JPH11149167A - Electrophotographic photoreceptor and its manufacture - Google Patents

Abstract

PROBLEM TO BE SOLVED: To enable the repeating uses of the electrophotographic photoreceptor for a long term without occurrence of abrasion and scratches and coating film defects on the surface of the photoreceptor by incorporating a specified polycarbonate copolymer and a specified compound. SOLUTION: The photosensitive layer formed on the conductive substrate of the photoreceptor contains the polycarbonate copolymer composed essentially of structural units represented by formulae I and II and the compound represented by formula III. In formulae I-II, each of R1 -R6 is a 1-6C alkyl group; each of (l), (m), (p), and (q) is an integer of 1-4; Ar is an optionally substituted aryl group or the like; and (n) is 2, 3, or 4. This electrophotographic photoreceptor is formed by dip coating a cylindrical conductive substrate with that.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an electrophotographic photosensitive member, and more particularly, to an organic photoconductive electrophotographic photosensitive member and a method for producing an electrophotographic photosensitive member constituting layer.

[0002]

2. Description of the Related Art There are various systems in an electrophotographic process, and a direct system and a latent image transfer system are known as typical examples. In the electrophotographic photoreceptor used in these electrophotographic processes, basic properties required as a photoconductive layer material constituting the photoconductive layer include: 1) chargeability of a charge by corona discharge in a dark place. 2) The charge due to the obtained corona discharge is small in a dark place. 3) The charge is quickly dissipated by light irradiation. 4) The residual charge after light irradiation is small. 5) Repeated use. And 6) a small change in electrophotographic characteristics due to temperature and humidity, and the like.

As such materials, inorganic photoconductive materials such as zinc oxide (Japanese Patent Publication No. 57-19780), cadmium sulfide (Japanese Patent Publication No. 58-46018), and amorphous selenium alloy have been conventionally used. Although it has been used, various problems have been pointed out in recent years. That is, in the case of a zinc oxide-based material, the sensitizer causes charge deterioration due to corona discharge and photobleaching due to exposure, so that a stable image cannot be provided over a long period of time. In a cadmium sulfide-based material, stable sensitivity cannot be obtained under humid conditions. The selenium-based material has thermal stability, deterioration of characteristics due to crystallization, difficulty in production, and the like.

[0004] From a future perspective, electrophotography made of an organic material rather than an inorganic material, which has production problems due to resource depletion, concerns about pollution due to toxicity, and environmental problems. Photoconductors have been actively developed, and as a result, electrophotographic photoconductors using various organic compounds have been studied. In particular, research and development in recent years have tended to actively introduce the concept of a function-separated type photoreceptor, and in particular, a charge generation layer and a hole-transport charge-transport layer on a conductive layer. Are stacked in order, and the charge transfer surface is negatively charged.

[0005] By separating the functions in this manner, it becomes possible to independently develop materials having the functions of charge generation and charge transfer independently. As a result, charges having various molecular structures can be obtained. Many generators and charge transfer materials have been developed. Here, paying attention to the charge transfer materials, a typical one of them is classified according to structural characteristics.
3), stilbene-styryl type (JP-A-58-1980)
43), triarylamines (JP-B-58-3237)
2), phenothiazines, triazoles, quinoxalines, oxadiazoles, oxazoles, pyrazolines, triphenylmethanes, dihydronicotinamide compounds, indoline compounds, semicarbazone compounds, and the like have been developed.

However, despite the fact that many organic compounds have been developed as charge transfer materials, 1) low compatibility with the binder resin, 2) easy precipitation of crystals, 3) repeated use 4) Poor chargeability and repetition characteristics, 5) Poor residual potential characteristics, etc. At present, it is not yet possible to obtain a material satisfying the properties, mechanical strength, high durability, and the like, and there is a strong demand for the development of a more excellent organic photoconductive material and photoreceptor.

Until now, these function-separated type organic photoreceptors have a structure in which a thin charge generation layer is provided on a conductive support, mainly for negative charging, and a charge transport layer of an appropriate thickness is formed thereon. Has been taken. Further, as a binder resin used in such an organic photoreceptor, a conventional bisphenol A-type polycarbonate may exhibit appropriate characteristics in various electrophotographic characteristics (sensitivity, chargeability, residual potential, repetition characteristics, etc.). Generally known. However, in recent years, the use of bisphenol A-type polycarbonate resin has led to the following problems.

[0008] 1) When a solution having high crystallinity of a polymer is formed into a solution, it causes a gelling phenomenon and becomes unusable immediately. 2) At the time of forming a film by coating, a highly crystalline polycarbonate precipitates on the film surface. 3) The surface of the photosensitive layer is apt to be scratched. 4) The photosensitive layer gradually wears with an increase in the number of copies. Do

Therefore, in order to solve such problems, various methods, for example, a method of introducing various substituents into a monomer unit of bisphenol A (JP-A-60-1)
72045, JP-A-63-65444, JP-A-63-65444
However, as the speed of the copying machine has increased, the process speed has increased, the scattering of toner has increased, and cleaning failure has been more likely to occur. As a countermeasure, some models use two-stage cleaning blades or increase the pressure. However, at present, such improvement alone does not provide a sufficient measure because of large wear. In addition, some methods of providing an overcoat layer have been proposed, but in production by coating, it is difficult to select a solvent that does not dissolve the already applied photosensitive layer, and even when completed, the electrical properties are adversely affected. Its design is difficult. Furthermore, a method using two or more kinds of polycarbonate resins having different molecular weights, or a specific polycarbonate copolymer (JP-A-4-179996)
1) and a method of combining this with a specific charge transport material (Japanese Patent Application Laid-Open No. 6-83081) have been proposed, but none of them can provide sufficient performance.

As described above, the organic photoreceptor does not yet have sufficient surface strength and surface smoothness, is easily scratched, deteriorates in image quality due to repeated use, and decreases in sensitivity as the film thickness decreases due to abrasion. Problems remain unsolved.

[0011]

SUMMARY OF THE INVENTION The object of the present invention is to solve the above-mentioned problems, and is to provide a highly sensitive and uniform coating film which is in contact with toner, developer, paper, cleaning blade, etc. It can be used repeatedly over a long period of time without causing abrasion of the photoreceptor surface, scratches or coating film defects, high mechanical durability of the photosensitive layer, good surface smoothness, low image quality, and low sensitivity degradation An object of the present invention is to provide an electrophotographic photosensitive member. Still another object of the present invention is to provide a method for producing an electrophotographic photoreceptor having a uniform film thickness and having no coating film defects when a photosensitive layer is produced by a dip coating method.

[0012]

Means for Solving the Problems The present inventors have developed a photoreceptor which has the above-mentioned object of high sensitivity, high mechanical durability of the electrophotographic photosensitive layer, good flatness in flatness, low image quality and low sensitivity deterioration. And a polycarbonate having a structural unit represented by the following general formula (I) and a structural unit represented by the following general formula (II) as main components in a photosensitive layer formed on a conductive support. It contains a copolymer resin and has the following general formula (II
The inventors have found that an electrophotographic photosensitive member characterized by containing the compound represented by (I), (IV) or (V) is effective, and have completed the present invention.

[0013]

Embedded image

[In the formula, R ₁ and R ₂ each represent an alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, An aryl group which may have a group or a hydrogen atom, and R ₃ , R ₄
Is an alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, an aryl group which may have a substituent, and a halogen atom Or a hydrogen atom, and l and m each represent 1-4
Represents an integer. R ₁ and R ₂ may be bonded to each other to form a hydrocarbon ring. ]

[0015]

Embedded image

[In the formula, R ₅ and R ₆ are an alkyl group having 1 to 6 carbon atoms which may have a substituent, a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, Represents an aryl group which may have a group, a halogen atom or a hydrogen atom, and p and q each represent an integer of 1 to 4. ]

[0017]

Embedded image

[In the formula, Ar represents an aryl group which may have a substituent, a heterocyclic group which may have a substituent, an aralkyl group which may have a substituent, or a heterocyclic-substituted alkyl group. , N represents an integer of 2 to 4. ]

[0019]

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[Wherein, R ₇ and R ₈ may be the same or different and are a lower alkyl group, a cycloalkyl group optionally having a substituent, an aryl group optionally having a substituent, aralkyl group which may have a group, represent an optionally substituted heterocyclic group or heterocyclic-substituted alkyl group and R ₇
And R ₈ may form a nitrogen-containing heterocyclic group together with the nitrogen atom to which they are bonded. R ₉ , R ₁₀ , R ₁₁ and R ₁₂ may be the same or different and represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower halogenated alkyl group, a lower alkoxy group or a lower dialkylamino group; Represents an integer of from 4 to 4. ]

[0021]

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[Wherein R ₁₃ and R ₁₄ are hydrogen atoms (provided that R
₁₃ and R ₁₄ are both hydrogen atoms), an aryl group which may have a substituent, a heterocyclic group which may have a substituent,
A represents an aralkyl group, a lower alkyl group or a heterocyclic substituted alkyl group which may have a substituent, a represents a lower alkyl group, a lower halogenated alkyl group, a lower alkoxy group, a halogen atom or a hydrogen atom, and j represents 1 Represents an integer of 4 to 4 (however, when j is 2 or more, a may be the same or different), and k represents an integer of 2 to 4. ]

In the present invention, the general formula (I) is preferably the following structural unit (a), and the general formula (II) is preferably the following structural unit (b). General formula (I) is the following structural unit (a),
Further, it is preferable that the general formula (II) is the following structural unit (b).

[0024]

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In the present invention, the viscosity average molecular weight of the polycarbonate copolymer resin represented by the general formulas (I) and (II) is preferably from 20,000 to 80,000.
The electrophotographic photoreceptor of the present invention is manufactured by dip-coating a photosensitive layer on a cylindrical conductive support, and the concentration of the polycarbonate copolymer resin in the coating solution is adjusted to 8% by weight or more and 13% by weight or less. .

In the present invention, by using a copolymer containing the above general formulas (I) and (II) as structural units as main repeating units as a binder resin for an electrophotographic photosensitive member, electrophotographic properties (sensitivity, sensitivity, It is possible to provide an electrophotographic photoreceptor that is excellent in chargeability, residual potential, repetition characteristics, etc., has little fatigue deterioration even when used repeatedly, and has stable characteristics excellent in mechanical durability.

[0027]

Embodiments of the present invention will be described below in detail. The electrophotographic photoreceptor of the present invention has a structure in which a structural unit represented by the general formula (I) and a structure represented by the general formula (II) are used as a binder resin in a photosensitive layer formed on a conductive support. It is characterized by containing a polycarbonate copolymer resin having a unit as a main component and containing any one of the compounds represented by formulas (III), (IV) and (V) as a charge transporting material. It is assumed that. ,

The copolymer in the present invention can be easily synthesized by a general synthesis route using bisphenol-based compounds represented by the following general formulas (I ′) and (II ′).

[0029]

Embedded image

[Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ ,
l, m, p, and q have the same meanings as those in formulas (I) and (II). ]

As a specific synthetic route, an inert halogenated hydrocarbon such as dichloromethane or 1,2-dichloroethane is used as a reaction solvent, and the above-mentioned general formulas (I ′) and (II ′) are used.
The reaction is carried out while passing phosgene gas to the bisphenol-based compound represented by the formula (1), and an aqueous alkaline solution or an organic amine compound such as pyridine is used as an acid trapping agent for hydrogen chloride gas produced as the reaction proceeds. Here, when an alkaline aqueous solution is used as the acid trapping agent,
Trialkylamines (trimethylamine,
When a tertiary amine such as triethylamine or diisopropylethylamine) or a quaternary ammonium salt such as tetraalkylammonium halide (tetraethylammonium chloride or tributylbenzylammonium bromide) is used in combination, the reactivity increases.

Further, if necessary for the purpose of controlling the molecular weight of the copolymer in the present invention, a monovalent phenol derivative (for example, phenol, pt-butylphenol, pn
-Butylphenol) may be used. At this time, the monohydric phenol derivative may be added from the beginning of the reaction, or may be added to the reaction to a certain extent, and an oligomer may be prepared and then added to the mixture to increase the molecular weight. There is. Further, when the copolymer in the present invention is copolymerized with two or more kinds of bisphenol-based compounds, it is simultaneously reacted with phosgene from the beginning to carry out copolymerization. There are various methods, such as adding the remaining one at the advanced stage to carry out copolymerization, independently reacting each with phosgene in advance, and performing polymerization later.

In the general formula (I), R ₁ and R ₂ are specifically lower alkyl groups such as methyl, ethyl and n-propyl, aryl groups such as phenyl, p-tolyl and m-tolyl, cyclohexyl, Examples thereof include a cycloalkyl group such as cyclopentyl, and a hydrogen atom. R ₃ and R ₄ are specifically lower alkyl groups such as methyl, ethyl and n-propyl, cycloalkyl groups such as cyclohexyl, aryl groups such as phenyl, p-tolyl and m-tolyl, fluorine, chlorine, bromine and the like. Halogen atom, hydrogen atom and the like. In the general formula (II), R ₅ and R ₆ are specifically lower alkyl groups such as methyl, ethyl and n-propyl; cycloalkyl groups such as cyclohexyl; aryl groups such as phenyl, p-tolyl and m-tolyl. And halogen atoms such as fluorine, chlorine and bromine, and hydrogen atoms.

Next, specific examples of the structural units represented by the general formulas (I) and (II) are shown in Tables 1 and 2, but the copolymer of the present invention is not limited by these.

[0035]

Embedded image

[0036]

[Table 1]

[0037]

[Table 2]

In the present invention, the general formula (I) is preferably the structural unit (a) (exemplary compound NoI-1), and the general formula (II) is preferably the structural unit (b) (exemplary compound No. 1). NoII-1), and more preferably, the general formula (I) is the structural unit (a), and the general formula (II) is the structural unit (b).

Examples of the copolymer having each of the structural units represented by the general formulas (I) and (II) include those having the structures shown in Table 3. Coalescence is not limited at all.

[0040]

[Table 3]

The polymerization molar ratio of s: t is 95: 5-
The ratio is preferably in the range of 5:95, more preferably in the range of 95: 5 to 50:50. If the polymerization molar ratio of the general formula (II) exceeds 95%, the sensitivity of the electrophotographic photoreceptor will be reduced, and if it is less than 1%, the properties as a copolymer will not be sufficiently exhibited.

The degree of polymerization of the copolymer is 10 to 5000,
Preferably it is 50-1000. If the degree of polymerization is lower than this, sufficient surface strength cannot be obtained as a binder, resulting in poor mechanical durability. Also, if the degree of polymerization is too large, very excellent properties as mechanical durability can be obtained, but it becomes difficult to dissolve in the organic solvent used when manufacturing the photoreceptor, and the viscosity of the coating solution increases. As a result, the uniformity of the film thickness of the photoreceptor, the surface smoothness, and the compatibility with the charge transport material are deteriorated, and image defects occur.

The viscosity average molecular weight of the copolymer is from 20,000 to
It is desirably 80,000, preferably 30,000 to 50,000.
If it is less than 30,000, the solution viscosity is insufficient, and if it exceeds 50,000, the solution viscosity is too high, and in any case, the condition setting at the time of drumming becomes severe.

In the present invention, if necessary, other binder resins may be used in a proportion that does not adversely affect the properties of the intended electrophotographic photoreceptor. The following resins can be mentioned. PVC,
Polyvinylidene chloride, polyvinyl acetate, polyvinyl butyral, polyvinyl formal, polystyrene,
Polyester, polyhydroxystyrene, methacrylic resin, acrylic resin, phenolic resin (eg, cresol-formaldehyde resin), styrene copolymer resin (eg, styrene-butadiene copolymer), acrylonitrile copolymer resin (eg, vinylidene chloride-acrylonitrile copolymer) And vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer, silicone resin, silicone alkyd resin and the like. These binder resins can be used alone or
Even as a mixture of more than one kind, it can be used in combination with the polycarbonate copolymer resin of the present invention, but in order to sufficiently exhibit the properties of the binder resin of the present invention, the mixing ratio of the other binder resin is not limited to the binder used. The content is preferably not more than 50% by weight of the resin. Because 5
If the content exceeds 0% by weight, the properties of the binder resin used in combination will be emphasized and the meaning of the original invention will be lost.

Next, the charge transporting materials represented by the general formulas (III) to (V) will be described.

Embedded image

In the general formula (III), Ar represents an aryl group which may have a substituent, a heterocyclic group which may have a substituent, an aralkyl group which may have a substituent, or a heterocyclic-substituted alkyl. Group. Specifically, aryl such as phenyl, tolyl, methoxyphenyl, ethoxyphenyl, isopropylphenyl, fluorophenyl, trifluoromethylphenyl, dimethylaminophenyl, naphthyl, methylnaphthyl, biphenyl, methylbiphenyl, methoxybiphenyl, anthryl, tetralinyl and indanyl Group, pyridyl, pyrimidyl, benzothiofuranyl,
Fluorenonyl, acridinyl, 2,1,3-benzothiadiazolyl, 2-benzothiadiazolyl, 6-methoxy-2-benzothiadiazolyl, 2-benzoxazolyl, 2-methyl-5-benzoxazolyl Heterocyclic groups such as 4-phenyl-2-thiazolyl, 5-ethyl-2-1,3,4-thiadiazolyl and 5-methyl-3-isoxazolyl; aralkyl groups such as benzyl, methoxybenzyl and methylbenzyl; thienylmethyl And the like, but an aryl group unsubstituted or substituted with an electron donating group is more effective.

Particularly preferred are phenyl, p-methoxyphenyl, m-methoxyphenyl, p-ethoxyphenyl, m-ethoxyphenyl, p-tolyl, m-tolyl,
m-methylphenyl, m-isopropylphenyl, 3,
5-xylyl, m-chlorophenyl, 1-naphthyl, m
Aryl groups such as -dimethylaminophenyl; and heterocyclic groups such as 2-pyridyl, 6-methoxy-2-benzothiazolyl and 2-methyl-5-benzoxazolyl.

Next, specific examples of the charge transporting material represented by the general formula (III) are shown in Table 4, but the present invention is not limited thereto.

[0049]

[Table 4]

[0050]

[Table 5]

[0051]

[Table 6]

[0052]

[Table 7]

[0053]

[Table 8]

[0054]

[Table 9]

[0055]

[Table 10]

[0056]

[Table 11]

[0057]

[Table 12]

[0058]

[Table 13]

[0059]

[Table 14]

[0060]

[Table 15]

[0061]

[Table 16]

[0062]

[Table 17]

[0063]

[Table 18]

Among these exemplified compounds, those which are particularly excellent in electrophotographic properties, cost and synthesis are Nos. 1, 2 and
3, 4, 7, 11, 15, 16, 22, 26, 28, 4
2, 56, 57, 58, 59, 63, 67, 78, 8
2, 91, 92, 93, 94, 96 and 97.

[0065]

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In the general formula (IV), R ₇ and R ₈ may be the same or different, and may be a lower alkyl group, a cycloalkyl group which may have a substituent, or an aryl which may have a substituent. R ₇ and R ₈ represent a group, an aralkyl group which may have a substituent, a heterocyclic group which may have a substituent, or a heterocyclic substituted alkyl group; A heterocyclic group may be formed. R ₉ , R ₁₀ ,
R ₁₁ and R ₁₂ may be the same or different, and represent a hydrogen atom,
Represents a halogen atom, a lower alkyl group, a lower halogenated alkyl group, a lower alkoxy group or a lower dialkylamino group, and r represents an integer of 2 to 4.

Specific examples of the lower alkyl group as R ₇ and R ₈ include methyl, ethyl, n-propyl, iso-
Propyl, n-butyl, sec-butyl, n-pentyl group and the like. Aryl groups include phenyl, 1
-Naphthyl, 9-anthraceryl group and the like. In these aryl groups, at least one of the hydrogen atoms may be substituted with methyl, methoxy, halogen, or the like.
Examples include p-tolyl, 3,5-xylyl, p-tolyl
Methoxyphenyl, p-chlorophenyl, 2-methyl-
1-naphthyl and the like. Examples of the aralkyl group include a benzyl group and a phenylethyl group, and those having these substituents include, for example, p-methoxybenzyl, p-methylbenzyl, p-chlorobenzyl and the like.

The heterocyclic group includes 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl,
There are benzothiazoyl and 2-benzoxazolyl groups, and those having these substituents are also mentioned. Examples of the heterocyclic-substituted alkyl group include 2-thienylmethyl, 3
-Thienylmethyl, 2-furylmethyl, 3-furylmethyl, 2-pyridylmethyl, 2-benzothiazoylmethyl, 2-benzozoazoylmethyl, and the like, and those further having a substituent thereof. Among these, 2-thienylmethyl and 3-thienylmethyl groups are preferred.

The nitrogen-containing heterocyclic group formed together with the nitrogen atom to which R ₇ and R ₈ are bonded includes

Embedded image And the like.

R ₇ and R ₈ preferably form a lower alkyl group or an aryl group, or a nitrogen-containing heterocyclic group together with the nitrogen atom to which R ₇ and R ₈ are bonded, among the groups shown above. . The lower alkyl group is particularly preferably a methyl group. The aryl group is particularly preferably a phenyl group. Nitrogen-containing heterocyclic groups are particularly

[0071]

Embedded image Is preferred.

Further, those having these substituents include, for example,

Embedded image Are also preferred.

R ₉ , R ₁₀ , R ₁₁ and R ₁₂ may be the same or different and include a hydrogen atom, a halogen atom, a lower alkyl group, a lower halogenated alkyl group, a lower alkoxy group or a lower dialkylamino group. However, a hydrogen atom or an electron donating substituent is preferable. Examples of the electron-donating substituent include a methyl group, an ethyl group, a propyl group, a methoxy group, and a dimethylamino group. Among them, an enamine derivative in which a hydrogen atom or any one of them is a lower alkyl group is preferable.

Next, specific examples of the charge transporting material represented by the general formula (IV) are shown in Table 5, but the present invention is not limited thereto.

[0075]

[Table 19]

[0076]

[Table 20]

[0077]

[Table 21]

[0078]

[Table 22]

[0079]

[Table 23]

[0080]

[Table 24]

[0081]

[Table 25]

[0082]

[Table 26]

[0083]

[Table 27]

[0084]

[Table 28]

[0085]

[Table 29]

[0086]

[Table 30]

[0087]

[Table 31]

[0088]

[Table 32]

[0089]

[Table 33]

[0090]

[Table 34]

Among the exemplified compounds represented by the general formula (IV), those which are particularly excellent in electrophotographic properties, cost and synthesis are those in which one of R ₇ and R ₈ is a phenyl group or p-methoxyphenyl. And a p-tolyl group, one of which is a hydrogen atom.

[0092]

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In the general formula (V), R ₁₃ and R ₁₄ represent a hydrogen atom (however, unless R ₁₃ and R ₁₄ are both hydrogen atoms), an aryl group which may have a substituent, and a substituent. Represents a heterocyclic group which may have, an aralkyl group which may have a substituent, a lower alkyl group or a heterocyclic substituted alkyl group, a represents a lower alkyl group, a lower halogenated alkyl group,
Represents a lower alkoxy group, a halogen atom or a hydrogen atom, j is an integer of 1 to 4 (however, when j is 2 or more, a may be the same or different), and k is an integer of 2 to 4 is there.

Specific examples of R ₁₃ and R ₁₄ include methyl, ethyl, n-propyl, iso-propyl, n-butyl,
sec-butyl, lower alkyl groups such as n-pentyl group,
Aryl groups such as phenyl, p-tolyl, 3,5-xylyl, p-methoxyphenyl, p-chlorophenyl, 1-naphthyl, 2-furyl, 3-furyl, 2-thienyl,
Examples include a heterocyclic group such as 1-benzothiazole and 1-benzoxazole, and an aralkyl group such as benzyl, p-methoxybenzyl, p-methylbenzyl, and p-chlorobenzyl.

Next, specific examples of the charge transporting material represented by the general formula (V) are shown in Table 6, but the present invention is not limited thereto.

[0096]

[Table 35]

[0097]

[Table 36]

[0098]

[Table 37]

[0099]

[Table 38]

[0100]

[Table 39]

[0101]

[Table 40]

[0102]

[Table 41]

[0103]

[Table 42]

[0104]

[Table 43]

[0105]

[Table 44]

[0106]

[Table 45]

[0107]

[Table 46]

Among the exemplified compounds represented by the general formula (V), those excellent in cost and synthesis are those in which one of R ₁₃ and R ₁₄ is a phenyl group or a p-tolyl group,
Compounds in which one is a methyl group, an ethyl group, or a phenyl group are exemplified.

If necessary, other charge transporting materials such as 4- (dibenzylamino) benzaldehyde-N,
N-diphenylhydrazone, 4- (ethylphenylamino) benzaldehyde-N, N-diphenylhydrazone, 4-di (p-tolylamino) benzaldehyde-
N, N-diphenylhydrazone, 3,3-bis- (4 ′
-Diethylaminophenyl) -acrolein-N, N-
Diphenylhydrazone, triphenylamine compound (for example, 4-methoxy-4 '-(4-methoxystyryl)
Triphenylamine, 4-methoxy-4'-styryltriphenylamine) and the like.

The electrophotographic photoreceptor according to the present invention is obtained by containing one or more of the above-described polycarbonate copolymer and a charge transport material, and as a result, has extremely high performance. There are various methods for using the polycarbonate copolymer and the charge transport material as an electrophotographic photosensitive member. For example, the charge transport material and sensitizing dye of the present invention, if necessary with the addition of a chemical sensitizer or an electron-withdrawing compound, are dissolved or dispersed in the polycarbonate copolymer of the present invention to form a conductive support. In the form of a photoreceptor provided on the body, or in the form of a laminated structure comprising a charge generation layer and a charge transfer layer having high charge generation efficiency, a sensitizing dye or an azo pigment on a conductive support,
The charge transport material of the present invention on the charge generation layer provided mainly with pigments such as phthalocyanine pigments,
If necessary, an antioxidant compound, an electron-withdrawing compound or the like may be added and dissolved or dispersed in the polycarbonate copolymer of the present invention. At that time, the amount of the polycarbonate copolymer of the present invention to be added to the charge transporting material of the present invention is 0.2 to 20 times by weight, preferably 0.1 to 0.2.
The range is 5 to 5 times. If the ratio is less than 0.2, the charge transporting material precipitates from the surface of the photoreceptor. If the ratio is 5 times or more, the sensitivity is remarkably lowered, which is not preferable.

To prepare a photoreceptor using the compound of the present invention, the photoreceptor is coated on a conductive support such as a metal drum, a metal plate, a paper which has been subjected to conductive processing, or a plastic film. To form Next, as a sensitizing dye added to the photosensitive layer, methyl violet, crystal violet, night blue, triphenylmethane dyes represented by Victoria blue, etc., erythrosine,
Rhodamine B, rhodamine 3R, acridine orange,
Acridine dyes such as flapeosin, thiazine dyes such as methylene blue and methylene green, oxazine dyes such as capri blue and Meldora blue, and other cyanine dyes, styryl dyes, pyrylium salt dyes, and thiopyrylium salt dyes There is.

Examples of photoconductive pigments that generate charges at extremely high efficiency by light absorption in the photosensitive layer include various metal phthalocyanines, metal-free phthalocyanines,
Examples include phthalocyanine pigments such as halogenated metal-free phthalocyanines, perylene acid pigments such as perylene imide and perylene anhydride, azo pigments such as bisazo pigments and trisazo pigments, and other quinacridone pigments and anthraquinone pigments. In particular, those using a metal-free phthalocyanine pigment, a titanyl phthalocyanine pigment, a fluorene, a bisazo pigment containing a fluorenone ring, a bisazo pigment composed of an aromatic amine, and a trisazo pigment as the pigment that generates electric charge show excellent sensitivity and high electron sensitivity. Give a photoreceptor.
Further, the above-mentioned dye may be used as the charge generating substance.
These dyes may be used alone, but charge carriers are often generated with higher efficiency by coexisting a pigment.

In addition to the sensitizers mentioned above, it is necessary to add various chemical substances for the purpose of preventing an increase in the residual potential, a decrease in the charged potential, a decrease in the sensitivity and the like upon repeated use. It is becoming. These added substances include
-Chloranthraquinone, benzoquinone, 2,3-dichloronaphthoquinone, naphthoquinone, 4,4'-dinitrobenzophenone, 4,4'-dichlorobenzophenone,
4-nitrobenzophenone, 4-nitrobenzalmalone dinitrile, α-cyano-β- (p-cyanophenyl)
Ethyl acrylate, 9-anthracenylmethylmalondinitrile, 1-cyano-1- (p-nitrophenyl)-
Electron-withdrawing compounds such as 2- (p-chlorophenyl) ethylene and 2,7-dinitrofluorenone; In addition, an antioxidant, an anti-curl agent, a leveling agent, and the like can be added as necessary to the photoreceptor.

The polycarbonate copolymer and the charge transporting material of the present invention are dissolved or dispersed in an appropriate solvent together with various additives as described above according to the form of the photoreceptor, and the coating solution is described above. It is coated on a conductive support and dried to produce a photoreceptor. At that time, the mainstream is to use a metal drum for the conductive support in consideration of productivity and cost, and dip-coat in a coating solution in which the material constituting the photosensitive layer is dissolved or dispersed. , Uniform photoconductor thickness,
It is not easy to form without coating defects. For this reason, it is preferable that the concentration of the polycarbonate copolymer resin of the present invention in the coating liquid is from 8% by weight to 13% by weight. The reason is that if it is smaller than this range, the viscosity of the coating solution is reduced, so that the speed of pulling up the conductive support during dip coating is increased, and a coating defect due to uneven evaporation of the solvent is likely to occur, which is preferable. Absent. On the other hand, if it is larger than this range, the viscosity of the coating solution becomes extremely high, and the thickness of the photosensitive layer becomes large. For this reason, the pulling speed of the drum must be made extremely slow, which leads to a reduction in productivity and is not practical. Further, if air bubbles are mixed in the coating solution, the viscosity is high, and the air bubbles remain for a long period of time, which is not preferable because the photosensitive layer becomes defective.

As the coating solvent, benzene, toluene,
Aromatic hydrocarbons such as xylene and monochlorobenzene,
Dichloromethane, halogenated hydrocarbons such as dichloroethane, dioxane, dimethoxymethyl ether, a single solvent or a mixture of two or more solvents such as dimethylformamide, or, if necessary, a solvent such as alcohols, acetonitrile, and methyl ethyl ketone Can be used.

The electrophotographic photosensitive member of the present invention has the general formula (II)
The charge transport materials shown in (I) to (V) are used as charge transfer materials, and various methods are conceivable in such embodiments. When the structure of the photoreceptor is schematically shown in FIGS.
FIG. 1 shows a photosensitive layer as a photosensitive layer on a conductive support (1) comprising a charge generation material (2) as a main component and a charge generation layer (5) dispersed in a binder and a charge transfer material (3) as main components. And a charge transfer layer (6) dispersed in a binder. The charge transfer layer (6) contains the charge transport material of the present invention as a charge transfer substance (3). 2 shows a configuration of a photoconductor used.

FIG. 2 shows the same charge generation layer (5) as in FIG.
And a charge transfer layer (6), which is a function-separated type photoreceptor having a charge generation layer (5) formed on the surface of the charge transfer layer (6). The structure of a photoreceptor using the charge transport material of the present invention as a charge transfer material (3) in a charge transfer layer (6) is shown.

FIG. 3 shows a photosensitive layer composed of a single layer in which a charge generating substance (2) and a charge transfer substance (3) are dispersed in a binder as a photosensitive layer (4) on a conductive support (1). 2 shows the configuration.

FIG. 4 shows a structure in which an intermediate layer (7) is provided between the conductive support (1) and the same photosensitive layer (4) as in FIG.
FIG. 2 shows a configuration of a function-separated type photoreceptor formed by lamination.

FIG. 5 shows a structure in which an intermediate layer (7) is provided between the conductive support (1) and the same photosensitive layer (4 ') as in FIG.
3 shows a configuration of a photoconductor having a single layer.

The intermediate layer (7) provided between the conductive support (1) and the photosensitive layer (4) imparts a protective function and an adhesive function, enhances coatability, and further allows the photosensitive layer to be exposed from the drum base. It is intended to improve charge injection into the layer, and such materials include casein, polyvinyl butyral, polyvinyl alcohol, nitrocellulose, ethylene-acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon 610, Copolymer nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin aluminum oxide and the like are suitable.

[0122]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.

Example 1 The following structural formula was used as a charge generation material.

Embedded image

X-type metal-free phthalocyanine (Fastgen Blue 8120, manufactured by Dainippon Ink Co., Ltd.) 0.4
Parts by weight and 0.3 parts by weight of a vinyl chloride-vinyl acetate copolymer resin (manufactured by Sekisui Chemical Co., Ltd .: Eslec M)
This solution was dispersed in a paint conditioner (manufactured by Red Level Co.) with glass beads having a diameter of 1.5 mm for about 2 hours to prepare a coating solution for a charge generation layer. Next, the dispersion liquid was applied by a doctor blade method using an aluminum-evaporated polyester film as a conductive support, and dried to form a charge generation layer. The film thickness after drying was 0.4 μm.

On the charge generation layer, 1 part by weight of the charge transport material exemplary compound No. 1 of the present invention and 1 part by weight of a binder resin as a copolymer resin No. P-1 of the present invention (s: t = 85: 1)
5, Dissolve 1.2 parts by weight of methylene chloride in viscosity average molecular weight of about 40,000, and dissolve solid content 15% (copolymer resin concentration 8.
(2% by weight) was applied by a squeezing doctor to prepare a charge transport layer having a dry film thickness of 25 μm. As described above, a function-separated laminated photoreceptor sample 1 composed of the charge generation layer and the charge transport layer was obtained.

Examples 2 to 15 The charge transporting material was used as the charge transporting material exemplified compound No.
3, No.4, No.6, No.8, No.26, No.91, No.12
7, No. 130, No. 177, No. 200, No. 258, N
o-259, No. 270 and No. 280 were carried out in the same manner as in Example 1 except that Nos. 259, Nos.

Comparative Example 1 A binder resin for a charge transport layer was changed to a compound consisting of the structural unit I-1 represented by the general formula (I).
Function-separated laminated photoreceptor comparative sample 1 in the same manner as in Example 1.
I got

Comparative Example 2 A binder resin for a charge transport layer was changed to a compound consisting of a structural unit I-4 represented by the general formula (I).
Function-separated laminated photoreceptor comparative sample 2 in the same manner as in Example 1.
I got

Comparative Example 3 A functionally separated laminated photoreceptor comparative sample 3 was obtained in the same manner as in Example 1 except that the charge transporting material was changed to a compound represented by the following structural formula.

[0130]

Embedded image

The thus-prepared electrophotographic photosensitive member having a function-separated type was manufactured by using an electrostatic recording paper tester (Kawaguchi Electric; S
P-428) to evaluate the electrophotographic characteristics. Measurement conditions were: applied voltage: -6 kV, static: No. 3,
From -700 V by white light irradiation (irradiation light: 5 lux)-
The amount of exposure E ₁₀₀ (lux seconds) and the initial potential V _O (−volt) required to attenuate the voltage to ₁₀₀ V were measured.
Then, using the same device, the initial potential V ₀ (−volt) and the initial potential after performing the same operation 10,000 times with one cycle of charge-discharge (discharge light: irradiation with white light for 1 second at 40 lux) are used. E ₁₀₀ (looks / second) was measured, and changes in V ₀ and E ₁₀₀ were examined.

Further, a laser printer (WD-580P) manufactured by Sharp Corporation was remodeled, the photoreceptor was attached to the drum portion, and a continuous blank copy (Non Copy Agin) was performed.
After g) was performed 10,000 times, the degree of decrease in initial potential and sensitivity was examined. Further, the degree of reduction in the photoreceptor film thickness was evaluated using an abrasion tester manufactured by Suga Test Instruments Co., Ltd. The measurement conditions are
Abrasive = aluminum oxide # 2000, load = 200 g
・ F, the number of times of friction = 10000 times. Table 7 summarizes the above measurement results.

[0133]

[Table 47]

As can be seen from Table 7, the electrophotographic photoreceptor of the present invention shows favorable values in the change in potential of the photoreceptor after aging and the amount of wear.

Embodiment 16

Embedded image

2 parts by weight of a bisazo pigment which is a charge generating material represented by the above structural formula, 1 part by weight of an epoxy resin (BPO-20E, manufactured by Shin Nippon Rika Co., Ltd.), and dimethoxyethane 97
The parts by weight were dispersed for 6 hours with a paint shaker to prepare a coating solution for a charge generation layer. This dispersion was filled in a tank, an aluminum cylindrical support having a diameter of 80 mm and a length of 348 mm was immersed, pulled up and dried at room temperature for 1 hour.
A charge generation layer having a thickness of 0.2 μm was formed.

On the other hand, 100 parts by weight of the charge transporting material exemplified compound No. 1 of the present invention as a charge transporting material and the copolymer resin No. P-1 (s: t =
85:15, 100 parts by weight of a viscosity average molecular weight of about 40,000) are dissolved in 800 parts by weight of dichloromethane to prepare a coating solution for a charge transport layer (copolymer resin concentration: 10% by weight). The resultant was coated by dip coating and dried at 80 ° C. for 1 hour to form a 25 μm-thick charge transport layer to produce a photosensitive drum. This photosensitive drum sample was mounted on a commercially available copying machine (SF-8870, manufactured by Sharp Corporation),
A copy test was performed using paper of the size. Initial and 40
After 000 uses, the image characteristics, the charged potential (V _O ), the potential (V _L ) and the residual potential (V _R ) of the white original were measured.

Example 17 Copolymer resin P-2 of the present invention as a binder resin
A photosensitive drum sample was prepared and evaluated in the same manner as in Example 16 except that (s: t = 80: 20, viscosity average molecular weight: about 40,000) was used.

Examples 18 to 21 As the charge transporting material, the compound N of the charge transporting material according to the present invention is exemplified.
Photoconductor drum samples were prepared and evaluated in the same manner as in Example 16 except that o.16, No.145, No.280 and No.294 were used.

Comparative Example 4 A photoreceptor drum sample was prepared and evaluated in the same manner as in Example 16 except that the amount of dichloromethane used in the coating solution for the charge transport layer was changed to 500 parts by weight. Since the coating liquid (copolymer resin concentration: 14.3% by weight) had a very high viscosity, the film thickness of the photoreceptor could not be made uniform, and the image was uneven in density over the entire image.

Comparative Example 5 The dichloromethane used for the coating solution for the charge transport layer was 1100
A photoconductor drum sample was prepared and evaluated in the same manner as in Example 16 except that the weight part was used. Since the coating liquid (copolymer resin concentration: 7.7% by weight) has a very low viscosity, the film thickness of the photoconductor cannot be made uniform, and the film thickness is 10 μm.
Of the charge transport layer was obtained. Table 8 summarizes the above measurement results.

[0142]

[Table 48]

As can be seen from Tables 7 and 8, the electrophotographic photoreceptor of the present invention shows good results in the change in the potential of the photoreceptor after aging, the amount of abrasion, and the image evaluation.

Examples 22 to 28 Copolymer resins P-3 to 9 of the present invention as binder resins
A photosensitive drum sample was prepared in the same manner as in Example 16 except that was used, and the image characteristics were evaluated. As a result, in the initial stage and after the use of 40,000 times, all of the drum samples showed good characteristics without reduction in image density and fogging of a white background original. In addition, it was found that there were no image defects such as white spots, black spots, and image density unevenness, and that the drum surface after the copy test did not have large scratches that would cause image defects and was excellent in abrasion resistance.

[0145]

The electrophotographic photoreceptor of the present invention has extremely good electrophotographic properties. The electrophotographic photoreceptor has a uniform photosensitive film, and at the same time has good durability against a cleaning blade, a developer and paper. Excellent, little change in electrophotographic properties even after continuous use, and more excellent printing durability compared to conventional ones. Further, according to the method for producing an electrophotographic photoreceptor of the present invention, the viscosity of the coating solution becomes a viscosity suitable for the dip coating method. Can be.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view schematically illustrating a layer configuration of an electrophotographic photosensitive member of the present invention.

FIG. 2 is a cross-sectional view schematically showing a layer configuration of the electrophotographic photosensitive member of the present invention.

FIG. 3 is a cross-sectional view schematically illustrating a layer configuration of the electrophotographic photosensitive member of the present invention.

FIG. 4 is a cross-sectional view schematically illustrating a layer configuration of the electrophotographic photosensitive member of the present invention.

FIG. 5 is a cross-sectional view schematically illustrating a layer configuration of the electrophotographic photosensitive member of the present invention.

FIG. 6 is a cross-sectional view schematically illustrating a layer configuration of the electrophotographic photosensitive member of the present invention.

[Explanation of symbols]

 REFERENCE SIGNS LIST 1 conductive support 2 charge generation material 3 charge transfer material 4 photosensitive layer 4 ′ photosensitive layer 5 charge generation layer 6 charge transfer layer 7 intermediate layer

────────────────────────────────────────────────── ───

[Procedure amendment]

[Submission date] March 6, 1998

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name]

[Correction method] Change

[Correction contents]

The electrophotographic photosensitive member of the present invention has the general formula (II)
But using the charge transporting material represented by I) ~ (V) as charge transport materials, although its embodiments are conceivable various methods and schematically shown in FIG. 5 the configuration of the photosensitive member from FIG. 1,
FIG. 1 shows a photosensitive layer as a photosensitive layer on a conductive support (1) comprising a charge generation material (2) as a main component and a charge generation layer (5) dispersed in a binder and a charge transfer material (3) as main components. And a charge transfer layer (6) dispersed in a binder. The charge transfer layer (6) contains the charge transport material of the present invention as a charge transfer substance (3). 2 shows a configuration of a photoconductor used.

[Procedure amendment 2]

[Document name to be amended] Statement

[Correction target item name]

[Correction method] Change

[Correction contents]

FIG. 3 shows a photoreceptor comprising a single layer in which a charge generating substance (2) and a charge transfer substance (3) are dispersed in a binder as a photosensitive layer (4a) on a conductive support (1). It shows the configuration of FIG.

[Procedure amendment 3]

[Document name to be amended] Statement

[Correction target item name]

[Correction method] Change

[Correction contents]

[0120] Figure 5 is intended an intermediate layer (7) is provided between the conductive support (1) and 3 and the same photosensitive layer (4 a), shows a configuration of a photosensitive member composed of a single layer Things.

[Procedure amendment 4]

[Document name to be amended] Statement

[Correction target item name] Brief description of drawings

[Correction method] Change

[Correction contents]

[Brief description of the drawings]

FIG. 1 is a cross-sectional view schematically illustrating a layer configuration of an electrophotographic photosensitive member of the present invention.

FIG. 2 is a cross-sectional view schematically showing a layer configuration of the electrophotographic photosensitive member of the present invention.

FIG. 3 is a cross-sectional view schematically illustrating a layer configuration of the electrophotographic photosensitive member of the present invention.

FIG. 4 is a cross-sectional view schematically illustrating a layer configuration of the electrophotographic photosensitive member of the present invention.

FIG. 5 is a cross-sectional view schematically illustrating a layer configuration of the electrophotographic photosensitive member of the present invention.

[Description of Signs] 1 conductive support 2 charge generation material 3 charge transfer material 4 photosensitive layer 4 a photosensitive layer 5 charge generation layer 6 charge transfer layer 7 intermediate layer

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Kaori Kushita 22-22 Nagaikecho, Abeno-ku, Osaka-shi, Osaka Inside Sharp Corporation (72) Inventor Hideharu Sakamoto 1280 Kamiizumi, Sodegaura-shi, Chiba

Claims (8)

[Claims] In a photosensitive layer formed on a conductive support, a polycarbonate containing a structural unit represented by the following general formula (I) and a structural unit represented by the following general formula (II) as main components: An electrophotographic photoreceptor comprising a copolymer resin and a compound represented by the following general formula (III). Embedded image [In the formula, R ₁ and R ₂ are each an alkyl group having 1 to 6 carbon atoms which may have a substituent, and 3 carbon atoms which may have a substituent.
To 7 represent a cycloalkyl group, an aryl group which may have a substituent or a hydrogen atom, and R ₃ and R ₄ each represent an alkyl group having 1 to 6 carbon atoms which may have a substituent; Represents a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, an aryl group optionally having a substituent, a halogen atom or a hydrogen atom, and l and m each represent an integer of 1 to 4. R ₁ and R ₂ may be bonded to each other to form a hydrocarbon ring. [Chemical formula 2] [Wherein, R ₅ and R ₆ are each an alkyl group having 1 to 6 carbon atoms which may have a substituent, and 3 carbon atoms which may have a substituent.
To 7, a cycloalkyl group, an aryl group which may have a substituent, a halogen atom, or a hydrogen atom;
Represents an integer of 1 to 4, respectively. [Chemical formula 3] [In the formula, Ar is an aryl group which may have a substituent, a heterocyclic group which may have a substituent, an aralkyl group or a heterocyclic substituted alkyl group which may have a substituent, and n is Two
Represents an integer of 4. ] 2. A polycarbonate comprising, as main components, a structural unit represented by the following general formula (I) and a structural unit represented by the following general formula (II) in a photosensitive layer formed on a conductive support. An electrophotographic photoreceptor comprising a copolymer resin and a compound represented by the following general formula (IV). Embedded image [In the formula, R ₁ and R ₂ are each an alkyl group having 1 to 6 carbon atoms which may have a substituent, and 3 carbon atoms which may have a substituent.
To 7 represent a cycloalkyl group, an aryl group which may have a substituent or a hydrogen atom, and R ₃ and R ₄ each represent an alkyl group having 1 to 6 carbon atoms which may have a substituent; Represents a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, an aryl group optionally having a substituent, a halogen atom or a hydrogen atom, and l and m each represent an integer of 1 to 4. R ₁ and R ₂ may be bonded to each other to form a hydrocarbon ring. [Chemical formula 5] [Wherein, R ₅ and R ₆ are each an alkyl group having 1 to 6 carbon atoms which may have a substituent, and 3 carbon atoms which may have a substituent.
To 7, a cycloalkyl group, an aryl group which may have a substituent, a halogen atom, or a hydrogen atom;
Represents an integer of 1 to 4, respectively. [Formula 6] [Wherein, R ₇ and R ₈ may be the same or different and each have a lower alkyl group, a cycloalkyl group optionally having a substituent, an aryl group optionally having a substituent, Or an optionally substituted aralkyl group, an optionally substituted heterocyclic group or a heterocyclic substituted alkyl group, and R ₇ and R ₈ together with the nitrogen atom to which they are attached form a nitrogen-containing heterocyclic group Is also good. R ₉ , R ₁₀ , R ₁₁ and R ₁₂ may be the same or different and represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower halogenated alkyl group, a lower alkoxy group or a lower dialkylamino group; Represents an integer of from 4 to 4. ] 3. A polycarbonate comprising a structural unit represented by the following general formula (I) and a structural unit represented by the following general formula (II) as main components in a photosensitive layer formed on a conductive support. An electrophotographic photoreceptor comprising a copolymer resin and a compound represented by the following general formula (V). Embedded image [In the formula, R ₁ and R ₂ are each an alkyl group having 1 to 6 carbon atoms which may have a substituent, and 3 carbon atoms which may have a substituent.
To 7 represent a cycloalkyl group, an aryl group which may have a substituent or a hydrogen atom, and R ₃ and R ₄ each represent an alkyl group having 1 to 6 carbon atoms which may have a substituent; Represents a cycloalkyl group having 3 to 7 carbon atoms which may have a substituent, an aryl group optionally having a substituent, a halogen atom or a hydrogen atom, and l and m each represent an integer of 1 to 4. R ₁ and R ₂ may be bonded to each other to form a hydrocarbon ring. Embedded image [Wherein, R ₅ and R ₆ are each an alkyl group having 1 to 6 carbon atoms which may have a substituent, and 3 carbon atoms which may have a substituent.
To 7, a cycloalkyl group, an aryl group which may have a substituent, a halogen atom, or a hydrogen atom;
Represents an integer of 1 to 4, respectively. Embedded image [In the formula, R ₁₃ and R ₁₄ are a hydrogen atom (excluding the case where both R ₁₃ and R ₁₄ are a hydrogen atom), an aryl group which may have a substituent, and a hetero group which may have a substituent. A ring group, an aralkyl group which may have a substituent, a lower alkyl group or a heterocyclic substituted alkyl group, a represents a lower alkyl group, a lower halogenated alkyl group, a lower alkoxy group, a halogen atom or a hydrogen atom, j is an integer of 1 to 4 (provided that j
When a is 2 or more, a may be the same or different) k
Is an integer of 2 to 4. ] 4. The electrophotographic photosensitive member according to claim 1, wherein the structural unit represented by the general formula (I) is the following structural unit (a). Embedded image 5. The electrophotographic photosensitive member according to claim 1, wherein the structural unit represented by the general formula (II) is the following structural unit (b). Embedded image 6. The structural unit represented by the general formula (I) is the following structural unit (a), and the structural unit represented by the general formula (II) is the following structural unit (b). The electrophotographic photoreceptor according to claim 1, 2 or 3. Embedded image 7. An electrophotographic photosensitive member according to claim 1, wherein the polycarbonate copolymer resin has a viscosity average molecular weight of 20,000 to 80,000. 8. A method for producing an electrophotographic photosensitive member, wherein a photosensitive layer is dip-coated on a cylindrical conductive support, wherein the concentration of the polycarbonate copolymer resin in the coating solution is 8% by weight to 13% by weight. %. The method for producing an electrophotographic photoreceptor according to claim 1, 2 or 3.