JP3087341B2 - Laminated photoreceptor - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a laminate type photoreceptor having a charge generating layer and a charge transporting layer provided on a conductive support, and a charge transporting material used for forming the charge transporting layer and a binder for binding the same. The combination of the binder resins.

[0002]

2. Description of the Related Art Conventionally, there have been known photoconductors having a photosensitive layer mainly composed of an inorganic photoconductive substance and those having a photosensitive layer mainly composed of an organic photoconductive substance. Inorganic materials have disadvantages such as high toxicity, poor film-forming property, lack of flexibility, and high production cost.

On the other hand, studies on the use of an organic photoconductive substance typified by a polyvinyl carbazole compound for a photosensitive layer of a photoreceptor have been advanced and have already been put to practical use. In general, organic photoconductive materials have better transparency, are lighter and have better film formability than inorganic photoconductive materials, but are inferior in sensitivity, durability and stability due to environmental changes. Therefore, high sensitivity and repetitive stability, in which the charge generation function and the charge transport function in the photoconductive function are separately assigned to different substances,
A function-separated type photoconductor with excellent durability has been developed. In the function-separated type photoreceptor, a charge generating layer containing a charge generating material and a photosensitive layer in which a charge transporting layer containing a charge transporting material is laminated, or a charge generating material and a charge transporting material are used. Some have a photosensitive layer contained in a binder resin.

However, even in the above-mentioned function-separated type laminated photoreceptor, unevenness in film thickness of the photoreceptor, poor cleaning of the surface of the photoreceptor, and unevenness of density and the like on an image due to deterioration due to humidity and ozone, etc., occur. When several hundred copies are continuously made, there are problems such as shading of the image and blurring of the image.

[0005] In the case where the photosensitive member is used as a photosensitive member of a laser printer or the like which is required to have high image quality reliability and repetition stability, such a problem is increased. It was started.

The above problems are largely caused by the coating state of the photosensitive layer, especially the charge transport layer, for example, the coating accuracy and the scratches, abrasion and deterioration due to mechanical and physical external forces during printing. This greatly depends on the characteristics of the binder resin used for forming the photosensitive layer.

Therefore, in order to solve such a problem,
Various binder resins including polycarbonate have been studied.

[0008]

However, when a charge transport material having poor matching with the binder resin is used,
The coating solution of the composition has poor coating properties, so-called "repelling" is likely to occur on the photosensitive layer, and white spots are generated on the copied image ("repelling" means that a crater-shaped concave portion is formed on the coating surface when the photosensitive layer is coated). Phenomena that occur). Further, the coating liquid has poor coating preservability, and if it is stored for a long time, even after being adjusted and mixed and dissolved, repelling occurs again.

Therefore, an object of the present invention is to solve the above-mentioned problems and to provide a high sensitivity, cleaning property and abrasion resistance by using a charge generation layer in which a specific binder resin and a specific charge transport material are combined. Another object of the present invention is to provide a photoreceptor having excellent durability, low fatigue due to repeated use, and stable electrophotographic characteristics.

[0010]

Means for Solving the Problems In a laminate type photoreceptor in which a charge generation layer and a charge transport layer are provided on a conductive support, the charge transport layer is at least one kind represented by the following general formula (I). A distyryl compound,

[0011]

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(Wherein, Ar ₁ and Ar ₂ each represent an alkyl group or an aryl group which may have a substituent. Ar ₃ represents an alkyl group, an aralkyl group or an aryl group which may each have a substituent. R ₁ and R ₂ each represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom, and R ₃ represents a hydrogen atom, an alkyl
Group, an alkenyl group, an alkynyl group, a thioether group, off
Enoxy group, aryl which may have a substituent
Group, aralkyl group, alkoxy group or heterocyclic group
You. However, when R ₃ is a substituent,

Embedded image Except for an aryl group having A) A laminated photoconductor comprising at least one kind of polycarbonate resin represented by the following general formula as a binder resin.

[0013]

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(Wherein R ₄ , R ₅ , R ₆ , R ₇ , R ₁₀ , R
₁₁ , R ₁₂ and R ₁₃ are each a hydrogen atom, an alkyl group,
Represents an aryl group or a halogen atom . R ₈ and R ₉ represent an alkyl group, a cyclic alkyl group or an aryl group which may have a substituent, and R ₈ and R ₉ may form a cyclic alkyl group which may have a substituent. Where R ₈ and
R ₉ is a methyl group and R ₄ , R ₅ , R ₆ , R ₇ , R ₁₀ , R
_11, except when R ₁₂ and R ₁₃ are all hydrogen atoms.
N and m each represent a number of moles of 10 to 1,000. The polycarbonate resin represented by the general formula (II) used for the charge transport layer of the photoreceptor of the present invention is prepared by using a diol compound represented by the following general formulas (III) and (IV) by a general method such as a phosgene method. It can be synthesized by copolymerization according to a typical polycarbonate synthesis method.

[0015]

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(In the formula, R _{4 to} R ₁₃ have the same meanings as (II).) Examples of the polycarbonate resin represented by the general formula (II) used in the photoreceptor of the present invention include the following.

[0017]

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[0018]

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[0019]

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[0020] In the present invention, configured in a variety of repeat units, such as the ^{1 × 10 4 ~1 × 10 5} , preferably polycarbonate resins having a number average molecular weight of 2 × 10 ⁴ ~8 × 10 ⁴ Used, more preferably 2-4 × 1
A polycarbonate resin having a number average molecular weight of 0.4 to ⁴ × 6.5 × 10 ⁴ is mixed and used. When the number average molecular weight is smaller than 1 × 10 ⁴ , the hardness of the film becomes soft and the durability is deteriorated. On the other hand, when the number average molecular weight is larger than 1 × 10 ⁵ , the viscosity becomes high, the coating property is poor, and it becomes difficult to apply uniformly.

The above polycarbonate resin may be used in combination with another resin. When the content of the polycarbonate resin is less than 50% by weight of the entire resin in the charge generation layer, the hardness of the film itself is reduced, the durability is deteriorated, and the sensitivity is reduced. To be used. Examples of the resin that can be used in combination with the polycarbonate resin include a polystyrene resin, a polymethyl methacrylate resin, a polyester resin, a polyarylate resin, and a phenoxy resin.

The charge transporting material used in the charge transporting layer of the photoreceptor of the present invention contains at least one distyryl compound represented by the above general formula (I).

Each of the distyryl compounds represented by the above general formula (I) has a structural feature in that it is asymmetric around a nitrogen atom. As a result, the three-dimensional structure is small, and crystallization can be suppressed in the binder, so that good compatibility with the binder is exhibited. The distyryl compound represented by the general formula (I) used for the photoreceptor of the present invention is specifically shown below, but it should not be construed that the invention is limited thereto.

[0024]

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[0025]

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[0026]

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[0027]

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[0028]

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[0029]

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[0030]

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[0031]

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[0032]

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[0033]

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Hereinafter, the case of forming the laminated photoreceptor according to the present invention in which the charge generation layer and the charge transport layer are laminated on the conductive support will be specifically described.

The laminated photoreceptor of the present invention is prepared by vacuum-depositing a charge generating material on a conductive support or dispersing it in a suitable solvent or, if necessary, a solution in which a binder resin is dissolved. The applied coating solution is applied and dried to form a charge generation layer. At this time, the thickness of the charge generation layer is 0.01 to 2 μm.
m, preferably 0.1 to 1 μm. If the amount of the charge generation material used is too small, the sensitivity is poor.If the amount is too large, the chargeability is deteriorated, or the mechanical strength is weakened. 0 to 10 parts by weight, preferably 0 to 5 parts by weight, per 1 part by weight of the generated material.

On the charge generation layer thus formed, a distyryl compound represented by the general formula (I) as a charge transporting material and a polycarbonate resin represented by the general formula (II) as a binder resin are suitably applied. A solution dissolved in a suitable solvent is applied and dried to form a charge transport layer, thereby producing a laminated photoconductor of the present invention. At this time, the thickness of the charge transport layer is 3 to 40 μm.
m, preferably 5 to 30 μm. Further, the ratio of the distyryl compound in the charge transport layer is set to be 0.02 to 2 parts by weight, preferably 0.03 to 1.2 parts by weight, based on 1 part by weight of the binder resin. The charge transport layer may contain known antioxidants, sensitizers, thickeners, surfactants, anti-curl agents, ultraviolet absorbers, plasticizers, leveling agents, and the like.

The photoreceptor of the present invention may have a constitution in which an intermediate layer is provided on a conductive support, whereby the adhesion, the coating property, the protection of the support, and the support side are improved. The charge injection into the photosensitive layer can be improved.

As the material used for the intermediate layer, polyimide, polyamide, nitrocellulose polyvinyl butyral, polyvinyl alcohol, aluminum oxide and the like are suitable, and the film thickness is preferably 1 μm or less.

Further, the photoreceptor of the present invention may be provided with a surface protective layer. As the material used for the surface protective layer, acrylic resin, polyaryl resin, polycarbonate resin, polymers such as urethane resin as it is,
Alternatively, a material in which a low-resistance compound such as tin oxide or indium oxide is dispersed is suitable.

Further, an organic plasma polymerized film can be used. The organic plasma polymerized film is appropriately oxygen if necessary,
It may contain nitrogen, halogen, atoms of groups III and V of the periodic table. The thickness of the surface protective layer is desirably 5 μm or less.

In the laminated photoreceptor of the present invention, the charge transport layer and the charge generation layer on the conductive support may be laminated in this order.

As the conductive support used for the photoreceptor of the present invention, a sheet or a drum made of copper, aluminum, iron, nickel or the like or a plate is used. In addition, these metals are attached to a plastic film or the like by vacuum evaporation, electroless plating, or the like,
Alternatively, a layer in which a layer of a conductive compound such as a conductive polymer, indium oxide, or tin oxide is provided on a support such as paper or a plastic film by coating or vapor deposition, or the like can be used.

Examples of the charge generating material used in the photoreceptor of the present invention include bisazo pigments, triarylmethane dyes, thiazine dyes, oxazine dyes, xanthene dyes, cyanine dyes, styryl dyes, and pyrylium dyes. Organic substances such as dyes, azo dyes, chiacdrine dyes, indigo dyes, perylene dyes, polycyclic quinone pigments, bisbenzimidazole pigments, indathrone pigments, squarylium pigments, phthalocyanine pigments, and pyrrolopyrrole pigments And inorganic substances such as selenium, selenium / tellurium, selenium / arsenic, cadmium sulfide, and amorphous silicon. In addition, any material that absorbs light and generates charge carriers with a very high probability can be used.

The binder resin used in the production of the laminated photoreceptor of the present invention is electrically insulating, and is measured by 1 × 10
It is desirable to have a volume resistance of ¹² Ω · cm or more. For example, a binder such as a thermoplastic resin, a thermosetting resin, a photocurable resin, or a photoconductive resin known per se can be used. Specifically, saturated polyester resin, polyamide resin, acrylic resin, ethylene-vinyl acetate resin, ion-crosslinked olefin copolymer (ionomer), styrene-butadiene block copolymer, polycarbonate,
Thermoplastic resins such as vinyl chloride-vinyl acetate copolymer, cellulose ester, polyimide, and styrene resin; heat of epoxy resin, urethane resin, silicone resin, phenol resin, melamine resin, xylene resin, alkyd resin, thermosetting acrylic resin, etc. Curable resin; photocurable resin; photoconductive resins such as polyvinyl carbazole, polyvinylpyrene, polyvinylanthracene, and polyvinylpyrrole; and the like, and these binder resins are used alone or in combination of two or more.

When the charge transporting material is a polymeric charge transporting material that can be used as a binder, it is not necessary to use another binder resin.

The photoreceptor of the present invention can be used together with a binder resin together with a plasticizer such as halogenated paraffin, polychlorinated biphenyl, dimethylnaphthalene, dibutyl phthalate, O-terphenyl, chloranyl, tetracyanoethylene, 2,4,7-.
Electron withdrawing sensitizers such as trinitrofluorenone, 5,6-dicyanobenzoquinone, tetracyanoquinodimethane, tetrachlorophthalic anhydride, 3,5-dinitrobenzoic acid, methyl violet, rhodamine B, cyanine dye, pyrylium salt, A sensitizer such as a thiapyrylium salt may be used.

The solvent for dissolving these resins varies depending on the type of the resin. For example, alcohols such as methanol, ethanol, and iso-propyl alcohol;
Acetone, methyl ethyl ketone, ketones such as cyclohexane, N, N-dimethylformamide, amides such as N, N-dimethylacetamide, sulfoxides such as dimethyl sulfoxide, tetrahydrofuran, dioxane,
Ethers such as ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, chloroform, methylene chloride, dichloroethylene, carbon tetrachloride,
Aliphatic halogenated hydrocarbons such as trichloroethylene,
Or benzene, toluene, xylene, ligroin,
Aromatic substances such as monochlorobenzene and dichlorobenzene can be used.

Hereinafter, a method for synthesizing the distyryl compound represented by the above-mentioned distyryl compound example [8] will be described.

The following formula:

[0050]

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4.03 g of the aldehyde compound represented by
And the following formula:

[0052]

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3.04 g of a phosphonate compound represented by the following formula:
Was dissolved in 40 ml of dimethylformaldehyde. While cooling the resulting solution below 5 ° C., calcium-ter-butoxide 1.6 in 20 ml of dimethylformamide.
A suspension containing 8 g was added dropwise and stirred at room temperature for 8 hours. After stirring at room temperature for 4 hours, the mixture was reacted at 80 ° C. for 2 hours to complete the reaction. The obtained mixture was barged in 500 ml of ice water, neutralized with dilute hydrochloric acid, and after about 30 minutes, the precipitated crystals were filtered, the filtered product was washed with water, dissolved in benzene, and separated by silica gel column chromatography. did.

After benzene was distilled off from the effluent, it was recrystallized from acetonitrile to obtain 2.9 g of pale yellowish white crystals (yield: 52%).
%).

The results of the elemental analysis are as follows.

[0056]

[Table 1]

[0057]

EXAMPLES The distyryl compounds of the present invention used in the following Examples are those synthesized according to the above-mentioned Synthesis Examples or methods similar thereto.

Embodiment 1

[0059]

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0.45 parts by weight of a bisazo compound represented by the above formula (V), a polyester resin (Vylon 200,
0.45 parts by weight) and 50 parts by weight of cyclohexanone were dispersed using a sand grinder. The obtained dispersion liquid of the bisazo compound is 100 μm thick.
m was applied using a film applicator to a dry film thickness of 0.3 g / m ² and then dried to form a charge generation layer. A solution obtained by dissolving 50 parts by weight of the distyryl compound [2] and 70 parts by weight of the polycarbonate resin represented by the chemical formula (1-1) in 400 parts by weight of 1,4-dioxane and 100 parts by weight of cyclohexanone was dried thereon. Coating was performed so as to have a thickness of 20 μm, followed by drying to form a charge transporting layer. Thus, a laminated photoconductor having a two-layered photosensitive layer was manufactured.

The photoreceptor thus prepared was used as a commercially available electrophotographic copying machine (EP-470Z manufactured by Minolta Camera Co., Ltd.).
Is charged by a −6 Kv corona discharge, and the initial surface potential V ₀ (v), the exposure amount required to attenuate the surface potential to half of the initial surface potential (hereinafter, the half-exposure amount) E
The decay rate DDR ₁ (%) of the initial potential when left in the dark for _1/2 (Lux · sec) for 1 second was measured. Table 3 shows the results.

Further, the photosensitive member in Example 1 and Examples 2 and 11 and Comparative Examples 2, 5 and 6 described later are described in a commercially available electrophotographic copying machine (EP-540 manufactured by Minolta Camera Co., Ltd.).
An actual photograph was repeatedly taken at the time of negative charging according to 0). For each photoconductor, V ₀ before and after 10000 actual shootings,
E _1/2 , residual potential V _R (v) and film thickness were measured, and the results are shown in Table 6. In addition, image characteristics after actual shooting of 10,000 sheets were evaluated.

In the photosensitive members of Examples 1, 2, and 11,
As in the case of the initial image, the final image was excellent in gradation, with no change in sensitivity, a clear image was obtained, and it was confirmed that the photoreceptor of the present invention was stable in the repetition characteristics.

Examples 2 to 5 The same as Example 1 except that the distyryl compounds [3], [4], [5] and [7] were used in place of the distyryl compound [1] used in Example 1. Four kinds of laminated photoreceptors were produced by the above method.
For each photosensitive member, V ₀ , E
_1/2 and DDR ₁ were measured and the results are shown in Table 3.

Embodiment 6

[0066]

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0.45 parts by weight of the bisazo compound represented by the above formula (VI) and 0.45 parts by weight of polyvinyl butyral were dispersed together with 50 parts by weight of cyclohexanone by a sand grinder. The obtained dispersion liquid of the bisazo compound was applied on a 100-μm-thick aluminized mylar using a film applicator so that the dry film thickness was 0.3 g / m ^2, and then dried to form a charge generation layer. On top of this, 40 parts by weight of the distyryl compound [8] and the above-mentioned chemical formula
A solution obtained by dissolving 60 parts by weight of the polycarbonate resin represented by (1-2) in 500 parts by weight of 1,4-dioxane is
Dip coating was performed so that the dry film thickness became 20 μm, followed by drying to form a charge transport layer, thereby producing a photoconductor having a two-layer photosensitive layer. V ₀ , E _1/2 , and DDR ₁ of this photoreceptor were measured in the same manner as in Example 1, and the results are shown in Table 3.

Examples 7 to 10 The same as Example 1 except that the distyryl compounds [9], [12], [15] and [20] were used in place of the distyryl compounds [8] used in Example 6. Four kinds of laminated photoreceptors were produced by the above method. For each photosensitive member, V
₀ , E _1/2 and DDR ₁ were measured and the results are shown in Table 3.

Example 11 A mixture of 1 part by weight of τ-type metal-free phthalocyanine, 0.5 part by weight of polyvinyl butyral and 50 parts by weight of tetrahydrofuran (THF) was dispersed by a sand grinder. Using a film applicator on the resulting phthalocyanine-based dispersion liquid on an aluminized mylar having a thickness of 100 μm,
Coating was performed so that the dry film thickness became 0.2 g / m ² , followed by drying to form a charge generation layer. On top of this, the distyryl compound [2]
3] 60 parts by weight of the polycarbonate resin represented by the chemical formula (1-4) and 40 parts by weight of dichloroethane 500
The solution dissolved in parts by weight was applied so as to have a dry film thickness of 25 μm, and dried to form a charge transport layer, thereby producing a laminated photoreceptor having a two-layer photosensitive layer. For this photoreceptor, V ₀ , E _1/2 , DD were obtained in the same manner as in Example 1.
R ₁ was measured and the results are shown in Table 3.

Examples 12 to 15 The same procedures as in Example 11 were carried out except that the distyryl compounds [24], [26], [27] and [30] were used in place of the distyryl compound [23] used in Example 11. Four kinds of laminated photoreceptors were produced by the above method. For each of the photosensitive member in the same manner as in Example 1 were measured _{V 0, E 1/2,} DDR 1 The results are shown in Table 3.

Example 16 0.5 part by weight of titanyl phthalocyanine pigment, 0.2 part by weight of phenoxy resin and 0.3 part by weight of polyvinyl butyral resin
Parts by weight were dispersed together with 50 parts by weight of cyclohexanone using a sand grinder. The obtained dispersion liquid of titanyl phthalocyanine pigment was applied on a 100 μm-thick aluminized mylar using a film applicator so that the dry film thickness became 0.25 g / m ^2, and then dried to form a charge generation layer. . On top of this, the distyryl compound [34] 70
Parts by weight, the molecular weight 2400 represented by the chemical formula (1-6)
25 parts by weight of a polycarbonate resin having the formula
A solution obtained by dissolving 45 parts by weight of a polycarbonate resin having a molecular weight of 45000 represented by (1-7) in 400 parts by weight of 1,4-dioxane and 100 parts by weight of cyclohexanone,
Coating was performed so that the dry film thickness became 20 μm, and drying was performed to form a charge transporting layer. Thus, a laminated photoconductor having a two-layer photosensitive layer was manufactured. For this photoreceptor, V ₀ , E _1/2 , and DDR ₁ were measured in the same manner as in Example 1, and the results were shown in Table 3.
Shown in

Examples 17 to 20 The same procedures as in Example 16 were carried out except that the distyryl compounds [37], [41], [43] and [44] were used instead of the distyryl compounds [34] used in Example 16. Four kinds of laminated photoreceptors were produced by the above method. V ₀ , E _1/2 , and DDR ₁ were measured for each photoreceptor in the same manner as in Example 1, and the results are shown in Table 4.

Example 21 0.5 parts by weight of dibromanthanthrone and 0.5 parts by weight of a polyvinyl butyral resin were dispersed together with 50 parts by weight of cyclohexanone using a sand grinder. Using a film applicator, apply a dry film thickness of 0.8 g / m ² on an aluminized mylar having a thickness of 100 μm.
And dried to form a charge generation layer.
On this, 40 parts by weight of a distyryl compound [46], 20 parts by weight of a polycarbonate resin having a molecular weight of 20,000 represented by the chemical formula (1-8), and 50 parts by weight of a polycarbonate resin 50 having a molecular weight of 40,000 represented by the chemical formula (1-1)
Parts by weight of a solution obtained by dissolving 500 parts by weight of tetrahydrofuran in a dry state to have a dry film thickness of 20 μm, followed by drying to form a charge transport layer. Was prepared. V ₀ , E _1/2 , and DDR ₁ of this photoreceptor were measured in the same manner as in Example 1, and the results are shown in Table 4.

Examples 22 to 25 The same procedures as in Example 1 were carried out except that the distyryl compounds [10], [11], [13] and [16] were used instead of the distyryl compounds [46] used in Example 21. Four kinds of laminated photoreceptors were produced by the above method. For each of the photosensitive member in the same manner as in Example 1 were measured _{V 0, E 1/2,} DDR 1 The results are shown in Table 4.

Example 26 On the charge generation layer of Example 1, 30 parts by weight of a distyryl compound [38] as a charge transporting material, and the general formula (1-13)
50 parts by weight of a polycarbonate resin and a methyl methacrylate resin (BR-85, manufactured by Mitsubishi Rayon) 2
A solution obtained by dissolving 0 parts by weight in 500 parts by weight of tetrahydrofuran was applied so as to have a dry film thickness of 20 μm, and dried to form a charge transport layer, thereby producing a photoconductor having a two-layer photosensitive layer. . V ₀ , E _1/2 , and DDR ₁ of this photoreceptor were measured in the same manner as in Example 1, and the results are shown in Table 4.

Example 27 As a charge transporting material, 40 parts by weight of a distyryl compound [5], 60 parts by weight of a polycarbonate resin represented by the above general formula (1-1) and a polyester resin ( (Byron 200, manufactured by Toyobo) A solution prepared by dissolving 10 parts by weight in 500 parts by weight of tetrahydrofuran is applied so as to have a dry film thickness of 20 μm, and dried to form a charge transport layer. A photoreceptor was prepared. V ₀ , E _1/2 , and DDR ₁ of this photoreceptor were measured in the same manner as in Example 1, and the results are shown in Table 4.

Example 28 On the charge generation layer of Example 1, 50 parts by weight of a distyryl compound [50] as a charge transporting material, and the general formula (1-10)
A solution obtained by dissolving 70 parts by weight of a polycarbonate resin represented by the following formula in 500 parts by weight of tetrahydrofuran is applied so as to have a dry film thickness of 20 μm, and dried to form a charge transporting layer. A photoreceptor was produced. With respect to this photoreceptor, V ₀ ,
E _1/2 and DDR ₁ were measured, and the results are shown in Table 4.

Example 29 50 parts by weight of a distyryl compound [37] and 70 parts by weight of a polycarbonate resin represented by the above general formula (1-7) were used as a charge transport material on the charge generating layer of Example 1 in 500 parts by weight of tetrahydrofuran. Of the solution dissolved in
The resultant was coated so as to have a thickness of 0 μm and dried to form a charge transport layer, thereby producing a photoconductor having a two-layer photosensitive layer. With respect to this photoreceptor, V ₀ ,
E _1/2 and DDR ₁ were measured, and the results are shown in Table 4.

Example 30 20 parts by weight of a distyryl compound [23] and a distyryl compound [2] were formed on the charge generation layer of Example 1 as charge transport materials.
4] A solution prepared by dissolving 20 parts by weight and 70 parts by weight of the polycarbonate resin represented by the above general formula (1-10) in 500 parts by weight of tetrahydrofuran is applied so as to have a dry film thickness of 20 μm, and dried to cause charge transport. Forming a layer, 2
A photoreceptor having a photosensitive layer composed of layers was prepared. V ₀ , E _1/2 , DDR of this photoreceptor were obtained in the same manner as in Example 1.
₁ was measured and the results are shown in Table 4.

Example 31 On the charge generation layer of Example 1, 40 parts by weight of a distyryl compound [3], 30 parts by weight of a polycarbonate resin represented by the above general formula (1-7), and A solution prepared by dissolving 30 parts by weight of the polycarbonate resin represented by (1-13) in 500 parts by weight of dichloroethane is applied so as to have a dry film thickness of 20 μm, and dried to form a charge transport layer. A photosensitive member having a photosensitive layer was prepared. V ₀ , E _1/2 , and DDR ₁ were measured for this photoreceptor in the same manner as in Example 1, and the results are shown in Table 4 in Comparative Examples 1 to 6. Instead of the resin used for the charge transport layer in Example 1, Then, six types of laminated photoconductors were produced in the same manner as in Example 1 except that the following resins were used. V ₀ , E _1/2 , and DD were obtained for each photosensitive member in the same manner as in Example 1.
R ₁ was measured and the results are shown in Table 5.

[0081]

[Table 2]

Comparative Examples 7 to 11 Instead of the distyryl compound [2] used in Example 1, the following distyryl compounds (2-1), (2-2) and (2-
Except for using 3), (2-4) and (2-5), five types of laminated photoconductors were produced in the same manner as in Example 1. V ₀ , E _1/2 , D
DR ₁ was measured and the results are shown in Table 5.

[0083]

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[0084]

[Table 3]

[0085]

[Table 4]

[0086]

[Table 5]

[0087]

[Table 6]

[0088]

The use of a charge transport layer in which a specific polycarbonate resin and a specific distyryl compound are combined provides excellent coating properties, cleaning properties, abrasion resistance and durability, low fatigue in repeated use, and high sensitivity. A photoreceptor could be provided.

[0089]

────────────────────────────────────────────────── ─── Continuation of the front page Examiner Mina Asano (56) References JP-A-3-149560 (JP, A) JP-A-61-105550 (JP, A) JP-A-62-242951 (JP, A) JP-A-1-261652 (JP, A) JP-A-2-198451 (JP, A) JP-A-1-93746 (JP, A) (58) Fields studied (Int. Cl. ⁷ , DB name) G03G5 / 06 G03G 5/05 101

Claims (1)

(57) [Claims] 1. A laminated photoreceptor having a charge generation layer and a charge transport layer provided on a conductive support, wherein the charge generation layer comprises at least one distyryl compound represented by the following general formula (I): Formula 1 (In the formula, Ar ₁ and Ar ₂ each represent an alkyl group or an aryl group which may have a substituent. Ar ₃ each represents an alkyl group, an aralkyl group or an aryl group which may have a substituent. R ₁ and R ₂ are a hydrogen atom, an alkyl group, an alkoxy group or a halogen atom .R ₃ is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a thioether group, a phenoxy group, each location
Aryl groups, aralkyl groups,
It represents a xy group or a heterocyclic group. Provided that R ₃ is a substituent
And Except for an aryl group having A) A laminated photoconductor comprising at least one kind of polycarbonate resin represented by the following general formula as a binder resin. Embedded image _{(Wherein, R 4, R 5, R} 6, R 7, R 10, R 11, R 12 and R ₁₃ are each a hydrogen atom, an alkyl group, also an aryl group
It represents a halogen atom. R ₈ and R ₉ represent an alkyl group, a cyclic alkyl group or an aryl group which may have a substituent, and R ₈ and R ₉ may form a cyclic alkyl group which may have a substituent. Provided that R ₈ and R ₉ are both methyl
And R ₄ , R ₅ , R ₆ , R ₇ , R ₁₀ , R ₁₁ , R ₁₂ and R
Except when all ₁₃ are hydrogen atoms. And n and m are
Each shows a molar number of 10 to 1000. )