JPS6046561A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain an electrophotographic sensitive body superior in electrostatic chargeability characteristics, sensitivity, durability, etc., by incorporating a specified bisazo compd. in a photosensitive layer as a carrier generating substance and combining it with one selected from carrier transfer substances in a wide range. CONSTITUTION:A photosensitive body superior in heat and humidity resistance, etc., too is obtained by forming a photosensitive layer obtained by incorporating a compd. as a carrier generating substance together with a carrier transfer substance in one photosensitive layer or especially forming a laminate type photosensitive layer composed of a carrier transfer layer and a carrier generating layer contg. said compd. represented by formula I in which Y1, Y2 are each H, halogen, CN, alkyl, or alkoxy; A is one of groups represented by formulae II-V; Z is an atomic group necessary to form an optionally substd. aromatic C ring or aromatic hetero ring; Q is optionally substd. carbamoyl or sulfamoyl; R1 is H, optionally substd. alkyl or amino or carbamoyl, COOH, its ester, or CN; and R2, R3 are each optionally substd. alkyl or aralkyl or aryl.

Description

[Detailed description of the invention]

(Industrial Application Field) The present invention relates to a photoreceptor, and more particularly to a novel electrophotographic photoreceptor having a photosensitive layer containing a bisazo compound. (Prior Art) Conventionally, inorganic photoreceptors having a photosensitive layer containing an inorganic photoconductive compound such as selenium, zinc oxide, or cadmium sulfide as a main component have been widely used as electrophotographic photoreceptors. However, these are not necessarily satisfactory in terms of sensitivity, thermal stability, ij humidity, unidirectionality, etc. For example, when selenium crystallizes, its properties as a photoreceptor deteriorate, which has implications for manufacturing.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as a photoreceptor deteriorates. cormorant. Additionally, cadmium sulfide has problems in moisture resistance and durability, and zinc oxide has problems in durability. In order to overcome these drawbacks of inorganic photoreceptors, research and development have been actively conducted in recent years on organic photoreceptors having photosensitive JU containing various organic photoconductive compounds as main components. For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor having a photosensitive layer containing poly-N-vinylcarbazole and 2,4,7-)nitro-9-fluorenone. However, (7) this photoreceptor is not necessarily satisfactory in terms of sensitivity and durability. Attempts have been made to develop electrophotographic photoreceptors of the so-called functionally separated type, in which each material can be selected from a wide range, making it relatively easy to create a photoreceptor with desired performance. A lot of research has been done because it is possible to create such a functionally separated electrophotographic photoreceptor.
Many compounds have been proposed as carrier-generating substances. Examples of using an inorganic compound as a carrier generating substance and [7] include amorphous selenium described in Japanese Patent Publication No. 43-16198, which is used in combination with an organic photoconductive compound. The drawback that the carrier generation layer made of amorphous selenium crystallizes due to heat and deteriorates the characteristics as a photoreceptor has not been improved. Furthermore, many electrophotographic photoreceptors using organic dyes or organic pigments as carrier-generating substances have been proposed. For example, as an electrophotographic photoreceptor containing a bisazo compound or a trisazo compound in the photosensitive layer, JP-A No. 54-22834, JP-A No. 56-143437, JP-A-57-
Publication No. 138646, Japanese Patent Application Publication No. 57-176055 W
The i-stop is already known. However, these bisazo compounds or trisazo compounds are not necessarily satisfactory in terms of sensitivity, residual potential, or stability during repeated use, and the selection range of carrier transport substances is also limited. It does not fully satisfy the wide range of process requirements. In recent years, Ar laser, He −
Gas lasers such as Ne lasers and semiconductor lasers are beginning to be used. These lasers are characterized by their ability to perform 0N10FF in time series, and semiconductor lasers are considered particularly promising as light sources for copiers with image processing functions, such as intelligent copiers, and printers for computer output. is attracting attention because it does not require an electric signal/optical signal conversion element such as a tone-changing optical transducer and can be made smaller and lighter. However, this cow conductor -+71- has a low output compared to a gas laser RC, and the oscillation wavelength is also long (approximately 780 am or more). As it is, it is impossible to use it as a photoreceptor using a semiconductor laser as a light source. (Objective of the Invention) The object of the present invention is to provide a photoreceptor that is stable against heat and light and has an excellent carrier generation ability. An object of the present invention is to provide a photoreceptor containing a specific bisazo compound. Another object of the present invention is to provide high sensitivity, low residual potential, and characteristics that can be used repeatedly. - To provide an electrophotographic photoreceptor with excellent durability that does not change - 4. Another object of the present invention is to act as an effective bisazo-f!-generating substance even in combination with a wide range of carrier transport substances. 8) Provides a K photoreceptor containing a compound containing -C, also known as T stone. Still another object of the present invention is to provide a photoreceptor that has a sufficiently high IJ rating for a long wavelength light source such as a semiconductor laser. Invention) Still other purposes (1, (q l”d 'jJ
'g'σ,)! jj listing h) will also become clear. In order to achieve the above object, the present inventor has made the following general formula [I] as shown in 11. We have completed the invention by discovering that a bisazo compound that binds to the photoreceptor acts as an active ingredient. General formula CI) [wherein, Yl and Y! ：Hydrogen atom, )・Rogen atom, cyano group, alkyl group or alkoxy group)
, 1. C; --〇〇8 A: 11 and 1 R4: Hydrogen atom, substituted/unsubstituted alkyl group having 1 to 4 carbon atoms, substituted/unsubstituted γ-A/kyl group, substituted/unsubstituted Substituted phenyl group, l<,: hydrogen atom, substituted/unsubstituted alkyl group having 1 to 4 carbon atoms, substituted O unsubstituted aromatic carbon ring group (e.g. substituted/unsubstituted alkyl group)
unsubstituted phenyl group, substituted/unsubstituted naphthyl group, substituted/unsubstituted anthryl group, etc.), or substituted/unsubstituted aromatic double hydrocyclic group (for example, M-substituted/unsubstituted carbazolyl group, Represents a substituted or unsubstituted dibenzofuryl group. Substituents for these groups include, for example, carbon 5!18 number 1~
Substituted/unsubstituted alkyl groups (e.g., methyl group, ethyl group, inpropyl group, tertiary butyl group, trifluoronotyl group), substituted/unsubstituted 7-ralkyl groups (e.g., benzyl group, phenethyl group) ), halogen atoms (chlorine atom, odor atom, fluorine atom, iodine atom), substituted/unsubstituted alkoxy groups having 1 to 4 carbon atoms (e.g. methoxy group, ethoxy group, isochloroboxy group, tertiary butoxy group, 2 -chloroethoxy me), hydroxy group, substituted/unsubstituted γ-lyloxy group (e.g., p-chlorophenoxy group, 1-su7toxy group, etc.), acyloxy group, (e.g., acetyloxy group, p-cyanobenzoyl group, etc.), oxy group), carboxy group, its ester group (e.g., ethoxycarbonyl group, m-promophenoxycarbonyl group, etc.), carbamoyl group (e.g., γminocarbonyl & 3M butylaminocarbonyl group, anilinocarbonyl group) , acyl group (
For example, ahythyl'IL O-nitrobenzoyl group, etc.)
, sulfo group, sulfamoyl group (e.g., ryominosulfonyl g, 3+ butylaminosulfonated Ms p-tolylaminosulfonyl Me), amino group, acylamino group (e.g., acetylamino group, benzoylamino group, etc.)
, a sulfonamide group (for example, a methanesulfonamide group, a p-toluenesulfonamide group), a cyano group, and a nitro group, but preferably a substituted or unsubstituted argyl group having 1 to 4 carbon atoms. (
For example, methyl group, ethyl group, isopropyl group, n-butyl, trifluoromethyl group →), halogen atom (salt 3
1c atom, bromine atom, fluorine atom, iodine atom), carbon number 1
-4 substituted/unsubstituted alkoxy groups (files include methoxy group, ethoxy group, tertiary butoxy group, 2-chloroethoxy group), cyano group, and nido group. 2 is an atomic group necessary to form a substituted/unsubstituted aromatic carbocycle or a substituted/unsubstituted aromatic heterocycle,
Specifically, it represents, for example, an atomic group forming a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted indole ring, or a substituted or unsubstituted carbazole ring. Examples of substituents for the atomic group forming these rings include a series of substituents such as those listed as substituents for R4+R1, but preferably halogen atoms (chlorine atoms,
bromine atom, iodine atom, fluorine atom). Sulfo group, sulfamoyl group (eg, aminosulfonyl g, p-)lylaminosulfonyl & etc.). R3 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or
Unsubstituted amino groups, carboxy groups, ester groups thereof, substituted/unsubstituted carbamoyl groups, and cyano groups, preferably hydrogen atoms, substituted/unsubstituted alkyl groups having 1 to 4 carbon atoms (e.g., methyl group, ethyl group) group, isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), and cyano group. A' is a substituted or unsubstituted aryl group, preferably M
For example, a series of Mi groups such as M are listed as substituents for R41us, but it is preferable that chlorine atom, bromine atom, fluorine atom, iodine atom), substituted/unsubstituted alkyl groups having 1 to 4 carbon atoms (e.g., methyl group, ethyl group, isopropyl &, 3Aff butyl group, trifluoromethyl group, etc.), A substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms (for example, a methoxy group, an ethoxy group, an isoproboxy group, a 3-rusibutoxy group, a 2-chloroethoxy group). Rt and R8 are substituted/unsubstituted alkyl groups, substituted/unsubstituted aralkyl groups, and [i!・Represents an unsubstituted aryl group, preferably an M-substituted/unsubstituted alkyl group having 1 to 4 carbon atoms (for example, %J4-km, ethyl group, isopropyl group, tertiary butyl group, trifluoromethyl21!
), substituted/unsubstituted phenyl groups (e.g., phenyl group, p-methoxy7xyl group, l'+1-chlorophenyl & etc.). (Effects of the Invention) That is, in the present invention, by using a bisazo compound represented by the general formula CI) as a photoconductive substance constituting the photosensitive layer of a photoreceptor, heat and light, which are the objects of the present invention, can be reduced. Furthermore, it has excellent electrophotographic properties such as charge retention, sensitivity, and residual potential, and has little fatigue deterioration even after repeated use.
An excellent photoreceptor having sufficient sensitivity even in the wavelength range of 0 nm or more can be produced. (Structure-2 of the Invention) Among the bisazo compounds represented by the general formula C1, IItJ used in the present invention, preferred are the atomic groups represented by the following general formula (II) and [111]. General formula ([] [In the formula, A, Yi, and Y are the same as the general formula [■].]
General formula] [In the formula, A, Y, and Y are the same as in general formula (I). ]
Specific examples of bisazo compounds useful in the present invention shown in the general formula CI)-Ikkancho include those having the following structural formula, but the bisazo compounds of the present invention are limited by this K. It's not a thing. A-(1) to (38) 1.

[Nakajiro-21'' The above bisazo compounds can be easily synthesized by known methods. . Synthesis Example 1 (Synthesis of Exemplified Compound A-(39)) First, an outline of the synthetic red route is shown below. The bisazo compound of the present invention has excellent photoconductivity, and when an electrophotographic photoreceptor is manufactured using the same, a photosensitive layer in which the bisazo compound of the present invention is dispersed in a binder is formed on a conductive support. It can be manufactured by providing. Another method is to use the bisazo compound of the present invention as a carrier-generating substance that takes advantage of its particularly excellent carrier-generating ability among its photoconductivity, and to use it together with a carrier-transporting substance that can effectively act in combination with this. It is also possible to use a so-called functionally separated electrophotographic photoreceptor, such as a laminated type or a distributed type. Furthermore, the bisazo compound used in the present invention can be used alone or in combination of two or more of the bisazo compounds represented by the general formula (1), or may be used in combination with other bisazo compounds. . Various mechanical configurations of electrophotographic photoreceptors are known, and the electrophotographic photoreceptor of the present invention can take any of these forms. Usually, the configuration is as shown in FIGS. 1 to 6. 1 and 3, a photosensitive layer 4 consisting of a laminate with a carrier transport layer 3 containing the above-mentioned bicarrier transport substance as a main component is provided on a conductive support 1. In FIGS. As shown in FIGS. 2 and 4, this photosensitive layer 4 may be provided via an intermediate layer 5 provided on a conductive support. When the photosensitive layer 4 has a two-layer structure in this manner, an electrophotographic photoreceptor having the most excellent electrophotographic properties can be obtained. Further, in the present invention, as shown in FIGS. 5 and 6, a photosensitive layer 4 comprising the carrier-generating substance 7 dispersed in a layer 6 mainly composed of a carrier-transporting substance is provided on the conductive support 1. It may be provided directly or via the intermediate layer 5. When the bisfuji compound of the present invention is used as a noon spear 7 generating substance, the carrier transporting substance used in combination with the bisfuji compound may include electron-donating substances that easily transport electrons such as trinitrofluorenone or tetranido-negative fluorenone, as well as poly-N - Polymers having 5 heterocyclic compounds in their side chains, such as vinylcarbazole, triazole derivatives, dipsol conductors, imidazole derivatives, pyrazoline derivatives, polyarylalkane derivatives, phenylenediamine derivatives, hydrazone derivatives, amino Examples of electron-donating substances that easily transport holes include substituted carfun derivatives, triarylamine derivatives, carbazole derivatives, and stilbene derivatives, but the carrier transporting substances used in the present invention are not limited to these. The carrier generation layer 2 constituting the two-layered photosensitive layer 4 is formed directly on the conductive support 1 or the carrier transport layer 3, or after providing an intermediate layer such as an adhesive layer or a single barrier layer as necessary. For example, it can be formed by the following method. M-1) A method of applying a solution in which a bisazo compound is dissolved in a suitable solvent, or a solution in which a binder is added and mixed as necessary. M-2) A method in which a bisazo compound is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., and a binder is added as necessary to mix and disperse the resulting dispersion and then applied. Solvents or dispersion media used to form the carrier generation layer include u, n-butylamine, diethylamine, ethylene diamine, inpropamine, triethanolamine, triethylene diamine, N, N-dimethylformamide, a7tone, and methyl ethyl ketone. , cyclohexanone, benzene, toluene, xylene, chloroform, 1,2-dichloromethane, dichloromethane, tetrahydrofuran, dioxane, methanol, ethanol, impropatol, ethyl acetate, butyl acetate, dimethyl sulfoxide and the like. When using a binder in the carrier generation layer or the carrier transport layer, any binder can be used, but it is preferable to use a film-forming polymer that is hydrophobic and has a high dielectric constant (or an electrically insulating film-forming polymer). Preferred. Examples of such high molecular weight polymers include the following:
It is not limited to these. P-1) Polycarbonate p-2) TF: Polyester P-8) Methacrylic resin P-4) Acrylic resin P-5) Polyvinyl chloride P-6) Polyvinylidene chloride P-7) Polystyrene P-8) Polyvinyl Acetate p-9) Styrene-butadiene copolymer p-1o)
[Vinylidene chloride-acrylonitrile copolymer P-11) Vinyl chloride-vinyl acetate copolymer P-12
) Vinyl chloride-vinyl acetate-maleic anhydride copolymer P-1:3) Silicone resin P-14) Silicone-aloxide resin P-15) Phenol-formaldehyde resin P-16) Styrene-Alkyra F" Tree IIWP-17 ) Poly-N-vinylcarbazole These binders can be used alone or in a mixture of two or more.The thickness of the carrier generation layer 2 formed in step 5-1 above is 0.01μ. The amount is preferably 0.05 μm to 5 μm, more preferably 0.05 μm to 5 μm.In addition, when the carrier generation layer or the photosensitive layer is a dispersion system, it is preferable that the particle size of the azo compound is 5 μm or less. More preferably, it is 118 m or less.The conductive support used in the electrophotographic photoreceptor of the present invention includes a metal plate including an alloy, a metal drum, a conductive polymer, a conductive compound such as indium oxide, and an alloy. Paper that has been made conductive by coating, vapor depositing, or laminating a thin layer of metal such as aluminum, tsucladium, or gold.
Examples include plastic films. As an intermediate layer such as an adhesive layer or a barrier layer, in addition to the high molecular weight polymer used as the binder, polyvinyl alcohol,
Organic polymer substances such as ethyl cellulose and carboxymethyl cellulose, aluminum oxide, etc. are used. The electrophotographic photoreceptor of the present invention has the above five structures,
As is clear from the Examples described below, it has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, and particularly shows little deterioration due to chewing even after repeated use, and has excellent durability. Hereinafter, the present invention will be specifically explained in Examples, but the embodiments of the present invention are not limited thereto. (Example) Example 1 Exemplified compound A-(3) 2 II and polycarbonate resin [Pan 5 I] L-1250J (Hitsuiri Kasei Co., Ltd.
2 g of a) was added to 1,2-dichloroethane 11Qmtlc and dispersed in a ball mill for 12 hours. This dispersion was placed on a polyester film made of aluminum't WM.
It was coated so that the film thickness when dry was 1 tr@(C) to form a carrier generation layer, and on top of that, 1-phenyl-3-(p-diethylaminostyrylluminophenyl)pyrazoline ( Below groove a 2K -
(1) ) f3'9 'y' Polycarbonate resin "Panlite IJ'-125o" rO9 Tora 1, 2
-') A solution dissolved in lithium oxide tan 11ornt was coated so that the film thickness after drying was ]5/# (to form a carrier transport layer, and an electrophotographic photoreceptor of the present invention was prepared. K-(1) The photoreceptor obtained as described above was subjected to the following temporal evaluation using an electrostatic paper tester manufactured by Nichidenki Seisakusho SP-428. After being charged for 5 seconds,
The exposure amount required to attenuate the surface potential by half by leaving it in the dark for 5 seconds and then irradiating it with halogen lamp light so that the illuminance on the photoreceptor surface is 351 degrees (half-reduction exposure amount) E
I scored 3A. Further, the surface potential (residual potential) VB after exposure with an exposure amount of 301 ux-sea was measured. Furthermore, the same measurement was repeated 100 times. The results are shown in Table 1. Table 1 Comparative Example 1 The following bisazo compound G-(1) was used as a carrier generating substance.
A comparative photoreceptor was prepared in the same manner as in Example 1, except that . G-(1) Regarding this comparative electrophotographic photoreceptor, measurements were performed in the same manner as in Example 1, and the results shown in Table 2 were obtained. As is clear from the results in Table 2 and above, the electrophotographic photoreceptor of the present invention is extremely superior in sensitivity, residual potential, and repetition stability compared to the comparative electrophotographic photoreceptor. Example 2-4 Exemplary compounds A-(4), A-(
5) and A-(10), and 6-methyl-1-(1-ethyl-4-carbazolyl)methylideneamino-1,2°3.4-tetrahydroquinoline (the following compound) was used as the carrier transport substance. -(2)), 4.4'
-dimethyl-4''-(4-methoxy)styryl-triphenylamine (compound K-(3) below), and 4.
47-methyl=4''-(4-chloro)-styryl-triphenylamine (using the following compound K-(41'),
An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example except for the above, and the same measurements were performed, and the results shown in Table 3 were obtained. K-(2) K-(3) K-(4) Table 3 Example 5 Vinyl chloride-vinyl acetate-maleic anhydride copolymer was placed on a conductive support made by laminating aluminum foil on a polyester film. A 0.05 μm thick intermediate layer made of S-LEC MF-10J (manufactured by Tanezu Kagaku Co., Ltd.) was provided, and exemplified compound A-(42) 2# was mixed with 110 d of 1,2-dichloroethane on top of it. A carrier generation layer was formed by dispersing the dispersion liquid in a ball mill for a while and applying it to a film thickness of 0.5 μm after drying. →-4
6Ii and methacrylic resin "Acrivet" (manufactured by Mitsubishi Reimin Co., Ltd.)] Og in L2-dichloroethane 70 ttr
A carrier transporting layer was formed by coating a solution dissolved in 6 and having a thickness of 10 μm after drying, thereby producing an electrophotographic photoreceptor of the present invention. The same measurements as in Example 1 were performed on this electrophotographic photoreceptor, and the first measurement was 8%-211ux *
The results were obtained: eac+, VRe=O+V. Example 6 Example 7 A carrier generation layer was formed in the same manner as in Example 5 except that Exemplified Compound A-(42) was replaced with Exemplified Compound A-(43). On top of this, 4-methoxy-4'-styryl-triphenylamine (
To the compound - (6)) 611 and polycarbonate "Panlite L-1250J (manufactured by Jyojin Kasei Co., Ltd.) 1oIlt,
After drying a solution dissolved in 70mj of 1.2-dichromitane, a carrier transport layer was formed by applying the solution to a thickness of 10 μm to prepare an electrophotographic photoreceptor of the present invention. Regarding this electrophotographic photoreceptor, foot measurement was performed in the same manner as in Example 1, and B54 = 2.5 lux"" a
ee and VR = OIV. Example 8 A 0.0-thick film made of vinyl chloride-vinyl acetate-maleic anhydride copolymer "Eslec MF-10J (manufactured by Tanezu Kagaku Co., Ltd.)" was coated on the surface of an aluminum drum with a diameter of 100i+x.
An intermediate layer of 5 μm was provided, and the exemplified compound Toshihito-(3-
+) 4P to 1.2-di(> o mouth: c # n4QQ
A dispersion liquid was mixed with Inj K and dispersed for a while using a pole separation machine, and then applied to a film thickness of 0.6 μm after drying to form a carrier generation layer. Furthermore, on top of this, 4,4'-dimethyl-4"-(4-methoxy)styryl-triphenylamine (the following compound K
-(6)) 30 g and polycarbonate resin "Corbilon 5-i000J (manufactured by Mitsubishi Gas Chemical Co., Ltd.) 5op
was dissolved in 400 vLt of 1,2-dichloroethane K-(6) and coated to form a carrier transport layer so as to have a film thickness of 13 μm after drying, thereby producing a drum-shaped electrophotographic photoreceptor. The photoreceptor produced in this way was used in an electrophotographic copying machine [υ−
When it was attached to a modified Blx V2J (manufactured by Konishiroku Photo Industry Co., Ltd.) and a face image was copied, a copy image with high contrast and clarity that was faithful to the original image was obtained. Also, this will change even if you tighten it 9 times 10,060 times.
There was no fi. Comparative Example 3 A drum-shaped comparative photoreceptor was prepared in the same manner as in Example 8, except that the exemplified compound A-(34) was replaced with a trisazo compound (G-(31)) represented by the following structural formula. When the copied images were evaluated in the same manner as in Example 8, only images with many capri were obtained.
When copying is repeated (accordingly, the contrast of the copied image decreases, and after 2000 repetitions, it is almost impossible to obtain a copied image.) Example 9 Laminating aluminum column foil on polyester film J2 !-1, vinyl chloride-vinyl acetate-maleic anhydride copolymer "Eslenc MP-1"
0J (manufactured by Suikagaku Co., Ltd.) with a thickness of o, og μm was provided, and on top of that, 5 g of Exemplified Compound A-(9) and 3.3 g of polycarbonate resin "Panlite L-1250J (manufactured by Banjin Kasei Co., Ltd.) was added to 100 i of dichloromethane and dispersed in a ball mill for U time to form an electrophotographic photoreceptor. E3A and VR were measured in the same manner as in Example 1 except that the voltage was changed to +6 KV.The first result was E% = 3.8 lux・See and VR = +25 V. Example 30 Vapor deposition of aluminum 4-methyl-4'-styryl-triphenylamine 4・-→-shiki→zifu-' g was dissolved in 70 g of 1,2-dichloroethane (IC), and this solution was coated to give a film thickness of 10 to 11 m after drying. Next, to this 5 L, 1 l of the exemplified compound Tomohito-(41) was applied. and A-
(47) II/ and 1,2 to Zik bb: f. /n110
The electrophotographic photoreceptor of the present invention was prepared by mixing the carrier-generating layer with a carrier-generating layer and forming a carrier-generating layer by applying a dispersion liquid that was mixed with the carrier-generating layer and dispersed in a ball mill for a while using a ball mill so that the film thickness after drying was 0.5 μm. The thus obtained photoreceptor was evaluated in the same manner as in Example 9, and found that E% = 3.4]ux-sec and ■R = +15v. Example 11 A 2% ethylenediamine solution of Exemplified Compound A-(2) was
A carrier generation layer was formed by coating onto a polyester film laminated with aluminum so that the dry film thickness was 05 μm. Furthermore, as a carrier transport layer, 1-[4-(N.N-di(p-)lyl)amine)benzylidene-aminocoindoline (for the following compound.
(N,N-diethylamino)benzaldehyde-1,1
-diphenylhydrazone (compound K below - (8)
), also +a 3. 3; 4-Trimethyl-triphenylamino (the following compound K-tqt) was separately added to about 10 9 and polycarbonate K-(7) K-(8) resin (manufactured by Konjin Kasei Co., Ltd., Panlite L-12so) 1
A solution of 41 dissolved in 1,2-dichloroethane i40 M was mixed with I/C so that the dry film thickness was 12 μm and dried to obtain photoreceptors with different 8 kinds of γ-transport substances. Ta. These three types of photoreceptors are each made by Kawaguchi Electric Seisakusho SP.
The following characteristics were evaluated using a -428 type electrostatic paper tester. After charging with a charging voltage of -6KV for 5 seconds and leaving it in the dark for 5 seconds, halogen light was applied to the material surface at an illuminance of 351ux.
The exposure amount required to attenuate the surface potential by half (half-reduced exposure amount, By6) was measured. Further, the surface potential (residual potential) VR after exposure with an exposure amount of 301 ux-IIec was measured. As shown in Table 5, the results were good in combination with any carrier transport substance. Table 6 Comparative Example 4 Illustrated Compound Shijin-(2) was converted into the following bisazo compound (a-
(4)) A comparison photoreceptor was prepared in the same manner as in Example 11 except that the VC was replaced, and as a result of characteristic evaluation, G-
(43 As shown in Table 6, results varied depending on the carrier transport substance. Table 6 Examples) 2 On the conductive support provided with the intermediate layer used in Example 5 ((,
Exemplary compound A-(40:) 2.9 and 100 M of 1,2-dichloroethane were well dispersed and mixed, and the film thickness after drying was 0.
A carrier generation layer was prepared by coating 3 μTrLK Naruyo 5. 1-(1-phenyl-4-rubazolyl)methylideneamino-1,2 is then added thereon as a carrier transport substance.
, 3,4-tetrahydroquinoline (compound K' below)
(10')) 6 g and polycarbonate [Panlite L-1250J (manufactured by Kinjin Kasei Co., Ltd.) K-(JO) 109 were dissolved in 90.11 VC of 1,2-dichloroethane, and the film thickness after drying was 107177 t. An electrophotographic photoreceptor of the present invention was prepared by applying Ic (() to form a carrier transport layer.

[The electrophotographic properties at τ were measured in the same manner as in Example 7. The results are shown in Table 7. As is clear from the results in Table 7 and above, the electrophotographic photoreceptor of the present invention has good sensitivity and residual potential characteristics even at high temperatures;
It is stable against heat, and you can tell when it is moving. Example 13 2 g of Exemplary Compound A-(46) and 11 1,2-dichloroethane were placed on the conductive support provided with the intermediate layer used in Example 5.
The film thickness after drying is 0.3/1m after being well dispersed and mixed.
A carrier generation layer was created by applying the following coating to form a carrier generation layer. Regarding this chitria generation layer, place a super high mercury wrap (manufactured by Tokyo Shibaura' Junkaba Co., Ltd.) 30 minutes away, and
UV light was irradiated for 1 min. Next, 4-methoxy-4'-(4-
Chlor)-styryl-triphenylamine (for the following compound-(11)) 71 and polycarbonate [Panlite L
-1250] (manufactured by Teidai Kasei Co., Ltd. 101/ and 1.2
-Dichloroethane K-(11) 1909 was dissolved in 51C to form a carrier transport layer, and the electrophotographic photoreceptor of the present invention was prepared. The same measurements as in Example 5 were performed on this electrophotographic photoreceptor. The results are shown in Table 8 ◇Example] 4 After formation of the carrier generation layer ((except that υV light was not irradiated,
Example] An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 3, and the same measurements as in Example 5 were carried out. The results are shown in Table 8. As is clear from the results shown in the tsB table, the electrophotographic photoreceptor of the present invention has excellent sensitivity and residual potential characteristics to UV light irradiation, has small fluctuations in acceptance potential, and is stable against light. It can be understood. Comparative Example 5 Compound A-(46) was converted into the following bisazo compound (C-0G
-, (5) (An electrophotographic photoreceptor was prepared in the same manner, and the same measurements as in Example 5 were performed. The results are shown in Table 9. As is clear from the results in Table 9, the above compound When exposed to UV light, the sensitivity and residual potential characteristics of the electrophotographic photoreceptor produced using the photoreceptor deteriorated, and the amount of variation in acceptance potential was large.Example] 4 In Example 5, exemplary compound A C-(42) was replaced with −
A drum-shaped electrophotographic photoreceptor was produced in the same manner except that (1) was replaced. The spectral Δε degree of this photoreceptor at 790 nm was 113 thJ/crJ (half exposure amount). The photoreceptor of the present invention is used as a semiconductor laser (790 nm) with a laser beam intensity of 0.85 mW on the surface of the photoreceptor.
A live-action test was conducted using an experimental machine equipped with After the surface of the photoreceptor was charged with a voltage of 15 KVIC, it was exposed to laser light and subjected to reversal development at a bias voltage of 1250 VIC, and a good image without fog was obtained. Comparative Example 6 A comparative photoreceptor was obtained in the same manner as in Example 14, except that the following comparative bisazo compound was used in place of Exemplified Compound A-35. The spectral sensitivity of this photoreceptor at 790 nm is 31μ.
J/ctlc half-exposure. Using this comparative photoreceptor, a photo-taking test using a semiconductor laser was conducted in the same manner as in Example 14, but there was a lot of fog and good images could not be obtained. As is clear from the results of the above Examples and Comparative Examples, the electrophotographic photoreceptor of the present invention has better characteristics such as stability, sensitivity, durability, and combination with a wide range of carrier transport substances than the comparative electrophotographic photoreceptor. It is extremely excellent.

[Brief explanation of drawings]

1 to 6 are sectional views showing examples of the mechanical structure of the electrophotographic photoreceptor of the present invention, and 1 to 7 in the figures represent the following, respectively. Process: conductive support, 2: carrier generation layer, 3:
... carrier transport layer, 4 ... photosensitive layer, 5 ... intermediate layer, 6 ... scrap containing carrier transport substance, 7 ...
Carrier generating substances. Agent Yoshimi Kuwahara

Claims (2)

[Claims] (1) An electrophotographic photoreceptor comprising a photosensitive layer containing a bisazo compound represented by the following general formula [■] on a conductive support. General formula CI) [In the formula, Yl and Y: a group selected from a hydrogen atom, a halogen atom, a cyano group, an alkyl group, or an alkoxy group, 0 and 2: a substituted/unsubstituted aromatic carbocycle or Atom group necessary to constitute a substituted/unsubstituted aromatic carbocycle, Q: unsubstituted carbamoyl group or substituted/unsubstituted sulfamoyl group, RI: hydrogen atom, substituted/unsubstituted alkyl group, During substitution, unsubstituted amino group, substituted/unsubstituted carbamoyl group, carboxy group and its ester group, or cyano group, A': ffi-substituted/unsubstituted aryl group, R1 and R1
: Represents a substituted/unsubstituted argyl group, a substituted/unsubstituted aralkyl group, or a substituted/unsubstituted aryl group. ] (2) The photosensitive layer contains a carrier transporting substance and a carrier generating substance, and the carrier generating substance has the general formula [
The electrophotographic photoreceptor according to claim 1, which is a bisazo compound represented by [i].