JPS58224354A - Photoconductive composition - Google Patents

Abstract

PURPOSE:To obtain a photoconductive compsn. having high sensitivity to semiconductor laser beams, by using a specified cyanine dye as a charge generating substance. CONSTITUTION:An aluminum plate is coated with an aq. ammonia soln. of gelatin and dried to form an undercoat layer. A charge generating layer is formed by coating the undercoat layer with a soln. prepd. by dissolving in a solvent together with a binder resin, such as butyral resin, a compd. represented by formula I in which Z1, Z2 are each an atomic group needed to complete a hetero ring contg. N; A1, A2 are each a divalent hydrocarbon group forming a 5- or 6- membered ring; R1, R2 are each H or optionally substd. alkyl; R3, R4 are each H or halogen; X(-) is an anion; m, n are each 0 or 1; and l is 1 or 2. A charge transfer layer is formed on the charge generating layer to prepare an electrophotographic receptor. The cyanine compd. may be added to the same layer together with a charge transfer substance.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a photoconductive composition, and more particularly to a photoconductive composition suitable for an electrophotographic photoreceptor for an electrophotographic printer using a laser, particularly a semiconductor laser having an oscillation wavelength on the long wavelength side, as a light source. The present invention relates to a composition.

An electrophotographic printer that uses a laser as a light source modulates the laser using an electrical signal corresponding to image information, and scans the modulated laser light onto a photoreceptor using a galvano mirror or the like to create an electrostatic image. After formation, a desired reproduced image can be formed by sequentially performing toner development and transfer. The laser used at this time was generally helium-cadmium (oscillation wavelength: 441
．． 6 nm) and helium-neon (oscillation wavelength: 632.
8 nm) gas laser. Therefore, the photoreceptor used for such a light source only needs to be spectrally sensitized to about 650 nm, such as one using a charge transfer complex of polyvinylcarbazole and trinitrofluorenone in the photosensitive layer, or one using selenium as the photosensitive layer. A photosensitive layer in which a sensitized tellurium vapor-deposited layer is used in a photoreceptor, a selenium vapor-deposited layer is formed on a conductive layer as a charge transport layer, and a selenium-tellurium vapor-deposited layer is formed on this selenium vapor-deposited layer. There are those using cadmium sulfide spectrally sensitized with a sensitizing dye as the photosensitive layer, and those that are functionally separated into a charge generation layer and a charge transport layer containing organic pigments, and whose photosensitive wavelength range is extended to longer wavelengths. Some are known that use a photosensitive layer that is sensitized up to the sides.

Incidentally, in recent years, semiconductor lasers have been developed that are small, low-cost, and capable of direct modulation.
The oscillation wavelength of this laser often has a wavelength of 750 nm or more. Therefore, when forming an electrophotographic image using such a semiconductor laser, the absorption characteristics of the laser-sensitive coating have an absorption peak on the long wavelength side (generally 750
However, conventional laser-sensitive coatings, especially coatings formed mainly of inorganic materials, have a high reflectance to laser light, resulting in a low laser utilization rate. However, it has the disadvantage that high sensitivity characteristics cannot be obtained, and the sensitive wavelength range is limited to 750.
If the thickness is more than 10 nm, the layer structure of the laser-sensitive coating becomes complicated, and furthermore, the color of the sensitizing dye used fades during repeated charging and exposure.

In addition, a compound that exhibits photoconductivity to infrared rays -) 205
17 (1981, 5), but in general, organic compounds that have absorption characteristics on the longer wavelength side are more unstable to heat, and may not have high sensitivity characteristics. It is often technically difficult to obtain.

The object of the present invention is to be thermally stable and to be 750 n
Another object of the present invention is to provide a photoconductive composition that has high sensitivity to light with a wavelength of m or more. The purpose is to provide a photoreceptor.

This object of the present invention is achieved by a photoconductive composition containing a cyanine compound represented by general formula (1) and an electrophotographic photoreceptor using such a photoconductive composition.

General formula (1) Z and Z are #-substituted or unsubstituted nitrogen-containing heterocycles,
For example, the nucleus of the thiazole series (eg -thiazole, 4
-Methylthiazole, 4-phenylthiazole, 5-methylthiazole, 5-phenylthiazole, 4.5-dimethylthiazole, 4.5-dimethylthiazole, 4-
(2-chenyl)-thiazole, etc.), benzothiazole series nuclei (e.g. benzothiazole, 5-chlorobencinaazole, 5-methylbenzothiazole, 6-methylbenzothiazole, 5,6-dimethylhenzothiazole, 5 -Bromobenzthiazole, 5-phenylbenzothiazole % 5-methoxybenzothiazole, 6-methoxybenzothiazole, 5,6-cymethoxypenzotheazole, 5,6-cyoxymethylenebenzotheazole, 5-hydroxybenzothiazole , 6-hydroxybenzothiazole, 4,5,6,7-titrahydrobenzothiazole, etc.), naphthothiazole series nuclei (e.g. naph) (2,1=d) thiazole, nand (1,2-d
) thiazole, 5-methoxynaphtho(1,2-d)thiazole, 5-ethoxynaphtho(1,2-d)thiazole, 8-methoxynaphtho(2,1-d]thiazole, 7-
ethoxynaphtho(2,1-d)thiazolites, etc.).

Thionaphthenes (7,6-dJ thiazole series nuclei (e.g. 7-medoxythionaphthene (7,6-d) thiazole), oxazole series nuclei (e.g. 4-methyloxazole, 5-methyloxazole, 4-phenyloxazole) , 4,5-cy'zenyloxazole, 4-ethyloxazole, 4,5-dimethyloxazole, 5-phenyloxazole), benzoxazole series nuclei (
For example, benzoxazole, 5-chlorobenzoxazole, 5-methylbenzoxazole, 5-phenylbenzoxazole, 6-methylbenzoxazole, 5
, 6-dimethylbenzoxazole, 5-methoxype,
Izooxazole, 6-medoxypenzoxazole,
5-hydroxybenzoxazole, 6-hydroxybenzoxazole, etc.), naphthoxazole series nuclei (e.g. naph) (2,1-d)oxazole, naphtho(
1,2-d)oxazole, etc.), selenazole series nuclei (for example, 4-menarselenazole, 4-phenylselenazole, etc.).

Nuclei of the benzoselenazole series (e.g. benzoselenazole, 5-chlorobenzoselenazole, 5-methylbenzoselenazole, 5,6-dimethylbenzoselenazole,
5-Methoxybenzosennazole, 5-methyl-6-methylbenzoselenazole, 5,6-cyoxymethylenebenzoselenazole, 5-hydroxybenzoselenazole”
S 4,5,6,7-titrahydrobenzoselenazole, etc.), naphthoselenazole series nuclei (e.g. Nando (
2,1-d) selenazole, naphtho(1,2-d) selenazole), theazoline series nuclei (e.g. thiazoline,
4-methylthiazoline, 4-hydroyacimethyl-4-methylthiazoline, 4,4-bis-hydroxymethyltigzoline, etc.), oxazoline series nuclei (e.g. oxazoline), selenazoline series nuclei (e.g. -d-selenazoline), 2- Quinoline series nuclei (e.g. quinoline, 6-methylquinoline, 6-chloroquinoline, 6-medquinoline, 6-nitoxyquinoline, 6-hydroxyquinoline)
, 4-quinoline series nuclei (e.g. quinoline, 6-medoxyquinoline, 7-methylquinoline, 8-methylquinoline), ■-isoquinoline series nuclei (e.g. inquinoline,
3.4-dihydroisoquinoline), 3-inquinoline series nuclei (e.g. inquinoline), 3.3-sialgylindolenine series nuclei (e.g. 3.3-dimethylindolenine, 3.3-dimethyl-5- Chlorisodrenine, 3
, 3.5-trimenalisodorenine, 3,3.7-)dimethylindorenine), pyridine series nuclei (e.g. pyridine% 5-methylpyridine), benzimidazole series nuclei (e.g. 1-ethyl-5, 6-dichlorobenzimidazole, l-hydroxyethyl-5,6-dichlorobenzimidazole, 1-ethyl-5-chlorobenzoxazole, l-ethyl-5,6-dibromobenzimidazole, l-ethyl-5-phenylbenzoi Mitasol, l-ethyl-5-fluorobenzimidazole, ■
-Ether-5-cyanobenzimitazole st (
β-acetoxyethyl)-5-cyanobenzimidazole, l-ethyl-5-chloro-6-cyanobenzimidazole, ■-ethyl-5-fluoro-6-diatubenzimidazole, l-ethyl-5-acetylbenzimidazole , l-ethyl-5-carboxybenzimidazole, ■-ethyl-5-ethoxycarbonylbenzimidazole, l-ethyl-5-sulfamylbenzimidazole, l-ethyl-5-N-ethylsulfamylbenzimidazole sol, l-ethyl-5,6-difluorobenzimidazole, l-ethyl-5,6-diciatubenzimitazole, J4thyl-5-ethylsulfonylbenzimidazole, ■-ethyl-5-methylsulfonylbenzimidazole, ■ -Ethyl-5-trifluoromethylbenzimidazole, l-ethyl-5-) IJfluorometersulfonylpenzimidazole, l-ethyl-5-trifluoromethylsulfinylbenzimidazole, etc.) represents.

A, and Atri, substituted or unsubstituted 5-membered, especially 6-membered
Indicates a divalent hydrocarbon group (-0H, -, etc.) forming a membered ring, and these 5- or 6-membered rings may be fused with a benzene ring, a naphthalene ring, etc.

R1, and I(, are hydrogen atoms or alkyl groups (e.g., methyl end, ethyl group, n-propyl group, iSθ-propyl group, n-butyl group, 5ec-butyl group, 1So-butyl group, t-butyl group) , n-amyl group, t-amyl group,
n-hexyl group, n-octyl group, t-octyl group, etc.)', and also other alkyl groups, such as substituted alkyl groups (e.g., 2-hydroxyethyl group, 3-hydroxypropyl group, 4-hydroxybutyl group) , 2-acetoxyethyl group, carboxymethyl group, 2-carboxyethyl group, 3-carboxypropyl group, 2-sulfoethyl group, 3-sulfopropyl group.

4-sulfobutyl group, 3-sulfatepropyl group, 4
-sulfatephthyl &, N-(methylsulfonyl)-
carbamylmethyl &, 3-(7cetersulfamyl)propyl &, 4-(acetylsulfamyl)butyl groups, etc.), cyclic alkyl groups (e.g., cyclohexyl group, etc.)
, allyl group (OH,=OH-OH,-), aralkyl group (e.g., benzyl group, phenethyl group, α-naphthylmethyl group, β-naphthylmethyl group, etc.), substituted aralkyl group (e.g., carboxybenzyl group, sulfonate group, etc.) Benzyl group, hydroxybenzyl group, etc.) are included.

R and R4 represent a hydrogen atom or a halogen atom (chlorine atom, bromine atom, iodine atom).

X is a chloride ion, a specific ion, an iodide ion, a perchlorate ion, a benzenesulfonate ion, P
-) represents an anion such as -) luenesulfonate ion, methyl sulfate ion, ethyl sulfate ion, propyl sulfate ion, and XFiR, and (or) R1 itself is an anionic group, flJ, t bar So, θ , o
so, e, −(X)0θ, 80. NH-% not present. m and n represent 0 or l.

Next, representative examples of the cyanine compound represented by the above general formula (1) will be listed.

C,L
IU=1-1=(8).

c, H, I CtL (9) Ct Hs Eri C2H
5 In a preferred embodiment of the present invention, a cyanine compound represented by the general formula +11 above can be used as a charge generating substance in an electrophotographic photoreceptor in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer. The charge generation layer contains as much of the cyanine compound as possible in order to obtain sufficient absorbance, and in order to shorten the range of the generated charge carriers, it is a thin film layer, for example, 5 microns or less, preferably 0.0
Preferably, the thin film layer has a thickness of 1 micron to 1 micron. This means that most of the incident light is absorbed by the charge generation layer, producing many charge carriers.
Furthermore, this is due to the fact that the generated charge carriers need to be injected into the charge transport layer without being deactivated by recombination or trapping.

The charge generation layer can be formed by dispersing the above-mentioned cyanine compound in a suitable binder or by dissolving it together with a binder and coating it on the substrate. The binder that can be used when forming the charge generation layer by coating can be selected from a wide range of insulating resins.
It can be selected from organic photoconductive polymers such as N-vinylcarbazole, polyvinylanthracene and polyvinylpyrene. Preferably, polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and 7-talic acid, etc.),
Examples of insulating resins include polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, seculose resin, urethane resin, epoxy resin, casein, polyvinyl alcohol, and polyvinylpyrrolidone. I can do it. The resin contained in the charge generation layer is
Up to 80% by weight, preferably up to 40% by weight are suitable.

The solvent that dissolves these resins varies depending on the type of resin, and is preferably selected from those that do not dissolve the underlying charge transport layer or subbing layer. Specific organic solvents include alcohols such as methanol, ethanol, and isopropanol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone;
-Amides such as dimethylformamide and N,N-dimethylacetamide, sulfoxides such as dimethylsulfoxide, ethers such as tetrahydrofuran, dioxane, and ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, chloroform,
Hydrocarbons such as aliphatic halogenated hydrocarbons such as methylene chloride, dichloroethylene, carbon tetrachloride, and trichlorethylene, or aromatics such as benzene, toluene, xylene, refloin, monochlorobenzene, and dichlorobenzene are used. can.

Coating methods include dip coating, spray coating, spinner coating, bead coating,
This can be carried out using a coating method such as a Mayer coating method, a blade coating 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 taking charge carriers injected from the charge generation layer in the presence of an electric field, and transporting these charge carriers to the surface. have. At this time, this charge transport layer may be laminated on the charge generation layer, or may be laminated still below it. However, it is desirable that the charge transport layer is laminated on the charge generation layer.

The substance that transports charge carriers in the charge transport layer (hereinafter simply referred to as charge transport substance) is preferably substantially insensitive to the wavelength range of electromagnetic waves to which the charge generation layer is sensitive. The term "electromagnetic wave" as used herein includes a broad definition of "one ray of light that includes gamma rays, X-rays, 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 transporting substances include electron transporting substances and hole transporting substances, and electron transporting substances include chloranil, bromoanil, tetracyanoethylene, tetracyanoquinodimethane, 2,4.7-dolinitro-9-fluorenone,
2,4,5.7-tetranitro-9-fluorenone, 2
, 4.7-dolinitro 9-dicyanomethylenefluorenone, 2, 4.5.7-titranitroxanthone, 2,
Examples include electron-withdrawing substances such as 4.8-trinidrothioxanthone and polymerized materials of these electron-withdrawing substances.

Examples of hole-transporting substances include pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N
-Phenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, N,N-diphenylhydrazino-3-methylidene-10-ethylphenothiazine, N , N-diphenylhydrazino-3=methylidene-10-ethylphenoxazine, P-diethylaminobenzaldehyde N, N-diphenylhydrazone, P
-diethylaminobenzaldehyde-N-α-naphthyl-N-7enylhydrazone, P-pyrrolidinobenzaldehyde-N,N-diphenylhydrazone, 1.3.3-
Trimethylindolenine-ω-aldehyde-N,N-diphenylhydrazone, P-diethylbenzaldehyde-
Hydrazones such as 3-methylbenzthiazolinone-2-hydrazone, 2,5-vitamin(P-diethylaminophenyl)-1,3,4-4xadiazole, 1-phenyl-
3-(P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, l-[quinolyl r2
)] -3-(P-diethylaminostyryl)-5-
(P-diethylaminophenyl)pyrazoline, 1-[pyridyl(2)]-3-(p-diethylaminostyryl)-5-()l)-diethylaminophenyl)pyrazoline% to ['6-medoxypyridyl(2) ] −3
-(P-diethylaminostyryl)-5-(P-diethylaminophenyl)pyrazoline, 1-[pyridyl (81
]-3-(P-diethylaminostyryl)-5-(P-
diethylaminophenyl)pyrazoline, 1-[lepidyl (2))-3-(P-diethylaminostyryl)-
5-(P-diethylaminophenyl)pyrazoline, 1-
[Pyridyl(2)] -3-(P-diethylaminostyryl)-4-methyl-5-(P-diethylaminophenyl)pyrazo IJ:/, l-[pyridyl(2)] -
3-(α-methyl-P-diethylaminostyryl)-s
-(p-diethylaminophenyl)pyrazoline, 1-phenyl-3-(P-diethylaminostyryl)-4-methyl-5-(P-diethylaminophenyl)pyrazoline, 1-phenyl-3-(α-benzyl-P-diethylamino styryl)-5-(P-diethylaminophenyl)
Pyrazolines such as pyrazoline and spiropyrazoline,
2-(P-diethylaminostyryl)-6-ethylaminobenzoxazole, 2-(P-diethylaminophenyl)-4-(P-dimethylaminophenyl)-5-
Oxazole compounds such as (2-chlorophenyl)oxazole, 2-(P-diethylaminostyryl)-6-
Thiazole compounds such as ethylaminobenzothiazole, bis(4-diethylamino-2-methylphenyl)
-Triarylmethane compounds such as phenylmethane, ■
, 1-bis(4-N,N-diethylamino-2-methylphenyl)hebutane, 1,1,2.2-f) lakis(4-N,N-dimethylamino-2-methylphenyl)ethane, etc. Examples include polyarylalkane, triphenylamine, poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridine, poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, ethylcarbazole formaldehyde resin, and the like.

In addition to these organic charge transport materials, inorganic materials such as selenium, selenium-tellurium, amorphous silicon, and cadmium sulfide can also be used.

However, these charge transport materials 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.

Resins that can be used as binders include, for example, acrylic resin, polyarylate, polyester, polycarbonate, polystyrene, acrylonitrile-styrene copolymer, acrylonitrile-butadiene copolymer, polyvinyl butyral, polyvinyl formal, polysulfone, polyacrylamide, polyamide, chlorinated rubber, etc. poly-N-vinylcarbazole,
Mention may be made of organic photoconductive polymers such as polyvinylanthracene and polyvinylpyrene.

Since the charge transport layer has a limit in its ability to transport charge carriers, it cannot be made thicker than necessary. Typically it is 5 microns to 30 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 main body 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, 1.1 Polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, polyfluorinated ethylene, etc.), conductive particles (e.g. carbon black, silver particles, etc.) are coated on the plastic together with a suitable binder. , a substrate made of plastic or paper impregnated with conductive particles, a plastic containing 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 undercoat layer is casein, polyvinyl alcohol, nitrocellulose, ethylene-acrylic Nl:ff polymer, polyamide (nylon 6, nylon 66, nylon 6101 copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin, oxidized The thickness of the undercoat layer formed of aluminum or the like is suitably 0.1 micron to 5 micron, preferably 0.5 micron to 3 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, the surface of the charge transport layer must be positively charged, 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 with the unexposed area. .

A visible image can be obtained by developing the electrostatic latent image thus formed 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 power method may be any known method or methods, and are not limited to specific ones.

On the other hand, when the charge transporting material consists of a hole transporting material, it is necessary to charge the surface of the charge transporting layer negatively, and when it is exposed to light after being charged, the holes generated in the charge generation layer in the exposed area are transferred to the charge transporting layer. After that, it reaches the surface and neutralizes the negative charges, resulting in attenuation of the surface potential and an electrostatic contrast between it 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 specific example of the present invention is an electrophotographic photoreceptor containing the above-mentioned cyanine compound together with a charge transport substance in the same layer.

In this case, in addition to the above-mentioned charge transport substance, a charge transfer complex compound consisting of a trap compound IJ-N-vinylcarbashield trinitrofluorenone can be used.

The electrophotographic photoreceptor of this example can be prepared by dispersing or dissolving the aforementioned cyanine compound and charge transfer complex compound in a polyester solution in an appropriate organic solvent, and then forming a film thereon.

In any of the photoreceptors, the photoconductive composition used is selected from those containing a cyanine compound represented by the general formula (1), and in this case, it contains at least one type of cyanine compound, and if necessary In order to increase the sensitivity of the photoreceptor used, or to obtain a panchromatic photoreceptor, two or more cyanine compounds represented by the general formula (1) are combined, or a known cyanine compound is used. It is also possible to use it in combination with a charge generating substance selected from dyes and pigments.

The electrophotographic photoreceptor of the present invention can be used not only in laser printers but also in a wide range of electrophotographic applications such as RT printers.

Furthermore, the photoconductive composition of the present invention can also be used in solar cells and optical sensors in addition to the above-mentioned electrophotographic photoreceptor. Solar cells can be prepared, for example, by sandwiching the photoconductive compositions described above with indium oxide and aluminum.

Hereinafter, the present invention will be explained according to examples.

Example 1 Aqueous solution of casein in ammonia (11.2 g of casein, 1 g of 28% ammonia water)
1 water (222 mt) was coated by dip coating method and dried to form a coating amount of 1.0 g/-〇 undercoat layer.

Next, 1 part by weight of the above-mentioned compound (1) and 1 part by weight of butyral resin (Eslec BM-2, manufactured by Sekisui Chemical Co., Ltd.) were added to 30 parts by weight of isopropyl alcohol, and the mixture was stirred and dissolved. This solution was applied by dip coating onto the previously formed subbing layer and dried to form a charge generating layer. The film thickness at this time was 0.3μ. 6 Next, P-diethylaminobenzaldehyde-N-phenyl-N-α-naphthylhydrazone 1 part by weight, polysulfone resin (P 1700: manufactured by Union Carbide) 1 part by weight and 6 parts by weight of monochlorobenzene were mixed and dissolved by stirring with a stirrer. This liquid was applied onto the charge generation layer by dip coating and dried to form a charge transport layer.The film thickness at this time was 12μ.

A corona discharge of 15 KV was applied to the photoreceptor thus prepared. The surface potential at this time was measured (initial potential Vo).

Furthermore, the surface potential of this photoreceptor was measured after it was left in a dark place for 5 seconds (dark decay VW). Sensitivity is defined as the amount of exposure (El/
2 microjoules/,! ) was evaluated by measuring.

At this time, a gallium, aluminum/arsenic semiconductor (oscillation wavelength of 7 sonm) was used as a light source. These results were as follows.

vQ: -580 volts v,: 550 volts El/2: 12.5 microjoules/1 Examples 2 to 14 Compound s (g of the compound used in Example 1) was pressed down to form the compound shown in Table 1. A photoreceptor was prepared in exactly the same manner as in Example 1, except that each of these materials was used, and the characteristics of this photoreceptor were measured.The results are shown in Table 1.

1st Table 2 Compound Grave (2) -570-5'30
16.03 〃Fll+ -590-! U40 2
4.04 〃Ban (4) -580-54011,5s
tt A(5) -560-51013,86n A
+6)-6], 0-570 13.47 〃Bang (7)
-600-57017,88 Grave (81-590-55
019,79〃屓(9') -600-53036,4
10 Compound i(+o) -570-52020,4
11〃 Bian (ll) -560-53024,6
12tt s(m -570-53018,3
13n &(3B> -580-53038,
214n 4r14) 580 -550
23.4 Example 15 An ammonia aqueous solution of casein was coated on an aluminum plate with a thickness of 100 microns and dried to form a subbing layer with a thickness of 11 microns.

Next K, 2,4.7-dolinitro-9-fluorenone 52
and poly-N-vinylcarbazole (number average molecular weight 300
,000) 5F in tetrahydrofuran 70m, L
to form a charge transfer complex.

This charge transfer complex compound and the compound 1s' of the above-mentioned compound A(1) were mixed into polyester resin (Pylon: manufactured by Toyobo) 5f.
was added to a solution of 70 mt of tetrahydrofuran and dispersed. This dispersion was applied onto the subbing layer to a film thickness of 12 mm after drying.
It was applied to a micron thickness and dried.

The charging characteristics of the photoreceptor thus prepared were measured in the same manner as in Example 1. The results of this were as follows.

However, the charging polarity was set to ■.

Vo: 520 volts, 470 volts EIA: 25.4 microns 1φ Example 16 A polyvinyl alcohol film with a thickness of 1.1 microns was formed on the aluminum surface of an aluminum vapor-deposited polyethylene terephthalate film.

Next, the polyvinyl butyral solution containing the above-mentioned compound (1) used in Example 1 was applied to the previously formed polyvinyl alcohol layer using Mayer par so that the film thickness after drying was 0.5 microns. A charge generation layer was formed by coating and drying.

Next, the structural formula of pyrazoline compound 5? and Boaryaryl t4t1 fat (condensation polymer of bisphenol A and terephthalic acid-isophthalic acid) 52 and tetrahydrofuran 70? ? 1. A solution dissolved in L 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 of the photoreceptor thus prepared were measured in the same manner as in Example 1. The results of this first test were as follows.

Vo: -56 (1 port V, knee 520 volts E!, ”!: 9.4 microjoules/ct
4. As can be seen from the examples described above, the electrophotographic photoreceptor of the present invention has extremely high sensitivity characteristics in the wavelength range of 750 nm and below, and is excellent in charging characteristics such as initial potential and dark decay.

Patent applicant: Canon Co., Ltd. Agent: Patent attorney Gi Marushima

Claims (1)

[Scope of Claims] A photoconductive composition characterized by containing a compound represented by the following general formula (1). General formula (1) (wherein, Zl and Z represent a group of atoms necessary to complete a substituted or unsubstituted nitrogen-containing heterocycle. A1 and A represent a substituted or unsubstituted 5- or 6-membered ring. 2 f forming
llti hydrocarbon group. R1 and R represent a hydrogen atom or a substituted or unsubstituted alkyl group. Tori and Peng represent hydrogen atoms or halogen atoms. X represents an anion. m and n represent 0 or l, l represents l or 2'to)