JPH02198451A - Photosensitive body - Google Patents

Abstract

PURPOSE:To suppress the degradation in photosensitivity and the increase in residual potential at the time of repetitive use by incorporating the compd. selected from a group consisting of specific compds. into the photosensitive body. CONSTITUTION:The compd. selected from the group consisting of the compds. expressed by the formulas I, II, etc., is incorporated into the photosensitive body. In the formula I, Are<1> denotes an aryl group having an electron attracting group; Ar<1>, Ar<3> denote a substd. or unsubstd. aryl group; Ar<2> denotes an arylene group; R<1>, R<2> denote a hydrogen atom, alkyl group or aryl group. In the formula II, Ar<4>, Ar<5> denote an aryl group; Ar<6> denotes an arylene group; Are<2> denotes an arylene group having an electron attracting group; R<3>, R<4> denote an alkyl group. The influence of the ozone generated at the time of the electrification of the photosensitive body is suppressed in this way. The degradation in the photosensitivity and the increase in the residual potential at the time of the repetitive use are suppressed.

Description

DETAILED DESCRIPTION OF THE INVENTION A. Field of Industrial Application The present invention relates to a photoreceptor, such as an electrophotographic photoreceptor.

In conventional electrophotographic copying machines using the Carlson method, after the surface of a photoreceptor is charged, an electrostatic latent image is formed by exposure, and the electrostatic latent image is developed with toner, and then a visible image is formed. Transfer and fix onto paper, etc. At the same time, the photoreceptor is subjected to removal of adhered toner, neutralization of static electricity, and surface cleaning, and is used repeatedly over a long period of time.

Therefore, as an electrophotographic photoreceptor, it not only has electrophotographic properties such as good charging characteristics and sensitivity, and low dark decay, but also has good printing durability, abrasion resistance, moisture resistance, etc. after repeated use. Physical properties, ozone generated during corona discharge,
It is also required to have good resistance to ultraviolet rays and the like during exposure (environmental resistance).

Conventionally, as electrophotographic photoreceptors, inorganic photoreceptors having a photosensitive layer mainly composed of an inorganic photoconductive substance such as selenium, zinc oxide, or cadmium sulfide have been widely used.

On the other hand, the use of various organic photoconductive substances as materials for photosensitive layers of electrophotographic photoreceptors has been actively developed and researched in recent years.

For example, in Japanese Patent Publication No. 50-10496, poly-N-vinylcarbazole t2. 4. An organic photoreceptor having a photosensitive layer containing 7-trinitro-9 fluorenone is described. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with high sensitivity and durability by assigning the charge generation function and charge transport function to different substances in the photosensitive layer. ing. In such so-called function-separated type electrophotographic photoreceptors, substances that exhibit each function can be selected from a wide range of materials, so it is relatively easy to produce electrophotographic photoreceptors with arbitrary characteristics. Is possible.

At present, such electrophotographic photoreceptors are mainly used for negative charging, and as described in JP-A No. 60-247647, a thin charge generation layer is provided on a support, and a relatively thick charge generation layer is provided on the support. A configuration is adopted in which a charge transport layer is provided.

The reason for this is that in the case of using negative charging, the mobility of holes among carriers is high, so it is possible to use materials with hole transport properties, which is advantageous in terms of photosensitivity, etc., whereas materials with electron transport properties can be used. There are almost no materials with excellent properties,
Or, it cannot be used because it is carcinogenic or teratogenic.

However, when negatively charged by a corona charger, ozone is generated in the atmosphere due to corona discharge, resulting in deterioration of environmental conditions. This causes deterioration of the material on the surface of the photoreceptor and adsorption of ionic substances onto the surface of the photoreceptor. In particular, when the carrier transport substance in the photosensitive layer deteriorates, the photosensitivity decreases significantly, and also causes a decrease in charging potential and an increase in residual potential during repeated use.
Image quality deteriorates and photoreceptor life is shortened. In the case of negative charging, a large amount of ozone is generated, which is a serious problem.

Object of the invention An object of the invention is to suppress the influence of ozone generated when a photoreceptor is charged, and to prevent a decrease in photosensitivity during repeated use.
It is an object of the present invention to provide a photoreceptor that can suppress an increase in residual potential.

21 Structure of the invention and its effects The present invention provides a compound represented by the following general formula [1], a compound represented by the following general formula (II), and a compound represented by the following general formula [1 [[]
This invention relates to a photoreceptor containing a compound selected from the group consisting of a compound represented by the following formula [■] and a compound represented by the following general formula [■].

General formula [I] [Are': represents an aryl group having at least an electron-withdrawing group.

Ar', Ar3: represents a substituted or unsubstituted aryl group.

Ar2: represents a substituted or unsubstituted arylene group.

R', R2 represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. ] General formula (II) (Ar', Ar5: represents a substituted or unsubstituted aryl group.

Ar6: represents a substituted or unsubstituted arylene group.

Are2: represents an arylene group having at least an electron-withdrawing group.

R3 and R4 represent substituted or unsubstituted alkyl groups.

] General formula (I[[] [Ar? : Represents a substituted or unsubstituted aryl group.

Ar'': represents a substituted or unsubstituted arylene group.

Are″: represents an arylene group having at least an electron-withdrawing group.

R5 and R6 represent substituted or unsubstituted alkyl groups.

] General formula (IVI (Ar9, Ar10: represents a substituted or unsubstituted aryl group.

Ar: represents an aryl group having at least a dialkylamino group.

Are': represents an aryl group having at least an electron-withdrawing group. ] The photoreceptor of the present invention uses novel charge transport substances represented by the above general formulas (1) to [IV], and this point is a remarkable feature.

In other words, there is a desire for the emergence of new photoconductive materials and charge transport materials with good properties, but in reality there are an infinite number of organic compounds that have so-called conjugated systems in their molecular structures. The reality is that promising molecular structures are determined practically from a large number of molecular structures.

Here, when designing molecules of charge transport substances, electron-donating substituents are provided as side chains of conjugated systems.

On the other hand, the use of an electron-withdrawing group as a side chain of a conjugated system has not been carried out due to concerns that it may reduce the hole transport ability of the charge transport material.

Here, the present inventor introduced an electron-withdrawing group into the side chain as shown in general formula (I), and as a result of various studies,
The following remarkable effects were achieved.

In other words, by employing the charge transport material of the present invention, the durability against ozone generated during corona charging inside copying machines etc. is dramatically improved. We were able to suppress the decline.

The reason for this is assumed to be as follows.

Ozone decomposition proceeds as shown in the reaction formula below.

The transported charges are transferred to and trapped in the ozone decomposition product 2A as shown by the dashed line.

-1/ As a result, optical carrier transmission is inhibited, resulting in a decrease in photosensitivity and an increase in residual potential. It is thought that when there is a strong electron-donating group such as a diarylamino group or dialkylamino group on the side of the ozone decomposition product, the ionization potential decreases and photocarriers are trapped in the product shell.

On the other hand, when the charge transport material used in the photoreceptor of the present invention is decomposed by ozone, the following occurs.

1 2A 3
1ゝ＼ノ
〆ゝ＼ノ 11(.

(However, R'', Rb, Rc, and R' represent substituents.) When the charge transport substance 1 is decomposed by ozone, a carbonyl compound is generated through an intermediate.

At this time, as shown in FIG. 1, the ionization potential I of one ozone decomposition product 2A is 1
．． According to this, an "aryl group having an electron-withdrawing group" is selected as a substituent for nitrogen in the ozone decomposition product. Therefore, as shown in FIG. 1, the ionization potential of the product and to becomes higher than the ionization potential of the product due to the action of the electron-withdrawing group, making it difficult for photocarriers in the photosensitive layer to be trapped by the product. Therefore, even if the ozone decomposition of the charge transport material progresses, the decrease in photosensitivity, etc. is suppressed.

In the above ozone decomposition reaction formula, the "compound represented by the general formula (I)" was explained, but the general formula (■3,
C■], (For the compound represented by IVI, an electron-withdrawing group is substituted on the side where the dialkylamino group is present with respect to the double bond, and the same effect can be achieved.

Furthermore, the compounds of general formulas [I] to (IV) all have high carrier transport ability, are chemically stable, have excellent durability against light and electrical loads, and have level matching with various CGMs. can be achieved, and a highly sensitive OPC (organic electrophotographic photoreceptor) can be produced.

As the charge transport material, compounds represented by the general formula (I) can be used alone or in combination of two or more. The same applies to the compounds represented by general formulas (II), (I[], and [IV]).

Moreover, the compounds represented by the general formulas [1], (II), (I[I), and [■] can also be used in combination with each other.

Next, the contents of the compounds of general formulas [I] to (IV) will be described.

"Electron-withdrawing group" refers to a substituent within a molecule that tends to attract electrons from other parts when hydrogen is used as a standard. This is determined from the so-called induced effect and resonance effect. Examples include a nitro group, a nitroso group, a carbonyl group, a carboxyl group, a nitrile group, and a halogen group (halogen atom). Regarding halogen groups, electron-withdrawing properties due to induction effects and electron-donating properties due to resonance effects coexist, but the effect of increasing the ionization potential due to electron-withdrawing properties is greater, and thus it is included in the electron-withdrawing groups here.

Hammett's rule (Ha
a+mett's rule), the dissociation reaction of benzoic acid and its derivatives (25°C
, in aqueous solution) and look at the σ value of the substituent. If σmeta and σpara of the substituent are positive, it may be considered an electron-withdrawing group.

In general formula [I), the substituent for Are' is:
In addition to electron-withdrawing groups, examples include alkyl groups, aryl groups, alkoxy groups, and the like. Examples of substituents for Ar' and Ar'' include halogen atoms, hydroxy groups, alkyl groups, alkoxy groups, substituted amine groups, and aryl groups. In addition to these, examples of substituents for Ar' include the aforementioned Examples include electron-withdrawing groups.R1
, RZ include a halogen atom, a hydroxy group, an alkyl group, an alkoxy group, a substituted amino group, an aryl group, and the like.

Next, examples of compounds represented by general formula (I) are:
For example, those having the following structural formula can be mentioned, but are not limited thereto.

(ff bottom margin) Next, compounds represented by the general formulas (n), (I[[), and [IV)] will be described.

In the formula, Ar', Ar', and Ar' represent an aryl group, with phenyl and naphthyl groups being preferred. Arb,
Ar'' represents an arylene group, preferably a phenylene group or a naphthylene group.Are2 and Are' represent an arylene group having at least an electron-withdrawing group, and preferably a phenylene group or a naphthylene group.Are' is a phenyl group. Preferably. R3, R4, R5, and R6 represent an alkyl group, preferably an alkyl group having 1 to 8 carbon atoms. The substituted alkyl group includes an aralkyl group. The aralkyl group is preferably a benzyl group or a phenethyl group. In the above, examples of the substituent include an alkyl group, an aralkyl group, an alkoxy group, an aryl group, an aryloxy group, or a substituted amino group.

Are' may be further substituted with a dialkylamino group.

Examples of the dialkylamino substituent for Are' and Ar11 include a dimethylamino group, a diethylamino group, a dipropylamino group, and a dibutylamino group.

The substitution position of the dialkylamino group is preferably the para position.

Ar' and Ar'' are preferably phenyl groups, and examples of the substituents for Ar9 and ArI(l) include the above-mentioned substituents, particularly methyl and methoxy groups, and the preferred substitution position is para-position.

Next, specific examples of compounds represented by the general formulas CI[], CI[[], and (IV'l) will be illustrated, but the compounds are not limited thereto.

(Leaving space below) Exemplary compound ■ ■ ■ ■ ■ ■ ■ ■ ■−Bi■ ■ ■ ■ ■ ■−返■ ■ ■ ■ ■ ■ ■ ■ Addition example compound■ ■ ■ ■ ■ ■ ■ η ■ Vessel■ ■ ■ ■ ■ ■ ■ ■ ■ Minoru ■ ■ ■ ■ Add ■ ■ ■ ■ ■ n-22 CI (1 0 bottom margin) ■ V-2 ■ ■ ■ ■ ■ ■ Minoru ■ V-13 ■ ■ ■-Add ■=5 ■-V -27 ■-21 V-22 ■-% ■-24 1'Ir V-29 The above-mentioned stilbene derivatives can be easily synthesized by known synthesis methods. For example, Organic
Reactions vol, 25 P, 73 (Jo
hn Willey +&5ons, Inc.), an aromatic aldehyde represented by the following maximum (V) and a dialkyl phosphonate represented by the following maximum [VI] are mixed in a solvent such as N,N-dimethylformamide. , sodium alfoxide, etc., by condensation.

Here, Ar', Ar5% Ar6, Are'', R3
, R4 represents the same group as in the general formula (I[], and R represents an alkyl group or an aryl group.

When introducing an electron-withdrawing group into the compound of general formula [■], RX is added to AβCff3 into a raw material that does not have an electron-withdrawing group.
, FeC15 (X is an electron-withdrawing group), and this X is introduced.

For example, to synthesize exemplified compound n-1, the following reaction is performed.

Compounds represented by other general formulas [I], CI[[], and (IV'l) can also be synthesized by performing the same reactions as above.Specifically, as shown in the following reaction formulas, can be easily obtained by condensing the corresponding aromatic aldehyde and dialkyl phosphonate in a solvent such as N,N dimethylformamide in the presence of sodium alkoxide, etc.An electron-withdrawing group can also be obtained. , can be introduced in the manner described above.

What is represented by general formula (I) side j 1 item” and 2 Y Next, the structure, prescription, etc. of the electrophotographic photoreceptor will be described.

Various types of electrophotographic photoreceptors are known, and any of these types is included.

Usually, those illustrated in FIGS. 2 to 7 are preferable. In the photoreceptors shown in FIGS. 2 and 3, photosensitive layers 4A and 4B each consisting of a laminate of a charge generation layer 2 and a charge transport layer 3 are provided on a conductive support 1. In FIG. 3, the stacking order of the charge generation layer 2 and the charge transport layer 3 is different. Figure 4,
As shown in FIG. 5, a photosensitive layer 4A,
4B may be provided. In this way, when the photosensitive layer has a two-layer structure, a photoreceptor having the most excellent electrophotographic properties can be obtained. Further, as shown in FIGS. 6 and 7, a carrier-generating substance 6 is included in the layer 7 containing the carrier-transporting substance.
may be dispersed to form a photosensitive layer 4D, and this photosensitive layer 4D may be provided directly on the conductive support 1 or via an intermediate layer 5.

Further, a protective layer may be provided as the outermost layer.

When the photosensitive layer has a two-layer structure, which of the charge generation layer 2 and the charge transport layer 3 should be the upper layer depends on whether the charge polarity is positive or not.
Determined by which one you choose. In other words, when forming a negatively charged photosensitive layer, it is advantageous to use the charge transport layer 3 as an upper layer, and this is because the charge transport material in the charge transport layer 3 is a material that has a high transport ability for holes. This is because.

Therefore, the electrophotographic photoreceptors shown in FIGS. 2 and 4 are of a negatively charged type.

Since the amount of ozone generated in a negatively charged photoreceptor is greater than that in a positively charged photoreceptor, the effect of preventing a decrease in photosensitivity by the photoreceptor of the present invention is even more remarkable.

The charge transport layer 3 is prepared by dissolving a compound represented by C11 to [IV] in a solvent together with a suitable binder resin, and applying the solution to the conductive support 1 or the charge generation layer 2, either directly or through an intermediate layer. It can be formed by coating and drying.

The charge generation layer 2 and the photosensitive layer 4D having a single layer structure are formed on the conductive support 1 and the charge transport layer 3, which are the lower layer surfaces, either directly or with an intermediate layer such as an adhesive layer or a barrier layer provided as necessary. To,
For example, it can be formed by the following method.

(1) Vapor phase deposition method (2) Paint coating method a) A method of applying a solution paint in which a charge transport substance is dissolved in a suitable solvent.

b) A method in which a charge transport material is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., and a dispersion paint obtained by mixing and dispersing the charge transport material with a binder as necessary is applied.

The charge generation layer 3 and the single-layer photosensitive layer 4D may contain compounds represented by formulas [1) to [IV], if necessary.

The vapor deposition method includes a vacuum evaporation method, a spackling method, an ion blating method, a CVD method, etc., and the paint application method includes a dipping method, a spray method, an air doctor method, a doctor blade method, a reverse roll method, etc. An appropriate method is selected depending on the physical properties of the paint.

In the charge transport layer 3, the content ratio of the compound represented by -maximum [■] to [IV] is the binder to 1 part by weight of the compound represented by -maximum [I] to [■]. The amount is preferably 0.5 to 10 parts by weight. Also, -maximum (1) ~ (rV)
The compound represented by can also be included in the charge generation layer 2 and the photosensitive layer 4D, and the content ratio at this time is (-maximum [I] ~
Compound represented by [■]: charge generating substance) = (5 to 10
0 parts by weight: preferably 100 parts by weight.

Further, as the charge generating substance, in general, any inorganic pigment or organic dye can be used as long as it absorbs visible light and generates free charges. In addition to inorganic pigments such as amorphous selenium, trigonal selenium, selenium arsenic alloy, selenium-tellurium alloy, cadmium sulfide, cadmium selenide, cadmium selenide sulfide, mercury sulfide, lead oxide, and lead sulfide, the following representative examples mR-bearing materials such as those shown may also be used.

(1) Azo pigments such as monoazo pigments, polyazo pigments, metal complex azo pigments, pyrazolone azo pigments, stilbene azo and thiazole azo pigments.

(2) Perylene pigments such as perylene anhydride and perylene imide.

(3) anthraquinone derivatives, anthanthrone derivatives, dibenzpyrenequinone derivatives, pyrantrone derivatives,
Anthraquinone or polycyclic quinone pigments such as violanthrone derivatives and isoviolanthrone derivatives (4) Indigoid pigments such as indigo derivatives and thioindigo derivatives (5) Phthalocyanine pigments such as metal phthalocyanines and metal-free phthalocyanines (6) Diphenylmethane pigments pigments, carbonium pigments such as triphenylmethane pigments, xanthine pigments and acridine pigments (7) quinone imine pigments such as azine pigments, oxazine pigments and thiazine pigments (8) methine pigments such as cyanine pigments and azomethine pigments (9) quinoline Pigments (10) Nitro pigments (11) Nitroso pigments (12) Benzoquinone and naphthoquinone pigments (13)
Naphthalimide pigment (14) Perinone pigment such as bisbenzimidazole derivative Next, specific examples of preferred charge generating substances will be described.

Examples of azo pigments include the following.

A N=N Ar” N=N, a, r
12A-N=N-Ar"-N=N-Ar"-Ar"
-N=N-A N=N N=N A-N=N-Ar” -CH=CH-Ar”A N
=N-Ar"-CH=CH-Ar"Ar13-N=
N-A N=N CH=CH Ar''' N=N [However, among the above-mentioned maximums, ArII, Ar12 and Arl3: each substituted or unsubstituted carbocyclic aromatic ring group, + = RIZ, RI3 and R+4; Each of them is an electron-withdrawing group or a hydrogen atom, and at least one of R11 to RI4 is an electron-withdrawing group such as a cyano group, A r " (However, R16 and R17 are each a hydrogen atom or a substituted or unsubstituted group. Substituted alkyl group, RI8 is substituted or unsubstituted argyl group or substituted or unsubstituted aryl group>
, Y is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a carboxyl group to a sulfo group, a substituted or unsubstituted carbamoyl group, or a substituted or unsubstituted sulfamoyl group (provided that m is 2 or more). ), Z is an atomic group necessary to constitute a substituted or unsubstituted carbocyclic aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring. , R15 is a hydrogen atom, a substituted or unsubstituted amino group,
(A substituted or unsubstituted carbamoyl group, carboxyl group or ester group thereof, Ar'' is a substituted or unsubstituted aryl group, n is an integer of 1 or 2, and m is an integer of 0 to 4.) Further, polycyclic quinone pigments of the following largest group can also be used in combination as carrier generating substances.

Azo-based illustrative pigments (where X is a halogen atom, a nitro group,
Represents a cyano group, a cyano group, or a carboxyl group, p is Ω
An integer of ~4, q represents an integer of 0~G. ) Furthermore, the following carrier-generating substances can be specifically exemplified as preferable ones.

x type m metal phthalocyanine τ type m gold i phthalocyanine chloroaluminum phthalocyanine titanyl phthalocyanine vanadyl phthalocyanine ε type copper phthalocyanine chloroindium phthalocyanine
No. 0-172045, patent application No. 63-147871 (6
(Application filed on May 15, 2013) Compounds described in the specification etc. can be used.

Although the binder used in the photoreceptor of the present invention can be arbitrarily selected, it is preferable to use a hydrophobic, high dielectric constant, electrically insulating film-forming polymer. Examples of such high molecular weight polymers include, but are not limited to, the following.

(1) Polycarbonate (2) Polyester (3) Methacrylic resin (4) Acrylic resin (5) Polyvinyl chloride (6) Polyvinylidene chloride (7) Polystyrene (8) Polyvinyl acetate (9) Styrenic copolymer resin (e.g. styrene butadiene copolymer, styrene methyl methacrylate copolymer) (10) Acrylonitrile copolymer resin (e.g. vinylidene chloride-acrylonitrile copolymer, etc.) (11) Vinyl chloride-vinyl acetate copolymer (12) Vinyl chloride-acetic acid Vinyl-maleic anhydride copolymer (13) Silicone resin (14) Silicone-alkynd resin (15) Phenol resin (e.g. phenol-formaldehyde resin, m-cresol-formaldehyde resin, etc.) (16) Styrene-alkynd resin (17) Poly-N-vinylcarbazole (18) Polyvinyl butyral (19) Polyvinyl formal (20) Polyhydroxystyrene (21) Polyarylate These binders can be used alone or in a mixture of two or more.

As the binder for forming the surface (protective) layer, a transparent resin having a volume resistivity of 108 Ω1 or more, preferably 10 I0 Ω (2) or more, more preferably 10'3 Ω or more is used. Further, it is advantageous for the binder to contain at least 50% by weight of a resin that is cured by light or heat. Furthermore, if necessary, the surface (protective) layer may contain less than 50% by weight of a thermoplastic resin for the purpose of improving processability and physical properties (preventing cracks, imparting flexibility, etc.).

The intermediate layer functions as an adhesive layer or a barrier layer, and in addition to the binder resin, examples include evapolyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate- Maleic acid copolymers, casein, N-alkoxymethylated nylon, starch, etc. are used.

As the conductive support, the following are mainly used, but the present invention is not limited thereto.

■) Metal plates such as aluminum plates and stainless steel plates.

2) A thin layer of metal such as aluminum, palladium, gold, etc. is provided on a support such as aluminum or plastic film by lamination or vapor deposition.

3) A layer containing a conductive compound such as a conductive polymer, indium oxide, or tin oxide is provided by coating or vapor deposition on a support such as a plastic film or a support such as 1) or 2) above.

Furthermore, the photosensitive layer may contain one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential or fatigue during repeated use, and the like. Examples of electron-accepting substances that can be used here include succinic anhydride, maleic anhydride, dibromosuccinic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromo phthalic anhydride to 3-nitro phthalic anhydride, 4- Nitrophthalic anhydride, pyromellitic anhydride, mellitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, 0-dinitrobenzene, m-dinitrobenzene, 1, 3.5-1
- dinitrobenzene, paranitrobenzonitrile, vicryl chloride, quinone chlorimide, chloranil, brumanil, dichlorodicyanobarabenzoquinone, anthraquinone, dinitroanthraquinone, 9-fluorenylidene [dicyanomethylenemalonodinitrile], polynitro 9-fluorenylidene-[dicyanomethylene malonodinitrile], picric acid, 0-nitrobenzoic acid, p-nitrobenzoic acid, 3.5-dinitrobenzoic acid to pentafluorobenzoic acid, 5-nitrosalcylic acid, 3.5-dinitocosalicylic acid, phthalic acid , mellitic acid, and other compounds with high electron affinity.

In addition, the addition ratio of the electron-accepting substance is carrier-generating substance:electron-accepting substance-10070.01 to 200 by weight.
, preferably too: 0.1-100.

Furthermore, silicone oil may be present as a surface modifier. Further, an ammonium compound may be contained as a durability improver.

Even more ultraviolet! I@L collectors, antioxidants, etc. may also be used.

Preferred ultraviolet absorbers include nitrogen-containing compounds such as benzoic acid, stilbene compounds, and derivatives thereof, triazole compounds, imidazole compounds, toridine compounds, coumarin compounds, oxadiazole compounds, thiazole compounds, and derivatives thereof. type is used.

Examples of antioxidants include hindered phenol, hindered amine, paraphenylene diamine, aryl alkane, hydroquinone, spirochroman, spiroindanone, and derivatives thereof. Examples include yellow compounds and organic phosphorus compounds. Specific examples of these compounds include Japanese Patent Application Nos. 61-162866 and 1988-188975.
No., @61-195878, No. 61-15'7G44
It is described in No. 162867, No. 61-204469217492, No. 61-, No. 61-195879, No. 61, No. 6L-217493, and No. 61-221541.

In the photoreceptor of the present invention, it is also possible to use other carrier transport substances in combination within a range that does not impair the effects of the present invention.

Examples of such carrier transport substances include carbazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives, imidacilone derivatives, imidazolidine derivatives, bisimidazolidine derivatives,
Styryl compounds, hydrazone compounds, pyrazoline derivatives, oxacilone derivatives, benzothiazole derivatives, benzimidazole tbK forms, quinazoline tAK forms, benzofuran derivatives, acridine derivatives, phenazine derivatives,
aminostilbene derivatives, triarylamine derivatives,
Phenyl diamine derivatives, stilbene derivatives, poly-
One or more types selected from N-vinylcarbazole, poly-1-vinylpyrene, poly-9-vinylpyrene, etc. can be mentioned.

Although the thickness of the charge transport layer can be changed as necessary, it is usually preferably 5 μm to 30 μm.

The thickness of the charge generation layer is preferably 0.01 to 5 μm, more preferably 0.05 to 3 μm.

When forming a single-layer photosensitive layer in which a particulate charge generating substance is dispersed, it is preferable to use a binder in an amount of 5 parts by weight or less per 1 part by weight of the charge generating substance.

Further, when the charge generation layer is configured as a dispersed type layer using a binder, it is preferable to use the binder in an amount of 5 parts by weight or less per 1 part by weight of the charge generation substance.

The photoreceptor of the present invention can be applied to various light sources such as halogen lamps, tungsten lamps, LEDs (light emitting diodes), gas lasers such as helium-neon, argon, and helium-cadmium, and semiconductor lasers.

The photoreceptor of the present invention has a wide variety of uses such as electrophotographic copying machines and printers.

E. Examples Examples of the present invention will be explained in more detail below.
The present invention is not limited thereby, and of course includes other embodiments with various modifications.

Preparation of electrophotographic photoreceptor〉 Spotting 1 Polyvinyl butyral resin r
Made of Lj (manufactured by Union Carbide), thickness 0
．． A 2 μm intermediate layer was formed.

Next, 1 part by weight of the following exemplified charge generating material (CGM) was added,
Polycarbonate resin “Panlite L1250J (
0.5 parts by weight (manufactured by Kijin Kasei Co., Ltd.) and 120 parts by weight of 1,2-dichloroethane were dispersed in a solution using a sand mill for 10 hours and then applied with a wire bar to form a charge generation layer of 0.2 μm. Formed.

Next, a solution of 12 parts by weight of Exemplified Compound (1-1), 15 parts by weight of polycarbonate resin [Panlite, 11300J (manufactured by Kijin Kasei Co., Ltd.)], and 120 parts by weight of 1,2-dichloroethane was applied using a blade coater. Thickness: 23
A charge transport layer of μm thickness was formed to obtain the photoreceptor of Example 1.

In Example 1, the following comparative compound (1) was used instead of exemplified compound (I-1). Otherwise, an electrophotographic photoreceptor was produced in the same manner as in Example 1.

Comparative Compound (1) On a conductive support made of a polyester film laminated with aluminum foil, vinyl chloride vinyl acetate-vinyl alcohol copolymer "SRESOC A-5J" was used.
(manufactured by Tsukisui Kagaku Co., Ltd.) with a thickness of 1 μm was formed.

Next, 1 part by weight of the following CGM was dispersed for 48 hours using a ball mill in a solution of 0.8 parts by weight of polyvinyl formal resin [Denka Polmar #20J (manufactured by Denki Kagaku Kogyo Co., Ltd.)] and 100 parts by weight of 1,2-dichloroethane. The solution was spray coated to form a charge generation layer of 0.3 μm.

Next, 10 parts by weight of the exemplary compound (I-2), 12.5 parts by weight of polyester resin "Vylon 200" (manufactured by Toyobo Co., Ltd.)
parts by weight, 1,2-dichloroethane 100 parts by weight 2-8,
2 to 4 In Example 1, the charge transport substance was exemplified by compound (I-
2), (n-1), (II-5), (II[-1), (
Example 2.3 was carried out sequentially by changing I[+-4), (IV-1), and (IV-7)L, and otherwise following the same procedure as in Example 1.
．． 4.5.6.7.8 Electrophotographic photoreceptors were prepared.

In addition, in ~ Example 1, the charge transport substance was changed to the following comparative compounds (2), (3), and (4), and the rest was Example 1.
An electrophotographic photoreceptor was prepared in the same manner as described above.

A solution of comparative compound (3) was applied using a blade coater to a thickness of 20 μm.
Electrophotographic photoreceptors of Examples were prepared by forming a charge transport layer of m.

Examples 10 to 12, (9) In Example 9, the charge transport substances were changed to the above-mentioned exemplified compounds (II-2), (III-2), and (#-8), and the other procedures were the same as in Example 9. Example 10
．． 11.12 electrophotographic photoreceptors were prepared.

In addition, in Example 9, the charge transport substance was replaced with a comparative compound (
9), and a comparative example (
9) The electrophotographic photoreceptor was prepared.

Example 13 A conductive support made of a polyester film deposited with aluminum was coated with a film made of polyvinyl formal [Vinylesoku L, I (manufactured by Tsukisui Kagaku Co., Ltd.) with a thickness of 0.3 μm.
An intermediate layer of m was formed.

Next, as CGM, 1 part by weight of τ-type metal-free phthalocyanine and polyvinyl butyral resin "ESRESOC BLSJ" were added.
(Manufactured by Block Chemical Co., Ltd.) 1 part by weight, ■, 2 dichloroethane 1
A charge generation layer was formed by dispersing 0.00 parts by weight using an ultrasonic dispersion machine and applying the solution using a wire bar.

Next, 10 parts by weight of the exemplary compound (1-3), 12 parts by weight of polycarbonate resin [Panlite L-1250J (manufactured by Kijin Kasei), and the antioxidant Sanol L S-26 were added.
A charge generation layer having a thickness of 18 μm was formed by applying a solution containing 0.5 parts by weight of No. 26 (manufactured by Sankyo) and 100 parts by weight of 1,2-dichloroethane using a blade, thereby obtaining a photoreceptor of an example.

Examples 14 to 16, Comparative Example (13) In Example 13, the charge transport substances were changed to the above-mentioned exemplified compounds (It-4), (I[[-5), and (IV-8), respectively, and the other examples were as follows. In the same manner as in Example 9, electrophotographic photoreceptors of Examples 14, 15, and 16 were successively prepared.

In addition, in Example 13, the charge transport materials were compared: 16 parts by weight of Pyrone Z-200J (manufactured by Mitsubishi Gas Chemical Co., Ltd.), 2
A charge transport layer having a thickness of 22 μm was formed by applying a solution containing 120 parts by weight of -dichloroethane by a dip coating method to obtain a photoreceptor of an example.

In Example 17, the charge transport substances were changed to the above compounds (n-7), (I[[-7), and (IV-8), respectively,
Other than that, in the same manner as in Example 9, Example 18.1
An electrophotographic photoreceptor of 9.20 was prepared.

Further, an electrophotographic photoreceptor of Comparative Example (17) was prepared in the same manner as in Example 17 except that the charge transport substance was changed to Comparative Compound (17).

Evaluation of electrophotographic properties> Compound (13) An electrophotographic photoreceptor of Comparative Example (13) was prepared in the same manner as in Example 13 except that L was changed.

Comparative Compound (13) Example 17 A 0.5μ thick film made of polyhydroxystyrene resin “Maruka Linker Ml (manufactured by Maruzen Petrochemical Co., Ltd.)” was coated on a conductive support made of an aluminum drum by dip coating.
An intermediate layer of m was formed.

Next, the following CGMI parts by weight, polyvinyl formal resin "decane formal #20J O, 6 parts by weight, 1.2
- 100 parts by weight of dichloroethane was added to 1 part by weight using a sand mill.
The liquid obtained by dispersing for 0 hours was applied by dip coating to form a charge generation layer with a thickness of 0.25 μm.

Next, 12 parts by weight of the exemplified compound (1-7), bisphenol Z type polycarbonate resin, and electrostatic copying paper tester RSP-428 model (Kawaguchi Electric Co., Ltd.) The electrophotographic characteristics were measured using a dynamic method using a newly manufactured product.

First, the surface potential Va (V) when negatively corona charged for 5 seconds under the discharge condition of 40.17 A, and then exposed to white light to increase the surface potential from -500 [V] to 50 (V). Exposure amount required to reduce E5oJ: [1ux-s
ec) was measured. This operation was then repeated 100 times. The results are shown in the table below.

(The following is a blank space.) As can be seen from the table, the photoreceptors of Examples have better charging ability and sensitivity than the photoreceptors of Comparative Examples, and the photosensitivity does not decrease even after repeated use.

In addition, each photoreceptor of Examples was used in an electrophotographic copying machine [UBix
1550 J (manufactured by Konica) was installed on a modified machine and a live copy test was conducted. As a result, even after 1,000 repetitions, the same good copy images as the initial one were obtained.

[Brief explanation of the drawing]

FIG. 1 is a diagram schematically showing changes in ionization potential due to decomposition of a charge transport substance. FIG. 2, FIG. 3, FIG. 4, FIG. 5, FIG. 6, and FIG. 7 are partial cross-sectional views showing examples of electrophotographic photoreceptors, respectively. In addition, in the symbols shown in the drawings, t--conductive support 2-------Charge generation layer 3--=--Charge transport layer 4A, 4B, 4 D -------- One photosensitive layer 5 --
---------- Intermediate layer 6 ------- One charge generating substance 7 ------- This is a layer containing a charge transporting substance. Agent Patent Attorney Hiroshi Aisaka

Claims (1)

[Claims] 1. A compound represented by the following general formula [I], a compound represented by the following general formula [II], a compound represented by the following general formula [III], and the following general formula [IV] A photoreceptor containing a compound selected from the group consisting of compounds represented by: General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [Are^1: Represents an aryl group having at least an electron-withdrawing group. Ar^1, Ar^3: represents a substituted or unsubstituted aryl group. Ar^2: represents a substituted or unsubstituted arylene group. R^1, R^2: represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. ] General formula [II] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [Ar^4, Ar^5: Represents a substituted or unsubstituted aryl group. Ar^6: represents a substituted or unsubstituted arylene group. Are^2: represents an arylene group having at least an electron-withdrawing group. R^3, R^4: represents a substituted or unsubstituted alkyl group. ] General formula [III] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [Ar^7: Represents a substituted or unsubstituted aryl group. Ar^8: represents a substituted or unsubstituted arylene group. Are^3: represents an arylene group having at least an electron-withdrawing group. R^5, R^6: represents a substituted or unsubstituted alkyl group. ] General formula [IV] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [Ar^9, Ar^1^0: Represents a substituted or unsubstituted aryl group. Ar^1^1: represents an aryl group having at least a dialkylamino group. Are^4: represents an aryl group having at least an electron-withdrawing group. ]