JP3333975B2 - Electrophotographic photoreceptor - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an electrophotographic photoreceptor using the electrophotographic photoreceptor binder resins, has good electrical properties and good compatibility with the carrier transport material, and mechanical The present invention relates to an electrophotographic photosensitive member having excellent durability.

[0002]

2. Description of the Related Art Conventionally, electrophotographic photosensitive members having photosensitivity to visible light have been widely used in copiers, printers and the like.
Such electrophotographic photoreceptors include selenium, zinc oxide,
Inorganic photoreceptors provided with a photosensitive layer mainly containing an inorganic photoconductive substance such as cadmium sulfide are widely used. However, such an inorganic photoreceptor is not always satisfactory in characteristics such as photosensitivity, heat stability, moisture resistance, and durability required for an electrophotographic photoreceptor such as a copying machine. For example, selenium crystallizes due to heat, fingerprint stains when touched with a hand, and the like, so that the above characteristics as an electrophotographic photoreceptor are likely to deteriorate. An electrophotographic photoreceptor using cadmium sulfide is inferior in humidity resistance and durability, and an electrophotographic photoreceptor using zinc oxide has disadvantages in that there are great restrictions on production and handling.

[0003] In order to improve such inorganic photoconductive materials, various organic photoconductive materials have been attempted to be used for a photosensitive layer of an electrophotographic photosensitive member, and research and development have been actively conducted in recent years. For example, Japanese Patent Publication No. 50-10496 discloses poly-N-
An organophotoreceptor having a photosensitive layer containing vinylcarbazole and 2,4,7-trinitro-9-fluorenone is described. However, this photoreceptor is also insufficient in sensitivity and durability. Therefore, a function-separated electrophotographic photoreceptor has been developed in which the photosensitive layer is divided into two layers, the carrier generating layer and the carrier transporting layer are separately formed, and the carrier generating substance and the carrier transporting substance are respectively contained therein. Since the carrier generation function and the carrier transport function can be individually assigned to different substances, a substance exhibiting each function can be selected from a wide range. Therefore, it is expected that an electrophotographic photosensitive member having arbitrary characteristics can be obtained relatively easily.

The photosensitive layer of such a function-separated type electrophotographic photosensitive member is usually formed by dispersing a carrier generating substance or a carrier transporting substance in a binder resin. Conventionally, polyester resins, polyarylate resins, polystyrene resins, polymethyl methacrylate resins, polycarbonate resins, etc. have been used as the binder resin in terms of sensitivity, mechanical strength, etc., but the solubility of these resins in organic solvents is low. Therefore, a resin having high solubility has been desired in the production process of the photoreceptor. In addition, when the above resin is used, it has been necessary to use a halogen-based solvent which is strongly pointed out to the harmfulness to the environment, but in recent years, from the viewpoint of global environmental protection, it is possible to manufacture without using a harmful halogen-based solvent. The development of a photoconductor that is friendly to the global environment is desired.

Further, the conventional photosensitive layer using a resin has insufficient mechanical strength such as abrasion and scratches caused by contact with a cleaning blade, adhered toner or transfer paper.

In order to solve this problem, a method of dispersing a carrier-generating substance in a curable resin such as a polyurethane resin (JP-A-51-23738) and a method of using a curable resin in a carrier transport layer have been proposed so far. (JP-A-56-51747), a method of providing a protective layer on a photosensitive layer (JP-A-56-48637), and the like have been proposed. However, in these methods, the compatibility between the carrier transporting material and the binder is poor, so that a problem such as the precipitation of the carrier transporting material occurs, which has a problem of adversely affecting the electrical characteristics such as sensitivity and residual potential.

[0007]

An object of the present invention is to provide a sensitivity with Luba inductor <br/> chromatography resins can produce an electrophotographic photosensitive member having good electrical properties, charging properties, excellent equipotential stability Another object of the present invention is to provide an electrophotographic photoreceptor having excellent electrical characteristics, excellent compatibility with a carrier transporting substance, and excellent mechanical durability.

Another object of the present invention is to provide a binder resin capable of producing an electrophotographic photosensitive member without using an environmentally harmful halogen-based solvent.

As a substitute for the halogen-based solvent, generally, ketone-based, ester-based, alcohol-based solvents and the like can be considered. However, polyester resins, polyacrylate resins, polystyrene resins, polymethyl methacrylate resins, polycarbonate resins, and the like, which are widely used at present, have a problem in solubility, so that their use is limited. On the other hand, resins soluble in these solvents include polyamide resins, formal resins, butyral resins, and phenoxy resins. However, these resins have poor compatibility with the carrier transporting material in a system where the carrier transporting material coexists, so that the photosensitive layer becomes opaque, and as a result, fog is generated due to uneven light transmission of the opaque portion. Furthermore, these resins have problems in electrical characteristics. That is, an object of the present invention is to overcome these problems and to provide a binder resin having excellent compatibility with a carrier transporting substance and excellent electrical properties.

[0010]

According to the present invention, there is provided a surface layer containing a binder resin having a repeating unit represented by the following general formula (1 ) and a carrier transporting material, and 10% to 90% of the repeating unit. An electrophotographic photoreceptor in which the OH group present in the repeating unit is substituted with another functional group X so that the following is the repeating unit represented by the general formula (1 ' ), and the binder resin is cured. The present invention relates to an electrophotographic photoreceptor.

[0011]

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(Wherein, R1 and R2 represent a hydrogen atom or a substituted or unsubstituted alkyl group, aryl group, or phenyl group, and R1 and R2 may combine to form a ring. a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group .X is a hydrogen atom, c androgenic atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group or a heterocyclic oxy group,.)

[0013]

[0014]

[0015]

[0016]

The binder resin of the present invention can be obtained by substituting an OH group in a resin having a repeating unit of the general formula (1 ) with another functional group. Examples include a methylation reaction with dimethyl sulfate, a reaction with an olefin under acidic conditions, a halogenation reaction, an acylation reaction, a reaction with hydropyrans, and the like, but the method for producing the resin of the present invention is limited to these methods. It is not something to be done.

The resin having a repeating unit represented by the general formula (1) can be obtained from a bisphenol compound and epichlorohydrin. Various substituents for R1 and R2 in the formula can be considered depending on the bisphenol compound used, but alkyl groups such as methyl group, ethyl group, propyl group and cyclohexyl, phenyl group, benzyl group, trifluoromethyl group and the like are desirable.

The binder resin of the present invention is Ru used indicates Ruki Yaria transporting material and good compatibility to form an electrophotographic photoreceptor calibration <br/> rear transport layer.

Further, the resin of the present invention can obtain high mechanical strength by being cured with various curing agents, and is excellent in compatibility with a carrier transporting substance, electrical properties and durability.

As a method for curing the resin used in the present invention, any method of heat curing and light curing is possible.
Generally, it is cured using a curing agent. Examples of the type of the curing agent include a polyisocyanate compound, an isocyanate compound such as a blocked isocyanate by a partial reaction with a compound having a group capable of reacting with an isocyanate group, a urea resin, a melamine resin, a phenol resin, and an epoxy resin. Is not limited to these.

Specific examples of the isocyanate compound are shown below.

[0023]

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[0024]

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[0025]

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[0026]

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[0027]

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[0028]

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The ratio of the curing agent to the resin of the present invention is determined by the number of remaining OH groups. In general, since one reaction point of the curing agent corresponds to one residual OH group, it is preferably 10% to 200% with respect to the resin. If the amount of the curing agent is too small, sufficient mechanical strength cannot be obtained, and if an excessive amount of the curing agent is present, the electrical properties are deteriorated.

Further layer formed by curing the resin of the present invention is used as the outermost layer because of its good good mechanical strength. The photosensitive layer because they exhibit good compatibility with the carrier transport material, especially in the case of a function-separated photoreceptor Ru used for the carrier transporting layers disposed as the outermost layer.

As the carrier generating material used in the electrophotographic photoreceptor of the present invention, a phthalocyanine compound, specifically, a crystalline form of titanyl phthalocyanine such as A type, B type or Y type, or a mixture of titanyl phthalocyanine and another phthalocyanine is used. And various metal phthalocyanines and naphthalocyanines represented by crystal-free, X-type and τ-type metal-free phthalocyanines, copper phthalocyanines and the like. Other porphyrin derivatives, azo compounds, imidazole perylene, perylene dyes such as bisimido perylene, polycyclic quinone dyes such as anthanthrone, anthraquinone, perinone dyes, eutectic complexes of pyrylium compounds and pyrylium compounds, azurenium compounds, squarium compounds, etc. No.

Next, various carriers can be used as the carrier transporting material used in the electrophotographic photoreceptor of the present invention. Representative examples thereof include oxazole, oxadiazole, thiazole, thiadiazole, imidazole and the like. Compounds having a nitrogen-containing heterocyclic nucleus and a condensed ring nucleus thereof, polyarylalkane compounds, pyrazoline compounds, hydrazone compounds, triarylamine compounds, styryl compounds, poly (bis) styryl compounds, styryl Triphenylamine compound, β
-Phenylstyryltriphenylamine compounds, butadiene compounds, hexatriene compounds, carbazole compounds, condensed polycyclic compounds, and the like. Specific examples of the carrier transporting material include, for example, JP-A-61-10735
Examples of the carrier transport material described in 6 include:
Particularly typical structures are shown below.

[0033]

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[0034]

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[0035]

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[0036]

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[0037]

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[0038]

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Various configurations of the photosensitive member are known. The photoreceptor of the present invention can be either a dispersion type or a stacked type function-separated type photoreceptor. Normally, the configuration is as shown in (1) , (3), (5), and (6) of FIG. (1) a layer structure shown in the carrier generation layer 2 is formed on the conductive substrate 1, this is intended a carrier transport layer 3 was formed to the photosensitive layer 4 laminated, (3) (1 between the photosensitive layer 4 and conductive support 1 of a layer structure of a) are those in which an intermediate layer 5, Ru der that prevents the injection of free electrons in the conductive support 1. (5) shows the formation of the photosensitive layer 4 ″ containing the carrier generating substance 6 and the carrier transporting substance 7 combined therewith, and (6) shows the formation of the photosensitive layer 4 ″ between the photosensitive layer 4 ″ and the conductive support 1. This is provided with the intermediate layer 5 described above.

[0040]

In forming the photosensitive layer, it is effective to apply a solution in which a carrier-generating substance or a carrier-transporting substance is dissolved alone or together with a binder or an additive. However, since the solubility of the carrier-generating substance is generally low, in such a case, the carrier-generating substance is transferred to an ultrasonic disperser,
A method of applying a liquid in which fine particles are dispersed in an appropriate dispersion medium using a dispersing device such as a ball mill, a sand mill, and a homomixer is effective. In this case, the binder and the additive are usually used by adding to the dispersion.

As the dehalogenating solvent or dispersion medium used for forming the photosensitive layer, any of a wide variety of solvents can be used. For example, n-butylamine, ethylenediamine, N, N-
Dimethylformamide, acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 4-methoxy-4-methyl-2-pentanone, tetrahydrofuran, dioxane, ethyl acetate,
Examples include n-butyl acetate, t-butyl acetate, methyl cellosolve, ethyl cellosolve, butyl cellosolve, ethylene glycol dimethyl ether, toluene, xylene, acetophenone, methanol, ethanol, propanol, butanol and the like.

In forming the carrier generation layer or the carrier transport layer, other binders may be used in combination as far as they are soluble in the dehalogenating solvent. Any binder can be selected as the combined binder, but a high molecular polymer having film forming ability is desirable. Examples of such a polymer include, but are not limited to, the following.

Polycarbonate Polycarbonate Z resin Acrylic resin Methacrylic resin Polyvinyl chloride Polyvinylidene chloride Polystyrene Styrene-butadiene copolymer Polyvinyl acetate Polyvinyl formal Polyvinyl butyral Polyvinyl acetal Polyvinyl carbazole Styrene-alkyd resin Silicon resin Silicon-alkyd resin Silicon-butyral resin Polyester Polyurethane Polyamide Epoxy resin Phenolic resin Vinylidene chloride-acrylonitrile copolymer Vinyl chloride-vinyl acetate copolymer Vinyl chloride-vinyl acetate-maleic anhydride copolymer Ratio of carrier-generating substance to binder is 10 to 600
% By weight, more preferably 50 to 400% by weight. The ratio of the carrier transport material to the binder is desirably 10 to 500% by weight. The ratio of the infrared absorbing dye to the binder is 0.0001 to 10% by weight, particularly preferably 0.001% to 1% by weight. The thickness of the carrier generation layer is 0.01 to 20 μm,
5-5 μm is preferred. The thickness of the carrier transport layer is 1 to 100
μm, and more preferably 5 to 30 μm.

The photosensitive layer may contain an electron-accepting substance for the purpose of improving the sensitivity, reducing the residual potential, or reducing fatigue upon repeated use. Examples of such electron accepting substances include succinic anhydride, maleic anhydride, dibromosuccinic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 3-nitrophthalic anhydride, and 4-nitroanhydride. Phthalic acid, pyromellitic anhydride, melitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, o-dinitrobenzene, m-dinitrobenzene, 1,3,5-trinitrobenzene, p-nitrobenzonitrile, picryl chloride , Quinone chlorimide,
Chloranil, bromanil, dichlorodicyano-p-benzoquinone, anthraquinone, dinitroanthraquinone, 9-
Fluorenylidene malononitrile, polynitro-9-fluorenylidene malononitrile, picric acid, o-nitrobenzoic acid, p-nitrobenzoic acid, 3,5-dinitrobenzoic acid, pentafluorobenzoic acid, 5-nitrosalicylic acid, 3 , 5-dinitrosalicylic acid, phthalic acid, melitic acid, and other compounds having a high electron affinity. The addition ratio of the electron-accepting substance is preferably 0.01 to 200, more preferably 0.1 to 100, based on 100 of the weight of the carrier generating substance.

Further, the above photosensitive layer contains storability, durability,
For the purpose of improving environmental resistance, a deterioration inhibitor such as an antioxidant or a light stabilizer can be contained. Compounds used for such purposes include, for example, chromanol derivatives such as tocopherol and etherified or esterified compounds thereof, polyarylalkane compounds,
Hydroquinone derivatives and their mono- and dietherified compounds, benzophenone derivatives, benzotriazole derivatives, thioether compounds, phosphonate esters, phosphite esters, phenylenediamine derivatives, phenol compounds, hindered phenol compounds, linear amine compounds, cyclic amine compounds, Hindered amine compounds are effective. Specific examples of particularly effective compounds include “IR
GANOX1010 ”,“ IRGANOX 565 ”
(Manufactured by Ciba Geigy), "Sumilyzer BHT"
Hindered phenol compounds such as "Sumilyzer MDP" (manufactured by Sumitomo Chemical Co., Ltd.) "Sanol LS-262"
6 "and" Sanol LS-622LD "(manufactured by Sankyo Co., Ltd.).

As the binder used for the intermediate layer, the protective layer and the like, those mentioned above for the carrier generating layer and the carrier transporting layer can be used. In addition, nylon resin, ethylene-vinyl acetate copolymer, Ethylene resins such as ethylene-vinyl acetate-maleic anhydride copolymer and ethylene-vinyl acetate-methacrylic acid copolymer, polyvinyl alcohol, and cellulose derivatives are effective. In addition, a curable binder utilizing thermal curing or chemical curing of melamine, epoxy, isocyanate, or the like can be used.

As the conductive support, a metal plate or a metal drum may be used, or a conductive polymer such as a conductive polymer or indium oxide, or a thin layer of a metal such as aluminum or palladium may be applied, vapor-deposited or laminated. Thus, a material provided on a substrate such as paper or a plastic film can be used.

The binder resin of the present invention and the electrophotographic photoreceptor using the same can be obtained as described above. The characteristic feature of the resin of the present invention is that the resin of the present invention has good solubility in solvents other than halogen solvents. In addition, it has excellent compatibility with a carrier transporting substance and can be used as a dehalogenated solvent in the production of a photosensitive layer in which the use of a halogen-based solvent has been conventionally required. Further, the photosensitive layer containing the binder resin has a characteristic that it is also excellent in electrical characteristics such as sensitivity, charging ability and potential stability.

[0050]

Embodiments of the present invention will be described below.

(Synthesis Example 1) 3 parts of 2,3-dihydropyran were dissolved in a solution of 10 parts of a phenoxy resin having a repeating unit represented by the general formula (1) (PKHH: manufactured by UCC) in 100 parts of tetrahydrofuran. 0.1 parts of concentrated hydrochloric acid was added and reacted for 3 hours. After the reaction, the reaction product was precipitated in a large amount of methanol, washed with methanol, and dried to obtain about 10 parts of a resin. Analysis of the obtained resin revealed that about 50% of the OH groups of the resin before the reaction remained.

(Synthesis Example 2) A resin was obtained in the same manner as in Synthesis Example 1 except that 30 parts of 2,3-dihydropyran and 0.5 part of concentrated hydrochloric acid were used. About 20% of OH groups remained in this resin.

(Synthesis Example 3) A resin was obtained in the same manner as in Synthesis Example 1 except that 1.5 parts of 2,3-dihydropyran was used. About 80% of the OH groups remained in this resin.

(Synthesis Example 4) Approximately 50% of residual O was obtained in the same manner as in Synthesis Example 1 except that poly (2-hydroxyethyl methacrylate) was used in place of the phenoxy resin.
A methacrylic resin having an H group was obtained.

(Synthesis Example 5) 19 parts of dimethyl sulfuric acid was added dropwise to a solution of 12 parts of poly (4-hydroxystyrene) and 8 parts of sodium hydroxide dissolved in 400 parts of water.
Allowed to react for hours. After the reaction, the precipitated resin was washed with water and methanol, and dried to obtain 11 parts of a resin. The residual OH groups of the obtained resin were 20% or less.

(Example 1) Bragg angle 2θ of 9.5 °, 24.
To 1 part by weight of Y-type titanyl phthalocyanine having peaks at 1 ° and 27.2 °, 100 parts by weight of methyl ethyl ketone and 1 part by weight of a polyvinyl butyral resin were added and dispersed using a ball mill.

On the other hand, a subbing layer made of polyamide resin "CM8000" (manufactured by Toray Industries, Inc.) having a thickness of 0.3 μm was provided on a polyester base on which aluminum was vapor-deposited by a wire bar coating method. A carrier generation layer having a thickness of 0.2 μm was formed by coating with a bar. Then, 1 part by weight of the carrier transporting substance (21) and 1.33 of the resin obtained in Synthesis Example 1 were added.
Parts by weight and a small amount of silicone oil “KF-54” (manufactured by Shin-Etsu Chemical Co., Ltd.) were mixed with methyl ethyl ketone / cyclohexanone =
A solution dissolved in 8 parts by weight of a 4/1 mixed solvent was applied by blade to form a carrier transport layer having a thickness of 20 μm.

Example 2 A photoconductor was prepared in the same manner as in Example 1, except that the resin obtained in Synthesis Example 2 was used instead of the resin obtained in Synthesis Example 1.

Example 3 A photoconductor was prepared in the same manner as in Example 1, except that the resin obtained in Synthesis Example 3 was used instead of the resin obtained in Synthesis Example 1.

Example 4 Example 1 was repeated except that a mixture of dyes represented by the following structural formula was used in place of Y-type titanyl phthalocyanine as the carrier-generating substance in Example 1.
A photoreceptor was prepared in the same manner as described above.

[0061]

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Example 5 A photoconductor was prepared in the same manner as in Example 1, except that dibromoansansthrone was used instead of Y-type titanyl phthalocyanine as a carrier-generating substance.

Example 6 A photoconductor was prepared by the same way as that of Example 1 except that the azo compound represented by the following structural formula was used instead of Y-type titanyl phthalocyanine as the carrier-generating substance.

[0064]

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Example 7 A photoconductor was prepared in the same manner as in Example 1 except that the binder resin obtained in Synthesis Example 4 was used instead of the binder resin of Synthesis Example 1 used for the carrier transport layer in Example 1. It was created.

Example 8 A photoconductor was prepared in the same manner as in Example 1 except that the binder resin obtained in Synthesis Example 5 was used instead of the binder resin of Synthesis Example 1 used for the carrier transport layer in Example 1. It was created.

Example 9 A photoconductor was prepared in the same manner as in Example 1, except that the resin obtained in Synthesis Example 1 was used instead of the butyral resin as the binder resin for the carrier generation layer. .

Comparative Example 1 In Example 1, an untreated phenoxy resin (PK) was used instead of the resin obtained in Synthesis Example 1.
HH (manufactured by UCC) was used, and the solubility in a solvent was poor, and a part of a carrier transporting substance was precipitated in the solution. However, a photoreceptor was prepared using this solution.

(Comparative Example 2) Untreated poly (2-hydroxyethyl methacrylate) was used in Example 7 in place of the resin obtained in Synthesis Example 4, but the solubility was poor and a photoreceptor could not be prepared. .

Comparative Example 3 Although untreated poly (4-hydroxystyrene) was used in Example 8 in place of the resin obtained in Synthesis Example 5, the solubility was poor and a photosensitive member could be prepared. Did not.

(Comparative Examples 4 to 6) In Examples 4 to 6,
A photoconductor was prepared in exactly the same manner except that an untreated phenoxy resin (PKHH: manufactured by UCC) was used in place of the binder resin obtained in Synthesis Example 1.

(Evaluation 1) The samples obtained as described above were evaluated as follows using a paper analyzer EPA-8100 (manufactured by Kawaguchi Electric Co., Ltd.). First -6kV
The surface potential Va immediately after the charging and the surface potential Vi after standing for 5 seconds are obtained under the conditions described above, and then exposure is performed so that the surface illuminance becomes 2 (lux). And the exposure amount E600 / 100 required to lower the surface potential from -600 V to -100 V were determined. D = 100 (Va-vi) / Va
The dark decay rate D was determined from the equation (%). The results are shown in Table 1.

[0073]

[Table 1]

As is clear from the above examples, by using the resin of the present invention, a photosensitive member having good characteristics could be obtained without using a harmful halogen solvent.

Example 10 In Example 1, 1 part by weight of the carrier transporting substance (21), 1.33 parts by weight of the resin obtained in Synthesis Example 1, and isocyanate (7) were used as the carrier transporting layer.
A carrier transport layer obtained in the same manner as in Example 1 except that a solution prepared by dissolving 0.2 part by weight of a solvent in 8 parts by weight of 1,2-dichloroethane solvent was applied by a blade to form a carrier transport layer having a thickness of 20 μm. Was cured at 100 ° C. to 130 ° C. for 2 hours.

Example 11 Synthesis Example 1 of Example 10
A photoconductor was prepared by the same way as that of Example 10 except that the resin obtained in Synthesis Example 2 was used instead of the resin obtained in Example 10, and 0.08 part by weight of isocyanate was used.

Example 12 The procedure of Example 10 was repeated, except that the resin obtained in Synthesis Example 3 was used instead of the resin obtained in Synthesis Example 1, and 0.32 parts by weight of isocyanate was used.
A photoconductor was prepared in the same manner as in No. 10.

Example 13 A photoconductor was prepared by the same way as that of Example 10 except that the isocyanate (1) was used instead of the isocyanate (7).

Example 14 A photoconductor was prepared by the same way as that of Example 10 except that, instead of using isocyanate (7), blocked isocyanate (Coronate 2507: manufactured by Nippon Polyurethane Co.) was used.

Example 15 A photoconductor was prepared by the same way as that of Example 10 except that the dye mixture used in Example 4 was used instead of the Y-type titanyl phthalocyanine as the carrier generating material in Example 10. .

Example 16 A photoconductor was prepared by the same way as that of Example 10 except that dibromoansansthrone was used instead of Y-type titanyl phthalocyanine as the carrier-generating substance.

Example 17 A photoconductor was prepared by the same way as that of Example 10 except that the azo compound used in Example 6 was used instead of the Y-type titanyl phthalocyanine as the carrier-generating substance.

Example 18 The procedure of Example 10 was repeated except that the binder resin obtained in Synthesis Example 4 was used instead of the binder resin of Synthesis Example 1 used for the carrier transport layer, and that 0.1 part by weight of isocyanate was used. A photoconductor was prepared in the same manner as in No. 10.

Example 19 The procedure of Example 10 was repeated, except that the binder resin obtained in Synthesis Example 5 was used instead of the binder resin of Synthesis Example 1 used for the carrier transport layer, and 0.1 part by weight of isocyanate was used. A photoconductor was prepared in the same manner as in No. 10.

Comparative Example 1 In Example 10, an untreated phenoxy resin (PK) was used instead of the resin obtained in Synthesis Example 1.
A photoconductor was prepared in the same manner as in Example 1 except that HH (manufactured by UCC) was used. Precipitation of a carrier transporting substance was observed.

Comparative Example 2 A photoconductor was prepared in the same manner as in Example 16 except that untreated poly (2-hydroxyethyl methacrylate) was used in place of the resin obtained in Synthesis Example 4 in Example 16. As a result, deposition of a carrier transporting substance was observed.

Comparative Example 3 A photoconductor was prepared in the same manner as in Example 17 except that untreated poly (4-hydroxystyrene) was used instead of the resin obtained in Synthesis Example 5 in Example 17. However, precipitation of a carrier transporting substance was observed.

Comparative Example 4 A photoconductor was prepared by the same way as that of Example 10 except that no isocyanate was used.

(Evaluation 2) The samples obtained as described above were evaluated in the same manner as in Examples 1 to 9. Further, the compatibility of the carrier transporting substance with the binder resin in the sample was visually evaluated, and を when a uniform and transparent film was formed, △ when partial precipitation of the carrier transporting substance was observed,
The case where the film was opaque due to the deposition of the carrier transporting substance was evaluated as x. Table 2 shows the results.

[0090]

[Table 2]

(Evaluation 3) The obtained sample was referred to as “KONI
CA 9028 "(manufactured by Konica Corp., using a semiconductor laser light source), the grid voltage VG was adjusted to 600 V, and the unexposed portion potential VH and the exposed portion potential V at the time of light irradiation of 0.7 mW.
L was measured. Next, after repeated use of 10,000 prints, VH and VL were measured, and the scratches on the surface of the photoreceptor were further evaluated. However, the evaluation of scratches was based on the following criteria.

0 pieces / cm ²個 3 pieces / cm ² or less × 4 pieces / cm ² or more The results are shown in Table 3.

[0093]

[Table 3]

As is clear from the above examples, the photoreceptor containing the resin-cured layer of the present invention has excellent sensitivity and potential stability, and also has excellent potential characteristics and durability when used repeatedly. I understand.

[0095]

According to the present invention, good electrical characteristics are obtained.
Using a binder resin that can manufacture an electrophotographic photoreceptor
To obtain excellent electrical characteristics such as temperature, charging property, and potential stability
In addition, it has excellent compatibility with carrier transport materials, and
To provide an electrophotographic photoreceptor having excellent mechanical durability
Can be done. Further, by using the resin of the present invention, it is possible to obtain an electrophotographic photoreceptor having good characteristics without using an environmentally harmful halogen-based solvent, and further having a layer obtained by curing the resin of the present invention, It is possible to obtain an electrophotographic photosensitive member having better electric characteristics and durability.

[Brief description of the drawings]

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

[Explanation of symbols]

 REFERENCE SIGNS LIST 1 conductive support 2 carrier generating layer 3 carrier transporting layer 4, 4 ′, 4 ″ photosensitive layer 5 intermediate layer 6 carrier generating substance 7 carrier transporting substance

Continuation of the front page (56) References JP-A-57-64240 (JP, A) JP-A-4-123065 (JP, A) JP-A-59-81646 (JP, A) JP-A-4-123063 (JP, A) JP-A-51-22442 (JP, A) JP-A-3-129355 (JP, A) JP-A-57-85058 (JP, A) JP-A-4-125564 (JP, A) 57-202544 (JP, A) JP-A-2-256058 (JP, A) JP-A-62-2229154 (JP, A) JP-A-2-256060 (JP, A) JP-A-5-307276 (JP, A A) JP-A-3-28854 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G03G 5/00 CA (STN)

Claims (2)

(57) [Claims] A surface layer containing a binder resin having a repeating unit represented by the following general formula (1) and a carrier transporting substance, wherein 10% or more and 90% or less of the repeating unit is represented by the general formula (1 ′) An electrophotographic photoreceptor, wherein an OH group present in a repeating unit is substituted with another functional group X so as to be a repeating unit represented by (1). Embedded image (Wherein R1 and R2 represent a hydrogen atom or a substituted or unsubstituted alkyl group, aryl group, or phenyl group;
And R2 may combine to form a ring. R3, R4
Represents a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group. X represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or a heterocyclic oxy group. ) 2. The electrophotographic photosensitive member according to claim 1, wherein said binder resin is cured.