JPS5852647A - electrophotographic photoreceptor - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an electrophotographic photoreceptor, and more particularly to an electrophotographic photoreceptor having a photosensitive layer containing a novel organic photoconductive substance comprising a hydrazone compound.

Conventionally, the light guide area (as a material) used in Yuko photoreceptors is
Inorganic photoconductive materials such as selenium, cadmium sulfide, and lead 111j oxide are known. These photoconductive materials are
Although it has many advantages, such as being able to be charged to an appropriate potential in the dark, having little charge dissipation in the dark, and being able to quickly dissipate the charge by irradiation with a cow, it also has various drawbacks. are doing. For example, in a selenium-based photoreceptor, crystallization easily progresses due to factors such as temperature, humidity, dust, and direction, and especially when the atmospheric width exceeds 40°C, crystallization becomes significant, resulting in a low density band. There are drawbacks such as white spots appearing on images. Warped selenium-based photoreceptors and cadmium sulfide-based photoreceptors have the disadvantage that stable sensitivity and durability cannot be obtained when used over time under high humidity.

In addition, salivary lead oxide-based 118 photons require the sensitizing effect of sensitizing dyes such as rose bengal, but such sensitizing dyes cause charging deterioration due to corona charging and photobleaching due to exposure light. Unfortunately, it has the disadvantage that it cannot provide stable images over a long period of time.

On the other hand, various organic photoconductive polymers including polyvinylcarbazole have been proposed, but these polymers are superior in terms of film formability and lightness compared to the inorganic photoconductive materials mentioned above. However, it has been difficult to put it into practical use to date because sufficient film formation properties have not yet been achieved, and inorganic photoconductive materials have been lacking in sensitivity, durability, and stability against environmental changes. This was because they were inferior in comparison. In addition, triarylpyrazoline compounds described in U.S. Patent No. 3,837,851, etc., and U.S. Pat.
Low-molecular organic photoconductive materials have been proposed, such as the hydrazone compound described in Publication No. 7 and British Patent No. 930988, and the 4-chlorooxazole compound described in JP-A No. 1@55-53278. has been done. By appropriately selecting the binder used, the outstanding low-molecular-weight organic photoconductive materials can overcome the shortcomings that have plagued the field of organic photoconducting polymers ( 1, but it cannot be said to be sufficient in terms of sensitivity.

The purpose of the present invention is to create a new '11L child photoshooter 11 & light body 11 that eliminates the disadvantages of 't3fl4.
- It is about providing.

Another object of the present invention 41 is to provide a novel organic photoconductive material.

Another object of the present invention is to provide a compound suitable for use as a camphor material for use in a photosensitive layer consisting of an M-layer structure of d1, 'NT, both generation layers and a heavy transport layer.

The second object of the present invention is to form a layer containing a hydrazone compound represented by the general formula (1) by an electrophotographic photoreceptor at 11°.

1't.

In the formula, 12 digits, hydrogen atom, substituted or unsubstituted alkyl group (e.g., methyl group, ethyl group, propyl group, 1so-propyl group, butyl group, t-butyl group,
amyl group, t-amyl group, octyl group, 2-ethylhexyl group, 2-hydroxyethyl group, 2-methoxyethyl group, 2-chloroethyl group, 3-hydroxypropyl group,
3-mei-xypropyl group, 4-methoxybutyl group, 3
-sulfopropyl group, etc.), substituted or unsubstituted aralkyl groups (e.g., benzyl group, phenethyl group, α-naphthylmethyl group, chlorobenzyl group, dichlorobenzyl group, trichlorobenzyl group, ethylbenzyl group, methoxybenzyl group, cyano benzyl group, etc.) or substituted or unsubstituted aryl groups (e.g., phenyl group, tolyl group, xylyl group, biphenyl group, ethylphenyl group, methoxyethyl group, dimethoxyphenyl group, chlorophenyl group, dichlorophenyl group, trichlorophenyl group, cyano Phenyl group, N,N-di-methylaminophenyl group, N,N-diethylaminophenyl X,, N,N-di-
propylaminophenyl group, N,N-dibenzylaminophenyl group, morpholinophenyl group, piperazinophenyl group, pyrrolidinophenyl group, etc.).

A represents a heterocyclic group, preferably represented by the following general formula (a)
, (+)) , (c) and (d).

General formula % Formula % ■ R5 and R are substituted or unsubstituted alkyl groups (e.g., methyl group, ethyl group, n-propyl group, 1so-
Propyl group, n-butyl group, 5ec-butyl group, t-butyl group, n-amyl group, 5ec-'amyl group, t-amyl group, n-hexyl group, 2-ethylhexyl group, n-octyl group, 2 -Hydroxyethyl group, 3-hydroxypropyl group, 2-chloroethyl group, 3-1' loloprobyl group, 2-methoxyethyl group, 3-methoxypropyl group,
3-ethoxypropyl group, 3-cyanopropyl group, etc.)
shows.

R represents a substituted or unsubstituted alkyl group (eg, methyl group, ethyl group, propyl group, is.

-propyl group, butyl group, t-butyl group, amyl group, t
-Amyl group, octyl group, 2-ethylhexyl group, 2-
hydroxyethyl group, 2-methoxyethyl group, 2-chloroethyl group, hydroxybrobyl group, 3-methoxyphenyl group, 4-methoxybutyl group, 3-sulfopropyl group, etc.), substituted or unsubstituted aralkyl group ( For example, benzyl group, phenethyl group, α-naphthylmethyl group, chlorobenzyl group, dichlorobenzyl group, trichlorobenzyl group, ethylphenyl group, methoxyethyl group,
cyanobenzyl group, etc.) or a substituted or unsubstituted aryl group (e.g., phenyl group, tolyl group, xylyl group, biphenyl group, ethylphenyl group, methoxyphenyl group, dimethoxyphenyl group, chlorophenyl group, dichlorophenyl group, trichlorophenyl group, Dianophenyl group, N,N-di-methylaminophenyl group, N,N-diethylaminophenyl JA, N,N-thieflobylaminophenyl group, N,N-diethylaminophenyl group,
morpholinophenyl group, piperazinophenyl group, pyrrolidinophenyl group, etc.). Kawa is an optionally substituted aryl group (e.g., phenyl group, tolyl group, xylyl group, biphenyl group, ethylphenyl group, methoxyphenyl group, dimethoxyphenyl group, chlorophenyl group, dichlorophenyl group, trichlorophenyl group, cyanophenyl group) , N, N-di-methylaminophenyl group, N, N-
diethylaminophenyl-s, N, N-/-propylaminophenyl group, N, N-dibenzylaminophenyl group, morpholinophenyl group, piperazinophenyl group, pyrrolidinophenyl group). X is a hydrogen atom or a halogen atom (e.g., chlorine atom, bromine atom, etc.)
shows.

Z2 is a 2-pyridine ring, a 4-pyridine ring, a 2-quinoline ring, a 4-quinoline ring, a thiazoline ring, a thiazole ring,
Benzothiazole ring, naphthothiazole ring, oxazoline ring, ogisazole ring, benzoxazole ring, naphthoxazole ring, selenazole ring, benzoselenazole ring, naphthoselenazole ring, imidacilline ring, imidazole ring, benzimidazole ring, nandoimidazole ring, indoline Indicates the atomic group necessary to complete a 5- or 6-membered heterocycle such as a ring. Further, l is 0 or 1.

These heterocycles include halogen atoms such as chlorine atom, bromine atom, and iodine atom, methyl group, ethyl group, n-propyl group, 1so-propyl group, n-butyl group, 5ec-butyl group, l-butyl III; , n-amyl group, argyl group such as t-amyl group, n-hydroxyethyl group, 3-hydroxypropyl group, 2-methoxyethyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-cyanopropyl group Substituted argyl groups such as benzyl groups, aralkyl groups such as phenethyl groups, aryl groups such as phenyl groups, tolyl groups, xylyl groups, biphenyl groups, chlorophenyl groups, dichlorophenyl groups, trichlorophenyl groups, cyanophenyl groups, hydroxyphenyl groups It can be IM-converted by a substituted phenyl group such as a nitrophenyl group, a carboxyphenyl group, a sulfophenyl group, a nitro group, an ano group, a hydroxy group, an amine group, etc.

Z3 represents -8- group, -0-1 or >CI-■2 group.

Z, K, heterocycle (e.g., thiazoline ring, thiazole ring, benzothiazole ring, naphthothiazole ring, oxazole ring, oxazoline ring, penzoxazole ring, naphthoxazole ring, imidazole ring, benzimidazole ring, naphthoimidazole ring, benzoselenazole ring,
(naphthoselenazole ring, indoline ring, 2-quinoli/ring, 4,-quinoline ring, 2-pyridine ring, 4-pyridine ring, triazole ring, thiadiazole ring, inbenzimidazole ring, inbenzimidazole ring, etc.) Indicate the atomic groups required for These heterocycles include halogen atoms (for example, chlorine atoms, bromine atoms, iodine atoms, etc.),
Alkyl groups (e.g., methyl, ethyl, propyl, butyl, amyl, octyl, etc.), alkoxy groups (e.g., methoxy, ethoxy, propoxy,
butoxy group), aryl group (e.g. phenyl group,
tolyl group, xylyl group, chlorophenyl group, bromophenyl group, etc.), nitro group, cyano group, hydroxy group, amine 7 group, algylamino group (row, N-methylamino group, N-ethylamino 7%, N -propylamino group,
N,N-methylamino group, N,N-diethylamino group, N,N-dipropylamino group, etc.).

Also, nl:0,17 indicates r12, and mke〇-sat or 1.

Representative examples of the hydrazone compound represented by the general formula (1) are shown below.

Examples of hydrazone compounds Compounds in which A corresponds to general formula (a): (1) 113 021T! o, ir.

(6) ■ 0,H.

211m 2115 (9) 02)(.

113 Amane CH3 (16) (17) CH3 c2f-1゜ ■ C) 211° (22) Chi 0.11° ■ 02)(,OOH.

2N5 02I-1゜ 0,H.

1 02H400H.

day of the week C2H.

(37) ■ 0211° 02tr.

(45) 0)f
.

■ 02H.

(48) OH.

02H.

(49) 01-I.

011° C21(.

(52) H3 1 C2If.

(54) 0, H3 0□H6 021-1゜ 021-T.

02I-1゜ ■ 021(40(!If3 (32H.

02H.

0I(.

Compound where A corresponds to general formula (I): OH3U211
' (69) (70) (71) (72) (73) Shou02H,00H3 (76) (77) (78) Chemical +//J where A is represented by the general formula (C): (92) O
ff.

1 (93) Ol-1°N
-01-(02I-I.

tJ 2 tj 5 (97), 1.3 (98
) Compound in which 0ti3021-1°A is represented by the general formula (d): 0H.

(102) OH3 02Ll.

(103) Oh.

02H.

(104) 0l-Ts 011° (106) 113 ■ C! 113 ― 011° (110) 1 021T.

(Ko, I-T, 011 021-T.

021-I, 0H (117) Oh.

These hydrazone compounds can be used alone or in combination of two or more.

These compounds are composed of a heterocyclic hydrazine represented by the general formula % (wherein R1, Z (and
1 (, and n tj:, FIfT Rself and times-pox Wt
It is 4. ) can be easily synthesized by conventional methods once a month.

Next, specific synthesis examples will be described.

Synthesis Example 1 (Compound of yii 2 above) Hydrazone geoacid jM 4.6 f (0,
02 mol) and 2-formylthiazole 24y (0,02 mol)
mol) was stirred for 30 minutes in a mixed solvent of 70 ml of methanol and 50 ml of water to react. The reaction solution was injected into the dog's water to neutralize it, then filtered and dried. This solid was recrystallized from ethanol to obtain crystal 442 (yield 76).

Elemental analysis: 013H1t N482 (w value) Experimental value (9 g) 0 54.17 54.12 H4,174,14 N 19.44 19.47 Synthesis example 2 (compound of /1616 above) Hydrazone represented by C2H de 4.8f (0.02 mol) of the hydrochloride and 3.71 (0.02 mol) of 2-formylbenzothiazole were stirred for 30 minutes in a mixed solvent of 70° of methanol and 5° of water to react.

After neutralizing the reaction solution with water, it was filtered and dried.

This solid was recrystallized with ethanol to obtain 4.9f crystals (yield: 71 mm).

Elemental analysis: 02oH2ON, 8 Calculated value (crab) Experimental value (piece 0 68.97 61'!, 92H5,75
5,78 N ], 6.09 16.07 Synthesis Example 3 (Compound of Compound 66) 021 ].

Hydrochloric acid JU of hydrazone, 4.69 (0,0
2 mol) and 3-formyl-1O-methylnoenothiazine 4.8 F (0.02 mol) were pressed for 4'yL for 30 minutes in a mixed solvent of 70 methanol and 507 ml of water, and the reaction stopped. . The reaction solution was washed with water, filtered, and dried.

This solid was crystallized from ethanol for 11 seconds (yield: 6
4 recitations).

Elemental analysis: h, ', 30□31-12+I N48
2 Calculated value (%) Experimental value (96) 0 66, 35 ti 6.331-■4.8
1 4.85 N 13.46 13.48 Synthesis Example 4 (Compound A85) 02H.

hydrazone hydrochloride 3.6y (o, 02 mol) and 3-formyl-9-ethylcarbasol 4.7f (
0.02f) was reacted in the same manner as in Synthesis Example 1 to obtain a reaction solution. This reaction solution was neutralized with water, filtered, and dried.

This solid was recrystallized from ethanol. As a result, 5.
Crystals of 6r (yield 81%) were obtained.

Elemental analysis: 0. oH2oN4S Calculated value (π) Experimental value (%) 0 68.97 68.94H5,755,
72 N 16.09 16.12 Synthesis Example 5 (Compound 101) ■ OH.

3.3f (0.02 mol) of hydrazone hydrochloride shown by and 4.79 (0.02 mol) of 1-methyl-2-phenyl-6-formylbenzothiazole were reacted in the same manner as in Synthesis Example 1. A reaction solution was obtained.

After neutralizing this reaction solution with water, it was subjected to P-oxidation and dried. This solid was recrystallized from ethanol. This result 5.2
A crystal of f (yield 759K) was obtained.

Elemental analysis: (L3., II, 7N, S value (%)
Experimental value (%) 0 65, 71 65.751-1
4.90 4.88N 20.17
2f-1,14 Other hydrazine compounds used in the present invention can be synthesized in the same manner.

As an electrophotographic photoreceptor having N containing a hydrazone compound represented by the general formula (1), it can be applied to any type of electrophotographic photoreceptor using a substance, but the preferred type is 1) A turtle that forms a charge transfer complex by combining an electron-donating substance and an electron-accepting substance.

2) An organic photoconductor sensitized by adding a dye.

3) Pigment dispersed in a hole matrix.

4) Functionally separated charge generation layer and charge transport layer.

5) A pattern whose pattern components are a eutectic complex consisting of a dye and a resin and an organic photoconductor.

6) A charge transfer complex in which an organic or inorganic charge generating material is added.

Among them, 3) to 6) are the most interesting types.

Furthermore, in the case of a 4) type photoreceptor, a hydrazone compound represented by the general formula (1) is used as a charge transport material for the charge transport layer of a photoreceptor that is functionally separated into two layers: a charge generation layer and a charge transport layer. When used, the sensitivity of the photoreceptor is particularly improved and the residual potential is low. Furthermore, in this case, the increase in the low-sensitivity residual force during repeated use can be suppressed to a practically negligible level. Therefore, the 4) type of photoreceptor will be described in detail.

As for the layer structure, a conductive layer, a charge generation layer, and a charge transport layer are essential.The charge generation layer may be either above or below the charge transport layer, but it is not suitable for electrophotographic photoreceptors of the type that are used repeatedly.・Mainly from the aspect of physically strong IW,
In some cases, conductive layers, charge generation layers,
It is preferable to stack the charge transport layers in this order. A layer on the conductor I and a layer '141. An adhesive layer can be provided as needed to improve the handling of raw materials and materials.

The 'lPL cargo transport layer V used in the present invention is expressed by the general formula (1
It is preferable to avoid formation by dissolving the hydrazone compound represented by For example, polysulfone, acrylic resin, methacrylic resin, vinyl chloride 4tl JIW, acid vinyl needle resin, phenolic resin, Epoquin resin, polyester resin, algide resin, polycarbonate, polyurethane, or repeats of these resins are used. 2 of the return units
Examples include copolymer resins containing at least one of the following: polyester resins and polycarbonates are particularly preferred. Also, po! ] Photoconductive polymers which themselves have charge transport capabilities, such as H-vinylcarbazole, can also be used as binders.

The blending ratio of the binder and the 'ME charge transporting compound is preferably 10 to 500 parts by weight of the charge transporting compound per 100 parts by weight of the binder. The thickness of this charge transport layer is 2~
100 microns, preferably 5-30 microns.

As for the coating method used when providing the charge transport layer, conventional methods such as blade coating method, Meyer bar coating method, spray coating method, dip coating method, bead coating method, air knife coating method can be used. .

Further, the solvent used in forming the charge transport layer of the present invention includes many useful organic solvents. Typical examples include aromatic hydrocarbons such as benzene, naphthalene, toluene, xylene, mesitylene, and chlorobenzene, ketones such as acetone and 2-butanone, and halogenated fats such as methylene chloride, chloroform, and ethylene chloride. Examples include group hydrocarbons, cyclic or linear ethers such as tetrahydrofuran and ethyl ether, and mixed solvents thereof.

The charge transport layer of the present invention may contain additives such as citron. Such additives include diphenyl, Ji
Diphenyl, 0-terphenyl, P-terphenyl, butyl phthalate, dimethyl glycol tucrate, dioctyl wotale-1, triphenyl phosphoric acid, methylnaphthalene, pendinoenone, chlorinated paraffin, dilaurylthiopropionate, 3 .5-dinitrosalicylic acid, various fluorocarbons, silicone oil, silicone rubber or dibutylhydroxytoluene, 2.2'
- Phenolic compounds such as methylenebi, <-(6-1-7'f-4-methylphenol), α-tocofecol, 2-1-octyl-5-chlorohydroquinone, 2,5-di-t-octylhydroquinone, etc. Examples include compounds.

As the charge generation material used for charge generation 1 and 4, any material can be used as long as it absorbs the charge and generates a charge carrier with extremely high efficiency, and is a preferred material. Examples include inorganic substances such as selenium, selenium/tellurium, selenium/arsenic, cadmium sulfide, amorphous silicon, pyrillam dyes, thiopyrylium dyes, triarylmethane dyes, thiazine dyes, cyanine dyes, phthalocyanine pigments, and perylene. Examples include M-type pigments, indigo pigments, thioindigo pigments, quinacridone pigments, Squaric It M materials, azo pigments, and polycyclic quinone pigments. The thickness of the charge generation layer is preferably 5 microns or less, preferably 0.05 to 3 microns.

Typical examples of charge-generating substances that can be used in the present invention are shown in Table F.

Charge generating substances (1) Amorphous Noricon (2) Selenium-Tellurium (3) Selenium-Arsenic (4) Cadmium Sulfide (5) ・1F! 41) 5] 1 (241 5; 3 2 (2 days 4 ct ct(33) r': [ (Jsu(38) C=0 0=C C=n 0=C 5゛n16 (a+1 C- 00S-C r 脣( 11 ”, !+15 0
．． ,u.

(5I) l
] C2H,, (chll5 5F) (Hata1 0 (- (Foundation) Methyl squaric acid dye sting (59) In silico dye (C, 1,, 1g, 78000
)-thioindigo stain f4 (C!, 1.116788
00 ) (61) β-type copper cap cyanine 63 These pigments are 1 type or 21fff1 or more 11th↓
Can be used together. Further, the pigment crystals (C) may be of the α type, β41 or other types, but the β type is particularly preferred.

In the present invention, when forming a charge generation layer using the above-mentioned compound, a layer of the above-mentioned compound can be formed by vacuum evaporation, sputtering, glow discharge, or the like.

4. Alternatively, a layer can be formed by dispersing the above-mentioned compound in a suitable binder and applying this dispersion using a suitable coating method. In addition, the layer of the above-mentioned compound can also be formed in a binder-free manner. When dispersing the above-mentioned compound, it can be dispersed by a known method using a ball mill, an attritor, etc., and the particle size is set to 5 microns or less, preferably 2 microns or less, and optimally 0.5 microns or less. It is desirable. In short, the aforementioned compounds can be combined with amines such as ethylenediamine, diethylenetriamine, tetraethylenepentamine, pentaethylenehexamine, diethylaminepropylamine, N-aminoethylpiperazine, benzyldimethylamine, α-methylbenzenyldimethylamine, and tridimethylaminomethylphenol. It can also be applied by dissolving it in a solvent. As a coating method, conventional methods such as a blade coating method, a Mayer-Bar coach ink method, a spray coating method, a dip coating method, a bead coating method, an air knife coating method, and a curtain coating method can be used.

The thickness of the charge generation layer used in the present invention is 5 microns or less,
Preferably, the thickness is between 0.01 micron and 1 micron.

Binders for dispersing the above-mentioned compounds include polyvinyl butyral, polymethyl methacrylate, polyester, polyvinylidene chloride, polyamide, chlorinated rubber,
polyvinyltoluene, polystyrene, polyvinyl chloride,
Ethyl cellulose, polyvinylpyridine, styrene-maleic anhydride copolymer, etc. can be obtained. The proportion of such a binder in the charge generation layer is preferably 80% by weight or less, preferably 50% by weight or less of the total weight of the charge generation layer.

In the electrophotographic photoreceptor of the present invention, the surface of the charge generation layer is polished to a mirror finish as necessary in order to uniformly inject carriers for heavy transport j·; can do.

As a mirror finishing method, for example, Japanese Patent Application Laid-Open No. 55-15535
The method disclosed in Publication No. 6 can be used.

The conductive layer may be any type of conductive layer conventionally used as long as it is imparted with conductivity.

As the material for the adhesive layer, various conventionally used binders such as casein, polyvinyl alcohol, nitrocellulose, hydroxymethyl cellulose, and polyamide can be used.

The thickness of the adhesive layer is preferably 01 to 5 microns, but suitably 05 to 3 microns.

The triazole compound used in the present invention has hole-transporting properties, and when using a photoreceptor with five layers in the order of a conductive layer, a charge generation layer, and a charge transport layer, it is necessary to charge the surface of the charge transport layer negatively. When charged and exposed to light, holes generated in the charge generation layer in the exposed area are injected into the charge transport layer, and then reach the surface and neutralize the negative charge, resulting in a decrease in surface potential and a gap between the exposed area and the unexposed area. A stark contrast occurs.

For visualization, there are various techniques that have been used in the past. Image methods can be used.

(4) With regard to photoreceptors other than the above-mentioned types, many patent publications and documents that have been proposed so far describe how to make them practical, so a detailed description will be omitted here, but these types of photoreceptors The hydrazone compound of the present invention is also effective for the body.

The electrophotographic photoreceptor of the present invention can be widely used not only in electrophotographic copying machines but also in electrophotographic applications such as laser printers, CRT printers, and electrophotographic plate making systems.

Next, examples of the present invention will be shown.

Example 1 Ammonia aqueous solution of casein (casein 1
．． 1.29.28% ammonia water 11, water 222 ml
) was coated with a Mayer bar and dried, coating f, t1. OS
An adhesive layer of '/771' was formed. Next, disazo pigment 51 having the following structure and butyral resin (butyralized 1f63 mol 96) 27 were dispersed together with a solution dissolved in 95 ml of ethanol, and then coated on the adhesive layer and after drying, the coating stitch was 0.2 f/ m'(', Y~ A charge generation layer was formed.

Next, the hydrazone compound 51 of Δ62, Bo IJ-4
, 4'-dioxydiphenyl-2,2-glopane carbonate (viscosity average molecular weight 30,000) 5vf dissolved in 1.5011 Il of dichloromethane was coated on the charge generation layer and dried to give a charge with a slope failure of 109/lri. A transport layer was formed.

The electrophotographic photoreceptor thus prepared was statically charged with corona at θ5' KV using Kawaguchi Ii Machine's Modee SP-428 Shizuichi Copying Paper Tester, and then charged at 1 in the dark.
After holding for 0 seconds, it was exposed to light at an illuminance of 5 lux to examine charging characteristics.

The initial potential vO (V), the potential retention rate for 10 seconds in the dark is Rv (%), and the half-decay exposure amount is E%I7? ux-sec)
The charging characteristics of this photoreceptor are shown below.

VoUni 80V 9 Rv: 87π E%: 4.7/ux@sec Example 2 The following pigments were vacuum deposited on an aluminum plate with a thickness of 100 μm (a charge generation layer with a thickness of −0.15 μm was formed).

Next, polyester resin (Byron 200, Toyobo (m)
> 5t and the exemplified hydrazone compound 57 of /I62 above dissolved in 1.50 ml of dichloromethane were applied and dried on the surface of the ``heavy generated'' Δ.
/ Silence' Kamikago J8 layer was completely formed.

The charging characteristics of the electrophotographic photoreceptor thus prepared were examined in the same manner as in Example 1, and the results are shown below.

Vo: -470V ■MomoV: 859 to 0 E! A: 5.77? ux-sec Examples 3 to 48 Electrophotographic photoreceptors were prepared 1 in exactly the same manner except that the hydrazone compounds shown in Table 1 were used in place of the 42 hydrazone compounds used in Example 1. -It is.

The charging characteristics of each photoreceptor were measured in the same manner as in Example 1. These results are shown in Table 1.

Example 49 Selenium/tellurium (tellurium 10) was vacuum deposited on an aluminum plate to form a charge generation layer with a thickness of 0.8 μm.

Next, the same charge transport layer as used in Example 1 was coated and dried, and η: working area was set to llf/ff/.

The charging characteristics of the electrophotographic photosensitive plate thus prepared were examined in the same manner as in Example 1, and the results are shown below.

7;1 Vo: -560V Rv: 89% EIA: 2.7 Jux・sec Example 50 Revision used in Example 1: AI hydrazone compound 5
F and 5 g of poly-N-vinyl horn leverso # (molecular weight 300,000) were dissolved in chloromethane 150-1. β-type copper phthalocyanine 107 was added to the solution, and after dispersion, the casein layer used in Example 1 was provided. Coat 1-2 on the casein layer L of the aluminum plate. / +rl toshida.

The photoreceptor thus prepared was tested in the same manner as in Example 1, and the results are shown below.

However, when the charge 1 polarity is set to ■, 0 vO: +51 Ov T (, v: 87% E!A: 6.6 /uxIIsec Example 51 0.21 thickness molybdenum plate (substrate) with a cleaned surface
was fixed at a predetermined position in a glow discharge deposition tank. Evacuate the inside of the θCK tank and remove approximately 5 x 1O-6t, o
The vacuum level was set to rr. Thereafter, the input voltage of the heater was increased to stabilize the molybdenum substrate temperature at 150°C.

Thereafter, hydrogen gas and silane gas (15% by volume relative to hydrogen gas) were introduced into the tank, and the gas flow rate and the main valve of the deposition tank were adjusted (stabilized at 1.5 Lorr).

Next, 5MHz high frequency power was applied to the induction coil to generate glow Ik electricity inside the coil in the tank, resulting in 30W of human power and 11 energy. An amorphous silicon layer was grown on the substrate-L under the conditions described in E, and the same conditions were maintained until the film thickness reached 2 .mu.m.The stage glow firing was then discontinued.

After that, turn off the heating heater and high frequency machihara, wait until the temperature of the substrate reaches 100℃, close the hydrogen gas and silane gas outflow valves, and temporarily heat the inside of the tank to 10-5 torr.
After reducing the pressure to below r (/c), the pressure was returned to atmospheric pressure and the substrate was taken out.

This amorphous silicon layer was then formed.

The photoreceptor thus obtained was placed in a 'Fi'I electric exposure equipment, corona charged with e6 KV, and immediately exposed to a light image.

The optical image is created using a tungsten lamp light source.5 It was irradiated with a transmission type destchard) K+.

Thereafter, a well-spread toner image was obtained on the surface of the photoreceptor by applying (94+J') commercial toner (including toner and carrier) to the surface of the photoreceptor at a distance of 2 degrees without cassgate.

Patent applicant: Cannon Floor Company copying company 'n(j

Claims (1)

[Scope of Claims] An electrophotographic photoreceptor comprising a layer containing at least one compound represented by the following general formula (1). l (wherein A represents a substituted or unsubstituted heterocyclic group.
indicates the atoms necessary to complete a substituted or unsubstituted heterocycle. Ya and Toshi represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group. n is 0
゜Indicates 1 or 2. m represents 0 or 1. )