JPH10186705A - Electrophotographic photoreceptor, process cartridge, and electrophotographic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an electrophotographic photoreceptor which maintains film strength while enhancing lubricity, preservation stability, and cleaning characteristic, can provide an image that remains good for a long period because of a good solvent cracking property, and is easy to manufacture by making the surface layer of the electrophotographic photoreceptor contain a polymer having a specific component unit. SOLUTION: A surface layer of an electrophotographic photoreceptor contains a polymer having a component unit represented by the formula. In the formula, R1 to R8 represent hydrogen atom, halogen atom, or alkyl group; X represents an alkylene group that may have a substituent, a cycloalkylene group, alkinylene group or arylene group. The polymer containing the component unit represented by the formula is usable with its molecular weight in the range of 2,000 to 400,000. The surface layer contains the polymer having the component unit represented by the formula and an aromatic-group-containing resin. Alternatively, the surface layer contains the polymer having the component unit represented by the formula and a fluorine-atom-containing compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an electrophotographic copying machine,
Electrophotographic photoreceptors that can be widely used in electrophotographic applications such as laser beam printers and plain paper faxes,
And a process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member.

[0002]

2. Description of the Related Art Electrophotography is disclosed in U.S. Pat. No. 2,297,691.
As shown in the specification, a photoconductive material is used which comprises a support coated with an insulating substance in which the electric resistance changes depending on the amount of irradiation received during image exposure and which is in a dark place. The basic characteristics required of an electrophotographic photoreceptor using this photoconductive material are (1) that it can be charged to an appropriate potential in a dark place, (2) that there is little charge dissipation in a dark place, and ( 3) The charge can be quickly dissipated by light irradiation.

[0003] Conventionally, selenium,
Inorganic photoreceptors having a photosensitive layer mainly containing an inorganic photoconductive compound such as zinc oxide and cadmium sulfide have been widely used. However, they satisfy the conditions (1) to (3), but do not always satisfy thermal stability, moisture resistance, durability, productivity, and the like. For example, when selenium is crystallized, its characteristics as a photoreceptor deteriorate, making it difficult to manufacture. In addition, heat, fingerprints, and the like cause crystallization, which causes crystallization to deteriorate the performance as a photoreceptor. Cadmium sulfide has problems in moisture resistance and durability, and zinc oxide has problems in smoothness, hardness and friction resistance. Further, the photosensitive wavelength region of many inorganic photosensitive members is limited. For example, the photosensitive wavelength region of selenium is a blue region and has little sensitivity in a red region.

For this reason, various methods have been proposed to extend the photosensitivity to the long wavelength region, but there are many restrictions on the selection of the photosensitive wavelength region. Even when zinc oxide or cadmium sulfide is used as the photoreceptor, the photosensitive wavelength range of the photoreceptor itself is narrow, and it is necessary to add various sensitizers.

In order to overcome the disadvantages of these inorganic photoconductors, electrophotographic photoconductors containing various organic photoconductive compounds as main components have been actively developed in recent years. For example, US Pat. No. 3,838,851 discloses a photoreceptor having a charge transfer layer containing triallylpyrazoline, US Pat.
Japanese Patent No. 871882 discloses a photoreceptor including a charge generation layer composed of a derivative of a perylene pigment and a charge transfer layer composed of a condensate of 3-propylene and formaldehyde.

A photoreceptor using a bisazo pigment or a trisazo pigment as a charge generating substance is disclosed in
JP-A-33445, JP-A-56-46237 and JP-A-60-111249 are already known.

Further, the photosensitive wavelength range of the electrophotographic photosensitive member can be freely selected depending on the organic photoconductive compound. For example, with respect to azo organic pigments, JP-A-61-272754 and JP-A-56-272754
JP-A-167759 discloses substances exhibiting high sensitivity in the visible region, and JP-A-57-195767 and JP-A-61-228453 disclose substances having sensitivity up to the infrared region. Have been.

Among these materials, materials having sensitivity in the infrared region are used in laser beam printers (hereinafter abbreviated as LBPs), LED printers, and the like, which have been making remarkable progress in recent years, and the demand frequency is increasing.

Electrophotographic photoreceptors using these organic photoconductive compounds are used as function-separated type photoreceptors in which a charge generation layer and a charge transport layer are laminated in order to satisfy both electrical and mechanical properties. Often. On the other hand, as a matter of course, the electrophotographic photoreceptor is required to have sensitivity, electric characteristics, and optical characteristics according to the electrophotographic process applied.

Particularly, in the case of an electrophotographic photoreceptor that is used repeatedly, an external electric and mechanical force such as corona charging, direct charging, image exposure, toner development, transfer process and surface cleaning is applied to the photoreceptor surface layer. To be added directly,
Durability against them is also required.

More specifically, durability against electrical deterioration due to ozone and nitrogen oxides during charging, mechanical deterioration in which the surface is worn or scratched due to discharge during charging, and rubbing of a cleaning member. Is required.

The surface of an electrophotographic photosensitive member is generally formed of a charge transporting material and a resin layer, and is considerably thin.

Among the above-mentioned disadvantages, mechanical deterioration is largely caused by the resin layer, and the selection of this resin layer is very important.

Among those having durability as described above, there is a polycarbonate resin having bisphenol Z as a skeleton.

This polycarbonate Z resin is characterized by having better mechanical strength than polycarbonate A resin which has been often used in the past, and showing good solubility in various kinds of organic solvents.

However, even if the above points are solved, the following problems still remain. (1) It is vulnerable to solvent cracks generated when an organic solvent or oil adheres to the surface. (2) The formed film main body does not show good lubricity, so that the electrophotographic photoreceptor is apt to be scratched, resulting in image defects, poor cleaning due to early deterioration of the cleaning blade, and reversal of the cleaning blade. May cause insufficient cleaning.

In the case of a polycarbonate Z resin, volume shrinkage is large when a coating film is formed, particularly when coating is performed from a solution by a casting method, and a stress often remains inside the coating film. For this reason,
It had the disadvantage of being relatively vulnerable to stress corrosion.
In order to solve this, for example, Japanese Patent Application Laid-Open No. 61-62040 is disclosed.
Japanese Patent Application Laid-Open No. 61-62 discloses a mixture of a polycarbonate A resin and a polycarbonate Z resin.
No. 039 discloses bisphenol A and bisphenol Z.
A method for reducing stress-corrosion cracking by copolymerizing is disclosed, but none of these methods is sufficient for solvent cracking.

Further, as described in the above (2), ordinary polycarbonate resin has low lubricity to a cleaning blade used in an electrophotographic process, and the cleaning blade is inverted due to the progress of durability. However, it has been pointed out that a cleaning failure occurs due to the above, and a scratch is generated due to a strong force applied to the electrophotographic photosensitive member.

In order to improve this, a method of adding Si oil, a method of copolymerizing a polydimethylsiloxane block with a polycarbonate resin as disclosed in JP-A-61-132954, and a method of 654
No. 44 discloses that (CH ₃ ) at the center of bisphenol A
_A method is known in which the _2- C = portion is changed to (CF ₃ ) ₂ -C =. However, the method of adding Si oil adversely affects electrophotographic characteristics, specifically, various characteristics such as sensitivity and residual potential. In addition, there is a drawback that the Si oil existing in the surface layer is lost due to the progress of durability and permanent lubricity cannot be obtained.

In addition, when the above-mentioned copolymer of methylsiloxane block is used, a resin using fluorine-based bisphenol has good lubricity, but these polymers have poor solubility. However, when coated, it tends to cause cloudiness and gelation, and when used as a surface layer of an electrophotographic photoreceptor, there are drawbacks such as rough surface and reduced mechanical strength.

[0021]

SUMMARY OF THE INVENTION An object of the present invention is to solve the problems of an electrophotographic photosensitive member having a conventional polycarbonate resin as a surface layer and to improve lubricity, storage stability and cleaning properties. Electrophotographic photoreceptor that maintains film strength while maintaining good solvent cracking properties, and therefore provides good images for a long period of time, and is easy to manufacture, and a process cartridge and an electrophotographic apparatus having the electrophotographic photoreceptor Is to provide.

[0022]

That is, the present invention relates to an electrophotographic photosensitive member having a photosensitive layer on a conductive support, wherein the surface layer of the electrophotographic photosensitive member has a structural unit represented by the following formula (1): An electrophotographic photosensitive member comprising a polymer having the following formula:

General formula (1)

[0024]

Embedded image In the formula (1), R _{1 to} R ₈ represent a hydrogen atom, a halogen atom such as fluorine, chlorine and bromine, and an alkyl group such as methyl, ethyl and propyl.

X represents an optionally substituted alkylene group such as methylene, ethylene and propylene, a cycloalkylene group such as cyclohexylene, an alkynylene group such as ethynylene, propynylene and butadinylene, phenylene,
It represents an arylene group such as biphenylene and terphenylene. Examples of the substituent which X may have include a halogen atom such as fluorine, chlorine and bromine, and an alkyl group such as methyl, ethyl and propyl.

[0026]

BEST MODE FOR CARRYING OUT THE INVENTION A polymer having a constitutional unit represented by the formula (1) can be used in a molecular weight range of 2,000 to 400,000.

Specific examples of the polymer having the structural unit represented by the formula (1) are shown below, but the present invention is not limited thereto.

[0028]

Embedded image

[0029]

Embedded image

[0030]

Embedded image

[0031]

Embedded image

The polymer having the structural unit represented by the formula (1) is synthesized by mixing a compound represented by the following formula (2) together with sodium hydroxide and an ammonium compound in methylene chloride and passing phosgene. .

Equation (2)

[0034]

Embedded image In the formula (2), R _{1 to} R ₈ and X have the same meanings as in the formula (1).

The electrophotographic photoreceptor of the present invention has a surface lubricity,
Improvements in storage stability, cleaning properties, solvent crack resistance, and film strength can be achieved.

Although the reasons for these are not clear, it is often the case that the three-dimensional arrangement of the polymer is increased due to the crosslinked structure or the nitrogen atom contained in the main chain molecule, and the entanglement of the polymer is more complicated. It is considered as a factor.

The polymer having the structural unit represented by the formula (1) can be used as a copolymer of the compound represented by the formula (2) and one or more other polycarbonate monomers.

The following are specific examples of the polycarbonate monomer, but the present invention is not limited thereto.

[0039]

Embedded image

When X in the formula (1) is an alkynylene group or an arylene group, the polymer having the structural unit represented by the formula (1) can be used alone as the charge transporting material.

The polymer having the structural unit represented by the formula (1) can be used alone as a binder resin, or can be used as a mixture with another resin. Mixable resins include polyester, polyurethane, polyarylate, polyethylene, polystyrene, polybutadiene, polycarbonate, polyamide, polypropylene, polyimide, polyamideimide, polysulfone, polyallyl ether, polyacetal, nylon, and phenolic resin.
Acrylic resin, silicone resin, epoxy resin, urea resin, allyl resin, alkyd resin, butyral resin and the like can be mentioned. Furthermore, reactive epoxy and (meth) acrylic monomers and oligomers can be used after mixing and curing. Particularly preferred is a mixture with an aromatic resin such as polycarbonate, polyallylate, polyallyl ether and polystyrene.

Specific examples of the fluorine atom-containing compound include:
Tetrafluoroethylene, hexafluoropropylene,
Trifluoroethylene, chlorotrifluoroethylene,
Examples include polymers such as vinylidene fluoride, vinyl fluoride, and perfluoroalkyl vinyl ether, and copolymers thereof. Further, inorganic fluorides and the like, such as carbon fluoride having a graphite structure substituted with a fluorine atom and oils substituted with a fluorine atom, may also be used.

When the fluorine atom-containing compound is a solid fine powder, its particle size is preferably in the range of 0.005 to 2.5 μm, and when its molecular weight is a polymer, it is 3,000.
It is preferably in the range of 10,000,000 to 10,000,000.
A more preferred range of the particle size is in the range of 0.01 to 0.7 μm.

In the case of the fluorine atom-containing compound in the form of solid fine powder, the compound is dispersed as a photoreceptor composition together with a polymer having the structural unit represented by the formula (1). Examples of the dispersion method include a sand mill, a ball mill, a roll mill, a homogenizer,
A nanomizer, a paint shaker, an ultrasonic wave, or the like is used. At the time of dispersion, an auxiliary fluorine-based surfactant,
It is also possible to use a graft polymer and a coupling agent.

As the content of the fluorine atom-containing compound,
The content of the layer to be contained is desirably 5 to 75% by weight.

The photosensitive layer in the electrophotographic photosensitive member of the present invention has a single layer or a laminated structure. In the case of a single-layer structure, generation and movement of photocarriers are performed in the same layer. In the case of a stacked structure, a charge generation layer that generates photocarriers and a charge transport layer in which carriers move are stacked. The surface layer may be formed on either the charge generation layer or the charge transport layer.

The single-layer photosensitive layer preferably has a thickness of 5 to 100 μm, more preferably 10 to 60 μm. The charge generating material and the charge transporting material preferably have a weight of 20 to 80% by weight, more preferably 30 to 70% by weight.

In the laminated type photoreceptor, the thickness of the charge generation layer is preferably 0.001 to 6 μm, more preferably 0.01 to 2 μm, and the amount of the charge generation material is 10 to 100% by weight. And more preferably 40 to 100% by weight. The thickness of the charge transport layer is 5
To 100 μm, more preferably 1 to 100 μm.
0 to 60 μm, and the amount of the charge transporting material is preferably 20 to 80% by weight, more preferably 30 to 70% by weight.
%.

The charge generating material used in the present invention includes phthalocyanine pigments, polycyclic quinone pigments, azo pigments, perylene pigments, indigo pigments, thioindigo pigments,
Examples include quinacridone pigments, azulhenium salt dyes, squarylium dyes, cyanine dyes, pyrylium dyes, thiapyrylium dyes, xanthene dyes, quinone imine dyes, triphenylmethane dyes, styryl dyes, selenium, selenium-tellurium, amorphous silicon, and cadmium sulfide.

The charge transporting materials used in the present invention include pyrene compounds, carbazole compounds, hydrazone compounds, N, N-dialkylaniline compounds, diphenylamine compounds, triphenylamine compounds, triphenylmethane compounds, pyrazoline compounds, styryl compounds, and the like. And stilbene compounds.

In the electrophotographic photosensitive member of the present invention, a protective layer may be laminated on the photosensitive layer. The thickness of the protective layer is 0.01 to 2
0 μm, more preferably 0.1 to
10 μm. The protective layer includes a charge generation material, a charge transport material, metals such as iron, copper, nickel, aluminum, titanium, tin, antimony, indium, lead, zinc, gold, and silver, and oxides, nitrides, and salts thereof. And an alloy, and may further contain a conductive material such as carbon.

Examples of the conductive support include metals, alloys such as iron, copper, nickel, aluminum, titanium, tin, antimony, indium, lead, zinc, gold and silver, and oxides, carbons and conductive resins thereof. Etc. can be used. The shapes include a cylindrical shape, a sheet shape, and a belt shape. The conductive material may be molded, but may be applied as a paint or deposited.

An undercoat layer may be provided between the conductive support and the photosensitive layer. The undercoat layer is mainly made of a binder resin, but may contain the conductive material or the acceptor.

As the binder resin, polyester, polyurethane, polyarylate, polyethylene, polystyrene, polybutadiene, polycarbonate, polyamide, polypropylene, polyimide, polyamideimide,
Polysulfone, polyallyl ether, polyacetal,
Nylon, phenolic resin, acrylic resin, silicone resin, epoxy resin, urea resin, allyl resin, alkyd resin, butyral resin, and the like.

As a method for producing the electrophotographic photosensitive member of the present invention, a method such as vapor deposition and coating is used. For application, methods such as bar coating, knife coating, roll coating, attritor, spray coating, dip coating, electrostatic coating, and powder coating can be used.

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 a shaft 2 in a direction of an arrow at a predetermined peripheral speed. The photoreceptor 1 rotates during the rotation process.
The peripheral surface is uniformly charged with a predetermined positive or negative potential by the primary charging means 3, and then receives image exposure light 4 from an image exposure means (not shown) such as slit exposure or laser beam scanning exposure. 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
The toner-developed image developed by the toner image is transferred from a paper supply unit (not shown) between the photoconductor 1 and the transfer unit 6 in synchronization with the rotation of the photoconductor 1 and fed to a transfer material 7 fed therefrom. The image is sequentially transferred by the transfer unit 6.

The transfer material 7 having undergone the image transfer is separated from the surface of the photoreceptor, introduced into the image fixing means 8 and subjected to image fixing, thereby being printed out of the apparatus as a copy.

The surface of the photoreceptor 1 after the image transfer is cleaned to remove the untransferred toner by the cleaning means 9, and the surface of the photoreceptor 1 is cleaned.
Is used for image formation repeatedly after the charge removal processing. When the primary charging unit 3 is a contact charging unit using a charging roller or the like, the pre-exposure is not necessarily required.

In the present invention, a plurality of components such as the above-described electrophotographic photosensitive member 1, primary charging means 3, developing means 5, and cleaning means 9 are integrally connected as a process cartridge. 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, a process in which at least one of the primary charging unit 3, the developing unit 5, and the cleaning unit 9 is integrally supported together with the photoreceptor 1 to form a cartridge, and is detachable from the apparatus main body using a guide unit such as the rail 12 of the apparatus main body. The cartridge 11 can be used.

When the electrophotographic apparatus is a copying machine or a printer, the image exposure light 4 is reflected and transmitted from the original, or the original is read by a sensor and converted into a signal, and the signal is emitted according to the signal. Laser beam scanning,
Light emitted by driving the LED array, driving the liquid crystal shutter array, and the like.

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,
It can be widely used in electrophotographic applications such as RT printers, LED printers, liquid crystal printers, and laser plate making.

[0064]

【Example】

Example 1 50 parts (parts by weight, hereinafter the same) of conductive titanium oxide powder coated with tin oxide containing 10% by weight of antimony oxide, 25 parts of phenolic resin, 20 parts of methyl cellosolve, 5 parts of methanol and silicone Oil (polydimethylsiloxane polyoxyalkylene copolymer,
0.002 parts of (average molecular weight: 3,000) was dispersed in a sand mill using φ1 mm glass beads for 2 hours to prepare a coating for a conductive layer. This paint was applied on a 30 mmφ aluminum cylinder by a dip coating method.
By drying for 0 minutes, a conductive layer having a thickness of 20 μm was formed.

Next, 5 parts of N-methoxymethylated nylon was dissolved in 95 parts of methanol to prepare a coating for an intermediate layer. This paint was applied on the conductive layer by a dip coating method, and dried at 100 ° C. for 20 minutes to form an intermediate layer having a thickness of 0.6 μm.

Next, the black angle 2θ ± 0.2 degrees in X-ray diffraction of CuKα is 9.0 degrees, 14.2 degrees, and 23.9 degrees.
Of oxytitanium phthalocyanine having a strong peak at 27.1 degrees and 27.1 degrees, 2 parts of polyvinyl butyral (trade name: SLECK BM2, manufactured by Sekisui Chemical Co., Ltd.) and 35 parts of cyclohexanone were mixed with a sand mill using φ1 mm glass beads. Disperse over time, then add ethyl acetate 6
0 parts were added to prepare a charge generation layer coating. This paint is applied on the intermediate layer by a dip coating method,
For 15 minutes to form a charge generation layer having a thickness of 0.2 μm.

Then, 10 parts of a triphenylamine compound having the following structural formula

[0068]

Embedded image And 10 parts of a polymer (Structural Unit Example No. 13, molecular weight 20,000) comprising a structural unit represented by the following formula:

[0069]

Embedded image It was dissolved in a mixed solvent of 25 parts of dichloromethane and 50 parts of monochlorobenzene to prepare a charge transport layer coating. This paint is applied on the charge generation layer by a dip coating method,
By drying at 120 ° C. for 60 minutes, a film thickness of 23 μ
m of a charge transport layer was formed, and an electrophotographic photosensitive member was prepared.

Using the prepared electrophotographic photosensitive member, surface lubricity, sedimentation over time, and solvent crack resistance were measured. Regarding the surface lubricity, a cleaning blade made of urethane rubber for a copying machine was used, which was brought into contact with the surface of the photoreceptor at a contact angle of 30 degrees, and the sliding resistance was measured using a HEIDON-14 type surface tester (Shinto Chemical Co., Ltd.) )).
Further, a urethane cleaning blade was pressed against this surface layer, stored at 75 ° C., and subjected to an acceleration test for precipitation. After 14 days, the photoreceptor was observed under a microscope to evaluate the presence or absence of precipitation. If no precipitate was observed, the test was continued until 30 days later. Regarding the solvent cracking property, finger grease was adhered to this surface layer, left at room temperature and normal humidity for 24 hours and 2 days, and then observed for the presence of solvent cracking with a microscope. Further, this photoreceptor is
After standing for 24 hours at 90 ° C. and 93% RH, the sheet was placed in Canon Corporation's LBP-NX and subjected to continuous paper passing for 10,000 sheets, and black spots caused by toner adhering to the photoreceptor surface were observed. did. Table 1 shows the results.

Examples 2 to 10 Example 1 was repeated except that the polymer used in the charge transport layer of Example 1 was changed to those shown in Table 1.
An electrophotographic photosensitive member was prepared and evaluated in the same manner as described above. Table 1 shows the results.

Comparative Examples 1 to 3 An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1 except that the polymer used for the charge transport layer in Example 1 was changed to the following. Table 1 shows the results.

[0073]

Embedded image

[0074]

[Table 1]

From the above results, it can be seen that the electrophotographic photosensitive member of the present invention is excellent.

Example 11 An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1 except that the charge transport layer of Example 1 was changed to the following. Table 2 shows the results.

10 parts of a hydrazone compound of the following structural formula:

[0078]

Embedded image 5 parts of a polymer composed of structural units represented by the following formula (Example of structural unit No. 10, molecular weight 50,000)

[0079]

Embedded image And 5 parts of a polymer (molecular weight: 60,000) comprising a structural unit represented by the following formula:

[0080]

Embedded image An electrophotographic photoreceptor was prepared in the same manner as in Example 1 using a paint dissolved in a mixed solvent of 25 parts of dichloromethane and 50 parts of monochlorobenzene.

[Comparative Example 4] In the preparation of the coating material for the charge transporting layer in Example 11, 10 parts of Compound 2 and a polymer (molecular weight: 60,00) comprising a structural unit represented by the following formula were used.
0) 10 parts

[0082]

Embedded image An electrophotographic photoreceptor was prepared and evaluated in the same manner as in Example 11, except that it was dissolved in 25 parts of dichloromethane and 50 parts of monochlorobenzene to prepare a paint for a charge transport layer. Table 2 shows the results.

[0083]

[Table 2]

From the above results, it can be seen that the electrophotographic photosensitive member of the present invention is excellent.

Example 12 An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 1 except that the charge transport layer of Example 1 was changed to the following. Table 3 shows the results.

10 parts of a styryl compound having the following structural formula:

[0087]

Embedded image 10 parts of a polymer comprising a structural unit represented by the following formula (Structural unit example No. 16, molecular weight 40,000),

[0088]

Embedded image Electrophotography in the same manner as in Example 1 using a coating material in which 3 parts of polytetrafluoroethylene fine powder (emulsion polymerized product, molecular weight: 40,000, average primary particle size: 0.20 μm), 25 parts of dichloromethane and 50 parts of monochlorobenzene were dispersed by a sand mill. A photoreceptor was made.

[Comparative Example 5] A polymer (molecular weight: 20,000) comprising 10 parts of compound 3 and a structural unit represented by the following formula in the preparation of the paint for a charge transport layer in Example 12.
10 copies,

[0090]

Embedded image An electrophotographic photoreceptor was prepared and evaluated using a coating material in which 3 parts of polytetrafluoroethylene fine powder (the same as in Example 12), 25 parts of dichloromethane and 50 parts of monochlorobenzene were dispersed by a sand mill in the same manner as in Example 12. Table 3 shows the results
Shown in

[0091]

[Table 3]

From the above results, it can be seen that the electrophotographic photosensitive member of the present invention is excellent.

Example 13 An electrophotographic photosensitive member was prepared in the same manner as in Example 1 except that the charge transport layer of Example 1 was changed to the following.

A coating solution was prepared by dissolving 20 parts of a polymer having the structural unit represented by the following formula (Structural unit No. 18, molecular weight 30,000) in a mixed solvent of 25 parts of dichloromethane and 50 parts of monochlorobenzene. An electrophotographic photosensitive member was prepared in the same manner as in Example 1.

[0095]

Embedded image

This was mounted on an LBP-NX manufactured by Canon Inc., and the dark portion potential was set to -700 V, and a laser beam of 802 nm was applied to the dark portion potential to measure the laser light amount at which the bright portion potential became -200 V. Table 4 shows the results.

Example 14 An electrophotographic photosensitive member was prepared in the same manner as in Example 1 except that the charge transport layer of Example 1 was changed to the following, and evaluated in the same manner as in Example 13. Table 4 shows the results.

A triphenylamine compound 1 of the following structural formula
0 copies and

[0099]

Embedded image 10 parts of a polymer (Structural Unit Example No. 18, molecular weight 30,000) consisting of structural units represented by the following formula:

[0100]

Embedded image An electrophotographic photoreceptor was prepared in the same manner as in Example 1, except that a paint dissolved in a mixed solvent of 25 parts of dichloromethane and 50 parts of monochlorobenzene was used.

[0101]

From the above results, the electrophotographic photoreceptor of the present invention can be used as a charge transporting layer even with a polymer alone.

[0103]

The electrophotographic photoreceptor of the present invention is excellent in lubricity, storage stability, cleaning properties, solvent crack resistance and abrasion resistance, and has an effect that a good image can be obtained for a long period of time. Further, the effect is also exerted in a process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member.

[Brief description of the drawings]

FIG. 1 is a diagram showing an example of a schematic configuration of an electrophotographic apparatus having a process cartridge having an electrophotographic photosensitive member of the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Electrophotographic photoreceptor of this 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

Claims (5)

[Claims] 1. An electrophotographic photosensitive member having a photosensitive layer on a conductive support, wherein the surface layer of the electrophotographic photosensitive member contains a polymer having a structural unit represented by the following formula (1). An electrophotographic photosensitive member characterized by the following. Embedded image (In the formula, R _{1 to} R ₈ represent a hydrogen atom, a halogen atom or an alkyl group. X represents an optionally substituted alkylene group, cycloalkylene group, alkynylene group or arylene group.) 2. The electrophotographic photoreceptor according to claim 1, wherein the surface layer contains a polymer having a structural unit represented by the formula (1) and an aromatic-containing resin. 3. The electrophotographic photoreceptor according to claim 1, wherein the surface layer contains a polymer having a structural unit represented by the formula (1) and a fluorine atom-containing compound. 4. An electrophotographic apparatus main body which integrally supports at least one member selected from the group consisting of an electrophotographic photosensitive member according to claim 1 and a charging device, a developing device and a cleaning device. A process cartridge which is detachably mounted on a process cartridge. 5. 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.