JP3097159B2 - Photoconductor - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photoreceptor having a photosensitive layer containing a novel styryl compound.

[0002]

2. Description of the Related Art In general, in electrophotography, an electrostatic latent image is formed by charging and exposing the surface of a photosensitive layer of a photoreceptor, and developing the latent image with a developer to visualize the latent image. A direct method of fixing a photoreceptor to obtain a copy image, a powder image transfer method of transferring a visible image on a photoreceptor onto a transfer material such as paper, and fixing the transferred image to obtain a copy image, or a photosensitive method. 2. Related Art A latent image transfer method of transferring an electrostatic latent image on a body onto transfer paper, and developing and fixing the electrostatic latent image on the transfer paper is known.

As a material constituting a photosensitive layer of a photosensitive member used in this type of electrophotography, inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide have been conventionally known.

[0004] These photoconductive materials have many advantages, such as little charge dissipation in a dark place, or the ability to quickly dissipate charge by light irradiation, but have various disadvantages. I have. For example, in the case of a selenium-based photoconductor, manufacturing conditions are difficult, manufacturing costs are high,
In addition, care is required for handling because it is susceptible to heat and mechanical shock. Cadmium sulfide photoreceptors and zinc oxide photoreceptors do not provide stable sensitivity in humid environments, and dyes added as sensitizers cause charge deterioration due to corona charging and photobleaching due to exposure, resulting in long-term However, there is a disadvantage that stable characteristics cannot be provided over a wide range.

On the other hand, various organic photoconductive polymers such as polyvinyl carbazole have been proposed.
These polymers are superior to the above-mentioned inorganic photoconductive materials in terms of film-forming properties and lightness, but still have sufficient sensitivity, durability and stability due to environmental changes. Inferior to conductive materials.

[0006] Further, the low molecular weight organic photoconductive compound can be obtained by selecting the kind and composition ratio of the binder used together.
Although it is preferable in that the physical properties or electrophotographic properties of the coating can be controlled, high compatibility with the binder is required because it is used together with the binder.

A photoreceptor in which these high and low molecular weight organic photoconductive compounds are dispersed in a binder resin has drawbacks such as a large residual potential due to many carrier traps and low sensitivity. Therefore, it has been proposed to solve the above-mentioned drawbacks by blending a charge transport material with a photoconductive compound.

Further, a function-separated type photoreceptor has been proposed in which the charge generation function and the charge transport function of the photoconductive function are shared by different substances. In such a function-separated type photoreceptor, many organic compounds are listed as the charge transporting material used for the charge transporting layer, but there are various problems in practice. For example, U.S. Pat.
2,5-bis (P-diethylaminophenyl) 1,3,4-oxadiazole described in Japanese Patent No. 9,447 has low compatibility with a binder and tends to precipitate crystals. The diarylalkane derivative described in U.S. Pat. No. 3,820,989 has good compatibility with a binder, but changes in sensitivity when used repeatedly. Further, the hizolazone compound described in JP-A-54-59143 has a relatively good residual potential property, but has a drawback of poor charging ability and repetition property.

As described above, there is almost no low-molecular-weight organic compound having practically preferable characteristics in producing a photoreceptor.

As a compound having excellent charge transporting ability,
A styryl compound is disclosed in JP-A-58-90953, but has a completely different chemical structure from the compound disclosed in the present application.

An object of the present invention is to contain a styryl compound having excellent compatibility with a binder and excellent charge transport ability, high sensitivity, excellent charge ability, little fatigue deterioration when used repeatedly, and low electrophotographic properties. An object is to provide a stable photoconductor.

[0012]

SUMMARY OF THE INVENTION The present invention has been made in view of the above facts, and it is an object of the present invention to provide a photoreceptor excellent in overall electrostatic characteristics and particularly excellent in sensitivity. .

[0013]

SUMMARY OF THE INVENTION The present invention relates to a photoreceptor in which a photosensitive layer containing a styryl compound represented by the general formula [I] is provided on a conductive support;

[0014]

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The distyryl compound represented by the general formula [I] of the present invention has a structural feature of having a trifluoromethyl group, and has compatibility with a resin (binder resin), sensitivity, repetition characteristics and the like. Good results on photoreceptor properties. In the general formula [I], R ₁ represents a hydrogen atom, an alkyl group such as a methyl group, an ethyl group or propyl, a hydroxyl group, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, or a trifluoromethyl group. Represent.

R ₂ represents a hydrogen atom, an alkyl group such as a methyl group, an ethyl group or a propyl group, or an aryl group such as phenyl. The aryl group may have a substituent such as a disubstituted amino group.

Ar ₁ represents an arylene group such as a phenylene group or a naphthylene group. Ar ₁ may have an alkyl group such as a methyl group and an ethyl group.

Ar ₂ and Ar ₃ are an alkyl group such as a methyl group, an ethyl group or a propyl group, an aralkyl group such as a benzyl group or a phenethyl group, an aryl group such as a phenyl group or a biphenyl group or a heterocyclic group; For example, it represents a thienyl group or a furyl group, and Ar ₂ and Ar ₃ may be combined to form a ring. n represents an integer of 0 or 1

Preferred specific examples of the styryl compound represented by the general formula [I] of the present invention include, for example, those having the following structural formulas, but are not limited thereto.

[0020]

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[0021]

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[0022]

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[0023]

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[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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The compound represented by the general formula [I] of the present invention is
It can be easily synthesized by an ordinary method. That is, a carbonyl compound represented by the general formula [II]:

Embedded image [Wherein, R ₂ , Ar ₁ , Ar ₂ and Ar ₃ have the same meaning as in the general formula [I]. And the following general formula [III]:

Embedded image Wherein R ₁ has the same meaning as in general formula [I]; X is -P ⁺
(R _{3) 3} Y ^- trialkyl or triaryl represented by tetraalkylphosphonium group or PO (OR ₄₎ represents a dialkyl or diaryl phosphite group represented by ₂ (wherein Y is a halogen atom,, R _3, R ₄ Can be synthesized by condensing a phosphorus compound represented by an alkyl group or an aryl group)].

As the reaction solvent in the above method, for example, hydrocarbons, alcohols and ethers are preferable, and methanol, ethanol, isopropanol, butanol,
2-methoxyethanol, 1,2-dimethoxyethane,
Bis (2-methoxyethyl) ether, dioxane, tetrahydrofuran, toluene, xylene dimethyl sulfoxide, N, N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, and the like. Among them, polar solvents such as N, N-dimethylformamide and dimethylsulfoxide are preferred. Examples of condensing agents include sodium hydroxide, potassium hydroxide, sodium amide, sodium hydrogen and sodium methylate,
An alcoholate such as potassium ter-butoxide is used. The reaction temperature can be selected in a wide range from about 0 ° C to about 100 ° C. Preferably it is from 10C to about 80C. The compound [III] used in the present invention uses a corresponding quaternary phosphonium salt, for example, a triphenylphosphonium salt, instead of a phosphorus compound, and undergoes a phosphorylene step by the method of Wittig to give an aldehyde compound [ [II] to synthesize the styryl compound [I].

The photoreceptor of the present invention has a photosensitive layer containing one or more styryl compounds represented by the general formula [I]. In addition, as long as the effect of the present invention is not impaired, it may be used by mixing with a charge transport material such as a hydrazone compound.

Although various types of photoconductors are known, the photoconductor of the present invention may be any of those photoconductors. For example, a charge-generating material on a support, a single-layer photoreceptor having a photosensitive layer formed by dispersing a styryl compound in a resin binder, or a charge-generating layer having a charge-generating material as a main component on a support, There is a so-called laminated photoconductor provided with a charge transport layer thereon. Although the styryl compound of the present invention is a photoconductive substance, it acts as a charge transporting material and can transport a charge carrier generated by absorbing light extremely efficiently.

In order to prepare a single-layer type photoreceptor, fine particles of a charge generating material are dispersed in a resin solution or a solution in which a charge transport compound and a resin are dissolved, and this is coated on a conductive support and dried. I just need. At this time, the thickness of the photosensitive layer is 3
４０40 μm, preferably 5-30 μm. If the amount of the charge generating material used is too small, the sensitivity is poor, and if it is too large, the chargeability is deteriorated, the mechanical strength of the photosensitive layer is reduced, and the proportion in the photosensitive layer is 1 part by weight of the resin. The range is 0.01 to 3 parts by weight, preferably 0.2 to 2 parts by weight.

In order to produce a laminated photoreceptor, a charge generation material is vacuum-deposited on a conductive support, or dissolved in a solvent such as an amine, and applied. After coating and drying the coating solution prepared by dispersing in the solution in which the binder resin is dissolved if any,
A solution containing a charge transporting material and a binder is coated thereon and dried. In the case of performing vacuum deposition, for example, phthalocyanines such as metal-free phthalocyanine, titanyl phthalocyanine, and aluminum chlorophthalocyanine are used. When dispersing, for example, a bisazo pigment is used. At this time, the thickness of the charge generation layer is preferably 4 μm or less, preferably 2 μm or less, and the thickness of the charge transport layer is preferably 3 to 40 μm, and more preferably 5 to 30 μm.

The proportion of the charge transporting material in the charge transporting layer is 0.2 to 2 parts by weight, preferably 0.3 to 1.3 parts by weight, per 1 part by weight of the binder resin.

The photoreceptor of the present invention comprises, together with a binder resin, a plasticizer such as halogenated paraffin, polychlorinated biphenyl, dimethylnaphthalene, dibutylphthalate, O-terphenyl, chloranil, tetracyanoethylene,
Electron-withdrawing sensitizers such as 2,4,7-trinitrofluorenone, 5,6-dicyanobenzoquinone, tetracyanoquinodimethane, tetrachlorophthalic anhydride, 3,5-dinitrobenzoic acid, methyl violet, rhodamine B; Sensitizers such as cyanine dyes, pyrylium salts and thiapyrylium salts may be used. Also, antioxidants and ultraviolet absorbers,
Dispersing aids, anti-settling agents, leveling agents and the like may also be used as appropriate. Other charge transport materials such as hydrazone may be used in combination with the styryl compound of the present invention.

The electrically insulating binder resin used in the present invention may be a known electrically insulating thermoplastic resin or a binder such as a thermosetting resin, a photocurable resin or a photoconductive resin. Can be used. Examples of suitable binder resins include, but are not limited to, saturated polyester resins, polyamide resins, acrylic resins, ethylene-vinyl acetate resins, ionically crosslinked olefin copolymers.
(Ionomer), styrene-butadiene block copolymer, polycarbonate, vinyl chloride-vinyl acetate copolymer, cellulose ester, polyimide, thermoplastic resin such as styrene resin; epoxy resin, urethane resin, silicone resin, phenol resin, melamine resin Thermosetting resins such as xylene resins, alkyd resins, and thermosetting acrylic resins; photocurable resins; and photoconductive resins such as polyvinylcarbazole, polyvinylpyrene, polyvinylanthracene, and polyvinylpyrrole. These can be used alone or in combination. It is desirable that these electrically insulating resins have a volume resistance of 1 × 10 ¹² Ω · cm or more when measured alone.

As the charge generating material, bisazo pigments,
Triarylmethane dyes, thiazine dyes, oxazine dyes, xanthene dyes, cyanine dyes, styryl dyes, pyrylium dyes, azo pigments, quinacridone pigments, indigo pigments, perylene pigments, polycyclic quinones Organic substances such as pigments, bisbenzimidazole pigments, indathrone pigments, squarium salt pigments, azulene pigments, phthalocyanine pigments, selenium, selenium,
Inorganic substances such as tellurium, selenium alloys such as selenium and arsenic, cadmium sulfide, cadmium selenide, zinc oxide, amorphous silicon, and the like. In addition, any material that absorbs light and generates charge carriers at an extremely high probability can be used.

As the conductive support used in the photoreceptor of the present invention, a sheet or drum made of a metal foil or plate of copper, aluminum, silver, iron, nickel or the like is used. Metal is vacuum-deposited or electroless-plated on a plastic film or the like, or a layer of a conductive compound such as a conductive polymer, indium oxide or tin oxide is similarly applied or deposited on a support such as paper or a plastic film. The one used is used.

Examples of the constitution of a photoreceptor using the styryl compound of the present invention are schematically shown in FIGS. FIG. 1 shows a photoconductor in which a photosensitive layer (4) in which a charge generation material (3) and a charge transport material (2) are mixed with a binder is formed on a substrate (1). Are used.

FIG. 2 shows a charge generation layer (6) as a photosensitive layer,
A function-separated type photoreceptor having a charge transport layer (5), wherein a charge transport layer (5) is formed on the surface of a charge generation layer (6).
The charge transport layer (5) contains the styryl compound of the present invention.

FIG. 3 shows a charge generation layer (6) similar to FIG.
The function-separated type photoreceptor having the charge transport layer (5) has a charge generation layer (6) formed on the surface of the charge transport layer (5), contrary to FIG.

FIG. 4 shows that the surface of the photoreceptor shown in FIG. 1 is further provided with a surface protective layer (7). The photosensitive layer (4) comprises a charge generation layer (6) and a charge transport layer (5). A function-separated type photoconductor may be used.

FIG. 5 shows a structure in which an intermediate layer (8) is provided between the substrate (1) and the photosensitive layer (4). In order to protect the photosensitive layer and to improve the charge injection property from the substrate to the photosensitive layer.

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 desirably 1 μm or less.

As a material used for the surface protective layer, a polymer such as an acrylic resin, a polyaryl resin, a polycarbonate resin, or a urethane resin as it is, or a material in which a low-resistance compound such as tin oxide or indium oxide is dispersed is suitable. is there. Also, an organic plasma polymerized film can be used. The organic plasma polymerized film may optionally contain oxygen, nitrogen, halogen, and atoms of Groups 3 and 5 of the Periodic Table as appropriate. The thickness of the surface protective layer is 5 μm.
m or less is desirable.

[0050]

[Synthesis Example] A synthesis example of the styryl compound of the present invention will be described. Synthesis Example 1 (Synthesis of Compound [3])

Embedded image 2.96 g of a phosphonate compound represented by the following formula:

Embedded image Was dissolved in 30 ml of dimethylformamide, and a suspension containing 5 g of potassium ter-butoxide was dropped into 70 ml of dimethylformamide while cooling to 5 ° C. Then, after stirring at room temperature for 8 hours, the mixture was left overnight. The obtained mixture is added to ice water 500
The resulting mixture was neutralized with dilute hydrochloric acid, and after about 30 minutes, the precipitated crystals were filtered. The filtered product was washed with water and further purified by recrystallization from acetonitrile to obtain yellow needle crystals 3.7.
g was obtained. The melting point was 77-78 ⁰ C. 86 yield
%Met.

The results of the elemental analysis are as follows (C ₂₈
As H ₂₂ NF _3). FIG. 6 shows the infrared absorption spectrum of the obtained compound.

Synthesis Example 2 (Synthesis of Compound [23]) In the same manner as in Synthesis Example 1, except that

Embedded image Was synthesized using 2.96 g of the phosphonate compound represented by the formula, and after the reaction, the resulting mixture was added to 500 ml of ice water, neutralized with dilute hydrochloric acid, and crystals precipitated after about 30 minutes were filtered. The obtained crystals were dissolved in toluene, separated by silica gel column chromatography (developing solvent, toluene), the solvent was distilled off, and the obtained separated product was purified by recrystallization using an acetonitrile-ethanol mixed solvent to give a yellow-white needle. 3.5 g of crystalline crystals were obtained. Melting point was 88-90 ° C. The yield was 80%.

The results of the elemental analysis are as follows (C ₂₈
As H ₂₂ NF _3). FIG. 7 shows the infrared absorption spectrum of the obtained compound.

[0054]

Hereinafter, the present invention will be described with reference to examples.
In the examples, “parts” means “parts by weight” unless otherwise specified.

[0055]Example 1  The following general formula [A]:

Embedded image Was dispersed with a sand grinder together with 50 parts of cyclohexanone together with 0.45 parts of a bisazo compound represented by the following formula and 0.45 parts of a polyester resin (Vylon 200; manufactured by Toyobo Co., Ltd.). The resulting dispersion of the bisazo compound was applied to a thickness of 10
Using a film applicator, the film was coated on a 0 μm aluminized mylar using a film applicator so as to have a dry film thickness of 0.3 g / m ^2, and then dried.

On the charge generation layer thus obtained, 70 parts of styryl compound [3] and polycarbonate resin
(Panlite K-1300; manufactured by Teijin Chemicals Limited)
A solution dissolved in 400 parts of 4-dioxane has a dry film thickness of 1
It was applied to a thickness of 6 μm and dried to form a charge transport layer. Thus, an electrophotographic photoreceptor having two photosensitive layers was obtained.

The photoreceptor thus obtained was subjected to a commercially available electrophotographic copying machine (EP-470Z: manufactured by Minolta Camera Co., Ltd.).
Was corona charged at -6 kV, the initial surface potential V ₀ (v), the exposure amount required to initial potential to the _{1/2 E 1/2 (lux ·} se
c) Decay rate DD of initial potential when left in the dark for 1 second
R ₁ (%) was measured.

[0058]Examples 2 to 4  The same configuration as in the first embodiment,
Styryl compound in place of styryl compound [3] used in Example 1
A photoreceptor using each of the products [4], [6], and [7] was produced. This
The obtained photoreceptor was treated in the same manner as in Example 1.
And V₀, E₁/_Two, DDR₁Was measured.

[0059]Example 5  The following general formula [B]:

Embedded image 0.45 parts of a bisazo compound represented by the formula and 0.45 parts of a polystyrene resin (molecular weight: 40,000)
The mixture was dispersed together with 0 parts by a sand grinder.

The obtained dispersion of the bisazo compound was applied to a thickness of 1
The film was applied on a 00 μm aluminized mylar using a film applicator to a dry film thickness of 0.3 g / m ² and then dried.

On the charge generation layer thus obtained, 70 parts of styryl compound [8] and polyarylate resin
A solution prepared by dissolving 70 parts (U-100: manufactured by Unitika) in 400 parts of 1,4 dioxane was applied to a dry film thickness of 16 μm, and dried to form a charge transport layer.

Thus, an electrophotographic photosensitive member having a two-layer photosensitive layer was manufactured. The thus obtained photosensitive member, V ₀ in the same manner as in Example _1, E _1/2, D
It was measured DR _1.

[0063]Examples 6 to 8  In the same manner as in Example 5, the same configuration
Styryl compound in place of styryl compound [8] used in Example 5
Photoreceptors using each of the products [13], [14], and [16]
Was. The photoconductor obtained in this manner is the same as in Example 1.
V in the way₀, E₁/_Two, DDR₁Was measured.

[0064]Example 9  The following general formula [C]:

Embedded image 0.45 parts of a polycyclic quinone pigment represented by the formula: 0.4, polycarbonate resin (Panlite K-1300: manufactured by Teijin Chemicals Ltd.)
5 parts were dispersed together with 50 parts of dichloroethane by a sand mill. The resulting dispersion of the polycyclic quinone pigment was applied on an aluminized mylar having a thickness of 100 μm using a film applicator so that the dry film thickness was 0.4 g / m ^2, and then dried. A solution prepared by dissolving 60 parts of a styryl compound [17] and 50 parts of a polyarylate resin (U-100: manufactured by Unitika) in 400 parts of 1,4-dioxane was obtained on the charge generation layer thus obtained. Was applied to be 18 μm and dried to form a charge transport layer.

In this way, an electrophotographic photosensitive member having a two-layer photosensitive layer was manufactured. The thus obtained photosensitive member, V ₀ in the same manner as in Example _1, E _1/2, D
It was measured DR _1.

[0066]Examples 10 to 11  The same configuration as that of the ninth embodiment,
Styrylation instead of styryl compound [17] used in Example 9
Photoconductors using Compounds [18] and [21] were prepared. This
The obtained photoreceptor was treated in the same manner as in Example 1.
And V₀, E₁/_Two, DDR₁Was measured.

[0067]Example 12  The following general formula [D]:

Embedded image 0.45 parts of a perylene pigment represented by the formula, butyral resin
0.45 parts (BX-1: manufactured by Sekisui Chemical Co., Ltd.) were dispersed together with 50 parts of dichloroethane by a sand mill.

The resulting dispersion of the perylene pigment was coated to a thickness of 1
Using a film applicator, the film was applied on a 00 μm aluminized mylar using a film applicator so as to have a dry film thickness of 0.4 g / m ^2, and then dried. A solution obtained by dissolving 50 parts of a styryl compound [22] and 50 parts of a polycarbonate resin (PC-Z: manufactured by Mitsubishi Gas Chemical Co., Ltd.) in 400 parts of 1,4-dioxane was placed on the thus obtained charge generating layer. Coating was performed so that the thickness became 18 μm to form a charge transport layer.

Thus, an electrophotographic photosensitive member having a two-layer photosensitive layer was produced. The thus obtained photosensitive member, V ₀ in the same manner as in Example _1, E _1/2, D
It was measured DR _1.

[0070]Examples 13 and 14  The same configuration as in the twelfth embodiment,
Instead of the styryl compound [22] used in Example 12,
Photoreceptors using each of the compounds [23] and [24]
Was. The photoconductor obtained in this manner is the same as in Example 1.
V in the way₀, E₁/_Two, DDR₁Was measured.

[0071]Example 15  0.45 part of titanyl phthalocyanine, butyral resin
(BX-1: Sekisui Chemical Co., Ltd.) 0.45 parts of dichloroeta
Together with 50 parts of the mixture by a sand mill. Obtained
100 μm thick phthalocyanine pigment dispersion
Dry using a film applicator on
0.3 g / m dry film thickness^TwoAnd then dry it.
Was.

A solution prepared by dissolving 50 parts of a styryl compound [25] and 50 parts of a polycarbonate resin (PC-Z: manufactured by Mitsubishi Gas Chemical Co., Ltd.) in 400 parts of 1,4-dioxane on the charge generation layer thus obtained. Was applied to a dry film thickness of 18 μm to form a charge transport layer.

Thus, an electrophotographic photosensitive member having two photosensitive layers was produced. The thus obtained photosensitive member, V ₀ in the same manner as in Example _1, E _1/2, D
It was measured DR _1.

[0074]Examples 16 to 17  The same configuration as in the fifteenth embodiment, except that
In place of the styryl compound [25] used in Example 15,
Photoreceptors using the compounds [26] and [27]
Was. The photoconductor obtained in this manner is the same as in Example 1.
V in the way₀, E₁/_Two, DDR₁Was measured.

[0075]Example 18  Copper phthalocyanine 50 parts and tetranitro copper phthalocyanine
While stirring 0.2 part of nin into 500 parts of 98% concentrated sulfuric acid,
5,000 parts of water, and dissolve in copper phthalocyanine.
Photoconductive material group of nin and tetranitro copper phthalocyanine
After precipitating the product, it is filtered, washed with water, and at 120 ° C. under reduced pressure.
Dried.

10 parts of the photoconductive composition thus obtained was mixed with 22.5 parts of a thermosetting acrylic resin (Acrydick A405: manufactured by Dainippon Ink) and melamine resin (Super Beckamine J820: manufactured by Dainippon Ink) 7 .5 parts and 15 parts of the aforementioned styryl compound [28] were placed in a ball mill pot together with 100 parts of a mixed solvent obtained by mixing methyl ethyl ketone and xylene in the same amount, and dispersed for 48 hours to prepare a photosensitive coating solution. Was coated on an aluminum substrate and dried to form a photosensitive layer having a thickness of about 15 μm, thereby producing a photosensitive member.

[0077] Thus the obtained photoreceptors, the same method as that in Example 1 except that measured _{V 0, E 1/2,} DDR 1 and subjected to corona charging at + 6kV.

[0078]Examples 19 to 21  The same configuration as in Example 18 but having the same configuration
In place of the styryl compound [28] used in Example 18,
Photoreceptors using compounds [37], [47] and [50]
Produced. Example 1 of the photoreceptor thus obtained was used.
V in the same way as₀, E₁/_Two, DDR₁Was measured.

[0079]Comparative Examples 1-4  The same configuration as in Example 18 but having the same configuration
Instead of the styryl compound used in Example 18, the following compound
Example 15 except that [E], [F], [G], and [H] were used.
A photoreceptor was produced in exactly the same manner as described above.

[0080]

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[0081] Thus the obtained photoreceptor was measured _{V 0, E 1/2,} DDR 1 in the same manner as in Example 1.

[0082]Comparative Examples 5 to 8  The same configuration as in Example 18 but having the same configuration
Instead of the styryl compound [28] used in Example 18,
Using the tyryl compounds [I], [J], [K] and [L] respectively
A photoconductor was prepared in exactly the same manner as in Example 18 except that
Was.

[0083]

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[0084] Thus the obtained photoreceptor was measured _{V 0, E 1/2,} DDR 1 in the same manner as in Example 15.
In addition, since the compounds of [E], [G], [J] and [L] had poor solubility, some crystals were precipitated during the preparation of the photoreceptor.

[0085] shows an embodiment 1 to 21, V ₀ of the resulting photosensitive member in Comparative Example 1 to 8, E _1/2, the measurement results of the DDR ₁ are summarized in Tables 1 and to Table 2.

[0086]

[Table 1]

[0087]

[Table 2]

As can be seen from Tables 1 and 2, the photoreceptor of the present invention has a sufficient charge retention ability even in a laminated type or a single-layer type, and the dark decay rate is small enough to be used as a photoreceptor. It is clear from the data that the sensitivity is excellent.

Further, a repetitive real-photographing test was performed on a photosensitive member of Example 9 with a commercially available electrophotographic copying machine (EP-350Z manufactured by Minolta Camera Co., Ltd.) at the time of positive charging.
Even when 000 copies are made, the initial and final images have excellent gradation, no change in sensitivity, a clear image can be obtained, and it can be seen that the photoreceptor of the present invention has stable repetition characteristics. Next, the photoreceptors obtained in Example 18 and Comparative Example 7 were left in an ozone atmosphere having an ozone concentration of 20 ppm for 3 hours. Provided a clear image equivalent to that of the initial stage, but the photoreceptor obtained in Comparative Example 7 had poor image-like thin line reproducibility, lacked sharpness, and exhibited uneven density. This also photoreceptor of the present invention, the image stability is good and it can be seen that it is possible to maintain good characteristics for oxidizing gases such as ozone and NO _x.

[0090]

The present invention has provided a photoconductive compound useful for a photoreceptor. The photoconductive compound of the present invention is a styryl compound, and is particularly useful as a charge transport material. The photoreceptor having the styryl compound of the present invention has sensitivity, charge transportability,
Excellent photoreceptor characteristics such as initial surface potential and dark decay rate, and less light fatigue due to repeated use.

[Brief description of the drawings]

FIG. 1 is a schematic view of a dispersion type photoconductor in which a photoconductive layer is laminated on a conductive support.

FIG. 2 is a schematic view of a function-separated type photoconductor in which a charge generation layer and a charge transport layer are laminated on a conductive support.

FIG. 3 is a schematic view of a function-separated type photoconductor in which a charge transport layer and a charge generation layer are laminated on a conductive support.

FIG. 4 is a schematic diagram of a photosensitive member having a photosensitive layer and a surface protective layer formed on a conductive support.

FIG. 5 is a schematic diagram of a photosensitive member having an intermediate layer and a photosensitive layer formed on a conductive support.

FIG. 6 is a view showing an infrared absorption spectrum of a compound example of the present invention.

FIG. 7 is a view showing an infrared absorption spectrum of a compound example of the present invention.

[Explanation of symbols]

 REFERENCE SIGNS LIST 1 conductive support 2 charge transport material 3 charge generation material 4 photosensitive layer 5 charge transport layer 6 charge generation layer 7 surface protection layer 8 intermediate layer

──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-4-330449 (JP, A) JP-A-4-330451 (JP, A) JP-A-59-191060 (JP, A) JP-A-63-1988 27848 (JP, A) JP-A-1-310904 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G03G 5/06

Claims (1)

(57) [Claims] 1. A photoreceptor having a photosensitive layer containing a styryl compound represented by the following general formula [I] on a conductive support: [Wherein, R ₁ represents a hydrogen atom, an alkyl group, a hydroxyl group, a halogen atom or a trifluoromethyl group; R ₂ is a hydrogen atom, which may have an alkyl group or a substituted group represents an aryl group; Ar ₁ is it may have a substituent represents an arylene group; Ar ₂ and Ar ₃ each may have a substituent, an alkyl group, an aralkyl group, an aryl group or a heterocyclic group, Ar _2, Ar ₃ may form a ring together; n represents an integer of 0 or 1 ;
N is 0, R ₁ and R ₂ are hydrogen atoms, Ar ₁ is phenyl
Even if Ar ₂ and Ar ₃ have a substituent
When a phenyl group, any one of Ar _2, Ar ₃
One of the substituents is Unless it is ).