JPS6024549A - Photosensitive body - Google Patents

Abstract

PURPOSE:To improve the photosensitivy and the quality of an image by incorporating a specified bisazo compound into a carrier generating phase and a specified aromatic amino compound into a carrier transferring phase. CONSTITUTION:A bisazo compound represented by formula I is incorporated into a carrier generating phase, and an aromatic amino compound represented by formula IV into a carrier transferring phase. A photosensitive body having high sensitivity and high spectral sensitivity in the whole visible light region is obtd. by well combining said bisazo compound used as CGM with said aromatic amino compound used as CTM. In the formulae, each of Ar<1> and Ar<2> is a carbocyclic aromatic ring, each of R<1> and R<2> is an electron withdrawing group or H; A is a group represented by formula II or III; X is OH or the like; Y is H, halogen or the like; Z is a carbocyclic aromatic ring; R<3> is H, amino or the like; A' is aryl; each of n and m is an integer; each of R<7>-R<10> is H, alkyl or the like; each of R<13>-R<16> is H, halogen or the like; and each of R<11> and R<12> is H, 1-40C alkyl or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION 1. Prior Art The present invention relates to a photoreceptor, such as an electrophotographic photoreceptor, having a photosensitive layer comprising a carrier generation phase and a carrier transport layer.

2. Prior Art According to conventionally known electrophotographic photoreceptors, a carrier-generating substance (hereinafter referred to as "CGM") that absorbs visible light and generates charge carriers (hereinafter simply referred to as "carriers") is used.
There is a thing. ) A carrier generation layer containing (
Hereinafter, it may be referred to as rCGLJ. ) and CGL of and
A carrier transport layer (hereinafter sometimes referred to as rCTLJ) containing a carrier transport substance (hereinafter sometimes referred to as rCTMJ) that transports either or both of positive and negative carriers generated in The combination constitutes a photosensitive layer.

In this way, by assigning the two necessary basic functions of carrier generation and carrier transport to the separate layers constituting the photosensitive layer, it is possible to select a range of materials that can be used in the composition of the photosensitive layer. In addition to being wide-ranging, it becomes possible to independently select materials or material systems that optimally perform each function.

In addition, this also provides various characteristics required in the electrophotographic process, such as high surface potential when charged, high charge retention capacity, high photosensitivity, and high stability during repeated use. It becomes possible to obtain an electrophotographic photoreceptor having such characteristics.

As the above-mentioned photosensitive layer, for example, the following ones are known.

(1) CG composed of amorphous selenium or cadmium sulfide
A structure in which L and CTL made of poly-N-vinylcarbazole are laminated.

(2) CG composed of amorphous selenium or cadmium sulfide
A structure in which L and CTL containing 2,4.7-) dinitro-9-fluorenone are laminated.

(3) A structure in which a CGL composed of a perylene derivative and a CTL containing an oxadiazole derivative are laminated (
(See US Pat. No. 3,871,882).

(4) A CGL composed of Lydia Blue or Methyl Scarylium and a CTL containing a pyrazoline crocodile conductor
(Refer to Japanese Unexamined Patent Publication No. 51-90827).

(5) CGL consisting of amorphous selenium or its alloy;
Patent application No. 14725/1989, which has a structure in which CTL containing a polyarylalkane aromatic amine compound is laminated.
1 specification).

(6) A structure in which a CGL containing a perylene derivative and a CTL containing a polyarylalkane aromatic amino compound are laminated (Japanese Patent Application No. 19907/1983).

Although many types of functionally separated photosensitive layers are known, in conventional electrophotographic photoreceptors having such photosensitive layers, the photosensitive layer changes when subjected to repeated electrophotographic processes. It has the disadvantage of severe electrical fatigue and a very short service life.

For example, when subjected to an electrophotographic process repeatedly,
The potential history state of the electrophotographic photoreceptor is not maintained stably,
Stable image forming characteristics cannot be obtained.

In addition, specific bisazo compounds can be used as CGMs, for example, in JP-A-55-117151 and JP-A-54.
- Although disclosed in Publication No. 145142, etc., the CG
Even in combination with CTM, which is said to be able to be combined with M, the above-mentioned drawbacks are still considerable. As can be understood from this, a carrier transporting substance that is effective against a particular carrier-generating substance is not necessarily effective against other carrier-generating substances, and It cannot be said that a carrier-generating substance that is effective against other carrier-transporting substances is also effective against other carrier-transporting substances. If the combination of both substances is inappropriate, not only will the electrophotographic sensitivity be low, but also the discharge efficiency will be poor especially in low electric fields, resulting in a large residual potential, and in the worst case, repeated use. The potential accumulates over time, making it practically impossible to use for electrophotography.

In this way, it is thought that there is no lawful means of selecting a suitable combination of the constituent substances of the carrier generation phase and the constituent substances of the carrier transport layer, and an advantageous combination is determined practically from among many substance groups. There is a need to.

On the other hand, in a photoreceptor using poly-N-vinylcarbazole as the CTM, for example as in (1) above, the film is hard and brittle because poly-N-vinylcarbazole lacks flexibility. It has the disadvantage of being prone to cracking and peeling, and poor durability. Therefore,
When a plasticizer is added to increase flexibility, it has the disadvantage that electrophotographic properties deteriorate, such as increased residual potential and capri in the image.

In addition, using a low molecular weight organic compound as a charge transport material,
Efforts have been made to obtain an electrophotographic photoreceptor with excellent electrophotographic properties and film strength by using a polymeric binder and a substance that generates an arbitrary charge. As a transport substance, for example, 2,5-
Bis(P-diethylaminophenyl)-: r, -j,
Oxadiazole derivatives such as 4-oxadiazole are selected and used as preferred substances, but these have poor compatibility with polymeric binders, resulting in easy crystallization and poor thermal stability. It has the disadvantage of being inferior.

Furthermore, the technology of using a pyrazoline compound as a photoconductive material for an electrophotographic photoreceptor is disclosed in, for example, US Pat.
It is described in the specification of No. 729 and is well known, but it is used as a material that absorbs light and generates a charge, and also transports the charge, and is used as a charge transport material responsible only for transporting the charge. It's not something that exists.

Furthermore, the technique of using a pyrazoline compound as a charge transport material is described in, for example, U.S. Pat. It has poor compatibility with the polymer binder added to
When a polymeric binder is used in an amount necessary to obtain desirable physical properties, the pyrazoline compound thermally crystallizes, which clouds the charge transport layer and reduces light transmittance, which in turn reduces the sensitivity of the photoreceptor. This results in a decrease in

Further, a charge transport layer which causes turbidity as described above generally has poor layer uniformity and storage stability, and also tends to have poor charging characteristics. The reality is that a practically preferable heavy-duty transport material has not been found for producing electrophotographic photoreceptors.

3. Purpose of the Invention The purpose of the present invention is to have a photosensitive layer consisting of a combination of a carrier generation phase and a carrier transport layer, to exhibit high sensitivity, and to provide high sensitivity when repeatedly used in an electrophotographic process, etc. Another object of the present invention is to provide a photoreceptor in which a potential history state is maintained stably and a good visible image can always be formed.

Another object of the present invention is to provide a photoreceptor having a charge transport layer with improved film strength, uniformity, and stability by using a charge transport material with excellent compatibility with a polymeric binder. be.

4. Structure of the invention and its effects, that is, the present invention provides a photoreceptor having a photosensitive layer consisting of a carrier generation layer and a carrier transport layer, in which the carrier generation phase contains a bisazo compound represented by the following general formula [■]. and the carrier transport layer contains an aromatic amine compound represented by the following general formula (n).

General formula [I]: [However, in this general formula, Ar' and Ar'': each substituted or unsubstituted carbocyclic aromatic ring group, or substituted or unsubstituted heterocyclic aromatic ring group, R1 and R2: electron-withdrawing group or hydrogen atom (at least one of R1 and R2 is -CN, -CA!, etc.), -N0
(electron-withdrawing group such as 2), -NH8O2-R However, R4 and R5 are each a hydrogen atom, a substituted or unsubstituted alkyl group, and R6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. 〉 Y is a hydrogen atom, a hydrogen atom, a substituted or unsubstituted alkyl group, an alkoxy group, a carboxyl group, a sulfo group, a substituted or unsubstituted carbamoyl group, or a substituted or unsubstituted sulfamoyl group ( However, when m is 2 or more, they may be different groups.) 2 represents a substituted or unsubstituted carbocyclic aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring. Necessary atomic groups: R3 is a hydrogen atom, a substituted or unsubstituted amino group, a substituted or device-substituted carbamoyl group, a carboxyl group or an ester group thereof, A' is a substituted or unsubstituted aryl group, n is 1 or an integer of 2, m is an integer of 0 to 4 0] General formula [■]: [However, in this general formula, R7, R8, R11 and Hlo are hydrogen atoms, substituted or unsubstituted alkyl groups , cycloalkyl group, alkenyl group, aryl group, benzyl group or aralkyl group, H13, H14, B111 and Hlll are hydrogen atoms,
Halogen atom, human xyl group, substituted or unsubstituted alkyl group, Schiffn alkyl group, alkenyl group, aryl group, aralkyl group, alkoxy group, amino group, alkylamino group or arylamino group, R'' and B 12 are , a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a cycloalkyl group,
Alkenyl group, Schifftetraalkenyl group, aryl group, or aralkyl group (However, R11 and R1! may jointly form a saturated or unsaturated hydrocarbon ring having 3 to 10 carbon atoms)) , the above "phase" in the present invention is,
In addition to the case where the material forms so-called layers, it also includes the case where the constituent materials form phases in which they are in contact with each other.

According to the present invention, the bisazo compound represented by the general formula [■] is used as a CGM, and the bisazo compound represented by the general formula [1] is used as a CGM.
Using the aromatic amino compound shown as CTM,
By skillfully combining these, it is possible to provide a photoreceptor that has extremely high sensitivity compared to conventional dual-layer photoreceptors and also has high spectral sensitivity throughout the visible light region. .

Further, the photoreceptor of the present invention has high charge retention and surface strength, has an extremely low residual potential, and therefore exhibits stable performance even after repeated use, and does not accumulate charge. In addition, during the formation of the carrier generation phase and the carrier transport phase, shrinkage of the film or crystallization of the contained substances does not occur, and therefore problems of peeling and clouding do not occur.

The effects of the present invention can only be obtained by using a combination of the specific substances of the above general formula as the carrier-generating substance and the carrier-transporting substance, respectively. Even if there are substances other than those used in the present invention as carrier transport substances, such as poly-N-vinylcarbazole,
If 2,4°7-dolinitro-9-fluorenone or oxadiazole conductor is used, the above-mentioned excellent effects cannot be obtained. Conversely, the same applies when other substances are used as the carrier generating substance.

In the present invention, as the carrier transport substance, in the general formula (II), one or both of R7 and Rs and one or both of R@ and 110 are benzyl groups, and one or both of R13 and R14 and R15 and one or both of R1@ is an electron-donating substituent having a 1 effect (negative induction effect) or -M effect (negative mesomeric effect), i.e., a halogen atom, a hydroxyl group, a substituted or unsubstituted alkyl group, a cyclo Particularly high sensitivity is obtained when a compound is an alkyl group, alkenyl group, aryl group, aralkyl group, alkoxy group, amino group, alkylamino group, or arylamino group.

Examples of such compounds are shown as (n-18) to (ll-27) and (II-41) to (II-43).

5. Examples Hereinafter, the present invention will be explained in more detail with reference to Examples.

First, the compounds of the general formulas [■] and [■] used in the present invention will be specifically illustrated.

Among the bisazo compounds represented by the general formula CI), preferred are those represented by the following general formula (Ia).

General formula (Ia): N A-N=N-Ar1-C=CM-Ar2-N=N-LA
[However, Ar', Ar'' and A are the same as defined in general formula CI).] More preferred are especially Ar in general formula (Ia).
", Ar" is a compound consisting of the following.

Ar, Ar: represents a substituted or unsubstituted phenyl group, and substituents include alkyl groups such as methyl and ethyl groups, alkoxy groups such as methoxy and ethoxy groups, and halogen atoms such as chlorine and bromine atoms. , hydroxyl and cyano groups.

Specific examples of the bisazo compound represented by the general formula CI) include those having the following structural formula, but are not limited thereto.

(I-2) (I-s) (I-n) (I-12) (I-14) (I-15) (I-16) (I-20) (I-21) (I-22) (I-24) (I-25) (I-26) (I-27) (I-28) (■-fish) (■-(to)) (I-31) o2 (I-34) N (I-36) N (I-37) N (I-38) (I-39) (I-41) (I-42) (I-43) (I-44) (I-45) (I-46) (I-47) (I-48).

(I-50) (I-51) (I-52) 3) (I 54) cA' (I-55) (■-Seki) ()-57) (I-Guo) (I-59) ( ( i-61) (I-62) (I-63) (I 64) CH3 (I-65) (I-66) (I-67) (I-69) (l-70) (I-71) ( I -73) (I -76) (I -77") (i-79) CN (I -80) CN (I -81) (I-82) (I-83) Next, 1 general formula (II) Typical examples of aromatic amine compounds represented by are listed below.

(n-1) 1.1-bis(4-N,N-diethylamino-2-methylphenyl)heptane (It-2) 1.1-bis(4-N,N-dimethylamino-2-methoxyphenyl) -Memethylpropane (n-3) 1,1-bis(4-N, N-di(p-tolyl)amino-2-methylphenylcocyclohexane (II-4) 1,1-bis(4-N, N-diethylamino-2-methylphenyl)-1-phenylmethane (II-s) a, 3-diphenylarylidene-4゜4
'-bis(N,N-diethyl-m-)luidine) (n 6 ) a + a g a', a'-tetotukis (4-N.

N-diethylamino-2-methylphenyl)-p-xylene (u-7) 1,1-bis(4-N,N-diethylamino-2-ethylphenyl)-2-phenylethane (JT-8) 1,1 , 5.5-Tetotukis (4-N.

N-dimethylamino-2-methyl7enyl)pentane ([-9)1.1-bis(4-N,N-diethylamino-2-ethylphenyl)-4-methylcyclohexane (II-10)1. 1-bis(4-N,N-dimethylamino-2-methylphenyl)cyclohexane (II-11) 1.1-bis(4-N-ethyl-N-methylamino-2-methylphenyl)-3-methyl Cyclohexane (n-12) 1,1,2,2-tetrakis (4-N.

N-dimethylamino-2-methyl7enyl)ethane (n-13) 1.1-bis(4-N,N-diethylamino-2-methylphenyl)-3-phenylpropane (II-14) 1. 1-bis(4-N,N-dimethylamino-2-methylphenyl)-1-(4-methoxyphenyl)methane (II-15) 1.1-bis(4-N,N-dimethylamine-2- methylphenyl)-1-(4-hydroxyphenyl)methane (n-16)1.1-bis(4-N,N-dimethylaξ
)-2-methylphenyl)-1-(2,4-dimethoxyphenyl)methane (IF-17)
1.1-bis(4-N,N-dimethylamino-2-ethylphenyl)-1-(2,4-dimethylphenyl)methane (II-18) 1.1-bis(4-N,N-dimethylphenyl)-1-(2,4-dimethylphenyl)methane (II-18) benzylamino-2-methylphenyl)pentane (, [-19) 1,1-bis(4-N,N-dibenzylamino-2-methoxyphenyl)-2-methylpropane (II-20) 1,1- Pi, *(4-N,N-dibenzylamino-2-methylphenyl)cyclohexane (l-21)1.1-bis(4-N,N-dibenzylamino-2-methylphenyl)-1-phenylmethane (II-22) 1,1-hyx(4-N,N-dibenzylamino-2-methylphenyl)-1-Schiff's hexylmethane (■-phantom)1,1-bis(4-N,N -dibenzylamino-2-methoxyphenyl)-1-cyclohexylmethane (■-separate) 1,1-bis (7i to 4NIN-dipenta)
-2-methylphenyl) 1=1pan(I[-25)1,1-bis(4-N,N-dibenzylamino-2-methoxyphenyl)propane(■-陀)1,1-bis( 4-N,N-dipentalag)-2-methylphenyl)n-butane (II-27) 1 ,1-pi14-N,N-dibenzylamino-2-methoxyphenyl)n-butane (II-28) 1 .1-bis(4-N,N-diethylaminophenyl)hebutane (II 29) 1 e 1-bis(4-N,N-dimethylaminophenyl)-2-methyl7'apan(II-30) 1 , 1-bis(4-N,N-di(p
-tolyl)aminophenyl]cyclotetrahexane 1-31) 1.1-bis(4-N,N-diethylaminophenyl)-1'? Phenylmethane 1-32) 1,1-bis(4-N,N-dibenzylaminophenyl)pentane (■-feather) 1,1-bis(4-N,N-dibenzylamino 7-el)-2- Methylpropane (■-audience) 1. l-bis(4-N,N-dibenzylaminophenyl)cyclohexane 1-35) 1.1-bis(4-N,N-dibenzylaminophenyl)-1-phenylmethane (■-%) 1.1 -Bis(4-N,N-dibenzylaminophenyl)-1-cyclohexylmethane 1-37) 1.1-Bis(4-N,N-dibenzylamino 7-el)propane (■-A) 1,1 -bis(4-N,N-dibenzylaminophenyl)n-butane [[-39)1.1-bis(4-N,N-diethylamine-2,5-dimethylphenyl)heptane (TI-40) 1, 1-bis(4-N,N-diethylamino-2,5-dimethoxyphenyl)-1-phenylmethane 1-41)1.1-bis(4-N,N-dibenzylamino-2,5-dimethylphenyl) )-1-cyclohexylmethane ([-42)1.1-bis(4-N,N-dibenzylamino-2,5-dimethylphenyl)n-butane ([-43)1.1-bis(4-N , N-dibenzylamino-2,5-dimethoxyphenyl)n-butane Next, the present invention will be specifically explained with reference to the drawings.

The photoreceptor of the present invention is constructed as shown in FIG. 1, for example. That is, a carrier generation layer 2 containing the above-described bisazo compound as a main component is formed on the conductive support 1, and a carrier transport layer 2 containing the above-mentioned aromatic amino compound as a main component is formed on the carrier generation layer 2. The layers 3 are laminated, and the carrier generation layer 2 and the carrier transport layer 3 are combined into a photosensitive layer 4.
Here, the material of the conductive support 1 is, for example, a sheet of metal such as aluminum, nickel, copper, zinc, radium, silver, indium, tin, platinum, gold, stainless steel, or silver. For example, as shown in FIG. 2, an insulating substrate IA can be used.
The conductive support 1 can also be configured by providing a conductive layer IB thereon. In this case, the substrate IA is suitably flexible, such as paper or a plastic snack sheet, and yet has sufficient strength against stresses such as bending and tensile stress. The conductive layer IB can also be provided by laminating metal sheets, vacuum depositing metal, or by other methods.

The carrier generation layer 2 may be made of a bisazo compound alone, or may be made of a bisazo compound added with an appropriate binder resin, or may be made of a bisazo compound, or may be made of a bisazo compound added with a suitable binder resin, or may be made of a bisazo compound, or a material having high mobility for carriers of specific or non-specific polarity (i.e., a carrier). The kernels formed by adding a transport substance) can be formed.

A specific method for forming the bisazo compound is to vacuum evaporate the bisazo compound onto the support, or to apply the bisazo compound dissolved or dispersed in a suitable solvent alone or together with a binder resin and dry it. Here are some ways to do it.

In this latter method, binder resins or carrier transport substances may be added, in which case
The ratio of carrier generating substance: binder resin: carrier transporting substance is 1: (0 to 100): (0 to 500) by weight.
), particularly preferably 1:(θ~10):(0~50).

Examples of the solvent or dispersion medium used in the above method include n-butylamine, diethylamine, ethylenediamine, isopropanolamine, monoethanolamine, triethanolamine, triethylenediamine, N,N-
Dimethylformamide, acetone, methyl ethyl ketone, cyclohexanone, benzene, toluene, xylene,
Chloroform, 1,2-silo-loethane, dichloromethane, tetrahydro7rane, dioxane, methanol, ethanol, isopropanol, ethyl acetate, butyl acetate, dimethyl sulfoxide, and others can be used.

Further, as the binder resin, for example, polyethylene,
Addition polymerization type resins and polyaddition type resins such as polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenol resin, polyester resin, alkyd resin, polycarbonate resin, silicone resin, mejimino resin, etc. , polycondensation type resins, and copolymer resins containing two or more of the repeating units of these resins, such as vinyl chloride-vinyl acetate copolymer resins, vinyl chloride-vinyl acetate-maleic anhydride copolymers In addition to insulating resins such as composite resins, polymeric organic semiconductors such as bo9-N-vinylcarbazole can be used. The ratio of this binder resin to the bisazo compound is 0 to 100% by weight, particularly 0 to 10% by weight:i
: It is within the range of .

The CGI 2 includes an appropriate CTM as necessary.

may be added.

Furthermore, this carrier generation 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 in particular include succinic anhydride, maleic anhydride, dibromaleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride,
Nato-2-bromo-7thalic anhydride, 3-ditro-phthalic anhydride,
4-nitrophthalic anhydride, pyromellitic anhydride, mellitic anhydride, tetracyanoethylene, tetracyanoquinodimethane, o-dinitrobenzene, m-dinitrobenzene, 183.5-trinitrobenzene, varanitrobenzonitrile, picli chloride, quinone chlorimide, chloranil, pullmanil, diku p0 dicyanobara benzoquinone, anthraquinone, dinitroant 2quinone,
2,7-sinitrofluorenone, 2,4,7-dolinitotetrafluorenone, 2,4,5,7-tetonidotetrafluorenone, 9-fluorenylidene [dicyanomethylene malonodinitrile], polynitro-9-fluorenylidene - [dicyanomethylenemalonodinitrile], picric acid,
O-nitrobenzoic acid, p-nitrobenzoic acid, 3.5-dinitrobenzoic acid, pentafluorobenzoic acid, 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, heptatalic acid,
Examples include mellitic acid and other compounds with large electrophilicity. Furthermore, the addition ratio of the electron-accepting substance is as follows: carrier-generating substance: electron-accepting substance = 1
00:0.01-200 Preferably 1oo:o, 1
~100.

The thickness of the CGL 2 formed as described above is:
Preferably o, o o s ~ 20 μm 1 Particularly preferably 0.05 to 5 fim 0 If it is less than 0.005 μm, sufficient photosensitivity cannot be obtained, and if it exceeds μm, sufficient charge retention cannot be obtained. .

In addition, the CTL3 contains the aromatic amino compound described above,
It can be formed in the same manner as the above-mentioned CCl2 (that is, by coating alone or dissolving and dispersing it together with the above-mentioned binder resin and drying). And other CT
M may also be included.

In this case, the blending ratio of the binder resin and the total carrier transport substance is preferably 10 to 500 parts by weight per 100 parts by weight of the binder resin.
When polycarbonate is used as the binder resin, it is preferable to use from 200 parts by weight of the total carrier transport material per 100 parts by weight of polycarbonate because excellent electrophotographic properties can be obtained.

Furthermore, the above-mentioned electron-accepting substance can be added to this carrier transport layer for the purpose of improving sensitivity and further reducing residual potential or fatigue during repeated use. When this electron-accepting substance is added to both the carrier generation layer and the carrier transport layer, the electron-accepting substances added to each layer may be completely or partially the same, or may be completely different depending on the case. do not have. Note that the electron-accepting substance may be added to either one of the carrier-transporting layers. The proportion of the electron-accepting substance added to the carrier-transporting layer is, in terms of weight ratio, total carrier-transporting substance:electron-accepting substance=100: o, oi~
100 preferably 100:0.1-50.

The thickness of the carrier transport layer 3 formed in this way is 2
~100 μm, preferably 5 to 30 μm.

The present invention has been described above in accordance with the specific structural examples shown in FIG. 1 and FIG. This is sufficient, and the mechanical structure of the electrophotographic photoreceptor can be arbitrarily selected.

For example, as shown in FIG. 3, a suitable intermediate layer 5 may be provided on the conductive support 1, the carrier generation layer 2 may be formed through this, and the carrier transport layer 3 may be formed thereon. 0
This intermediate layer 5 has a function of preventing free carriers from being injected from the conductive support 1 into the photosensitive layer 4 when the photosensitive layer 4 is charged, and also has the function of preventing the photosensitive layer 4 from being injected into the photosensitive layer 4 integrally with the conductive support. It can have a function as an adhesive layer for adhering to. Materials for the intermediate layer 5 include metal oxides such as aluminum oxide and indium oxide, acrylic resins, methacrylic resins, vinyl chloride resins, vinyl acetate resins, epoxy resins, polyurethane resins, phenol resins, polyester resins, alkyd resins, Polymer materials such as polycarbonate resin, silicone resin, melamine resin, vinyl chloride-vinyl acetate copolymer resin, and vinyl chloride-vinyl acetate-maleic anhydride copolymer resin can be used.

Further, as shown in FIG. 4, a carrier transport layer 3 is formed on the conductive support 1 with or without the intermediate layer 5, and a carrier generation layer 2 is formed thereon. Layer 4 may also be configured.

Further, FIG. 5 shows a structure in which the above carrier-generating substance (bisazo compound) is dispersed in a carrier-transporting phase containing the above-mentioned aromatic amino compound (i.e., a combination of a carrier-generating substance phase and a carrier-transporting substance phase). An example in which a single-layer photosensitive layer (consisting of a mixed layer) is formed is shown below.

Hereinafter, the present invention will be described in more detail with reference to specific examples.

Vinyl chloride-vinyl acetate-maleic anhydride copolymer ``Eslec M''
Made of F-10J (manufactured by Tsukimizu Kagaku Kogyo Co., Ltd.) with a thickness of approximately 0.1
An intermediate layer of .mu.m was provided. Next, the structural formula (I-1
2 g of the bisazo compound shown in 5) was dispersed with 100- of 1,2-dichloroethane in a ball mill for 12 hours,
The obtained dispersion was applied onto the intermediate layer using a tosoter blade, and dried sufficiently to form a CGL with a thickness of about 0.3 μm.
was formed.

On the other hand, 11.2511 of the aromatic amino compound represented by the structural formula (II-4) described above and 15 g of polycarbonate resin [Panlite I, -1250J (manufactured by Teijin Chemicals) were mixed into 1
．． Dissolved in 100% of 2-dichloroethane, applied the resulting solution onto the CGL using a doctor blade, and dried at a temperature of ℃ for 1 hour to form a CTL with a thickness of 12 μm. An electrophotographic photoreceptor based on the invention was manufactured.

This will be referred to as "Sample 1".

Examples 2 to 5 In the formation of CGL, structural formulas (I-5), (I-81), (I-82) and (
Example 1 except that each of those shown in I-83) was used.
Four types of electrophotographic photoreceptors according to the present invention were manufactured in exactly the same manner as described above. These shall be referred to as "Sample 2,""Sample3,""Sample4," and "Sample 5."

Examples 6 to 7 In the formation of CTL, the same procedure as in Example J was carried out except that the compounds represented by the structural formula (II-22) and <I[-38> described above were used as aromatic amino compounds, respectively. Manufacturing an electrophotographic photoreceptor according to the present invention 19.

These will be referred to as "Sample 6" and "Sample 7."

W: An intermediate layer was provided on the conductive support in the same manner as in Example 1, and 2 g of the bisazo compound represented by the structural formula (I-1) and polycarbonate resin "Panlite L-125" were added.
0J 1# was added to 1,2-dichloroethane 100- and dispersed in a ball mill for 12 hours. The resulting dispersion was applied onto the intermediate layer using a doctor blade, and dried sufficiently to form a layer with a thickness of approx. A 0.5 μm CGL was formed.

A CTL was formed on this CGL in the same manner as the CTL was formed in Example 1, thereby manufacturing an electrophotographic photoreceptor according to the present invention. This was designated as "Sample 8".

Comparative Example 1 Comparison was made in the same manner as in Example 1, except that in the formation of CTL in Example 1, a pyrazoline compound having the following structural formula was used in place of the aromatic amino compound represented by general formula (n). An electrophotographic photoreceptor was manufactured. This is called “Comparative sample 1”.
”.

Comparative Example 2 In the formation of CTL in Example 1, #1 was applied using an oxadiazole derivative having the following structural formula A in place of the aromatic amino compound represented by general formula (II).
A comparative electrophotographic photoreceptor was produced in the same manner as described above. This will be referred to as "comparative sample 2."

Structure 2 For each of the electrophotographic photoreceptors obtained as described above (Samples 1 to 8 and Comparative Samples 1 and 2), an "electrometer 5P-428 model" (manufactured by Kawaguchi Electric Seisakusho) was used. The electrophotographic properties were investigated using this method. That is,
Acceptance potential VA (V) when the photoconductor surface is charged for 5 seconds with a charging potential of -6KV and potential after dark decay for 5 seconds (
The exposure amount E/(lux·sec) required to attenuate the initial potential) Vl to A was investigated. The results were as shown in Table 1 below.

Table-1 Also, Samples 1 to 6, Comparative Sample 1 and Comparative Sample 2
A dry electrophotographic copying machine rU-Bix2000 R
J (manufactured by Konishiroku Photo Industry Co., Ltd.) for continuous copying, and the black paper potential v b (v) at an exposure aperture value of 1.0
and blank paper potential Vw (V) were measured using an "Ellen Static Voltmeter Model 144D-ID" (manufactured by Monroe Electronics Inc.) immediately before development.The results are shown in the table below. The rules were as shown in 2.

10th @20 Figure 3 40th Figure S

Claims (1)

[Scope of Claims] 1. A photoreceptor having a photosensitive layer consisting of a carrier generation phase and a carrier transport phase, wherein the carrier generation phase contains a bisazo compound represented by the following general formula (I), and the carrier transport phase A photoreceptor comprising an aromatic amine compound represented by the following general formula (IF). General formula [■]: A-N=N-Ar -C=C-Ar -N=N-A1 R1, R2 [However, in this general formula, Ar' and Ar'': each substituted or unsubstituted carbon ring aromatic ring group, or a substituted or unsubstituted heterocyclic aromatic ring group, R1 and R2: each an electron-withdrawing group or a hydrogen atom (provided that at least one of R' and R2 is an electron-withdrawing group), However, R4 and R5 are each a hydrogen atom, a substituted or unsubstituted alkyl group, R6 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group> Y is a hydrogen atom, a substituted or substituted alkyl group, or a substituted or unsubstituted aryl group. or unsubstituted alkyl group, alkoxy group, carboxyl group, sulfo group, substituted or unsubstituted carbamoyl group, or substituted or unsubstituted (sulfamoyl group (however, when n is 2 or more, mutually parent groups) ) 2 is an atomic group necessary to constitute a substituted or unsubstituted carbohydric aromatic ring or a substituted or unsubstituted heterocyclic aromatic ring, R3 is a hydrogen atom, a substituted or unsubstituted amine group, substituted or unsubstituted carbamoyl group, carboxyl group or its nistyl group, A is a substituted or unsubstituted aryl group, n is an integer of 1 or 2, m is an integer of θ to 4 )] - General formula [■]: ( ) [However, in the general formula of Jin, R7, R8, RIJ and RIQ are each a hydrogen atom, a substituted or unsubstituted alkyl group, or a cycloalkyl group. group, alkenyl group, aryl group,
Benzyl group or aralkyl group, RXRXR and Rlg are each a hydrogen atom, a halogen atom, a hydroxyl group,
Substituted or unsubstituted alkyl group, cycloalkyl group,
Alkenyl group, aryl group, aralkyl group, alkoxy group, amino group, alkylamino group or arylamino group, Hll and R12 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, a cycloalkyl group , an alkenyl group, a Schifftetraalkenyl group, an oryl group, or an aralkyl group (however, R11 and R1!: may jointly form a saturated or unsaturated hydrocarbon ring having 3 to 1 carbon atoms) )〕