JPS59168455A - Organic photoconductor - Google Patents

Abstract

PURPOSE:To obtain an electrophotographic sensitive body having high sensitivity characteristics and stable potential characteristics in repeated uses by using a specified org. photoconductor. CONSTITUTION:An electrophotographic sensitive body having practical high sensitivity characteristics and stable potential characteristics in repeated uses is obtained by using one of org. photoconductors, such as compds. of formulae IIand III, having general formula I in which A is an aromatic coupler component. This electrophotographic sensitive body can be used for not only an electrophotographic copying machine but also for the wide fields utilizing electrophotography, such as laser printers and CRT printers. This org. photoconductor can be used for solar cells and optical sensors in addition of the electrophotographic sensitive body. The solar cells can be prepared, e.g. by sandwiching this photoconductor with indium oxide and aluminum.

Description

[Detailed description of the invention] The present invention relates to organic photoconductors.

BACKGROUND OF THE INVENTION Electrophotographic photoreceptors using inorganic photoconductors such as selenium, cadmium sulfide, and zinc oxide as photosensitive components have been known.

On the other hand, since the discovery that patented therapeutic compounds exhibit photoconductivity, many organic photoconductors have been developed. For example, organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, carbazole,
Low-molecular organic photoconductors such as anthracene, pyrazolines, oxadiazoles, hydrazones, polyaryl alkanes, phthalocyanine pigments, azo pigments, cyanine dyes, polycyclic quinone pigments, R-rylene thread pigments, indigo dyes, thioindigo Organic pigments and dyes such as dyes or methine squarate dyes are known. In particular, organic pigments and dyes with photoconductivity are easier to synthesize than inorganic materials, and the variety of compounds that exhibit photoconductivity in an appropriate wavelength range has been expanded.
Many photoconductive organic pigments and dyes have been proposed. For example, U.S. Patent No. 4123270, U.S. Patent No. 424761
No. 4, No. 4251613, No. 4251614,
Same No. 4256821, Same No. 4260672, Same No. 4
No. 268596, No. 4278747, No. 4295
628, an electrophotographic photoreceptor using a photoconductive disazo pigment as a charge generation substance in a photosensitive layer functionally separated into a charge generation layer and a charge transport layer is known.

An electrophotographic photoreceptor using such an organic photoconductor can be produced by coating by appropriately selecting a binder, so it is possible to provide an extremely highly productive and inexpensive photoreceptor.
Moreover, while it has the advantage of being able to freely control the sensitive wavelength range by selecting organic pigments, this photoreceptor has problems with sensitivity and durability, and so far only a few have been put into practical use. .

OBJECTS OF THE INVENTION It is an object of the present invention to provide novel organic photoconductors.

Another object of the present invention is to provide an electrophotographic photoreceptor having improved photographic properties by using a specific organic photoconductor, thereby achieving practical high sensitivity properties and repeatability. An object of the present invention is to provide an electrophotographic photoreceptor having stable potential characteristics when used in p-return use.

The present invention comprises an organic photoconductor represented by the following general formula (1).

The general formula A represents a coupler component having aromatic properties, and it is preferable that A is selected from coupler components represented by the following general formulas (2) to (4).

"x'" is a residue that forms an aromatic hydrocarbon ring or a heterocycle such as a naphthalene ring, anthracene ring, carbazole ring, dibenzofuran ring, benzcarbazole ring, etc. by condensation with the -
CONRI A group represented by R2 (where R1 is a group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group such as methyl, ethyl, propyl, butyl, 2-hydroxyethyl, 5-hydroxypropyl, etc., or an aryl group such as phenyl, naphthyl, etc.) R2 is a substituted or unsubstituted alkyl group such as methyl, ethyl, propyl, butyl, 2-hydroxyethyl, 3-hydroxypropyl, an aryl group such as phenyl, naphthyl, and pyridyl, quinolyl, carbazolyl, thiazolyl. (represents a group selected from a group consisting of heterocyclic residues such as ), or -〇〇N)lNR3R4 (wherein R3 and R4 represent substituted or unsubstituted aryl groups such as phenyl and naphthyl) represents. As substituents in R1 to R4 above, alkyl groups such as methyl and ethyl,
710 gene atoms such as fluorine, chlorine, and bromine; alkoxy groups such as methoxy and ethoxy; acyl groups such as acetyl and benzoyl; alkylthio groups such as methylthio and ethylthio;
Examples include arylthio groups such as phenylthio, aryl groups such as phenylthio, aralkyl groups such as benzyl, nitro groups, cyan groups, and substituted amine groups such as dimethylamino, diethylamino, dibenzylamino, and ethylamino.

In the general formulas (3) and (4), R5 is a substituted or unsubstituted alkyl group, a phenyl group,
Represents a group selected from the group consisting of radical groups such as naphthyl. More specifically, B5 is an alkyl group such as methyl, ethyl, propyl, hydroxyalkyl group such as hydroxymethyl, hydroxyethyl, alkoxyalkyl group such as methoxymethyl, ethoxymethyl, ethoxyethyl,
Cyanoalkyl group, aminoargyl group, N-alkylaminoalkyl group, N,N-dialkylaminoalkyl group, halogenated alkyl group, aralkyl group such as benzyl and phenethyl, phenyl group and substituted phenyl group, naphthyl group, substituted naphthyl group, (Examples of the substituents include substituents for R1 to R4 in general formula (2)).

Typical organic photoconductors of the present invention include the following disazo pigments.

Disazo pigments These disazo pigments can be used in combination of two or more. In addition, these pigments can be obtained by subjecting the diamine represented by to tetrazotization using a conventional method, and then coupling the corresponding coupler in the presence of an alkali, or by converting the tetrazonium salt of the diamine described above into a borofluoride salt or a zinc chloride double salt. It can be easily produced by coupling with cassilla in the presence of an alkali in a suitable solvent such as N,N-dimethylformamide or dimethyl sulfoxide.

Second, typical synthesis examples of the disazo pigment used in the present invention are shown below.

Synthesis Example 1 (Synthesis of the exemplified disazo pigment A1) The mixture was stirred while being cooled in an ice-water bath to bring the liquid temperature to 3C.

Next, add 4.2 y (0,061 mol) of sodium nitrite to 7 ml of water.
ml of the solution was added over a period of 10 minutes while controlling the temperature within the range of 3 to 10°C, and after the dropwise addition was completed, the solution was stirred for an additional 60 minutes at the same concentration. Carbon was added to the reaction solution and filtered to obtain a tetrazotized solution.

Next, add 700 ml of water to 21 Beef No and add 2 ml of caustic soda.
After dissolving 1S' (0.53 mol), naphthol As (
3-Hydroxy-2-naphthoic acid amolide) 16.21
(0,061 mol) was added and dissolved.

This coupler bath liquid was cooled to 6°C, and while controlling the liquid temperature at 6 to 10°C, the above-mentioned tetrazotized liquid 'fc was added dropwise with stirring over 30 minutes, and then stirred at room temperature for 2 hours.
I left it for the night. After filtering the reaction solution, the crude pigment 2047 was washed with water.
I got it. Hot filtration was then repeated five times with 400 ml of N,N-dimethylformamide. After that, purified pigment 192? was purified by heat drying under reduced pressure. I got it. The yield was 84.8%.

Elemental analysis two calculated values (%) Experimental values ((6) C76,9076,73 H4,144,3O N 10.76 10.62 Synthesis Example 2 (Synthesis of the above-mentioned exemplified disazo pigment A2) ml, concentrated hydrochloric acid 13.
A solution prepared by dissolving 3.51' (0,051 mol) of sodium nitrite in 106 - of water was added to a solution containing 24m/(0.15 mol) of sodium nitrite for 5 minutes while maintaining the temperature at 45 to 7°C. The mixture was added dropwise and then stirred at the same temperature for 60 minutes.

Next, 10.5i (0.0525 mol) of 3-hydroxy-naphthalene-2-carboxylic acid methylamide and 16.8ii' (0.42 mol) of caustic soda were dissolved in 420 parts of water, and the liquid temperature was adjusted to 4 to 10 ml. The above tetrazotized solution was added dropwise over 10 minutes while keeping the temperature at
I left it for the night.

After filtration, washing with water and drying, 2
．． A dry pigment 13.1F (yield 798%) was obtained by Soxhlet for 0 hours.

Elemental analysis: Calculated value (@ Experimental value (@ c 73.1s 72.96H4,314
, 28 N12. so 13.01 Synthesis Example 3 (Synthesis of the above-exemplified disazo pigment Tsuta 5) 2t
Pour 700m of water into a beaker and add 2 ml of caustic soda to it.
After adding and dissolving 1F- (0.53 mol), 3-hydroxy-naphthalene-2-carboxylic acid-N,N-diphenylhydrazide 21.6F (0,061 mol) was added and dissolved.

Cool this coupler solution to 6°C, and adjust the liquid temperature to 6°C to 10°C.
A tetrazotized solution prepared by the same method as in Synthesis Example 1 was added dropwise under stirring over 30 minutes while controlling the temperature.Then, the mixture was stirred at room temperature for 2 hours, and then left overnight. After stirring the reaction solution, it was washed with water to obtain crude pigment 2582. This was followed by hot filtration with 400 d of N,N-dimethylformamide 5 times with 9 rims. Thereafter, 24.6f of purified pigment was obtained by heat drying under reduced pressure. The yield was 882%.

Elemental analysis: Subtraction value (%) Experimental value (%) C77,3177,41 H4,404,31 N 11.64 11.62 The synthesis methods of the three types of pigments have been described above, but in general formula (1) The other disazo pigments shown are similarly synthesized.

In a preferred application example of the organic photoconductor of the present invention, an organic photoconductor represented by the general formula (1) is used as a charge generation substance in an electrophotographic photoreceptor in which a photosensitive layer is functionally separated into a charge generation layer and a charge transport layer. can be used. The charge generation layer contains as much of the organic photoconductor as possible in order to obtain sufficient absorbance, and in order to shorten the range of the generated charge carriers, a thin film layer, e.g. , preferably a thin film layer having a thickness of 0.01 micron to 1 micron. This means that most of the incident light is absorbed by the charge generation layer, generating many charge carriers, and that the generated charge carriers are absorbed by angular binding and trapping (
This is due to the need to inject into the charge transport layer without being deactivated by traps.

The charge generation layer can be formed by dispersing the above-mentioned organic photoconductor in a suitable binder and coating it on the substrate, or can be obtained by forming a vapor-deposited film using a true vapor deposition apparatus. . Inders that can be used to form the charge generating layer by coating can be selected from a wide range of insulating resins, as well as organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, and polyvinylpyrene. can. Preferably C, polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and heptalic acid, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose thread resin, urethane resin,
Examples include insulating resins such as epoxy resin, casein, polyvinyl alcohol, and polyvinylpyrrolidone. The amount of resin contained in the charge generation layer is suitably 80 M% or less, preferably 40% by weight or less.

It is preferable to select a solvent that dissolves these resins from a range of v, which varies depending on the type of resin, and a solvent that does not dissolve the underlying charge transport layer or subbing layer. Specific single-organic solvents include alcohols such as methanol, ethanol, and impronosol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and dimethyl. Sulfoxides such as sulfoxide, ethers such as tetrahydrofuran, dioxane, ethylene glycol monomenal ether, esters such as methyl acetate, ethyl acetate, chloroform, methylene chloride,
Aliphatic halogenated hydrocarbons such as dichloroethylene, carbon tetrachloride, trichlorethylene, ben7ane, toluene, xylene, ligroin, monochlorobenzene,
Aromatics such as dichlorobenzene can be used.

Coating methods include acid coating method, spray coating method, spinner coating method, bead coating method,
This can be carried out using a coating method such as a Mayer-Par coating method, a blade coach ink method, a roller coating method, or a curtain coating method. For drying, it is preferable to dry to the touch at room temperature and then heat dry. Heat drying at a temperature of 30°C to 200°C for 5 minutes to 2
It can be carried out stationary or under blown air for a period of time within a range of hours.

The charge transport layer is electrically connected to the charge generation layer described above, and has the function of receiving and receiving charge carriers injected from the charge generation layer in the presence of an electric field, and transporting these charge carriers in surface trenches. have. At this time, this charge transport layer may be laminated on or under the charge generation layer. However, it is desirable that the charge transport layer is laminated on the charge generation layer.

Since a photoconductor generally has the function of transporting charge carriers, a frost, charge transport layer can be formed by this photoconductor.

The material that transports charge carriers in the charge transport layer (hereinafter simply referred to as charge axis 1 transport material η) must be substantially insensitive to the wavelength range of the magnetic waves to which the charge generation layer is sensitive. It's so sad. The "electromagnetic waves" mentioned here include gamma rays,
It includes a broad definition of "light" that includes radiation, ultraviolet rays, visible light, near-infrared rays, infrared rays, far-infrared rays, etc. When the photosensitive wavelength range of the charge transport layer coincides with or overlaps that of the charge generation layer, charge carriers generated in both layers trap each other, resulting in a decrease in sensitivity.

Charge transport substances include charge transport substances and hole transport substances, and electron transport substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4,7-trinitro-9-fluorenone, 2
,4,5.7-tetranitro-9-fluorenone,2,
4.7-T+J nitro-9-dicyanomethylenefluorenone, 2,4,5.7-tetranitroxanthone, 2
, 4.8-trinidrothioxanthone and other electron-withdrawing substances, and polymerized products of these electron-withdrawing substances.

Examples of hole transporting substances include pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N
-Phenylhydrazino-6-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-6-methylidene-10-ethylphenothiazine, N , N-diphenylhydrazino-3-methylidene-10-ethylphenoxazine, P-diethylaminobenzaldehyde-N,N-diphenylhydrazone, P-diethylaminobenzaldehyde-N-α-naphthyl-N-phenylhydrazone, P-pyrrolidinonzaldehyde N,N-diphenylhydrazone, 1,5.
5-trimethylindolenine-ω-aldehyde-N,N
->Hydrazones such as phenylhydrazone, P-diethylbenzaldehyde-6-methylbenzthiazolinone-2-hydrazone, 2,5-bis(p-diethylaminophenyl)-1,3,4-oxadiazole, 1- Phenyl-3-(P-diethylaminostyryl)-5-(p
-uethylaminophenyl)pyrazoline, 1-[quinolyl (Z):] -5-(p-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline,
1-[pyridyl (2))-3-(P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-46-medoxyviridyl (2))-3
-(p-diethylaminostyryl)-s-(p-diethylaminophenyl)pyrazoline, 1-pyridyl (8)
) -3-(P-diethylaminostyryl)-5-
(P-diethylaminophenyl)vitlazoline, 1-[
revidyl (2)) -3-(P-diethylaminostyryl)-5-(p-diethylaminophenyl)pyrazoline, 1-pyridyl (2)]-3-(P-diethylaminostyryl)-4-methyl-5-( p-diethylaminophenyl)pyrazoline, 1-[pyridyl(2))
-3-(α-methyl-P-diethylaminostyryl)-
5-(p-diethylaminophenyl)pyrazoline, 1-
Phenyl l/-3-(P-diethylaminostyryl)-
4-Methyl-5-(P-diethylaminophenyl)virasone, 1-phenyl-6-(α-ni/dyl-P-
Pyrazolines such as 5-(P-diethylaminophenyl)-pyrazoline, sub-roviraso-1, 2-(P-diethylaminostyryl)
-6-dinithylaminobenzoxazole, 2-(p-
oxazole thread compounds such as 2-(P-diethylaminostyryl)-6-dinithylaminobenzothia7-
Thiazole thread compounds such as H-K (4-diethylamine-2-methylphenyl)-phenylmethane, triarylmethane thread compounds such as 1,1-bis(4-N,
N-diethylamino-2-methylphenyl)hebutane,
Polyarylalkanes such as 1,1,2.2-tetrakis(4-N,N-dimethylamino-2-methylphenyl)ethane, triphenylamine, polyN-vinylcal/zsol, polyvinylpylene, polyvinyl Nylanthracene polyvinylacridine, bo+) -9-hinylphenylanthracene, birene-formaldehy)'
m IIW, ethyl calfucisol formal 1 human resin, and the like.

Inorganic materials such as selenium, selenium-tellurium amorphous silicon, and i(t,/7 domium) can also be used as these organic charge transport materials.

Moreover, these charge transport object angles can be used alone or in combination of two or more.

When the charge transport material does not have film-forming properties, a film can be formed by selecting an appropriate binder. Examples of trees that can be used as binders include acrylic resin polyarylate, polyester polycarbonate, bo-1-nostyrene acrylonitrile-styrene copolymer,
Insulating resins such as acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone, polyacrylamide, polyamide, chlorinated rubber, or organic photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, polyvinylpyrene, etc. be able to.

Since the charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. Generally it is 5 microns to 60 microns, with a preferred range of 8 microns to 20 microns. When forming the charge transport layer by coating, an appropriate coating method as described above can be used.

A photosensitive layer having such a laminated structure of a charge generation layer and a charge transport layer is provided on a substrate having a conductive layer. Examples of substrates having a conductive layer include those in which the substrate itself is conductive;
For example, aluminum, aluminum alloy, copper, zinc, stainless steel, vanadium, molybdenum, chromium, titanium,
Nickel, indium, gold, platinum, etc. can be used, and in addition, plastics having a layer formed by vacuum evaporation of aluminum, aluminum alloy, indium oxide, tin oxide, indium oxide-tin oxide alloy, etc. (for example, polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, fluorinated ethylene, etc.), conductive particles (e.g.
A substrate in which plastic is coated with carbon black, #particles, etc.) together with a suitable binder, a substrate in which plastic or paper is impregnated with conductive particles, a plastic having a conductive polymer, etc. can be used.

A subbing layer having barrier and adhesive functions can also be provided between the conductive layer and the photosensitive layer. The subbing layer is casein,
Polyvinyl alcohol, nitrocellulose, ethylene-
Acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane,
It can be formed from aluminum oxide, etc.

The additional thickness of the undercoat layer is 0.1 micron to 5 micron, preferably 0.5 micron to 6 micron.

When using a photoreceptor in which a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order, and the charge transport material is an electron transport material, it is necessary to positively charge the surface of the charge transport layer, and exposure after charging is required. Then, in the exposed area, electrons generated in the charge generation layer are injected into the charge transport layer, and then reach the surface and neutralize the positive charge, causing a decrease in surface potential and creating an electrostatic contrast between the exposed area and the unfogged area. arise.

A visible image can be obtained by developing the latent image formed in this manner with a negatively charged toner. Either fix this directly, or transfer the toner image to paper or plastic film, etc.
It can be developed and fixed.

Alternatively, a method may be used in which the electrostatic latent image on the photoreceptor is transferred onto an insulating layer of transfer paper, then developed and fixed. The type of developer, the developing method, and the fixing method may be any known ones or known methods, and are not limited to specific ones.

On the other hand, when the charge transport material consists of a hole transport material, the surface of the charge transport layer must be negatively charged, and when exposed to light after charging, holes generated in the charge generation layer are injected into the charge transport layer in the exposed area. , which then reaches the surface and neutralizes the negative charges, resulting in attenuation of the surface potential and an electrostatic contrast between the surface potential and the unexposed area. During development, it is necessary to use a positively charged toner, contrary to the case where an electron transport material is used.

Another application example of the present invention is an electrophotographic photoreceptor in which the above-described organic photoconductor is contained in the same layer together with a charge transport material. In this case, a charge transfer complex compound consisting of boll-N-vinylcarhasol trinitrofluorenone can be used in addition to the above-mentioned charge transport substance.

The electrophotographic photoreceptor of this example can be prepared by dispersing the aforementioned organic photoconductor and charge transfer complex compound in a polyester solution dissolved in tetrahydrofuran, and then forming a film thereon.

In any photoreceptor, the pigment used is of the general formula (1)
For purposes such as increasing the sensitivity of a photoreceptor or obtaining a panchromatic photoreceptor, which contains at least one moderate pigment selected from the disazo pigments shown in It is also possible to use the disazo pigment represented by the general formula (1) in combination with a combination of two or more glazes, or with a charge generating object selected from known dyes and pigments.

The electrophotographic photoreceptor containing the organic photoconductor of the present invention can be used not only in electrophotographic copying machines but also in a wide range of electrophotographic applications such as laser printers and CRT printers.

In addition to the above-mentioned electrophotographic photoreceptor, the advanced electric material of the present invention can also be used for solar cells and optical sensors.

Solar cells can be made hh by sandwiching the aforementioned organic photoconductors with, for example, indium oxide and aluminum.

Hereinafter, the present invention will be specifically explained using application examples.

Example 1 Aqueous ammonia solution of casein (casein 1
11 parts of 122.28% ammonia water and 222 parts of water were applied using a Mayer bar so that the film thickness after drying was 1.0 micron, and dried.

Next, the organic light guide s of the above-mentioned disazo pigment store 1
The mixture was added to a solution prepared by dissolving 2y of butyral resin (degree of butyralization: 63 mol %) in 95 ml of ethanol, and dispersed with an attritor for 2 hours.

This dispersion was applied to the previously formed casein layer using a one-year coating so that the film thickness after drying was 0.5 microns, and dried to form a charge generation layer.

Next, the hydrazone compound 5f of the structural formula and the polymethyl methacrylate resin (number average molecular weight 100,000) 5f were mixed with benzene 70
7! The material was dissolved in 100% chloride and applied on the charge generation layer using a Mayer bar to a dry film thickness of 12 microns, and dried to form a charge transport layer [7].

The electrophotographic photoreceptor thus prepared was statically charged with corona at 15 KV using an electrostatic copying paper tester Moclθ/5P-428 manufactured by Kawaguchi Denki ■, and then charged for 100 kV in the dark.
After being held for a second, it was exposed to light at an illuminance of 5)) ux, and the charging characteristics were examined.

As for the charging characteristics, the blush potential (vO) and the exposure amount (E-) required to attenuate the potential to a bar when dark attenuated for 1 second were measured.

Furthermore, in order to measure the fluctuations in bright area potential and dark area potential when repeatedly used, the photoreceptor prepared in this example was
It was attached to the cylinder of an electrophotographic copying machine equipped with a KV corona charger, an exposure optical system with an exposure amount of 12 tux, and an eec, a developing device, a transfer charger, a static elimination exposure optical system, and a cleaner. This copying machine is configured to obtain an image on transfer paper as the cylinder is driven. Using this copier, we measured the initial bright area potential (VL) and dark area potential (VD), and the bright area potential (VL) and dark area potential after 5000 uses.
The position (VD) was measured. The results are shown below.

Vo: -605 volts EH: 5.2 tux, eec Initial After 5000 cycles VD knee 610 volts, VL knee 25 volts VD' 59
5fi Reto, V, Knee 4O Volt Examples 2 to 14 An electrophotographic photoreceptor was prepared in exactly the same manner as in Example 1, except that the above-mentioned disazo pigments A2 to 14 were used in place of the disazo pigment used in Example 1. It was created.

The charging characteristics and durability characteristics of each photoreceptor were measured in the same manner as in Example 1. The results of Kori et al. are shown below.

Initial 5000 times” Age 2 -615 4.4 -600 -30 -
580 -40(2) 3 -605 5.6 -595 -55 -
595 -65(3) 4 -590 5.5 -605 -50 -
600 -50(4) 5 -605 4.0 -600 -25 -
590 -30(5) 6 -595 4.8 -610. -35-
595 -45(6) 7 -615 5.0 -600 -50 -
590 -65(7) 8 -600 4.2 -590 -25 -
575 -35(8) 9 -600 5.3 -620 -50 -
610 -50(9) 10 -585 4.1-6oo -20-5
90-4000) 11 -600 4.5 -605 -25
-585 -30 (b) 12 -/)10 3.9 -595 -20
-580-45 @ Initial 13 after 5000 cycles -590 5.4 -600 -40
-585 -45ω→ 14 -605 5.8 -610 -65
-600 -65αExample 15 On the charge generation layer prepared in Example 1, 2,4,7-trinitro-9-fluorenone 5 f 41J -4,4'
-dioxydiphenyl-2,2-propane carbonate (molecular weight 300,000) 5F in tetrahydrofuran 7
The coating amount after drying of the coating solution prepared by dissolving in 0- is 10
It was applied to an area of 97 m2 and dried.

The electrostatic charge of the electrophotographic photoreceptor thus prepared was measured in the same manner as in Example 1. At this time, the charge is 4iJ! The gender was set as ■. The results are shown below.

vO2 +610 volts BH: 6. G tux, eec Initial dark potential VD e +600 volts Initial light potential VL: +55 volts Example 16 A polyvinyl alcohol film having a thickness of 1.1 microns was formed on the aluminum surface of an aluminum vapor-deposited polyethylene terephthalate film.

Next, the disazo pigment dispersion used in Example 1 was placed on the polyvinyl alcohol layer on which the dispersion liquid had been formed, so that the film thickness after drying was 0.
It was coated with a Mayer par to a thickness of 5 microns and dried to form a charge generation layer.

Next, pyrazoline compound 52 of the structural formula and polyarylate resin (condensation polymer of bisphenol A and terephthalic acid-isophthalic acid)
A solution obtained by dissolving No. 52 in 70% of tetrahydrofuran was applied onto the charge generation layer so that the film thickness after drying was 10 microns, and dried to form a charge transport layer.

The charging characteristics and durability characteristics of the photoreceptor thus prepared were measured in the same manner as in Example 1.

The results are shown below.

vO: -580 volts E4 2 4.5 1. ux, sec Initial dark potential VD: -610 volts Initial light potential VL
2-25 Volt Example 17 An ammonia aqueous solution of casein was applied onto an aluminum plate with a thickness of 100 microns and dried to form a subbing layer with a thickness of 1.1 microns.

Next, 2,4.7-dolinitro9-fluorenone5?
and BoIJ-N-vinylcarbazole (number average molecular weight 30
0,000) was dissolved in 70 g of tetrahydrofuran to form a charge transfer complex.

A photoconductor 17 of this charge transfer complex compound and the above-mentioned disazo pigment A1 was added and dispersed in a solution in which 5 g of polyester resin (Vylon, manufactured by Toyobo) was dissolved in 70 ml of tetrahydrofuran.This dispersion was used as a subbing layer. The film was coated on the film to a dry film thickness of 12 microns and dried.

The charging inertia and durability characteristics of the photoreceptor thus prepared were measured in the same manner as in Example 1. The results are shown below. However, the band 1 polarity was set to ■.

vO: +610 volts F2%: 5,4 tux, day θC

Claims (1)

[Claims] (1) An organic photoconductor represented by the following general formula (1). However, the formula 2 chunin represents a coupler component having aromatic properties.