JPS59170843A - Electrophotographic sensitive body - Google Patents

Abstract

PURPOSE:To obtain good sensitivity and decrease the fluctuation in the potential in a bright part and the potential in a dark part in repetitive electrostatic charging and exposing by providing a layer added with a specific hydrazone compd. CONSTITUTION:A layer added with the hydrazone compd. expressed by the formula is provided on an electrophotosensitive body. Such hydrazone compd. is used as an electric charge transfer material of the electrophotographic sensitive body of which, for example, the photosensitive layer is separated in function to an electric charge generating layer and an electric charge transfer layer. A soln. prepd. by dissolving such hydrazone compd. and a binder in a suitable solvent is coated and dried to form the charge transfer layer. The charge transfer layer may be laminated on the charge generating layer or may be laminated thereunder; the lamination on the charge generating layer is best preferred. Since the hydrazone compd. has a hole transferability, a positive chargeable toner is used. The photosensitive body contg. such charge transfer material has high sensitivity with the decreased fluctuation in the potential in the bright part and the potential in the dark part when used repeatedly and is used for not only a copying machine but a laser printer and photoengraving system, etc. as well.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to electron-q photoreceptors, and more particularly to electrophotographic photoreceptors having low molecular weight organic photoconductors that provide improved electrophotographic properties.

Conventionally, inorganic photoconductive materials such as selenium, domium sulfide, and zinc oxide have been known as photoconductive materials used in electrophotographic photoreceptors. These light-transmitting materials have many advantages, such as being able to be charged to an appropriate potential in the dark, having little charge dissipation in the dark, or quickly dissipating the charge when irradiated with light. On the other hand, it has various drawbacks. For example, selenium-based photoreceptors easily crystallize under conditions of temperature, humidity, dust, pressure, etc., and especially when the ambient temperature exceeds 40°C, crystallization becomes significant, leading to a decrease in chargeability and image distortion. Whenever white spots occur, there is a drawback. Cadmium sulfide photoreceptors do not have stable sensitivity in humid environments, and zinc oxide photoreceptors require the sensitizing effect of sensitizing dyes such as roseben gas. The disadvantage is that the sensitive dye cannot provide stable images over a long period of time because it suffers charging deterioration due to corona charging and photobleaching due to exposure light.

・－・How, zu! Various organic photoconductive polymers have been proposed using libinylcarnogzole, but these +4? Although IJ-mer is superior to the above-mentioned inorganic photoconductive materials in terms of film formation, t'H, lightness, etc., its practical application has been limited to date. hair,
Sufficient film forming properties have not yet been obtained, and/or? :,sensitivity,
This is because they are inferior to inorganic photoconductive materials in terms of durability and stability against environmental changes. In addition, hydrazone compounds disclosed in U.S. Pat. No. 4,150,987, triarylpyrazoline compounds described in U.S. Pat. Organic light of low molecular weight compounds such as 9-styryluane] and helix compounds described 4
An electric body has been proposed. These low-molecular-weight organic photoconductors have been able to overcome the film-forming defects that had been a problem in the field of organic photoconductive polymers by appropriately selecting the binder used. , cannot be said to be sufficient in terms of sensitivity.

For this reason, in recent years, a 7'c laminated structure has been proposed in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer. Electrophotographic photoreceptors using this laminated structure as a photosensitive layer can now be improved in terms of sensitivity to visible light, charge retention, surface strength, etc.

Such an electrophotographic photoreceptor is disclosed in US Pat. No. 58!1, for example.
This method is disclosed in Japanese Patent No. 7851, Publication No. 3871882, and the like.

However, electrophotographic photoreceptors using conventional low-molecular-1 organic photoconductors in the charge transport layer have not yet been able to achieve seven-fold sensitivity, and when repeatedly tested and exposed, There are large fluctuations between the bright and dark potentials, and the photomemory properties should be greatly improved.

It is an object of the present invention to provide a photoreceptor that eliminates the above-mentioned drawbacks or disadvantages of the present invention.

Another object of the present invention is to provide a novel organic photoconductor.

Another object of the present invention is to provide a novel charge transport material in a laminated photosensitive layer in which a charge generation layer and a charge transport layer are functionally separated.

This object of the present invention is achieved by an electrophotographic photoreceptor having a layer containing a hydrazone compound represented by the following general formula (1).

General formula 1) /KodaL In the formula, R4 and R2 are methyl, ethyl, propyl,
Alkyl groups such as butyl, benzyl, phenyl, aralgyl groups such as naphthylmethyl, phenyl groups, 7-alkyl groups include alkoxy groups such as methoxy, ethoxy, -7'rj, butoxy, fluorine, chlorine, bromine. , may be substituted with a halogen atom such as iodine, or a dialkylamino group such as dimethylamino, diethylamino, dipropylamine, dibutylamino, etc., a nuclear aralkyl group, the phenyl group is an alkyl group such as methyl, ethyl, propyl, butyl, etc. It may be substituted with an alkoxy group such as chlorine, methoxy, ethoxy, probogyin, or butoxy, a halogen atom such as fluorine, chlorine, bromine, or iodine, or a dialkylamino group such as dimethylamino, diethylamine, dipropylamino, or dibutylamino. Further, Rj and R2 are residues that together with the N atom form a 5- to 6-membered ring group such as a pyrrolidyl group, a piperidyl group, or a morpholino group.

R3 and R4 represent an alkyl group such as methyl, ethyl, propyl, butyl, an aralkyl group such as benzyl, phenethyl, naphthylmethyl, or an aryl group such as benzene, naphthalene, anthracene, etc., and the alkyl group and aryl group have a substituent. The 'lt substituent includes the same substituents as the aralkyl group and phenyl group in Ri and R2.

Ar1. Ar2 is the same or different and represents an arylene group such as phenylene, naphthylene, anthrylene, etc., and the arylene group is an arylene group such as methyl, ethyl, propyl, butyl, an alkoxy group such as methoxy, ethoxy, propoxy, butoxy, fluorine, It may be substituted with a halogen atom such as chlorine, bromine, or iodine.

'Ol', O)
To Ol) 1)
1) 1) Tatsugi shows a synthesis example of the above compound.

H-1 Compound N-phenyl-α-naphthylamine 64.79 (0,2
95 mol), ethanol 550mA, acetic acid 350m7!
22.4y (0,325 mol) of sodium nitrite was added over 20 minutes while stirring at room temperature, and then 67.5F (1,03 mol) of zinc powder was added to the solution at a temperature of 2.
Addition was made in 60 minutes while adjusting the temperature to 0 to 35°C. After adding the zinc powder, stir for 40 minutes and remove unreacted zinc and precipitated crystals from door to door.
01.51 (0,266 mol) as methanonyl 3DOm
1 was added dropwise to the solution under stirring at room temperature to precipitate a large amount of yellow powdery precipitate. Methyl ethyl ketone 1 after offshore removal
60- was recrystallized to obtain 66.5f of yellow crystals of the target 2(-1 compound. Yield: 45.5cm.

Elemental analysis Molecular formula C59H37N3 Calculated value Analytical value C85,585,77 H6,81672 N 7.67 7.51 In a preferred embodiment of the present invention, an electrophotographic photoreceptor in which the photosensitive layer is functionally separated into a charge generation layer and a charge transport layer is used. A hydrazone compound represented by the general formula (1) above can be used as the charge transport material.

The charge transport layer according to the present invention is preferably formed by applying a solution prepared by dissolving the hydrazone compound represented by the above-mentioned general formula (1) and a binder in a suitable solvent and drying the solution. Examples of the binder used here include polyarylate resin, polysulfone resin, polyamide resin, acrylic resin, acrylonitrile resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, phenol resin, epoxy resin, polyester resin, alkyd resin, and polycarbonate. , polyurethane, or copolymer resins containing two or more repeating units of these resins, such as styrene-butadiene copolymer, styrene-methacrylic copolymer, and styrene-maleic acid copolymer. In addition to such insulating polymers, organic photoconductive polymers such as polyvinylcarbazole, polyvinylanthracene, and polyvinylpyrene can also be used.

The blending ratio of the binder and the hydrazone compound is preferably 1 part of the binder and 10 to 500 parts of the hydrazone compound.

The charge transport layer is electrically connected to the charge generation layer below, and has the function of receiving and receiving charge carriers injected from the charge generation layer in the presence of a quasi-field, and transporting these charge carriers to the surface. I have. At this time, this charge transport layer may be laminated on one and seven of the charge generation layers,
It may be laminated on F of the trench. However, it is preferable that the charge transport layer is laminated on the charge generation layer. Since this 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.

The organic solvent used when forming such a charge transport layer is
The binder varies depending on the type of binder used, and it is preferable to select one that does not dissolve the charge generation layer or underlying subbing layer. Specific idH agents include ketones such as acetone, methyl ethyl ketone, and cyclohexanone, N,
Amides such as N-dimethylformamide, N,N-u methylacetamide, sulfoxides such as dimethyl sulfoxide, ethers such as tetrahydrofuran, dioxane, ethylene glycol monomethyl ether, esters such as methyl acetate and ethyl acetate, chloroform, chloride Aliphatic and helocarinated hydrocarbons such as methylene, dichloroethylene, carbon tetrachloride, trichlorethylene, benzene, toluene, xylene, ligroin,
Aromatic compounds such as monochlorobenzene and dichlorobenzene can be used.

Coating methods include dip coating, spray coating, spinner coating, bead coating,
This can be carried out using a coating method such as a Mayer bar coating method, a Fleid coating method, a roller coating method, or a curtain coating method. For drying, it is preferable to dry to the touch for 4 hours at room temperature and then heat dry. Heat drying at a temperature of 30℃ to 200℃ for 5 minutes.
The charge transport layer of the present invention may contain various additives. 3. Seven such additives include diphenyls, 'li-terphenyl, 0-terphenyl,
P-terphenyl, dibutyl phthalate-1, dimethylgelicol phthalate, dioctyl phthalate), l-
Liphenyl phosphoric acid, methylnaphthalene, benzophenone,
Chlorinated rough in, dilaurylnamezolobionate, 3
．． Examples include 5-:5 nitrosalicylic acid and various fluorocarbons.

The charge generation layer used in the present invention includes selenium, selenium/neutral, pyrylium, thiopyrylium dyes, phthalocyanine pigments, anthanthrone pigments, dibenzpyrenequinone pigments, pyranthrone pigments, trisazo pigments, disazo pigments, azo pigments, and indigo pigments. , quinacrytone type, asymmetrical quinocyanin, quinocyanin or JP-A-5
A separate vapor deposited layer or resin dispersion layer selected from charge generating materials such as amorphous silicon as described in Japanese Patent No. 4-145645 may be used.

Examples of the charge generating substance used in the electrophotographic photoreceptor of the present invention include the following inorganic compounds and organic compounds.

Charge-generating substances (1) Amorphous silicon (2) Selenium-tellurium (6) Selenium-arsenic (4) Cadmium sulfide (56) (57) (58) Square link acid methine dye (59) Indigo dye (0,1,NO, 780flO)
(ω) Thioindigo dye (c, ■, Fly78800) (
61) β-type copper phthalocyanine (62) (65) (64) (θ5) To prevent charge generation, add a portion of the charge-generating substance described above to a suitable binder, and apply this onto the substrate. Particularly in form 1
It can also be obtained by forming a vapor deposited film using a vacuum evaporation device. The binder 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 Nanki photoconductive polymers such as poly-N-vinylcarbazole, polyvinylanthracene, and polyvinylpyrene. can. Preferably, polyvinyl butyral, polyarylate (condensation polymer of bisphenol A and phthalic acid, etc.), polycarbonate, polyester, phenoxy resin, polyvinyl acetate, acrylic resin, polyacrylamide resin, polyamide, polyvinylpyridine, cellulose type Examples include insulating resins such as resin, urethane resin, epoxy resin, casein, polyvinyl alcohol, and polyvinylpyrrolidone. 4
The resin contained in the load generating layer is 80% by weight or less, preferably 1
7< is suitably 40% by weight or less. Examples of organic solvents used during coating include alcohols such as methanol, ethanol, and isopropanol, and 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,
Aliphatic or halogenated hydrocarbons such as methylene chloride, dichloroethylene, carbon tetrachloride, and trichlorethylene, or aromatics such as benzene, toluene, xylene, ligroin, monochlorobenzene, and dichlorobenzene can be used.

Coating methods include dip coating method, spray coating method, spinner coating method, bead coating method,
This can be carried out using the Mayer-Par coating method, the plate coating method, the roller coating method, the curtain coating method, and the conventional coating method.

In order to obtain sufficient absorbance, the charge generation layer contains a large amount of photoconductor and the generated 'L'.
In order to shorten the range of the cargo carrier, it is preferable to use a thin film layer, for example, a thin film layer of 5 microns or less, preferably 7 (H4F, 01 microns to 1 micron). This means that most of the incident light is absorbed by the charge generation layer, generating a large amount of charge gear.
Furthermore, this is due to the fact that it is necessary to inject the generated charge carriers into the charge transport layer without being deactivated by recombination or trapping.

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, /cinadium, molybdenum, chromium, titanium, nickel, indium, gold, platinum, etc. can be used, and in addition, aluminum, aluminum alloy, indium oxide, tin oxide, indium oxide can be used. - Plastics (e.g., polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, polyethylene 7tate, etc.) having a layer formed of a tin oxide alloy or the like by vacuum deposition, conductive particles (e.g.,
carbon blank, silver particles, etc.) as appropriate. In addition to Ingu, a substrate coated on plastic, 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 subbing layer is casein,
Polyvinyl alcohol, nitrocellulose, ethylene-
Acrylic acid copolymer, polyamide (nylon 6, nylon 66, nylon 610, copolymerized nylon, alkoxymethylated nylon, etc.), polyurethane, gelatin,
It can be formed from aluminum oxide, etc.

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

When using a photoreceptor in which a conductive layer, a charge generation layer, and a charge transport layer are laminated in this order, it is necessary to negatively charge the surface of the charge transport layer because the hydrazone compound has hole transport properties. In the exposed area, holes generated in the charge generation layer are injected into the charge transport layer, and then reach the surface to neutralize the negative charges, resulting in attenuation of the surface potential and an electrostatic contrast between the layer 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.

In another specific example of the present invention, the above-mentioned disazo pigment or pyrylium dyes, thiapyrylium dyes, selenapyrylium dyes, and benzopyrylium dyes disclosed in U.S. Pat. No. 3,554,745, U.S. Pat. , benzothiapyryllium dyes, naphthopyryllium dyes, naphthothiapyrylium dyes, and other pigments and dyes having light guiding properties can also be used as sensitizers.

In another specific example, a eutectic complex of a pyrylium dye and an electrically insulating polymer having an alkylidene diarylene moiety, as disclosed in US Pat. No. 5,684,502, can also be used as a sensitizer. This eutectic complex is, for example, 4
-[4-bis-(2-10loethyl)aminophenyl)
-2,6-diphenylthiapyrylium glycolate topoly(4,4'-impropylidene diphenylene carbonate) in a helocarinated hydrocarbon solvent (e.g.
Dichloromethane, chloroform, carbon tetrachloride, 1.1-
:, 5 chloroethane, 1,2-dichloroethane, 1
, 1.2-) dichloroethane, chlorobenzene, fromobenzene 1.2-u chlorobenzene>), and then add a non-polar solvent (e.g. hexano, octane, decane, 2,2.4-trinotylbenzene, ligeroin) to this. A particulate eutectic complex is obtained by adding styrene to the electrophotographic photoreceptor in this specific example.
Butadiene copolymer, silicone resin, hinyl resin, vinylidene chloride-acrylonitrile copolymer, etc. can be contained as a binder.

The electrophotographic photoreceptor of the present invention can be used not only for electrophotographic copying machines, but also for laser printers, CRT 7? +,
It can also be widely used in electrophotographic application fields such as 1-interface, electrophotographic plate making system fx, and g.

According to the present invention, it is possible to provide an electrophotographic photoreceptor with high sensitivity, and it has the advantage that fluctuations in bright area potential and dark area potential are small when charging and exposure are repeated.

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

Example 1 β-type steel phthalocyanine (trade name L) manufactured by Toyo Ink Manufacturing ■
i0nOI Blue NOB TOrosr) was sequentially refluxed in water, ethanol and benzene, and purified by filtration.Product name: Polyester Adhesive 49,000 (solid content 20%), manufactured by DuPont, 14?
, toluene 557, dioxane 55? A coating solution was prepared by mixing and dispersing in a ball mill for 6 hours. This coating solution was applied to an aluminum sheet until the dry film thickness was 0.
A charge generation layer was prepared by coating with a Mayer bar to a thickness of 5 microns.

Next, the above-mentioned exemplary compound H-2 was added as a charge transport compound to 8
1 and the product name of polycarbonate resin (Teijin Kasei ■) [
Panlight -1300J 7? A solution obtained by stirring and dissolving the above in a mixed solvent of tetrahydronorane 651 and chlorobanzene 35F was applied onto the charge generation layer using a Meyer Parr so that the dry film thickness was 11 microns. 2
An electrophotographic photoreceptor with a photosensitive layer consisting of a layered structure was prepared.

The electrophotographic photoreceptor thus prepared was statically charged with corona at 15 KV using an electrostatic copying paper tester Model 18P-428 manufactured by Kawaguchi Denki, held in a dark place for 10 seconds, and then charged at an illuminance of 5 lux. It was exposed to light and its charging characteristics were investigated.

As for the charging characteristics, the surface potential (vO) and the potential (Vlo) after 10 seconds of dark decay were measured, and the bright area potential after repeated use was measured. In order to measure the changes in the dark potential, the photoreceptor produced in this example was charged with a -5.6 KV corona charger,
It was attached to the cylinder of an electrophotographic copying machine equipped with an exposure optical system with an exposure time of 101 ux-sec, a developing device, a transfer charger, a slat removal exposure optical system, and a cleaner.

This copying machine is configured to obtain an image on transfer paper-F as the cylinder is driven. Using this copying machine, the initial bright area potential (VL), dark area potential (Vc) and
The light area potential (V'L) and dark area potential (c VD) after 1,000 uses were measured. The results are shown below.

Vo: -595 volts Vlo: -585 volts E! A: 2.71ux@sec Initial VD-6 after 5000 durability
50 volt vI, -ss volt VD-635 pol) VL-45 volt Examples In each of Examples 2 to 1, Exemplified Compound a-2 was replaced with Exemplified Compound a-2 as the charge transport compound used in Example 1. H-
1, H-6, H-4, H-5, H-6, H-7, H-9
, H-10, H-12, H-14,! (-15, H-1
Electrophotographic photoreceptors were prepared in the same manner as in Example 1, except that Samples No. 6, H-18, H-19, and H-20 were used.

The electrophotographic properties of each photoreceptor were measured in the same manner as in Example 1. The results are shown below.

2 H-12, 25905856H-ro
Ro, 1 565 5554 I
(-42,658558゜5 H-52,95
755656H-64, 2595595 7H-75, 2600590 8H-9S5 565 5609
H-102,757056010HI3 4.
4 565 55511 H-1
42,557557゜12 H-152,95
5554513H-”16 2.1 56
0 54514 H-182,1590
58515I (-191,956,0545 16H-202,3575570 26602065025 3, 6353063035 46552565055 56453064o 35 6 665 40 650 457
670 50 655 558
635 35 625 459
640 25 630 Ro010
6!15 40 61D 5
011 625 25 620
5512 6ro0 50 615
Ro51ro 650 20 615
4014 660 20 640
5515 6ro D 15 615
5016 645 20 625
40 Example 17 4-(4-s-j methylaminophenyl) -2,6-
Siphenylthiapyrylium Pechlorate 61 and the above-mentioned hydrazone compound H-85t were mixed into polyester plum fat (Polyester Adhesive 49000: manufactured by DuPont).
100 r of toluene (50)-dioxane (50) solution of
RI! and dispersed in a ball mill for 6 hours. This dispersion was coated onto a 1 um aluminum sheet using Mayano ζ- so that the film thickness after drying was 15 microns.

Example 1 The electrophotographic characteristics of the photoreceptor produced in this way
It was measured in the same manner as. This unity is shown below.

VO: -560 volts V1t+: -5L55-1 Iruto Hiro:
5. O1ux-θθC Initial VD: -630 volts; 5D volts VD after 5,000 cycles: -610 volts VL: -45 volts Example 18 An ammonia aqueous solution of casein (casein 1) was placed on an aluminum plate.
1.2j', 28q6 ammonia] water 1? , water 222m
1. ) was coated with a Mayer bar and dried to form an adhesive layer with a thickness of 1 micron.

Next, a disazo pigment 51 having the following structure and a butyral resin (a degree of butyralization of 6 mmolti) 22 were mixed with ethanol 9
After dispersing with the liquid dissolved in 5-, it is coated on the adhesive layer to form a charge generation layer having a thickness of 0.4 ha after drying.Next, the above-mentioned hydrazone compound H-115 is applied.
r and poly-4,4'-dioxydiphenyl-2,2'-
Zoloban carbonate (viscosity average molecular weight, 5oooo
>52 dissolved in 150 g of dichloromethane is applied onto the charge generation layer and dried to give a film thickness of 11 microns. d) An electrophotographic photoreceptor is produced by forming a transport layer.

Electrophotograph A7 of the electrophotographic photoreceptor created in this way
1? The 3° strength was measured in the same manner as in Example 1.The results were then measured at 7J.

11o: -1600 Boles 1・■
+o: -595 Volts, 2: 3. +1ux-sec First month V, : -6711 Volt vL Knee 35 Volt Giant Horse - 9 row Endurance VD : -660 Port VL '50' 5 Rut Example 19 0, 2 mm thickness with surface cleaned molybdenum plate (
(substrate) was fixed at a predetermined position in a glow vapor deposition tank. Next, the tank was completely evacuated to a vacuum level of about 5 x 10'' torr. Thereafter, the input voltage of the heater was increased to stabilize the molybdenum substrate temperature f: 150°C. After that, hydrogen gas and silane gas (15 volumes per hydrogen gas) were introduced into the tank, and the gas flow rate and the main valve of the deposition tank were adjusted to 0.5
It was stabilized at torr. Next, 5 MHz high frequency power was applied to the induction coil to generate glow discharge inside the coil in the tank, resulting in an input power of 30 W. An amorphous silicon film was grown on the substrate under the above conditions, and the same conditions were maintained until the film thickness reached 2 microns, after which glow discharge was discontinued. After that, turn off the heating heater and high-frequency power supply, wait for the substrate temperature to reach 100°C, close the hydrogen gas and silane gas outflow/globe, and temporarily reduce the temperature inside the tank to 10 torr.
After the temperature was reduced to below, the pressure was returned to atmospheric pressure and the substrate was taken out. Next, a charge transport layer was formed on this amorphous silicon layer in exactly the same manner as in Example 1 except that Exemplary Compound H-16 was used as the charge transport compound.

The photoreceptor obtained in this way was installed in a charging exposure experimental device, and θ
It was corona charged at 6 Kv and immediately irradiated with a light image. The light image was illuminated through a transmission type test chart using a tungsten lamp light source.

Immediately thereafter, a good toner image was obtained on the surface of the photoreceptor by cascading a charged developer (containing toner and carrier) onto the surface of the photoreceptor.

Example 20 4-(4->methylaminophenyl)-2,6--diphenylthiavirylium perchloride 1-57 and i(
414'-Isopropylidene diphenylene carbonate) 3r must be fully dissolved in fR to dichloromethane 200d, toluene 1007! was added to precipitate the eutectic complex.

After this precipitate was separated in a furnace, dichloromethane was added to redissolve it, and then n-hexane 100- was added to the solution to obtain a precipitate of a eutectic complex. , This eutectic complex 5? was added to 95 ml of a methanol solution containing polyvinyl butyral 2f, and dispersed in a ball mill for 6 hours. This dispersion was applied onto an aluminum plate having a casein layer using a Mayer bar to form a charge generation layer so that the film thickness after drying was 0.4 microns.

Next, a cover layer of a charge transport layer was formed on this charge generation layer in exactly the same manner as in Example 1 except that Exemplary Compound H-17 was used.

The electrophotographic properties of the photoreceptor thus prepared were measured in the same manner as in Example 1. The results are shown below.

VQ: -6io volts Vlo: -605 volts Hiroshi: 2.01ux1eθc Handling -M- VD: -680 volts VL: -25 Bordeaux Kawakamisen Kaifukyumai VD: -655 volts vL: -40 volts Example 21 The same eutectic complex 52 used in Example 20 and the above-mentioned hydrazone compound H-25f were mixed with a polyester resin (
Polyester Adhesive 49000 (manufactured by DuPont) in addition to Tetrahydrofusin Solution 150-, thoroughly mixed and stirred. It was applied like this.

The electrophotographic properties of this photoreceptor were measured in the same manner as in Example 1. The results are shown below.

vO: -570 volts V1o: -560 volts To: 2.11ux-sec initial vD: -640 volts vL: -25 Vold ー〉、Matsu」ya vD: -625 volts vL: -45 volts Patent applicant: Canon Co., Ltd.

Claims (1)

[Scope of Claims] An electrophotographic photoreceptor comprising a layer containing a hydrazone compound represented by the following general formula (1). General formula (1) However, in the formula, R1 and R2 are an alkyl group that may have a substituent, an aralkyl group, a phenyl group, or a 5 to N atom.
The remainder forming a 6-membered ring is shown, and R3 and R4 are an alkyl group, an aralkyl group, or an aryl group which may have a substituent. Ar4, Ar2 and Ar5 represent arylene groups which may have the same or different substituents.