecyl-3,3′-thiodipropionate and the like.

Organic Phosphorus Compounds Triphenylphosphine, tri (nonylphenyl) phosphine, tri (dinonylphenyl) phosphine, tricresylphosphine, tri (2,4-dibutylphenoxy) phosphine and the like.

These compounds are known as antioxidants for rubbers, plastics, oils and fats, and commercially available products can be easily obtained. The amount of the antioxidant added in the present invention is 0.1 to 100 parts by weight based on 100 parts by weight of the charge transport material.
Parts by weight, preferably 0.2 to 30 parts by weight.

The photoconductor of the present invention has the constitution as described above, and has high sensitivity and low residual potential as will be apparent from the examples described later.

[0187]

EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited by these. All parts in the examples are parts by weight.

Example 1 An undercoat layer coating solution having the following composition, then a charge generation layer coating solution, a charge injection layer coating solution, and a charge transport layer coating solution were sequentially formed on an aluminum plate. After coating and drying, an undercoat layer having a thickness of 3 μm, a charge generating layer having a thickness of 0.3 μm, a charge injection layer having a thickness of 5 μm, and a charge transporting layer having a thickness of 20 μm were formed, to prepare an electrophotographic photoreceptor of the present invention.

(Coating liquid for undercoat layer) Alkyd resin solution (manufactured by Dainippon Ink and Chemicals, Inc .: Beccolite M-6401-50) 375 parts Melamine resin solution (manufactured by Dainippon Ink and Chemicals: Super Beckamine G821) -60) 210 parts Titanium dioxide (manufactured by Ishihara Sangyo Co., Ltd .: Taipaque CR-EL) 250 parts 2-butanone 7800 parts

(Coating Liquid for Charge Generation Layer) 2.5 parts of charge generation substance having the following structural formula

[Chemical 83] Polysulfone (manufactured by Nissan Kagaku: P-1700) 1 part Cyclohexanone 175 parts Cyclohexane 75 parts

(Coating Liquid for Charge Injection Layer) 50 parts of a low molecular charge transport material having the following structural formula

Embedded image Polycarbonate resin (bisphenol Z polycarbonate: molecular weight 50,000) 50 parts Dichloromethane 560 parts Silicon oil (Shin-Etsu Chemical Co., Ltd .: KF50-100CS) 0.01 parts

(Coating Liquid for Charge Transport Layer) 120 parts of polymeric charge transport material having the following structure

Embedded image Dichloromethane 680 parts Silicon oil (KF50-100CS manufactured by Shin-Etsu Chemical Co., Ltd.) 0.01 part

Example 2 The procedure of Example 2 was repeated except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 3 Example 3 was repeated in the same manner as in Example 1 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 4 The procedure of Example 4 was repeated except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 5 The procedure of Example 5 was repeated except that the low-molecular-weight charge transporting substance added to the charge injection layer coating solution of Example 1 was replaced by the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 6 The procedure of Example 6 was repeated except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 1 was replaced by the compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 7 Example 7 was repeated in the same manner as in Example 1 except that the low molecular weight charge transporting substance added to the charge injection layer coating liquid of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 8 Example 8 was repeated in the same manner as in Example 1 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 9 The procedure of Example 9 was repeated except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 10 Example 10 was repeated in the same manner as in Example 1 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 11 The procedure of Example 11 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 12 The procedure of Example 12 was repeated except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 96]

Example 13 The same procedure as in Example 13 was carried out except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 14 The procedure of Example 14 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 15 The procedure of Example 15 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 1 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Comparative Example 1 Example 1 was repeated except that the low-molecular-weight charge transport material in the coating solution for the charge injection layer of Example 1 was removed.
An electrophotographic photoreceptor of Comparative Example 1 was produced in the same manner as in.

Example 16 An electrophotography of Example 16 was carried out in the same manner as in Example 1 except that the polymer charge transporting substance in the coating liquid for charge transporting layer of Example 1 was changed to the compound of the following structural formula. A photoconductor was prepared.

[Chemical 100]

Example 17 Example 1 was repeated in the same manner as in Example 16 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 16 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

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Example 18 Example 1 was repeated in the same manner as in Example 16 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

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Example 19 Example 1 was repeated in the same manner as in Example 16 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

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Example 20 Example 2 was repeated in the same manner as in Example 16 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
No. 0 electrophotographic photosensitive member was produced.

[Chemical 104]

Example 21 Example 2 was repeated in the same manner as in Example 16 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
The electrophotographic photoreceptor of No. 1 was produced.

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Example 22 Example 2 was repeated in the same manner as in Example 16 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 16 was changed to the compound having the following structural formula.
No. 2 electrophotographic photosensitive member was produced.

[Chemical formula 106]

Example 23 Example 2 was repeated in the same manner as in Example 16 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
The electrophotographic photoconductor of No. 3 was produced.

[Chemical formula 107]

Example 24 Example 2 was conducted in the same manner as in Example 16 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
The electrophotographic photosensitive member of No. 4 was produced.

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Example 25 Example 2 was repeated in the same manner as in Example 16 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
The electrophotographic photosensitive member of No. 5 was produced.

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Example 26 Example 2 was repeated in the same manner as in Example 16 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 16 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 6 was produced.

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Example 27 Example 2 was repeated in the same manner as in Example 16 except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

[Chemical 111]

Example 28 Example 2 was repeated in the same manner as in Example 16 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 16 was replaced by the compound having the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

[Chemical 112]

Example 29 Example 2 was conducted in the same manner as in Example 16 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 16 was changed to the compound of the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

[Chemical 113]

Example 30 Example 3 was repeated in the same manner as in Example 16 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 16 was changed to the compound of the following structural formula.
No. 0 electrophotographic photosensitive member was produced.

[Chemical 114]

Comparative Example 2 An electrophotographic photosensitive member of Example 30 was prepared in the same manner as in Example 16 except that the charge injection layer of Example 16 was not provided and the layer thickness of the charge transport layer was 25 μm. It was made.

[Example 31] An electrophotographic photograph of Example 31 was conducted in the same manner as in Example 1 except that the polymer charge transporting substance in the coating liquid for the charge transporting layer of Example 1 was changed to the compound of the following structural formula. A photoconductor was prepared.

[Chemical 115]

Example 32 Example 3 was repeated in the same manner as in Example 31 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 31 was replaced by the compound having the following structural formula.
No. 2 electrophotographic photosensitive member was produced.

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Example 33 Example 3 was repeated in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 31 was replaced by the compound having the following structural formula.
The electrophotographic photoconductor of No. 3 was produced.

[Chemical 117]

Example 34 Example 3 was repeated in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 31 was changed to the compound of the following structural formula.
The electrophotographic photosensitive member of No. 4 was produced.

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Example 35 Example 3 was carried out in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 31 was changed to the compound of the following structural formula.
The electrophotographic photosensitive member of No. 5 was produced.

[Chemical formula 119]

Example 36 Example 3 was carried out in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 31 was changed to the compound of the following structural formula.
The electrophotographic photoconductor of No. 6 was produced.

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Example 37 Example 3 was carried out in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 31 was changed to the compound of the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

[Chemical 121]

Example 38 Example 3 was carried out in the same manner as in Example 31 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 31 was replaced by the compound having the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

[Chemical formula 122]

Example 39 Example 3 was repeated in the same manner as in Example 31 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 31 was replaced by the compound having the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

[Chemical 123]

Example 40 Example 4 was carried out in the same manner as Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 31 was changed to the compound of the following structural formula.
No. 0 electrophotographic photosensitive member was produced.

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Example 41 Example 4 was effected in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 31 was changed to the compound having the following structural formula.
The electrophotographic photoreceptor of No. 1 was produced.

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Example 42 Example 4 was effected in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 31 was changed to the compound having the following structural formula.
No. 2 electrophotographic photosensitive member was produced.

[Chemical formula 126]

Example 43 Example 4 was effected in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 31 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 3 was produced.

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Example 44 Example 4 was conducted in the same manner as in Example 31 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 31 was changed to the compound having the following structural formula.
The electrophotographic photosensitive member of No. 4 was produced.

[Chemical 128]

Example 45 Example 4 was conducted in the same manner as in Example 31 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 31 was replaced by the compound having the following structural formula.
The electrophotographic photosensitive member of No. 5 was produced.

[Chemical formula 129]

Comparative Example 3 An electrophotographic photosensitive member of Comparative Example 3 was prepared in the same manner as in Example 31, except that the charge injection layer of Example 31 was not provided and the thickness of the charge transport layer was 25 μm. It was made.

Example 46 Electrophotographic photograph of Example 46 in the same manner as in Example 1 except that the polymer charge transporting substance in the coating liquid for charge transporting layer of Example 1 was changed to the compound of the following structural formula. A photoconductor was prepared.

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Example 47 Example 4 was effected in the same manner as in Example 46 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 46 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

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Example 48 Example 4 was effected in the same manner as in Example 46 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 46 was changed to the compound having the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

[Chemical 132]

Example 49 Example 4 was effected in the same manner as in Example 46 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 46 was changed to the compound having the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

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Example 50 Example 5 was repeated in the same manner as in Example 46 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 46 was a compound having the following structural formula.
No. 0 electrophotographic photosensitive member was produced.

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Example 51 Example 5 was effected in the same manner as in Example 46 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 46 was changed to the compound having the following structural formula.
The electrophotographic photoreceptor of No. 1 was produced.

[Chemical 135]

Example 52 Example 5 was carried out in the same manner as in Example 46 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 46 was a compound having the following structural formula.
No. 2 electrophotographic photosensitive member was produced.

[Chemical 136]

Example 53 Example 5 was effected in the same manner as in Example 46 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 46 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 3 was produced.

[Chemical 137]

Example 54 Example 5 was effected in the same manner as in Example 46 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 46 was changed to the compound of the following structural formula.
The electrophotographic photosensitive member of No. 4 was produced.

[Chemical 138]

Example 55 Example 5 was carried out in the same manner as in Example 46 except that the low molecular weight charge transporting substance added to the charge injection layer coating liquid of Example 46 was a compound having the following structural formula.
The electrophotographic photosensitive member of No. 5 was produced.

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Example 56 Example 5 was effected in the same manner as in Example 46 except that the low molecular charge transport substance added to the charge injection layer coating solution of Example 46 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 6 was produced.

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Example 57 Example 5 was effected in the same manner as in Example 46 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 46 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

[Chemical 141]

Example 58 Example 5 was effected in the same manner as in Example 46 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 46 was changed to the compound having the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

[Chemical 142]

Example 59 Example 5 was effected in the same manner as in Example 46 except that the low molecular charge transport substance added to the charge injection layer coating solution of Example 46 was changed to the compound having the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

[Chemical 143]

Example 60 Example 6 was conducted in the same manner as in Example 46 except that the low molecular charge transporting substance added to the coating liquid for the charge injection layer of Example 46 was changed to the compound having the following structural formula.
No. 0 electrophotographic photosensitive member was produced.

[Chemical 144]

[Comparative Example 4] Except that the charge injection layer of Example 46 is not provided and the thickness of the charge transport layer is set to 25 μm.
An electrophotographic photosensitive member of Comparative Example 4 was produced in the same manner as in Example 46.

Example 61 Electrophotograph of Example 61 in the same manner as in Example 1 except that the polymer charge transporting substance in the coating liquid for the charge transporting layer of Example 1 was a compound having the following structural formula. A photoconductor was prepared.

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Example 62 Example 6 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 61 was the compound having the following structural formula.
No. 2 electrophotographic photosensitive member was produced.

[Chemical 146]

Example 63 Example 6 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 61 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 3 was produced.

[Chemical 147]

Example 64 Example 6 was repeated in the same manner as in Example 61 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 61 was replaced by the compound having the following structural formula.
The electrophotographic photosensitive member of No. 4 was produced.

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Example 65 Example 6 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 61 was changed to the compound of the following structural formula.
The electrophotographic photosensitive member of No. 5 was produced.

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Example 66 Example 6 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 61 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 6 was produced.

[Chemical 150]

Example 67 Example 6 was effected in the same manner as in Example 61 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 61 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

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Example 68 Example 6 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 61 was changed to the compound having the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

[Chemical 152]

Example 69 Example 6 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 61 was replaced by the compound having the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

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Example 70 Example 7 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 61 was changed to the compound having the following structural formula.
No. 0 electrophotographic photosensitive member was produced.

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Example 71 Example 7 was carried out in the same manner as in Example 61 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 61 was the compound of the following structural formula.
The electrophotographic photoreceptor of No. 1 was produced.

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Example 72 Example 7 was effected in the same manner as in Example 61 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 61 was changed to the compound having the following structural formula.
No. 2 electrophotographic photosensitive member was produced.

[Chemical 156]

Example 73 Example 7 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 61 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 3 was produced.

[Chemical 157]

Example 74 Example 7 was conducted in the same manner as in Example 61 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 61 was changed to the compound having the following structural formula.
The electrophotographic photosensitive member of No. 4 was produced.

[Chemical 158]

Example 75 Example 7 was conducted in the same manner as in Example 61 except that the low molecular weight charge transporting substance added to the coating liquid for the charge injection layer of Example 61 was the compound having the following structural formula.
The electrophotographic photosensitive member of No. 5 was produced.

[Chemical 159]

Comparative Example 5 An electrophotographic photosensitive member of Comparative Example 5 was prepared in the same manner as in Example 61 except that the charge injection layer of Example 61 was not provided and the layer thickness of the charge transport layer was 25 μm. .

[Example 76] An electrophotographic photograph of Example 76 was conducted in the same manner as in Example 1 except that the polymer charge transporting substance in the coating liquid for the charge transporting layer of Example 1 was changed to the compound having the following structural formula. A photoconductor was prepared.

[Chemical 160]

Example 77 Example 7 was carried out in the same manner as in Example 76 except that the low molecular charge transporting substance added to the coating liquid for the charge injection layer of Example 76 was the compound of the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

[Chemical 161]

Example 78 Example 7 was conducted in the same manner as in Example 76 except that the low molecular charge transporting substance added to the coating liquid for the charge injection layer of Example 76 was changed to the compound having the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

[Chemical 162]

Example 79 Example 7 was conducted in the same manner as in Example 76 except that the low molecular charge transporting substance added to the coating liquid for the charge injection layer of Example 76 was changed to the compound of the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

[Chemical formula 163]

Example 80 Example 8 was effected in the same manner as in Example 76 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 76 was changed to the compound of the following structural formula.
No. 0 electrophotographic photosensitive member was produced.

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Example 81 Example 8 was carried out in the same manner as Example 76 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 76 was changed to the compound of the following structural formula.
The electrophotographic photoreceptor of No. 1 was produced.

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Example 82 Example 8 was carried out in the same manner as Example 76 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 76 was changed to the compound of the following structural formula.
No. 2 electrophotographic photosensitive member was produced.

[Chemical 166]

Example 83 Example 8 was carried out in the same manner as Example 76 except that the low molecular charge transporting substance added to the coating liquid for the charge injection layer of Example 76 was changed to the compound of the following structural formula.
The electrophotographic photoconductor of No. 3 was produced.

[Chemical 167]

Example 84 Example 8 was carried out in the same manner as Example 76 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 76 was changed to the compound of the following structural formula.
The electrophotographic photosensitive member of No. 4 was produced.

[Chemical 168]

Example 85 Example 8 was carried out in the same manner as Example 76 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 76 was changed to the compound of the following structural formula.
The electrophotographic photosensitive member of No. 5 was produced.

[Chemical 169]

Example 86 Example 8 was effected in the same manner as in Example 76 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 76 was changed to the compound of the following structural formula.
The electrophotographic photoconductor of No. 6 was produced.

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Example 87 Example 8 was effected in the same manner as in Example 76 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 76 was changed to the compound of the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

[Chemical 171]

Example 88 Example 8 was carried out in the same manner as Example 76 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 76 was changed to the compound of the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

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Example 89 Example 8 was carried out in the same manner as Example 76 except that the low molecular weight charge transporting substance added to the charge injection layer coating liquid of Example 76 was changed to the compound of the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

[Chemical 173]

Example 90 Example 9 was effected in the same manner as in Example 76 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 76 was changed to the compound having the following structural formula.
No. 0 electrophotographic photosensitive member was produced.

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[Comparative Example 6] Except that the charge injection layer of Example 76 is not provided and the thickness of the charge transport layer is 25 μm,
An electrophotographic photosensitive member of Comparative Example 6 was produced in the same manner as in Example 76.

Example 91 Electrophotograph of Example 91 in the same manner as in Example 1 except that the polymer charge transporting substance in the coating liquid for charge transporting layer of Example 1 was changed to the compound of the following structural formula. A photoconductor was prepared.

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Example 92 Example 9 was effected in the same manner as in Example 91 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound having the following structural formula.
No. 2 electrophotographic photosensitive member was produced.

[Chemical 176]

Example 93 Example 9 was effected in the same manner as Example 91 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 3 was produced.

[Chemical 177]

Example 94 Example 9 was effected in the same manner as in Example 91 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound having the following structural formula.
The electrophotographic photosensitive member of No. 4 was produced.

[Chemical 178]

Example 95 Example 9 was effected in the same manner as in Example 91 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound of the following structural formula.
The electrophotographic photosensitive member of No. 5 was produced.

[Chemical 179]

Example 96 Example 9 was effected in the same manner as in Example 91 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 6 was produced.

[Chemical 180]

Example 97 Example 9 was effected in the same manner as in Example 91 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound having the following structural formula.
The electrophotographic photoconductor of No. 7 was produced.

[Chemical 181]

Example 98 Example 9 was effected in the same manner as in Example 91 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound having the following structural formula.
No. 8 electrophotographic photosensitive member was produced.

[Chemical 182]

Example 99 Example 9 was effected in the same manner as in Example 91 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound having the following structural formula.
No. 9 electrophotographic photosensitive member was produced.

[Chemical 183]

Example 100 The procedure of Example 100 was repeated except that the low molecular charge transport material added to the charge injection layer coating solution of Example 91 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 101 The same procedure as in Example 101 was carried out except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 91 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 185]

Example 102 The procedure of Example 102 was repeated except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 91 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 186]

Example 103 Example 103 was repeated in the same manner as Example 91 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 91 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 187]

Example 104 The procedure of Example 104 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 91 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 188]

Example 105 The procedure of Example 105 was repeated except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 91 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 189]

Comparative Example 7 An electrophotographic photosensitive member of Comparative Example 7 was prepared in the same manner as in Example 91 except that the charge injection layer of Example 91 was not provided and the layer thickness of the charge transport layer was 25 μm. .

[Example 106] An electrophotographic photograph of Example 106 was carried out in the same manner as in Example 106 except that the polymer charge-transporting substance in the coating liquid for charge-transporting layer of Example 1 was changed to the compound of the following structural formula. A photoconductor was prepared.

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Example 107 The procedure of Example 107 was repeated except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 106 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 191]

Example 108 Example 108 was carried out in the same manner as in Example 108 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 106 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 192]

Example 109 Example 109 was repeated in the same manner as Example 106 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 106 was changed to the compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical formula 193]

Example 110 Example 110 was repeated in the same manner as in Example 106 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 106 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 111 Example 111 was repeated in the same manner as Example 106 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 106 was the compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 195]

Example 112 The procedure of Example 112 was repeated except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 106 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 196]

Example 113 The procedure of Example 113 was repeated except that the low molecular charge transport material added to the charge injection layer coating solution of Example 106 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 197]

Example 114 The procedure of Example 114 was repeated except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 106 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 115 The procedure of Example 115 was repeated except that the low-molecular-weight charge transporting substance added to the charge injection layer coating solution of Example 106 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical formula 199]

Example 116 The procedure of Example 116 was repeated except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 106 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

[Chemical 200]

Example 117 The procedure of Example 117 was repeated except that the low molecular charge transport material added to the charge injection layer coating solution of Example 106 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 118 Example 118 was carried out in the same manner as in Example 106 except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 106 was the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 119 The procedure of Example 119 was repeated except that the low molecular charge transport material added to the charge injection layer coating solution of Example 106 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 120 The procedure of Example 120 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 106 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Comparative Example 8 An electrophotographic photosensitive member of Comparative Example 8 was prepared in the same manner as in Example 106 except that the charge injection layer of Example 106 was not provided and the layer thickness of the charge transport layer was 25 μm. .

Example 121 Electrophotographic photograph of Example 121 in the same manner as in Example 121 except that the polymer charge transporting substance in the coating liquid for charge transporting layer of Example 1 was changed to the compound of the following structural formula. A photoconductor was prepared.

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Example 122 The procedure of Example 122 was repeated except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 121 was replaced by the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 123 Example 123 was repeated in the same manner as in Example 121 except that the low molecular weight charge transporting substance added to the charge injection layer coating liquid of Example 121 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 124 The procedure of Example 124 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 121 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 125 The procedure of Example 125 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 121 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 126 The procedure of Example 126 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 121 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 127 The procedure of Example 127 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 121 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 128 Example 128 was repeated in the same manner as Example 121 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 121 was replaced by the compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 129 The procedure of Example 129 was repeated in the same manner as in Example 121 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 121 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 130 Example 130 was repeated in the same manner as Example 121 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 121 was changed to the compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 131 Example 131 was repeated in the same manner as Example 121 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 121 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 132 The procedure of Example 132 was repeated except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 121 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 133 Example 133 was carried out in the same manner as Example 121 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 121 was the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 134 Example 134 was carried out in the same manner as Example 121 except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 121 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 135 The procedure of Example 135 was repeated except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 121 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Comparative Example 9 An electrophotographic photosensitive member of Comparative Example 9 was prepared in the same manner as in Example 121 except that the charge injection layer of Example 121 was not provided and the layer thickness of the charge transport layer was 25 μm. .

Example 136 Electrophotographic photograph of Example 136 in the same manner as in Example 136 except that the polymer charge transporting substance in the coating liquid for charge transporting layer of Example 1 was changed to the compound of the following structural formula. A photoconductor was prepared.

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Example 137 The procedure of Example 137 was repeated in the same manner as in Example 136 except that the low molecular charge transport material added to the charge injection layer coating solution of Example 136 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 138 The procedure of Example 138 was repeated in the same manner as in Example 136 except that the low molecular weight charge transporting substance added to the coating solution for the charge injection layer of Example 136 was the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 139 Example 139 was carried out in the same manner as in Example 136, except that the low molecular charge transporting substance added to the charge injection layer coating liquid of Example 136 was the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 140 Example 140 was repeated in the same manner as Example 136 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 136 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 141 The same procedure as in Example 141 was carried out except that the low-molecular-weight charge transport material added to the charge injection layer coating solution of Example 136 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 142 The procedure of Example 142 was repeated except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 136 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 143 The procedure of Example 143 was repeated in the same manner as in Example 136, except that the low molecular charge transporting substance added to the charge injection layer coating solution of Example 136 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 144 The procedure of Example 144 was repeated except that the low molecular weight charge transporting substance added to the coating solution for the charge injection layer of Example 136 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 145 The procedure of Example 145 was repeated except that the low molecular charge transport material added to the charge injection layer coating solution of Example 136 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 146 Example 146 was carried out in the same manner as in Example 136, except that the low molecular weight charge transporting substance added to the coating solution for the charge injection layer of Example 136 was the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 147 The procedure of Example 147 was repeated in the same manner as in Example 136 except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 136 was a compound having the following structural formula. An electrophotographic photoreceptor was produced.

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Example 148 The procedure of Example 148 was repeated except that the low molecular weight charge transporting substance added to the charge injection layer coating solution of Example 136 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 149 The procedure of Example 149 was repeated except that the low molecular charge transport material added to the charge injection layer coating solution of Example 136 was changed to the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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Example 150 Example 150 is carried out in the same manner as Example 136 except that the low molecular charge transporting substance added to the coating solution for the charge injection layer of Example 136 is the compound of the following structural formula. An electrophotographic photoreceptor was produced.

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[Comparative Example 10] Except that the charge injection layer of Example 136 is not provided and the layer thickness of the charge transport layer is set to 25 μm.
An electrophotographic photosensitive member of Comparative Example 10 was produced in the same manner as in Example 136.

The characteristics of the above photoreceptors were evaluated by the following procedure using an electrostatic copying paper tester (Model EPA-8100 manufactured by Kawaguchi Denki Seisakusho). First, -6 kV corona discharge was performed in a dark place for 20 seconds to charge it, and after leaving it in the dark for 20 seconds, the surface potential V ₀ (V) at this time was measured. Next, a tungsten lamp light is irradiated so that the illuminance on the surface of the photoconductor becomes 5.3 lux, and V ₀ becomes 1 /.
The time (sec) until 5 is reached, and the exposure charge E _1/5 (lu
x * sec) was calculated, and the surface potential V ₃₀ (V) 30 seconds after the light irradiation was also measured. The results are shown in Tables 27 to 36.

[0353]

[Table 27]

[0354]

[Table 28]

[0355]

[Table 29]

[0356]

[Table 30]

[0357]

[Table 31]

[0358]

[Table 32]

[0359]

[Table 33]

[0360]

[Table 34]

[0361]

[Table 35]

[0362]

[Table 36]

[0363]

As described above, according to the present invention, it is possible to improve the low sensitivity, which is a drawback common to electrophotographic photoreceptors using a polymer charge transporting material in the photosensitive layer, and to obtain high sensitivity,
An electrophotographic photoreceptor having a low residual potential can be obtained.

[Brief description of drawings]

FIG. 1 is an explanatory diagram showing a basic configuration of an electrophotographic photosensitive member of the present invention.

FIG. 2 is an explanatory view showing another constitution of the electrophotographic photosensitive member of the present invention.

FIG. 3 is an explanatory diagram showing still another configuration of the electrophotographic photosensitive member of the present invention.

[Explanation of symbols]

 11 Conductive Support 15 Intermediate Layer 17 Protective Layer 20 Photosensitive Layer 21 Charge Generation Layer 23 Charge Injection Layer 25 Charge Transport Layer

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Tetsuro Suzuki 1-3-6 Nakamagome, Ota-ku, Tokyo Stock company Ricoh Co., Ltd. (72) Inventor Eiichi Paper 1-3-6 Nakamagome, Tokyo Company Ricoh

Claims (21)

[Claims] 1. A laminated photoreceptor comprising at least a charge generation layer and a charge transport layer containing a polymer charge transport material represented by the following general formula (1) provided on a conductive support, An electrophotographic photoreceptor comprising a charge injection layer containing a low molecular weight charge transporting material as a main component between the charge transporting layers. Embedded image In the formula, R ₁ , R ₂ , and R ₃ are each independently a substituted or unsubstituted alkyl group or a halogen atom, R ₄ is a hydrogen atom, or a substituted or unsubstituted alkyl group, and R ₅ and R ₆ are substituted. Or an unsubstituted aryl group, o, p, and q are each independently an integer of 0 to 4, k and j represent the composition, 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 an aliphatic divalent group, a cyclic aliphatic divalent group, or a divalent group represented by the following general formula (1-1). Embedded image In the formula, R ₁₀₁ and R ₁₀₂ each independently represent a substituted or unsubstituted alkyl group, aryl group, or halogen atom.
l and m are integers of 0 to 4; Y is a single bond;
2, a linear, branched or cyclic alkylene group, -O
-, - S -, - SO -, - SO 2 -, - CO -, - CO
—O—Z—O—CO— (wherein Z represents an aliphatic divalent group), or a group represented by the following general formula (1-2): In the formula, a is an integer of 1 to 20, b is an integer of 1 to 2000,
R ₁₀₃ and R ₁₀₄ represent a substituted or unsubstituted alkyl group or aryl group. ) Represents. Where R ₁₀₁ and R ₁₀₂ ,
R ₁₀₃ and R ₁₀₄ may be the same or different. 2. A laminated photoreceptor comprising a conductive support and at least a charge generation layer and a charge transport layer containing a polymer charge transport substance represented by the following general formula (2), wherein the charge generation layer is provided. And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. Embedded image In the formula, R ₇ and R ₈ are substituted or unsubstituted aryl groups, A
r ₁ , Ar ₂ and Ar ₃ represent the same or different arylene groups. X, k, j and n are the same as in the case of the general formula (1). 3. A charge-generating layer comprising a conductive support and at least a charge-generating layer and a charge-transporting layer containing a polymer charge-transporting substance represented by the following general formula (3). And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. Embedded image In the formula, R ₉ and R ₁₀ are substituted or unsubstituted aryl groups,
Ar ₄ , Ar ₅ and Ar ₆ represent the same or different arylene groups. X, k, j and n are the same as in the case of the general formula (1). 4. A laminated photoreceptor comprising a conductive support, and at least a charge generation layer and a charge transport layer containing a polymer charge transport substance represented by the following general formula (4). And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. [Chemical 6] In the formula, R ₁₁ and R ₁₂ are substituted or unsubstituted aryl groups,
Ar ₇ , Ar ₈ and Ar ₉ are the same or different arylene groups,
p represents an integer of 1 to 5. X, k, j and n are the same as in the case of the general formula (1). 5. A laminated photoreceptor comprising a conductive support and at least a charge generation layer and a charge transport layer containing a polymer charge transport substance represented by the following general formula (5), wherein the charge generation layer is provided. And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. [Chemical 7] In the formula, R ₁₃ and R ₁₄ are substituted or unsubstituted aryl groups,
Ar ₁₀ , Ar ₁₁ and Ar ₁₂ represent the same or different arylene groups, and X ₁ and X ₂ represent a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group. X, k, j and n are the same as in the case of the general formula (1). 6. A laminated photoreceptor comprising a conductive support and at least a charge generation layer and a charge transport layer containing a polymer charge transport substance represented by the following general formula (6), wherein the charge generation layer is provided. And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. Embedded image In the formula, R ₁₅ , R ₁₆ , R ₁₇ , and R ₁₈ are substituted or unsubstituted aryl groups, Ar ₁₃ , Ar ₁₄ , Ar ₁₅ , and Ar ₁₆ are the same,
Or different arylene groups, Y ₁ , Y ₂ and Y ₃ are 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 They represent a vinylene group and may be the same or different. X, k, j and n
Is the same as in the case of the general formula (1). 7. A laminated photoreceptor comprising a conductive support and at least a charge generating layer and a charge transporting layer containing a polymer charge transporting material represented by the following general formula (7). And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. Embedded image In the formula, R ₁₉ and R _{20 each} represent a hydrogen atom or a substituted or unsubstituted aryl group, and R ₁₉ and R ₂₀ may form a ring. Ar ₁₇ , Ar ₁₈ and Ar ₁₉ represent the same or different arylene groups. X, k, j and n are represented by the general formula (1)
Is the same as 8. A laminated photoreceptor comprising a conductive support and at least a charge generating layer and a charge transporting layer containing a polymer charge transporting material represented by the following general formula (8). And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. Embedded image In the formula, R ₂₁ is a substituted or unsubstituted aryl group, A ₂₁
r ₂₀ , Ar ₂₁ , Ar ₂₂ , and Ar ₂₃ represent the same or different arylene groups. X, k, j and n are represented by the general formula (1)
Is the same as 9. A laminated photoreceptor comprising a conductive support and at least a charge generation layer and a charge transport layer containing a polymer charge transport substance represented by the following general formula (9), wherein the charge generation layer is provided. And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. Embedded image In the formula, R ₂₂ , R ₂₃ , R ₂₄ and R ₂₅ are substituted or unsubstituted aryl groups, Ar ₂₄ , Ar ₂₅ , Ar ₂₆ , Ar ₂₇ and Ar _28.
Represent the same or different arylene groups. X, k, j and n are the same as in the case of the general formula (1). 10. A laminate photoreceptor comprising a conductive support and at least a charge generation layer and a charge transport layer containing a polymer charge transport material represented by the following general formula (10), wherein the charge generation layer is provided. And an electric charge injection layer containing a low molecular weight electric charge transporting material as a main component between the electric charge transporting layer and the electric charge transporting layer. [Chemical 12] In the formula, R ₂₆ and R ₂₇ are substituted or unsubstituted aryl groups,
Ar ₂₉ , Ar ₃₀ , and Ar ₃₁ represent the same or different arylene groups. X, k, j and n are the same as in the case of the general formula (1). 11. The electrophotographic photosensitive member according to claim 1, wherein the low molecular weight charge transport material is a compound represented by the following general formula (11). . Embedded image In the formula, R ₂₀₁ , R ₂₀₂ , R ₂₀₃ , and R ₂₀₄ represent a hydrogen atom, a substituted or unsubstituted lower alkyl group, or a substituted or unsubstituted aryl group, and Ar ₁₀₁ represents a substituted or unsubstituted aryl group. , Ar ₁₀₂ represents a substituted or unsubstituted arylene group, Ar ₁₀₁ and R ₂₀₁ may together form a ring, and n ₁ is 0 or an integer of 1. 12. The electrophotographic photoreceptor according to claim 1, wherein the low-molecular-weight charge transport material is a compound represented by the following general formula (12). . Embedded image In the formula, R ₂₀₅ represents a lower alkyl group, a lower alkoxy group or a halogen atom, n ₂ represents an integer of 0 to 4,
₂₀₆ and R ₂₀₇ may be the same or different and each represents a hydrogen atom,
It represents a lower alkyl group, a lower alkoxy group, or a halogen atom. 13. The electrophotographic photosensitive member according to claim 1, wherein the low molecular weight charge transport material is a compound represented by the following general formula (13). . Embedded image In the formula, R ₂₀₈ represents an alkyl group having 1 to 11 carbon atoms, a substituted or unsubstituted phenyl group, or a heterocyclic residue, and R _208
209 and R ₂₁₀ may be the same or different and include a hydrogen atom,
A lower alkyl group, a hydroxyalkyl group having 1 to 4 carbon atoms, a chloroalkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aralkyl group, and R ₂₀₉ and R ₂₁₀ jointly contain a nitrogen-containing compound ring R ₂₁₁ , R ₂₁₂
May be the same or different and each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom. 14. The electrophotographic photoreceptor according to claim 1, wherein the low-molecular weight charge transport material is a compound represented by the following general formula (14). . Embedded image In the formula, R ₂₁₃ represents a hydrogen atom or a halogen atom, and R _213
214 is a substituted or unsubstituted aromatic residue, or a heterocyclic residue (provided that the substituent is a halogen atom, a cyano group, a di-lower alkylamino group, a substituted or unsubstituted diaralkylamino group, a lower alkyl group, It is either a lower alkoxy group or a nitro group). 15. The electrophotographic photosensitive member according to claim 1, wherein the low molecular weight charge transporting substance is a compound represented by the following general formula (15). . Embedded image In the formula, R ₂₁₅ , R ₂₁₆ , and R ₂₁₇ each represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a heterocyclic group, and at least two of R ₂₁₅ , R ₂₁₆ , and R ₂₁₇ are represented. Represents an aryl group or a heterocyclic group. 16. The electrophotographic photosensitive member according to claim 1, wherein the low-molecular-weight charge transport material is a compound represented by the following general formula (16). . Embedded image In the formula, Ar ₁₀₃ and Ar ₁₀₄ each represent a substituted or unsubstituted aryl group or a heteroaromatic ring. 17. The electrophotographic photosensitive member according to claim 1, wherein the low molecular weight charge transport material is a compound represented by the following general formula (17). . Embedded image In the formula, Ar ₁₀₅ represents a substituted or unsubstituted aryl group or a heteroaromatic ring, and R ₂₁₈ and R ₂₁₉ are a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a heterocyclic group, respectively. , R ₂₁₈ , and R ₂₁₉ are at least one of an aryl group or a heterocyclic group. 18. The electrophotographic photosensitive member according to claim 1, wherein the low molecular weight charge transport material is a compound represented by the following general formula (18). . Embedded image In the formula, R ₂₂₀ and R ₂₂₂ represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a di-lower alkylamino group, and R _220
221 is a hydrogen atom, a lower alkyl group, a lower alkoxy group,
Represents a halogen atom or a nitro group, n ₃ is 0 or 1
Represents the integer. 19. The electrophotographic photoreceptor according to claim 1, wherein the low-molecular weight charge transport material is a compound represented by the following general formula (19). . [Chemical 21] In the formula, R ₂₂₃ is a carbazolyl group, a pyridyl group, a thienyl group, an indolyl group, a furyl group, or a substituted or unsubstituted phenyl group, a styryl group, a naphthyl group,
Or an anthryl group (provided that the substituent is any one of a di-lower alkylamino group, a lower alkyl group, a lower alkoxy group, a halogen atom, an aralkylamino group, and an amino group). 20. The electrophotographic photoreceptor according to claim 1, wherein the low-molecular weight charge transport material is a compound represented by the following general formula (20). . Embedded image In the formula, Ar ₁₀₆ represents a substituted or unsubstituted biphenylene group, R ₂₂₄ , R ₂₂₅ , and R ₂₂₆ represent a hydrogen atom, a halogen atom, a cyano group, or an optionally substituted alkyl group, an alkoxy group, It represents an aryloxy group, an alkylmercapto group, a methylenedioxy group, a methylenedithio group, or an aryl group, and R ₂₂₄ , R ₂₂₅ , and R ₂₂₆ may be the same or different. U, v, and w each represent an integer of 1 to 5, and when each is an integer of 2 to 5, R ₂₂₄ and R
₂₂₅ and R ₂₂₆ may be the same or different. 21. The electrophotographic photosensitive member according to claim 1, wherein the low molecular weight charge transport material is a compound represented by the following general formula (20). . Embedded image In the formula, R ₂₂₇ and R ₂₂₈ represent a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, and R _227
At least one of ₂₂₇ and R ₂₂₈ represents a substituted or unsubstituted aryl group.