JPH0611854A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain a photosensitive body having excellent electrification property, high sensitivity and stable performance and showing little deterioration of surface potential or sensitivity even when the body is repeatedly used by incorporating a specified compd. having substituents into a photosensitive layer. CONSTITUTION:The photosensitive body has a layer containing a compd. expressed by formula. In formula, Ar1-Ar4 are aryl groups which may have substituents, Ar5-Ar7 are arylene groups which may have substituents, and R is a hydrogen atom, alkyl group, or aryl group which may have substituents. Substituents in the formula are preferably, alkyl groups, halogen atoms, dialkylamino groups, cyano groups, alkoxy groups, and aryl groups. More preferably, methyl groups, ethyl groups, isopropyl groups, and A-butyl group are selected for the alkyl groups, chlorine, bromine, and iodine for the halogen atoms, dimethylamino and diethylamino groups for dialkylamino groups, methoxy or ethyoxy groups for the alkoxy groups, and phenyl groups or naphthyl groups for the aryl groups.

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 has been used as an electrophotographic photoreceptor.
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 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. It has many advantages such as excellent thermal stability, and poly-N-vinylcarbazole is the most well-known organic photoconductive compound, and 2,4,7- Photoreceptors having a photosensitive layer containing a charge transfer complex formed with 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 is prone to cracking and peeling of the film, and the photoreceptor using this has poor durability. In practice, the residual potential becomes large, and with repeated use, the residual potential is accumulated and the fog gradually becomes larger, 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 a binder commonly used as a material of a 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 required for arranging, crystals of oxadiazole will be deposited 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 a low 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.

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 against repeated use. Absent. Further, these compounds also have a problem in sensitivity at low potential.

As described above, no carrier transport substance having practically satisfactory properties for producing an electrophotographic photoreceptor has been found yet.

[0012]

OBJECTS 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 photoreceptor 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]

[Means for Solving the Problems] As a result of intensive studies in accordance with the above-mentioned object, an electrophotographic photoreceptor containing at least one compound represented by the following general formula [I] has excellent usefulness. I found a thing.

[0016]

[Chemical 2]

In the formula, Ar _{1 to} Ar ₄ are aryl groups which may have a substituent, Ar _{5 to} Ar ₇ are arylene groups which may have a substituent, R is a hydrogen atom, an alkyl group or a substituent. The aryl group which may be possessed is shown.

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

The synthesis examples of the exemplified compounds in the present invention will be described below by the formulas (1) and (2).

[0020]

[Chemical 3]

(Synthesis Example 1) t-Bu was added to a 50 ml four-necked flask.
1.0 g of OK (Kanto Chemical Co., Inc.) and 20 ml of toluene were added and the system was replaced with nitrogen. Compound 1.0g (0.0018mol), 0.6g (0.002
(6 mol) was dissolved in 20 ml of toluene and added dropwise into the system, and the mixture was further 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 give the desired product.
98 g (y = 87%) was obtained. The IR spectrum of the same compound is shown in FIG.

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

(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]

[Chemical 4]

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

[0027]

[Chemical 5]

[0028]

[Chemical 6]

[0029]

[Chemical 7]

[0030]

[Chemical 8]

[0031]

[Chemical 9]

[0032]

[Chemical 10]

[0033]

[Chemical 11]

[0034]

[Chemical 12]

[0035]

[Chemical 13]

[0036]

[Chemical 14]

[0037]

[Chemical 15]

[0038]

[Chemical 16]

[0039]

[Chemical 17]

[0040]

[Chemical 18]

[0041]

[Chemical 19]

[0042]

[Chemical 20]

[0043]

[Chemical 21]

[0044]

[Chemical formula 22]

[0045]

[Chemical formula 23]

[0046]

[Chemical formula 24]

[0047]

[Chemical 25]

[0048]

[Chemical formula 26]

[0049]

[Chemical 27]

[0050]

[Chemical 28]

[0051]

[Chemical 29]

[0052]

[Chemical 30]

[0053]

[Chemical 31]

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

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

As shown in FIGS. 3 (4) 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 photoreceptor 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 intermediate layer 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.

As the binder used here, any binder can be used, but 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 independent. There can be used as a mixture of two or more.

Further, 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. Alternatively, they can be mixed and used.

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 1 part by weight of the carrier generating material is used. The carrier transport substance is preferably 0 to 1 part by weight.

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. If it is more than this, the dark decay and the 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 transport material is preferably 20 to 200 parts by weight, and particularly preferably 30 to 150 parts by weight, per 100 parts by weight of the binder resin in the carrier transport 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 thickness of the photosensitive layer formed 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 and plastic films that 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 may 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 may be contained. Examples of the compound used for such purpose include a chromanol derivative such as tocopherol and an etherified compound or esterified compound thereof, a polyarylalkane compound, a hydroquinone derivative and a mono- and dietherified compound thereof, a benzophenone derivative, a benzotriazole derivative, and a thioether. 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 phenol 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, bulmannyl, 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-Nitrobenzoic acid, p-Nitrobenzoic acid, 3,5-Dinitrobenzoic acid, Pentafluorobenzoic acid, 5-Nitrosalicylic acid, 3,5-Dinitrosalicylic acid, Phthalic acid, Mellitic acid and others JP-A 1-206349 , No. 2-214866, No. 2-13
Examples thereof include compounds having a high electron affinity described in 5362 and US Pat. No. 455,659.

The amount of the electron-accepting substance added is, by 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 transporting layer. The amount of the electron-accepting substance added to the layer is a carrier transporting substance: electron-accepting substance = 100: 0.01 to 1 by weight ratio.
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 further contain a dye for correcting color sensitivity.

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

[0079]

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

Example 1 A vinyl chloride-vinyl acetate-maleic anhydride copolymer "S-REC MF-10" (manufactured by Sekisui Chemical Co., Ltd.) having a thickness of 0.04 was formed on a conductive support obtained by vapor-depositing aluminum on a polyester film. An intermediate layer of μm is provided, and dibromoanthanthrone "Monolight Red 2Y" (C.I.
1.5 g of polycarbonate "Panlite L-1250" (manufactured by Teijin Chemicals Co., Ltd.) 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 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 (5), 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 dried. Was applied to form a carrier-transporting layer and a photoconductor of the present invention was prepared.

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 irradiate it with a halogen lamp 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 2 to 10 Photosensitive members 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 the carrier-transporting substance.

This comparative photoconductor 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 vapor-depositing aluminum on a polyester film.

2 g of the bisazo pigment CGM (1) having the structure shown in "Chemical Formula 33" and 2 g of the 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 would be 0.2 μm.

Exemplary Compound (3) as Carrier Transport Material
In the same manner as in Example 1, a deterioration preventing agent shown in Table 2 was added to the carrier-transporting substance in an amount of 1.5 wt. The same measurement as in Example 1 was performed on this photoconductor.

Examples 12 to 20 Photoreceptors 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 on this photoreceptor.

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

[0095]

[Table 2]

Example 21 Polyamide film "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. 5 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. Next, 7 g of Exemplified Compound (149) as a carrier-transporting substance, 10 g of polycarbonate “Z-200”, and 0.5 g of the deterioration inhibitor shown in Table 3 were further added as a carrier-transporting substance.
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.

This photoreceptor was measured in the same manner as in Example 1.

Example 22 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 on an aluminum drum.

As the carrier transporting material of the present invention, 1 g of the exemplified compound (27) and the polyester resin “Vylon 200” are used.
(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 μm.
A carrier transport layer was formed. On the other hand, 1 g of titanyl phthalocyanine having an X-ray diffraction spectrum shown in FIG. 5 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 -Dichloroethane
After 35 ml was dispersed by using a ball mill, the exemplary compound (140) was further added as a carrier transporting substance so that the concentration was 75 wt% with respect to the binder resin. The dispersion thus obtained was applied onto the above carrier transporting 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 1 except that the charging polarity was positive.

Example 23 A 0.15 μm-thick intermediate layer made of a vinyl chloride-vinyl acetate-maleic anhydride copolymer “S-REC MF-10” (manufactured by Sekisui Chemical Co., Ltd.) was formed on an aluminum drum. on the other hand,
1 g of dibromoanthanthrone "monolite red 2Y" as a carrier-generating substance was ball-milled, and then 3 g of polycarbonate resin "Panlite L-1250",
A liquid of 15 g of monochlorobenzene and 35 g of 1,2-dichloroethane was added and dispersed. To the resulting dispersion, 2 g of the compound 54 as an example of the carrier transporting material of the present invention and 0.1 g of the deterioration inhibitor shown in Table 3 were added, and the mixture was applied onto the above 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 positive.

Table 3 shows the results of Examples 21 to 23 above.

[0105]

[Table 3]

Example 24 Carrier generating material CGM having a structure shown in "Chemical Formula 33"
(2) 1 part and 50 parts of methyl ethyl ketone as a dispersion medium were dispersed using a sand mill, and this was applied onto a polyester base on which aluminum was vapor deposited using a wire bar to form a carrier generation layer having a thickness of 0.3 μm. Then
1 part of Exemplified compound (18), 1.4 parts of 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.) Part was dissolved in 10 parts of 1,2-dichloroethane using a blade coater and dried to a film thickness of 22μ
A m carrier transport layer was formed.

Examples 25 to 33 Photoreceptors 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 photoconductor for comparison was prepared in the same manner as in Example 24 except that the exemplified compound (27) in Example 24 was replaced with the comparative compound (3) shown in "Chemical Formula 32". did.

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

The results of Examples 27 to 33 Comparative Example (3) are shown in Table 4.

[0111]

[Table 4]

[0112]

[Chemical 32]

[0113]

[Chemical 33]

[0114]

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

[Brief description of drawings]

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

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

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

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

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

[Explanation of symbols]

 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 (1)

[Claims] 1. An electrophotographic photoreceptor having a layer containing a compound represented by the general formula [I]. [Chemical 1] [In the formula, Ar _{1 to} Ar ₄ represent an aryl group which may have a substituent, Ar _{1
5 to} Ar ₇ each represent an arylene group which may have a substituent, and R represents a hydrogen atom, an alkyl group or an aryl group which may have a substituent. Further, R and Ar ₄ may form a ring by a bond through another atom. n represents an integer of 1 or 2. ]