CN113874791A - Electrophotographic photoreceptor, process cartridge, and image forming apparatus - Google Patents

Electrophotographic photoreceptor, process cartridge, and image forming apparatus Download PDF

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CN113874791A
CN113874791A CN202080038159.6A CN202080038159A CN113874791A CN 113874791 A CN113874791 A CN 113874791A CN 202080038159 A CN202080038159 A CN 202080038159A CN 113874791 A CN113874791 A CN 113874791A
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general formula
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alkyl group
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岩下裕子
浜崎一也
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Kyocera Document Solutions Inc
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/056—Polyesters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic

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  • General Physics & Mathematics (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

An electrophotographic photoreceptor includes a conductive substrate and a photosensitive layer. The photosensitive layer is a single layer. The photosensitive layer contains a charge generator, a hole transporting agent, an electron transporting agent, a binder resin, and an additive. The binder resin contains a polyarylate resin. The polyarylate resin contains at least 1 repeating unit represented by the general formula (1) and at least 1 repeating unit represented by the general formula (2). The additive contains at least 1 compound among the compounds represented by the general formulae (50), (51) and (52).
Figure DDA0003369025200000011

Description

Electrophotographic photoreceptor, process cartridge, and image forming apparatus
Technical Field
The invention relates to an electrophotographic photoreceptor, a process cartridge and an image forming apparatus.
Background
Electrophotographic photoreceptors are used as image carriers in electrophotographic image forming apparatuses (e.g., printers or multifunction machines). The electrophotographic photoreceptor includes a photosensitive layer. Examples of the electrophotographic photoreceptor include a single-layer type electrophotographic photoreceptor and a laminated type electrophotographic photoreceptor. The single-layer electrophotographic photoreceptor has a single photosensitive layer having a charge generating function and a charge transporting function. The photosensitive layer in the laminated electrophotographic photoreceptor contains a charge generation layer having a charge generation function and a charge transport layer having a charge transport function.
The electrophotographic photoreceptor in the image forming apparatus described in patent document 1 contains a bisphenol Z polycarbonate resin as a binder resin at least in its surface layer.
[ patent document ]
Patent document 1: japanese laid-open patent publication No. 8-234538
Disclosure of Invention
However, the inventors have found that the electrophotographic photoreceptor in the image forming apparatus described in patent document 1 is insufficient in terms of abrasion resistance.
The present invention has been made in view of the above problems, and an object thereof is to provide an electrophotographic photoreceptor having excellent wear resistance and charging stability. Still another object of the present invention is to provide a process cartridge and an image forming apparatus which have excellent durability and can form a high-quality image by having the above-mentioned electrophotographic photoreceptor.
The electrophotographic photoreceptor of the present invention includes a conductive substrate and a photosensitive layer. The photosensitive layer is a single layer. The photosensitive layer contains a charge generator, a hole transporting agent, an electron transporting agent, a binder resin, and an additive. The binder resin contains a polyarylate resin. The polyarylate resin contains at least 1 repeating unit represented by the general formula (1) and at least 1 repeating unit represented by the general formula (2). The additive contains at least 1 compound among the compounds represented by the general formulae (50), (51) and (52).
Figure BDA0003369025180000021
In the general formula (1), R1And R2Both represent methyl. W is a divalent group represented by the general formula (W2). In the general formula (2), X is a divalent group represented by the chemical formula (X1), (X2), (X3), (X4) or (X6).
Figure BDA0003369025180000022
In the general formula (W2), a represents 1 or 2.
Figure BDA0003369025180000031
Figure BDA0003369025180000032
In the general formula (50), R51Represents a halogen atom or a C1-C6 alkyl group substituted with a halogen atom. R52Represents a C1-C10 alkyl group, a C7-C20 aralkyl group or a C6-C22 aryl group. n and m are each independently an integer of 0 to 4. When n represents an integer of 2 to 4, a plurality of R51The same as or different from each other. When m represents an integer of 2 to 4, a plurality of R52The same as or different from each other.
Figure BDA0003369025180000041
In the general formula (51), R53Represents a C3-C10 alkyl group. p represents an integer of 1 to 4. q and r are each independently an integer of 1 to 3. s represents an integer of 1 to 4 inclusive. When p is an integer of 2 to 4, a plurality of R53The same as or different from each other. When s represents an integer of 2 to 4, a plurality of p's are the same or different from each other, a plurality of q's are the same or different from each other, or a plurality of q's are the same or different from each otherr may be the same or different from each other.
Figure BDA0003369025180000042
In the general formula (52), R55Represents a C3-C10 alkyl group. R56Represents a C10-C30 alkyl group. u represents an integer of 1 to 3 inclusive. t represents an integer of 1 to 4 inclusive. When t represents an integer of 2 to 4, a plurality of R55The same as or different from each other.
The process cartridge of the present invention includes the electrophotographic photoreceptor.
An image forming apparatus of the present invention includes an image carrier, a charging device, an exposure device, a developing device, and a transfer device. The image carrier is rotatably provided. The charging device charges the surface of the image carrier to a positive polarity. The exposure device irradiates the charged surface of the image carrier with light to form an electrostatic latent image on the surface of the image carrier. The developing device develops the electrostatic latent image into a toner image. The transfer device transfers the toner image from the image bearing member to a transfer object. The image bearing member is the electrophotographic photoreceptor.
[ Effect of the invention ]
The electrophotographic photoreceptor of the present invention has excellent abrasion resistance and charging stability. Further, the process cartridge and the image forming apparatus of the present invention are provided with the above-mentioned electrophotographic photoreceptor, have excellent durability and can form a high-quality image.
Drawings
Fig. 1 is a partial sectional view of an electrophotographic photoreceptor according to an embodiment of the present invention.
Fig. 2 is a partial sectional view of the electrophotographic photoreceptor according to the embodiment of the present invention.
Fig. 3 is a partial sectional view of the electrophotographic photoreceptor according to the embodiment of the present invention.
Fig. 4 is a cross-sectional view of an example of an image forming apparatus.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments in any way. The present invention can be implemented by appropriately changing the range of the object. Note that, although the description thereof may be omitted as appropriate, the gist of the present invention is not limited thereto. Hereinafter, the compound and its derivatives may be collectively referred to by adding "class" to the compound name. When a "class" is added to a compound name to indicate a polymer name, the repeating unit indicating the polymer is derived from the compound or a derivative thereof.
First, the substituents used in the present specification will be described. Halogen atoms (halo groups) are, for example: fluorine atom (fluoro group), chlorine atom (chloro group), bromine atom (bromo group), and iodine atom (iodo group).
Unless otherwise specified, C1-C10 alkyl, C1-C8 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1 alkyl, C4 alkyl, C8 alkyl, C3-C10 alkyl, C2-C4 alkyl and C3-C5 alkyl are all straight-chain or branched-chain and unsubstituted. C1-C10 alkyl is, for example: methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group, 2-ethylpropyl group, 1-dimethylpropyl group, 1, 2-dimethylpropyl group, 2, 2-dimethylpropyl group, 1, 2-dimethylpropyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 1-dimethylbutyl group, 1, 2-dimethylbutyl group, 1, 3-dimethylbutyl group, 2, 2-dimethylbutyl group, 2, 3-dimethylbutyl group, 3-dimethylbutyl group, 1, 2-trimethylpropyl group, 1,2, 2-trimethylpropyl group, 1-ethylbutyl, 2-ethylbutyl and 3-ethylbutyl, straight-chain and branched-chain heptyl, straight-chain and branched-chain octyl, straight-chain and branched-chain nonyl and straight-chain and branched-chain decyl. Examples of C1-C8 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, C1 alkyl, C4 alkyl, C8 alkyl, C3-C10 alkyl, C2-C4 alkyl and C3-C5 alkyl are each radicals having the corresponding number of carbon atoms in the case of C1-C10 alkyl.
Unless otherwise indicated, C10-C30 alkyl and C15-C25 alkyl are both straight or branched chain and unsubstituted. C10-C30 alkyl is, for example: the alkyl group includes a linear and branched decyl group, a linear and branched undecyl group, a linear and branched dodecyl group, a linear and branched tridecyl group, a linear and branched tetradecyl group, a linear and branched pentadecyl group, a linear and branched hexadecyl group, a linear and branched heptadecyl group, a linear and branched octadecyl group, a linear and branched nonadecyl group, a linear and branched eicosyl group, a linear and branched heneicosyl group, a linear and branched docosyl group, a linear and branched tricosyl group, a linear and branched tetracosyl group, a linear and branched pentacosyl group, and a linear and branched triacontyl group. Examples of C15-C25 alkyl are C15-C25 groups in the case of C10-C30 alkyl.
Unless otherwise indicated, C1-C8 alkoxy, C1-C6 alkoxy and C1-C4 alkoxy are linear or branched and are unsubstituted. C1-C6 alkoxy is, for example: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 2-ethylpropoxy, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2-dimethylpropoxy, 1, 2-dimethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3-dimethylbutoxy, n-butoxy, 2-methylbutoxy, 3-methylpropoxy, 2-methylpropoxy, 1, 2-dimethylbutoxy, 2-dimethylbutoxy, 3-dimethylbutoxy, 1,1, 2-trimethylpropoxy, 1,2, 2-trimethylpropoxy, 1-ethylbutoxy, 2-ethylbutoxy, 3-ethylbutoxy, linear and branched heptyloxy and linear and branched octyloxy. Examples of C1-C6 alkoxy and C1-C4 alkoxy are the radicals having the corresponding number of carbon atoms in the case of C1-C8 alkoxy.
Unless otherwise indicated, both the C6-C22 aryl and the C6-C14 aryl are unsubstituted. C6-C22 aryl is, for example: phenyl, naphthyl, indacenyl (indacenyl), biphenylene (biphenylenyl), acenaphthenyl (acenaphthylene), anthracenyl and phenanthrenyl, tetracenyl (tetracenyl group), tetraphenyl, chrysenyl (chrysenyl group), pyrenyl, triphenylene (triphenylenyl group), benzophenanthrenyl (benzophenanthrenyl group), picenyl (picenyl group), perylenyl (perylene group) and pentaphenyl. C6-C14 aryl is, for example: phenyl, naphthyl, indacenyl, biphenylene, acenaphthenyl, anthracenyl, and phenanthrenyl.
Unless otherwise indicated, C6-C14 aryloxy is unsubstituted. C6-C14 aryloxy is for example: phenoxy, naphthoxy, indacenyloxy (indacenyloxy), biphenylyloxy (biphenylyloxy), acenaphthenyloxy (acenaphthenyloxy), anthracenyloxy, phenanthreneoxy, and fluorenyloxy groups.
Unless otherwise indicated, C2-C6 alkenyl is straight-chain or branched-chain and is unsubstituted. The C2-C6 alkenyl group has 1 to 3 double bonds. C2-C6 alkenyl is, for example: ethenyl, propenyl, butenyl, butadienyl, pentenyl, hexenyl, hexadienyl, and hextripentyl.
Unless otherwise indicated, the C3-C14 heterocyclyl group is unsubstituted. C3-C14 heterocyclyl is, for example: piperidinyl, piperazinyl, (2-or 3-) morpholinyl, thiophenyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, isothiazolyl, isoxazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, furazanyl, pyranyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, 1H-indazolyl, isoindolyl, benzopyranyl, quinolinyl, isoquinolinyl, purinyl, pteridinyl, triazolyl, tetrazolyl, 4H-quinolizinyl, naphthyridinyl, benzofuranyl, 1, 3-benzodioxolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, carbazolyl, phenanthridinyl, acridinyl, phenazinyl, and phenanthrolinyl.
Unless otherwise indicated, both the C7-C20 aralkyl and the C7-C10 aralkyl groups are unsubstituted. C7-C20 aralkyl is, for example, C1-C6 alkyl having C6-C14 aryl substituents. C7-C10 aralkyl is, for example, C1-C4 alkyl with a phenyl substituent.
Unless otherwise indicated, both the C7-C20 aralkyloxy and the C7-C10 aralkyloxy are unsubstituted. C7-C20 aralkyloxy is, for example, C1-C6 alkoxy having C6-C14 aryl substituents. C7-C10 aralkyl is, for example, C1-C4 alkoxy with a phenyl substituent. As described above, the substituents used in the present specification are illustrated.
< electrophotographic photoreceptor >
The present embodiment relates to an electrophotographic photoreceptor (hereinafter, may be referred to as a photoreceptor). The structure of the photoreceptor 1 according to the present embodiment will be described below with reference to fig. 1 to 3. Fig. 1 to 3 each show a partial sectional view of the photoreceptor 1.
As shown in fig. 1, the photoreceptor 1 includes, for example, a conductive substrate 2 and a photosensitive layer 3. The photosensitive layer 3 is a single layer. The photoreceptor 1 is a single-layer electrophotographic photoreceptor having a single photosensitive layer 3.
As shown in fig. 2, the photoreceptor 1 may also include a conductive substrate 2, a photosensitive layer 3, and an intermediate layer 4 (undercoat layer). The intermediate layer 4 is provided between the conductive substrate 2 and the photosensitive layer 3. As shown in fig. 1, the photosensitive layer 3 may be directly on the conductive substrate 2. Alternatively, as shown in fig. 2, the photosensitive layer 3 may be provided on the conductive substrate 2 with the intermediate layer 4 interposed therebetween.
As shown in fig. 3, the photoreceptor 1 may include a conductive substrate 2, a photosensitive layer 3, and a protective layer 5. The protective layer 5 is provided on the photosensitive layer 3. As shown in fig. 1 and 2, the photosensitive layer 3 serves as the outermost surface layer of the photoreceptor 1. Alternatively, as shown in fig. 3, the protective layer 5 may be an outermost surface layer of the photoreceptor 1.
The photosensitive layer 3 contains a charge generator, a hole transporting agent, an electron transporting agent, a binder resin, and an additive.
The thickness of the photosensitive layer 3 is not particularly limited, but is preferably 5 μm to 100 μm, and more preferably 10 μm to 50 μm. As described above, the structure of the photoreceptor 1 is described with reference to fig. 1 to 3. The photoreceptor will be further described below.
(Binder resin)
The photosensitive layer contains a polyarylate resin as a binder resin. The polyarylate resin contains at least 1 repeating unit represented by the general formula (1) and at least 1 repeating unit represented by the general formula (2). Hereinafter, when the polyarylate resin contains at least 1 repeating unit represented by the general formula (1) and at least 1 repeating unit represented by the general formula (2), it may be referred to as a polyarylate resin (PA). The repeating units represented by the general formulae (1) and (2) may be referred to as repeating units (1) and (2), respectively.
Figure BDA0003369025180000101
In the general formula (1), R1And R2Both represent methyl. W is a divalent group represented by the general formula (W2). In the general formula (W2), a represents 1 or 2.
Figure BDA0003369025180000102
In the general formula (2), X is a divalent group represented by the formula (X1), (X2), (X3), (X4) or (X6).
Figure BDA0003369025180000111
The polyarylate resin (PA) has a specific chemical structure. By containing the polyarylate resin (PA) in the photosensitive layer, the abrasion resistance of the photoreceptor can be improved. Further, the polyarylate resin (PA) has a specific chemical structure, and thus the density of the photosensitive layer can be increased. Therefore, a substance (e.g., gas) that lowers the charging potential is less likely to enter the photosensitive layer, and the charging stability of the photoreceptor is improved.
In the general formula (W2), a preferably represents 2. In the general formula (2), X is preferably a divalent group represented by the formula (X1), (X3), (X4) or (X6).
Preferred examples of the repeating unit (1) include: repeating units represented by the formulae (1-1) and (1-2). Hereinafter, the repeating units represented by the chemical formulae (1-1) and (1-2) may be referred to as repeating units (1-1) and (1-2), respectively.
Figure BDA0003369025180000121
Preferable examples of the repeating unit (2) include: a repeating unit represented by the chemical formula (2-X1), (2-X2), (2-X3), (2-X4) and (2-X6). Hereinafter, the repeating units represented by chemical formulae (2-X1), (2-X2), (2-X3), (2-X4) and (2-X6) may be described as repeating units (2-X1), (2-X2), (2-X3), (2-X4) and (2-X6), respectively. Further preferable examples of the repeating unit (2) include: repeating units (2-X1), (2-X3), (2-X4) and (2-X6).
Figure BDA0003369025180000122
An example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (V)) containing the repeating units (1 to 2) and (2 to X3). The polyarylate resin (V) is preferably: a polyarylate resin (hereinafter, referred to as polyarylate resin (V')) having only the repeating units (1-2) and (2-X3) in the repeating units.
Figure BDA0003369025180000131
Another example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (IX)) containing the repeating units (1 to 2) and (2 to X6). The polyarylate resin (IX) is preferably: a polyarylate resin (hereinafter, referred to as polyarylate resin (IX')) having only the repeating units (1-2) and (2-X6) in the repeating units.
Figure BDA0003369025180000132
Another example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (I)) containing the repeating units (1-2), (2-X1) and (2-X4).
Figure BDA0003369025180000141
Another example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (II)) containing the repeating units (1-2), (2-X1) and (2-X3). The polyarylate resin (II) is preferably: a polyarylate resin (hereinafter, referred to as polyarylate resin (II')) having only the repeating units (1-2), (2-X1) and (2-X3) in the repeating units.
Figure BDA0003369025180000142
Another example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (III)) containing the repeating units (1-2), (2-X4) and (2-X3).
Figure BDA0003369025180000143
Another example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (VIII)) containing the repeating units (1-2), (2-X6) and (2-X3).
Figure BDA0003369025180000151
Another example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (VI)) having the repeating units (1-2), (2-X6) and (2-X1).
Figure BDA0003369025180000152
Another example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (X)) containing the repeating units (1-1), (2-X1) and (2-X3).
Figure BDA0003369025180000161
Another example of the polyarylate resin (PA) is a polyarylate resin (hereinafter, referred to as polyarylate resin (XII)) having the repeating units (1-1), (1-2), (2-X1) and (2-X3).
Figure BDA0003369025180000162
Specific examples of the polyarylate resin (PA) are: polyarylate resins represented by chemical formulas (R1) to (R12) (hereinafter, sometimes referred to as polyarylate resins (R1) to (R12), respectively). In addition, in the chemical formulas (R1) to (R12), the right subscript number of each repeating unit means: the percentage (%) of the number of each repeating unit in the polyarylate resin with respect to the total number of the repeating units. The total number of repeating units is the sum of the number of repeating units derived from bisphenol and the number of repeating units derived from dicarboxylic acid.
Figure BDA0003369025180000171
Figure BDA0003369025180000172
Figure BDA0003369025180000181
Figure BDA0003369025180000182
Figure BDA0003369025180000183
Figure BDA0003369025180000191
Figure BDA0003369025180000192
Figure BDA0003369025180000193
Figure BDA0003369025180000201
Figure BDA0003369025180000202
Figure BDA0003369025180000203
Figure BDA0003369025180000211
The polyarylate resin (PA) may contain 1,2 or 3 or more kinds of the repeating unit (1). When the polyarylate resin (PA) contains 2 kinds of the repeating units (1), the ratio of the number of one repeating unit (1) to the total number of one repeating unit (1) and the other repeating unit (1) is preferably 10% or more and 90% or less, more preferably 30% or more and 70% or less, further preferably 40% or more and 60% or less, and particularly preferably 55% or more and 60% or less. In the case where the 2 kinds of repeating units (1) are the repeating units (1-1) and (1-2), one repeating unit (1) is the repeating unit (1-2), and the other repeating unit (1) is the repeating unit (1-1).
The polyarylate resin (PA) may contain 1,2 or 3 or more kinds of the repeating unit (2). When the polyarylate resin (PA) contains 2 kinds of the repeating units (2), the ratio of the number of one repeating unit (2) to the total number of one repeating unit (2) and the other repeating unit (2) is preferably 10% or more and 90% or less, more preferably 30% or more and 80% or less, further preferably 50% or more and 80% or less, and particularly preferably 50% or more and 70% or less. In the case where the 2 kinds of repeating units (2) are the repeating units (2-X3) and (2-X4), one repeating unit (2) is the repeating unit (2-X3), and the other repeating unit (2) is the repeating unit (2-X4). In the case where the 2 kinds of repeating units (2) are the repeating units (2-X1) and (2-X3), one repeating unit (2) is the repeating unit (2-X3), and the other repeating unit (2) is the repeating unit (2-X1).
With respect to the ratio of the number of the above one repeating unit (1) and the ratio of the number of the above one repeating unit (2), the measurement of polyarylate resin (PA) was carried out using a proton nuclear magnetic resonance spectrometer1H-NMR spectrum against the obtained1The ratio can be obtained by calculating the ratio of characteristic peaks for each repeating unit in the H-NMR spectrum.
The polyarylate resin (PA) may contain only the repeating units (1) and (2) or may further contain another repeating unit. In the photosensitive layer, the binder resin may contain only 1 polyarylate resin (PA), or may contain 2 or more polyarylate resins (PA).
In the polyarylate resin (PA), the repeating units derived from bisphenol and the repeating units derived from dicarboxylic acid are adjacent to each other and bonded to each other. The repeating unit derived from bisphenol is, for example, the repeating unit (1). The repeating unit derived from a dicarboxylic acid is, for example, the repeating unit (2). The polyarylate resin (PA) may be, for example, a random copolymer, an alternating copolymer, a periodic copolymer, or a block copolymer.
The viscosity average molecular weight of the polyarylate resin (PA) is preferably 10,000 or more, more preferably 20,000 or more, further preferably 30,000 or more, further preferably 40,000 or more, and particularly preferably 50,000 or more. When the viscosity average molecular weight of the polyarylate resin (PA) is 10,000 or more, the abrasion resistance of the photoreceptor can be improved. On the other hand, the viscosity average molecular weight of the polyarylate resin (PA) is preferably 80,000 or less, and more preferably 70,000 or less. When the viscosity average molecular weight of the polyarylate resin (PA) is 80,000 or less, the polyarylate resin (PA) is easily soluble in a solvent for forming the photosensitive layer.
The method for producing the polyarylate resin (PA) is not particularly limited. The method for producing the polyarylate resin (PA) is, for example: a method for polycondensation of bisphenol (constituting repeating units derived from bisphenol) and dicarboxylic acid (constituting repeating units derived from dicarboxylic acid). The polycondensation may employ a well-known synthesis method (for example, solution polymerization, melt polymerization, or interfacial polymerization).
Examples of the bisphenol (used to constitute the repeating unit derived from bisphenol) include: a compound represented by the general formula (BP-1). Examples of dicarboxylic acids (used to form the repeating units derived from dicarboxylic acids) include: a compound represented by the general formula (DC-2). R in the formula (BP-1)1、R2And W and R in the general formula (1)1、R2And W have the same meaning. X in the general formula (DC-2) has the same meaning as X in the general formula (2).
Figure BDA0003369025180000231
In the polycondensation of bisphenol and dicarboxylic acid, one or both of a base and a catalyst may be added. An example of a base is sodium hydroxide. Examples of catalysts are: benzyl tributyl ammonium chloride, ammonium bromide, quaternary ammonium salts, triethylamine and trimethylamine.
The photosensitive layer may further contain a binder resin (hereinafter, referred to as another binder resin) other than the polyarylate resin (PA) in addition to the polyarylate resin (PA). Other binding resins are, for example: thermoplastic resins (more specifically, polycarbonate resins, styrene-butadiene copolymers, styrene-acrylonitrile copolymers, styrene-maleic acid copolymers, styrene-acrylic acid copolymers, polyethylene resins, ethylene-vinyl acetate copolymers, chlorinated polyethylene resins, polyvinyl chloride resins, polypropylene resins, ionomers, vinyl chloride-vinyl acetate copolymers, polyester resins, alkyd resins, polyamide resins, polyurethane resins, polysulfone resins, diallyl phthalate resins, ketone resins, polyvinyl butyral resins, and polyether resins), thermosetting resins (more specifically, silicone resins, epoxy resins, phenol resins, urea resins, melamine resins, and other crosslinking thermosetting resins), and light-curing resins (more specifically, epoxy-acrylic resins and polyurethane-acrylic copolymers).
(additives)
The photosensitive layer contains at least 1 compound of the compounds represented by the general formulae (50), (51) and (52) as an additive. That is, the additive in the photosensitive layer contains at least 1 compound selected from the group consisting of the compounds represented by the general formulae (50), (51), and (52). The compound represented by the general formula (50) is a benzotriazole ultraviolet absorber. Hereinafter, the compound represented by the general formula (50) may be referred to as an ultraviolet absorber (50). The compounds represented by the general formulae (51) and (52) are both hindered phenol type antioxidants. Hereinafter, the compounds represented by the general formulae (51) and (52) may be referred to as antioxidants (51) and (52), respectively. The compounds represented by the general formulae (50), (51) and (52) may be collectively referred to as "specific additives".
By incorporating specific additives into the photosensitive layer, the first and second benefits shown below are obtained.
The first advantage is explained. The charge stability of the photoreceptor can be improved by containing at least 1 of the specific additives in the photosensitive layer. The charge stability of the photoreceptor means: the charge potential of the photoreceptor is not easily lowered even after a large amount of printing. The reason why the charging stability of the photoreceptor can be improved is presumed as follows. When the photoreceptor is charged, a recombination reaction of ions and electrons occurs, thereby generating ultraviolet rays. The hole transporting agent and the like may be deteriorated due to the generated ultraviolet rays. By incorporating the ultraviolet absorber (50) into the photosensitive layer, deterioration of the hole transport agent and the like by ultraviolet rays can be suppressed, and the charging stability of the photoreceptor can be improved. Further, when radicals are generated in the photosensitive layer, residual charges are generated by capturing the radicals in charge transport in the photosensitive layer, and thus it is difficult to charge the surface of the photosensitive layer. The antioxidants (51) and (52) trap radicals generated in the photosensitive layer, thereby being able to reduce the radicals in the photosensitive layer. Therefore, the charging stability of the photoreceptor is improved.
The second benefit is explained. As described above, by containing the polyarylate resin (PA) in the photosensitive layer, the abrasion resistance of the photoreceptor is improved. The specific additive has a specific chemical structure, and thus the photoreceptor abrasion resistance improved by the polyarylate resin (PA) can be maintained without being lowered.
Next, the specific additives will be described one by one in order. The ultraviolet absorber (50) is represented by the following general formula (50).
Figure BDA0003369025180000251
In the general formula (50), R51Represents a halogen atom or a C1-C6 alkyl group substituted with a halogen atom. R52Represents a C1-C10 alkyl group, a C7-C20 aralkyl group or a C6-C22 aryl group. n and m are each independently an integer of 0 to 4. When n represents an integer of 2 to 4, a plurality of R51(i.e., R)51The indicated groups) are the same as or different from each other. When m represents an integer of 2 to 4, a plurality of R52(i.e., R)52The indicated groups) are the same as or different from each other.
R in the general formula (50)51When the alkyl group represents a C1-C6 alkyl group substituted with a halogen atom, the alkyl group is preferably a C1-C3 alkyl group substituted with a halogen atom, and more preferably a C1-C3 alkyl group substituted with a chlorine atom. R51When a halogen atom is represented, a fluorine atom or a chlorine atom is preferable, and a chlorine atom is more preferable.
R in the general formula (50)52When the alkyl group represents a C1-C10 group, the alkyl group is preferably a C1-C8 alkyl group, more preferably a C1 alkyl group, a C4 alkyl group or a C8 alkyl group, and still more preferably a methyl group, a tert-butyl group or a 1,1,3, 3-tetramethylbutyl group. R52When it represents a C7-C20 aralkyl group, it is preferably a C7-C10 aralkyl group. R52When the aryl group is a C6-C22 aryl group, the aryl group is preferably a C6-C14 aryl group.
In the general formula (50), R51Preferably represents a halogen atom. R52Preferably represents a C1-C10 alkyl group. n preferably represents 0 or 1. m preferably represents 1 or 2. In the case where m represents 2, 2R52May be the same or different from each other.
Preferable examples of the ultraviolet absorber (50) include: compounds represented by the general formulae (50-1) and (50-2). R in the formula (50-1)51And R52And R in the general formula (50)51And R52Have the same meaning. 2R in the formula (50-1)52May be the same or different from each other. R in the formula (50-2)52And R in the general formula (50)52Have the same meaning.
Figure BDA0003369025180000261
The antioxidant (51) is represented by the following general formula (51).
Figure BDA0003369025180000262
In the general formula (51), R53Represents a C3-C10 alkyl group. p represents an integer of 1 to 4. q and r are each independently an integer of 1 to 3. s represents an integer of 1 to 4 inclusive. When p is an integer of 2 to 4, a plurality of R53(i.e., R)53The indicated groups) are the same as or different from each other. When s represents an integer of 2 or more and 4 or less, p (i.e., an integer represented by p) may be the same as or different from each other, q (i.e., an integer represented by q) may be the same as or different from each other, and r (i.e., an integer represented by r) may be the same as or different from each other.
R in the general formula (51)53When the alkyl group represents a C3-C10 group, the alkyl group is preferably a C3-C5 alkyl group, more preferably a C3-C5 branched alkyl group, and particularly preferably a tert-butyl group.
In the general formula (51), p preferably represents an integer of 1 to 3, more preferably 2.
In the general formula (51), q and r are each independently preferably 1 or 2. q more preferably represents 2. More preferably, r represents 1.
In the general formula (51), s preferably represents 3 or 4, more preferably 4.
In the general formula (51), R53Preferably represents a C3-C10 alkyl group. p preferably represents 2. q preferably represents 2. r preferably represents 1. s preferably represents 4. 8R53The same as or different from each other.
Preferable examples of the antioxidant (51) include: a compound represented by the general formula (51-3). R in the formula (51-3)53Q and R are each independently of R in the general formula (51)53Q and r have the same meaning. 8R in the formula (51-3)53May be the same or different from each other. The integers represented by 4 q in the general formula (51-3) may be the same or different from each other. The integers represented by 4 r in the general formula (51-3) may be the same as or different from each other.
Figure BDA0003369025180000281
The antioxidant (52) is represented by the following general formula (52).
Figure BDA0003369025180000282
In the general formula (52), R55Represents a C3-C10 alkyl group. R56Represents a C10-C30 alkyl group. u represents an integer of 1 to 3 inclusive. t represents an integer of 1 to 4 inclusive. When t represents an integer of 2 to 4, a plurality of R55The same as or different from each other.
In the general formula (52), R55When the alkyl group represents a C3-C10 group, the alkyl group is preferably a C3-C5 alkyl group, more preferably a C3-C5 branched alkyl group, and particularly preferably a tert-butyl group.
In the general formula (52), R56When it represents a C10-C30 alkyl group, it is preferably a C15-C25 alkyl group, and more preferably an octadecyl group.
In the general formula (52), t preferably represents an integer of 1 to 3, more preferably 2.
In the general formula (52), u preferably represents 1 or 2, more preferably represents 2.
In the general formula (52), R is as defined above55Represents C3-C10 alkyl, R56Represents a C10-C30 alkyl group. u preferably represents 2. t preferably represents 2. When t represents 2, 2R55(i.e., R)55The indicated groups) are the same as or different from each other.
Preferable examples of the antioxidant (52) includeA compound represented by the general formula (52-4) is shown. R in the general formula (52-4)55、R56And u are each independently of R in the general formula (52)55、R56And u have the same meaning. 2R in the formula (52-4)55May be the same or different from each other.
Figure BDA0003369025180000291
In order to improve the abrasion resistance and charging stability of the photoreceptor, at least 1 compound of the specific compounds is preferably at least 1 compound (i.e., at least 1 compound selected from the group consisting of compounds represented by chemical formulae (AD1), (AD2), (AD3), and (AD 4)) of the compounds represented by chemical formulae (AD1), (AD2), (AD3), and (AD 4). Hereinafter, the compounds represented by chemical formulas (AD1), (AD2), (AD3), and (AD4) may be described as an ultraviolet absorber (AD1), an ultraviolet absorber (AD2), an antioxidant (AD3), and an antioxidant (AD4), respectively.
Figure BDA0003369025180000301
Figure BDA0003369025180000302
The ultraviolet absorbers (AD1) and (AD2) are each a preferable example of the ultraviolet absorber (50). Antioxidant (AD3) is a preferred example of antioxidant (51). Antioxidant (AD4) is a preferred example of antioxidant (52).
In order to improve the abrasion resistance and charging stability of the photoreceptor, the content of the specific additive (at least 1 selected additive) is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, and still more preferably 3 parts by mass or more, per 100 parts by mass of the binder resin. For the same reason, the content of the specific additive (selected at least 1 additive) is preferably 15 parts by mass or less, more preferably 10 parts by mass or less, and still more preferably 7 parts by mass or less, with respect to 100 parts by mass of the binder resin. When the photosensitive layer contains at least 2 additives of the specific additives, the content thereof means the total content of the at least 2 additives of the specific additives.
The photosensitive layer contains, for example, 1,2 or 3 of specific additives. The photosensitive layer preferably contains 1 of the specific additives. In the photosensitive layer, the additive may contain only at least 1 of the specific additives, or may further contain an additive other than the specific additive (hereinafter, sometimes referred to as another additive).
Other additives are, for example: singlet quenchers, softeners, surface modifiers, extenders, thickeners, dispersion stabilizers, waxes, donors, surfactants, plasticizers, sensitizers, electron acceptor compounds and leveling agents.
(Charge generating agent)
Examples of charge generators are: phthalocyanine pigments, perylene pigments, disazo pigments, trisazo pigments, dithione-pyrrolopyrrole (dithioketo-pyrrozole) pigments, metal-free naphthalocyanine pigments, metal naphthalocyanine pigments, squaric acid pigments, indigo pigments, azulene pigments, cyanine pigments, powders of inorganic photoconductive materials (e.g., selenium-tellurium, selenium-arsenic, cadmium sulfide, and amorphous silicon), pyran pigments, anthanthrone pigments, triphenylmethane pigments, threne pigments, toluidine pigments, pyrazoline pigments, and quinacridone pigments. The photosensitive layer may contain only 1 kind of charge generating agent, or may contain 2 or more kinds.
Examples of phthalocyanine pigments are: metal-free phthalocyanines and metal phthalocyanines. The metal phthalocyanines are, for example: oxytitanium phthalocyanine, hydroxygallium phthalocyanine and chlorogallium phthalocyanine. The metal-free phthalocyanine is represented by the chemical formula (CGM-1). The oxytitanium phthalocyanine is represented by the chemical formula (CGM-2).
Figure BDA0003369025180000321
Figure BDA0003369025180000322
The phthalocyanine pigment may be crystalline or amorphous. The metal phthalocyanine-free crystals are, for example: an X-type crystal of metal-free phthalocyanine (hereinafter, sometimes referred to as X-type metal-free phthalocyanine). Crystals of oxytitanium phthalocyanine are, for example: crystal of oxytitanium phthalocyanine of α type, β type and Y type (hereinafter, sometimes referred to as "α type", "β type" and "Y type", respectively).
For example, in a digital optical image forming apparatus (for example, a laser printer or a facsimile machine using a light source such as a semiconductor laser), it is preferable to use a photoreceptor having sensitivity in a wavelength region of 700nm or more. The charge generating agent is preferably a phthalocyanine-based pigment, more preferably a metal-free phthalocyanine or oxytitanium phthalocyanine, still more preferably an X-type metal-free phthalocyanine or Y-type oxytitanium phthalocyanine, and particularly preferably a Y-type oxytitanium phthalocyanine, from the viewpoint of having a high quantum yield in a wavelength region of 700nm or more.
The Y-type oxytitanium phthalocyanine has a main peak at 27.2 ° of the bragg angle (2 θ ± 0.2 °) in the CuK α characteristic X-ray diffraction spectrum, for example. The main peak in the CuK α characteristic X-ray diffraction spectrum means a peak having a first or second large intensity in a range where the bragg angle (2 θ ± 0.2 °) is 3 ° or more and 40 ° or less. In the CuK α characteristic X-ray diffraction spectrum, the Y-type oxytitanium phthalocyanine has no peak at 26.2 ℃.
The CuK α characteristic X-ray diffraction spectrum can be measured, for example, by the following method. First, a sample (oxytitanium phthalocyanine) was filled in a sample holder of an X-ray diffraction apparatus ("RINT (Japanese registered trademark) 1100" manufactured by Rigaku Corporation) at X-ray tube Cu, tube voltage 40kV, tube current 30mA and CuK α characteristic X-ray wavelength
Figure BDA0003369025180000331
The X-ray diffraction spectrum was measured. The measurement range (2 θ) is, for example, 3 ° to 40 ° (start angle 3 ° and stop angle 40 °), and the scanning speed is, for example, 10 °/min. And determining a main peak according to the obtained X-ray diffraction spectrum, and reading the Bragg angle of the main peak.
The content of the charge generating agent is preferably 0.1 part by mass or more and 50 parts by mass or less, and more preferably 0.5 part by mass or more and 5 parts by mass or less, with respect to 100 parts by mass of the binder resin.
(Electron transport agent)
Examples of electron transport agents are: quinone compounds, imide compounds, hydrazone compounds, malononitrile compounds, thiopyran compounds, trinitrothioxanthone compounds, 3,4,5, 7-tetranitro-9-fluorenone compounds, dinitroanthracene compounds, dinitroacridine compounds, tetracyanoethylene, 2,4, 8-trinitrothioxanthone, dinitrobenzene, dinitroacridine, succinic anhydride, maleic anhydride and dibromomaleic anhydride. Quinone compounds are for example: diphenoquinone compounds, azoquinone compounds, anthraquinone compounds, naphthoquinone compounds, nitroanthraquinone compounds and dinitroanthraquinone compounds. The photosensitive layer may contain only 1 kind of electron-transporting agent, or may contain 2 or more kinds of electron-transporting agents.
Preferred examples of the electron-transporting agent include compounds represented by the following general formulae (10), (11), (12), (13) and (14) (hereinafter, sometimes referred to as the electron-transporting agents (10), (11), (12), (13) and (14), respectively) in order to improve the abrasion resistance and charging stability of the photoreceptor.
Figure BDA0003369025180000341
In the general formula (10), Q1、Q2、Q3And Q4Each independently represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C14 aryl group or a C7-C20 aralkyl group.
In the general formula (10), Q1、Q2、Q3And Q4Each independently preferably represents a hydrogen atom or a C1-C6 alkyl group. More preferably: q1And Q4Each independently represents a C1-C6 alkyl group, Q2And Q3Represents a hydrogen atom. Q1、Q2、Q3And Q4When it represents a C1-C6 alkyl group, it is preferably a C1-C5 alkyl group, and more preferably a 1, 1-dimethylpropyl group.
In the general formula (11), Q5Represents a C1-C6 alkyl group or a C6-C14 aryl group. Q6Represents a C1-C6 alkyl group, a C6-C14 aryl group, a C1-C6 alkoxy group, a C7-C20 aralkyl groupA C6-C14 aryloxy group or a C7-C20 aralkyloxy group. Q7Represents a C1-C6 alkyl group. v represents an integer of 0 to 4.
In the general formula (11), Q5Preferably represents a C6-C14 aryl group, more preferably represents a phenyl group. Q6Preferably represents a C7-C20 aralkyloxy group, more preferably represents a C7-C10 aralkyloxy group, and still more preferably represents a benzyloxy group. v preferably represents 0.
In the general formula (12), Q8And Q9Independently of one another, represents a C6-C14 aryl group having at least one C1-C6 alkyl substituent or an unsubstituted C6-C14 aryl group.
In the general formula (12), Q8And Q9Each independently preferably represents a C6-C14 aryl group having 2 or more and 5 or less (e.g., 2) C1-C6 alkyl substituents, more preferably represents a phenyl group having 2 or more and 5 or less (e.g., 2) C1-C3 alkyl substituents, still more preferably represents an ethylmethylphenyl group, and particularly preferably represents a 2-ethyl-6-methylphenyl group.
In the general formula (13), Q10、Q11、Q12And Q13Each independently represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a C6-C14 aryl group, a C7-C20 aralkyl group or a C3-C14 heterocyclic group.
In the general formula (13), Q10、Q11、Q12And Q13Each independently preferably represents a C1-C6 alkyl group, more preferably represents a C1-C4 alkyl group, and still more preferably represents a methyl group or a tert-butyl group.
In the general formula (14), Q14、Q15And Q16Independently of one another, a C1-C6 alkyl group, a C6-C14 aryl group substituted with a halogen atom, or an unsubstituted C6-C14 aryl group.
In the general formula (14), Q14And Q15Each independently preferably represents a C1-C6 alkyl group, more preferably a C1-C4 alkyl group, and still more preferably a tert-butyl group. Q16Preferably represents a C6-C14 aryl group substituted with a halogen atom, more preferably represents a phenyl group substituted with a halogen atom, still more preferably represents a chlorophenyl group, and particularly preferably represents a 4-chlorophenyl group.
Further preferable examples of the electron transport agent include compounds represented by chemical formulas (ET1), (ET2), (ET3), (ET4), and (ET5) (hereinafter, sometimes referred to as electron transport agents (ET1), (ET2), (ET3), (ET4), and (ET5), respectively) in order to improve abrasion resistance and charge stability of the photoreceptor.
Figure BDA0003369025180000361
The electron transport agent (ET1) is a preferred example of the electron transport agent (10). The electron transport agent (ET2) is a preferred example of the electron transport agent (11). The electron transport agent (ET3) is a preferred example of the electron transport agent (12). The electron transport agent (ET4) is a preferred example of the electron transport agent (13). The electron transport agent (ET5) is a preferred example of the electron transport agent (14).
The content of the electron-transporting agent is preferably 5 parts by mass or more and 150 parts by mass or less, and more preferably 10 parts by mass or more and 50 parts by mass or less, with respect to 100 parts by mass of the binder resin.
(hole transport agent)
Hole transporters are for example: oxadiazole compounds (e.g., 2, 5-bis (4-methylaminophenyl) -1,3, 4-oxadiazole), styrene compounds (e.g., 9- (4-diethylaminostyryl) anthracene), carbazole compounds (e.g., polyvinylcarbazole), organopolysilane compounds, pyrazoline compounds (e.g., 1-phenyl-3- (p-dimethylaminophenyl) pyrazoline), hydrazone compounds, indole compounds, oxazole compounds, isoxazole compounds, thiazole compounds, thiadiazole compounds, imidazole compounds, pyrazole compounds, and triazole compounds. The photosensitive layer may contain only 1 kind of hole-transporting agent, or may contain 2 or more kinds of hole-transporting agents.
Preferred examples of the hole-transporting agent for improving the abrasion resistance and the charging stability of the photoreceptor include compounds represented by the following general formulae (20), (21), (22), (23), (24), (25), (26) and (27) (hereinafter, sometimes referred to as the hole-transporting agents (20), (21), (22), (23), (24), (25), (26) and (27), respectively).
Figure BDA0003369025180000381
Figure BDA0003369025180000391
In the general formula (20), R11、R12、R13、R14、R15And R16Each independently represents a C1-C8 alkyl group or a phenyl group. R17And R18Each independently represents a hydrogen atom, a C1-C8 alkyl group or a phenyl group. b1, b2, b3 and b4 are independent of each other and each represents an integer of 0 to 5 inclusive. b5 and b6 are each independently an integer of 0 to 4. d and e are each independently 0 or 1.
In the general formula (20), when b1 represents an integer of 2 to 5, a plurality of R11The same or different from each other. b2 represents an integer of 2 to 5 inclusive, a plurality of R12The same or different from each other. b3 represents an integer of 2 to 5 inclusive, a plurality of R13The same or different from each other. b4 represents an integer of 2 to 5 inclusive, a plurality of R14The same or different from each other. b5 represents an integer of 2 to 4 inclusive, a plurality of R15The same or different from each other. b6 represents an integer of 2 to 4 inclusive, a plurality of R16The same or different from each other.
In the general formula (20), R11、R12、R13、R14、R15And R16Each independently preferably represents a C1-C8 alkyl group, more preferably a C1-C3 alkyl group, and still more preferably a methyl group or an ethyl group. R17And R18Preferably represents a hydrogen atom. b1, b2, b3 and b4 are each independently an integer of 0 to 2. b5 and b6 preferably represent 0. As described above, d and e are each independently 0 or 1.
In the general formula (21), R20Represents a hydrogen atom, a C1-C8 alkyl group, a C1-C8 alkoxy group, a phenyl group having a C1-C8 alkyl substituent, or an unsubstituted phenyl group. R21、R22And R23Independently of one another, represents a C1-C8 alkyl group or a C1-C8 alkoxy group. f1, f2 and f3 are each independently an integer of 0 to 5. f4 represents 0 or 1.
In the general formula (21), when f1 represents an integer of 2 to 5, a plurality of R21The same or different from each other. f2 represents an integer of 2 to 5 inclusive, a plurality of R22The same or different from each other. f3 represents an integer of 2 to 5 inclusive, a plurality of R23The same or different from each other.
In the general formula (21), R20Preferably represents a phenyl group having a C1-C8 alkyl substituent or an unsubstituted phenyl group, more preferably an unsubstituted phenyl group. R21、R22And R23Each independently preferably represents a C1-C8 alkyl group, more preferably a C1-C3 alkyl group, and still more preferably a methyl group. f1, f2 and f3 are each independently, preferably 0 or 1. As described above, f4 represents 0 or 1.
In the general formula (22), R31、R32、R33、R34And R35Independently of one another, represents a C1-C8 alkyl group or a C1-C8 alkoxy group. g1, g2, g3, g4 and g5 are each independently an integer of 0 to 5.
In the general formula (22), when g1 represents an integer of 2 to 5, a plurality of R31The same or different from each other. g2 represents an integer of 2 to 5 inclusive, a plurality of R32The same or different from each other. g3 represents an integer of 2 to 5 inclusive, a plurality of R33The same or different from each other. g4 represents an integer of 2 to 5 inclusive, a plurality of R34The same or different from each other. g5 represents an integer of 2 to 5 inclusive, a plurality of R35The same or different from each other.
In the general formula (22), R31、R32、R33、R34And R35Each independently preferably represents a C1-C8 alkyl group, more preferably a C1-C3 alkyl group, and still more preferably a methyl group. g1, g2, g3, g4 and g5 preferably represent 1.
In the general formula (23), R41、R42、R43、R44、R45And R46Are independent from each other and are provided with a plurality of groups,represents a C1-C8 alkyl group, a phenyl group or a C1-C8 alkoxy group. h1, h2, h4 and h5 are independent of each other and each represents an integer of 0 to 5. h3 and h6 are independent of each other and each represents an integer of 0 to 4.
In the general formula (23), when h1 represents an integer of 2 to 5, a plurality of R41The same or different from each other. h2 represents an integer of 2 to 5 inclusive, and R's are several42The same or different from each other. h4 represents an integer of 2 to 5 inclusive, and R's are several44The same or different from each other. h5 represents an integer of 2 to 5 inclusive, and R's are several45The same or different from each other. h3 represents an integer of 2 to 4, a plurality of R43The same or different from each other. h6 represents an integer of 2 to 4, a plurality of R46The same or different from each other.
In the general formula (23), R41、R42、R43、R44、R45And R46Each independently preferably represents a C1-C8 alkyl group, more preferably a C1-C3 alkyl group, and still more preferably a methyl group or an ethyl group. h1, h2, h4 and h5 are each independently an integer of 0 to 2. h3 and h6 preferably represent 0.
In the general formula (24), R61、R62And R63Each independently represents a C1-C8 alkyl group. R64、R65And R66Each independently represents a hydrogen atom or a C1-C8 alkyl group.
In the general formula (24), R61、R62And R63Each independently preferably represents a C1-C8 alkyl group, more preferably a C1-C3 alkyl group, and still more preferably a methyl group. R64、R65And R66Preferably represents a hydrogen atom.
In the general formula (25), R71、R72、R73And R74Each independently represents a C1-C8 alkyl group. j1, j2, j3 and j4 are independent of each other and each represents an integer of 0 to 5. j5 represents 0 or 1.
In the general formula (25), when j1 represents an integer of 2 to 5, a plurality of R71The same or different from each other. j2 represents an integer of 2 to 5, and R' s72Are connected with each otherThe same or different. j3 represents an integer of 2 to 5, and R' s73The same or different from each other. j4 represents an integer of 2 to 5, and R' s74The same or different from each other.
In the general formula (25), R71、R72、R73And R74Each independently preferably represents a C1-C3 alkyl group, more preferably a methyl or ethyl group. j1, j2, j3 and j4 are each independently, preferably 0 or 1. As described above, j5 represents 0 or 1.
In the general formula (26), R81、R82And R83Independently of one another, represents C1-C8 alkyl, phenyl or C1-C8 alkoxy. R84And R85Each independently represents a phenyl group having a C1-C8 alkyl substituent, an unsubstituted phenyl group, a hydrogen atom, a C1-C8 alkyl group or a C1-C8 alkoxy group. k1, k2, and k3 are each independently an integer of 0 to 5. k4 and k5 are independent of each other and represent 1 or 2.
In the general formula (26), when k1 represents an integer of 2 to 5, a plurality of R81The same or different from each other. When k2 represents an integer of 2 to 5, a plurality of R82The same or different from each other. When k3 represents an integer of 2 to 5, a plurality of R83The same or different from each other.
In the general formula (26), R81、R82And R83Each independently preferably represents a C1-C8 alkyl group, more preferably a C1-C6 alkyl group, and still more preferably a methyl group, an ethyl group or an n-butyl group. R84And R85Preferably represents a hydrogen atom. k1, k2 and k3 are each independently preferably an integer of 0 to 2. As described above, k4 and k5 are independent of each other and represent 1 or 2.
In the general formula (27), R91、R92And R93Each independently represents a C1-C8 alkyl group. R94Represents a C1-C8 alkyl group or a hydrogen atom. v1, v2 and v3 are independent of each other and each represents an integer of 0 to 5 inclusive.
In the general formula (27), when v1 represents an integer of 2 to 5, a plurality of R' s91The same or different from each other. When v2 represents an integer of 2 to 5, a plurality of R92The same or different from each other. When v3 represents an integer of 2 to 5, a plurality of R93The same or different from each other.
In the general formula (27), R94Preferably represents a hydrogen atom. v1, v2 and v3 preferably represent 0.
Further preferable examples of the electron transport agent for improving the abrasion resistance and charge stability of the photoreceptor include compounds represented by chemical formulae (HT1), (HT2), (HT3), (HT4), (HT5), (HT6), (HT7), (HT8), (HT9), (HT10), (HT11), (HT12), (HT13), and (HT14) (hereinafter, sometimes referred to as hole transport agents (HT1), (HT2), (HT3), (HT4), (HT5), (HT6), (HT7), (HT8), (HT9), (HT10), (HT11), (HT12), (HT13), and (HT 14)).
Figure BDA0003369025180000441
Figure BDA0003369025180000451
Figure BDA0003369025180000461
Further, both the hole-transporting agents (HT1) and (HT2) are preferable examples of the hole-transporting agent (20). Both the hole-transporting agents (HT3) and (HT4) are preferred examples of the hole-transporting agent (21). The hole-transporting agent (HT5) is a preferred example of the hole-transporting agent (22). Both the hole-transporting agents (HT6) and (HT7) are preferred examples of the hole-transporting agent (23). The hole-transporting agent (HT8) is a preferred example of the hole-transporting agent (24). The hole-transporting agents (HT9), (HT10) and (HT11) are preferred examples of the hole-transporting agent (25). Both hole-transporting agents (HT12) and (HT13) are preferred examples of hole-transporting agents (26). The hole-transporting agent (HT14) is a preferred example of the hole-transporting agent (27).
The content of the hole transporting agent is preferably 10 parts by mass or more, more preferably 50 parts by mass or more, and further preferably 65 parts by mass or more, with respect to 100 parts by mass of the binder resin. The content of the hole transporting agent is preferably 300 parts by mass or less, more preferably 100 parts by mass or less, and further preferably 75 parts by mass or less, with respect to 100 parts by mass of the binder resin.
(combination of materials)
In order to improve the abrasion resistance and charging stability of the photoreceptor, the combination of the additive and the binder resin is preferably each of combination nos. D1 to D27 in table 1. For the same reason, it is preferable that: the combination of the additive and the binder resin was each of combination Nos. D1 to D27 in Table 1, and the charge generating agent was Y-type oxytitanium phthalocyanine.
[ TABLE 1 ]
Figure BDA0003369025180000471
In order to improve the abrasion resistance and charging stability of the photoreceptor, the combination of the hole transporting agent, the additive, and the binder resin is preferably each of combination nos. E1 to E53 in table 2. For the same reason, it is preferable that: the combination of the hole transporting agent, the additive and the binder resin is each of combination nos. E1 to E53 in table 2, and the charge generating agent is Y-type oxytitanium phthalocyanine.
[ TABLE 2 ]
Figure BDA0003369025180000481
In order to improve the abrasion resistance and charging stability of the photoreceptor, the combination of the hole transporting agent, the electron transporting agent, the additive and the binder resin is preferably each of combinations No. F1 to F61 in table 3. For the same reason, it is preferable that: the combination of the hole transporting agent, the electron transporting agent, the additive and the binder resin is each of combination nos. F1 to F61 in table 3, and the charge generating agent is Y-type oxytitanium phthalocyanine.
[ TABLE 3 ]
Figure BDA0003369025180000501
In tables 1 to 3, "No." represents "combination No.", "HTM" represents "hole transport agent", "ETM" represents "electron transport agent", and "resin" represents polyarylate resin.
(conductive substrate)
The conductive substrate is not particularly limited as long as it can be used as a conductive substrate of a photoreceptor. The conductive substrate may be formed of a conductive material at least on the surface portion thereof. An example of a conductive substrate is: a conductive substrate made of a conductive material. Another example of a conductive substrate is: a conductive substrate coated with a conductive material. The conductive material is, for example: aluminum, iron, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel, and brass. These conductive materials may be used alone, or 2 or more kinds (for example, as an alloy) may be used in combination. Among these conductive materials, aluminum or an aluminum alloy is preferable from the viewpoint of good charge transfer from the photosensitive layer to the conductive substrate.
The shape of the conductive substrate is appropriately selected according to the structure of the image forming apparatus. The shape of the conductive substrate is, for example: sheet and drum. The thickness of the conductive substrate is appropriately selected according to the shape of the conductive substrate.
(intermediate layer)
The intermediate layer (undercoat layer) contains, for example, inorganic particles and a resin (resin for intermediate layer) used in the intermediate layer. It can be considered that: the presence of the intermediate layer allows smooth current flow to be generated when the photoreceptor is exposed, while maintaining an insulating state to such an extent that leakage current can be suppressed, thereby suppressing an increase in resistance.
The inorganic particles are, for example: particles of metals (e.g., aluminum, iron, and copper), particles of metal oxides (e.g., titanium dioxide, aluminum oxide, zirconium oxide, tin oxide, and zinc oxide), and particles of non-metal oxides (e.g., silicon dioxide). These inorganic particles may be used alone or in combination of 2 or more.
Examples of the resin for the intermediate layer are the same as those of the binder resin described above. In order to form the intermediate layer and the photosensitive layer well, the resin for the intermediate layer is preferably different from the binder resin contained in the photosensitive layer. The intermediate layer may also contain additives. Examples of the additive contained in the intermediate layer are the same as those of other additives contained in the photosensitive layer.
(method for manufacturing photoreceptor)
Next, an example of a method for manufacturing the photoreceptor will be described. The method for manufacturing the photoreceptor includes a photosensitive layer forming step. In the photosensitive layer forming step, a coating liquid for forming a photosensitive layer (hereinafter, sometimes referred to as a coating liquid for a photosensitive layer) is prepared. The photosensitive layer is coated on the conductive substrate with the coating liquid. Then, at least a part of the solvent contained in the coating liquid for the photosensitive layer to be coated is removed, thereby forming a photosensitive layer. The coating liquid for photosensitive layer contains, for example, a charge generator, a hole transporting agent, an electron transporting agent, a binder resin, an additive and a solvent. A coating liquid for photosensitive layer is prepared by dissolving or dispersing a charge generator, a hole transporting agent, an electron transporting agent, a binder resin, and an additive in a solvent.
The solvent contained in the coating liquid for photosensitive layer is not particularly limited as long as it can dissolve or disperse each component contained in the coating liquid for photosensitive layer. Examples of solvents are: alcohols (more specifically, methanol, ethanol, isopropanol, butanol, and the like), aliphatic hydrocarbons (more specifically, n-hexane, octane, cyclohexane, and the like), aromatic hydrocarbons (more specifically, benzene, toluene, xylene, and the like), halogenated hydrocarbons (more specifically, dichloromethane, dichloroethane, carbon tetrachloride, chlorobenzene, and the like), ethers (more specifically, dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and the like), ketones (more specifically, acetone, methyl ethyl ketone, cyclohexanone, and the like), esters (more specifically, ethyl acetate, methyl acetate, and the like), dimethyl formaldehyde, dimethyl formamide, and dimethyl sulfoxide. These solvents may be used alone or in combination of two or more.
The photosensitive layer coating liquid is prepared by mixing and dispersing the respective components in a solvent. In the mixing or dispersing operation, for example, a bead mill, a roll mill, a ball mill, an attritor, a paint shaker, or an ultrasonic disperser can be used.
The method for coating with the coating liquid for photosensitive layer is not particularly limited as long as it can uniformly coat the coating liquid for photosensitive layer. The coating method is, for example: dip coating, spray coating, spin coating, and bar coating.
Examples of a method for removing at least a part of the solvent contained in the coating liquid for photosensitive layer include: heating, reducing the pressure, or a combination of heating and reducing the pressure. More specifically, a method of performing heat treatment (hot air drying) using a high-temperature dryer or a reduced-pressure dryer is given. The temperature of the heat treatment is, for example, 40 ℃ to 150 ℃. The time for the heat treatment is, for example, 3 minutes to 120 minutes.
The method for manufacturing the photoreceptor may further include a step of forming an intermediate layer, if necessary. The intermediate layer can be formed by a known method.
< image forming apparatus >
Next, an image forming apparatus including the photoreceptor 1 of the present embodiment will be described. Hereinafter, a tandem color image forming apparatus will be described as an example with reference to fig. 4. Fig. 4 is a cross-sectional view of an example of an image forming apparatus.
The image forming apparatus 110 in fig. 4 includes an image forming unit 40a, an image forming unit 40b, an image forming unit 40c, an image forming unit 40d, a transfer belt 50, and a fixing device 52. Hereinafter, the image forming units 40a, 40b, 40c, and 40d are all described as the image forming unit 40 unless otherwise noted.
The image forming unit 40 includes an image carrier 100, a charging device 42, an exposure device 44, a developing device 46, a transfer device 48, and a cleaning device 54. The image bearing member 100 is the photoreceptor 1 of the present embodiment.
As described above, the photoreceptor 1 of the present embodiment has excellent abrasion resistance and charging stability. Therefore, by providing the photoreceptor 1 as the image carrier 100, the image forming apparatus 110 has excellent durability and can form a good-quality image on the recording medium P.
An image carrier 100 is provided at a central position of the image forming unit 40. The image carrier 100 is provided to be rotatable in the arrow direction (counterclockwise direction). Around the image carrier 100, a charging device 42, an exposure device 44, a developing device 46, a transfer device 48, and a cleaning device 54 are provided in this order from the upstream side in the rotational direction of the image carrier 100.
Toner images of several colors (for example, four colors of black, cyan, magenta, and yellow) are sequentially superimposed on the recording medium P on the transfer belt 50 by each of the image forming units 40a to 40 d.
The charging device 42 charges the surface (for example, the circumferential surface) of the image carrier 100 to a positive polarity. The charging device 42 is, for example, a grid corotron charger.
The exposure device 44 irradiates (exposes) the surface of the charged image carrier 100 with light. That is, the exposure device 44 exposes the surface of the charged image carrier 100. Thereby, an electrostatic latent image is formed on the surface of the image carrier 100. Based on the image data input into the image forming apparatus 110, an electrostatic latent image is formed.
The developing device 46 supplies toner to the surface of the image carrier 100 to develop the electrostatic latent image into a toner image. The developing device 46 comes into contact with the surface of the image carrier 100. That is, the image forming apparatus 110 employs a contact development system. The developing device 46 is, for example, a developing roller. In the case where the developer is a one-component developer, the developing device 46 supplies toner as the one-component developer to the electrostatic latent image formed on the image carrier 100. In the case where the developer is a two-component developer, the developing device 46 supplies toner contained in the two-component developer and toner in the carrier to the electrostatic latent image formed on the image bearing member 100. Thereby, the image bearing member 100 bears the toner image.
The time (hereinafter, sometimes referred to as exposure-development time) from when the predetermined region on the surface of the image carrier 100 passes the exposure position PA until when the predetermined region moves to the development position PB is 100 milliseconds or less. The exposure position PA is a position at which light emitted from the exposure device 44 is incident on the surface of the image carrier 100. The developing position PB is a position at which the surface of the image carrier 100 abuts against the developing device 46 or the surface of the image carrier 100 is closest to the developing device 46. The defined area is for example a point on the surface of the image carrier 100.
The transfer belt 50 conveys the recording medium P between the image carrier 100 and the transfer device 48. The transfer belt 50 is an endless belt. The transfer belt 50 is provided to be rotatable in an arrow direction (clockwise direction).
The transfer device 48 transfers the toner image developed by the developing device 46 from the surface of the image carrier 100 to a recording medium P as a transfer target. Specifically, when the transfer device 48 transfers the toner image from the surface of the image carrier 100 to the recording medium P, the surface of the image carrier 100 comes into contact with the recording medium P. That is, the image forming apparatus 110 employs a direct transfer system. The transfer device 48 is, for example, a transfer roller.
The cleaning device 54 is used to collect toner adhering to the surface of the image carrier 100. The washing device 54 includes a housing 541 and a cleaning roller 542. In addition, the cleaning device 54 does not have a cleaning blade. The cleaning roller 542 is disposed inside the housing 541. The cleaning roller 542 is disposed in contact with the surface of the image carrier 100. The cleaning roller 542 grinds the surface of the image carrier 100, and collects the toner adhering to the surface of the image carrier 100 into the housing 541.
After the toner image is transferred onto the recording medium P by the transfer device 48, the recording medium P is conveyed to the fixing device 52 by the transfer belt 50. The fixing device 52 is, for example, a heating roller and/or a pressure roller. The unfixed toner image transferred by the transfer device 48 is heated and/or pressurized by the fixing device 52. The toner image is heated and/or pressurized, whereby the toner image is fixed on the recording medium P. As a result, an image is formed on the recording medium P.
As described above, although an example of the image forming apparatus is described, the image forming apparatus is not limited to the image forming apparatus 110 described above. The image forming apparatus 110 described above is a color image forming apparatus, but the image forming apparatus may be a monochrome image forming apparatus. In such a case, the image forming apparatus may include only 1 image forming unit, for example. Although the image forming apparatus 110 described above employs a tandem system, the image forming apparatus may employ a Rotary system (Rotary system), for example. The charging device 42 is described by taking a grid corotron charger as an example, but the charging device may be a charging device other than a grid corotron charger (for example, a charging roller, a charging brush, or a corotron charger). The image forming apparatus 110 described above employs a contact development system, but the image forming apparatus may employ a non-contact development system. The image forming apparatus 110 described above employs a direct transfer system, but the image forming apparatus may employ an intermediate transfer system. When the image forming apparatus employs the intermediate transfer system, the intermediate transfer belt corresponds to a transfer target. The cleaning device 54 described above includes the cleaning roller 542 and does not include the cleaning blade, but may be a cleaning device including the cleaning roller 542 and the cleaning blade. The image forming unit 40 described above does not include an electrostatic charge eliminating device, but the image forming unit may include an electrostatic charge eliminating device.
< processing box >
Next, an example of a process cartridge including the photoreceptor 1 according to the present embodiment will be described with reference to fig. 4. The process cartridge corresponds to each of the image forming units 40a to 40 d. The process cartridge includes an image carrier 100. The image bearing member 100 is the photoreceptor 1 of the present embodiment. As described above, the photoreceptor 1 of the present embodiment has excellent abrasion resistance and charging stability. Therefore, by providing the photoreceptor 1 as the image carrier 100, the process cartridge has excellent durability and can form a good-quality image on the recording medium P.
The process cartridge may further include at least one of the charging device 42, the exposure device 44, the developing device 46, the transfer device 48, and the cleaning device 54 (i.e., at least one device selected from the group consisting of the charging device 42, the exposure device 44, the developing device 46, the transfer device 48, and the cleaning device 54) in addition to the image carrier 100. The process cartridge may further include a static eliminator (not shown). The process cartridge is designed to be detachable with respect to the image forming apparatus 110. Therefore, the process cartridge is easy to handle, and when the sensitivity characteristics and the like of the image carrier 100 are deteriorated, the components included in the image carrier 100 can be easily and quickly replaced. As described above, the process cartridge including the photoreceptor 1 according to the present embodiment is described with reference to fig. 4.
[ examples ] A method for producing a compound
The present invention will be described in more detail with reference to examples. However, the present invention is not limited in any way to the scope of the examples.
< Material for Forming photosensitive layer >
First, as materials for forming a photosensitive layer of the photoreceptor, the following charge generating agent, electron transporting agent, hole transporting agent, binder resin, and additive are prepared.
(Charge generating agent)
The Y-type oxytitanium phthalocyanine described in the embodiment was prepared as a charge generating agent.
(Electron transport agent)
Each of the electron-transporting agents (ET1) to (ET-5) described in the embodiments was prepared as an electron-transporting agent.
(hole transport agent)
Hole-transporting agents (HT1) to (HT14) described in the embodiments were prepared as hole-transporting agents.
(Binder resin)
The polyarylate resins (R1) to (R12) described in the embodiment were prepared as binder resins. The viscosity average molecular weights of the polyarylate resins (R1) to (R12) were all 60000.
As the binder resin used in the comparative example, polycarbonate resins having repeating units represented by chemical formulae (R13), (R14), and (R15) (hereinafter, each of which is described as a polycarbonate resin (R13), (R14), and (R15)) were prepared. The viscosity average molecular weights of the polycarbonate resins (R13), (R14) and (R15) were all 60000. The polycarbonate resin (R13) corresponds to the bisphenol Z-type polycarbonate resin described in the patent documents of the background art.
Figure BDA0003369025180000581
(additives)
Ultraviolet absorbers (AD1) and (AD2) and antioxidants (AD3) and (AD4) described in the embodiment were prepared as additives.
As an additive used in the comparative example, an antioxidant represented by the following chemical formula (AD5) (hereinafter referred to as antioxidant (AD5)) was prepared.
Figure BDA0003369025180000591
< production of photoreceptor >
Photoreceptors (A-1) to (A-32) and (B-1) to (B-5) were produced using the charge generating agent, the electron transporting agent, the hole transporting agent, the binder resin and the additive described in < Material for Forming photosensitive layer > above.
(production of photoreceptor (A-1))
Using a ball mill, 3 parts by mass of Y-type oxytitanium phthalocyanine as a charge generator, 70 parts by mass of a hole transport agent (HT1), 40 parts by mass of an electron transport agent (ET1), 100 parts by mass of a polyarylate resin (R1) as a binder resin, 5 parts by mass of an ultraviolet absorber (AD1) as an additive, and 800 parts by mass of tetrahydrofuran as a solvent were mixed for 50 hours to obtain a coating liquid for a photosensitive layer. The coating liquid for photosensitive layer was applied on a conductive substrate (aluminum drum-shaped support) by dip coating. The coating liquid for the photosensitive layer applied was dried with hot air at 120 ℃ for 60 minutes. Thus, a photosensitive layer (film thickness: 28 μm) was formed on the conductive substrate, and the photoreceptor (A-1) was obtained. In the photoreceptor (A-1), a single photosensitive layer is directly formed on a conductive substrate.
(production of photoreceptors (A-2) to (A-32) and (B-2) to (B-5))
Photoreceptors (A-2) to (A-32) and (B-2) to (B-5) were produced according to the production method of photoreceptor (A-1) except that the hole-transporting agent, the electron-transporting agent, the additive and the binder resin of the types shown in tables 4 and 5 were used.
(production of photoreceptor (B-1))
Photoreceptor (B-1) was produced according to the method for producing photoreceptor (A-1) except that no additive was added.
< evaluation >
The following evaluations were carried out for each of the photoreceptors (A-1) to (A-32) and (B-1) to (B-5) to be evaluated.
< evaluation of abrasion resistance of photosensitive layer >
The coating liquid for photosensitive layer prepared in < production of photoreceptor > above was coated on a polypropylene sheet wound with an aluminum tube. The coating liquid for the photosensitive layer applied was dried at 120 ℃ for 60 minutes to produce a polypropylene sheet having a photosensitive layer (film thickness of 28 μm). Subsequently, the photosensitive layer was peeled off from the polypropylene sheet. The peeled photosensitive layer was adhered to a card-like member (manufactured by TABER corporation, "S-36"). Measuring mass M of card-like member having photosensitive layer adhered theretoA. Then, a card-like member was set on a rotary table of a rotary abrasion tester (manufactured by Toyo Seiki Seisaku-Sho Co., Ltd.). Subsequently, a grindstone (CS-10, manufactured by TABER) loaded at 500gf was placed on the photosensitive layer on the card-like member, and the rotary table was rotated at 60rpm for 500 revolutions. This causes abrasion of the photosensitive layer on the turntable. After the abrasion, the mass M of the card-like member to which the photosensitive layer is attached is measured againBThe amount of wear (M) of the change in the mass of the photosensitive layer before and after the wear is determinedA-MB). The abrasion resistance of the photoreceptor was evaluated from the abrasion amount based on the following criteria. The results of the abrasion resistance evaluation are shown in tables 4 and 5. The photoreceptor evaluated as having abrasion resistance was evaluated as having poor abrasion resistance.
(evaluation criteria for abrasion resistance)
Evaluation A: the abrasion loss is less than 5 mg.
Evaluation B: the abrasion loss is 5mg or more and less than 8 mg.
Evaluation C: the abrasion loss was 8mg or more.
< evaluation of Charge stability of photoreceptor >
The evaluation environment of the charging stability of the photoreceptor was an environment at a temperature of 10 ℃ and a relative humidity of 15% RH. For the evaluation of the charging stability, an evaluation machine (a changer of "FS-C5250 DN" manufactured by Kyowa office information systems Co., Ltd.) was used. The evaluation machine was equipped with a grid corotron charger and a cleaning roller, and was not equipped with a cleaning blade. The opposite polarity of the grid corotron charger is positive. The rotation speed of the photoreceptor was set so that the exposure-development time reached 70 msec.
First, an image a (full-area blank image) was printed on 3 sheets of a recording medium (a4 paper) using an evaluation machine. When each sheet is printed, the surface potential of the photoreceptor is measured at the development position. In addition, when printing a blank image, since exposure is not performed, the measured surface potential corresponds to a charged potential. The surface potential was measured 1 time for printing 1 sheet, 3 times in total. The average value of the measured surface potentials for 3 times was used as the charging potential V before the printing test01(unit: + V).
Then, a printing test was performed. In the printing test, the printing of an image B (print pattern image with a print coverage of 5%) was performed on 10,000 recording media (a4 paper) using an evaluation machine every 15 seconds. Immediately after the end of the print test, printing of an image a (full-face blank image) was performed on 3 recording media (a4 paper sheets). When printing is performed on each sheet, the surface potential of the photoreceptor is measured at the development position. The surface potential was measured 1 time for printing 1 sheet, 3 times in total. The average value of the measured surface potentials for 3 times is used as the charged potential V after the printing test02(unit: + V).
Charged potential V before printing test01Subtracting the charged potential V after the printing test02Value of (V)01-V02) As a decrease amount of charged potential Δ V0(unit: V). According to the charge potential drop amount DeltaV0The evaluation of the charging stability of the photoreceptor was performed based on the following criteria. The evaluation results of the charging stability are shown in tables 4 and 5. The photoreceptor evaluated as C in the charging stability, i.e., the photoreceptor evaluated as poor in the charging stability.
(evaluation criteria for Charge stability)
Evaluation A: charge potential drop amount Δ V0Is 0V or more and less than 60V.
Evaluation B: charge potential drop amount Δ V0Is 60V or more and less than 110V.
Evaluation C: charge potential drop amount Δ V0Is 110V or more.
In tables 4 and 5, the meanings of the technical terms are as follows. "HTM" means a hole transporting agent. "ETM" means an electron transport agent. "resin" means a bonding resin.
[ TABLE 4 ]
Photosensitive body HTM ETM Additive agent Resin composition Abrasion resistance Stability of electrification
Example 1 A-1 HT1 ET1 AD1 R1 A A
Example 2 A-2 HT1 ET1 AD2 R1 A A
Example 3 A-3 HT1 ET1 AD3 R1 A A
Example 4 A-4 HT1 ET1 AD4 R1 B A
Example 5 A-5 HT2 ET1 AD1 R1 A A
Example 6 A-6 HT3 ET1 AD1 R1 A A
Example 7 A-7 HT4 ET1 AD1 R1 A A
Example 8 A-8 HT5 ET1 AD1 R1 A A
Example 9 A-9 HT6 ET1 AD1 R1 A A
Example 10 A-10 HT7 ET1 AD1 R1 A A
Example 11 A-11 HT8 ET1 AD1 R1 A A
Example 12 A-12 HT9 ET1 AD1 R1 A A
Example 13 A-13 HT10 ET1 AD1 R1 A A
Example 14 A-14 HT11 ET1 AD1 R1 A A
Example 15 A-15 HT12 ET1 AD1 R1 A A
Example 16 A-16 HT13 ET1 AD1 R1 A A
Example 17 A-17 HT14 ET1 AD1 R1 A A
Example 18 A-18 HT1 ET2 AD1 R1 A A
Example 19 A-19 HT1 ET3 AD1 R1 A A
Example 20 A-20 HT1 ET4 AD1 R1 A A
Example 21 A-21 HT1 ET5 AD1 R1 A A
Example 22 A-22 HT1 ET1 AD1 R2 A A
Example 23 A-23 HT1 ET1 AD1 R3 A A
Example 24 A-24 HT1 ET1 AD1 R4 A A
Example 25 A-25 HT1 ET1 AD1 R5 A A
Example 26 A-26 HT1 ET1 AD1 R6 A A
Example 27 A-27 HT1 ET1 AD1 R7 A A
Example 28 A-28 HT1 ET1 AD1 R8 A A
Example 29 A-29 HT1 ET1 AD1 R9 A A
Example 30 A-30 HT1 ET1 AD1 R10 A A
Example 31 A-31 HT1 ET1 AD1 R11 A A
Example 32 A-32 HT1 ET1 AD1 R12 A A
[ TABLE 5 ]
Photosensitive body HTM ETM Additive agent Resin composition Abrasion resistance Stability of electrification
Comparative example 1 B-1 HT1 ET1 Is free of R1 A C
Comparative example 2 B-2 HT1 ET1 AD1 R13 C C
Comparative example 3 B-3 HT1 ET1 AD1 R14 C C
Comparative example 4 B-4 HT1 ET1 AD1 R15 C C
Comparative example 5 B-5 HT1 ET1 AD5 R1 B C
As shown in table 4, the photosensitive layers of the photoreceptors (a-1) to (a-32) each contain 1 of polyarylate resins (R1) to (R12) as a binder resin. The polyarylate resins (R1) to (R12) are each a polyarylate resin of polyarylate resins (PA) containing at least 1 repeating unit (1) and at least 1 repeating unit (2). The additives contained in the photosensitive layers of the photoreceptors (a-1) to (a-32) are 1 of the specific additives (more specifically, 1 of the ultraviolet absorber (AD1), the ultraviolet absorber (AD2), the antioxidant (AD3), and the antioxidant (AD 4)). The abrasion resistance of the photoreceptors (A-1) to (A-32) was evaluated as evaluation A or B, and these photoreceptors were excellent in abrasion resistance. Evaluation of the charging stability of the photoreceptors (A-1) to (A-32) was evaluation A, and the charging stability of these photoreceptors was good.
As described above, the photoreceptor according to the present invention exhibits excellent abrasion resistance and charging stability. The photoreceptor according to the present invention has excellent abrasion resistance and charging stability, and therefore, the process cartridge and the image forming apparatus having the photoreceptor according to the present invention have excellent durability and can form a high-quality image.
[ industrial availability ]
The photoreceptor and the process cartridge according to the present invention can be used in an image forming apparatus. The image forming apparatus according to the present invention can be used to form an image on a recording medium.

Claims (13)

1. An electrophotographic photoreceptor is provided with a photosensitive layer containing a photosensitive compound,
comprises a conductive substrate and a photosensitive layer,
the photosensitive layer is a single layer of a photosensitive material,
the photosensitive layer contains a charge generator, a hole transporting agent, an electron transporting agent, a binder resin and an additive,
the binder resin contains a polyarylate resin having at least 1 repeating unit represented by the general formula (1) and at least 1 repeating unit represented by the general formula (2),
the additive contains at least 1 compound among the compounds represented by the general formulae (50), (51) and (52),
Figure FDA0003369025170000011
in the general formula (1), R1And R2Both represent a methyl group, W is a divalent group represented by the general formula (W2),
in the general formula (2), X is a divalent group represented by the formula (X1), (X2), (X3), (X4) or (X6),
Figure FDA0003369025170000012
in the general formula (W2), a represents 1 or 2,
Figure FDA0003369025170000021
in the general formula (50) described above,
R51represents a halogen atom or a C1-C6 alkyl group substituted with a halogen atom,
R52represents a C1-C10 alkyl group, a C7-C20 aralkyl group or a C6-C22 aryl group,
n and m are each independently an integer of 0 to 4 inclusive,
when n represents an integer of 2 to 4, a plurality of R51Are the same as or different from each other,
when m represents an integer of 2 to 4, a plurality of R52Are the same as or different from each other,
Figure FDA0003369025170000022
in the general formula (51) described above,
R53represents a C3-C10 alkyl group,
p represents an integer of 1 to 4 inclusive,
q and r are each independently an integer of 1 to 3,
s represents an integer of 1 to 4 inclusive,
when p is an integer of 2 to 4, a plurality of R53Are the same as or different from each other,
when s represents an integer of 2 or more and 4 or less, a plurality of p's are the same or different from each other, a plurality of q's are the same or different from each other, a plurality of r's are the same or different from each other,
Figure FDA0003369025170000031
in the general formula (52) described above,
R55represents a C3-C10 alkyl group,
R56represents a C10-C30 alkyl group,
u represents an integer of 1 to 3 inclusive,
t represents an integer of 1 to 4 inclusive,
when t represents an integer of 2 to 4, a plurality of R55The same as or different from each other.
2. The electrophotographic photoreceptor according to claim 1,
in the general formula (50) described above,
R51represents a halogen atom, and is a halogen atom,
R52represents a C1-C10 alkyl group,
n represents a number of 0 or 1,
m represents a number of 1 or 2,
in the case where m represents 2, 2R52Are the same as or different from each other,
in the general formula (51) described above,
R53represents a C3-C10 alkyl group,
p represents a group of 2 and p represents a group of,
q represents a number of 2, and q represents,
r represents a number of 1 s, and r represents a number of 1 s,
s represents a number of 4, and s represents,
8R53Are the same as or different from each other,
in the general formula (52) described above,
R55represents a C3-C10 alkyl group,
R56Represents a C10-C30 alkyl group,
u represents a number of atoms represented by 2,
t represents a number of 2, t represents,
2R55The same as or different from each other.
3. The electrophotographic photoreceptor according to claim 1,
at least 1 compound among the compounds represented by the general formulae (50), (51) and (52) is at least 1 compound among the compounds represented by the chemical formulae (AD1), (AD2), (AD3) and (AD4),
Figure FDA0003369025170000041
Figure FDA0003369025170000051
4. the electrophotographic photoreceptor according to claim 1,
the polyarylate resin is a polyarylate resin having repeating units represented by chemical formulas (1-2) and (2-X3),
Figure FDA0003369025170000052
or a polyarylate resin comprising the repeating units represented by the above chemical formula (1-2) and chemical formula (2-X6),
Figure FDA0003369025170000053
5. the electrophotographic photoreceptor according to claim 1,
the polyarylate resin is a polyarylate resin having a repeating unit represented by chemical formula (1-2), chemical formula (2-X1), and chemical formula (2-X4),
Figure FDA0003369025170000061
or a polyarylate resin comprising repeating units represented by the above chemical formula (1-2), the above chemical formula (2-X1), and the above chemical formula (2-X3),
Figure FDA0003369025170000062
or a polyarylate resin comprising repeating units represented by the following chemical formula (1-2), the following chemical formula (2-X4), and the following chemical formula (2-X3),
Figure FDA0003369025170000063
or a polyarylate resin comprising repeating units represented by the above chemical formula (1-2), the above chemical formula (2-X6), and the above chemical formula (2-X3),
Figure FDA0003369025170000064
or a polyarylate resin comprising repeating units represented by the following chemical formula (1-2), the following chemical formula (2-X6), and the following chemical formula (2-X1),
Figure FDA0003369025170000071
or a polyarylate resin comprising repeating units represented by the following chemical formula (1-1), the following chemical formula (2-X1), and the following chemical formula (2-X3),
Figure FDA0003369025170000072
6. the electrophotographic photoreceptor according to claim 1,
the polyarylate resin is a polyarylate resin having a repeating unit represented by chemical formula (1-1), chemical formula (1-2), chemical formula (2-X1), and chemical formula (2-X3),
Figure FDA0003369025170000081
7. the electrophotographic photoreceptor according to claim 1,
the electron transport agent contains a compound represented by general formula (10), (11), (12), (13) or (14),
Figure FDA0003369025170000082
in the general formula (10), Q1、Q2、Q3And Q4Independently of one another, represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C6-C14 aryl group or a C7-C20 aralkyl group,
in the general formula (11), Q5Represents a C1-C6 alkyl group or a C6-C14 aryl group, Q6Represents C1-C6 alkyl, C6-C14 aryl, C1-C6 alkoxy, C7-C20 aralkyl, C6-C14 aryloxy or C7-C20 aralkyloxy, Q7Represents a C1-C6 alkyl group, v represents an integer of 0 to 4 inclusive,
in the general formula (12), Q8And Q9Independently of one another, represents a C6-C14 aryl group having at least one C1-C6 alkyl substituent or an unsubstituted C6-C14 aryl group,
in the general formula (13), Q10、Q11、Q12And Q13Each independently represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a C6-C14 aryl group, a C7-C20 aralkyl group or a C3-C14 heterocyclic group,
in the general formula (14), Q14、Q15And Q16Independently of one another, a C1-C6 alkyl group, a C6-C14 aryl group substituted with a halogen atom, or an unsubstituted C6-C14 aryl group.
8. The electrophotographic photoreceptor according to claim 1,
the electron transport agent contains a compound represented by the formula (ET1), (ET2), (ET3), (ET4) or (ET5),
Figure FDA0003369025170000101
9. the electrophotographic photoreceptor according to claim 1,
the hole-transporting agent contains a compound represented by the general formula (20), (21), (22), (23), (24), (25), (26) or (27),
Figure FDA0003369025170000111
Figure FDA0003369025170000121
in the general formula (20), R11、R12、R13、R14、R15And R16Each independently of the other represents C1-C8 alkyl orPhenyl radical, R17And R18Each independently represents a hydrogen atom, a C1-C8 alkyl group or a phenyl group, b1, b2, b3 and b4 each independently represents an integer of 0 to 5, b5 and b6 each independently represents an integer of 0 to 4, d and e each independently represents 0 or 1,
in the general formula (21), R20Represents a hydrogen atom, a C1-C8 alkyl group, a C1-C8 alkoxy group, a phenyl group having a C1-C8 alkyl substituent or an unsubstituted phenyl group, R21、R22And R23Independently represents a C1-C8 alkyl group or a C1-C8 alkoxy group, f1, f2 and f3 independently represent an integer of 0 to 5, f4 represents 0 or 1,
in the general formula (22), R31、R32、R33、R34And R35Independently represents a C1-C8 alkyl group or a C1-C8 alkoxy group, g1, g2, g3, g4 and g5 independently represent an integer of 0 to 5,
in the general formula (23), R41、R42、R43、R44、R45And R46Independently represents C1-C8 alkyl, phenyl or C1-C8 alkoxy, h1, h2, h4 and h5 independently represent an integer of 0 to 5, h3 and h6 independently represent an integer of 0 to 4,
in the general formula (24), R61、R62And R63Each independently represents a C1-C8 alkyl group, R64、R65And R66Each independently represents a hydrogen atom or a C1-C8 alkyl group,
in the general formula (25), R71、R72、R73And R74Independently represents a C1-C8 alkyl group, j1, j2, j3 and j4 independently represent an integer of 0 to 5, j5 represents 0 or 1,
in the general formula (26), R81、R82And R83Each independently represents C1-C8 alkyl, phenyl or C1-C8 alkoxy, R84And R85Each independently represents a phenyl group having a C1-C8 alkyl substituent, an unsubstituted phenyl group, a hydrogen atom, a C1-C8 alkyl group or a C1-C8 alkoxy group, and each of k1, k2 and k3 independently representsAn integer of 0 to 5, k4 and k5 each independently represents 1 or 2,
in the general formula (27), R91、R92And R93Each independently represents a C1-C8 alkyl group, R94Represents a C1-C8 alkyl group or a hydrogen atom, and v1, v2 and v3 each independently represent an integer of 0 to 5.
10. The electrophotographic photoreceptor according to claim 1,
the hole transporting agent contains a compound represented by the formula (HT1), (HT2), (HT3), (HT4), (HT5), (HT6), (HT7), (HT8), (HT9), (HT10), (HT11), (HT12), (HT13), or (HT14),
Figure FDA0003369025170000141
Figure FDA0003369025170000151
Figure FDA0003369025170000161
11. a kind of processing box is disclosed, which comprises a box body,
the electrophotographic photoreceptor according to claim 1.
12. An image forming apparatus includes:
an image carrier provided rotatably;
a charging device for charging the surface of the image carrier to a positive polarity;
an exposure device configured to irradiate the surface of the charged image carrier with light to form an electrostatic latent image on the surface of the image carrier;
a developing device that develops the electrostatic latent image into a toner image; and
a transfer device for transferring the toner image from the image bearing member to a transfer object,
the image bearing member is the electrophotographic photoreceptor according to claim 1.
13. The image forming apparatus according to claim 12,
the time from when the prescribed region on the surface of the image carrier passes the exposure position to when the prescribed region moves to the development position is 100 milliseconds or less,
the exposure position is a position at which the light irradiated from the exposure device is incident on the surface of the image carrier,
the developing position is a position at which the surface of the image carrier abuts against the developing device or the surface of the image carrier is closest to the developing device.
CN202080038159.6A 2019-05-28 2020-05-27 Electrophotographic photoreceptor, process cartridge, and image forming apparatus Pending CN113874791A (en)

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