JPS6046560A - 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 in combination with one selected from carrier transfer substances in a wide range. CONSTITUTION:A photosensitive body superior in heat and humidity resistance, etc. 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 have poor sensitivity, thermal stability, and It is not always satisfactory in terms of moisture resistance, j resistance, etc. For example, when selenium crystallizes, its properties as a photoreceptor deteriorate, making it difficult to manufacture.Also, selenium crystallizes due to heat, fingerprints, etc., and its performance as a photoreceptor deteriorates. Cadmium sulfide also has moisture resistance, durability,
Even zinc oxide has problems with durability, etc. In order to overcome these drawbacks of inorganic photoreceptors, research and development have been actively conducted in recent years on organic photoreceptors having photosensitive layers containing various organic photoconductive compounds as main components. For example, Japanese Patent Publication No. 5T)-10496 describes an organic photoreceptor having a photosensitive layer containing N-vinylcarbazole and 2.4.7-)nitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in terms of sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with higher performance by assigning the carrier generation function and the carrier transport function to different substances. Many studies have been conducted on such so-called function-separated electrophotographic photoreceptors because each material can be selected from a wide range and a photoreceptor with arbitrary performance can be produced relatively easily. I got it. Many compounds have been proposed as carrier generating substances for such functionally separated electrophotographic photoreceptors. An example of using an inorganic compound as a carrier generating substance is amorphous selenium, which is 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 consisting of the above 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-54-22834, JP-A-56-143437, JP-A-55-
No. 93157, Japanese Unexamined Patent Publication No. 196241/1987, etc. are well known. However, these bisazo compounds or trisazo compounds have poor sensitivity, residual potential, or
The properties of stability during repeated use are not necessarily satisfactory, and the selection range of carrier transporting substances is also limited, so that they do not fully satisfy the wide demands of electrophotographic processes. Furthermore, 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 being capable of 0N10FF in time series, and are particularly promising as light sources for copiers and computer output printers that have image processing functions, including intelligent copiers. Among these, semiconductor lasers are attracting attention because their nature does not require an electrical signal/optical signal conversion element such as an acousto-optic element, and because they can be made smaller and lighter. However, this semiconductor laser has a low output compared to a gas laser, and the oscillation wavelength is also long (approximately 780 nm or more), so the spectral sensitivity of conventional photoreceptors is too high on the short wavelength side. It is impossible to use it as a photoreceptor using a semiconductor laser as a light source. (Objective of the Invention) An object of the present invention is to provide a photoreceptor containing a specific bisazo compound that is stable to heat and light and has excellent carrier generation ability. Another object of the present invention is to provide an electrophotographic photoreceptor with high sensitivity, low residual potential, and excellent durability whose characteristics do not change even after repeated use. Still another object of the present invention is to provide an electrophotographic photoreceptor containing a bisazo compound that can effectively act as a carrier generating substance even in combination with a wide variety of carrier transporting substances. Still another object of the present invention is to provide a photoreceptor having sufficient practical sensitivity even to long wavelength light sources such as semiconductor lasers. Still other objects of the present invention will become apparent from the description in the specification. As a result of extensive research to achieve the above object, the present inventors discovered that a bisazo compound represented by the following general formula CI) can function as an active ingredient of a photoreceptor, and have completed the present invention. It is. Hereinafter, Y and Y2: hydrogen atom, cyano group, halogen atom,
a group selected from an alkyl group or an alkoxy group, hereinafter) white01'i, R4: a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aralkyl group, Substituted/unsubstituted phenyl group, R3: hydrogen atom, substituted/unsubstituted alkyl group having 1 to 4 carbon atoms, substituted/unsubstituted aromatic carbocyclic group (e.g. substituted O unsubstituted zz-nyl group, substituted/unsubstituted zz-nyl group, Unsubstituted naphthyl group, substituted and
represents a substituted or unsubstituted aromatic heterocyclic group (for example, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuryl group, etc.). Substituents for these groups include, for example, substituted/unsubstituted alkyl groups having 1 to 4 carbon atoms (e.g., methyl group, ethyl group,
isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), substituted/unsubstituted aralkyl group (e.g. benzyl group, phenethyl group, etc.), halogen atom (chlorine atom, bromine atom, fluorine atom, iodine atom), carbon Substituted/unsubstituted alkoxy groups of numbers 1 to 4 (e.g. methoxy group, ethoxy group,
(impropoxy group, tertiary butoxy group, 2-chloroethoxy group, etc.), hydroxy group, substituted/unsubstituted aryloxy group (e.g., p-lylphenoxy group, 1-naphthoxy group, etc.), acyloxy group, (e.g. c, acetyloxy group, p-cyanobenzoyloxy group, etc.),
Carboxy groups, ester groups thereof (e.g., ethoxycarbonyl group, m-promophenoxycarbonyl group, etc.), carbamoyl groups (e.g., aminocarbonyl group, tertiary butylaminocarbonyl group, anilinocarbonyl group, etc.), acyl groups (e.g., acetyl group, 0-nitrobenzoyl group, etc.), sulfo group, sulfamoyl group (e.g., aminesulfonyl group, tertiary butylaminosulfonyl group, p-tolylaminosulfonyl group, etc.), amino group, acylamino group (
For example, acetylamino group, benzoylamino group, etc.)
Nurphonamide groups (e.g., methanesulfonamide group, p-)luenesulfonamide group, etc.), cyano groups, nitro groups, etc., but preferably substituted O-unsubstituted alkyl groups having 1 to 4 carbon atoms (e.g., Methyl group, ethyl group, isopropyl group, n-butyl,
trifluoromethyl group, etc.), halogen atom (chlorine atom,
bromine atom, fluorine atom, iodine atom), substituted/unsubstituted alkoxy groups having 1 to 4 carbon atoms (e.g., methoxy group, ethoxy group, tertiary butoxy group, 2-chloroethoxy group, etc.), cyano group, di) o It is the basis. Z is an atomic group necessary to form a substituted/unsubstituted aromatic carbocycle or a substituted/unsubstituted aromatic heterocycle,
Specifically, it represents an atomic group forming a substituted/unsubstituted benzene ring, a substituted/unsubstituted naphthalene ring, a substituted/unsubstituted indole ring, a substituted/unsubstituted carbazole ring, etc. Examples of substituents for the atomic group forming these rings include a series of substituents such as those listed as substituents for R4+R5, but preferably chlorine atoms (chlorine atoms, bromine atoms, iodine atoms) atom, fluorine atom). sulfo group, sulfamoyl group (eg, aminesulfonyl group, p-)lylaminosulfonyl group, etc.'). R1 is a hydrogen atom, a substituted O 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.), cyan group. A' is a substituted or unsubstituted aryl group, preferably C is a substituted or unsubstituted phenyl group, and the substituents for these groups include a series of substituents such as those listed as substituents for R4+R5. However, preferably a halogen atom (chlorine atom, bromine atom, fluorine atom, iodine atom), carbon number 1-4
Substituted/unsubstituted alkyl groups (e.g., methyl group, ethyl group, isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), substituted/unsubstituted alkoxy groups having 1 to 4 carbon atoms (e.g., methoxy group) , ethoxy group, isopropoxy group, tertiary butoxy group, 2-chloroethoxy group). R2 and R3 represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms (for example, methyl group, -ethyl group, isopropyl group, tertiary butyl group, trifluoromethyl group, etc.), substituted/unsubstituted phenyl group (e.g. phenyl group, p-methoxyphenyl group, m-chlorophenyl group, etc.) . (Effects of the Invention) That is, in the present invention, by using the bisazotized metal represented by the general formula [I] as a photoconductive substance constituting the photosensitive layer of the photoreceptor, heat and It is stable against light, 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 a wavelength range of 0 nm or more can be produced. (Structure-2 of the Invention) Among the bisazo compounds represented by the general formula CI) used in the present invention, the following atomic groups are preferred. General formula [■] [In the formula, A, Y, and Y2 are the same as in the general formula CD. [General formula ■] 0 [In the formula, A + YH and Y2 are the same as in the general formula [I]. ] Specific examples of the disazo compounds useful in the present invention represented by the above general formulas [T] to 匪 include those having the following structural formula, but the disazo compounds of the present invention are limited by this. It's not a thing. Bisazo compounds such as A-(11-(38) 0monkiokikii)- can be easily synthesized by known methods.
lvetlca cbemica acta, 14
89 1499 + 3,8-dinitro-5H-dibenzo[a, al
Exemplary compound A-(1) was synthesized using cyclohebuten-5-one as a raw material (2) in the order shown in the figure below.
] 1.4% of 3,8-diamino-5H-dibenzo[i,d]cyclohepten-5-24,li+ (0.1 mol) obtained by reducing cyclohepten-5-one with tin in hydrochloric acid.
Add it to a mixture of 1 part concentrated hydrochloric acid and 0.71 part water and disperse it.
3.8.9 (0.2 mol) of sodium nitrite in water
．． A solution of 2 g was added dropwise at 5° C. under water cooling, and after the dropwise addition was completed, the solution was stirred for 1 hour to react. After the reaction is completed, the reaction solution is
f! After filtration, 0.71% of 42% difluoric acid was added to the filtrate, and the resulting precipitate was collected by filtration, washed with water, and thoroughly dried. The obtained field is N,N-dimethylformamide 101
K was dissolved to obtain a tetrazonium salt solution to be used in the next reaction. Next, 2-hydroxy-3-(4-methoxy-2-methylphenylcarbamoyl)-henso[a]carbazole (
Naphthol AS-fliR) 79 & (0.2 mol), 60 g of triethanolamine was mixed with 10 l of N,N
- Dissolve in dimethylformamide, add dropwise the tetrazonium salt solution prepared above while cooling on ice, and add 2
The reaction mixture was stirred for hours. The crystals formed were collected by filtration, and the crystals were diluted with 10 liters of N, N + and 1° dimethylformamide.
After washing twice with 101 times of acetone, 68 g of the target bisazo compound (681 was obtained) was recorded.
Z middle. It shows an M peak at 1051 II, a -' (amide absorption) peak at ν = 1690 in the infrared spectrum, and elemental analysis shows that C = 74.17,
N-10,63 t, II = 4.45 t (calculated value is C
= 74.28 yen, 1:J = 10.661, H
= 4.41 h), it is understood that the target substance was synthesized. The bisazo compound of the present invention has excellent photoconductivity, and when an electrophotographic photoreceptor is manufactured using the bisazo compound of the present invention, the bisazo compound of the present invention is placed on a conductive support as a binder. It can be produced by providing a photosensitive layer dispersed in the bisazo compound.As another method, the bisazo compound of the present invention can be used as a carrier-generating substance utilizing particularly excellent carrier-generating ability among the photoconductivity possessed by the bisazo compound. By using it in combination with a carrier transport substance that can effectively act, it is also possible to create a so-called functionally separated type electrophotographic photoreceptor, such as a laminated type or a dispersed type.Furthermore, the bisazo compound used in the present invention The bisazo compounds represented by the general formula (1) can be used alone or in combination of two or more, or may be used in combination with other bisazo compounds.Mechanical structure of electrophotographic photoreceptor Although various forms are known, the electrophotographic photoreceptor of the present invention can take any of these forms. Usually, it is the form shown in Figs. 1 to 6. In Figs. A photosensitive layer 4 consisting of a laminate of a carrier generation layer 2 containing the above-mentioned bisazo compound as a main component and a carrier transport layer 3 containing a carrier transport substance as a main component is provided on a conductive support 1.Second. As shown in the figure and FIG. 4, this photosensitive layer 4 may be provided through an intermediate layer 5 provided on a conductive support.The best method is when the photosensitive layer 4 has a two-layer structure in this way. In the present invention, as shown in FIGS. 5 and 6, the carrier-generating substance 7 is dispersed in a layer 6 mainly composed of a carrier-transporting substance. The photosensitive layer 4 consisting of the above-mentioned photosensitive layer 4 may be provided directly on the conductive support 1 or via the intermediate layer 5. When the bisazo compound of the present invention is used as a carrier generating substance, it may be used in combination with the bisazo compound of the present invention. Examples of carrier transport substances include electron-donating substances that easily transport electrons, such as trinide-fluorenone and tetranitronefluorenoν, as well as those having heterocyclic compounds in their side chains, such as poly-N-vinylcarbazole. Holes in polymers, triazole derivatives, oxdiazole mws bodies, imidazole derivatives, hirazoline derivatives, polyarylalkane derivatives, phenylenediamine derivatives, hydrazone derivatives, amino-substituted chalcone derivatives, triarylamine derivatives, carbazole derivatives, stilbene derivatives, etc. Examples include electron-donating substances that easily transport carriers, 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 provided directly on the conductive support 1 or the carrier transport layer 3, or if necessary, an intermediate layer such as an adhesive layer or a barrier layer is provided. In addition, it can be formed, for example, by the following method. M-1) A method in which a solution of a bisazo compound dissolved in a suitable solvent is mixed and dissolved with a binder added thereto, if necessary, and then applied. M-2) Ball mill and mill the bisazo compound.
A method of applying a dispersion liquid in which the particles are mixed and dispersed in a dispersion medium by adding a binder if necessary.Used to form a carrier generation layer, as a solvent or a dispersion medium. II, n-butylamine, die'J-A/amine, ethylenediamine, impropaturamine, triethanolamine, triethylenediamine, N, N-
Dimethylformamide, acetone, methyl ethyl ketone, cyclohexanone, benzene, toluene, xylene, chloroform, 1,2-dichloroethane, dichloromethane, tetrahydrofuran, dioxane, methanol,
Ethanol, Impropatol, ethyl acetate, butyl acetate, dimethyl sulfoxide, etc. When using a binder in the carrier generation layer or carrier transport layer, any binder can be used, but it is preferable to use a film-forming polymer that is hydrophobic, has a high dielectric constant, and is electrically insulating. is preferred. Examples of such high molecular weight polymers include the following:
It is not limited to these. P-1) Polycarbo specialist P-2) Polynisful p-a) 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-1t) Vinyl chloride-vinyl acetate copolymer P-12
) Vinyl chloride-vinyl acetate-maleic anhydride copolymer P-13) Silicone resin P-14) Silicone-aloxide resin p-15) 7
Nor-formaldehyde resin P-16) Styrene-alkyd resin P-17) Poly-N-vinylcarbazole These binders can be used alone or as a mixture of 12 or more types. The thickness u of the carrier generation layer 2 formed in this way,
It is preferable that it is 0.01ti, n~20〃m,
More preferably, it is 0.05 μrIL to 5 μm. Further, when the carrier generation layer or the photosensitive layer is a dispersed type, the particle size of the azo compound is preferably 5 μm or less, more preferably 1 μm or less. The conductive support used in the electrophotographic photoreceptor of the present invention includes metal plates including alloys, metal drums, conductive polymers, conductive compounds such as indium oxide, aluminum including alloys, palladium, gold, etc. Apply a thin metal layer of
Examples include paper and plastic films that have been made conductive by vapor deposition or lamination. As an intermediate layer such as an adhesive layer or a barrier layer, organic polymer materials such as polyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, aluminum oxide, etc. are used in addition to the polymer used as the binder. The electrophotographic photoreceptor of the present invention has the above structure,
As is clear from the examples described later, K has excellent charging characteristics, sensitivity characteristics, and image forming characteristics, and especially K shows little fatigue deterioration when used repeatedly and has excellent durability. Hereinafter, the present invention will be specifically explained using Examples, but the embodiments of the present invention are not limited thereby. (Example) Example 1 Exemplary compound A-(1)2II and polycarbonate resin [
The mixture was added to 10 ml of Panlite L-1250J (manufactured by Ondai Kasei Co., Ltd.) and 1,2-dichloroethane, and dispersed in a ball mill for 12 hours. This dispersion was applied to a polyester film on which aluminum was vapor-deposited (with a film thickness of 1 when dried).
μmK Naruyo 5 was coated to form a carrier generation layer, and on top of that, 4-MK 4'-
Thousands of routes triphenylamino-ni-soio) 4 甚,
-; j-, -, l'', ~ Lee (the structural formula K -(11
) 6 g: Polycarbonate resin "Panlight
・1L-1250'' river g and 1,2-dichloroethane]
The film thickness after dry explosion of the dissolved solution was 15. −
1rrLl'c becomes 5 VCl'=A cloth-C111
Forming a pseudo-Yaria transport hl, the electron of the present invention ~j no'i,
A euphotoreceptor was created. K-(1) The photoreceptor obtained as described above was subjected to the following temporal evaluation using an electrostatic paper tester SP-428 manufactured by Nichidenki Seisakusho. After being charged for 5 seconds at a charging voltage of -6KV,
Leave it in the dark for 5 seconds, then shine R light on the surface of the photoreceptor 351u.
I irradiated the halogen lamp light at 5 to x to attenuate the surface potential to a fraction (fC required exposure ff1 (half-reduced exposure ff1) E%. Also, 11 light was applied at exposure 51 of 301 ux-sea. The subsequent surface potential (residual potential > VR) was determined.Furthermore, similar measurements were repeated 100 times.The results are shown in Table 1 ((not shown). Compound G-(1)
A comparative photoreceptor was prepared in the same manner as in Example 1 except that the photoreceptor was used. G-(1) 1, C1 Regarding this electrophotographic photoreceptor for comparison, the same as in Example 1 (
(The results shown in Table 2 were obtained when the measurements were carried out in 1). 9. Extremely excellent in sensitivity, residual potential and repetition stability. Example 2-4 Exemplified compounds A-(4) and A-( as carrier generating substances)
16) and A, -(39), respectively, as a carrier transport substance, Parley(go÷4.4'-dimethyl-4//-(4-methyl)styryl-triphenylamine (the following compound -(2+),]-(]1-ethyl-4-carbazolylmethylizonoamino-indoline (
The following compounds K -(31) and 4-methyl-4'-(
An electrophotographic photoreceptor of the present invention was prepared using 4-chloro)-styryl-triphenylamine (compound K-(41> below) and in the same manner as in Example 1, and the same measurements were performed. The results shown in Table 3 were obtained. ■ C2I (.K-(4) Table 3 Example 5 Vinyl chloride-vinyl acetate-
A 0.05 μm thick intermediate layer made of maleic anhydride copolymer [Eslec MF-10J (manufactured by Tanezu Kagaku Co., Ltd.) was provided, and exemplified compound A-(48)2# was added to 1.2-dichloroethane 11 on top of it. A carrier generation layer was formed by coating a dispersion liquid mixed with ljlc and dispersed for u hours at S<-lumil so that the film thickness after drying was 0.5 μm IC. '. 4-Trimethyl-triphenyl resin "Acripet" (manufactured by Mitsubishi Rayon Co., Ltd.: zoy) dissolved in 1,2-dichloroethane 70 7ij K was applied to the solution so that the film thickness after drying was 10 fim. An electrophotographic photoreceptor of the present invention was prepared by forming a carrier transport layer.The electrophotographic photoreceptor was subjected to the same measurements as in Example 1.
- hae, ■R +-=o・v IA m
You can get it. Example 6 A 1% ethylenediamine solution of Exemplified Compound A-(2) was placed on the conductive support provided with the intermediate layer used in Example 5 so that the film thickness after drying was 0.3 I'm5. to form a carrier generation layer. Then 1-[:4-(N,N-diethylylamino)benzylidene]-amino-1, 2, 3. 4 Tetrahydroquinoline (compound K-(5) below) 6 g of K-(5) and polyester resin "Pyro Y200J (manufactured by Toyobo Co., Ltd.) 10, 9 and 3,2-dichloroethane 70 g
The electrophotographic photoreceptor of the present invention was prepared by dissolving the solution in mA and applying the IC to a film thickness of 2 μm after drying to form a carrier (transfer layer).About this electrophotographic photoreceptor The same measurements as in Example were carried out, and the results shown in Table 4 were obtained. ) A comparative electrophotographic photoreceptor was prepared in the same manner as above. This electrophotographic photoreceptor was subjected to the same measurements as in Example 1, and the results are shown in Table 4. Example 7 A carrier generation layer was formed in the same manner as in Example 5 except that Exemplified Compound A-(48) was replaced with Exemplified Compound A-(10). On top of this, 1-(1-phenyl-4-carbazolyl (Compound-(6)) 6F Togi Recarbonate “Fly 3
A carrier transport layer was formed by coating a solution obtained by dissolving 10 g of Nnlite L-1250J (manufactured by Ryotai Kasei Co., Ltd.) in 70 g of 2-dichloroethane so that the film thickness after drying was 10μ711. An electrophotographic photoreceptor was prepared. This electrophotographic photoreceptor; C was measured in the same manner as in Example 1 and found to be E% = 2. It was 5 lux and Vn 20■. Example 8 The surface of an aluminum drum with a diameter of 100 mm (thickness 0.0 made of C vinyl chloride-vinegar-resistant vinyl-maleic anhydride copolymer "Eslec λtF-" OJ (manufactured by Tsukisui Kagaku Co., Ltd.)
A 5 μm intermediate layer was provided, and exemplified compound A-(35
) was mixed with 4g of 1,2-dichloroethane 4QQ hat K, and the dispersion was dispersed for a while using a ball mill dispersion machine, and the dispersion was coated so that the film thickness after drying was 0.6 μm to form a carrier generation layer. Furthermore, on top of this, a 4,4'-methyl-4'-(4-chloro)styryl-triphenylamine well (the following compound K
- (6) ) 30 & and polycarbonate resin [Kopion S-1000 J (manufactured by Mitsubishi Kasu Chemical Co., Ltd.) 5
0 1 (!: was dissolved in 1,2-dichloroethane K - (6) 400 ml Km, and the film thickness after drying was 13/zm.
A carrier transport layer was formed by coating L51 (a carrier transport layer) to produce a drum-shaped electrophotographic photoreceptor. ■2 J (tJ＼Western University Photographer'J
? When I copied the image using a modified machine (C installed) of J: 'ji), I was able to obtain a high image last, faithful to the original image, and a clear copy. Comparative Example 3 In Example 8, Exemplary Compound A-(35) was replaced with a trisazo compound (c'' (3) represented by the following structural formula).
) A comparative drum-shaped photoreceptor was prepared in the same manner as in Example 8, except that the photoreceptor was replaced with 1.), and the copied images were evaluated in the same manner as in Example 8. Only images with a large amount of capri were obtained. Furthermore, as copying was repeated, the contrast of the copied image decreased, and after 2000 repetitions, hardly any copied image could be obtained. (3) Example 9 A conductive support made of polyester film coated with aluminum oxide, L: vinyl chloride, vinegar mbi=tv -Anhydrous maleiso@copolymer rhthrene aMy
-16J (Sekisui Chemical Co., Ltd. 11a), thickness 0.06μ
An intermediate layer of m is provided, and exemplified compound A-(37)5 is provided thereon.
1 and polycarbonate resin [Panlite L-1250J
(manufactured by Yojin Kasei Co., Ltd.) 3.37 and dichloromethane 100
FaZK was added thereto and a dispersion liquid was dispersed in a ball mill for another period of time, and a dispersion liquid was coated to give a dry film thickness of 10 μm to prepare 8 electrophotographic photoreceptors. The photoreceptor obtained as above was charged with a voltage of +6KVI.
Except for changing C, EX and VR were measured in the same manner as in Example 1. First result n E% = 3.511] x m
See and input γF+ = +20 V. Example 1O 1-[4-(N,N-diethylaminobenzylidenezuamino-), 2.3°4-tetrahydroquinoline 6I and polyester resin "Vylon 20" were used as a carrier transport layer on a polyester film deposited with aluminum.
QJ (Toyobo Co., Ltd.) 1011 was dissolved in 70 mt of 1.2-'/chloro1conitane (C, and this solution was applied so that the film thickness after drying was 1 ottt. 2 Exemplary compound acquaintance・(7) 1g and person−(M
2) 1.9 and 1,2-diku I2 ethane 110trr
The dispersion was mixed with 1K and dispersed in a ball mill for a short time, and then applied to a dry film thickness of 0.5 μm to form a carrier generation layer, thereby forming an electrophotographic photoreceptor of the present invention. The photoreceptor obtained in step 5 was evaluated in the same manner as in Example 9, and found to be 'Bk4 = 3.51 ux-sec and VR, . . . +20 V. Example 11 A 2% ethylenediamine solution of Exemplary Compound A-(3) was
It was applied onto a polyester film coated with aluminum so that the dry film thickness was 0.5 μ'm K.
A carrier generation layer was formed. Furthermore, as a carrier transport layer, 4-methoxy-4'-sutrotriphenylamine (the following compound -(7)), 6-methyl-1
-(I-ethyl-4-carbazolyl)methylidene-amine-1,2,3,4-tetrahydroquinoline (compound K -+81 below), also f.
・Triphenylamine ('F compound K −+91
) separately (tC each) and about 10g of polycarbonate -
K-<7) K-(9) Tree WI (manufactured by Yojin Kasei Co., Ltd., Panlite I, -1250)
A solution prepared by dissolving 14 g of 1,2-ditaloloethane in 140 m6 of 1,2-ditaloloethane was coated on 5 to give a dry film thickness of 12 μm and dried to obtain photoreceptors each containing a different type of carrier transport substance. These three types of photoreceptors were manufactured by Rodenki Manufacturing Co., Ltd.
Using P-428 electrostatic paper tester

[, the exposure amount (half-reduced exposure amount, Fj4) required to attenuate the following times and minutes was measured. In addition, the surface potential (residual potential) VB after exposure with an exposure amount of 301 ux·Bee was measured. As shown in Table 5, the results were good in combination with any carrier transport substance. Table 5 Comparative Example 4 Example Compound 1 (3) was converted into the following bisazo compound ((1-
Same as (Example 1) except that (41) was replaced (CJ
4゜・As a result of creating a photoreceptor and evaluating its characteristics,
G-(41 As shown in Table 6, the results varied depending on the carrier transport material. Table 6- Example 12 On the conductive support provided with the intermediate layer used in Example 5 ((,
Example Compound 1 - 2g of (40) and 1,2-dichloroethane]ootnt were well dispersed and mixed, and after drying, the film thickness was 0.
．． 3μrILK will be 5K]! & Cloth carry, 7 generation layers were created. Next, 6 g of 3-(p-methoxystyryl)-9-(p-methoxytunyl)carbazole (the following compound K-(10)) and polycarbonate "Panrai" L-1250 (Yojin Kasei Co., Ltd.) were added thereon as a carrier transport substance. A carrier transport layer was formed by dissolving 30g of K-(10) in 90I of 1,2-dichloroethane and applying the solution to a dry film thickness of 10 μml to form a carrier transport layer, thereby forming an electrophotographic photoreceptor of the present invention. This electrophotographic photoreceptor was tested indoors at 5°C and 0°C.
The electrophotographic properties 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.
Example 13 Exemplary compound A-(41) 2JF and 1,2-dichloroethane 1 were placed on the conductive support provided with the intermediate layer used in Example 5.
iomJ is well dispersed and mixed, and the film thickness after drying is 0.311.
A carrier generation layer was created by applying the coating so as to have rlL. For this carrier generation layer, an ultra-high pressure mercury wrap (manufactured by Tokyo Shibaura Electric Co., Ltd.) was placed at a distance of 30α, and
600ea/- of glue V light was irradiated. Next, j-phenyl-3-(p-jethylaminostyryl)-5-(p-diethylaminofur) pyrazoline (the following compound) is added as a carrier transport substance onto this carrier generation layer that has been irradiated with UV light -(11)) 7I and polycarbonate [
Panlite L-1250:1 (manufactured by Yotaikasei Co., Ltd.) 10g
and to 1,2-dichloroethane-(]1)90. ! The film thickness after drying the Flc dissolved liquid is 1211.
The electrophotographic photoreceptor of the present invention was prepared by coating the electrophotographic photoreceptor to form a carrier transport layer. The same measurements as in Example 6 were carried out on this electrophotographic photoreceptor. The results are shown in Table 8. Example 14 Do not irradiate 'Uv light after forming the carrier generation layer (An electrophotographic photoreceptor of the present invention was prepared in the same manner as in Example 13, and the same m-trace as in Example 5 was carried out. The results are shown in Table 8. As is clear from the results in Table 8, the electrophotographic photoreceptor of the present invention has excellent sensitivity and residual potential characteristics when irradiated with UV light.
It can be seen that the amount of fluctuation in the acceptance potential is small, and it is stable against light. Comparative Example 5 Compound A-(41) was converted into the following bisazo compound (C-(5
1) Example 3 and Example 14 except that K was changed, and G
-(51) 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, using the above compound, The prepared electrophotographic photoreceptor 1-j deteriorated in sensitivity/residual potential characteristic C1 due to UV light irradiation, and the amount of variation in acceptance potential was large.Example] 4 In Example 5, exemplified compounds A. −(
A drum-shaped electrophotographic photoreceptor was produced in the same manner except that 38) was replaced. The spectral sensitivity of this photoreceptor at 790 nm was 1.35 μJ/cdc (half exposure amount). The photoconductor of the present invention has a laser beam intensity of OJ5 on the photoconductor surface.
A live photo test was carried out using an experimental machine equipped with a semiconductor laser (790 nm) with a power output of mW. After the surface of the photoreceptor was charged to -6 KV, it was exposed to laser light and reversely developed at a bias voltage of -250 V. Upon completion, a good image without capri 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 (σ). The spectral sensitivity of this photoreceptor at 79Or+n+ was 1- t1
It was 2.2 μJ/d (half exposure N). Using this comparative photoreceptor, an actual photographing test using a semiconductor laser was conducted in the same manner as in Example 14, but there were many capri spots and a good image iq 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. 1... Conductive support, °2... Carrier generation layer,
3... Middle layer transport layer, 4... Photosensitive layer, 5...
Intermediate layer, 6... layer containing a carrier transport substance, 7.
...Carrier-generating substance 6 Agent Kuwahara @ Bimo 2

Claims (1)

[Scope of Claims] (]) An electrophotographic photoreceptor comprising a photosensitive layer containing a bisazo compound represented by the following general formula [I] on a conductive support. General formula [■] [In the formula, Yl and Y2: hydrogen atom,] a group selected from a rogen atom, a cyano group, an alkyl group, or an alkoxy group, H and Z: substituted/unsubstituted aromatic carbocycle or a group of atoms necessary to constitute a substituted/unsubstituted aromatic carbon ring, Q: substituted/unsubstituted carbamoyl group or substituted/unsubstituted sulfamoyl group, R1: hydrogen atom, substituted/unsubstituted alkyl group , substituted/unsubstituted amino group, substituted/unsubstituted carbamoyl group, carboxy group and its ester group, or cyano group, A': substituted/unsubstituted aryl group, R2 and R3: substituted/unsubstituted alkyl group , represents a substituted or unsubstituted aralkyl group, or a substituted or 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 trisazo compound represented by the following.