JPH05323635A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To ensure excellent electrification ability and high sensitivity, to almost prevent the deterioration of surface potential and sensitivity even after repeated use and to obtain stable performance by incorporating a specified cyclic bonded compd. of triphenylamine into a photo-sensitive layer. CONSTITUTION:This electrophotographic sensitive body has a layer contg. a compd. represented by the formula, wherein each of R1-R6 is H, halogen, alkyl, alkoxy, aryl or alkylamino, these groups may have substituents, the halogen is preferably Cl, the alkyl is preferably methyl or ethyl, the alkoxy is preferably methoxy or ethoxy, the aryl is preferably phenyl, the alkylamino is preferably dimethylamino or diethylamino, each of l1-l3 is an integer of 0-5 and each of m1-m3 is an integer of 0-4.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention 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 as a main component such as zinc oxide, cadmium sulfide, and silicon have been widely known. However, these are not always satisfactory in terms of properties such as thermal stability and durability, and have problems in manufacturing 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 a selenium photoreceptor. Compared with many advantages such as excellent thermal stability, as such an organic photoconductive compound, poly-N-vinylcarbazole is the most well known, and 2,4,7- Photoreceptors having a photosensitive layer containing a charge transfer complex formed from a Lewis acid such as trinitro-9-fluorenone as a main component have already been put into practical use.

On the other hand, there is known a photoreceptor having a laminated type or single layer type function-separated type photosensitive layer in which a carrier generating function and a carrier transporting function of the photoconductor are shared by separate substances. Photoreceptors having a photosensitive layer composed of a carrier generation layer composed of a thin amorphous selenium layer and a carrier transport layer containing poly-N-vinylcarbazole as a main component have already been put into practical use.

However, poly-N-vinylcarbazole is
It lacks flexibility, its coating is hard and brittle, and it easily causes cracks and peeling of the film, and the photoreceptor using it has poor durability.If a plasticizer is added to improve this defect, electrophotographic process In practice, the residual potential becomes large, and the residual potential is accumulated with repeated use, and fogging gradually increases, damaging the copied image.

Since a low molecular weight organic photoconductive compound generally has no film forming ability, it is used in combination with an appropriate binder, and the physical properties or photosensitivity of the film can be controlled by selecting the kind and composition ratio of the binder. Although it is preferable in that it can be controlled to some extent, the types of organic photoconductive compounds having high compatibility with the binder are limited. In reality, the photoreceptor
In particular, there are few kinds of binder that can be used for the construction of the photosensitive layer of the electrophotographic photosensitive member.

For example, 2,5 described in US Pat. No. 3,189,447
-Bis (p-diethylaminophenyl) -1,3,4-oxadiazole has low compatibility with binders that are commonly used as the material of the photosensitive layer of an electrophotographic photoreceptor, such as polyester and polycarbonate, and has electrophotographic properties. When the photosensitive layer is formed by mixing the components in a ratio necessary for arranging, crystals of oxadiazole will be precipitated at a temperature of 50 ° C. or higher, and there is a drawback that electrophotographic properties such as charge retention and sensitivity are deteriorated. ..

On the other hand, the diarylalkane derivative described in US Pat. No. 3,820,989 has few compatibility problems with the binder, but has little stability to light and is repeatedly charged and exposed for repeated transfer electrophotography. When it is suitable for the photosensitive layer of the above-mentioned photoreceptor, it has a drawback that the sensitivity of the photosensitive layer gradually decreases.

Also, US Pat. No. 3,274,000, Japanese Patent Publication No. 47-3642
No. 8 describes different types of phenothiazine derivatives, but they all have the drawbacks of low photosensitivity and low stability during repeated use.

The stilbene compounds described in JP-A-58-65440 and JP-A-58-198043 are relatively good in charge retention and sensitivity, but are not satisfactory in durability after repeated use. Absent. Further, these compounds also have a problem in sensitivity at low potential.

As described above, in reality, no carrier transport material having practically satisfactory properties for producing an electrophotographic photosensitive member has been found.

[0012]

OBJECT OF THE INVENTION It is an object of the present invention to provide a highly sensitive photoreceptor.

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 repeat stability.

[0015]

As a result of intensive studies conducted in accordance with the above-mentioned object, the object of the present invention is to find out the general formula [I] in which the respective constituent elements shown in the above-mentioned "Chemical formula 1" to "Chemical formula 3" are specified. ], [II] or [III] is contained in the electrophotographic photosensitive member having a layer containing the compound.

In the general formula [I], preferred substituents represented by R _{1 to} R ₆ are chlorine atom for a halogen atom, methyl or ethyl group for an alkyl group, and methoxy for an alkoxy group.
Examples of the ethoxy group and the aryl group include a phenyl group, and examples of the alkylacino group include a dimethylamino group and a diethylamino group, but the substituents are not limited thereto.

Next, specific examples of the compound represented by the general formula [I] will be given.

[0018]

[Chemical 4]

The synthetic examples of the exemplified compounds of the present invention belonging to the general formula [I] are shown below.

[0020]

[Chemical 5]

As shown in the above reaction formula, in a 200 ml four-necked flask, 10 g of copper powder, 22 g of K ₂ CO ₃ , 9.9 g (0.02 mol) of compound (1),
Compound (2) (5.2 g, 0.02 mol) was added, and the mixture was heated with stirring at about 180 ° C. for 40 hours. The mixture was allowed to cool, extracted with toluene, and then the desired product was isolated by column chromatography and recrystallized from ethanol to obtain 7.8 g of white crystals (yield 77%).

In the general formula [II], preferred substituents represented by R _{1 to} R ₆ are chlorine atom for halogen atom, methyl and ethyl group for alkyl group, methoxy and ethoxy group for alkoxy group, and aryl group for Examples of the phenyl group and the alkylamino group include dimethylamino and diethylamino groups, but the substituents are not limited to these. Next, specific examples of the compound represented by the general formula [II] are listed.

[0023]

[Chemical 6]

The synthesis examples of the exemplified compounds belonging to the general formula [II] are shown below.

[0025]

[Chemical 7]

As shown in the above reaction formula, copper powder 10 g, K ₂ CO ₃ 22 g, compound (1) 10.9 g (0.02 mo) in a 200 ml four-necked flask.
l) and 7.6 g (0.02 mol) of compound (2) were added, and the mixture was heated and stirred at about 180 ° C. for 40 hours. The mixture was allowed to cool, extracted with toluene, and then the desired product was isolated by column chromatography and recrystallized to obtain 8.3 g (yield 64%) of pale yellow crystals.

In the general formula [III], preferred substituents represented by R _{1 to} R ₆ are chlorine atom for halogen atom, methyl or ethyl group for alkyl group, methoxy or ethoxy group for alkoxy group, and phenyl for aryl group. Examples of the group and alkylamino group include dimethylamino and diethylamino groups, but the substituents are not limited to these.

Specific examples of the compound represented by the general formula [III] will be given below.

[0029]

[Chemical 8]

The synthetic examples of the exemplified compounds belonging to the general formula [III] are shown below.

[0031]

[Chemical 9]

As shown in the above reaction formula, copper powder 10 g, K ₂ CO ₃ 22 g, compound (1) 13.2 g (0.02 mo) in a 200 ml four-necked flask.
l) and 1.86 g (0.02 mol) of compound (2) were added, and the mixture was heated and stirred at about 200 ° C. for 50 hours. The solution was allowed to cool, extracted with toluene, and then recrystallized in a toluene-methanol mixed solvent to obtain 9.2 g (yield 46%) of pale yellow crystals.

Various forms of the structure of the electrophotographic photosensitive member are known, and the electrophotographic photosensitive member of the present invention can take any of these forms.

Normally, the configurations shown in FIGS. 1 (1) to 1 (6) are used. In FIG. 1 (1) and FIG. 2 (2), a carrier generating layer 2 containing a carrier generating substance as a main component is formed on a conductive support 1.
And a carrier transporting layer 3 containing a carrier transporting material as a main component, a photosensitive layer 4 is provided.

As shown in FIGS. 3 (3) and (4), the photosensitive layer 4 may be provided via an intermediate layer 5 provided on a conductive support. Thus, when the photosensitive layer 4 has a two-layer structure, a photosensitive member having the most excellent electrophotographic characteristics can be obtained.
Further, in the present invention, as shown in FIGS. 5 (6) and 6 (6), a 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. It may be provided directly on the substrate 1 or via the intermediate layer 5. Further, in the present invention, the protective layer 8 may be provided as the outermost layer as shown in FIG.

Examples of the carrier-generating substance used in the carrier-generating layer of the photosensitive layer according to the present invention are as follows.

(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 flavanthrons (5) Quinacridone dyes (6) Bisbenzimidazole dyes (7) Induslone dyes (8) Squarylium dyes (9) Cyanine dyes (10) Azurenium dye (11) Triphenylmethane dye (12) Amorphous silicon (13) Phthalocyanine pigments such as metal phthalocyanine and metal-free phthalocyanine (14) Selenium, selenium-tellurium, selenium-arsenic (15) CdS, CdSe (16) ) Pyrylium salt dye, thiapyrylium salt dye, etc. It can be used alone or in combination of two or more. Since the compound of the present invention does not have the ability to form a coating by itself, various binders are combined to form a photosensitive layer.

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

(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 There can be used as a mixture of two or more.

As the solvent for forming the carrier generating layer and the transporting layer according to the present invention, N, N-dimethylformamide, acetone, methyl ethyl ketone, cyclohexanone, benzene, toluene, xylene, chloroform, 1,2-dichloroethane is used. , 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,
It 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 material to the carrier generating material in the carrier generating layer is 0.2 to 5 parts by weight of the binder when the carrier generating material is 1 part by weight. The carrier transport substance is preferably 0 to 1 part by weight.

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% (weight) in the carrier-generating layer, the photosensitivity is low and the residual potential is increased, and if it is more than this, dark decay and receptive potential are lowered.

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

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

The thickness of the formed carrier transport layer is
It is preferably 5 to 50 μm, particularly preferably 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 material to the carrier generating material is preferably 0.2 to 5 parts by weight of the binder and 1 to 5 parts by weight of the carrier transporting material when the carrier generating material is 1 part by weight, and the film thickness of the formed photosensitive layer. Is preferably 5 to 50 μm, particularly preferably 5 to 30 μm.

As the conductive support used in the electrophotographic photosensitive member of the present invention, a metal plate containing an alloy, a metal drum or a conductive polymer, aluminum containing a conductive compound such as indium oxide or an alloy, palladium, Examples thereof include paper, plastic film and the like which are made conductive by applying a thin metal layer such as gold, vapor deposition or lamination.

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 Polymer, ethylene-vinyl acetate-maleic anhydride copolymer,
Ethylene resins such as ethylene-vinyl acetate-methacrylic acid copolymers, 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, in the above-mentioned photosensitive layer, storability, durability,
For the purpose of improving the environmental resistance, a deterioration inhibitor such as an antioxidant or a light stabilizer can be contained. Examples of the compound used for such a purpose include chromanol derivatives such as tocopherol and its etherified compounds or esterified compounds, polyarylalkane compounds, hydroquinone derivatives and their mono- and dietherified compounds, benzophenone derivatives, benzotriazole derivatives and thioethers. Compounds, phosphonates, phosphites, phenylenediamine derivatives, phenol compounds, hindered phenol compounds, linear amine compounds,
Cyclic amine compounds and hindered amine compounds are effective. Specific examples of particularly effective compounds include Ao-1
"IRGANOX 1010", Ao-2 "IRGANOX565" (manufactured by Ciba Geigy), Ao-3 "Sumilyzer BHT", Ao-4 "Sumilyzer MDP" (manufactured by Sumitomo Chemical Co., Ltd.), hindered phenolic compounds, Ao- 5 Examples include hindered amine compounds such as “Sanol LS-2626” and Ao-6 “Sanol LS-622LD” (manufactured by Sankyo Co.). The weight ratio of these compounds to the carrier transport substance is 1: 0.001-0.1, preferably 1: 0.05-0.1.

In the present invention, the carrier-generating layer may contain one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential or reducing fatigue during repeated use. Examples of the electron accepting substance that can be used here include succinic anhydride, maleic anhydride, and
Dibromo maleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 3-nitrophthalic anhydride, 4-nitrophthalic anhydride, pyromellitic dianhydride, meritic anhydride, tetracyanoethylene, tetracyanoquinodi Methane, o-dinitrobenzene, m-dinitrobenzene, 1,3,5-trinitrobenzene, paranitrobenzonitrile, picrin chloride, quinone chlorimide,
Chloranil, bulmanil, dichlorodicyanoparabenzoquinone, anthraquinone, dinitroanthraquinone, 2,
7-dinitrofluorenone, 2,4,7-trinitrofluorenone, 2,4,5,7-tetranitrofluorenone, 9-fluorenylidene malonodinitrile, polynitro-9-fluorenylidene-malonodinitrile, picric acid, o-nitro Benzoic acid, p-nitrobenzoic acid, 3,5-dinitrobenzoic acid, pentafluorobenzoic acid, 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, phthalic acid, mellitic acid, etc.
6349, 2-214866, 2-135362, US Patent 45
The compounds having a high electron affinity described in No. 5,659 can be mentioned.

The amount of the electron-accepting substance added is, by weight ratio, carrier generating substance: electron-accepting substance = 100: 0.01 to 200,
It is preferably 100: 0.1 to 100.

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

In addition, the photoreceptor of the present invention may further contain an ultraviolet absorber or the like for the purpose of protecting the photosensitive layer, if necessary, and may also contain a dye for color sensitivity correction.

The electrophotographic photosensitive member of the present invention has the above-mentioned constitution and, as will be apparent from the examples described later, is excellent in charging property, sensitivity property and image forming property, and particularly when repeatedly used. Moreover, it has little fatigue deterioration and excellent durability.

Further, the electrophotographic photoreceptor of the present invention can be widely used not only in electrophotographic copying machines, but also in other application fields such as a photoreceptor of a printer using a laser, a cathode ray tube (CRT), and a light emitting diode (LED) as a light source. ..

[0058]

EXAMPLES The present invention will be specifically described below with reference to examples, but the embodiments of the present invention are not limited thereby.

In the examples, the groups I to III of the respective examples represented by the general formulas [I] to [III] are assembled, and conditions a and numbers corresponding to the conditions and numbers are set in each group. , C, d, e and f
An example of the mold is given. That is, regarding the examples having the same description order in each mold in each group, the conditions other than those shown in each table are the same, and the same evaluation is performed.

Example group I: §a type Example I-1 A vinyl chloride-vinyl acetate-maleic anhydride copolymer "S-REC MF-10" was formed on a conductive support obtained by vapor-depositing aluminum on a polyester film. (Made by Sekisui Chemical Co., Ltd.) is provided with an intermediate layer having a thickness of 0.04 μm, and dibromoanthanthrone “monolight red 2Y” (CI.
1.5 g of polycarbonate "Panlite L-1250" (manufactured by Teijin Chemicals Co., Ltd.) was dissolved in a dispersion liquid 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 liquid was applied so that the film thickness after drying was 2 μm to form a carrier generation layer.

A solution prepared by dissolving 5 g of the exemplified compound (I-1), 10 g of polycarbonate "Z-200" (Mitsubishi Gas Chemical Co., Ltd.) and 0.5 g of the deterioration inhibitor shown in Table 1 in 80 ml of 1,2-dichloroethane was then added. A carrier transporting layer was formed by coating so as to have a film thickness after drying of 20 μm to prepare a photoreceptor of the present invention.

The photoreceptor thus obtained was subjected to the following characteristic evaluation using EPA-8100 manufactured by Kawaguchi Electric Co., Ltd.
After charging for 5 seconds at a charged voltage of -6 KV, left it for 5 seconds in the dark, and then irradiating it with halogen lamp light so that the illuminance on the surface of the photoconductor becomes 2 lux. Initial surface potential Va, half exposure amount E1
I asked for / 2. Further, the residual potential Vr after exposure with an exposure amount of 30 lux · sec was obtained.

Examples I-2 to I-5 Photoreceptors were prepared in the same manner as in Example I-1, except that the exemplified compounds shown in Table 1 were used instead of the exemplified compound (I-1).
It was measured.

Comparative Example I- (1) A comparative photoconductor was prepared in the same manner as in Example I-1 except that the R _I compound shown in “Chemical Formula 10” was used as the carrier-transporting substance.

This comparative photoconductor was measured in the same manner as in Example I-1.

The results of Examples I-1 to I-5 and Comparative Example I- (1) are summarized in Table 1.

§B type Example I-6 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 vapor-depositing aluminum on a polyester film. ..

2 g of a bisazo pigment CG-705 having a structure shown in "Chemical Formula 11" and a polycarbonate resin "Panlite L"
-1250 "2 g and 100 ml of 1,2-dichloroethane,
Disperse with a sand grinder for 8 hours. This dispersion was applied onto the intermediate layer so that the thickness after drying would be 0.2 μm.

Exemplary compounds (I-
Using 6), the deterioration preventive agent shown in Table 1 was added to the carrier transporting substance in an amount of 1.5 wt% to prepare a photoconductor in the same manner as in Example I-1. This photoreceptor was also measured in the same manner as in Example I-1.

Examples I-7 to I-10 Except that the exemplified compound shown in Table 1 was used instead of the exemplified compound (I-6), a photoreceptor was prepared and measured in the same manner as in Example I-6. did.

Comparative Example I- (2) A comparative photoconductor was prepared in the same manner as in Example I-6 _except that the compound R _I was used as the carrier transport material.

The same measurement as in Example I-1 was performed on this photoreceptor.

Examples I-6 to I-10 and Comparative Example I-
The results of (2) are shown in Table 1.

§C type Example I-11 Polyamide resin "CM8000" (manufactured by Toray Industries Inc.) on a conductive support obtained by vapor-depositing 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. 2 and a silicone resin "KR-5240,"
20 of "15% xylene-butanol solution" (manufactured by Shin-Etsu Chemical Co., Ltd.)
g was dispersed in 100 ml of isopropyl alcohol using a sand mill, and this dispersion was dried on the intermediate layer to give a thickness after drying.
It was applied to have a thickness of 0.2 μm. Then, 7 g of the exemplified compound (I-11) as a carrier-transporting substance, 10 g of polycarbonate "Z-200", and 0.5 g of the deterioration inhibitor shown in Table 1 were further added.
Was dissolved in 80 ml of 1,2-dichloroethane. This solution was applied so that the film thickness after drying would be 20 μm to form a carrier transport layer.

The measurement of this photoreceptor was carried out in the same manner as in Example I-1.

§ d type Example I-12 On the aluminum drum, a 0.2 μm thick intermediate layer made of ethylene-vinyl acetate-methacrylic acid copolymer resin “Elvax 4260” (manufactured by Mitsui DuPont Chemical Co., Ltd.) was formed.

As the carrier transporting material of the present invention, 1 g of the exemplified compound (I-12) and the polyester resin “Vylon 20” are used.
0 "(manufactured by Toyobo Co., Ltd.) 1.5 g dissolved in 10 ml of 1,2-dichloroethane is applied on the intermediate layer, dried, and then the film thickness is 15
A μm carrier transport layer was formed. On the other hand, 1 g of titanyl phthalocyanine having an X-ray diffraction spectrum shown in FIG. 2 as a carrier generating substance, 3 g of polycarbonate “Panlite L-1250” (manufactured by Teijin Chemicals) as a binder resin, and 15 ml of monochlorobenzene as a dispersion medium, 1,2 -Disperse 35 ml of dichloroethane using a ball mill and then
The exemplified compound (I-12) was added as a carrier-transporting substance so as to be 75 wt% with respect to the binder resin. The dispersion thus obtained was applied onto the above carrier transport layer by a spray coating method to form a carrier generating layer having a film thickness of 2 μm.

The photosensitive member thus obtained was evaluated in the same manner as in Example I-1 except that the charging polarity was positive.

§E type Example I-13 A 0.15 μm thick intermediate layer made of vinyl chloride-vinyl acetate-maleic anhydride copolymer “S-REC MF-10” (manufactured by Sekisui Chemical Co., Ltd.) was placed on an aluminum drum. Formed. on the other hand,
1 g of dibromoanthanthrone "Monolight Red 2Y" as a carrier-generating substance was ball-milled and then polycarbonate resin "Panlite L-1250" 3 g,
A liquid of 15 g of monochlorobenzene and 35 g of 1,2-dichloroethane was added and dispersed. The obtained dispersion liquid was further mixed with 2 g of the compound I-14 as an example of the carrier transporting substance of the present invention and Table 1.
0.1 g of the deterioration preventive agent shown in 1) was added, the solution was applied onto the above intermediate layer by a spray coating method and dried to form a photosensitive layer having a thickness of 20 μm.

The photosensitive member thus obtained was evaluated in the same manner as in Evaluation 1 except that the charging polarity was positive.

The results of Examples I-11 to I-13 above are shown in Table 1.
Shown in.

§F type Example I-14 Carrier generating substance BIPP1 having the structure shown in Chemical formula 11
Parts, 50 parts of methyl ethyl ketone as a dispersion medium is dispersed using a sand mill, and this is applied onto a polyester base on which aluminum is vapor-deposited using a wire bar to obtain a film thickness of 0.
A 3 μm carrier generation layer was formed. Next, 1 part of Exemplified Compound (15) and polycarbonate resin “Panlite K-
1300 "(manufactured by Teijin Chemicals) and a small amount of silicone oil" KF-54 "(manufactured by Shin-Etsu Chemical Co., Ltd.) 0.05 parts of the deterioration inhibitor shown in Table 1 dissolved in 10 parts of 1,2-dichloroethane After coating with a coater and drying, a carrier transport layer having a thickness of 22 μm was formed.

Examples I-15 to I-18 The present invention was carried out in the same manner as in Example I-1 except that the exemplified compound (I-15) in Example I-14 was replaced by the exemplified compound shown in Table 1. The photoconductor was created.

Comparative Example I- (4) A comparative photoconductor was prepared in the same manner as in Example I-14 except that the exemplified compound (I-15) in Example I-14 was replaced with the compound R _I. Created.

The photosensitive member obtained as described above is used as an example.
It measured like I-1.

Examples I-14 to I-18 The results of Comparative Example I- (3) are shown in Table 1.

[0088]

[Table 1]

Example Group II: §a type §b type §c type §d type §e type §f type Specifications and characteristics are shown in "Chemical formula 10" and Table 2.

[0090]

[Table 2]

Example group III: §a type §b type §c type §d type §e type §f type Specifications and characteristics are shown in “Chemical formula 10” and Table 3.

[0092]

[Table 3]

[0093]

[Chemical 10]

[0094]

[Chemical 11]

[0095]

The electrophotographic photosensitive member of the present invention has excellent charging ability and high sensitivity, and has a surface potential,
Stable performance is obtained with little deterioration in sensitivity.

[Brief description of drawings]

FIG. 1 is a sectional view of a constitutional example of a photoconductor of the present invention.

FIG. 2 is an X-ray diffraction spectrum diagram of titanyl phthalocyanine used in Examples.

[Explanation of Codes] 1 Support 2 Carrier Generation Layer 3 Carrier Transport Layer 4 Photosensitive Layer 5 Intermediate Layer 6 Layer Containing Carrier Transport Material 7 Carrier Generation Material 8 Protective Layer

Claims (3)

[Claims] 1. An electrophotographic photoreceptor having a layer containing a compound represented by the general formula [I]. [Chemical 1] [In the general formula [I], R _{1 to} R ₆ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group or an alkylamino group, and these groups may have a substituent. l _{1 to} l ₃ represent an integer of 0 to 5 and m _{1 to} m ₃ represent an integer of 0 to 4. ] 2. An electrophotographic photoreceptor having a layer containing a compound represented by the general formula [II]. [Chemical 2] [In the general formula [II], R _{1 to} R ₆ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group or an alkylamino group, and these groups may have a substituent. l _{1 to} l ₃ represent an integer of 0 to 5 and m _{1 to} m ₃ represent an integer of 0 to 4. ] 3. An electrophotographic photoreceptor having a layer containing a compound represented by the general formula [III]. [Chemical 3] [In the general formula [III], R _{1 to} R ₁₀ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group or an alkylamino group, and these groups may have a substituent. Also, a plurality of substituents may be introduced into one phenyl ring. ]