JP2000221711A - Composition for charge transfer layer and electrophotographic photoreceptor using that composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prevent failures in the appearance of a coating film after coating and to form a uniform charge transfer layer even when a halogen-based solvent is not used, by incorporating a specified anisole deriv. and other solvents. SOLUTION: The electrophotographic photoreceptor contains an anisole deriv. expressed by the formula and other solvents except for the anisole deriv. In the formula, each of R1 to R5 is independently a hydrogen atom, halogen atom, carboxyl group. -CHO, -CH2COCH3, -CH2OH, -CH=CHCOCH3 or-CH2 CH2COCH3, however, all of R1 to R5 are not hydrogen atoms. As for the solvents except for the anisole deriv. of the formula, solvents are not specially limited, and a non-halogen solvent is preferably used from the viewpoint of influences on the environment. Since whitening in the charge transfer layer depends on the content of the anisole deriv. expressed by the formula in the charge transfer layer, the content is preferably controlled to 0.05 to 10.0 wt.%.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a composition for a charge transport layer and an electrophotographic photosensitive member using the composition.

[0002]

2. Description of the Related Art Many electrophotographic photoreceptors using organic or inorganic materials have been proposed.
A function-separated type photoconductor in which a charge generation layer and a charge transport layer are separated has been put to practical use as a photoconductor of a copying machine or a laser beam printer. As the charge transport material for the charge transport layer, poly-N-vinylcarbazole compounds, pyrazoline derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, styryl derivatives, benzidine derivatives and the like are well known. The charge generation material and the charge transport material generally have no film-forming properties themselves, and are dispersed or dissolved in a solvent together with a binder resin, applied to a conductive substrate, and dried to form a film.

[0003] In recent years, in an electrophotographic process that requires a long life, uniform film formation of the charge transport layer is an important issue. The uniform film forming property of the charge transport layer strongly depends on the composition for the charge transport layer, the binder resin, and the solvent, and therefore, their selection is important. In general, various polycarbonate resins are used as the binder resin of the charge transport layer, and a mixed solvent using a halogen-based solvent is used as the solvent. To form a uniform charge transport layer, temperature and humidity control is also important.

[0004] Furthermore, with the recent increase in the movement for global environmental protection, the elimination of CFCs that destroy the ozone layer and the regulation of halogenated solvents that contaminate groundwater have also been strengthened. A composition for use has not yet been found.

[0005]

According to the first aspect of the present invention, it is possible to prevent whitening of the charge transporting layer, and from the standpoint of environmental protection, to provide a coating film having poor appearance after coating without using a halogenated solvent. And a charge transport layer composition capable of forming a uniform charge transport layer. The invention according to claim 2 provides a composition for a charge transport layer that is more excellent in environmental health in addition to the effects of the invention described in claim 1. The third aspect of the present invention is to provide an electrophotographic photosensitive member which is environmentally friendly, has excellent image characteristics, and is adapted to a high-speed printer requiring high quality and high image quality. The inventions of claims 4 and 5 provide an electrophotographic photoreceptor having more excellent image characteristics in addition to the effects of the invention of claim 3.

[0006]

The present invention provides a compound represented by the general formula (I):

Embedded image [Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen atom, a carboxyl group, —CHO, —
_{CH 2 COCH 3, -CH 2 OH} , -CH = CHCOCH 3
Or —CH ₂ CH ₂ COCH ₃ (provided that R ¹ , R ² ,
R ³ , R ⁴ and R ⁵ are all hydrogen atoms)]] and a composition for a charge transport layer containing a solvent other than the anisole derivative represented by the general formula (I). . Further, the present invention provides a compound represented by the general formula (I)
Wherein the solvent other than the anisole derivative is a non-halogen solvent.

[0007] The present invention also relates to an electrophotographic photoreceptor having a charge transport layer provided using the charge transport layer composition. Further, according to the present invention, the charge transport layer contains the anisole derivative represented by the general formula (I) in an amount of 0.05 to 10.
The present invention relates to the electrophotographic photosensitive member containing 0% by weight.
Further, the present invention provides the charge transport layer, wherein the drying temperature is 70 to 16;
The present invention relates to the electrophotographic photosensitive member provided at 0 ° C.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The anisole derivative used in the present invention has the general formula (I)

Embedded image [Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen atom, a carboxyl group, —CHO, —
_{CH 2 COCH 3, -CH 2 OH} , -CH = CHCOCH 3
Or —CH ₂ CH ₂ COCH ₃ (provided that R ¹ , R ² ,
R ³ , R ⁴ and R ⁵ are each a hydrogen atom (except when all are hydrogen atoms)], and these are commercially available from Nisso Shoji Co., Ltd.

Specific examples of the anisole derivative represented by the general formula (I) include, for example,

Embedded image And the like.

The solvent other than the anisole derivative represented by the above general formula (I) used in the present invention is not particularly limited, and conventionally known solvents can be used. It is preferable to use a system solvent. Further, from the viewpoint of uniform solubility of the composition for a charge transport layer, uniformity of a coating film obtained by dip coating, etc., ketone solvents such as methyl ethyl ketone and ether solvents such as tetrahydrofuran are preferable, and these solvents are preferable. Among them, those having a boiling point of 35 to 100 ° C. are more preferable, and those having a boiling point of 35 to 100 ° C.
Those at 90 ° C. are particularly preferred.

Specific examples of the solvent other than the anisole derivative represented by the above general formula (I) include acetone, methyl ethyl ketone, methyl isobutyl token, tetrahydrofuran, ethyl acetate, toluene, xylene,
Cellosolve, methanol, isopropyl alcohol, isobutyl alcohol, n-butyl alcohol, dioxane, cyclohexanone, cyclohexane and the like can be mentioned. These solvents are used alone or in combination of two or more.

The ratio of the solvent other than the anisole derivative represented by the general formula (I) and the anisole derivative represented by the general formula (I) is determined by the following formula: anisole derivative represented by the general formula (I) / general formula ( It is preferable that the solvent other than the anisole derivative represented by I) = 60/40 to 5/95 (weight ratio). If the amount of the anisole derivative represented by the general formula (I) is too large, a flow (also referred to as sagging) tends to occur when the composition for a charge transport layer is applied, and if too small, the charge transport layer becomes cloudy and white. In addition, the applied charge transport layer tends to be non-uniform.

The whitening of the charge transport layer depends on the content of the anisole derivative represented by the general formula (I) in the charge transport layer, and a certain amount of the anisole derivative represented by the general formula (I) is added to the charge transport layer. By containing it, the whitening phenomenon is greatly improved. The content of the anisole derivative represented by the general formula (I) in the charge transport layer is preferably 0.05 to 10.0% by weight. When the content is less than 0.05% by weight, the effect of preventing whitening tends to be insufficient. On the other hand, when the content exceeds 10.0% by weight, the charge transport layer tends to be uneven. It is particularly preferable that the content of the anisole derivative represented by the general formula (I) be in the range of 0.1 to 8.0% by weight.

As a method for incorporating the anisole derivative represented by the general formula (I) into the charge transporting layer, for example, when a charge transporting layer is prepared, the composition represented by the general formula (I) is used in the composition for the charge transporting layer. An appropriate amount of the anisole derivative represented by the general formula (I) is left in the charge transport layer by adjusting the drying conditions using a solvent containing the anisole derivative represented by the general formula (I). Without using an anisole derivative, the charge transport layer may be made to contain an appropriate amount of the anisole derivative represented by the general formula (I) by a method such as a spray method or a steam bath after the preparation of the charge transport layer. After removing the anisole derivative represented by (I) by drying, there is a method in which an appropriate amount of the anisole derivative represented by the general formula (I) is contained in the charge transport layer.

Here, when the drying conditions are adjusted so that the charge transporting layer contains an appropriate amount of the anisole derivative represented by the general formula (I) in the charge transporting layer, an appropriate amount of the general formula ( The drying temperature is adjusted to preferably 70 to 160 ° C, more preferably 80 to 130 ° C so that the anisole derivative represented by I) is contained. The residual amount of the anisole derivative represented by the general formula (I) in the charge transport layer can be quantified by measuring the weight loss by thermal analysis. Specifically, 10 mg of the charge transport layer was weighed, immediately heated from room temperature to 185 ° C. while flowing nitrogen gas at 200 ml / min, and then kept at the same temperature for 10 minutes to reduce the weight of the charge transport layer. Measure the amount,
This weight loss can be quantified as the residual amount of the anisole derivative represented by the general formula (I).

The anisole derivative represented by the general formula (I) remaining in the charge transport layer can be quantified by gas chromatography. Specifically, 30 mg of the charge transport layer is weighed, immersed in a solvent such as acetone, methyl ethyl ketone, tetrahydrofuran, ethanol or the like, and the remaining solvent is extracted using ultrasonic waves or the like. Then, toluene, benzene, hexane, or the like is added as an internal standard substance to this, and it can be quantified by an internal standard method using gas chromatography.

The total amount of the solvent other than the anisole derivative represented by the general formula (I) and the anisole derivative represented by the general formula (I) is determined by the solid content (non-volatile content) in the charge transport layer composition. Is preferably 5 to 30% by weight, more preferably 15 to 25% by weight, and particularly preferably 18 to 23% by weight. .

Examples of the charge transporting material used in the charge transporting layer include fluorene, fluorenone, 2,7-dinitro-9-fluorenone, and 4H-indeno (1,2,2,3).
6) Thiophene-4-one, 3,7-dinitro-dibenzothiophen-5-oxide, 1-bromopyrene, 2-
Phenylpyrene, carbazole, 3-phenylcarbazole, 2-phenylindole, 2-phenylnaphthalene, oxazole, oxadiazole, oxatriazole, triphenylamine, imidazole, chrysene,
Tetraphen, acridene, various hydrazones, styryl compounds, poly-N-vinylcarbazole, halogenated poly-N-vinylcarbazole, 1-phenyl-3-
(4-diethylaminostyryl) -5- (4-diethylaminophenyl) pyrazoline, polyvinylpyrene, 2-
Phenyl-4- (4-diethylaminophenyl) -5
Phenyloxazole, polyvinyl indoloquinoxaline, 1,1-bis (p-diethylaminophenyl)-
Examples include 4,4-diphenyl-1,3-butadiene, polyvinyl benzothiophene, polyvinyl anthracene, polyvinyl acridine, benzidine, polyvinyl pyrazoline, and derivatives thereof.

As the binder resin for the charge transport layer, a conventionally known binder resin which is dissolved in a solvent other than the anisole derivative represented by the above formula (I) and / or the anisole derivative represented by the above formula (I) is used. Binder) can be used. As such, for example, silicone resin, polyamide resin, polyurethane resin, polyester resin, epoxy resin, polyarylate resin, polyetherimide resin, polyethersulfone resin, polyketone resin, polycarbonate resin, polystyrene resin, polymethacrylate resin , Polyacrylamide resin, polybutadiene resin, polyisoprene resin, melamine resin, benzoguanamine resin, polychloroprene resin, polyacrylonitrile resin, ethyl cellulose resin, nitrocellulose resin, urea resin, phenol resin, phenoxy resin, polyvinyl butyral resin, formal resin, acetic acid Vinyl resin, vinyl acetate / vinyl chloride copolymer, polyester carbonate resin, and the like. These may be used alone or in combination of two or more. It is used to.

The binder resin is preferably used in an amount of 450 parts by weight or less with respect to 100 parts by weight of the charge transporting material so that the electrophotographic characteristics are not deteriorated. It is preferably at least part by weight.

The composition for a charge transport layer of the present invention further comprises:
Known additives such as a plasticizer, a fluidity-imparting material, a pinhole controlling agent, and an antioxidant can be contained as necessary. Each of these additives is preferably used in a range of 10 parts by weight or less based on 100 parts by weight of the charge generating material.

The charge transport layer in the present invention is prepared by uniformly dissolving a charge transport material, a binder resin and additives used as needed in the above-mentioned solvent, and then dip coating the solution on the charge generation layer. It can be formed by coating using a coating method such as a spray coating method, a roll coating method, an applicator coating method, and a wire bar coating method, followed by drying. The thickness of the charge transport layer is usually 5 to 50 μm, preferably 10 to 45 μm, more preferably 12 to 40 μm.
It is. If the thickness is less than 5 μm, the durability tends to be poor, and if it exceeds 50 μm, the light responsiveness tends to be poor.

The present invention also relates to an electrophotographic photosensitive member having a charge transport layer provided by using the composition for a charge transport layer prepared as described above. The electrophotographic photoreceptor of the present invention is obtained by forming a charge generation layer and a charge transport layer after providing an undercoat layer on a conductive substrate as needed.

As the conductive substrate, aluminum, iron,
Metals such as copper and nickel, conductive paper or plastic films, sheets and seamless belts, plastic films laminated with metal foil such as aluminum, sheets and seamless belts, metal plate films, sheets and seamless belts, metal drums, etc. Can be used.

A known undercoat layer can be provided on the conductive substrate as described above. As the undercoat layer, for example, fine particles such as titanium oxide, aluminum oxide, zirconia, titanic acid, zirconic acid, lanthanum lead, titanium black, silica, lead titanate, barium titanate, polyamide resin, phenol resin, casein, melamine resin,
Components such as benzoguanamine resin, polyurethane resin, epoxy resin, cellulose and polyvinyl butyral resin can be used. These fine particles and resins may be used alone or in combination of two or more. In particular, when fine particles are used, a resin is adsorbed on the fine particles and a smooth film can be obtained. Therefore, it is desirable to use the fine particles and the resin together.

As a method of forming the undercoat layer, a solution obtained by dispersing and dissolving the fine particles and / or resin in a solvent is applied onto a conductive substrate by a dip coating method, a spray coating method, a roll coating method, or the like.
It can be formed by applying using a coating method such as an applicator coating method or a wire bar coating method and drying.

Examples of the solvent used at this time include solvents such as acetone, methyl ethyl ketone, methyl isobutyl token, tetrahydrofuran, ethyl acetate, toluene, xylene, cellosolve, methanol, isopropyl alcohol, isobutyl alcohol, and n-butyl alcohol. These solvents are used alone or in combination of two or more. The thickness of the undercoat layer is usually 0.01 to 20.0 μm, preferably 0.1 to 15 μm.
μm. If the thickness is less than 0.01 μm, it tends to be difficult to form an undercoat layer uniformly,
If the thickness exceeds 0.0 μm, the electrophotographic properties tend to decrease.

After forming the undercoat layer as described above,
A charge generation layer can be formed on this layer by applying a coating method such as a dip coating method, a spray coating method, a roll coating method, an applicator coating method, a wire bar coating method, and the like, followed by drying.

The charge generating material used for the charge generating layer is not particularly limited, and examples thereof include azoxybenzene, disazo, trisazo, benzimidazole, quinoline, indigoid, quinacridone, and titanyl phthalocyanine. And phthalocyanine-based, naphthalocyanine-based, pyrrolopyrrole-based, perylene-based, and methine-based organic pigments that generate an electric charge by light irradiation. These may be used alone or in combination of two or more.

For the charge generation layer, a conventionally known binder resin (binder) can be used as necessary. As such, for example, silicone resin, polyamide resin, polyurethane resin, polyester resin, epoxy resin, polyarylate resin, polyetherimide resin, polyethersulfone resin, polyketone resin, polycarbonate resin, polystyrene resin, polymethacrylate resin , Polyacrylamide resin, polybutadiene resin, polyisoprene resin, melamine resin, benzoguanamine resin, polychloroprene resin, polyacrylonitrile resin, ethyl cellulose resin, nitrocellulose resin, urea resin, phenol resin, phenoxy resin, polyvinyl butyral resin, formal resin, acetic acid Vinyl resin, vinyl acetate / vinyl chloride copolymer, polyester carbonate resin, and the like. These may be used alone or in combination of two or more. It is used to.

The binder resin is used in an amount of 5 to 2 parts per 100 parts by mass of the charge generating material so that the electrophotographic characteristics are not deteriorated.
It is preferably used in the range of 00 parts by mass. Further, the same additives as in the charge transport layer, for example, additives such as a plasticizer, a fluidity-imparting agent, and a pinhole controlling agent can be added to the charge generation layer as needed. Each of the additives is preferably used in an amount of 5 parts by mass or less based on the charge generating material.

The thickness of the charge generation layer is usually from 0.01 to
It is 2.0 μm, preferably 0.01 to 1.0 μm.
If the thickness is less than 0.01 μm, it tends to be difficult to form the charge generating layer uniformly, and if it exceeds 2.0 μm, the electrophotographic properties tend to be reduced.

The charge transport layer is formed on the charge generation layer formed as described above by using the above-prepared composition for the charge transport layer by the above method. The thickness of the charge generation layer is generally 5 to 50 μm, preferably 8 to 30 μm.
m. If the thickness is less than 5 μm, the potential is initially lowered, and if it exceeds 50 μm, the electrophotographic characteristics tend to be reduced.

In the electrophotographic photoreceptor of the present invention, a protective layer may be further formed on the above-mentioned photosensitive layer comprising the charge generation layer and the charge transport layer. The thickness of the protective layer is
It is 0.01 to 10 μm, preferably 0.1 to 5 μm. When the thickness is less than 0.01 μm, the effect of the protective layer is small, and the durability tends to be inferior.
The sensitivity tends to decrease and the residual potential tends to increase.

When printing is performed using the electrophotographic photoreceptor of the present invention, after performing charging and exposure in the same manner as in the prior art, development is performed, and an image is transferred onto plain paper and fixed.

[0036]

Next, the present invention will be described in detail with reference to examples. Each material used in the following examples is listed below. The abbreviation is shown in parentheses. (1) Charge generation material τ-type metal-free phthalocyanine (τ-H ₂ Pc) [manufactured by Toyo Ink Co., Ltd.] (2) Charge transport material 1,1-bis (p-diethylaminophenyl) -4,4
-Diphenyl-1,3-butadiene (PBD)

(3) Binder (A) Polyamide resin for undercoat layer, MX1970 (MX1970), solid content 100% by weight [manufactured by Nippon Rilsan Co., Ltd.] Melamine resin, melan 2000 (ML2000) (number of bound formaldehyde is 4. 0, the number of methylol groups is 1.0
Butylamine melamine resin), solid content 50% by weight [manufactured by Hitachi Chemical Co., Ltd.]

(B) Polyester resin for charge generation layer, Vylon 290 (V290), solid content 100% by weight [manufactured by Toyobo Co., Ltd.] Melamine resin, melan 2000 (ML2000) (number of bound formaldehyde 4.0, number of methylol groups 1) Butylamine melamine resin), solid content 50% by weight [manufactured by Hitachi Chemical Co., Ltd.] Melamine resin, melan 365 (ML365), solid content 6
0% by weight [manufactured by Hitachi Chemical Co., Ltd.]

(C) for charge transport layer: polycarbonate resin having the following repeating structure,
S-2050 (TS-2050), solid content 100% by weight
(Made by Teijin Chemicals Limited)

Embedded image

(4) Anisole derivative

Embedded image

Example 1 35 g of MX 1970, 70 g of ML2000 and
1 g of trimellitic acid was completely dissolved in 1800 g of a 1: 1 (weight ratio) mixed solvent of methanol and 1-propanol. This solution was transferred to an aluminum drum (outer diameter 30 mm, length 26
(0 mm, thickness 1 mm), and dried at 120 ° C. for 30 minutes to form a 0.3 μm-thick undercoat layer. next,
50 g τ-H ₂ Pc, 50 g V290, 10 g M
L365 and 1850 g of tetrahydrofuran (TH
F) was dispersed for 10 hours using an ultrasonic disperser. The obtained composition for a charge generation layer was applied on the undercoat layer by a dip coating method, and dried at 140 ° C. for 30 minutes to form a charge generation layer having a thickness of 0.3 μm. Next, 60 g of PBD and 140 g
g of TS-2050 with THF / anisole derivative (A)
= 2: 3 (weight ratio) in 800 g of a mixed solvent. This solution (composition for charge transport layer) was applied on the charge generation layer having the undercoat layer by a dip coating method, and a film thickness of 2
A 0 μm charge transport layer was formed to produce an electrophotographic photoreceptor.

Example 2 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (A)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 19: 1 (weight ratio).

Example 3 An undercoat layer having a thickness of 0.3 μm was formed on an aluminum drum (outer diameter 30 mm, length 260 mm, thickness 1 mm) in exactly the same manner as in Example 1. Next, a charge generation layer having a thickness of 0.3 μm was formed on the undercoat layer in exactly the same manner as in Example 1. Next, 6
0 g of PBD and 140 g of TS-2050 in THF /
The anisole derivative (A) was completely dissolved in 800 g of a mixed solvent of 4: 1 (weight ratio). This solution (the composition for the charge transport layer) is applied on the charge generation layer having the undercoat layer by a dip coating method, and the content of the anisole derivative (A) becomes 0.2% by weight at 120 ° C. The charge transport layer having a film thickness of 20 μm was formed by controlling the thickness of the charge transport layer, thereby producing an electrophotographic photosensitive member.

Example 4 An undercoat layer having a thickness of 0.3 μm was formed on an aluminum drum (outer diameter 30 mm, length 260 mm, thickness 1 mm) in exactly the same manner as in Example 1. Next, a charge generation layer having a thickness of 0.3 μm was formed on the undercoat layer in exactly the same manner as in Example 1. Next, 6
0 g of PBD and 140 g of TS-2050 in THF /
It was completely dissolved in 800 g of a mixed solvent of anisole derivative (A) = 2: 3 (weight ratio). This solution (composition for charge transport layer) is applied on the charge generation layer having the undercoat layer by a dip coating method so that the content of the anisole derivative (A) becomes 8.0% by weight at 80 ° C. The charge transport layer having a film thickness of 20 μm was formed by controlling the thickness of the charge transport layer, thereby producing an electrophotographic photosensitive member.

Example 5 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (A)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 3: 7 (weight ratio).

Example 6 An electrophotographic photosensitive member was prepared in the same manner as in Example 3 except that the drying temperature was 160 ° C. and the content of the anisole derivative (A) was 0.01% by weight. Was prepared.

Example 7 An electrophotographic photoreceptor was prepared in the same manner as in Example 4 except that the drying temperature was 50 ° C. and the content of the anisole derivative (A) was 12.0% by weight. Was prepared.

Comparative Example 1 A mixed solvent of Example 1 was replaced with a THF solvent alone.
An electrophotographic photosensitive member was produced in the same manner as in Example 1.

The appearance, electrophotographic characteristics and image characteristics of the charge transport layer of the electrophotographic photosensitive members obtained in Examples 1 to 7 and Comparative Example 1 were evaluated. The results are shown in Tables 1 and 2.
In Examples 1 and 2, and Comparative Example 1, only the appearance of the coating film was evaluated. The appearance of the coating film was visually observed.

The electrophotographic characteristics were measured by using a light attenuation measuring device (Cynthia 30HC, manufactured by Midoriya Electric Co., Ltd.) to reduce V ₀ −
700 V, dark decay (DDR) at initial and after printing 10,000 sheets
5), residual potential (V _L ) and sensitivity (E ₅₀ ) after 0.2 seconds
Was evaluated. For DDR5, the potential (V ₅ ) after 5 seconds in a dark place was measured and expressed as (V ₅ / V ₀ ) × 100 (%). E
₅₀ indicates that V ₀ is −35 when irradiated with light having a wavelength of 780 nm.
The energy required to reach 0 V is shown. V _L is 2
It shows the surface potential when irradiated with 0 mJ / m ² energy (wavelength 780 nm).

The image characteristics were evaluated on the initial image (fog and solid black density) using an image evaluator (negative charging, reversal development system).

[0052]

[Table 1]

[0053]

[Table 2]

Example 8 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (B)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 9 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (B)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 19: 1 (weight ratio).

Example 10 The mixed solvent of Example 3 was replaced with THF / anisole derivative (B)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 4: 1 (weight ratio).

Example 11 The mixed solvent of Example 3 was replaced with THF / anisole derivative (B)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 12 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (B)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 3: 7 (weight ratio).

Example 13 An electrophotographic photosensitive member was prepared in the same manner as in Example 10 except that the drying temperature was 160 ° C. and the content of the anisole derivative (B) was 0.01% by weight. The body was made.

Example 14 An electrophotographic photosensitive member was prepared in the same manner as in Example 11 except that the drying temperature was changed to 50 ° C. and the content of the anisole derivative (B) was adjusted to 12.0% by weight. The body was made.

The appearance, electrophotographic characteristics and image characteristics of the charge transport layer of the electrophotographic photosensitive members obtained in Examples 8 to 14 were evaluated. The results are shown in Tables 3 and 4. In Examples 8, 9 and 12, only the appearance of the coating film was evaluated. The appearance of the coating film was visually observed.

[0062]

[Table 3]

[0063]

[Table 4]

Example 15 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (C)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 16 The mixed solvent of Example 1 was replaced with THF / anisole derivative (C)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 19: 1 (weight ratio).

Example 17 The mixed solvent of Example 3 was replaced with a THF / anisole derivative (C)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 4: 1 (weight ratio).

Example 18 The mixed solvent of Example 3 was replaced with THF / anisole derivative (C)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 19 The mixed solvent of Example 1 was replaced with THF / anisole derivative (C)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 3: 7 (weight ratio).

Example 20 An electrophotographic photosensitive member was prepared in the same manner as in Example 17, except that the drying temperature was 160 ° C. and the content of the anisole derivative (C) was 0.01% by weight. The body was made.

Example 21 An electrophotographic photosensitive member was prepared in the same manner as in Example 18, except that the drying temperature was changed to 50 ° C. and the content of the anisole derivative (B) was adjusted to 12.0% by weight. The body was made.

The appearance, electrophotographic characteristics and image characteristics of the charge transport layer of the electrophotographic photosensitive members obtained in Examples 15 to 21 were evaluated. The results are shown in Tables 5 and 6. In Examples 15, 16 and 19, only the appearance of the coating film was evaluated. The appearance of the coating film was visually observed.

[0072]

[Table 5]

[0073]

[Table 6]

Example 22 The mixed solvent of Example 1 was replaced with THF / anisole derivative (D)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 23 The mixed solvent of Example 1 was replaced with THF / anisole derivative (D)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 19: 1 (weight ratio).

Example 24 The mixed solvent of Example 3 was replaced with THF / anisole derivative (D)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 4: 1 (weight ratio).

Example 25 The mixed solvent of Example 3 was replaced with THF / anisole derivative (D)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 26 The mixed solvent of Example 1 was replaced with THF / anisole derivative (D)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 3: 7 (weight ratio).

Example 27 An electrophotographic photosensitive member was prepared in the same manner as in Example 24 except that the drying temperature was 160 ° C. and the content of the anisole derivative (D) was 0.01% by weight. The body was made.

Example 28 An electrophotographic photosensitive member was prepared in the same manner as in Example 25 except that the drying temperature was 50 ° C. and the content of the anisole derivative (D) was 12.0% by weight. The body was made.

The appearance, electrophotographic characteristics and image characteristics of the charge transport layer of the electrophotographic photosensitive members obtained in Examples 22 to 28 were evaluated. The results are shown in Tables 7 and 8. In Examples 22, 23, and 26, only the appearance of the coating film was evaluated. The appearance of the coating film was visually observed.

[0082]

[Table 7]

[0083]

[Table 8]

Example 29 The mixed solvent of Example 1 was replaced with THF / anisole derivative (E)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 30 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (E)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 19: 1 (weight ratio).

Example 31 The mixed solvent of Example 3 was replaced with THF / anisole derivative (E)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 4: 1 (weight ratio).

Example 32 The mixed solvent of Example 3 was replaced with THF / anisole derivative (E)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 33 The mixed solvent of Example 1 was replaced with THF / anisole derivative (E)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 3: 7 (weight ratio).

Example 34 An electrophotographic photosensitive member was prepared in the same manner as in Example 31 except that the drying temperature was 160 ° C. and the content of the anisole derivative (E) was 0.01% by weight. The body was made.

Example 35 An electrophotographic photosensitive member was prepared in the same manner as in Example 32 except that the drying temperature was set at 50 ° C. and the content of the anisole derivative (E) was 12.0% by weight. The body was made.

The appearance, electrophotographic characteristics and image characteristics of the charge transport layer of the electrophotographic photosensitive members obtained in Examples 29 to 35 were evaluated. The results are shown in Tables 9 and 10. In addition,
In Examples 29, 30, and 33, only the appearance of the coating film was evaluated. The appearance of the coating film was visually observed.

[0092]

[Table 9]

[0093]

[Table 10]

Example 36 The solvent mixture of Example 1 was replaced with THF / anisole derivative (F)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 37 The mixed solvent of Example 1 was replaced with THF / anisole derivative (F)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 19: 1 (weight ratio).

Example 38 The mixed solvent of Example 3 was replaced with THF / anisole derivative (F)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 4: 1 (weight ratio).

Example 39 The mixed solvent of Example 3 was replaced with THF / anisole derivative (F)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 40 The mixed solvent of Example 1 was replaced with THF / anisole derivative (F)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 3: 7 (weight ratio).

Example 41 An electrophotographic photosensitive member was prepared in the same manner as in Example 38 except that the drying temperature was 160 ° C. and the content of the anisole derivative (F) was 0.01% by weight. The body was made.

Example 42 An electrophotographic photosensitive member was prepared in the same manner as in Example 39 except that the drying temperature was 50 ° C. and the content of the anisole derivative (F) was 12.0% by weight. The body was made.

The appearance, electrophotographic characteristics and image characteristics of the charge transport layer of the electrophotographic photosensitive members obtained in Examples 36 to 42 were evaluated. The results are shown in Tables 11 and 12. In Examples 36, 37, and 40, only the appearance of the coating film was evaluated. The appearance of the coating film was visually observed.

[0102]

[Table 11]

[0103]

[Table 12]

Example 43 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (G)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 44 The mixed solvent of Example 1 was replaced with a THF / anisole derivative (G)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 19: 1 (weight ratio).

Example 45 The mixed solvent of Example 3 was replaced with a THF / anisole derivative (G)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 4: 1 (weight ratio).

Example 46 The mixed solvent of Example 3 was replaced with THF / anisole derivative (G)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to a mixed solvent of 2: 3 (weight ratio).

Example 47 The mixed solvent of Example 1 was replaced with THF / anisole derivative (G)
An electrophotographic photoreceptor was produced in the same manner as in Example 1, except that the mixed solvent was changed to 3: 7 (weight ratio).

Example 48 An electrophotographic photosensitive material was prepared in the same manner as in Example 45 except that the drying temperature was 160 ° C. and the content of the anisole derivative (G) was 0.01% by weight. The body was made.

Example 49 An electrophotographic photosensitive member was prepared in the same manner as in Example 46 except that the drying temperature was 50 ° C. and the content of the anisole derivative (G) was 12.0% by weight. The body was made.

The appearance, electrophotographic characteristics and image characteristics of the charge transport layer of the electrophotographic photosensitive members obtained in Examples 43 to 49 were evaluated. The results are shown in Tables 13 and 14. In Examples 43, 44, and 47, only the appearance of the coating film was evaluated. The appearance of the coating film was visually observed.

[0112]

[Table 13]

[0113]

[Table 14]

[0114]

The composition for a charge transport layer according to claim 1 is
Whitening of the charge transport layer can be prevented, and from the standpoint of environmental protection, the appearance of the coating film after coating can be prevented without using a halogen-based solvent, and a uniform charge transport layer can be formed. The composition for a charge transport layer according to claim 2 exhibits the effect of the composition for a charge transport layer according to claim 1, and is more excellent in environmental health. The electrophotographic photosensitive member according to the third aspect is environmentally friendly, has excellent image characteristics, and is adapted to a high-speed printer requiring high quality and high image quality. Claims 4 and 5
The electrophotographic photoreceptor described above has the same effects as the electrophotographic photoreceptor according to claim 3 and has better image characteristics.

Continued on the front page (72) Inventor Osamu Higashida 4-3-1-1, Higashicho, Hitachi City, Ibaraki Prefecture Inside the Hitachi Chemical Co., Ltd. Yamazaki Plant (72) Inventor Tetsuya Fujii 4-1-1, Higashimachi, Hitachi City, Ibaraki Hitachi (72) Inventor ▲ Susumu Ozaki 4-3-1, Higashi-cho, Hitachi City, Ibaraki Prefecture F-term (reference) 2H068 AA35 BA12 EA14 EA19

Claims (5)

[Claims] 1. A compound of the general formula (I) [Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen atom, a carboxyl group, —CHO, —
_{CH 2 COCH 3, -CH 2 OH} , -CH = CHCOCH 3
Or —CH ₂ CH ₂ COCH ₃ (provided that R ¹ , R ² ,
A composition for a charge transport layer containing a solvent other than the anisole derivative represented by the formula (I) except that R ³ , R ⁴ and R ⁵ are all hydrogen atoms) and the anisole derivative represented by the general formula (I). 2. The charge transport layer composition according to claim 1, wherein the solvent other than the anisole derivative represented by the general formula (I) is a non-halogen solvent. 3. An electrophotographic photoreceptor having a charge transport layer provided by using the composition for a charge transport layer according to claim 1. 4. The electrophotographic photoreceptor according to claim 3, wherein the charge transport layer contains 0.05 to 10.0% by weight of the anisole derivative represented by the general formula (I). 5. The method according to claim 1, wherein the charge transport layer has a drying temperature of 70 to 160.
The electrophotographic photoreceptor according to claim 3 or 4, wherein the temperature is set as ° C.