JP3177792B2 - Electrophotographic photoreceptor - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an electrophotographic photosensitive member, and more particularly, to an electrophotographic photosensitive member having a photosensitive layer containing a carrier generating substance and a carrier transporting substance.

[0002]

2. Description of the Related Art Conventionally, selenium,
Those having a photosensitive layer containing an inorganic photoconductor such as zinc oxide, cadmium sulfide, or silicon as a main component have been widely known. However, these are not always satisfactory in characteristics such as thermal stability and durability, and also have problems in production and handling.

On the other hand, a photoreceptor having a photosensitive layer containing an organic photoconductive compound as a main component is relatively easy to manufacture, inexpensive, easy to handle, and generally used as a selenium photoreceptor. It has many advantages, such as better thermal stability, and as such an organic photoconductive compound, poly-N-vinylcarbazole is the most well-known, and this is 2,4,7- A photoreceptor having a photosensitive layer mainly composed of a charge transfer complex formed from a Lewis acid such as trinitro-9-fluorenone has already been put to practical use.

On the other hand, there is known a photoconductor having a function-separating type photosensitive layer of a laminated type or a single layer type in which a carrier generating function and a carrier transporting function of the photoconductor are respectively assigned to different substances. A photoreceptor having a photosensitive layer including a carrier generating layer composed of a thin amorphous selenium layer and a carrier transporting layer containing poly-N-vinylcarbazole as a main component has already been put to practical use.

[0005] However, poly-N-vinylcarbazole is
Lack of flexibility, the film is hard and brittle, easily cracks and peeling, and the photoreceptor using this is inferior in durability. In practice, the residual potential increases, and the residual potential accumulates with repeated use, so that the fog gradually increases and the copied image is damaged.

In addition, since low molecular organic photoconductive compounds generally do not have a film-forming ability, they are used in combination with an appropriate binder, and the physical properties or photosensitive characteristics of the film can be improved by selecting the type and composition ratio of the binder. Although it is preferable in that it can be controlled to some extent, types of organic photoconductive compounds having high compatibility with the binder are limited. Photoconductor in reality,
In particular, there are few types of binders that can be used for forming the photosensitive layer of the electrophotographic photosensitive member.

For example, US Pat. No. 3,189,447 describes 2,5
-Bis (p-diethylaminophenyl) -1,3,4-oxadiazole has low compatibility with binders commonly used as materials for the photosensitive layer of the electrophotographic photoreceptor, such as polyester and polycarbonate, and has poor electrophotographic properties. When the photosensitive layer is formed by mixing at a ratio required for conditioning, crystals of oxadiazole come to be precipitated at a temperature of 50 ° C. or more, and have a disadvantage that electrophotographic properties such as charge holding power and sensitivity are reduced. .

On the other hand, the diarylalkane derivative described in US Pat. No. 3,820,989 has little compatibility problem with a binder, but has low stability to light, and is used for repetitive transfer type electrophotography in which charging and exposure are repeated. When it is suitable for the photosensitive layer of the photoreceptor, the sensitivity of the photosensitive layer gradually decreases.

US Patent No. 3,274,000, JP-B-47-3642
No. 8 describes different types of phenothiazine derivatives, but all have the disadvantages of low photosensitivity and low stability upon repeated use.

The stilbene compounds described in JP-A-58-65440 and JP-A-58-198043 have relatively good charge holding power and sensitivity, but they are not satisfactory in durability when used repeatedly. Absent. These compounds also have a problem in sensitivity at low potential.

As a matter of fact, a carrier transporting material having practically satisfactory characteristics for producing an electrophotographic photosensitive member has not been found yet.

[0012]

SUMMARY OF THE INVENTION An object of the present invention is to provide a photosensitive member having high sensitivity.

Another object of the present invention is to provide an electrophotographic photosensitive member having high sensitivity and low residual potential.

Another object of the present invention is to provide an electrophotographic photosensitive member having high repetition stability.

[0015]

Along the Means for solving the problem] The object of a result of extensive studies, the present invention includes at least one and hindered the compound represented in the photosensitive layer by the following general formula [I]
Electrophotographic photoreceptor containing phenolic compound , in photosensitive layer
At least one of the compounds represented by the following general formula [I]
And an electrophotographic photoreceptor containing a hindered amine compound have excellent utility.

[0016]

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In the formula, Ar _{1 to} Ar ₄ represent a phenyl group, a naph
Represents a tyl group or a biphenyl group. However, Ar _{1 to} Ar ₄ are
In the case of a phenyl group, it may have each of the following groups as a substituent
Good. An alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms,
Alkoxy group, dialkylamino group having 1 to 4 carbon atoms, shea
Group, halogen atom. Ar _{5 to} Ar ₇ are a phenylene group,
Represents a naphthylene group or a biphenylene group. However, Ar ₅
When Ar ₇ is a phenylene group, each of the following groups is a substituent
You may have. An alkyl group having 1 to 4 carbon atoms. R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group, a naphthyl group or a biphenyl group. However, when R is a phenyl group, it may have the following groups as substituents. ; Charcoal
Alkyl group having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms
Base. R and Ar ₄ form a ring via each of the following bonds.
May be. _{; -CH 2 -, - CH 2} CH 2 -, - CH =
CH-]

The substituent in the general formula [I] is preferably an alkyl group, a halogen atom, a dialkylamino group, a cyano group, an alkoxy group, an aryl group and the like. More preferably, the alkyl group is a methyl group, an ethyl group, an isopropyl group or the like. Group, A-butyl group, etc.
Bromine, iodine and dialkylamino groups include dimethylamino and diethylamino groups, alkoxy groups include methoxy and ethoxy groups, and aryl groups include phenyl and naphthyl groups, but are not limited to these substituents.

In the following, synthetic examples of the exemplified compounds in the present invention will be described with reference to formulas (1) and (2).

[0020]

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(Synthesis Example 1) t-Bu was placed in a 50 ml four-necked flask.
1.0 g of OK (Kanto Chemical Co., Ltd.) and 20 ml of toluene were added, and the system was replaced with nitrogen. Compound 1.0 g (0.0018 mol), 0.6 g (0.002
6mol) was dissolved in 20 ml of toluene, added dropwise to the system, and then stirred at room temperature for 3 hours.

Thereafter, the organic layer was washed with water, dried and concentrated, and the desired product was isolated by column chromatography.
Recrystallize in a mixed solvent of methanol to obtain the desired product in 0.
98 g (y = 87%) were obtained. FIG. 1 shows the IR spectrum of the compound.

(Synthesis Example 2) A compound (1.0 g, 0.0018 ml), 1.0 g (0.0032 mol) was reacted in the same manner as in the reaction formula (1), and then isolated and purified in the same manner to obtain 0.96 g (y = 76
%)Obtained. FIG. 2 shows the IR spectrum of the compound.

(Synthesis Example 3) A compound represented by Chemical Formula 4 was synthesized in the same manner as described above, and the IR spectrum of the compound is shown in FIG.

[0025]

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Next, specific examples of the compound represented by the general formula [I] according to the present invention will be illustrated.

[0027]

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[0028]

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[0029]

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[0030]

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[0031]

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[0032]

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[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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[0039]

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[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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[0051]

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[0052]

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[0053]

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Although various structures are known for the structure of the electrophotographic photosensitive member, the electrophotographic photosensitive member of the present invention can take any of these forms.

Normally, the configuration is as shown in FIGS. In FIG. 4A and FIG. 4B, a carrier generation layer 2 mainly composed of a carrier generation material is provided on a conductive support 1.
And a photosensitive layer 4 composed of a laminate of a carrier transport layer 3 containing a carrier transport material as a main component.

The photosensitive layer 4 may be provided via an intermediate layer 5 provided on a conductive support, as shown in FIGS. Thus, when the photosensitive layer 4 has a two-layer structure, a photosensitive member having the best electrophotographic characteristics can be obtained.
In the present invention, as shown in FIGS. 5 and 6, the photosensitive layer 4 formed by dispersing the carrier generating substance 7 in a layer 6 containing a carrier transporting substance as a main component is used as a conductive support. 1 may be provided directly or via an intermediate layer 5. In the present invention, a protective layer 8 may be provided as the outermost layer as shown in FIG.

The following are examples of the carrier generating substance used in the carrier generating layer of the photosensitive layer according to the present invention.

(1) Azo dyes such as monoazo dyes, disazo dyes and trisazo dyes (2) Perylene dyes such as perylene anhydride and perylene imide (3) Indigo dyes such as indigo and thioindigo (4) Anthra Polycyclic quinones such as quinone, pyrenequinone and flavanthrone (5) quinacridone dye (6) bisbenzimidazole dye (7) indathrone dye (8) squarylium dye (9) cyanine dye (10) Azurenium-based dyes (11) Triphenylmethane-based dyes (12) Amorphous silicon (13) Phthalocyanine-based pigments such as metal phthalocyanine and metal-free phthalocyanine (14) Selenium, selenium-tellurium, selenium-arsenic (15) CdS, CdSe (16 ) Pyrylium salt dyes, thiapyrylium salt dyes, etc. It can be used alone or in combination of two or more. Since the compound of the present invention has no coating forming ability by itself, a photosensitive layer is formed by combining various binders.

Any binder can be used here, but it is hydrophobic and has a high dielectric constant.
It is preferable to use an electrically insulating film-forming polymer. Examples of such a high-molecular polymer include the following, but are not limited thereto.

(P-1) Polycarbonate (P-2) Polyester (P-3) Methacrylic resin (P-4) Acrylic resin (P-5) Polyvinyl chloride (P-6) Polyvinylidene chloride (P-7) Polystyrene (P-8) Polyvinyl acetate (P-9) Styrene-butadiene copolymer (P-10) Vinylidene chloride-acrylonitrile copolymer (P-11) Vinyl chloride-vinyl acetate copolymer (P-12) Chloride Vinyl-vinyl acetate-maleic anhydride copolymer (P-13) Silicone resin (P-14) Silicone-alkyd resin (P-15) Phenol formaldehyde resin (P-16) Styrene-alkyd resin (P-17) Poly -N-vinylcarbazole (P-18) polyvinyl butyral (P-19) polyvinyl formal These binder resins are used alone. There can be used as a mixture of two or more.

The solvent for forming the carrier generation layer and the transport layer according to the present invention includes N, N-dimethylformamide, acetone, methyl ethyl ketone, cyclohexanone, benzene, toluene, xylene, chloroform, 1,2-dichloroethane. , 1,2-dichloropropane, 1,
1,2-trichloroethane, 1,1,1-trichloroethane, trichloroethylene, tetrachloroethane, dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol, isopropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, methyl cellosolve and the like. , Can also be used as a mixture.

When the photoreceptor of the present invention is a laminated photoreceptor, the weight ratio of the binder and the carrier transporting substance to the carrier generating substance in the carrier generating layer is 0.2 to 5 parts by weight when the carrier generating substance is 1 part by weight. And 0 to 1 part by weight of a carrier transporting substance.

Further, the carrier generating layer may be formed of the carrier generating substance alone.

If the content of the carrier-generating substance is less than 15% (by weight) in the carrier-generating layer, the photosensitivity is low, causing an increase in the residual potential.

The thickness of the carrier generation layer formed as described above is preferably 0.01 to 10 μm, particularly preferably.
0.1 to 5 μm.

The amount of the carrier transporting material is preferably from 20 to 200 parts by weight, particularly preferably from 30 to 150 parts by weight, per 100 parts by weight of the binder resin in the carrier transporting layer.

The thickness of the carrier transport layer to be formed is
It is preferably from 5 to 50 μm, particularly preferably from 10 to 35 μm.

On the other hand, when the photoreceptor of the present invention has a single-layer structure,
The weight ratio of the binder and the carrier transporting substance to the carrier generating substance is preferably 0.2 to 5 parts by weight of the binder and 1 to 5 parts by weight of the carrier transporting substance, when the carrier generating substance is 1 part by weight. Is preferably 5 to 50 μm, particularly preferably 5 to 30 μm.

Examples of the conductive support used in the electrophotographic photoreceptor of the present invention include a metal plate, a metal drum or a conductive polymer including an alloy, a conductive compound such as indium oxide, and aluminum, palladium including an alloy. Paper, plastic film, etc., which are made conductive by applying, depositing or laminating a thin metal layer such as gold.

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, polyamide resin, nylon resin, ethylene-vinyl acetate, etc. Polymer, ethylene-vinyl acetate-maleic anhydride copolymer,
Ethylene resins such as ethylene-vinyl acetate-methacrylic acid copolymer, polyvinyl alcohol, cellulose derivatives and the like are effective.

Organic amines can be added to the photosensitive layer of the present invention for the purpose of improving the carrier generating function of the carrier generating substance. Among the organic amines, it is particularly preferable to add a secondary amine.

Further, the above photosensitive layer contains storability, durability,
For the purpose of improving environmental resistance, a deterioration preventing agent such as an antioxidant and 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 mono- and dietherified compounds thereof, benzophenone derivatives, benzotriazole derivatives, thioethers Compounds, phosphonates, phosphites, phenylenediamine derivatives, phenolic compounds, hindered phenolic compounds, linear amine compounds,
Cyclic amine compounds, hindered amine compounds, and the like are effective. Ao-1 is a specific example of a particularly effective compound.
Hindered phenol compounds such as "IRGANOX 1010", Ao-2 "IRGANOX565" (manufactured by Ciba-Geigy), Ao-3 "Sumilyzer BHT", Ao-4 "Sumilyzer MDP" (manufactured by Sumitomo Chemical), Ao- 5 Hindered amine compounds such as "Sanol LS-2626" and Ao-6 "Sanol LS-622LD" (manufactured by Sankyo). The weight ratio of these compounds to the carrier transporting material is 1: 0.001 to 0.1, preferably 1: 0.05 to 0.1.

In the present invention, one or more kinds of electron-accepting substances can be contained in the carrier-generating layer for the purpose of improving sensitivity, reducing residual potential or reducing fatigue during repeated use, and the like. Examples of the electron accepting substance that can be used here include, for example, succinic anhydride, maleic anhydride,
Dibromo maleic anhydride, phthalic anhydride, tetrachloro phthalic anhydride, tetrabromo phthalic anhydride, 3-nitro phthalic anhydride, 4-nitro phthalic anhydride, pyromellitic anhydride, melitic anhydride, tetracyanoethylene, tetracyanoquinodi Methane, o-dinitrobenzene, m-dinitrobenzene, 1,3,5-trinitrobenzene, paranitrobenzonitrile, piclinkloride, quinone chlorimide, chloranil, bulmanil, dichlorodicyano parabenzoquinone, anthraquinone, dinitroanthraquinone, 2, 7-dinitrofluorenone, 2,4,7-trinitrofluorenone, 2,4,5,7-tetranitrofluorenone, 9
―Fluorenylidene malonodinitrile, polynitro-9
-Fluorenylidene-malonodinitrile, 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 others JP-A 1-206349 No. 2-214866, No. 2-13
No. 5,362, U.S. Pat. No. 455,659.

The amount of the electron accepting substance to be added is, in terms of weight ratio, carrier generating substance: electron accepting substance = 100: 0.01 to 200, preferably 100: 0.1 to 100.

The electron accepting substance may be added to the carrier transport layer. The amount of the electron-accepting substance added to the layer is carrier transporting substance: electron-accepting substance = 100: 0.01 to 1 by weight ratio.
00, preferably 100: 0.1 to 50.

The photoreceptor of the present invention may further contain, if necessary, an ultraviolet absorber for the purpose of protecting the photosensitive layer, and may contain a dye for correcting color sensitivity.

The electrophotographic photoreceptor of the present invention has the above-described structure and, as will be apparent from Examples described later, has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, and particularly when used repeatedly. Also, it has little fatigue deterioration and excellent durability.

Further, the electrophotographic photosensitive member of the present invention can be widely used in application fields such as a laser, a cathode ray tube (CRT), and a photosensitive member of a printer using a light emitting diode (LED) as a light source, in addition to an electrophotographic copying machine. .

[0079]

EXAMPLES The present invention will be described below in more detail with reference to Examples, but it should not be construed that the present invention is limited thereto.

Example 1 A conductive support obtained by vapor-depositing aluminum on a polyester film was coated with a vinyl chloride-vinyl acetate-maleic anhydride copolymer "ESREC MF-10" (manufactured by Sekisui Chemical Co., Ltd.) to a thickness of 0.04. An intermediate layer having a thickness of μm is provided thereon, and dibromoanthranthrone “Monolite Red 2Y” (CI No. 5
1.5 g of polycarbonate "PANLITE L-1250" (manufactured by Teijin Chemicals) was dissolved in a dispersion obtained by adding 1 g of 9300 ICI) to 30 ml of 1,2-dichloroethane and dispersing with a ball mill, and thoroughly mixed. The coating solution was applied so that the film thickness after drying became 2 μm, to form a carrier generation layer.

A solution prepared by dissolving 5 g of Exemplified Compound (5), 10 g of polycarbonate “Z-200” (Mitsubishi Gas Chemical) and 0.5 g of a deterioration inhibitor shown in Table 1 in 80 ml of 1,2-dichloroethane was dried. Was applied to a thickness of 20 μm to form a carrier transporting layer, whereby a photoreceptor of the present invention was prepared.

The photoreceptor thus obtained was evaluated for the following characteristics using EPA-8100 manufactured by Kawaguchi Electric Co., Ltd.
After charging for 5 seconds at a charged voltage of -6 KV, the photosensitive member was left to stand for 5 seconds, and then irradiated with a halogen lamp light so that the illuminance on the surface of the photosensitive member became 2 lux.
/ 2. Further, the residual potential Vr after exposure at an exposure amount of 30 lux · sec was determined.

Examples 2 to 10 Photoconductors were prepared and measured in the same manner as in Example 1 except that the exemplified compounds shown in Table 1 were used instead of the exemplified compound (1).

Comparative Example (1) A comparative photoconductor was prepared in the same manner as in Example 1, except that the comparative compound (1) described in Chemical Formula 32 was used as a carrier transporting substance.

The comparative photoreceptor was measured in the same manner as in Example 1.

Table 1 shows the results of Examples 1 to 10 and Comparative Example (1).
Put together.

[0087]

[Table 1]

Example 11 A 0.1 μm thick intermediate layer made of polyamide resin “A-70” (manufactured by Toray Industries, Inc.) was provided on a conductive support obtained by evaporating aluminum on a polyester film.

2 g of bisazo pigment CGM (1) having the structure shown in Chemical Formula 33 and 2 g of polycarbonate resin “PANLITE L-1250” were mixed with 100 ml of 1,2-dichloroethane and dispersed in a sand grinder for 8 hours. did. This dispersion was applied onto the intermediate layer so that the thickness after drying was 0.2 μm.

Exemplary Compound (3) as Carrier Transport Material
A photoreceptor was prepared in the same manner as in Example 1 by adding 1.5% by weight of a deterioration inhibitor shown in Table 2 to the carrier transporting substance. The same measurement as in Example 1 was performed for this photoconductor.

Examples 12 to 20 Photoconductors were prepared and measured in the same manner as in Example 7, except that the exemplified compounds shown in Table 2 were used instead of the exemplified compound (3).

Comparative Example (2) A comparative photoconductor was prepared in the same manner as in Example 11, except that the comparative compound (2) shown in Chemical Formula 32 was used as the carrier transporting substance.

The same measurement as in Example 1 was performed for this photoreceptor.

Table 2 shows the results of Examples 11 to 20 and Comparative Example (2).

[0095]

[Table 2]

Example 21 A polyamide resin "CM8000" (manufactured by Toray Industries, Inc.) was placed on a conductive support obtained by evaporating aluminum on a polyester film.
An intermediate layer having a thickness of 0.2 μm was provided.

2 g of titanyl phthalocyanine having an X-ray diffraction spectrum shown in FIG. 5 and a silicone resin “KR-5240,
15% xylene-butanol solution ”(Shin-Etsu Chemical Co., Ltd.)
g was dispersed in 100 ml of isopropyl alcohol using a sand mill.
It was applied to a thickness of 0.2 μm. Next, 7 g of the exemplified compound (149), 10 g of polycarbonate “Z-200”, and 0.5 g of a deterioration inhibitor shown in Table 3 were further placed thereon as carrier transporting substances.
It was dissolved in 80 ml of 1,2-dichloroethane. Film thickness after drying is 2
This solution was applied to a thickness of 0 μm to form a carrier transport layer.

The measurement was performed on this photosensitive member in the same manner as in Example 1.

[0099]

[0100]

[0101]

Example 23 An intermediate layer having a thickness of 0.15 μm made of a vinyl chloride-vinyl acetate-maleic anhydride copolymer “ESREC MF-10” (manufactured by Sekisui Chemical Co., Ltd.) was formed on an aluminum drum. on the other hand,
1 g of dibromoanthranthrone "Monolite Red 2Y" as a carrier-generating substance was ball-milled, and then 3 g of a polycarbonate resin "Panlite L-1250".
A dispersion of 15 g of monochlorobenzene and 35 g of 1,2-dichloroethane was added for dispersion. To the obtained dispersion, 2 g of the compound 54 of the carrier transporting substance of the present invention and 0.1 g of a deterioration inhibitor shown in Table 3 were further added, and the resultant was coated on the intermediate layer by a spray coating method and dried. A photosensitive layer having a thickness of 20 μm was formed.

The photoreceptor thus obtained was evaluated in the same manner as in Evaluation 1 except that the charging polarity was set to a positive polarity.

Table 3 shows the results of Examples 21 and 23 described above.

[0105]

[Table 3]

Example 24 Carrier-generating substance CGM having the structure shown in “Formula 33”
(2) One part, and 50 parts of methyl ethyl ketone as a dispersion medium were dispersed by using a sand mill, and the dispersion was applied on a polyester base on which aluminum was deposited by using a wire bar to form a carrier generating layer having a thickness of 0.3 μm. Then
1 part of the exemplified compound (18), 1.4 parts of polycarbonate resin "PANLITE K-1300" (manufactured by Teijin Chemicals Ltd.), and a small amount of silicone oil "KF-54" (manufactured by Shin-Etsu Chemical Co., Ltd.) Part was dissolved in 10 parts of 1,2-dichloroethane using a blade coater and dried.
m carrier transport layer was formed.

Examples 25 to 33 Photoconductors of the present invention were prepared in the same manner as in Example 24, except that the exemplified compound (18) in Example 24 was replaced with the exemplified compounds shown in Table 4.

Comparative Example (3) A comparative photoconductor was prepared in the same manner as in Example 24, except that Exemplified compound (27) in Example 24 was replaced with Comparative compound (3) shown in Chemical Formula 32. did.

The photoreceptor thus obtained was measured in the same manner as in Example 1.

Examples 27 to 33 Table 4 shows the results of Comparative Example (3).

[0111]

[Table 4]

[0112]

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[0113]

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[0114]

The electrophotographic photoreceptor of the present invention has excellent chargeability, high sensitivity, surface potential even when used repeatedly,
Stable performance is obtained with little degradation of sensitivity.

[Brief description of the drawings]

FIG. 1 is an IR spectrum of the compound obtained in Synthesis Example 1.

FIG. 2 is an IR spectrum of the compound obtained in Synthesis Example 2.

FIG. 3 is an IR spectrum of the compound obtained in Synthesis Example 3.

FIG. 4 is a cross-sectional view of a configuration example of a photoconductor of the present invention.

FIG. 5 is an X-ray diffraction spectrum of titanyl phthalocyanine used in Examples.

[Explanation of symbols]

 Reference Signs List 1 support 2 carrier generating layer 3 carrier transporting layer 4 photosensitive layer 5 intermediate layer 6 layer containing carrier transporting substance 7 carrier generating substance 8 protective layer

──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. ⁷ , DB name) G03G 5/00-5/16 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. An electrophotographic method having a photosensitive layer on a conductive support.
In true photoconductor by containing a compound represented by formula (I) in the photosensitive layer and the hindered phenol compound
An electrophotographic photosensitive member characterized by the following. Embedded image [Wherein , Ar _{1 to} Ar ₄ represent a phenyl group, a naphthyl group,
Represents a phenyl group. However, Ar _{1 to} Ar ₄ represent a phenyl group
In such a case, each of the following groups may be present as a substituent. ;carbon
An alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms,
C1-C4 dialkylamino group, cyano group, halogen
Atom. Ar _{5 to} Ar ₇ are a phenylene group, a naphthylene group
Or a biphenylene group. However, Ar ₅ to Ar ₇ are Fe
In the case of a phenylene group, it may have each of the following groups as a substituent.
Good. An alkyl group having 1 to 4 carbon atoms. R is a hydrogen atom, charcoal
An alkyl group having a prime number of 1 to 4 , a phenyl group, a naphthyl group or
Represents a biphenyl group. However, when R is a phenyl group,
May have each group as a substituent. Having 1 to 4 carbon atoms
An alkyl group or an alkoxy group having 1 to 4 carbon atoms. R and Ar ₄ may form a ring via the following bonds . −
_{CH 2 -, - CH 2 CH} 2 -, - CH = CH- ] 2. An electrophotographic method having a photosensitive layer on a conductive support.
In a true photoreceptor, the photosensitive layer is represented by the general formula [I]
It contains a compound and a hindered amine compound
Electrophotographic photoreceptor. Embedded image [ Wherein , Ar _{1 to} Ar ₄ represent a phenyl group, a naphthyl group,
Represents a phenyl group. However, Ar _{1 to} Ar ₄ represent a phenyl group
In such a case, each of the following groups may be present as a substituent. ;carbon
An alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms,
C1-C4 dialkylamino group, cyano group, halogen
Atom. Ar _{5 to} Ar ₇ are a phenylene group, a naphthylene group
Or a biphenylene group. However, Ar ₅ to Ar ₇ are Fe
In the case of a nylene group, it may have the following each group as a substituent.
No. An alkyl group having 1 to 4 carbon atoms. R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group, a naphthyl group or a biphenyl group. However, when R is a phenyl group, it may have the following groups as substituents. A having 1 to 4 carbon atoms
Alkyl group, alkoxy group having 1 to 4 carbon atoms. Also, R and A
r ₄ may form a ring via the following bonds. ;-
_{CH 2 -, - CH 2 CH} 2 -, - CH = CH- ]