JP2943329B2 - 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 distyryl 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,
Distyryl compounds are disclosed in JP-A-60-175052 and JP-A-62-120346, but have a completely different chemical structure from the compounds disclosed in the present application.

An object of the present invention is to contain a distyryl compound having excellent compatibility with a binder and excellent charge transporting ability, high sensitivity, excellent charging ability, little fatigue deterioration when used repeatedly, and low electrophotographic characteristics. 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]

The present invention relates to a photosensitive member having a photosensitive layer containing a distyryl compound represented by the general formula [I] provided on a conductive support;

[0014]

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In the general formula [I], Ar ₁ represents a lower alkyl group such as a methyl group or an ethyl group; an aralkyl group such as a benzyl group; or an aryl group such as a phenyl group or a naphthyl group. It may have a substituent such as a group, a hydroxy group or a disubstituted amino group.

Ar ₂ and Ar ₃ each represent a hydrogen atom, a lower alkyl group such as a methyl group, an aralkyl group such as benzyl, an aryl group such as phenyl, or a heterocyclic group such as thiophene, furan or dioxaindane; May have an alkyl group, an alkoxy group, a hydroxy group, a disubstituted amino group, or a substituent such as halogen.

R ₁ and R ₃ each represent a hydrogen atom, an alkyl group such as a methyl group, an alkoxy group such as a methoxy group or an ethoxy group, or a halogen atom such as chlorine.

R ₂ represents an alkyl group such as a methyl group, an aralkyl group such as benzyl, or an aryl group such as a phenyl group, and each group may have a substituent. X represents an oxygen atom or a sulfur atom.

The distyryl compound represented by the general formula [I] of the present invention has a structural feature in that it is asymmetric with respect to a nitrogen atom, and has a photosensitivity such as compatibility with a resin, sensitivity, and repetition characteristics. Good results in body properties.

Preferred specific examples of the distyryl 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.

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

Embedded image [Wherein, Ar ₂ , Ar ₃ , and R _{1 to} R ₃ have the same meaning as in the general formula [I]. And the following general formula [III]: Ar ₁ -X-CH-Y [wherein, Ar ₁ and X have the same meanings as in general formula [I];
Represent trialkyl or triaryl represented by tetraalkylphosphonium group or PO dialkyl or diaryl phosphite group represented by (OR _{5) 2,} ^- it is -P ⁺ (R _{4) 3} Z
(Wherein Z is a halogen atom, and R ₄ and R ₅ are each an alkyl group or an aryl group)].

The compound represented by the general formula [I] is
It can also be synthesized by condensing the compounds represented by the general formulas [IV] and [V].

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

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 photoreceptor of the present invention has a photosensitive layer containing one or more distyryl compounds represented by the above general formula [I].

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 distyryl compound in a resin binder, or a charge-generating layer containing 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 distyryl compound of the present invention is a photoconductive substance, it acts as a charge transporting material and can transport charge carriers 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
It is preferably from 30 to 30 m, and more preferably from 5 to 20 m. 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 2 parts by weight, preferably 0.2 to 1.2 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 4 μm or less, preferably 2 μm or less, and the thickness of the charge transport layer is 3 to 30 μm, preferably 5 to 20 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. Another charge transporting material such as hydrazone may be used in combination with the distyryl 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 distyryl compound of the present invention are schematically shown in FIGS. FIG. 1 shows a charge generation material (3) and a charge transport material (2) on a substrate (1).
Is a photoreceptor having a photosensitive layer (4) formed by blending with a binder, and the distyryl compound of the present invention is used as a charge transport material.

FIG. 2 shows a charge generation layer (6) as a photosensitive layer.
And a function-separated type photoconductor having a charge transport layer (5),
The charge transport layer (5) is formed on the surface of the charge generation layer (6). The distyryl compound of the present invention is contained in the charge transport layer (5).

FIG. 3 shows the charge generation layer (6) as in FIG.
And a function-separated type photoreceptor having a charge transport layer (5). Contrary to FIG. 2, a charge generation layer is provided on the surface of the charge transport layer (5).
(6) is formed.

FIG. 4 shows that the surface protective layer (7) is further provided on the surface of the photoreceptor of FIG. 1. The photosensitive layer (4) comprises a charge generation layer (6) and a charge transport layer (5). ) May be used.

FIG. 5 shows that an intermediate layer (8) is provided between the substrate (1) and the photosensitive layer (4). It can be provided for protecting the substrate and improving 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.

Examples of the synthesis of the distyryl compound of the present invention are given below.
You.Synthesis Example 1 (Synthesis of Compound [1])  The following formula:

Embedded image 4.51 g of the aldehyde compound represented by the formula and 3.43 g of methoxymethyltriphenylphosphonium chloride
(0.01 mol) in 50 ml of dimethylformaldehyde
Under cooling in a nitrogen atmosphere, a suspension containing 1.68 g of potassium ter-butoxide was added dropwise to 50 ml of dimethylformamide. Then at room temperature
After stirring for an hour, the mixture was reacted at 80 ° C. for 2 hours to complete the reaction.

The obtained mixture was added to 500 ml of ice water and neutralized with dilute hydrochloric acid. After about 30 minutes, the precipitated crystals were filtered. Washing the filtered product with water, dissolving in toluene,
Separation and purification were performed by silica gel column chromatography. After distilling off toluene from the effluent, recrystallize from acetonitrile;
0 g of pale yellow crystals were obtained. From the mass spectrum of the product, M ⁺ = 479 peak was confirmed.

The results of the elemental analysis are as follows (C ₃₅
H ₂₉ NO).

[0053]Synthesis Example 2 (Synthesis of Compound [27])  The phosphorus compound used in Synthesis Example 1 was
2.61 g of nilthiomethylphosphonate (0.01 mol
The reaction was carried out in the same manner except that the compound was used in place of Profit
The mixture obtained was added to 500 ml of water, and neutralized with dilute hydrochloric acid.
Was. After about 30 minutes, the precipitated crystals were filtered. Filtration products
Is washed with water, dissolved in toluene, silica gel column
Separated and purified by chromatography. After distilling off the toluene in the effluent,
Recrystallization from ethanol gave 4.3 g of pale yellow crystals (yield
77.2%). From the mass spectrum of the product,
⁺= 557 was confirmed.

The elemental analysis values were as follows (C ₄₀ H)
₃₁ NS).

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

[0056]Example 1  The following general formula [A]:

Embedded image Was dispersed in a sand mill 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 (manufactured by Byron 200 Toyobo Co., Ltd.).
The obtained dispersion of the bisazo compound was applied on a 100 μm-thick aluminized mylar using a film applicator so that the dry film thickness became 0.3 g / m ^2, and then dried.

On the charge generation layer thus obtained, 50 parts of a distyryl compound [1] and 50 parts of a polycarbonate resin (Panlite K-1300; manufactured by Teijin Chemicals Ltd.) were dissolved in 400 parts of 1,4 dioxane. The solution was applied to a dry film thickness of 16 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-450Z: 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.

[0059]Examples 2 to 4  The same configuration as in the first embodiment,
Instead of the distyryl compound [1] used in Example 1, distyryl
A photoreceptor using each of the compounds [2], [3] and [4] was prepared.
Was. The photoconductor obtained in this manner is the same as in Example 1.
V in the way₀, E₁/_Two, DDR₁Was measured.

[0060]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)
It was dispersed by a sand mill together with 0 parts.

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, 50 parts of a distyryl compound [5] and a polyarylate resin
A solution prepared by dissolving 50 parts of U-100 (manufactured by Unitika) in 400 parts of 1,4-dioxane was applied to a dry film thickness of 20 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.

[0064]Examples 6 to 8  In the same manner as in Example 5, the same configuration
Distyryl was used in place of the distyryl compound [5] used in Example 5.
A photoreceptor using each of the compounds [6], [8] and [11] was prepared.
Was. The photoconductor obtained in this manner is the same as in Example 1.
V in the way₀, E₁/_Two, DDR₁Was measured.

[0065]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 the distyryl compound [12] and 50 parts of a polyarylate resin (U-100: manufactured by Unitika) in 400 parts of 1,4-dioxane was placed on the charge generation layer thus obtained. Is 18 μm
And dried 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.

[0067]Examples 10 to 11  The same configuration as that of the ninth embodiment,
Distyril instead of the distyryl compound [12] used in Example 9
Photoreceptors using each of the compounds [14] and [15]
Was. The photoconductor obtained in this manner is the same as in Example 1.
V in the way₀, E₁/_Two, DDR₁Was measured.

[0068]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 applied 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 prepared by dissolving 50 parts of a distyryl compound [24] and 50 parts of a polycarbonate resin (PC-Z: manufactured by Mitsubishi Gas Chemical Company) in 400 parts of 1,4 dioxane was dried on the charge generation layer thus obtained. 18μm thick
To form a charge transport layer.

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

[0071]Examples 13 and 14  The same configuration as in the twelfth embodiment,
Instead of the distyryl compound [24] used in Example 12,
Preparation of photoreceptors using tyryl compounds [26] and [27]
did. The photoreceptor thus obtained was the same as in Example 1.
V in a similar way₀, E₁/_Two, DDR₁Was measured.

[0072]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 distyryl compound [28] 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 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.

[0075]Examples 16 to 17  The same configuration as in the fifteenth embodiment, except that
Instead of the distyryl compound [28] used in Example 15,
Preparation of photoreceptors using tyryl compounds [29] and [30]
did. The photoreceptor thus obtained was the same as in Example 1.
V in a similar way₀, E₁/_Two, DDR₁Was measured.

[0076]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 were mixed with 22.5 parts of a thermosetting acrylic resin (Acrydic A405: manufactured by Dainippon Ink) and melamine resin (Super Beckamine J820: manufactured by Dainippon Ink) 7 .5 parts and 15 parts of the above-mentioned distyryl compound [31] were put into 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.

[0078] 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.

[0079]Examples 19 to 21  The same configuration as in Example 18 but having the same configuration
Instead of the distyryl compound [31] used in Example 18,
Photosensitivity using tyryl compounds [32], [34], [36]
The body was made. The photoconductor obtained in this way was implemented
In the same manner as in Example 1, V₀, E₁/_Two, DDR₁Was measured.

[0080]Comparative Examples 1-4  The same configuration as in Example 18 but having the same configuration
Instead of the distyryl 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.

[0081]

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[0082] Thus the obtained photoreceptor was measured _{V 0, E 1/2,} DDR 1 in the same manner as in Example 1.
In addition, since the compounds of [E] and [G] had poor solubility, some crystals precipitated during the preparation of the photoreceptor.

[0083]Comparative Examples 5 to 7  The same configuration as in Example 18 but having the same configuration
Instead of the distyryl compound [31] used in Example 18,
Except that each of the distyryl compounds [I], [J], [K] is used
A photoreceptor was manufactured in exactly the same manner as in Example 18.

[0084]

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[0085] 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 [I] and [K] had poor solubility, some crystals precipitated during the preparation of the photoreceptor.

[0086] Examples 1-21, Comparative Example V ₀ which obtained photoreceptor 1 to 7, E _1/2, Tables 1 2 The measurement results of the DDR ₁
Are shown together.

[0087]

[Table 1]

[0088]

[Table 2]

As can be seen from Table 1, the photoreceptor of the present invention has a sufficient charge retention ability, whether it is a laminated type or a single layer type, and has a dark decay rate small enough to be usable 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 18 at the time of positive charging using a commercially available electrophotographic copying machine (EP-350Z manufactured by Minolta Camera Co., Ltd.).
Even when 1000 copies are made, the initial and final images have excellent gradation, no change in sensitivity, a clear image can be obtained, and the photoreceptor of the present invention has stable repetition characteristics.

[0091]

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.

[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 (72) Inventor Keiichi Inagaki 2-3-13 Azuchicho, Chuo-ku, Osaka-shi, Osaka Osaka International Building Minolta Camera Co., Ltd. In-house (56) References JP-A-62-120346 (JP, A) JP-A-1-93746 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) G03G 5/06 313 G03G 5/06 319 CA (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] 1. A photoreceptor having a photosensitive layer containing a distyryl compound represented by the following general formula [I] on a conductive support: [Wherein, Ar ₁ represents an alkyl group, an aralkyl group, or an aryl group, each of which may have a substituent; Ar
₂ and Ar ₃ each represent a hydrogen atom, an optionally substituted alkyl group, an aralkyl group, an aryl group or a heterocyclic group; R ₁ and R ₃ each represent a hydrogen atom, an alkyl group, an alkoxy group or Represents a halogen atom; R ₂
Represents an alkyl group, an aralkyl group or an aryl group,
X may have a substituent; X represents an oxygen atom or a sulfur atom. ]