JPH06118671A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain an electrophotographic sensitive body high in sensitivity and repetition stability and low in residual potential. CONSTITUTION:The photosensitive layer 4 of the photosensitive body contains a diarylaminobenzenestyryl derivative represented by general formula I in which each of R1-R5 is halogen, alkyl, sulfide, alkoxy, aryl, alkylamino, cyano, aryloxy, or a heterocyclic group; R6 is H or an optionally substituted aromatic or hetero ring; Ar is an optionally substituted aromatic or hetero ring, and Ar and R may form a ring together with each other; each of (l), (m) (n) and (n) is an integer of 0-5; (q) is 0, 1, 2, or 3; and (r) is 0 or 1.

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, at least one of the compounds represented by the general formula [I] which specifies the embodiment of the constituent elements shown in [Chemical formula 1] It has been found that an electrophotographic photosensitive member containing the compound has excellent usefulness.

Among the structural formulas of the compound represented by the above general formula [I], preferable structural formulas are the following general formulas [II] and [III].
Is.

[0017]

[Chemical 2]

[0018] In the formula, R ₁ to R ₄ are the same as R ₁ to R ₄ hydrogen atoms and the general formula [I].

R ₇ and R ₈ represent an alkyl group, an alkoxy group or a halogen atom.

S or t represents an integer of 0-5.

Preferred among R _{1 to} R ₄ are alkyl groups having 1 to 4 carbon atoms, and R ₇ and R ₈ are methyl groups.

Specific examples of the compound according to the present invention will be given below.

Exemplified Compound

[0024]

[Chemical 3]

[0025]

[Chemical 4]

[0026]

[Chemical 5]

[0027]

[Chemical 6]

[0028]

[Chemical 7]

[0029]

[Chemical 8]

[0030]

[Chemical 9]

[0031]

[Chemical 10]

[0032]

[Chemical 11]

[0033]

[Chemical 12]

[0034]

[Chemical 13]

[0035]

[Chemical 14]

[0036]

[Chemical 15]

[0037]

[Chemical 16]

[0038]

[Chemical 17]

The synthesis examples of the exemplified compounds in the present invention are shown below.

(Synthesis Example: Synthesis of Exemplified Compound 1)

[0041]

[Chemical 18]

(ThreeSynthesis of) As shown in the synthesis step,
In a 2-liter four-necked flask, m-phenylenediamine
1108 g (1 mol) and p-iodotolueneTwo654 g (3 mol)
Put, copper powder 63.5g (1 mol) and anhydrous potassium carbonate 138g (1
Mol) and the mixture was stirred at an internal temperature of 190 ° C. for 100 hours. Cooling
Then, extract with toluene and remove excess iodine toluene with steam.
It was removed by distillation. After purification with silica gel column,
Recrystallized with ethanol / ethanol solventThreeWhite crystals of 371g (0.79
Mol) was obtained. (FourIn a 1-liter four-necked flask,Three23.4 g
(0.05 mol) and toluene 300 ml and DMF3.65g (0.05 mol)
Then, the mixture is heated to an internal temperature of 70 ° C with stirring. Internal temperature is above 80 ℃
7.7 g (0.05%) of phosphorus oxychloride, being careful not to let it rise
Mol) is added dropwise. React for 10 hours at an internal temperature of 70 ° C. Post-processing
Is 300 ml of warm water at an internal temperature of 50 ° C, paying attention to the increase in internal temperature.
Is added and stirred for 1 hour. Toluene extraction, water washing, Na₂SO_Four
After drying, attach to a silica gel column,FourTo yellow oil
Thus, 18.4 g (0.037 mol) was obtained. (Synthesis of Exemplified Compound 1) In a 500 ml four-necked flask,Four
With 9.9 g (0.02 mol)56.1 g (0.02 mol) and toluene 200 ml
Put N₂Stir under a stream of air. Next, 2.3 g of t-butoxide
Slowly add a solution of (0.02 mol) in 100 ml of toluene.
To do. After dropping, stir for 20 hours, then add 200 ml of water,
Stir for 3 hours. Toluene extraction, water washing, Na₂SO_FourAfter drying
Attach to a silica gel column and re-use with ascent-ethanol.
Crystallize to give the target Exemplified Compound 1 as yellowish white crystals
To give 9.7 g (0.015 mol). Elemental analysis is as follows
Well matched.

C (carbon) H (hydrogen) N (nitrogen) Measured value (%) 89.01 6.52 4.27 Calculated value (%) 89.13 6.45 4.33 Various structures of the electrophotographic photosensitive member are known,
The electrophotographic photoreceptor of the present invention can take any of those forms.

Normally, the configurations shown in FIGS. 1 (1) to 1 (6) are used. In FIG. 1 (1) and FIG. 1 (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, 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, a protective layer 8 may be provided as the outermost layer as shown in FIG.

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

(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 independent. Alternatively, they can be used as a mixture of two or more kinds.

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.

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, and particularly preferably
It is 0.1 to 5 μm.

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

The thickness of the carrier transport layer formed 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 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, storage stability, 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 electron-accepting substances that can be used here include succinic anhydride, maleic anhydride, dibromomaleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 3-nitrophthalic anhydride, and 4 -
Nitrophthalic anhydride, Pyromellitic dianhydride, Mellitic anhydride, Tetracyanoethylene, Tetracyanoquinodimethane, 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 Acid, pentafluorobenzoic acid, 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, phthalic acid, meritic acid, etc. JP-A 1-206349, 2-214866, 2-135362,
The compounds having a high electron affinity described in US Pat. No. 455,659 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, 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 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 photoconductor of the present invention can be widely used not only in electrophotographic copying machines, but also in other application fields such as lasers, cathode ray tubes (CRTs), and photoconductors for printers using light emitting diodes (LEDs) as light sources. .

[0068]

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) (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 (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 dried. Was applied to form a carrier-transporting layer and a photoconductor 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, 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 determined.

Examples 2 to 6 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) Compound B described below as a carrier transporting substance
A comparative photoconductor was prepared in the same manner as in Example 1 except that -1 was used.

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

The results of Examples 1 to 6 and Comparative Example (1) are shown in Table 1.
Put together.

[0076]

[Table 1]

Example 7 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 G1 having the structure shown in the following [Chemical Formula 20] and 2 g of the polycarbonate resin "Panlite L-1250" were mixed with 100 ml of 1,2-dichloroethane and dispersed 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 Compound (2) 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 8 to 12 Photosensitive members 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 (2).

Comparative Example (2) Compound B-2 described in [Chemical Formula 19] as a carrier-transporting substance
A comparative photoconductor was prepared in the same manner as in Example 7, except that was used.

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

Table 2 shows the results of the above Examples 7 to 12 and Comparative Example (2).

[0084]

[Table 2]

Example 13 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. Next, 7 g of Exemplified Compound (3) as a carrier-transporting substance, 10 g of polycarbonate "Z-200", and 0.5 g of the deterioration preventive agent shown in Table 3 were further added thereto.
-Dissolved in 80 ml dichloroethane. Film thickness after drying is 20μ
This solution was applied so as to have a thickness of m to form a carrier transport layer.

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

Example 14 An 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 substance of the present invention, 1 g of the exemplified compound (16) and the polyester resin “Vylon 200”
(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. 2 as a carrier generating substance, 3 g of polycarbonate “Panlite L-1250” (manufactured by Teijin Chemicals Ltd.) as a binder resin, and 15 ml of monochlorobenzene as a dispersion medium, 1,2 -Dichloroethane
After dispersing 35 ml by using a ball mill, the exemplary compound (16) was further 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 give a film thickness of 2
A carrier generation layer of μm was formed.

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

Example 15 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 "Monolight Red 2Y" as a carrier-generating substance was ball-milled and then polycarbonate resin "Panlite L-1250" 3
g, monochlorobenzene 15g, 1,2-dichloroethane 35g
Was added and dispersed. To the resulting dispersion, 2 g of the compound 22 exemplified as 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 photosensitive member 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 13 to 15 described above.

[0095]

[Table 3]

Example 16 Carrier-generating substance G having the structure described in [Chemical Formula 20]
2; 1 part, 50 parts of 1,2-dichloroethane as a dispersion medium are dispersed using a sand mill, and this is applied onto a polyester base on which aluminum is vapor-deposited using a wire bar,
A carrier generation layer having a film thickness of 0.3 μm was formed. Next, 1 part of Exemplified Compound (1), 1.3 parts of polycarbonate resin "Upilon Z-200" (manufactured by Mitsubishi Gas Chemical Co., Inc.), and a small amount of silicone oil "KF-54" (manufactured by Shin-Etsu Chemical Co., Ltd.) A solution prepared by dissolving 0.05 parts of the agent in 10 parts of 1,2-dichloroethane was applied using a blade coater and dried, and the film thickness was 22 μm.
A m carrier transport layer was formed.

Examples 17 to 21 Photoreceptors of the present invention were prepared in the same manner as in Example 1 except that the exemplified compound (1) in Example 16 was replaced with the exemplified compounds shown in Table 4.

Comparative Example (3) A comparative photoreceptor was prepared in the same manner as in Example 16 except that the exemplified compound (1) in Example 16 was replaced with the following compound.

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

Examples 16 to 21 Table 4 shows the results of Comparative Example (3).
Shown in.

[0101]

[Table 4]

[0102]

[Chemical 19]

[0103]

[Chemical 20]

[0104]

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

FIG. 2 is an X-ray diffraction spectrum diagram of titanyl phthalocyanine used in Examples 13 and 14.

[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 (1)

[Claims] 1. An electrophotographic photoreceptor having a layer containing a compound represented by the general formula [I]. [Chemical 1] [In the formula, R _{1 to} R ₅ represent a halogen atom, an alkyl group, a sulfide group, an alkoxy group, an aryl group, an alkylamino group, a cyano group, an aryloxy group, or a heterocyclic group. R ₆
Represents a hydrogen atom, an aromatic ring which may have a substituent, or a heterocycle. Ar represents an aromatic ring or a heterocycle which may have a substituent. Ar and R ₆ may form a ring with each other. l,
m, n, and p represent the integer of 0-5. q represents an integer of 0 to 3. r represents an integer of 0 or 1. ]