JP3928923B2 - Single layer type electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus - Google Patents

Description

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a single layer type electrophotographic photoreceptor, a process cartridge, and an electrophotographic apparatus. More specifically, the present invention relates to a single layer type electrophotographic photoreceptor, process cartridge, and electronic for use in a copying machine, a printer, and the like using an electrophotographic process. The present invention relates to a photographic apparatus.
[0002]
[Prior art]
2. Description of the Related Art Conventionally, various inorganic and organic photoconductors are known as photoconductors for photoreceptors used in electrophotography.
The “electrophotographic method” here generally means that a photoconductive photosensitive member is first charged in a dark place, for example, by corona discharge, and then image-exposed to selectively dissipate the charge of only the exposed portion. An image called the so-called Carlson process, in which an electrostatic latent image is obtained, and the latent image portion is developed with a toner composed of a colorant such as a dye or pigment and a polymer material and visualized to form an image. Forming process.
[0003]
Photoconductors using organic photoconductors have advantages in terms of freedom of photosensitive wavelength range, film formability, flexibility, film transparency, mass productivity, toxicity, cost, etc., compared to inorganic photoconductors. Therefore, development of a photoreceptor using an organic material has been actively made and put into practical use.
Most of the photoreceptors that have been put into practical use have a stacked structure composed of a layer (CGL) having a charge generation function and a layer (CTL) having a charge transport function, and are exclusively used for a negative charging process.
The reason is as follows: (1) The laminated type has a high mechanical strength, and a CTL that can be designed for film thickness is placed on the surface layer to maintain sufficient mechanical durability on the photoconductor in the state of being used in the process. It is because it becomes possible to make it.
[0004]
(2) Since organic materials that exhibit high charge mobility that does not hinder high-speed copying processes are currently limited to donor compounds that exhibit hole transfer properties, they are formed from donor compounds. The photoconductor has a CTL disposed on the surface side, and the charge polarity is negative. However, such a function separation structure creates a new problem.
[0005]
The first is derived from the negative charge of the photoreceptor.
A highly reliable charging method in the electrophotographic process is based on corona charging or contact charging, and this method is adopted in most copying machines and printers. However, as is well known, charging of negative polarity is unstable compared to positive polarity. In addition, since negative corona charging is accompanied by more generation of ozone and NOx, which are substances that cause chemical damage, there is a problem in terms of environmental problems or photoconductor damage. Although the generation amount of ozone and NOx is very small, there is a problem of damaging the photoconductor due to the charging system close to the photoconductor. From this aspect, a positively charged photoconductor is desirable.
[0006]
The second is derived from the laminated structure of the photoreceptor.
In the production of a photoreceptor using an organic material, it is possible to use a solution coating method that is less expensive than the vacuum deposition method. However, in order to produce such a laminated type photoreceptor, at least two coating operations are required. Usually, an intermediate layer is provided on the conductive support (between the conductive support and the photosensitive layer) in order to ensure the chargeability of the photosensitive member, so three coating operations are required. The coating operation leads to an increase in the cost of the photoreceptor. Furthermore, in order to maintain a balance between sensitivity and durability and to obtain a good image, managing the thickness of the CGL in the submicron range is a factor that further increases the manufacturing cost.
[0007]
In view of these problems, it can be understood that a single-layer structure that can be used in a positive charging process is desirable for a photoreceptor using an organic material.
Further, it is understood that if the photoconductor can be used in the negative charging process as it is or with slight changes, it is possible to create a photoconductor having the advantage of being inexpensive and having a high degree of freedom in use environment.
[0008]
Conventionally, as a single-layer type photoreceptor, (1) a charge transfer complex photoreceptor comprising polyvinylcarbazole and trinitrofluorenone (UPS 3489237), and (2) a eutectic complex comprising thiapyrylium dye and polycarbonate (J. Appl. Phys). .49  5555 (1978)), and (3) a photoreceptor in which a perylene pigment and a hydrazone compound are dispersed in a resin (Japanese Patent Laid-Open No. 2-37354).
[0009]
Among these, (1) and (2) have drawbacks such as low sensitivity, low electrostatic and mechanical durability, and problems in repeated use.
Since (3) has a low sensitivity of the photosensitive member, it was accompanied by a defect unsuitable for a high-speed copying process. Furthermore, when the components of a layered photoreceptor that has been put into practical use are simply dispersed, the charging potential and sensitivity are low, in particular, the electrostatic and mechanical durability is low, and they vary greatly with repeated use. The drawbacks have not been overcome.
[0010]
[Problems to be solved by the invention]
The present invention eliminates such conventional drawbacks, and is excellent in chargeability and sensitivity, particularly excellent in mechanical strength, and has a stable electrostatic property even when the copying process is repeated. It is an object of the present invention to provide a body, a process cartridge, and an electrophotographic apparatus.
[0011]
[Means for Solving the Problems]
As a result of intensive studies to solve the above problems, the present inventors have found that the photosensitive layer comprises at least a charge generating substance, a charge transfer substance, and an acceptor compound, and the charge transfer substance uses a polymer charge transfer substance. The present invention has been found to be effective for the above-mentioned problems by using a photosensitive layer.
[0012]
  That is, according to the present invention, in an electrophotographic photosensitive member in which a single photosensitive layer is provided directly or via an intermediate layer on a conductive support, the photosensitive layer includes at least a charge generating substance, a charge transporting substance, and an acceptor. And the charge transport material is a polymer charge transport material.Further, the polymer charge transporting material is a polycarbonate having a triarylamine structure represented by the general formula (11D).A single layer type electrophotographic photosensitive member is provided.
[0013]
  In addition, the acceptor compound has a high ability to attract electrons, and a large number of electrons generated by light irradiation can be transferred to the acceptor compound. In particular, the 2,3-diphenylindene compound represented by the general formula (G1) is large due to this effect, and has a highly durable single layer type that does not interfere with the practical use of the photoreceptor. An electrophotographic photoreceptor is provided.
[0014]
  In addition, a monolayer electrophotographic photoreceptor containing a phenol compound having a specific structure in the photosensitive layer is provided.
[0015]
oneThe polymer charge transport material represented by the general formula (11D) is shown.
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[In the formula (11D), Ar₃₂, Ar₃₃, Ar₃₅And Ar₃₆Is substituted or unsubstitutedAryleneRepresents a group, Ar₃₄Represents a substituted or unsubstituted aryl group. Z isAryleneGroup or -Ar₃₇-Za-Ar₃₇-Represents Ar₃₇Is substituted or unsubstitutedAryleneRepresents a group. Za represents O, S or an alkylene group. R and R 'are linear or branched alkyleneGroupTo express. h represents 0 or 1; k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents a substituted or unsubstituted aliphatic divalent group, a substituted or unsubstituted cyclic aliphatic divalent group, a substituted or unsubstituted aromatic divalent group, or a divalent group formed by linking these, or the following general group The divalent group represented by Formula (A ′), General Formula (F), and General Formula (G) is represented. ]
[0016]
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[In formula (A '), (F), (G), R_{twenty four}, R_{twenty five}, R₅₅, R₅₆Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a halogen atom. l and m each independently represent an integer of 0 to 4, and s and t each independently represents an integer of 0 to 3. R_{twenty four}, R_{twenty five}, R₅₅, R₅₆May be the same or different when there are a plurality of each. Y is composed of a single bond, a linear, branched or cyclic alkylene group having 1 to 12 carbon atoms, one or more alkylene groups having 1 to 10 carbon atoms, and one or more oxygen atoms and sulfur atoms. Divalent group, -O-, -S-, -SO-, -SO₂-, -CO-, -COO-, -CO-O-Z₁-O-CO-, -CO-Z₂-CO- (wherein Z₁, Z₂Is a substituted or unsubstituted aliphatic divalent group, or substituted or unsubstitutedAryleneGroup), or the following general formula (B) and general formulas (H) to (N). ]
[0017]
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[In the formulas (B) and (H) to (N), R₂₆, R₂₇Each independently represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. R₅₇, R₅₈, R₆₄Represents a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group. R₅₉, R₆₀, R₆₁, R₆₂, R₆₃Each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group. R₅₈And R₅₉May combine to form a carbocyclic ring having 5 to 12 carbon atoms. R₆₅And R₆₆Represents an end bond or an alkylene group having 1 to 4 carbon atoms. a is an integer of 1 to 20, b is an integer of 1 to 2000, u and w are integers of 0 to 4, and v is 1 or 2. R₂₆, R₂₇, R₅₇, R₆₄May be the same or different when there are a plurality of each. ]
[0018]
  Ar₃₄As specific examples of the aryl group, Ar in the description of the general formula (3D)_Five, Ar₆As specific examples of the aryl group,₃₂, Ar₃₃, Ar₃₅, Ar₃₆ofAryleneSpecific examples of the group include divalent groups of these aryl groups. These aryl groups,AryleneSpecific examples of the substituent in the group include an aryl group in the description of the general formula (3D) orAryleneWhat was illustrated as a substituent in group can be mentioned.
[0019]
X is introduced when a diol compound of the following general formula (11D ') is polymerized using a phosgene method, a transesterification method, or the like, in combination with a diol compound of the following general formula (C). In this case, the polycarbonate resin to be produced is a random polymer or a block polymer. X is also introduced into the repeating unit by a polymerization reaction of a diol compound of the general formula (11D ') and a bischloroformate derived from the general formula (C). In this case, the manufactured polycarbonate resin becomes an alternating copolymer.
[0020]
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Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0021]
Further, according to the present invention, the electrophotographic photosensitive member and at least one means selected from the group consisting of a charging means, an image exposing means, a developing means, a transferring means, and a cleaning means are integrally supported, and the electrophotographic apparatus main body is supported. A process cartridge is provided that is detachable.
[0022]
Furthermore, according to the present invention, there is provided an electrophotographic apparatus comprising an electrophotographic photosensitive member, a charging unit, an image exposing unit, a developing unit, and a transfer unit.
[0023]
DETAILED DESCRIPTION OF THE INVENTION
The above photoreceptors are excellent in chargeability and sensitivity, suitable for low-speed to high-speed copying processes, and spectral sensitivity can be controlled by changing the charge generation material, and optical writing from monochrome or full-color analog copying machines. For example, it can be applied to a photoconductor for a page printer using LD or LED light.
Particularly important in the photosensitive layer according to the present photoreceptor is that the charge transport material is a polymer charge transport material. As a result, it is possible to increase the sensitivity of the photosensitive member, improve the electrostatic characteristics, and particularly improve the mechanical strength.
Although this improvement mechanism is not clear at present, it is presumed as follows.
The charge generating material is present in particulate form in the photosensitive layer. Therefore, the movement of charges generated under light irradiation in the photosensitive layer is much worse between the charge generating material particles than in the charge generating material, and this process is considered to determine the charge transfer and lifetime in the photosensitive layer. It is done.
[0024]
For this reason, the charge transfer material in the matrix in which the charge generation material is dispersed and held, and the presence of the acceptor compound are greatly affected, and the use of the polymer charge transfer material of the present invention makes it very homogeneous (molecular order). It is believed that a charge transfer matrix is formed and charges are injected from the charge generating material into the charge transfer matrix and a smooth movement through the matrix is achieved.
[0025]
In addition, the acceptor compound has a high ability to attract electrons and can move the majority of the electrons generated by light irradiation to the acceptor compound side, so that the charging property, sensitivity, High durability of electrostatic characteristics can be realized.
Further, the improvement in mechanical strength of the photoconductor is considered to be due to the excellent mechanical properties of the polymer charge transport material. In addition, the use of a polymer charge transport material can cope with a wet development process that has been difficult with a single-layer type photoreceptor.
[0026]
Hereinafter, the single layer type electrophotographic photosensitive member of the present invention will be described in detail.
As described above, the single-layer electrophotographic photosensitive member of the present invention is provided with a photosensitive layer containing a polymeric charge transport material as an active ingredient as a charge transport material in the photosensitive layer.
[0027]
The general formulas (1D) to (10D), which are polymer charge transport materials, which are main structural units of the present invention, will be described in more detail.
[0028]
The polymer charge transport material represented by the general formula (1D) is shown.
[0029]
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[In the formula (1D), R ′₁, R '₂, R '_ThreeEach independently represents a substituted or unsubstituted alkyl group or a halogen atom, and R ′_FourRepresents a hydrogen atom or a substituted or unsubstituted alkyl group. R₁, R₂Represents a substituted or unsubstituted aryl group. o, p, and q each independently represents an integer of 0 to 4. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents an aliphatic divalent group, a cycloaliphatic divalent group, or a divalent group represented by the following general formula (A). ]
[0030]
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[In formula (A), R_{twenty four}, R_{twenty five}Each independently represents a substituted or unsubstituted alkyl group, aryl group or halogen atom, and l and m each represents an integer of 0 to 4. Y is a single bond, a linear, branched or cyclic alkylene group having 1 to 12 carbon atoms, -O-, -S-, -SO-, -SO.₂-, -CO-, -CO-O-Z-O-CO- (wherein Z represents an aliphatic divalent group) or the following general formula (B)
[0031]
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[In Formula (B), a represents an integer of 1 to 20, and b represents an integer of 1 to 2000. R₂₆, R₂₇Represents a substituted or unsubstituted alkyl group or aryl group. ). R_{twenty four}And R_{twenty five}, R₂₆And R₂₇May be the same or different. ]
[0032]
R '₁, R '₂, R '_ThreeThe alkyl group is preferably a C1 to C12, particularly C1 to C8, more preferably a C1 to C4 linear or branched alkyl group, and these alkyl groups further include a fluorine atom, a hydroxyl group, a cyano group, You may contain the phenyl group substituted by the C4 alkoxy group, the phenyl group, or the halogen atom, the C1-C4 alkyl group, or the C1-C4 alkoxy group.
Specifically, 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 and the like.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
R '_FourAs the substituted or unsubstituted alkyl group, the above R ′₁, R '₂, R '_ThreeThe same thing is mentioned.
R₁, R₂As the aryl group, an aromatic hydrocarbon group such as a phenyl group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, Condensed polycyclic groups such as fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycyclic groups such as biphenylyl group and terphenylyl group, chenyl group, benzocenyl group, furyl group, benzofuranyl And heterocyclic groups such as a carbazolyl group.
[0033]
The above aryl group may have the following groups as substituents.
[0034]
(1) Halogen atom, trifluoromethyl group, cyano group, nitro group.
[0035]
(2) Alkyl group: R 'above₁, R '₂, R '_ThreeThe thing similar to what was shown as an alkyl group of is mentioned.
[0036]
(3) Alkoxy group (-OR₄₁): R₄₁Represents the alkyl group shown in (2) above. 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-cyano Examples include ethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like.
[0037]
(4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C1-C4 alkoxy group, a C1-C4 alkyl group or a halogen atom as a substituent. Specific examples include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methylphenoxy group, 4-methoxyphenoxy group, 4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. It is done.
[0038]
(5) Substituted mercapto group or aryl mercapto group: Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group.
[0039]
(6) Alkyl-substituted amino group: The alkyl group represents the alkyl group shown in the above (2). Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group.
[0040]
(7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.
[0041]
X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (1D ′) by using a diol compound represented by the following general formula (C) in combination with the diol compound represented by the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (1D ′) and a bischloroformate derived from the following general formula (C).
In this case, the produced polycarbonate becomes an alternating copolymer.
[0042]
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[0043]
Specific examples of the diol compound of the general formula (C) 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 -Aliphatic diols such as propanediol, 2,2-dimethyl-1,3-propanediol, 2-ethyl-1,3-propanediol, diethylene glycol, triethylene glycol, polyethylene glycol, polytetramethylene ether glycol, And cycloaliphatic diols such as 4-cyclohexanediol, 1,3-cyclohexanediol, and cyclohexane-1,4-dimethanol. Examples of the diol having an aromatic ring include 4,4'-dihydroxydiphenyl, bis (4-hydroxyphenyl) methane, 1,1-bis (4-hydroxyphenyl) ethane, and 1,1bis (4-hydroxyphenyl). -1-phenylethane, 2,2-bis (4-hydroxyphenyl) propane, 2,2-bis (3-methyl-4-hydroxyphenyl) propane, 1,1-bis (4-hydroxyphenyl) cyclohexane, 1 , 1-bis (4-hydroxyphenyl) cyclopentane, 2,2-bis (3-phenyl-4-hydroxyphenyl) propane, 2,2-bis (3-isopropyl-4-hydroxyphenyl) propane, 2,2 -Bis (4-hydroxyphenyl) butane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propa 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane, 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfoxide, 4,4'-dihydroxydiphenyl sulfide, 3,3 '-Dimethyl-4,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxydiphenyl oxide, 2,2-bis (4-hydroxyphenyl) hexafluoropropane, 9,9-bis (4-hydroxyphenyl) fluorene, 9,9-bis (4-hydroxyphenyl) xanthene, ethylene glycol-bis (4-hydroxybenzoate), diethylene glycol-bis (4-hydroxybenzoate), triethylene glycol-bis (4-hydroxybenzoate), 1,3- Bis (4-hydr Kishifeniru) - tetramethyl disiloxane, and the like phenol-modified silicone oil.
[0044]
Next, the polymeric charge transport material represented by the general formula (2D) is shown.
[0045]
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[In formula (2D), R_Three, R_FourRepresents a substituted or unsubstituted aryl group, Ar₁, Ar₂, Ar_ThreeAre the same or differentAryleneRepresents a group. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents the same group as described in the general formula (1D). ]
[0046]
R_Three, R_FourAs the aryl group, an aromatic hydrocarbon group such as phenyl group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, Condensed polycyclic groups such as fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, heterocyclic groups such as chenyl group, benzocenyl group, furyl group, benzofuranyl group, carbazolyl group, biphenylyl group, Examples thereof include a terphenylyl group and a non-condensed polycyclic group represented by the following general formula (I).
[0047]
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[In the formula (I), W represents -O-, -S-, -SO-, -SO.₂-, -CO- and the following general formulas (b), (c), (d), and (e) represent divalent groups.
[0048]
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[In the formulas (b), (c), (d), (e), c represents an integer of 1 to 12, and d, e, and f represent an integer of 1 to 3. ]
Ar₁, Ar₂, Ar_ThreeofAryleneAs the group, R_Three, R_FourAnd a divalent group of the aryl group represented by. R_Three, R_FourAn aryl group of Ar₁, Ar₂, Ar_ThreeofAryleneThe group may have a group shown below as a substituent. Moreover, these substituents are R in the general formulas (a), (d) and (e).₃₁, R₃₂, R₃₃It is also a specific example.
[0049]
(1) Halogen atom, trifluoromethyl group, cyano group, nitro group.
[0050]
(2) Alkyl group: Preferably, it is C1-C12, especially C1-C8, more preferably C1-C4 linear or branched alkyl group, and these alkyl groups are further fluorine atom, hydroxyl group, cyano group, C1 It may contain a phenyl group substituted with a C4 alkoxy group, a phenyl group, or a halogen atom, a C1 to C4 alkyl group, or a C1 to C4 alkoxy group. Specifically, 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 and the like.
[0051]
(3) Alkoxy group (-OR₄₁): R₄₁Represents the alkyl group shown in (2) above. 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-cyano Examples include ethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like.
[0052]
(4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C1-C4 alkoxy group, a C1-C4 alkyl group or a halogen atom as a substituent. Specific examples include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methylphenoxy group, 4-methoxyphenoxy group, 4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. It is done.
[0053]
(5) Substituted mercapto group or aryl mercapto group: Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group.
[0054]
(6) General formula -N (R₄₂) (R₄₃A substituted amino group represented by:
[0055]
R₄₂And R₄₃Each independently represents an alkyl group represented by (2) above or R_Three, R_FourPreferred examples of the aryl group include a phenyl group, a biphenyl group, and a naphthyl group, and these include a C1-C4 alkoxy group, a C1-C4 alkyl group, or a halogen atom as a substituent. You may do it. 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, piperidino group, morpholino group, Examples include a yurolidyl group.
[0056]
(7) An alkylenedioxy group or an alkylenedithio group such as a methylenedioxy group or a methylenedithio group.
[0057]
X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (2D ′) by using a diol compound represented by the following general formula (C) in combination with the diol compound represented by the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (2D ′) and a bischloroformate derived from the following general formula (C).
In this case, the produced polycarbonate becomes an alternating copolymer.
[0058]
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Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0059]
Next, the polymeric charge transport material represented by the general formula (3D) is shown.
[0060]
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[In formula (3D), R_Five, R₆Represents a substituted or unsubstituted aryl group, Ar_Four, Ar_Five, Ar₆Are the same or differentAryleneRepresents a group. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents the same group as described in the general formula (1D). ]
[0061]
R_Five, R₆As the aryl group, an aromatic hydrocarbon group such as a phenyl group, naphthyl group, pyrenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, azulenyl group, anthryl group, triphenylenyl group, chrysenyl group, Condensed polycyclic groups such as fluorenylidenephenyl group, 5H-dibenzo [a, d] cycloheptenylidenephenyl group, non-condensed polycyclic groups such as biphenylyl group and terphenylyl group, chenyl group, benzocenyl group, furyl group, benzofuranyl And heterocyclic groups such as a carbazolyl group.
[0062]
  Ar_Four, Ar_Five, Ar₆ofAryleneAs the group, R_Five, R₆And a divalent group of the aryl group represented by. R_Five, R₆An aryl group of Ar_Four, Ar_Five, Ar₆ofAryleneThe group may have a group shown below as a substituent.
[0063]
(1) Halogen atom, trifluoromethyl group, cyano group, nitro group.
[0064]
(2) Alkyl group: Preferably, it is C1-C12, especially C1-C8, more preferably C1-C4 linear or branched alkyl group, and these alkyl groups are further fluorine atom, hydroxyl group, cyano group, C1 It may contain a phenyl group substituted with a C4 alkoxy group, a phenyl group, or a halogen atom, a C1 to C4 alkyl group, or a C1 to C4 alkoxy group. Specifically, 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 and the like.
[0065]
(3) Alkoxy group (-OR₄₁): R₄₁Represents the alkyl group shown in (2) above. 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-cyano Examples include ethoxy group, benzyloxy group, 4-methylbenzyloxy group, trifluoromethoxy group and the like.
[0066]
(4) Aryloxy group: Examples of the aryl group include a phenyl group and a naphthyl group. These may contain a C1-C4 alkoxy group, a C1-C4 alkyl group or a halogen atom as a substituent. Specific examples include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methylphenoxy group, 4-methoxyphenoxy group, 4-chlorophenoxy group, 6-methyl-2-naphthyloxy group and the like. It is done.
[0067]
(5) Substituted mercapto group or aryl mercapto group: Specific examples include a methylthio group, an ethylthio group, a phenylthio group, and a p-methylphenylthio group.
[0068]
(6) Alkyl-substituted amino group: The alkyl group represents the alkyl group shown in the above (2). Specific examples include a dimethylamino group, a diethylamino group, an N-methyl-N-propylamino group, and an N, N-dibenzylamino group.
[0069]
(7) Acyl group: Specific examples include an acetyl group, a propionyl group, a butyryl group, a malonyl group, and a benzoyl group.
[0070]
X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (3D ′) by using a diol compound represented by the following general formula (C) in combination with the diol compound represented by the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (3D ′) and a bischloroformate derived from the following general formula (C).
In this case, the produced polycarbonate becomes an alternating copolymer.
[0071]
Embedded image
Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0072]
Next, a polymeric charge transport material represented by the general formula (4D) is shown.
[0073]
Embedded image
[In formula (4D), R₇, R₈Represents a substituted or unsubstituted aryl group, Ar₇, Ar₈, Ar₉Are the same or differentAryleneRepresents a group. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. r represents an integer of 1 to 5. X represents the same group as described in the general formula (1D). ]
[0074]
  R₇, R₈As a specific example of the aryl group, R in the description of the general formula (3D)_Five, R₆As specific examples of the aryl group,₇, Ar₈, Ar₉ofAryleneSpecific examples of the group include divalent groups of these aryl groups. These aryl groups orAryleneSpecific examples of the substituent in the group include an aryl group in the description of the general formula (3D) orAryleneWhat was illustrated as a substituent in group can be mentioned.
[0075]
X is obtained by polymerizing a diol compound having a triarylamino group of the following general formula (4D ') by using a diol compound of the following general formula (C) in combination with the diol compound of the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (4D ′) and a bischloroformate derived from the following general formula (C).
In this case, the produced polycarbonate becomes an alternating copolymer.
[0076]
Embedded image
Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0077]
Next, the polymeric charge transport material represented by the general formula (5D) is shown.
[0078]
Embedded image
[In formula (5D), R₉, R_TenRepresents a substituted or unsubstituted aryl group, Ar_Ten, Ar₁₁, Ar₁₂Are the same or differentAryleneRepresents a group. X₁, X₂Represents a substituted or unsubstituted ethylene group or a substituted or unsubstituted vinylene group. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents the same group as described in the general formula (1D). ]
[0079]
  R₉, R_TenAs a specific example of the aryl group, R in the description of the general formula (3D)_Five, R₆As specific examples of the aryl group,_Ten, Ar₁₁, Ar₁₂ofAryleneSpecific examples of the group include divalent groups of these aryl groups. These aryl groups orAryleneSpecific examples of the substituent in the group include an aryl group in the description of the general formula (3D) orAryleneWhat was illustrated as a substituent in group can be mentioned. X₁, X₂Examples of the substituent in the ethylene group or vinylene group include a cyano group, a halogen atom, a nitro group, an aryl group exemplified as a specific example of the aryl group of R5 and R6 in the description of the general formula (3D), In the description of the aryl group orAryleneThe alkyl group illustrated as a substituent in group, etc. are mentioned.
[0080]
X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (5D ′) by using a diol compound represented by the following general formula (C) in combination with the diol compound represented by the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (5D ') and a bischloroformate derived from the following general formula (C).
In this case, the produced polycarbonate becomes an alternating copolymer.
[0081]
Embedded image
Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0082]
Next, the polymeric charge transport material represented by the general formula (6D) is shown.
[0083]
Embedded image
[In formula (6D), R₁₁, R₁₂, R₁₃, R₁₄Represents a substituted or unsubstituted aryl group, Ar₁₃, Ar₁₄, Ar₁₅, Ar₁₆Are the same or differentAryleneRepresents a group. Y₁, Y₂, Y_ThreeRepresents a single bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkylene ether group, an oxygen atom, a sulfur atom or a vinylene group, which may be the same or different. Good. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents the same group as described in the general formula (1D). ]
R₁₁, R₁₂, R₁₃, R₁₄As a specific example of the aryl group, R in the description of the general formula (3D)_Five, R₆As specific examples of the aryl group,₁₃, Ar₁₄, Ar₁₅, Ar₁₆ofAryleneSpecific examples of the group include divalent groups of these aryl groups. These aryl groups orAryleneSpecific examples of the substituent in the group include an aryl group in the description of the general formula (3D) orAryleneWhat was illustrated as a substituent in group can be mentioned.
[0084]
  Y₁, Y₂, Y_ThreeAs the alkylene group, an aryl group in the description of the general formula (3D) orAryleneExamples thereof include a divalent group derived from the alkyl group exemplified as the substituent in the group. 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. Examples of the cycloalkylene group include a 1,1-cyclopentylene group, a 1,1-cyclohexylene group, and a 1,1-cyclooctylene group. Examples of the alkylene ether group include a dimethylene ether group, a diethylene ether group, an ethylene methylene ether group, a bis (triethylene) ether group, and a polytetramethylene ether group.
[0085]
X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (6D ′) by using a diol compound represented by the following general formula (C) in combination with the diol compound represented by the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (6D ′) and a bischloroformate derived from the following general formula (C). In this case, the produced polycarbonate becomes an alternating copolymer.
[0086]
Embedded image
Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0087]
Next, the polymeric charge transport material represented by the general formula (7D) is shown.
[0088]
Embedded image
[In formula (7D), R₁₅, R₁₆Represents a hydrogen atom, a substituted or unsubstituted aryl group, and R₁₅And R₁₆May form a ring. Ar₁₇, Ar₁₈, Ar₁₉Are the same or differentAryleneRepresents a group. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents the same group as described in the general formula (1D). ]
[0089]
  R₁₅, R₁₆As a specific example of the aryl group, R in the description of the general formula (3D)_Five, R₆As specific examples of the aryl group, those exemplified above can be given, and R₁₅And R₁₆Examples of the case where 9 forms a ring include 9-fluorinidene, 5H-dibenzo [a, d] cycloheptenylidene, and the like. Ar₁₇, Ar₁₈, Ar₁₉ofAryleneSpecific examples of the group include divalent groups of these aryl groups. These aryl groups orAryleneSpecific examples of the substituent in the group include an aryl group in the description of the general formula (3D) orAryleneWhat was illustrated as a substituent in group can be mentioned.
[0090]
X is obtained by polymerizing a diol compound having a triarylamino group of the following general formula (7D ′) by using a diol compound of the following general formula (C) in combination with the diol compound of the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (7D ′) and a bischloroformate derived from the following general formula (C).
In this case, the produced polycarbonate becomes an alternating copolymer.
[0091]
Embedded image
Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0092]
Next, the polymeric charge transport material represented by General Formula (8D) is shown.
[0093]
Embedded image
[In formula (8D), R₁₇Represents a substituted or unsubstituted aryl group, Ar₂₀, Ar_{twenty one}, Ar_{twenty two}, Ar_{twenty three}Are the same or differentAryleneRepresents a group. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents the same group as described in the general formula (1D). ]
R₁₇As a specific example of the aryl group, R in the description of the general formula (3D)_Five, R₆As specific examples of the aryl group,₂₀, Ar_{twenty one}, Ar_{twenty two}, Ar_{twenty three}ofAryleneSpecific examples of the group include divalent groups of these aryl groups. These aryl groups orAryleneSpecific examples of the substituent in the group include an aryl group in the description of the general formula (3D) orAryleneWhat was illustrated as a substituent in group can be mentioned.
[0094]
X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (8D ′) by using a diol compound represented by the following general formula (C) in combination with the diol compound represented by the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (8D ') and a bischloroformate derived from the following general formula (C). In this case, the produced polycarbonate becomes an alternating copolymer.
[0095]
Embedded image
Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0096]
Next, the polymeric charge transport material represented by General Formula (9D) is shown.
[0097]
Embedded image
[In formula (9D), R₁₈, R₁₉, R₂₀, R_{twenty one}Represents a substituted or unsubstituted aryl group, Ar_{twenty four}, Ar_{twenty five}, Ar₂₆, Ar₂₇, Ar₂₈Are the same or differentAryleneRepresents a group. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents the same group as described in the general formula (1D). ]
[0098]
  R₁₈, R₁₉, R₂₀, R_{twenty one}As a specific example of the aryl group, R in the description of the general formula (3D)_Five, R₆As specific examples of the aryl group,_{twenty four}, Ar_{twenty five}, Ar₂₆, Ar₂₇, Ar₂₈ofAryleneSpecific examples of the group include divalent groups of these aryl groups. These aryl groups orAryleneSpecific examples of the substituent in the group include an aryl group in the description of the general formula (3D) orAryleneWhat was illustrated as a substituent in group can be mentioned.
[0099]
X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (9D ') by using a diol compound represented by the following general formula (C) in combination with a diol compound represented by the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (9D ') and a bischloroformate derived from the following general formula (C). In this case, the produced polycarbonate becomes an alternating copolymer.
[0100]
Embedded image
Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0101]
Next, the polymeric charge transport material represented by General Formula (10D) is shown.
[0102]
Embedded image
[In formula (10D), R_{twenty two}, R_{twenty three}Represents a substituted or unsubstituted aryl group, Ar₂₉, Ar₃₀, Ar₃₁Are the same or differentAryleneRepresents a group. k and j represent compositions, and 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X represents the same group as described in the general formula (1D). ]
[0103]
  R_{twenty two}, R_{twenty three}As a specific example of the aryl group, R in the description of the general formula (3D)_Five, R₆As specific examples of the aryl group,₂₉, Ar₃₀, Ar₃₁ofAryleneSpecific examples of the group include divalent groups of these aryl groups. These aryl groups orAryleneSpecific examples of the substituent in the group include an aryl group in the description of the general formula (3D) orAryleneWhat was illustrated as a substituent in group can be mentioned.
[0104]
X is obtained by polymerizing a diol compound having a triarylamino group represented by the following general formula (10D ′) by using a diol compound represented by the following general formula (C) in combination with the diol compound represented by the following general formula (C). To be introduced.
In this case, the manufactured 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 of the following general formula (10D ′) and a bischloroformate derived from the following general formula (C). In this case, the produced polycarbonate becomes an alternating copolymer.
[0105]
Embedded image
Specific examples of the diol compound of the general formula (C) include those exemplified in the description of the general formula (1D).
[0106]
Although the exemplary compounds of general formulas (1D) to (10D) are shown in Table 1 (Table 1-1 to Table 1-12), the present invention is not limited thereto.
Moreover, although the exemplary compound of general formula (11D) is shown, this invention is not necessarily limited to these.
[0107]
[Table 1]
[0108]
[Table 2]
[0109]
[Table 3]
[0110]
[Table 4]
[0111]
[Table 5]
[0112]
[Table 6]
[0113]
[Table 7]
[0114]
[Table 8]
[0115]
[Table 9]
[0116]
[Table 10]
[0117]
[Table 11]
[0118]
[Table 12]
The amount of the polymeric charge transport material used in the present invention in the entire photosensitive layer is 20 to 95% by weight, preferably 30 to 80% by weight.
[0119]
The polymer charge transport material (11D) is exemplified below.
Embedded image
[Chemical Formula 86]
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[0120]
In the photoreceptor of the present invention, a charge generating material is included as an essential component. Examples of the charge generating material that can be used in the present invention include inorganic materials such as selenium, selenium-tellurium, cadmium sulfide, cadmium sulfide-selenium, and α-silicon, and organic materials such as C.I. Pigment Blue 25 (Color Index CI21180). ), CI Pigment Red 41 (CI 21200), CI Acid Red 52 (CI 45100), CI Basic Red 3 (CI 45210), an azo pigment having a carbazole skeleton (JP-A-53-95033), a distyrylbenzene skeleton An azo pigment having a triphenylamine skeleton (Japanese Patent Laid-Open No. 53-132347), an azo pigment having a dibenzothiophene skeleton (Japanese Patent Laid-Open No. 54-21728) ), An azo pigment having a oxadiazole skeleton (Japanese Patent Laid-Open No. 54-12742), an azo pigment having a fluorenone skeleton (Japanese Patent Laid-Open No. 54-22834), an azo pigment having a bis-stilbene skeleton (Japanese Patent Laid-Open No. 54-17733) ), An azo pigment having a distyryl oxadiazole skeleton (Japanese Patent Laid-Open No. 54-2129), an azo pigment having a distyryl carbazole skeleton (Japanese Patent Laid-Open No. 54-14967), for example, CI Pigment Blue 16 (CI 74100), phthalocyanine pigments such as titanyl phthalocyanine, for example, indigo pigments such as C.I. Len Scarlet R (Bayer Perylene pigments, etc.).
These pigments may be used alone or in combination of two or more.
The amount of these charge generation materials in the photosensitive layer is suitably 0.1 to 40% by weight, preferably 0.3 to 25% by weight. It is preferable to do this.
[0121]
Further, the photosensitive layer of the present invention contains an acceptor compound as an essential component.
Examples of the acceptor compound that can be used in the present invention include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2,4,5,7-tetranitro. -9-fluorenone, 2,4,5,7-tetranitroxanthone, 2,4,8-trinitrothioxanthone, 2,6,8-trinitro-indeno 4H-indeno [1,2-b] thiophene-4- ON, 1,3,7-trinitrodibenzothiophene-5,5-dioxide and the like, and (2,3-diphenyl-1-indenylidene) malononitrile represented by the following general formula (A1), Acceptor compounds listed in the formulas (A2) and (A3) can be preferably used.
[0122]
Furthermore, the 2,3-diphenylindene compound of the general formula (F1) is preferably used because it is compatible with the polymer matrix and has a high electron transport capability.
[0123]
In the 2,3-diphenylindene compound of the general formula (F1) of the present invention, f₁~ F_FourIs a halogen atom such as a hydrogen atom, fluorine atom or chlorine atom, an alkyl group such as a methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group or t-butyl group, benzyl group, methoxymethyl Group, a substituted alkyl group such as methoxyethyl group, cyano, group, or nitro group, and A and B are a hydrogen atom, a halogen atom such as a fluorine atom, a chlorine atom, a methyl group, an ethyl group, an n-propyl group, Alkyl groups such as iso-propyl group, n-butyl group and t-butyl group, substituted alkyl groups such as benzyl group, methoxymethyl group and methoxyethyl group, alkoxycarbonyl such as cyano, group, methoxycarbonyl group and ethoxycarbonyl group Group, substituted alkylcarbonyl groups such as benzyloxycarbonyl group and methoxyethylcarbonyl group, phenyl , Aryl groups such as naphthyl group, examples of the substituent group include an alkyl group such as a methyl group, an ethyl group, a phenyl group, a methoxy group, an ethoxy group, a phenoxy group, a fluorine atom, a halogen atom such as chlorine atom.
In particular, in general formula (F1), tolyl is suitably used for (2,3-diphenyl-1-indene) malon represented by formula (2).
[0124]
In the phenol compound of the general formula (G1) of the present invention, g₁~ G₈Is a hydrogen atom, an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group or a t-butyl group, or a substituted alkyl group such as a benzyl group, a methoxymethyl group or a methoxyethyl group , Alkoxycarbonyl groups such as methoxycarbonyl group and ethoxycarbonyl group, substituted alkylcarbonyl groups such as benzyloxycarbonyl group and methoxyethylcarbonyl group, aryl groups such as phenyl group and naphthyl group, and the substituents include methyl group and ethyl group And a halogen atom such as an alkyl group such as phenyl group, methoxy group, ethoxy group, phenoxy group, fluorine atom and chlorine atom.
[0125]
The content of these phenol compounds in the photosensitive layer is 0.1 to 50% by weight, preferably 0.1 to 30% by weight.
If the amount is less than 0.1% by weight, the effect of improving the repeated durability is not sufficient, and if it exceeds 50% by weight, the mechanical durability is lowered and the sensitivity is lowered.
[0126]
Specific examples of the phenol compound of the present invention include those shown in Table 4, but are not limited thereto.
[0127]
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These organic acceptor compounds may be used alone or in combination of two or more.
[0128]
The amount of these organic acceptor compounds in the photosensitive layer is 1 to 40% by weight, preferably 5 to 40% by weight.
[0129]
In the photosensitive layer of the present invention, a low-molecular hole transfer substance can be added as necessary for the purpose of improving the chargeability and sensitivity.
[0130]
Examples of the low molecular weight hole transfer substance used in the present invention include oxazole derivatives, oxadiazole derivatives (described in JP-A Nos. 52-139065 and 52-139066), imidazole derivatives, triphenylamine derivatives (specialty). JP-A-3-285960), benzidine derivatives (described in JP-B-58-32372), α-phenylstilbene derivatives (described in JP-A-57-73075), hydrazone derivatives (JP-A-55- No. 154955, No. 55-156954, No. 55-52063, No. 56-81850, etc.), triphenylmethane derivatives (described in JP-B-5-10983), anthracene derivatives (JP-A No. 51). No. -94829), styryl derivatives (Japanese Patent Laid-Open Nos. 56-29245 and 58-1). 8043 No. described in JP), described in JP-carbazole derivatives (JP-58-58552), pyrene derivatives (described in Japanese Patent Laid-Open No. 2-94812) is used.
[0131]
Additives such as a plasticizer, an antioxidant, a light stabilizer, a heat stabilizer, and a lubricant can be added to the photosensitive layer as necessary for the purpose of improving chargeability.
As this plasticizer, halogenated paraffin, dimethylnaphthalene and dibutyl phthalate are antioxidants, and as a light stabilizer, phenol compound, hydroquinone compound, hindered phenol compound, hindered amine compound, hindered amine and hindered phenol are in the same molecule. Examples of the compound are present.
[0132]
As the conductive substrate, a metal plate such as aluminum, nickel, copper, titanium, gold, and stainless steel, a metal drum or a metal foil, a plastic film on which aluminum, nickel, copper, titanium, gold, tin oxide, indium oxide, etc. are deposited or Examples thereof include paper, a plastic film or a drum coated with a conductive substance.
[0133]
Moreover, you may provide an intermediate | middle layer on an electroconductive base | substrate as needed.
The intermediate layer generally contains a resin as a main component. However, considering that the photosensitive layer is coated with a solvent on these resins, it is desirable that the resin be a resin having a high solvent resistance with respect to a general organic solvent.
Examples of such resins include water-soluble resins such as polyvinyl alcohol, casein, and sodium polyacrylate, alcohol-soluble resins such as copolymer nylon and methoxymethylated nylon, polyurethane resins, melamine resins, phenol resins, alkyd-melamine resins, Examples thereof include curable resins that form a three-dimensional network structure such as epoxy resins.
A metal oxide fine powder pigment exemplified by titanium oxide, silica, alumina, zirconium oxide, tin oxide, indium oxide and the like may be added to the intermediate layer in order to prevent moire and reduce residual potential.
These intermediate layers can be formed using an appropriate solvent and coating method as in the above-mentioned photosensitive layer.
Furthermore, as the intermediate layer of the present invention, a silane coupling agent, a titanium coupling agent, a chromium coupling agent, or the like can be used.
In addition, Al₂O_ThreeAnodic oxidation, organic materials such as polyparaxylylene (parylene), SiO₂, SnO₂TiO₂, ITO, CeO₂A material provided with an inorganic material such as a vacuum thin film can also be used favorably.
The thickness of the intermediate layer is suitably from 0 to 5 μm.
[0134]
Further, a protective layer may be provided on the photosensitive layer in order to improve mechanical durability such as friction resistance.
Materials used for the protective layer include ABS resin, ACS resin, olefin-vinyl monomer copolymer resin, chlorinated polyether resin, allyl resin, phenol resin, polyacetal resin, polyamide resin, polyamideimide resin, polyacrylate resin , Polyallylsulfone resin, polybutylene resin, polybutylene terephthalate resin, polycarbonate resin, polyethersulfone resin, polyethylene resin, polyethylene terephthalate resin, polyimide resin, acrylic resin, polypropylene resin, polyphenylene oxide resin, polysulfone resin, polystyrene resin, AS resin Butadiene-styrene copolymer resin, polyurethane resin, polyvinyl chloride resin, polyvinylidene chloride resin, epoxy resin and the like.
For the purpose of improving wear resistance, the protective layer contains fluorine resin such as polytetrafluoroethylene, silicone resin, and those in which inorganic materials such as titanium oxide, tin oxide and potassium titanate are dispersed in these resins. can do.
As a method for forming the protective layer, a normal coating method can be employed.
In addition, about 0.1-10 micrometers is suitable for the thickness of a protective layer.
In addition to the above, known materials such as a-C and a-SiC formed by a vacuum thin film manufacturing method can also be used as the protective layer.
[0135]
The photoreceptor of the present invention prepares a photosensitive layer forming solution by dissolving or dispersing the above materials in an organic solvent, and this is applied to the conductive support or through an intermediate layer by dipping or blade coating. It is formed by applying and drying by the spraying method.
If necessary, it is also possible to prepare a photosensitive layer forming solution by previously dispersing a charge generating substance and dissolving or dispersing it together with other materials.
[0136]
Examples of the dispersion method include ball mill dispersion, ultrasonic dispersion, and homomixer dispersion.
The thickness of the photosensitive layer of the present invention is 5 to 100 μm, preferably 10 to 40 μm. When the thickness is less than 5 μm, the chargeability is lowered. Conversely, when the thickness is more than 100 μm, the sensitivity is lowered.
[0137]
Examples of the solvent used for preparing the dispersion or solution of the photosensitive layer include N, N-dimethylformamide, toluene, xylene, monochlorobenzene, 1,2-dichloroethane, 1,1,1-trichloroethane, and dichloromethane. 1,1,2-trichloroethane, trichloroethylene, tetrahydrofuran, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl acetate, butyl acetate, dioxane, dioxolane and the like.
[0138]
In the photosensitive layer of the present invention, a binder can be added as necessary for the purpose of improving the chargeability, sensitivity, dispersibility and the like.
[0139]
Any material can be used as the binder used for forming the photosensitive layer as long as it is a conventionally known binder for electrophotographic photoreceptors having good insulation properties, and is not particularly limited.
For example, polyethylene resin, polyvinyl butyral resin, polyvinyl formal resin, polystyrene resin, phenoxy resin, polypropylene resin, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenol resin, polyester resin, alkyd resin Addition resins such as polycarbonate resins, polyamide resins, silicone resins, melamine resins, polyaddition resins, polycondensation resins, and copolymer resins containing two or more of these resin repeating units, for example, In addition to insulating resins such as vinyl chloride-vinyl acetate copolymer, styrene-acrylic copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer resin, polymer organic semiconductors such as poly-N-vinylcarbazole Can be mentioned.
These binders can be used alone or as a mixture of two or more.
[0140]
Next, the electrophotographic method and the electrophotographic apparatus will be described in detail.
FIG. 1 is a schematic view for explaining an electrophotographic process cartridge and an electrophotographic apparatus of the present invention, and the following modifications also belong to the category of the present invention.
[0141]
In FIG. 1, a photoreceptor 1 is provided with a single-layer type photosensitive layer on a conductive support.
The photosensitive member 1 has a drum shape, but may be a sheet shape or an endless belt shape. For the charging charger 3, the pre-transfer charger 7, the transfer charger 10, the separation charger 11, and the pre-cleaning charger 13, known means such as a corotron, a scorotron, a solid state charger (solid state charger), and a charging roller are used. It is done.
[0142]
As the transfer means, the above charger can be generally used, but a combination of a transfer charger and a separation charger as shown in FIG. 1 is effective.
[0143]
For light sources such as the image exposure unit 5 and the charge removal lamp 2, light emitting materials such as fluorescent lamps, tungsten lamps, halogen lamps, mercury lamps, sodium lamps, light emitting diodes (LEDs), semiconductor lasers (LD), and electroluminescence (EL) Can be used. Various types of filters such as a sharp cut filter, a band pass filter, a near infrared cut filter, a dichroic filter, an interference filter, and a color temperature conversion filter can be used to irradiate only light in a desired wavelength range. Such a light source or the like irradiates the photosensitive member with light by providing a transfer process, a static elimination process, a cleaning process, or a pre-exposure process using light irradiation in addition to the process shown in FIG.
[0144]
The toner developed on the photoreceptor 1 by the developing unit 6 is transferred to the transfer paper 9, but not all is transferred, and some toner remains on the photoreceptor 1. Such toner is removed from the photoreceptor by the fur brush 14 and the blade 15. Cleaning may be performed only with a cleaning brush, and a known brush such as a fur brush or a mag fur brush is used as the cleaning brush.
[0145]
When the electrophotographic photosensitive member is positively (negatively) charged and image exposure is performed, a positive (negative) electrostatic latent image is formed on the surface of the photosensitive member. If this is developed with toner of negative (positive) polarity (detection fine particles), a positive image can be obtained, and if developed with toner of positive (negative) polarity, a negative image can be obtained. A known method is applied to the developing unit, and a known method is also used for the charge eliminating unit.
[0146]
FIG. 2 shows another example of an electrophotographic process according to the present invention.
The photosensitive member 21 has the photosensitive layer of the present invention, is driven by driving rollers 22a and 22b, is charged by a charger 23, image exposure by a light source 24, development (not shown), transfer using a charger 25, Exposure before cleaning with the light source 26, cleaning with the brush 27, and static elimination with the light source 28 are repeated. In FIG. 2, the photoconductor 21 (of course, the conductive support is translucent in this case) is irradiated with pre-cleaning exposure light from the conductive support side.
[0147]
The above illustrated electrophotographic process is illustrative of an embodiment of the present invention, and of course other embodiments are possible.
For example, in FIG. 2, the pre-cleaning exposure is performed from the support side, but this may be performed from the photosensitive layer side, or image exposure and neutralization light irradiation may be performed from the support side.
[0148]
On the other hand, in the light irradiation process, image exposure, pre-cleaning exposure, and static elimination exposure are illustrated. In addition, pre-exposure exposure, pre-exposure of image exposure, and other known light irradiation processes are provided to light the photosensitive member. Irradiation can also be performed.
[0149]
The image forming means as described above may be fixedly incorporated in a copying apparatus, a facsimile, or a printer, but may be incorporated in these apparatuses in the form of a process cartridge. A process cartridge is a single device (part) that contains a photosensitive member and includes a charging unit, an exposure unit, a developing unit, a transfer unit, a cleaning unit, and a charge eliminating unit. There are many shapes and the like of the process cartridge, but a general example is shown in FIG. The photoreceptor 16 is provided with a single-layer type photosensitive layer on a conductive support.
[0150]
【Example】
EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated in more detail, this invention is not limited at all by these Examples.
[0151]
<referenceExample 1>
  A polyamide resin (CM-8000: manufactured by Toray Industries, Inc.) solution dissolved in a methanol / butanol mixed solvent was applied on an aluminum plate support with a doctor blade, and dried at 100 ° C. for 5 minutes to provide a 0.5 μm intermediate layer. . Next, 0.5 g of X-type metal-free phthalocyanine was dispersed by ball milling together with a solution comprising 0.5 g of a polymer charge transport material and 19 g of tetrahydrofuran, and then a pigment composition of 2% by weight, a polymer charge transport material (Exemplary Compound 2D- 09) 80% by weight, an acceptor compound represented by the following structural formula (A1) 18% by weight, silicone oil (KF50: manufactured by Shin-Etsu Chemical Co., Ltd.) 0.001% by weight. A compound, tetrahydrofuran and silicone oil were added to prepare a photoreceptor coating solution having a solid content of 20% by weight. The photoreceptor coating solution thus prepared was applied onto the intermediate layer with a doctor blade and dried at 120 ° C. for 20 minutes to produce a single-layer electrophotographic photoreceptor having a 20 μm-thick photosensitive layer.
[0152]
Embedded image
[0153]
<referenceExample 2>
  referenceIn Example 1, except that the polymer charge transport material was changed to (Exemplary Compound 2D-08).referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0154]
<referenceExample 3>
  referenceIn Example 1, the polymer charge transport material (exemplified compound)5DExcept for -03)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0155]
<referenceExample 4>
  referenceIn Example 1, the acceptor compound is represented by the following structural formula (A2), and the polymer electrotransport material is represented by (example compound)1DExcept for -01)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0156]
Embedded image
[0157]
<referenceExample 5>
  referenceIn Example 1, the polymer charge transport material (exemplified compound)4DExcept for -01)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0158]
<referenceExample 6>
  referenceIn Example 1, the polymer charge transport material (exemplified compound)9DExcept for -01)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0159]
<referenceExample 7>
  referenceIn Example 1, the polymer charge transport material (exemplified compound)6DExcept for -01)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0160]
<referenceExample 8>
  referenceIn Example 1, the polymer charge transport material (exemplified compound)3DExcept for -01)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0161]
<referenceExample 9>
  referenceIn Example 1, the polymer charge transport material (exemplified compound)8DExcept for -01)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0162]
<referenceExample 10>
  referenceIn Example 1, the polymer charge transport material (Exemplified Compound 1)0DExcept for -01)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0163]
<referenceExample 11>
  referenceIn Example 1, the polymer charge transport material (exemplified compound)7DExcept for -01)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0164]
<Example1>
  referenceIn Example 1, except that the polymer charge transport material was changed to (Exemplary Compound 11D-02)referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0165]
<Example2>
  referenceIn Example 1, except that the polymer charge transport material was changed to (Exemplary Compound 11D-04).referenceA single-layer electrophotographic photosensitive member was prepared under the same conditions as in Example 1.
[0166]
<referenceExample12>
  referenceIn Example 1, 2% by weight of the pigment composition, 77.5% by weight of the polymer charge transporting material, 18% by weight of the acceptor compound represented by the structural formula (A1), phenolic compound (in the specific example, No. G2) Polymer charge transport material, acceptor compound, phenolic compound, tetrahydrofuran, and silicone oil were added so that the concentration was 2.5 wt% and silicone oil (KF50: Shin-Etsu Chemical Co., Ltd.) 0.001 wt%. Except that 20% by weight of the photoreceptor coating solution was prepared.referenceA single layer type electrophotographic photosensitive member was prepared in the same manner as in Example 1.
[0167]
<Example3>
  referenceExample 12In Example 1, except that the polymer charge transporting material was changed to (Exemplary Compound 11D-02)referenceExample 12A single-layer electrophotographic photosensitive member was prepared under the same conditions as those described above.
[0168]
<Comparative Example 1>
A polyamide resin (CM-8000: manufactured by Toray Industries, Inc.) solution dissolved in a methanol / butanol mixed solvent was applied on an aluminum plate support with a doctor blade, and dried at 100 ° C. for 5 minutes to provide a 0.5 μm intermediate layer. . Next, 0.5 g of X-type metal-free phthalocyanine was dispersed by ball milling together with a solution of 0.5 g of polycarbonate Z (PC-Z, manufactured by Teijin Chemicals) and 19 g of tetrahydrofuran, and then 2% by weight of pigment composition and PC-Z composition Is 50 wt%, low molecular charge transfer substance represented by the following structural formula (T-1) 30 wt%, acceptor compound represented by (A1) 18 wt%, silicone oil (KF50: manufactured by Shin-Etsu Chemical Co., Ltd.) ) PC-Z, a low molecular charge transport material, an acceptor compound, tetrahydrofuran, and silicone oil were added so as to be 0.001% by weight to prepare a photoreceptor coating solution having a solid content of 20% by weight. The photoreceptor coating solution thus prepared was applied onto the intermediate layer with a doctor blade and dried at 120 ° C. for 20 minutes to produce a single-layer electrophotographic photoreceptor having a 20 μm-thick photosensitive layer.
[0169]
Embedded image
[0170]
  Example aboveAnd reference examplesIn addition, the electrostatic characteristics of the single layer type electrophotographic photosensitive member produced in the comparative example were applied first using an electrostatic copying paper testing apparatus EPA-8200 (manufactured by Kawaguchi Electric) in an environment of 25 ° C./55% RH. After charging for 20 seconds at a voltage of +6 KV, the surface potential V0 (V) after being left in a dark place for 20 seconds was measured, and then the illuminance on the surface of the photoreceptor was 2.5 μW / cm with monochromatic light of 780 nm.²The half-exposure amount Em1 / 2 (μJ / cm) required for the surface potential of the photoreceptor to be 800V to 400V.²) Was measured. Further, the surface of the photoconductor is subjected to a wear test of 3000 revolutions using a CS-5 wear wheel in a Taber abrasion test (manufactured by Toyo Seiki Co., Ltd.) according to the industrial standard JIS K 7204 (1995). It was measured. The results are shown in Table 13.
[0171]
[Table 13]
<Reference example13>
  A polyamide resin (CM-8000: manufactured by Toray Industries, Inc.) solution dissolved in a methanol / butanol mixed solvent was applied on an aluminum plate support with a doctor blade, and dried at 100 ° C. for 5 minutes to provide a 0.5 μm intermediate layer. . Next, 0.5 g of the following azo pigment (P-1) was ball-milled and dispersed together with a solution comprising 0.5 g of the polymer charge transport material and 19 g of tetrahydrofuran, and then the pigment composition was 5% by weight, the polymer charge transport material (example) Compound 2D-09) 80% by weight, acceptor compound represented by the structural formula (A1) 15% by weight, silicone oil (KF50: Shin-Etsu Chemical Co., Ltd.) 0.001% by weight Then, an acceptor compound, tetrahydrofuran, and silicone oil were added to prepare a photoreceptor coating solution having a solid content of 20% by weight. The photoreceptor coating solution thus prepared was applied onto the intermediate layer with a doctor blade and dried at 120 ° C. for 20 minutes to produce a single-layer electrophotographic photoreceptor having a 20 μm-thick photosensitive layer.
[0172]
Embedded image
<referenceExample 14>
  Example1In Example, except that the polymer charge transport material was changed to (Exemplified Compound 2D-08)1 andA single-layer electrophotographic photosensitive member was prepared under the same conditions.
[0173]
<Comparative example 2>
A polyamide resin (CM-8000: manufactured by Toray Industries, Inc.) solution dissolved in a methanol / butanol mixed solvent was applied on an aluminum plate support with a doctor blade, and dried at 100 ° C. for 5 minutes to provide a 0.5 μm intermediate layer. . Next, 0.5 g of the following azo pigment (P-1) was dispersed by ball milling together with a solution consisting of 0.5 g of polycarbonate Z (PC-Z, manufactured by Teijin Chemicals) and 19 g of tetrahydrofuran, and then 5% by weight of pigment composition, PC -Z composition is 50 wt%, low molecular charge transport material represented by the structural formula (T-1) 30 wt%, acceptor compound represented by the structural formula (A1) 15 wt%, silicone oil (KF50) : Manufactured by Shin-Etsu Chemical Co., Ltd.) PC-Z, a low molecular charge transporting material, an acceptor compound, tetrahydrofuran, and silicone oil were added so as to be 0.001% by weight to prepare a photoreceptor coating solution having a solid content of 20% by weight. . The photoreceptor coating solution thus prepared was applied onto the intermediate layer with a doctor blade and dried at 120 ° C. for 20 minutes to produce a single-layer electrophotographic photoreceptor having a 20 μm-thick photosensitive layer.
[0174]
  Example aboveAnd reference examplesIn addition, the electrostatic characteristics of the single layer type electrophotographic photosensitive member produced in the comparative example were applied using an electrostatic copying paper test apparatus EPA-8200 (manufactured by Kawaguchi Electric) in an environment of 25 ° C./55% RH. After charging for 20 seconds at a voltage of +6 KV, the surface potential V0 (V) after being left in a dark place for 20 seconds was measured, and then the illuminance on the surface of the photosensitive member was 2.5 μW / cm with monochromatic light of 650 nm.²The half-exposure amount Em1 / 2 (μJ / cm) required for the surface potential of the photoreceptor to be 800V to 400V.²) Was measured as the sensitivity of the LD light source region. In addition, the surface of the photoconductor is an industrial standard
According to K 7204 (1995), a CS-5 wear wheel was used in a Taber wear test (manufactured by Toyo Seiki Co., Ltd.), and a wear test was conducted at 3000 rpm with a load of 1 kg to measure the amount of wear. The results are shown in Table 14.
[0175]
[Table 14]
<Example>referenceExample 1,referenceThe single layer type electrophotographic photosensitive member of Example 2 and Comparative Example 1 was attached to a drum having a linear velocity of 260 mm / s, and positive charging, exposure, and photoquenching were repeated 5000 times, initial, and after 5000 times, and after exposure. The potential and the post-exposure potential were measured. The results are shown in Table 15.
[0176]
[Table 15]
[0177]
【The invention's effect】
According to the present invention, a single-layer type electrophotographic photosensitive member, a process cartridge, and an electrophotographic film that are excellent in chargeability and sensitivity, particularly excellent in mechanical strength, and have excellent electrostatic characteristics even when the copying process is repeated. A device is provided and contributes significantly to the field of electrophotography.
[Brief description of the drawings]
FIG. 1 is a schematic configuration diagram of an electrophotographic apparatus.
FIG. 2 is a schematic configuration diagram of an electrophotographic apparatus.
FIG. 3 is a schematic configuration diagram of a process cartridge.
[Explanation of symbols]
(In Fig. 1)
1 Photoconductor
2 Static elimination lamp
3 Charger charger
4 Eraser
5 Image exposure section
6 Development unit
7 Charger before transfer
8 Registration roller
9 Transfer paper
10 Transcription charger
11 Separate charger
12 Separating nails
13 Charger before cleaning
14 Fur brush
15 Cleaning blade
(In Figure 2)
21 photoconductor
22 Driving roller
23 Charger charger
24 Image exposure unit
25 Transcription Charger
26 Charger before cleaning
27 Cleaning brush
28 Static elimination light source
(In Fig. 3)
16 photoconductor
17 Charger charger
18 Cleaning brush
19 Image exposure section
20 Development roller

Claims (5)

In the electrophotographic photosensitive member in which a single photosensitive layer is provided on the conductive support directly or through an intermediate layer, the photosensitive layer is composed of at least a charge generating substance, a charge transporting substance and an acceptor compound, and charge transport material Ri charge transport polymers der further single-layer type electrophotographic, wherein the charge transport polymer is a polycarbonate having a triarylamine structure represented by the following general formula (11D) Photoconductor.
[In the formula (11D), Ar ₃₂ , Ar ₃₃ , Ar ₃₅ and Ar ₃₆ represent a substituted or unsubstituted arylene group, and Ar ₃₄ represents a substituted or unsubstituted aryl group. Z represents an arylene group or —Ar ₃₇ —Za—Ar ₃₇ —, and Ar ₃₇ represents a substituted or unsubstituted arylene group. Za represents O, S or an alkylene group. R and R ′ represent a linear or branched alkylene group. h represents 0 or 1. k and j represent composition ratios, 0.1 ≦ k ≦ 1, 0 ≦ j ≦ 0.9, n represents the number of repeating units, and is an integer of 5 to 5000. X is a substituted or unsubstituted aliphatic divalent group, a substituted or unsubstituted cyclic aliphatic divalent group, a substituted or unsubstituted aromatic divalent group, or a divalent group formed by linking these, or Represents a divalent group represented by the following general formula (A ′), general formula (F), and general formula (G). ]
[In the formulas (A ′), (F) and (G), R ₂₄ , R ₂₅ , R ₅₅ and R ₅₆ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a halogen atom. Represents an atom. l and m are each independently an integer of 0 to 4, and s and t are each independently an integer of 0 to 3. When a plurality of R ₂₄ , R ₂₅ , R ₅₅ , and R ₅₆ are present, they may be the same as or different from each other. Y is a single bond, a linear, branched or cyclic alkylene group having 1 to 12 carbon atoms, one or more alkylene groups having 1 to 10 carbon atoms, and one or more oxygen atoms and sulfur atoms. Constructed divalent group, —O—, —S—, —SO—, —SO ₂ —, —CO—, —COO—, —CO—O—Z ₁ —O—CO—, —CO—Z _2. —CO— (wherein Z ₁ and Z ₂ represent a substituted or unsubstituted aliphatic divalent group or a substituted or unsubstituted arylene group), or the following general formula (B) or general formula (H ) To (N). ]
[In formulas (B) and (H) to (N), R ₂₆ and R ₂₇ each independently represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. R ₅₇ , R ₅₈ and R ₆₄ represent a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group. R ₅₉ , R ₆₀ , R ₆₁ , R ₆₂ and R ₆₃ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted group Represents an aryl group. R ₅₈ and R ₅₉ may combine to form a carbocyclic ring having 5 to 12 carbon atoms. R ₆₅ and R ₆₆ represent a single bond or an alkylene group having 1 to 4 carbon atoms. a is an integer of 1 to 20, b is an integer of 1 to 2000, u and w are integers of 0 to 4, and v is 1 or 2. When a plurality of R ₂₆ , R ₂₇ , R ₅₇ and R ₆₄ are present , they may be the same as or different from each other. ] The single-layer electrophotographic photosensitive member according to claim 1, wherein the acceptor compound is a 2,3-diphenylindene compound represented by the following general formula (F1).
[In formula (F1), f ₁ , F ₂ , F _Three , F _Four Represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a cyano group, or a nitro group, and A and B are a hydrogen atom-substituted or unsubstituted aryl group, a cyano group, an alkoxycarbonyl group, or Represents an aryloxycarbonyl group. ] The single-layer electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer contains at least one phenol compound represented by the following general formula (G1).
[In formula (G1), g ₁ ~ G ₈ Represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkoxy group. ] An electrophotographic photosensitive member according to any one of claims 1 to 3, and at least one means selected from the group consisting of a charging means, an image exposing means, a developing means, a transferring means, and a cleaning means, are integrally supported, and electrophotographic A process cartridge which is detachable from the apparatus main body.   An electrophotographic apparatus comprising the electrophotographic photosensitive member according to claim 1, a charging unit, an image exposing unit, a developing unit, and a transfer unit.