JPH1020526A - Electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an electrophotographic photoreceptor excellent in durability without deteriorating electrophotographic characteristics such as sensitivity, potential by electrification and residual potential by forming a photosensitive layer contg. a specified amine compd. and a specified UV absorber on an electrically conductive substrate. SOLUTION: This electrophotographic photoreceptor has a photosensitive layer contg. a monovalent group represented by formula I or II or an amine compd. represented by formula III, one or more kinds of compds. selected from among a benzotriazole compd., a benzoate compd., etc., as a UV absorber and one or more kinds of hindered amine compds. as a light stabilizer on the electrically conductive substrate. In the formulae I-III, Ar1 is optionally substd. aryl, Ar2 is optionally substd. phenylene, etc., each of R1 and R2 is lower alkyl, etc., R3 is halogen, etc., L is H, etc., M is optionally substd. aryl, and each of (m) and (n) is an integer of 0-4.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor, and more particularly, to an electrophotographic photoreceptor in which deterioration of electrophotographic characteristics caused by light fatigue is prevented.

[0002]

2. Description of the Related Art Conventionally, selenium,
Inorganic photoconductive materials such as zinc oxide, cadmium sulfide, and silicon have been widely used. While these inorganic materials have many advantages, they also have various disadvantages. For example, selenium has the drawback that it is difficult to manufacture and is easily crystallized by heat and mechanical shock.Zinc oxide and cadmium sulfide have problems with moisture resistance and mechanical strength, and are charged by a dye added as a sensitizer. And exposure deterioration, and lacks durability. Silicon is also difficult to manufacture and uses highly irritating gas, so it is expensive and sensitive to humidity, so care must be taken during handling. In addition, selenium and cadmium sulfide have toxicity problems.

In recent years, organic photoreceptors using various organic compounds have been studied for the purpose of overcoming the disadvantages of these inorganic photoreceptors, and have been widely used. Organic photoreceptors include a single-layer photoreceptor in which a charge generating agent and a charge transporting agent are dispersed in a binder resin, and a laminated photoreceptor in which functions are separated into a charge generating layer and a charge transporting layer. The feature of such a photoreceptor, which is called a function-separated type, is that a material suitable for each function can be selected from a wide range. Has been advanced.

As described above, various improvements such as the development of new materials and their combinations have been made in order to satisfy the basic performance and high durability requirements for electrophotographic photoreceptors. However, when used repeatedly, the residual potential is increased due to accumulation of traps in the charge transport layer.

One of the causes is that the charge transporting agent contained in the charge transporting layer undergoes an irreversible chemical change in the vicinity of the surface due to the action of ultraviolet light, becomes a component for trapping charges, and the residual potential gradually increases when used repeatedly. It is presumed that it will continue.

[0006]

SUMMARY OF THE INVENTION The present inventors have studied in detail the deterioration of a photoreceptor using a specific amine compound, and as a result, selectively absorb ultraviolet rays which are harmful to the photoreceptor. It has been found that certain compounds can be effectively prevented. An object of the present invention is to provide an electrophotographic photoreceptor having excellent repetition stability without impairing electrophotographic properties such as sensitivity, charging potential and residual potential by using and combining these specific compounds. It is in.

[0007]

According to the present invention, the following general formula [1] is provided on a conductive support.

[0008]

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[In the formula, Ar ₁ represents a substituted or unsubstituted aryl group; Ar ₂ represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted biphenylene group; Represents an unsubstituted anthrylene group, R ₁ represents a hydrogen atom, a lower alkyl group or a lower alkoxy group, L represents a hydrogen atom,
Represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and M is a substituted or unsubstituted aryl group, represented by the following general formula [2]

[0010]

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(Wherein, R ₁ has the same meaning as described above.)
Or a monovalent group represented by the following general formula [3]

[0012]

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(Wherein, R ₂ represents a hydrogen atom, a lower alkyl group or a lower alkoxy group, R ₃ represents a hydrogen atom, a halogen atom or a lower alkyl group, and N represents a hydrogen atom, a substituted or unsubstituted aryl group. M and n represent an integer of 0 to 4). A photosensitive layer containing an amine compound represented by the following formula: 1 selected from the group of system compounds
An electrophotographic photoconductor comprising at least one compound and at least one compound selected from the group of hindered amine compounds as a light stabilizer.

Further, as an ultraviolet absorber, a benzotriazole compound represented by the following general formula [4]:

[0015]

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[Wherein R_FourIs hydrogen atom, lower alkyl group
Or a halogen atom;_FiveAnd R ₆ Are each independently water
An atom, an alkyl group or a substituted or unsubstituted aral
Represents a kill group. ]

A benzoate compound represented by the following general formula [5]:

[0018]

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Wherein X and Y represent a hydrogen atom or a hydroxyl group, provided that X and Y are not a hydrogen atom or a hydroxyl group at the same time, and R ₇ , R ₈ , R ₉ and R
Each ₁₀ independently represents a hydrogen atom, an alkyl group or a substituted or unsubstituted aralkyl group. ]

A benzophenone compound represented by the following general formula [6]:

[0021]

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[In the formula, Z represents a hydrogen atom or a hydroxyl group, and R ₁₁ and R ₁₂ each independently represent a hydrogen atom, an alkyl group, an alkoxy group or a hydroxyl group. ]

A cyanoacrylate compound represented by the following general formula [7]:

[0024]

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[Wherein, R ₁₃ represents an alkyl group. ]

An anilide oxalate compound represented by the following general formula [8]:

[0027]

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[In the formula, R ₁₄ represents a hydroxyl group or an alkoxy group, and R ₁₂ represents a hydrogen atom, a hydroxyl group, an alkyl group or an alkoxy group. ]

A triazine compound represented by the following general formula [9]:

[0030]

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[In the formula, R ₁₆ represents a hydroxyl group or an alkoxy group, and R _17, R _18, R ₁₉ and R ₂₀ each independently represent a hydrogen atom, an alkyl group or an alkoxy group. ], And an electrophotographic photoreceptor comprising:

Further, as a light stabilizer, the following general formula [1]
0], which comprises a hindered amine compound having a hindered amino residue in its structure.

[0033]

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In the present invention, when Ar ₁ is a substituted aryl group, the amine compound represented by the general formula [1] contained in the photosensitive layer has 1 to 4 carbon atoms as a substituent.
A lower alkyl group, a lower alkoxy group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, a benzyl group,
A phenyl group or a halogen atom can be selected, and when these substituents are a lower alkyl group or a lower alkoxy group, they may be further substituted with a lower alkoxy group having 1 to 4 carbon atoms or a halogen atom. Good, when the substituent is a benzyl group or a phenyl group, it has 1 to 1 carbon atoms.
It may be further substituted with 4 lower alkyl groups, lower alkoxy groups having 1 to 4 carbon atoms or halogen atoms.

In both cases where Ar ₁ is substituted or unsubstituted, the aryl group may be selected from phenyl, naphthyl, biphenylyl, anthryl, pyrenyl and the like.

When Ar ₂ is a substituted phenylene group, a substituted naphthylene group, a substituted biphenylene group or a substituted antrylene group, the substituent may be a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxy group having 1 to 4 carbon atoms. Group or a halogen atom, etc., and when these substituents are a lower alkyl group or a lower alkoxy group, they may be further substituted with a lower alkoxy group having 1 to 4 carbon atoms or a halogen atom. .

When L, M or N is a substituted aryl group, the same substituents as those described above that Ar ₁ can have can be selected as the substituent. L
Is a substituted alkyl group, a lower alkoxy group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms or a halogen atom can be selected as the substituent. In addition, L, M or N may be substituted or unsubstituted, and the aryl group may be selected from a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group and a pyrenyl group.

When R ₁ and R ₂ are a lower alkyl group or a lower alkoxy group, the lower alkyl group is a linear or branched alkyl group having 1 to 4 carbon atoms, and the lower alkoxy group is a 1 to 4 carbon atoms. Four straight or branched alkoxy groups can be selected. When R ₃ is a lower alkyl group, a linear or branched alkyl group having 1 to 4 carbon atoms can be selected as the lower alkyl group.

The following are examples of the benzotriazole-based compound represented by the general formula [4]. 2
-(5-methyl-2-hydroxyphenyl) benzotriazole, 2- [2-hydroxy-3,5-bis (α,
α-dimethylbenzyl) phenyl] -benzotriazole, 2- (3,5-di-tert-butyl-2-hydroxyphenyl) benzotriazole, 2- (3-ter
t-butyl-5-methyl-2-hydroxyphenyl)-
5-chlorobenzotriazole, 2- (3,5-di-t
tert-butyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3,5-di-tert-
Amyl-2-hydroxyphenyl) benzotriazole, 2- (2-hydroxy-5-tert-octylphenyl) benzotriazole, 2- [2-hydroxy-
3- (3,4,5,6-tetra-hydrophthalimide-
Methyl) -5-methylphenyl] benzotriazole.

The following are examples of the benzophenone-based compound represented by the general formula [6]. 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4
-N-octoxybenzophenone, 2,2 ', 4,4'
-Tetrahydroxybenzophenone, 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4,
4'-dimethoxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2-hydroxy-
4-octadecyloxybenzophenone, 4-dodecyloxy-2-hydroxybenzophenone.

The following are examples of the hindered amine compound represented by the general formula [10]. Dimethyl succinate 1- (2-hydroxyethyl) -4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate, poly {[6- (1,1,3,3-tetramethylbutyl) Amino-1,3,5-triazine-2,4-diyl] [(2,2,6,6-tetramethyl-4-piperidyl) imino] hexamethylene [(2,2,6,6-tetramethyl- 4-piperidyl) imino]｝, N, N′-bis (3-aminopropyl) ethylenediamine · 2,4-
Bis [N-butyl-N- (1,2,2,6,6-pentamethyl-4-piperidyl) amino] -6-chloro-1,
3,5-triazine condensate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,
2,2,6,6-pentamethyl-4-piperidinyl) sebacate, 2- (3,5-ditert-butyl-4-)
Bis (1,2,2,6,6-pentamethyl-4-piperidyl) hydroxybenzyl) -2-n-butylmalonate. A benzoate compound represented by the general formula [5]; a cyanoacrylate compound represented by the general formula [7]; an oxalic acid anilide compound represented by the general formula [8]; As the triazine-based compound represented by [9], commercially available ones are suitably used.
Even if these ultraviolet absorbers and light stabilizers are used alone,
Alternatively, two or more kinds may be used as a mixture.

The electrophotographic photoreceptor of the present invention has a photosensitive layer containing at least one kind of the above-mentioned amine compounds and further containing at least one kind of the above-mentioned ultraviolet absorbers and light stabilizers. There are various forms of the photosensitive layer,
The photosensitive layer of the electrophotographic photosensitive member of the present invention may be any of them. As representative examples, FIGS. 1 to 5 show such photoconductors.

The photoreceptor shown in FIG. 1 has a conductive layer 1 on which an amine compound, an ultraviolet absorber, a sensitizing dye and a binder resin are provided.

The photoreceptor shown in FIG. 2 has a photosensitive layer 2 in which a charge generation material 4 is dispersed in a charge transport medium 3 comprising an amine compound, an ultraviolet absorber and a binder resin on a conductive support 1.
1 is provided. In the present photoreceptor, the charge generation substance absorbs light to generate charge carriers, which are transported by the charge transport medium. In this case, it is desirable that the charge transporting material is transparent to light that generates charge carriers. Amine compounds have almost no absorption in the visible wavelength range,
It satisfies the condition that the charge generation material and the absorption wavelength range do not overlap.

The photoreceptor shown in FIG. 3 has a charge generation layer 5 mainly composed of a charge generation substance 4 on a conductive support 1 and an amine compound.
The photosensitive layer 22 is formed by laminating a charge transport layer 3 made of an ultraviolet absorber and a binder resin. In this photoreceptor, the light transmitted through the charge transport layer 3 reaches the charge generation layer 5,
The charge carriers are generated by being absorbed by the charge generating substance 4. The charge carriers are injected into the charge transport layer 3 and transported.

The photoreceptor of FIG. 4 has the photoreceptor of FIG. 3 provided with a photosensitive layer 23 in which the charge generation layer 5 and the charge transport layer 3 are stacked in the reverse order. Generation and transport of charge carriers can be explained by a mechanism similar to that described above.

The photoreceptor of FIG. 5 has a structure in which a protective layer 6 is further laminated on the charge generation layer 5 of the photoreceptor of FIG. 4 for the purpose of improving mechanical strength.

[0048]

BEST MODE FOR CARRYING OUT THE INVENTION The photoreceptor of the present invention can be manufactured according to a conventional method as follows. For example, the amine compound represented by the general formula [1] and the general formulas [4] to
The ultraviolet absorber and light stabilizer represented by [10] are dissolved together with a binder resin in a suitable solvent, and if necessary, a charge generating substance, a sensitizing dye, an electron-withdrawing compound or an antioxidant, a plasticizer, A coating solution is prepared by adding an agent, a pigment, and other additives. This coating solution is applied on a conductive support and dried to form a photosensitive layer of several μm to several tens μm, whereby a photoreceptor can be manufactured. In the case of a photosensitive layer comprising a charge generation layer and a charge transport layer, the above-mentioned coating solution is applied on the charge generation layer, or the charge generation layer is placed on the charge transport layer obtained by applying the above coating solution. Can be produced. The photoreceptor thus manufactured may be provided with an adhesive layer, an intermediate layer, and a barrier layer, if necessary.

As the solvent for preparing the coating solution, tetrahydrofuran, 1,4-dioxane, methyl ethyl ketone, cyclohexanone, acetonitrile, N, N-
Polar organic solvents such as dimethylformamide and ethyl acetate,
Aromatic organic solvents such as toluene and xylene, and chlorinated hydrocarbon solvents such as dichloromethane and 1,2-dichloroethane can be used. A solvent having high solubility for the amine compound and the binder resin is preferably used.

As sensitizing dyes, methyl violet,
Brilliant green, crystal violet, triarylmethane dyes such as acid violet, rhodamine B, eosin S, xanthene dyes such as rose bengal, thiazine dyes such as methylene blue, pyrylium dyes and thiapyrylium dyes such as benzopyrylium salts, Alternatively, a cyanine dye or the like can be used.

As electron-withdrawing compounds which form a charge transfer complex with an amine compound, chloranil, 2,3-
Quinones such as dichloro-1,4-naphthoquinone, 1-nitroanthraquinone, 2-chloroanthraquinone and phenanthrenequinone; aldehydes such as 4-nitrobenzaldehyde; 9-benzoylanthracene; indandione; 3,5-dinitrobenzophenone; , 4,7-
Ketones such as trinitrofluorenone, 2,4,5,7-tetranitrofluorenone, acid anhydrides such as phthalic anhydride and 4-chloronaphthalic anhydride, tetracyanoethylene, terephthalalmalenonitrile, 9-anthryl Cyano compounds such as methylidene malenonitrile, 3-benzalphthalide, 3- (α-cyano-p-nitrobenzal)-
And phthalides such as 4,5,6,7-tetrachlorophthalide.

Examples of the binder resin include polymers and copolymers of vinyl compounds such as styrene, vinyl acetate, vinyl chloride, acrylic acid ester, methacrylic acid ester and butadiene, polyvinyl acetal, polycarbonate, polyester, polyphenylene oxide, polyurethane, Various resins that are compatible with the amine compound, such as cellulose ester, phenoxy resin, silicon resin, epoxy resin, and the like. The amount of the binder resin used is usually in the range of 0.4 to 10 times, preferably 0.5 to 5 times the weight of the amine compound.

As the antioxidant, 2,6-di-ter
t-butyl-p-cresol, 2,6-di-tert-
4-methoxyphenol, 2-tret-butyl-4-
Methoxyphenol, 2,4-di-methyl-6-ter
t-butylphenol, 2,6-di-tert-butyl-4-methylphenol, butylated hydroxyanisole, stearyl-propionate-β- (3,5-di-te
rt-butyl-4-hydroxyphenyl, α-tocopherol, β-tocopherol, 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di-t
tert-butylanilino) -1,3,5-triazine,
Octadecyl-3- (3,5-di-tert-butyl-
4-hydroxyphenyl) propionate, 3,5-di-tert-butyl-4-hydroxy-benzylphosphonate-diethyl ester, 2,4-bis [(octylthio) methyl] -o-cresol, isooctyl-
Monophenolic compounds such as 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate. Triethylene glycol-bis [3- (3-ter
t-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-bis [3
-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], pentaerythrityl-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 2,2 -Thio-
Diethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], N,
N'-hexamethylenebis (3,5-di-tert-butyl-4-hydroxy-hydrocinnamamide), 1,
3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, tris- (3,5-di-tert-butyl-4-hydroxybenzyl)- Isocyanurate, 2,2-thiobis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (6-tert-butyl-4-methylphenol), 4,4′-butylidene-bis- (3 -Methyl-6-tert-butylphenol), 4,4′-thiobis (6-tert-butyl-3)
-Methylphenol), 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl)
And polyphenol compounds such as butane. These monophenolic compounds and polyphenolic compounds may be used alone or in combination of two or more.

The photosensitive layer according to the present invention may contain a well-known plasticizer for the purpose of improving film formability, flexibility and mechanical strength. As the plasticizer, for example, phthalate, phosphate, chlorinated paraffin, methylnaphthalene, epoxy compound, chlorinated fatty acid ester and the like can be used.

As the conductive support on which the photosensitive layer of the present invention is formed, well-known materials used for electrophotographic photosensitive members can be used. Aluminum, stainless steel, copper and other metal drums, sheets or laminates of these metals,
Deposits, metal powders, carbon black, copper iodide,
A plastic film, plastic drum, paper, paper tube, or a plastic film or plastic drum that has been rendered conductive by containing a conductive material by applying a conductive material of a polymer electrolyte together with a suitable binder and conducting the conductive treatment. Can be used.

[0056]

The present invention will be described below in detail with reference to examples. Parts in the examples represent parts by weight, and the concentration represents Wt%.

Example 1 The following bisazo pigment (charge generating agent No. 1) was used as a charge generating agent.
1)

[0058]

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1.0 part and 8.6 parts of a 5% tetrahydrofuran solution of a polyester resin (Vylon 200, manufactured by Toyobo Co., Ltd.) were added to 83 parts of tetrahydrofuran, and the mixture was placed in an agate pot containing agate balls. (Fritsch) for 1 hour to disperse. The obtained dispersion is applied to the aluminum surface of an aluminum-deposited PET film as a conductive support using a wire bar,
Dried at ℃ for 2 hours and further under reduced pressure for 2 hours.
m of the charge generation layer was formed. On the other hand, the following amine compound (amine compound No. 1) as a charge transporting agent

[0060]

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1.5 parts and 2- as UV absorber
18. A 5% 1,2-dichloroethane solution of 0.15 parts (5-methyl-2-hydroxyphenyl) benzotriazole (UV absorber No. 1) of polycarbonate resin (Iupilon Z, manufactured by Mitsubishi Engineering-Plastics Corporation) The amine compound was completely dissolved by applying ultrasonic wave to 75 parts. This solution was applied on the above-mentioned charge generating layer with a wire bar, and dried at 60 ° C. under normal pressure for 2 hours and further under reduced pressure for 2 hours to form a charge transport layer having a thickness of 20 μm, thereby producing a photoreceptor. .

Example 2 In Example 1, the ultraviolet absorbent No. Instead of using 1, 2- [2-hydroxy-
3,5-bis (α, α-dimethylbenzyl) phenyl]
A photoconductor was prepared in the same manner as in Example 1, except that benzotriazole (ultraviolet absorbent No. 2) was used.

Example 3 In Example 1, UV absorber No. Instead of using 1, 2- (2-hydroxy-5
A photoconductor was prepared in the same manner as in Example 1, except that (-tert-octylphenyl) benzotriazole (ultraviolet absorber No. 3) was used.

Example 4 In Example 1, the amine compound No. Instead of using amine compound No. 1, 1 and the following amine compound (amine compound No. 2)

[0065]

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A photoreceptor was prepared in the same manner as in Example 1, except that a mixture of 1: 1 by weight was used.

Example 5 In Example 4, UV absorber No. A photoconductor was prepared by the same way as that of Example 4 except that 2-hydroxy-4-methoxybenzophenone (ultraviolet absorbent No. 4) was used instead of that of Example 1.

Example 6 The procedure of Example 4 was repeated except that the ultraviolet absorbent No. 5 was used. A photoconductor was prepared in the same manner as in Example 4 except that 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate (ultraviolet absorbent No. 5) was used instead of using 1. Produced.

Example 7 In Example 4, the ultraviolet absorbent No. 1 was used. A photoconductor was prepared by the same way as that of Example 4 except that 2-ethylhexyl 2-cyano-3,3-diphenylacrylate (ultraviolet absorbent No. 6) was used instead of that of Example 1.

Example 8 The procedure of Example 4 was repeated except that the ultraviolet absorbent No. A photoconductor was prepared by the same way as that of Example 4 except that N- (2-ethylphenyl) -N '-(2-ethoxyphenyl) -oxamide (ultraviolet absorbent No. 7) was used instead of using 1.

Example 9 In Example 4, the ultraviolet absorbent No. Instead of using 1, 2- (2-hydroxy-4
-Octoxyphenyl) -4,6-di (2,4-xylyl) -1,3,5-triazine (UV absorber No.
A photoconductor was prepared by the same way as that of Example 4 except for using 8).

Example 10 The procedure of Example 4 was repeated except that the ultraviolet absorbent No. Instead of using 1, 2- as a light stabilizer
Bis (1,2,2,2,3- (3-di-tert-butyl-4-hydroxybenzyl) -2-n-butylmalonate
6,6-pentamethyl-4-piperidyl) (light stabilizer N
o. A photoconductor was prepared in the same manner as in Example 4, except that 1) was used.

Example 11 In Example 1, the amine compound No. Instead of using 1, the following amine compound (amine compound No. 3)

[0074]

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A photoconductor was prepared in the same manner as in Example 1 except that

[Example 12] In Example 1, the amine compound No. Instead of using 1, the following amine compound (amine compound No. 4)

[0077]

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A photoconductor was prepared in the same manner as in Example 1 except that

Example 13 In Example 1, the amine compound No. Instead of using 1, the following amine compound (amine compound No. 5)

[0076]

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A photoconductor was prepared in the same manner as in Example 1 except that

Example 14 In Example 1, the amine compound No. Instead of using amine compound No. 1, 3 and the following amine compounds (amine compound No. 6)

[0079]

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A photoreceptor was prepared in the same manner as in Example 1 except that a mixture having a weight ratio of 1: 1 was used.

[Example 15] In Example 1, the amine compound No. Instead of using 1, the following amine compound (amine compound No. 7)

[0082]

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A photoconductor was prepared in the same manner as in Example 1 except that

Comparative Example 1 A comparative photoconductor was prepared in the same manner as in Example 1, except that the ultraviolet absorber was omitted.

Comparative Example 2 A comparative photoconductor was prepared in the same manner as in Example 4, except that the ultraviolet absorber was omitted.

Comparative Example 3 A comparative photoconductor was prepared in the same manner as in Example 11, except that the ultraviolet absorbent was omitted.

[Examples 1 to 15 and Comparative Examples 1 to 3] The photosensitive members prepared in Examples 1 to 15 and Comparative Examples 1 to 3 were irradiated with 1,000 lux of light for 1 hour under fluorescent lamp illumination, and then electrostatically charged. The electrophotographic characteristics were evaluated using a copy paper test apparatus (trade name “EPA-8100” manufactured by Kawaguchi Electric Works Co., Ltd.).
First, the photosensitive member was subjected to a corona discharge of -6 kV in a dark place, and the charging potential V0 at this time was measured. Then 5.0lux
Was irradiated for 5 seconds to determine the residual potential Vr. This measurement was performed 4000 times continuously, and the first cycle and 400
The results of the 0th cycle are shown in [Table 1].

[0088]

[Table 1]

Example 16 1.5 parts of α-titanyl phthalocyanine (charge generating agent No. 2) was used as a charge generating agent in 3% toluene of polyvinyl butyral resin (Eslec BX-L, manufactured by Sekisui Chemical Co., Ltd.) 50 parts of the solution,
The dispersion was performed for 1 hour with an ultrasonic disperser. The obtained dispersion is applied on an aluminum surface of an aluminum-deposited PET film as a conductive support using a wire bar, and dried at 60 ° C. under normal pressure for 2 hours and further under reduced pressure for 2 hours to obtain a film thickness of 0.2 μm. Was formed. On the other hand, the amine compound No. 1 and 1.5 parts of UV absorber No. 1 0.15 part of 1 is an 8% 1,2-dichloroethane solution 1 of a polycarbonate resin (Iupilon Z, manufactured by Mitsubishi Engineering-Plastics Corporation)
Ultrasonic waves were added to 8.75 parts to completely dissolve the amine compound. This solution was applied on the above-mentioned charge generation layer with a wire bar, and then was heated at 60 ° C. under normal pressure for 2 hours and further under reduced pressure for 2 hours.
After drying for a time to form a charge transport layer having a thickness of 20 μm, a photoreceptor was prepared.

[Example 17] In Example 16, the charge generating agent No. A photoconductor was prepared by the same way as that of Example 16 except that X-type metal-free phthalocyanine (charge generating agent No. 3) was used instead of using Example 2.

Example 18 In Example 1, the charge generating agent No. Instead of using 1, the following trisazo compound (charge generator No. 4)

[0092]

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A photoreceptor was prepared in the same manner as in Example 1 except that the above was used.

Comparative Example 4 A comparative photoconductor was prepared in the same manner as in Example 17, except that the ultraviolet absorber was omitted.

[Examples 16 to 18, Comparative Example 4] Example 1
After irradiating the photoreceptors prepared in Examples 6 to 18 and Comparative Example 4 with light of 1000 lux for 1 hour under fluorescent lamp illumination, evaluation of electrophotographic characteristics was performed using an electrostatic copying paper test apparatus (trade name "EPA-8100"). Was done. First, the photosensitive member was placed in a dark place for -7.
A corona discharge of 0 kV was performed, and the charging potential V0 at this time was measured. Then, the sample was irradiated with 5 μW / cm ² monochromatic light of 790 nm for 5 seconds to determine the residual potential Vr. This measurement was continuously performed 4000 times, and the results at the first cycle and the 4000th cycle are shown in [Table 2].

[0096]

[Table 2]

Example 19 As the charge generator, the following thiapyrylium salt (charge generator N
o. 5)

[0098]

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0.1 part and the following amine compound (amine compound No. 8)

[0100]

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10 parts of UV absorber No. 1 to 0.
15 parts with a polycarbonate resin (Panlite K-13)
The mixture was added to 125 parts of an 8% 1,2-dichloroethane solution (trade name: 00, manufactured by Teijin Chemicals Ltd.), and ultrasonic waves were applied thereto to completely dissolve the charge generator, the amine compound and the ultraviolet absorber. This solution was applied to the aluminum surface of an aluminum-deposited PET film as a conductive support using a wire bar, and
After drying at 0 ° C. for 2 hours and further under reduced pressure for 2 hours, a film thickness of 20 μm was obtained.
m of the photosensitive layer was formed to prepare a photosensitive member. After irradiating the photoreceptor with 1,000 lux light for 1 hour under fluorescent light illumination, an electrostatic copying paper test apparatus (trade name “EPA-810”)
0 ") to evaluate the electrophotographic characteristics. First, the photoreceptor was subjected to a corona discharge of +8 kV in a dark place, and the charging potential V0 at this time was measured. Then, the sample was irradiated with 5.0 lux for 5 seconds to obtain a residual potential Vr. This measurement is performed continuously for 40
It was performed 00 times. As a result, V0 in the first cycle is +97
0 V and Vr are +30 V, and V at the 4000th cycle.
0 was +966 V and Vr was +43 V.

[0102]

As described above, the electrophotographic photoreceptor of the present invention prevents electrophotographic characteristics from deteriorating due to light fatigue, and has a stable chargeability and residual potential during repetition of a copying process. Body can be provided.

[Brief description of the drawings]

FIG. 1 is a cross-sectional view of a single-layer photoconductor for electrophotography.

FIG. 2 is a cross-sectional view of a single-layer photoconductor for electrophotography in which a charge generating substance is dispersed.

FIG. 3 is a cross-sectional view of an electrophotographic photoconductor in which a charge generation layer and a charge transport layer are laminated on a conductive support in this order.

FIG. 4 is a cross-sectional view of an electrophotographic photoconductor in which a charge transport layer and a charge generation layer are laminated in this order on a conductive support.

FIG. 5 is a cross-sectional view of an electrophotographic photoconductor provided with a protective layer.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Conductive support 2, 21, 22, 23, 24 Photosensitive layer 3 Charge transport medium, charge transport layer 4 Charge generating substance 5 Charge generating layer 6 Protective layer

 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Mitsutoshi Anzai 45, Miyukigaoka, Tsukuba, Ibaraki Pref.

Claims (8)

[Claims] 1. A conductive support having the following general formula [1] (In the formula, Ar ₁ represents a substituted or unsubstituted aryl group; Ar ₂ represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted group. R ₁ represents a hydrogen atom, a lower alkyl group or a lower alkoxy group, L represents a hydrogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and M represents a substituted or unsubstituted group. An aryl group of the following general formula [2]: (Wherein, R ₁ represents the same meaning as described above)
Valence group or the following general formula [3] (Wherein, R ₂ represents a hydrogen atom, a lower alkyl group or a lower alkoxy group, R ₃ represents a hydrogen atom, a halogen atom, or a lower alkyl group, and N represents a hydrogen atom, a substituted or unsubstituted aryl group. , M and n represent an integer of 0 to 4.). A photosensitive layer containing an amine compound represented by the following formula: wherein the photosensitive layer contains, as an ultraviolet absorber, a benzotriazole-based compound, a benzoate-based compound, a benzophenone-based compound, a cyanoacrylate-based compound, an oxalic acid anilide-based compound, or a triazine. An electrophotographic photoreceptor comprising: at least one compound selected from the group of hindered amine compounds; and at least one compound selected from the group of hindered amine compounds as a light stabilizer. 2. The electrophotographic photoconductor according to claim 1, wherein the ultraviolet absorber is a benzotriazole-based compound represented by the following general formula [4]. Embedded image [In the formula, R ₄ represents a hydrogen atom, a lower alkyl group or a halogen atom, and R ₅ and R ₆ each independently represent a hydrogen atom, an alkyl group or a substituted or unsubstituted aralkyl group. ] 3. The electrophotographic photoconductor according to claim 1, wherein the ultraviolet absorbent is a benzoate compound represented by the following general formula [5]. Embedded image [In the formula, X and Y represent a hydrogen atom or a hydroxyl group, provided that X and Y are not a hydrogen atom or a hydroxyl group at the same time, and R ₇ , R ₈ , R ₉ and R ₁₀ are each independently a hydrogen atom, Represents an alkyl group or a substituted or unsubstituted aralkyl group. ] 4. The electrophotographic photoconductor according to claim 1, wherein the ultraviolet absorber is a benzophenone compound represented by the following general formula [6]. Embedded image Wherein Z represents a hydrogen atom or a hydroxyl group;
₁₁ and R ₁₂ each independently represent a hydrogen atom, an alkyl group, an alkoxy group or a hydroxyl group. ] 5. The photoconductor for electrophotography according to claim 1, wherein the ultraviolet absorber is a cyanoacrylate compound represented by the following general formula [7]. Embedded image [Wherein, R ₁₃ represents an alkyl group. ] 6. The electrophotographic photoconductor according to claim 1, wherein the ultraviolet absorber is an anilide oxalate compound represented by the following general formula [8]. Embedded image [Wherein, R ₁₄ represents a hydroxyl group or an alkoxy group, and R ₁₅ represents a hydrogen atom, a hydroxyl group, an alkyl group, or an alkoxy group. ] 7. The electrophotographic photoconductor according to claim 1, wherein the ultraviolet absorber is a triazine compound represented by the following general formula [9]. Embedded image [In the formula, R ₁₆ represents a hydroxyl group or an alkoxy group, and R _17, R _18, R ₁₉ and R ₂₀ each independently represent a hydrogen atom, an alkyl group or an alkoxy group. ] 8. The electrophotographic photosensitive member according to claim 1, wherein the light stabilizer is a hindered amine compound having a hindered amino residue represented by the following general formula [10] in the structure. Embedded image