JP3295284B2 - Electrophotographic photoreceptor, process cartridge having the electrophotographic photoreceptor, and electrophotographic apparatus - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photosensitive member and a process cartridge having the electrophotographic photosensitive member.

[0002]

2. Description of the Related Art Conventionally, inorganic photoconductive materials such as selenium, cadmium sulfide, and zinc oxide have been widely used as electrophotographic photoreceptors. On the other hand, as an electrophotographic photoreceptor using an organic photoconductive substance, a photoconductive polymer represented by poly-N-vinylcarbazole or 2,5-bis (p-diethylaminophenyl) -1,3,4 -Oxadiazo-
There are known ones using a low-molecular organic photoconductive substance such as benzene and a combination of such an organic photoconductive substance with various dyes and pigments. An electrophotographic photosensitive member using an organic photoconductive substance has good film-forming properties and can be produced by coating. Therefore, it has an advantage that an extremely high productivity and inexpensive electrophotographic photosensitive member can be provided. In addition, there is an advantage that color sensitivity can be freely controlled by selecting a dye or a pigment to be used, and wide studies have been made so far. Particularly recently, with the development of a function-separated type photoconductor in which a charge generation layer containing an organic photoconductive dye or pigment and a charge transport layer containing a photoconductive polymer or a low-molecular organic photoconductive substance are laminated, Significant improvements have been made in sensitivity and durability, which have been disadvantages of conventional organic electrophotographic photosensitive members.

Azo pigments have excellent photoconductivity, and since compounds having various characteristics can be easily obtained by combining the azo component and the coupler component, a large number of compounds have been proposed. For example, see JP-A-54-22
834, JP-A-58-177555, JP-A-58-194035, JP-A-61-21555.
No. 6, JP-A-61-241763,
No. 3-17456, and the like. However,
Conventional electrophotographic photoreceptors using azo pigments are not necessarily sufficient in terms of sensitivity and potential stability during repeated use, and only very few materials have been put to practical use.

[0004]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel electrophotographic photoreceptor, which has a practical high sensitivity characteristic and a stable potential characteristic when repeatedly used. An object of the present invention is to provide a small electrophotographic photosensitive member, and to provide a process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member.

[0005]

According to the present invention, there is provided an electrophotographic photosensitive member having a photosensitive layer on a conductive support, wherein the photosensitive layer has an azide calix [n] represented by the following general formula (1).
The electrophotographic photosensitive member is characterized by containing an arene compound. General formula (1)

Embedded image Wherein, n represents an integer of _4~8, R 1, R ₂ and R ₃ represents a hydrogen atom or an alkyl group, Ar is have a have good aromatic hydrocarbon ring or a substituent a substituent Represents an aromatic heterocyclic ring which may be substituted.

Examples of the alkyl group in the above expression include methyl, ethyl, propyl and the like, and examples of the aromatic hydrocarbon ring which may have a substituent or the aromatic hetero ring which may have a substituent include Hydrocarbon-based aromatic rings such as benzene, naphthalene, fluorene, phenanthrene, anthracene, fluoranthene and pyrene, furan, thiophene, pyridine, indole, benzothiazole, carbazole, benzocarbazole, acridone, dibenzothiophene,
Benzoxazole, benzotriazole, oxathiazole, thiazole, phenazine, cinnoline, heteroaromatic ring such as benzocinnoline, further bonded directly with the aromatic ring or an aromatic group or a non-aromatic group,
For example, triphenylamine, diphenylamine, N-methyldiphenylamine, biphenyl, terphenyl, binaphthyl, fluorene, phenanthrenequinone, anthraquinone, benzanthrone, diphenyloxazole, phenylbenzoxazole, diphenylmethane,
Examples include diphenyl sulfone, diphenyl ether, benzophenone, stilbene, distyrylbenzene, tetraphenyl-p-phenylenediamine, tetraphenylbenzidine and the like.

Examples of the substituent which the aromatic hydrocarbon ring or aromatic hetero ring may have include alkyl groups such as methyl, ethyl, propyl and butyl, alkoxy groups such as methoxy and ethoxy, dimethylamino, diethylamino and the like. A dialkylamino group, a fluorine atom, a chlorine atom, a halogen atom such as a bromine atom, a hydroxy group, a nitro group, a cyano group,
And a halomethyl group.

Next, examples of azoxy calix [n] arene compounds used in the present invention are shown in Tables 1 to 5, but the present invention is not limited to these.

[0009]

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

The azylated calix [n] arene compound represented by the general formula (1) is obtained by subjecting an amine to tetrazotization by a conventional method and coupling with the calix [n] arene in the presence of an alkali in an aqueous system, After converting the tetrazonium salt into a borofluoride salt or a double zinc chloride salt, sodium acetate, triethylamine, and the like in an organic solvent such as tetrahydrofuran, N, N-dimethylformamide, and dimethylsulfoxide.
It can be easily synthesized by coupling with calix [n] arene in the presence of a base such as pyridine and N-methylmorpholine.

Synthesis Example (Synthesis of Exemplified Compound 1) 75 ml of water was added to a 300 ml beaker.
15 ml of concentrated hydrochloric acid and 11.8 of p-cyanoaniline
g (0.1 mol), cooled to 0 ° C., and a solution prepared by dissolving 7.6 g (0.11 mol) of soda nitrite in 17 g was maintained at a temperature of 5 ° C. or lower. It was dropped in 10 minutes. After stirring for 20 minutes, the mixture was filtered with carbon, and a solution prepared by dissolving 19.8 g (0.18 mol) of sodium borofluoride in 60 ml of water was added dropwise to this solution with stirring, and the precipitated borofluoride was removed. After being collected by filtration, washed with cold water, washed with cold acetonitrile-isopropyl ether, and dried at room temperature under reduced pressure. Yield 18.4 g, 85.0%.

Next, 10 ml of tetrahydrofuran and 2.14 g (0.005 mol) of calix [4] arene were placed in a 300 ml beaker, cooled to 0 ° C., and obtained into this solution. Borofluoride 4.45
g (0.021 mol) was added followed by the slow addition of 50 ml of the example pyridine. After stirring for 2 hours while maintaining the liquid temperature at 5 ° C. or lower, the mixture was poured into 1 liter of cold water, the precipitate was collected by filtration, washed with chloroform and acetone, and dried under reduced pressure at room temperature. Yield 3.53 g, yield 75.05.

[0013]

The electrophotographic photosensitive member of the present invention has a photosensitive layer containing an azoxy calix [n] arene compound represented by the general formula (1) on a conductive support. The form of the photosensitive layer may be any of known forms, but the general formula (1)
A function-separated type photosensitive layer in which a layer containing an azoxy calix [n] arene compound represented by the following formula is used as a charge generation layer and a charge transport layer is laminated thereon is particularly preferable.

The charge generation layer is formed by applying a coating solution obtained by dispersing the above-mentioned azoxy calix [n] arene compound together with a binder resin in a suitable solvent onto a conductive support by a known method. It is possible to form a thin film layer having a thickness of 5 μm or less, preferably 0.1 to 1 μm.

The binder resin is selected from a wide range of insulating resins or organic photoconductive polymers, and may be substituted or unsubstituted polyvinyl butyral or polyvinyl benza.
, Polyarylate, polycarbonate, polyester, phenoxy resin, cellulose resin, acrylic resin,
Polyurethane and the like are preferable, and examples of the substituent include a halogen atom such as a fluorine atom and a chlorine atom, an alkyl group, an alkoxy group, a nitro group, a trifluoromethyl group, and a cyano group. The amount of the binder resin used is 80% by weight or less, preferably 40% by weight or less in terms of the content in the charge generation layer.

The solvent used is preferably selected from those which dissolve the resin and do not dissolve the charge transport layer and the undercoat layer described below. Specifically, ethers such as tetrahydrofuran and 1,4-dioxane, ketones such as cyclohexanone and methyl ethyl ketone, amides such as N, N-dimethylformamide, esters such as methyl acetate and ethyl acetate, toluene, Aromatic hydrocarbon compounds such as xylene and chlorobenzene, methanol, ethanol
And alcohols such as 2-propanol, and aliphatic hydrocarbon compounds such as chloroform and methylene chloride.

The charge transport layer is stacked on or below the charge generation layer, and has a function of receiving charge carriers from the charge generation layer in the presence of an electric field and transporting the carriers. The charge transporting layer is formed by applying a coating solution in which a charge transporting substance is dissolved in a solvent together with a suitable binder resin as required, and the film thickness is generally 5 to 40 μm, preferably 10 to 40 μm. 25 μm is desirable.

The charge transporting substance includes an electron transporting substance and a hole transporting substance. Examples of the electron transporting substance include 2,4,7-trinitrofluorenone, 2,4,5,7-tetranitrofluorenone, chloranil, and tetracyano. Examples thereof include electron-withdrawing substances such as quinodimethane, and those obtained by polymerizing these electron-withdrawing substances. Examples of the hole-transporting substance include polycyclic aromatic compounds such as pyrene and anthracene, carbazole, and India. -Hydrogen, imidazole, oxazole, thiazol, oxadiazol, pyrazol, pyrazoline, thiadiazole, triazole-based and other heterocyclic compounds, p-diethylaminobenzaldehyde-N, N-diphenyl Hydrazone, hydrazone-based compounds such as N, N-diphenylhydrazino-3-methylidene-9-ethylcarbazole, α-phenyl- Styryl compounds such as' -N, N-diphenylaminostilbene, 5- [4- (di-P-tolylamino) benzylidene] -5H-dibenzo [a, d] cycloheptene, benzidine compounds, triarylmethane compounds; Examples include triphenylamine or polymers having a group consisting of these compounds in the main chain or side chain (for example, poly-N-vinylcarbazole, polyvinylanthracene, 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. These charge transport materials can be used alone or in combination of two or more.

When the charge transporting material does not have a film-forming property, an appropriate binder can be used, and specific examples thereof include acrylic resin, polyarylate, polyester, and polycarbonate.
Insulating resins such as carbonate, polystyrene, acrylonitrile-styrene copolymer, polyacrylamide, polyamide, and chlorinated rubber; and organic photoconductive polymers such as poly-N-vinylcarbazole and polyvinylanthracene.

As the conductive support on which the photosensitive layer is formed, for example, aluminum, aluminum alloy, copper, zinc, stainless steel, vanadium, molybdenum, chromium, titanium, nickel, indium, gold and platinum are used. Further, plastics (eg, polyethylene, polypropylene, polyvinyl chloride, polyethylene terephthalate, acrylic resin, etc.) and conductive particles (eg, carbon black, silver particles, etc.) formed by coating these metals or alloys by vacuum evaporation. ) Together with a suitable binder resin on a plastic or metal substrate, or a support in which conductive particles are impregnated in plastic or paper.

An undercoat layer having a barrier function and an adhesive function may be provided between the conductive support and the photosensitive layer. The thickness of the undercoat layer is 5 μm or less, preferably 0.1 to 3 μm.
Is appropriate. The undercoat layer can be formed of casein, polyvinyl alcohol, nitrocellulose, polyamide (nylon 6, nylon 66, nylon 610, copolymer nylon, alkoxymethylated nylon, etc.), polyurethane, aluminum oxide, or the like.

As another specific example of the present invention, general formula (1)
And an electrophotographic photoreceptor in which a charge-transporting substance and an azide calix [n] arene compound represented by the following formula are contained in the same layer. The electrophotographic photoreceptor of this example can be prepared by applying a solution obtained by dispersing the azoxy calix [n] arene compound and a charge transporting substance in an appropriate resin solution on a conductive support and drying. it can.

In any of the electrophotographic photoreceptors, the crystal form of the azoxy calix [n] arene compound represented by the general formula (1) may be amorphous or crystalline. And, if necessary, the azoxy calix [n]
Two or more arene compounds may be used in combination, or may be used in combination with a known charge generating substance such as a phthalocyanine-based pigment, a disazo-based pigment, or a perylene-based pigment.

The electrophotographic photosensitive member of the present invention can be used not only for an electrophotographic copying machine but also for a laser beam printer, a C
RT printer, LED printer, LCD printer,
It can be widely used in electrophotographic applications such as laser plate making and facsimile.

According to the present invention, the electrophotographic photosensitive member of the present invention, and at least one means selected from the group consisting of a charging means, a developing means and a cleaning means are integrally supported and attached to and detached from an electrophotographic apparatus main body. It is composed of a process cartridge characterized by being flexible.

Further, the present invention comprises an electrophotographic apparatus comprising the electrophotographic photoreceptor of the present invention, a charging unit, an image exposing unit, a developing unit and a transferring unit.

FIG. 1 shows a schematic configuration of an electrophotographic apparatus having a process cartridge having the electrophotographic photosensitive member of the present invention. In FIG. 1, reference numeral 1 denotes a drum-shaped electrophotographic photosensitive member of the present invention, which is driven to rotate around an axis 2 at a predetermined peripheral speed in a direction indicated by an arrow. In the rotation process, the photosensitive member 1 is uniformly charged at a predetermined positive or negative potential on the peripheral surface thereof by the primary charging means 3, and then the image exposure means (such as a slit exposure or a laser beam scanning exposure) is used. (See FIG. 1). Thus, an electrostatic latent image is sequentially formed on the peripheral surface of the photoconductor 1.

The formed electrostatic latent image is then transferred to developing means 5
Is transferred to the transfer material 6 from the paper supply unit (not shown) and fed between the photosensitive member 1 and the transfer means 6 in synchronization with the rotation of the photosensitive member 1. Are sequentially transferred by the transfer means 6. The transfer material 7 having undergone the image transfer is separated from the photoreceptor surface, introduced into the image fixing means 8 and subjected to image fixing, thereby being printed out as a copy (copy) outside the apparatus. The surface of the photoreceptor 1 after the image transfer is cleaned and cleaned by removing the transfer residual toner by the cleaning means 9, and further subjected to a static elimination process by the pre-exposure light 10 from the pre-exposure means (not shown). After that, it is repeatedly used for image formation. When the primary charging means 3 is a contact charging means using a charging roller or the like, pre-exposure is not necessarily required.

In the present invention, a plurality of components such as the photoreceptor 1, the primary charging means 3, the developing means 5 and the cleaning means 9 are integrally connected as a process cartridge. Alternatively, the process cartridge may be configured to be detachable from a main body of an electrophotographic apparatus such as a copying machine or a laser beam printer. For example, at least one of the primary charging means 3, the developing means 5 and the cleaning means 9 is integrally supported together with the photoreceptor 1 to form a cartridge, and the apparatus main body is guided by a guide means such as the rail 12 of the apparatus main body. The process cartridge 11 can be detachably mounted on the cartridge. When the electrophotographic apparatus is a copier or a printer, the image exposure light 4 uses reflected light or transmitted light from the original, or reads the original with a sensor and converts it into a signal. This is light emitted by scanning of the laser beam, driving of the LED array, driving of the liquid crystal shutter array, and the like.

On the other hand, when used as a facsimile printer, the image exposure light 4 becomes exposure light for printing received data. FIG. 2 is a block diagram showing an example of this case. The controller 14 controls the image reading unit 13 and the printer 22. The entire controller 14 is controlled by the CPU 20. The read data from the image reading unit 13 is transmitted to the partner station through the transmission circuit 16. Data received from the partner station is sent to the printer 22 through the receiving circuit 15. Predetermined image data is stored in the image memory. The printer controller 21 controls the printer 22. 17
Is a telephone. The image received from the line 18 (image information from a remote terminal connected via the line) is demodulated by the receiving circuit 15 and then decoded by the CPU 20 and sequentially stored in the image memory 19. Is done. When the image of at least one page is stored in the image memory 19, the image of the page is recorded. The CPU 20 reads out the image information of one page from the image memory 19 and sends out the decoded image information of one page to the printer-controller-21. When receiving the image information of one page from the CPU 20, the printer controller 21 controls the printer 22 to record the image information of the page. CPU 20
Is receiving the next page during recording by the printer-22. Thus, reception and recording of an image are performed.

[0032]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The electrophotographic photosensitive member of the present invention is manufactured, for example, as follows.

A solution obtained by dissolving methoxymethylated nylon and alcohol-soluble nylon in methanol on an aluminum support is applied with a Myrbar to form an undercoat layer. Next, Exemplified Compound 1 is added to cyclohexanone. A butyral resin was dissolved in the solution, and the mixture was dispersed with a sand mill to prepare a coating for the charge generation layer. The coating was applied to the undercoat layer with a myrbar to form a charge generation layer. A compound for a charge transport layer is prepared by dissolving a polymethylmethacrylate resin and a polymethyl methacrylate resin in chlorobenzene,
Coating with a bar to form a charge transport layer, thereby producing an intended electrophotographic photosensitive member.

Further, the electrophotographic photosensitive member may be provided with a process cartridge integrally supporting a primary charging means, a developing means and a cleaning means as shown in FIG. 1, for example.

As shown in FIG. 2, for example, a printer can be used as a printer in a facsimile as an electrophotographic apparatus provided with the electrophotographic photosensitive member of the present invention.

[0036]

【Example】

Examples 1 to 8 A solution prepared by dissolving 5 g of methoxymethylated nylon (average molecular weight: 32,000) and 10 g of alcohol-soluble copolymerized nylon (average molecular weight: 29000) in 95 g of methanol was applied to an aluminum substrate with a Myer bar. , Dried film thickness 1μ
m was formed.

Next, 6 g of Exemplified Compound 1 was added to a solution prepared by dissolving 2 g of butyral resin (butyralization degree: 63 mol%) in 95 g of cyclohexanone, and dispersed in a sand mill for 20 hours. This dispersion was applied to the undercoat layer with a Myr bar so that the film thickness after drying was 0.2 μm to form a charge generation layer.

Next, 5 g of a hydrazone compound having the following structural formula

Embedded image And polymethyl methacrylate (number average molecular weight 10,000
0) 5 g was dissolved in 40 g of chlorobenzene, and this solution was applied on the charge generation layer with a Myr bar so that the film thickness after drying was 16 μm to form a charge transport layer. A photoreceptor was prepared. This is referred to as Photoconductor 1.

Electrophotographic photoreceptors corresponding to Examples 2 to 8 were prepared in exactly the same manner as in Example 1 except that another exemplary compound was used instead of exemplary compound 1. Photoconductors 1 to 8 are used.

Each of the photoconductors 1 to 8 was replaced by Kawaguchi Electric Co., Ltd.
-5K using an electrostatic copying paper tester (SP-428)
After being negatively charged by V corona discharge and left in a dark place for 1 second,
Exposure was performed with light having an illuminance of 10 lux using a halogen lamp, and charging characteristics were evaluated. Charging characteristics include surface potential V
_{At 0} , the exposure amount E _1/2 required for the surface potential after being left in a dark place to attenuate to _{１ ／} was measured. Table 6 shows the results.

[0041]

[Table 6]

Comparative Examples 1 and 2 Comparative Example 1 was repeated in exactly the same manner as in Example 1 except that Comparative Pigment 1 and Comparative Pigment 2 having the following structural formulas were used instead of Exemplified Compound 1 used in Example 1. And 2 were prepared. The photoconductor 9 and the photoconductor 10 are used. The charging characteristics of each photoconductor were evaluated in the same manner as in Example 1. Table 7 shows the results.

Comparative pigment 1

Embedded image Comparative pigment 2

Embedded image

[0044]

[Table 7]

From these results, it is known that all the electrophotographic photosensitive members of the present invention have a sufficient charging ability and excellent sensitivity.

Examples 9 to 13 The photosensitive member 1 was replaced with a corona charger of -7.0 KV, an exposure optical system,
It was affixed to a cylinder of an electrophotographic copying machine equipped with a developing unit, a transfer charger, a charge erasing exposure optical system and a cleaner.

The initial dark potential V _D and light portion potential V _L, respectively -700 V, and set near -200 V, 5 thousand times repeated variation of the dark portion potential when using △ V _D and the amount of fluctuation of the light portion potential ΔV _L was measured. Note that a negative sign in the fluctuation amount of the potential indicates a decrease in the absolute value of the potential, and a positive sign indicates an increase in the absolute value of the potential. Table 8 shows the results.

The same evaluation was performed for the photoconductors 4, 6, 7, and 8. Table 8 shows the results.

[0049]

[Table 8]

Comparative Examples 3 and 4 With respect to the photoconductors 9 and 10, the amount of potential fluctuation during repeated use was measured in the same manner as in Example 9. Table 9 shows the results.

[Table 9]

From the results of Examples 9 to 13 and Comparative Examples 3 and 4, it is known that the electrophotographic photoreceptor of the present invention has little change in potential when repeatedly used.

Example 14 A polyvinyl alcohol having a thickness of 0.5 μm was formed on an aluminum surface of an aluminum-deposited polyethylene terephthalate film.
An undercoat layer was formed. On this, the same dispersion of Exemplified Compound 22 as in Example 8 was applied with a Myer bar and dried to form a 0.2 μm-thick charge generation layer.

Then, 5 g of a styryl compound having the following structural formula

Embedded image And 5 g of polycarbonate (weight average molecular weight: 55000)
Was dissolved in 40 g of tetrahydrofuran and applied onto the charge generation layer and dried to form a charge transport layer having a thickness of 16 μm, thereby producing an electrophotographic photoreceptor.

The charging characteristics and durability characteristics of the produced electrophotographic photosensitive member were measured by the same methods as in Examples 1 and 9. The results are shown. V ₀ : -650 V, E _1/2 : 1.35 lux · sec ΔV _D : 0 V, ΔV _L : +5 V

Example 15 A polyvinyl alcohol having a thickness of 0.5 μm was formed on an aluminum surface of an aluminum-deposited polyethylene terephthalate film.
An undercoat layer was formed. On this, the same dispersion of Exemplified Compound 22 as in Example 8 was applied with a Myer bar and dried to form a 0.2 μm-thick charge generation layer.

Then, 5 g of a triphenylamine compound having the following structural formula

Embedded image And 5 g of polycarbonate (weight average molecular weight: 55000)
Was dissolved in 40 g of tetrahydrofuran and applied onto the charge generation layer and dried to form a charge transport layer having a thickness of 17 μm, thereby producing an electrophotographic photoreceptor.

The charging characteristics and durability characteristics of the produced electrophotographic photosensitive member were measured by the same methods as in Examples 1 and 9. The results are shown. V ₀ : -680 V, E _1/2 : 1.30 lux · sec ΔV _D : 0 V, ΔV _L : +5 V

Example 16 An electrophotographic photosensitive member was prepared in the same manner as in Example 8, except that the charge generation layer and the charge transport layer in the electrophotographic photosensitive member prepared in Example 8 were applied in reverse order. The charging characteristics were evaluated in the same manner as in Example 1. However, the charging was positive. The results are shown. V ₀ : +610 V, E _1/2 : 1.68 lux / sec

Example 17 A charge generation layer was formed in the same manner as in Example 7,
2,4,7-trinitro-9-fluorenone 5
g and 5 g of poly-4,4'-dioxydiphenyl-2,2-propane carbonate (molecular weight: 300,000) dissolved in 50 g of tetrahydrofuran were dried with a Myer bar and dried to form a film having a thickness of 16 μm. A charge transport layer was formed to prepare an electrophotographic photoreceptor, and the charging characteristics were evaluated in the same manner as in Example 1. However, the charging was positive. The results are shown. V ₀ : +610 V, E _1/2 : 2.25 lux / sec

Example 18 0.5 g of Exemplified Compound 21 was added to 9.5 g of cyclohexanone.
And a paint shaker for 5 hours. A solution prepared by dissolving 5 g of the same charge transporting substance as used in Example 1 and 5 g of polycarbonate in 40 g of tetrahydrofuran was added thereto.
Shake for another hour. The prepared coating solution was applied to an aluminum substrate with a Myer bar and dried to form a photosensitive layer having a thickness of 20 μm to prepare an electrophotographic photosensitive member. The charging characteristics were evaluated in the same manner as in Example 1. However, the charging was positive. The results are shown. V ₀ : +700 V, E _1/2 : 3.15 lux / sec

Example 19 A solution prepared by dissolving 5 g of methoxymethylated nylon (average molecular weight: 32,000) and 10 g of alcohol-soluble copolymerized nylon (average molecular weight: 29000) in 95 g of methanol was applied to an aluminum substrate with a Myer bar. And dry film thickness 1μ
m was formed.

Next, 5 g of disazo pigment having the following structural formula

Embedded image Is added to 95 g of cyclohexanone with a butyral resin (butyral
(A degree of hydrolysis of 63 mol%) was added to the dissolved solution, and the mixture was dispersed in a sand mill for 20 hours. This dispersion was applied to the undercoat layer with a Myr bar so that the film thickness after drying was 0.2 μm to form a charge generation layer.

Next, 4.5 g of the styryl compound used in Example 15, 0.5 g of Exemplified Compound 5 and 5 g of polymethyl methacrylate (number average molecular weight: 100,000) were dissolved in 40 g of chlorobenzene, and this liquid was charged. On the layer, a charge transport layer was formed by coating with a Myer bar so that the film thickness after drying became 20 μm, and an electrophotographic photosensitive member was prepared.

Example 20 An electrophotographic photosensitive member was prepared in exactly the same manner as in Example 19, except that Exemplified Compound 6 was used instead of Exemplified Compound 5.

The electrophotographic photosensitive members prepared in Examples 19 and 20 were irradiated with light of 1500 lux for 5 minutes using a white fluorescent lamp, and the difference between the dark area potential after 5 minutes of irradiation and the dark area potential before irradiation was obtained. (△ V _pM ) was measured to evaluate the photo memory.

Comparative Example 5 An electrophotographic photosensitive member was prepared in the same manner as in Example 19, except that Exemplified Compound 5 was not used, and was evaluated in the same manner.

[0067]

[Table 10]

[0068]

According to the electrophotographic photoreceptor of the present invention, when the photosensitive layer contains a specific azoxy calix [n] arene compound, either the generation efficiency or the injection efficiency of charge carriers inside the photosensitive layer is improved. One or both are improved, and a remarkable effect is obtained in that characteristics excellent in sensitivity and potential stability during repeated use are obtained. Also, it can be mounted on a process cartridge and an electrophotographic apparatus to achieve the same excellent effects.

[Brief description of the drawings]

FIG. 1 is a process car having an electrophotographic photoreceptor of the present invention.
FIG. 2 is a diagram illustrating a schematic configuration of an electrophotographic apparatus having a cartridge.

FIG. 2 is a diagram showing an example of a facsimile block having the electrophotographic photosensitive member of the present invention.

[Explanation of symbols]

 REFERENCE SIGNS LIST 1 electrophotographic photoreceptor of the present invention 2 axis 3 primary charging means 4 image exposure light 5 developing means 6 transfer means 7 transfer material 8 image fixing means 9 cleaning means 10 pre-exposure light 11 process cartridge 12 rail 13 Image reading unit 14 Controller 15 Receiving circuit 16 Transmitting circuit 17 Telephone 18 Line 19 Image memory 20 CPU 21 Printer controller 22 Printer

Claims (4)

(57) [Claims] 1. An electrophotographic photosensitive member having a photosensitive layer on a conductive support, characterized in that the photosensitive layer contains an azoxy calix [n] arene compound represented by the following general formula (1). Electrophotographic photoreceptor. General formula (1) Wherein, n represents an integer of _4~8, R 1, R ₂ and R ₃ represents a hydrogen atom or an alkyl group, Ar is have a have good aromatic hydrocarbon ring or a substituent a substituent Represents an aromatic heterocyclic ring which may be substituted. 2. The photosensitive layer comprises at least two layers: a charge generation layer containing the azoxy calix [n] arene compound represented by the general formula (1) and a charge transport layer. Electrophotographic photoreceptor. 3. The electrophotographic photosensitive member according to claim 1, and at least one unit selected from the group consisting of a charging unit, a developing unit and a cleaning unit are integrally supported, and are detachable from the main body of the electrophotographic apparatus. A process cartridge. 4. An electrophotographic apparatus comprising the electrophotographic photosensitive member according to claim 1, a charging unit, an image exposing unit, a developing unit, and a transferring unit.