JP3010916B2 - Electrophotographic photosensitive member, electrophotographic apparatus having the same, and facsimile - 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 which can be widely used in electrophotographic applications such as an electrophotographic copying machine, a laser beam printer, a CRT printer, an electrophotographic plate making system, and a facsimile.

[0002]

2. Description of the Related Art Inorganic photoconductive materials such as selenium, cadmium sulfide and zinc oxide have been conventionally used as photoconductive materials for electrophotographic photosensitive members. On the other hand, organic photoconductive materials such as polyvinyl carbazole, oxadiazole and phthalocyanine have advantages such as non-pollution and high productivity as compared with inorganic photoconductive materials, but have low sensitivity and are difficult to be put to practical use. Therefore, several sensitization methods have been proposed, but as an effective method, it is known to use a function-separated type photoconductor in which a charge generation layer and a charge transport layer are laminated.

On the other hand, an electrophotographic photosensitive member is required to have predetermined sensitivity, electrical characteristics, and optical characteristics according to an applied electrophotographic process. Particularly, in the case of a photoreceptor that can be used repeatedly, since the surface layer of the photoreceptor is directly subjected to electrical and mechanical external forces such as corona charging, toner phenomenon, transfer to paper, and cleaning treatment, the durability against them is increased. Is required.

[0004] More specifically, degradation due to ozone generated during corona charging causes a decrease in sensitivity, a decrease in potential, and an increase in residual potential. In addition, the surface may be worn or scratched by rubbing. Durability is required.

Since the surface of the photosensitive member is coated with a resin, the performance of the resin is particularly important, and a resin having excellent durability has been demanded.

Recently, a polycarbonate resin having bisphenol A as a skeleton (hereinafter referred to as bisphenol A type polycarbonate) has been studied as a binder for the surface layer as a resin satisfying these requirements. Are not always satisfied with the bisphenol A type polycarbonate resin, and have the following problems.

[0007]

(1) The solubility of the resin is poor. It shows good solubility only in a part of halogenated aliphatic hydrocarbons such as dichloromethane and 1,2-dichloroethane. Since these halogenated aliphatic hydrocarbons have a low boiling point, when a photoreceptor is manufactured using a coating solution prepared with these solvents, the coated surface tends to be whitened. Also, it takes time and effort to control the process such as the solid content of the coating liquid.

(2) For solvents other than halogenated aliphatic hydrocarbons, tetrahydrofuran, dioxane,
Although it is partially soluble in cyclohexanone or a mixed solvent thereof, the solution has poor stability over time, such as gelation within several days, and is not suitable for producing a photoreceptor.

(3) Even if the above-mentioned drawbacks (1) and (2) are improved, a polycarbonate resin having only a main chain skeleton of bisphenol A or a bisphenol A derivative may have a solvent crack. Yes, they often appeared as cracks in the drum in electrophotographic copiers, and their drawbacks were noted.

[0010]

That is, the present invention relates to an electrophotographic photosensitive member having a functionally separated photosensitive layer on a conductive support, wherein the photosensitive layer has the following general formulas [1] and [2]:

[0011]

Embedded image (Wherein, R ₁ to R ₈ represent a hydrogen atom, a halogen atom, a methyl group or an ethyl group, A represents —S— or —O—, and B represents a divalent group derived from an aromatic compound). And the copolymerization ratio [1]: [2] is 3
0:70 to 70:30 (molar ratio), and a homopolymer having a structure represented by the general formula [1] and a general formula [2]
Wherein the total content of the homopolymer having the structure represented by the formula is 30% by weight or less of the whole polymer.

Further, the structure of the copolymer is preferably completely random.

The structure of the above copolymer can be summarized by one formula.

[0014]

Embedded image (R ₁ to R ₈ , A and B are the same as those described above, and X and Y indicate the copolymer composition ratio (molar ratio)).

The general formula [1] contained in the above copolymer
The copolymer component represented by is introduced to impart suitable flexibility to the polycarbonate resin, and does not hinder free rotation of the phenol group, and imparts ether bond flexibility to improve solvent cracking properties. Introduced in. Specific examples of such compounds include the following.

[0016]

Embedded image

[0017]

Embedded image The structure represented by the general formula [2] contained in the copolymer is introduced in order to give the copolymer an appropriate mechanical strength. Examples of such a compound include the following.

[0018]

Embedded image

[0019]

Embedded image

[0020]

Embedded image

[0021]

Embedded image Gel formation leading to image defects in electrophotography, ie, macroscopically, the storage stability of the solution cannot be prevented well by merely forming a copolymer. (Including a polymer) can be best achieved by reducing the symmetry of the polymer segment itself.

However, when homopolymers having the structures represented by the general formulas [1] and [2] are mixed, crystallization occurs partially in a block shape, and macro nucleation of gel nuclei occurs. Or the like, and the solvent crack resistance and the mechanical strength are significantly reduced.

That is, the present invention is characterized in that the above-mentioned homopolymer accounts for 30% by weight or less of the whole polymer, and is further characterized in that a random copolymer is used.

The coexistence of the homopolymer in such a copolymer can be easily determined by dissolving the copolymer in a suitable solvent and measuring the transparency of the solution. That is, if the amount of the homopolymer component is large, crystallization or gelation is caused, so that the transparency of the solution is reduced. More specifically, the percentage of the homopolymer in the copolymer can be measured by measuring the differential scanning calorimetry (DSC) and determining the area ratio of each component.

The above-mentioned structural units contained in the copolymer must be determined in consideration of scratch resistance, hardness and the like required according to the electrophotographic process. The ratio of the structure of the formula [1] to the structure of the formula [2] used at this time is determined in consideration of the fact that a random copolymer can be formed stably, the solvent crack resistance and the environmental stability with respect to the electrical characteristics are taken into consideration. In the ratio [1]: [2] = 30: 70
７０70: 30 (molar ratio). The above [1] and [2]
When the ratio is less than 30:70, the solvent cracking resistance is remarkably reduced, not only showing little effect on image defects in electrophotography, but also forming a block structure because random copolymerization does not proceed efficiently. The storage stability of the solution is significantly reduced. The above ratio is 70:30.
When it is larger than this, it was confirmed that it was difficult to form a polymer having a random structure itself, and that poor results were obtained in solvent crack resistance and image quality. As described above, the copolymer of the present invention has good properties in the above composition range.

The solubility of the polycarbonate resin having the component represented by the formula [7] is preferably 1 g or more, more preferably 5 g or more, per 100 cc of the aromatic hydrocarbon solvent and the halogenated aromatic hydrocarbon solvent. . This is because if the solubility is less than 1 g / 100 cc, for example, when preparing a charge transport layer solution, the viscosity of the solution is too low, so that an appropriate film thickness as the charge transport layer cannot be obtained.

Further, in consideration of durability, ie, abrasion resistance, scratch resistance, and viscosity at the time of production, ie, productivity, the molecular weight of the copolymer is 10% in terms of viscosity average molecular weight (Mv). 5,000 to 150,000, preferably 15,000 to 100,0.
It is preferably in the range of 00.

The copolymer used in the present invention is synthesized by interfacial polycondensation of the above-mentioned polyhydric phenols in the presence of phosgene. At this time, the purity and randomness of the copolymer are also reduced. Combined with due consideration.

The above-mentioned copolymer used in the present invention is preferably used as a binder resin for a photosensitive layer and a binder resin for a charge generation layer and a charge transport layer.

The present invention also relates to an electrophotographic photosensitive member having at least a photosensitive layer on a conductive support, wherein the surface layer of the photosensitive member has the following general formulas [11] and [12]:

[0031]

Embedded image (Wherein D is a linear, branched or cyclic alkylidene group having 1 to 10 carbon atoms, an alkylene group, an aryl-substituted alkylene group, an arylene group, -O-, -CO-, -S-,-
SO— or —SO ₂ —, R ₁₁ to R ₁₄ are a hydrogen atom, a halogen atom, an alkyl group or an aryl group having 1 to 4 carbon atoms, R ₁₅ to R ₁₈ are an alkyl group having 1 to 4 carbon atoms, a phenyl group or It represents a substituted phenyl group, and n represents a positive integer. ) And a homopolymer having a structure represented by the general formula [11] and a homopolymer having the structure represented by the general formula [1]
2) An electrophotographic photosensitive member, characterized in that the total content of homopolymers having the structure represented by 2) is 30% by weight or less of the whole polymer.

Further, it is preferable that the structure of the copolymer is completely random.

When the structure of the above copolymer is summarized by one formula, the following general formula [17]

[0034]

Embedded image (R ₁₁ to R ₁₈ , D and n are the same as described above, X and Y are copolymerization ratios, and m is the number of segments of polydiorganosiloxane).

Generation of a gel leading to an image defect in electrophotography, ie, macroscopically, the storage stability of a solution cannot be prevented well by merely forming a copolymer. Merging (including alternating copolymers)
By reducing the symmetry of the polymer segment itself, the best can be achieved.

However, when homopolymers composed of the compounds represented by the general formulas [11] and [12] are mixed, crystallization occurs due to partial block formation, and macro nucleation of gel nuclei occurs. Or the like, and the solvent crack resistance and the mechanical strength are significantly reduced.

That is, the present invention is characterized in that the above-mentioned homopolymer accounts for 30% by weight or less of the whole polymer, and is further characterized in that a random copolymer is used.

The coexistence of the homopolymer in such a copolymer can be easily determined by dissolving the copolymer in a suitable solvent and measuring the transparency of the solution. That is, if the amount of the homopolymer component is large, crystallization or gelation is caused, so that the transparency of the solution is reduced. More specifically, the content of the homopolymer in the copolymer can be measured by measuring the differential scanning calorimetry (DSC) and determining the area ratio of each component.

Specific examples of the compound for introducing the copolymer component represented by the above general formula [11] include polyvalent fail represented by the following structural formula, but are not limited to these. Absent.

[0040]

Embedded image

[0041]

Embedded image

[0042]

Embedded image

[0043]

Embedded image

[0044]

Embedded image Next, examples of the compound for introducing the copolymer component represented by the general formula [12] include a polyorganosiloxane derivative, but are not limited to these compounds.

[0045]

Embedded image The random copolymer of the present invention is synthesized by interfacial polycondensation in the presence of a polyhydric phenol having a structure represented by the formula [11], a polydiorganosiloxane derivative having a structure represented by the formula [12], and phosgene. You. The random copolymer of the present invention can be produced with high purity by interfacial polycondensation of such a copolymer component.

The molecular weight of the copolymer of the present invention may be in any range as long as a viscosity suitable for obtaining a suitable film thickness when applied as a solution can be obtained.
From the viewpoint of mechanical properties, the preferred molecular weight range is preferably 5,000 to 150,000 in terms of viscosity average molecular weight, and particularly, in the range where the viscosity average molecular weight or weight average molecular weight is in the range of 10,000 to 100,000. Preferably, there is. In addition, two or more kinds having a molecular weight can be used in combination. Further, a third copolymer component may be added to the copolymer of the present invention to form a copolymer.

According to the copolymer used in the present invention, a film having good lubricity can be obtained without deteriorating the electrical and mechanical properties. Furthermore, the copolymer has high solubility in very common solvents, for example, tetrahydrofuran, dioxane, cyclohexanone, benzene, toluene, xylene, monochlorobenzene or dichloromethane, dichlorobenzene, or a mixture thereof, Further, it has good characteristics in electrophotographic characteristics, production stability, and quality stability, such as no problem such as reduction in pot life due to gelation.

The copolymer of the present invention can be contained in a surface layer of an electrophotographic photoreceptor, particularly in a photosensitive layer and a surface protective layer, and is used as a binder resin and a charge generation layer of the photosensitive layer, and as a charge transport layer. In a laminated photosensitive layer having separated functions, it can be used as a binder resin for both layers.

When producing the electrophotographic photosensitive member of the present invention,
As the conductive support, metals such as aluminum and stainless steel, and cylindrical cylinders or films such as paper and plastic are used. On these supports, an undercoat layer having a barrier function and an adhesive function can be provided.

The undercoat layer is used for improving the adhesion of the photosensitive layer, improving the coatability, protecting the support, covering defects on the support, improving the charge injection property from the support, protecting the photosensitive layer against electrical breakdown, and the like. It is formed. Known materials for the undercoat layer include polyvinyl alcohol, poly-N-vinylimidazole, polyethylene oxide, ethyl cellulose, ethylene-acrylic acid copolymer, casein, polyamide, copolymerized nylon, glue, gelatin and the like. These are dissolved in a suitable solvent and applied on a support. The thickness at this time is preferably about 0.1 to 10 μm.

As the charge generating material in the electrophotographic photoreceptor of the present invention, selenium-tellurium, pyrylium, thiopyrylium dyes, various kinds of central metals and crystal systems, specifically, for example, α, β, γ, ε, X Copper phthalocyanine compound having a crystal type such as a type, A, B, C, E, F, H, I,
Titanyl phthalocyanine pigments having crystal forms of G, L, M, N, K, anthantrone pigments, dibenzpyrenequinone pigments, pyranthrone pigments, trisazo pigments,
Examples thereof include disazo pigments, azo pigments, indigo pigments, quinacridone pigments, asymmetric quinocyanine pigments, quinocyanines, and amorphous silicon described in JP-A-54-143645. Further, as the charge transporting material, pyrene, N-ethylcarbazole, N-isopropylcarbazole, N-methyl-N-phenylhydrazino-3-methylidene-9-ethylcarbazole, N, N-
Diphenylhydrazino-3-methylidene-9-ethylcarbazole, N, N-diphenylhydrazino-3-methylidene-10-ethylphenothiazine, N, N-diphenylhydrazino-3-methylidene-10-ethylphenoxazine, p- Diethylaminobenzaldehyde-N,
N-diphenylhydrazone, p-diethylaminobenzaldehyde-N-α-naphthyl-N-phenylhydrazone, p-pyrrolinodibenzaldehyde N, N-diphenylhydrazone, 1,3,3-trimethylindolenine-
ω-aldehyde-N, N-diphenylhydrazone, p-
Hydrazones such as diethylbenzaldehyde-3-methylbenzthiazolinone-2-hydrazone, 2,5-bis (p-diethylaminophenyl) -1,3,4-oxadiazole, 1-phenyl-3- (p- Diethylaminostyryl) -5- (p-diethylaminophenyl) pyrazoline, 1- [quinolyl (2)]-3- (p-diethylaminostyryl) -5- (p-diethylaminophenyl) pyrazoline, 1- [pyridyl (2)] -3- (p-
Diethylaminostyryl) -5- (p-diethylaminophenyl) pyrazoline, 1- [6-methoxy-pyridyl (2)]-3- (p-diethylaminostyryl) -5-
(P-diethylaminophenyl) pyrazolin, 1- [pyridyl (3)]-3- (p-diethylaminostyryl)
-5- (p-diethylaminophenyl) pyrazoline, 1
-[Pyridyl (2)]-3- (p-diethylaminostyryl) -5- (p-diethylaminophenyl) pyrazolin, 1- [pyridyl (2)]-3- (p-diethylaminostyryl) -4-methyl-5 -(P-diethylaminophenyl) pyrazolin, 1- [pyridyl (2)]-3-
(Α-methyl-p-diethylaminostyryl) -5-
(P-diethylaminophenyl) pyrazolin, 1-phenyl-3- (p-diethylaminostyryl) -4-methyl-5- (p-diethylaminophenyl) pyrazolin,
Pyrazolines such as 1-phenyl-3- (α-benzyl-p-diethylaminostyryl) -5- (p-diethylaminophenyl) pyrazoline and spiropyrazoline;
(P-diethylaminostyryl) -6-diethylaminobenzoxazole, 2- (p-diethylaminophenyl) -4- (p-dimethylaminophenyl) -5- (2
Oxazole compounds such as -chlorophenyl) oxazole, thiazole compounds such as 2- (p-diethylaminostyryl) -6-diethylaminobenzothiazole,
Triarylmethane compounds such as bis (4-doethylamino-2-methylphenyl) phenylmethane;
Bis (4-N, N-diethylamino-2-methylphenyl) heptane, 1,1,2,2-tetrakis-4-N,
Other triarylamine derivatives such as polyarylalkanes such as (N-dimethylamino-2-methylphenyl) ethane can be mentioned.

The charge generation layer contains the above charge generation material in an amount of 0.3.
It is well dispersed with a homogenizer, ultrasonic dispersion, a ball mill, a vibrating ball mill, a sand mill, an attritor, a roll mill or the like together with a binder resin and a solvent in an amount of up to 4 times, and then coated and dried. The thickness is desirably in the range of 0.05 to 2 μm.

The charge transport layer is applied and formed by dissolving the charge transport material and the binder resin in a solvent. The mixing ratio of the charge transport material and the binder resin is 2: 1.
The solvent is preferably about 1: 2. As the solvent, in addition to aromatic solvents such as toluene, xylene, and monochlorobenzene, cyclic ethers such as dioxane, tetrahydrofuran, and tetrahydropyran can be used. As a method of applying this solution, for example, a dip coating method, a spray coating method, a curtain coating method, a spin coating method and the like are known. For efficient mass production of electrophotographic photoreceptors, the immersion coating method is the best, and is made possible by using the polycarbonate resin of the present invention. 10 ℃ -2 after application
00 ° C., preferably at 20 ° C. to 150 ° C. for 5 minutes to 5 hours,
Ventilation drying or still drying is preferably performed for 10 minutes to 2 hours to obtain a charge transport layer having a thickness of 5 to 40 μm.

Various additives can be added to the charge transport layer used in the present invention.

FIG. 1 shows a schematic configuration example of a general transfer type electrophotographic apparatus using the electrophotographic photosensitive member of the present invention.

In FIG. 1, reference numeral 1 denotes a drum type photosensitive member of the present invention as an image carrier, which is driven to rotate at a predetermined peripheral speed in the direction of an arrow around a shaft 1a. The photoreceptor 1 is uniformly charged with a predetermined positive or negative potential on its peripheral surface by a charging means 2 during the rotation process, and then, in an exposure section 3, a light image exposure L (slit exposure / Laser beam scanning exposure). As a result, an electrostatic latent image corresponding to the exposure image is sequentially formed on the peripheral surface of the photoconductor.

The electrostatic latent image is then developed with toner by the developing means 4, and the developed toner image is transferred by the transfer means 5 between the photosensitive body 1 and the transfer means 5 from a paper feeding unit (not shown). The transfer material P is sequentially transferred onto the surface of the transfer material P which is synchronously taken out and fed.

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

The surface of the photoreceptor 1 after the image transfer is cleaned to remove the residual toner by the cleaning means 6 to be cleaned, and further subjected to the charge removal treatment by the pre-exposure means 7 to be repeatedly used for image formation.

As the uniform charging means 2 for the photosensitive member 1, a corona charging device is generally widely used. Transfer device 5
Also, corona transfer means are generally widely used. As an electrophotographic apparatus, a plurality of components such as the above-described photoreceptor, developing means, and cleaning means are integrally connected as an apparatus unit, and this unit is configured to be detachable from the apparatus body. May be. For example, photoconductor 1
The cleaning unit 6 and the cleaning unit 6 may be integrated into one device unit, and may be configured to be detachable using a guide unit such as a rail of the device body. At this time, the above-described device unit may be provided with a charging unit and / or a developing unit.

When the electrophotographic apparatus is used as a copying machine or a printer, the light image exposure L is a signal reflected from or transmitted from an original, or a signal is read from the original, and scanning of a laser beam, an LED array , Or by driving a liquid crystal shutter array.

When used as a facsimile printer, the light image exposure L is an exposure for printing received data. FIG. 2 is a block diagram showing an example of this case.

The controller 11 controls the image reading section 10 and the printer 19. The whole controller 11 is CP
It is controlled by U17. The read data from the image reading unit 10 is transmitted to the partner station through the transmission circuit 13. Data received from the partner station is sent to the printer 19 through the receiving circuit 12. The image memory 16 stores predetermined image data. The printer controller 18 controls a printer 19. 14 is a telephone.

The image information received from the line 15 (image information from a remote terminal connected via the line) is demodulated by the receiving circuit 12, then decoded by the CPU 17, and sequentially stored in the image memory 16. Is stored. When the image information of at least one page is stored in the memory 16, the image of the page is recorded. The CPU 17 reads one page of image information from the memory 16 and sends the decoded one page of image information to the printer controller 18. Upon receiving the image information of one page from the CPU 17, the printer controller 18 controls the printer 19 to record the image information of the page.

The CPU 17 is receiving the next page during recording by the printer 19.

As described above, image reception and recording are performed.

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,
RT printer, LED printer, LCD printer,
It can be widely used in electrophotographic applications such as laser plate making.

[0068]

Next, the present invention will be described with reference to examples.

Example 1 50 parts of conductive titanium oxide powder coated with tin oxide containing 10% of antimony oxide, 25 parts of phenol resin,
20 parts of methyl cellosolve, 5 parts of methanol, and 0.002 parts of silicone oil (polydimethylsiloxane polyoxyalkylene copolymer, average molecular weight: 3,000) were dispersed in a sand mill using φ1 mm glass beads for 2 hours to form a conductive layer. Paint was obtained. The paint was applied on an aluminum sheet by a wire bar and dried at 140 ° C. for 30 minutes to form a conductive layer having a thickness of 20 μm.

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 wire bar and dried at 100 ° C. for 20 minutes to form a 0.6 μm intermediate layer.

Next, the following structural formula

[0072]

Embedded image Was dispersed in a sand mill using φ1 mm glass beads for 12 hours, and then 60 parts of methyl ethyl ketone was dispersed in the mixture. In addition, a charge generation layer dispersion was obtained. This dispersion was applied on the above-mentioned intermediate layer with a wire bar and dried at 80 ° C. for 20 minutes to obtain a charge generation layer having a thickness of 0.2 μm.

Next, the structural formula

[0074]

Embedded image 10 parts of a hydrazone compound of the following structural formula

[0075]

Embedded image (Viscosity average molecular weight 2.16 × 10 ⁴ : DSC
10% or less of homopolymer by measurement)
Was dissolved in a mixed solvent of 20 parts of dichloromethane and 40 parts of monochlorobenzene, and this solution was coated on the above-mentioned charge generating layer with a wire bar and dried at 120 ° C. for 60 minutes to form a charge transporting layer having a thickness of 18 μm. Formed.

Next, abrasion resistance and electrophotographic characteristics were measured using this photoreceptor. Regarding the abrasion resistance, the abrasion tester No. A 101 Taber type was used, and commercially available copy paper was used as an abrasive. The electrophotographic characteristics were obtained by measuring photodischarge characteristics using a conductive glass of 10 cm ² . Further, finger oil was adhered to this surface layer, and after 24 hours, the presence or absence of solvent cracks was observed with a microscope. Table 1 shows the results.

Example 2 A copolymer having the following composition:

[0078]

Embedded image A photoreceptor was prepared in exactly the same manner as in Example 1 except that a charge transporting layer was formed using (a viscosity-average molecular weight of 2.51 × 10 ⁴ : a homopolymer mixture of 5% or less as measured by DSC). Then, various measurements were performed.

Table 1 shows the obtained results.

Example 3 A copolymer having the following composition (viscosity average molecular weight 9.56 ×
10 ⁴ : 30% of homopolymer mixed by DSC measurement
), And various measurements were made in the same manner as in Example 1, except that a charge transport layer was formed.

[0081]

Embedded image Table 1 shows the obtained results.

Example 4 A copolymer having the following composition (viscosity average molecular weight 3.28 ×
10 ⁴ : 10% of homopolymer mixed by DSC measurement
), And various measurements were made in the same manner as in Example 1, except that a charge transport layer was formed.

[0083]

Embedded image Table 1 shows the obtained results.

Example 5 A copolymer having the following composition:

[0085]

Embedded image A photoreceptor was prepared in exactly the same manner as in Example 1 except that a charge transporting layer was formed using a compound having a viscosity average molecular weight of 2.35 × 10 ^{4 and a} homopolymer mixture of 3% or less as measured by DSC. Various measurements were made. Table 1 shows the obtained results.

(Example 6) Charge generation material having the following structure

[0087]

Embedded image To form a charge generation layer and have the following composition:

[0088]

Embedded image (Viscosity average molecular weight 2.23 × 10 ⁴ : those having a homopolymer content of 5% or less by DSC measurement) and a charge transport material having the following structural formula

[0089]

Embedded image A photoreceptor was prepared in the same manner as in Example 1 except that a charge transport layer was formed using the same, and various measurements were performed.

Table 1 shows the obtained results.

Example 7 A copolymer having the following composition:

[0092]

Embedded image A photoreceptor was prepared in exactly the same manner as in Example 6, except that a charge transporting layer was formed using (a viscosity-average molecular weight of 2.98 × 10 ⁴ : a homopolymer mixture of 10% or less as measured by DSC). Various measurements were made.

Table 1 shows the obtained results.

Example 8 A copolymer having the following composition:

[0095]

Embedded image A photoreceptor was prepared in exactly the same manner as in Example 6, except that a charge transporting layer was formed using a compound having a viscosity average molecular weight of 2.34 × 10 ^{4 and a} homopolymer mixture of 5% or less as measured by DSC. Various measurements were made.

Table 1 shows the obtained results.

Example 9 A copolymer having the following composition:

[0098]

Embedded image (Viscosity average molecular weight 4.10 × 10 ⁴ : homopolymer mixed by 20% by DSC measurement) and a charge transport material having the following structural formula

[0099]

Embedded image The photoreceptor was prepared in the same manner as in Example 6 except that the charge transport layer was formed by using the method described above, and various measurements were performed.

Table 1 shows the obtained results.

Example 10 A copolymer having the following composition:

[0102]

Embedded image (Viscosity average molecular weight 2.86 × 10 ⁴ : those having a homopolymer content of 10% or less by DSC measurement) and a charge transport material having the following structural formula

[0103]

Embedded image The photoreceptor was prepared in the same manner as in Example 6 except that the charge transport layer was formed by using the method described above, and various measurements were performed.

Table 1 shows the obtained results.

Comparative Example 1 Polycarbonate Z (viscosity average molecular weight 3.6 × 10 ⁴ )
A photoreceptor was prepared in the same manner as in Example 1 except that a charge transport layer was formed using the same, and various measurements were performed.

Table 1 shows the obtained results.

(Comparative Example 2) A copolymer having the following structural formula

[0108]

(Viscosity average molecular weight 2.57 × 10 ⁴ : DSC
Homopoly by measurement The photoreceptor was prepared in the same manner as in Example 1 except that the charge transport layer was formed using a mixture having 35% of a mer), and various measurements were performed.

Table 1 shows the obtained results.

Comparative Example 3 A copolymer having the following structural formula

[0111]

Embedded image A photoreceptor was prepared in exactly the same manner as in Example 1 except that a charge transport layer was formed using (a viscosity-average molecular weight of 2.57 × 10 ⁴ : a mixture of a homopolymer of 5% by DSC measurement). And various measurements.

Table 1 shows the obtained results.

Comparative Example 4 A copolymer having the following structural formula

[0114]

Embedded image A photoreceptor was prepared in exactly the same manner as in Example 1 except that a charge transport layer was formed using (a viscosity-average molecular weight of 2.05 × 10 ⁴ : homopolymer mixed by 5% by DSC measurement). And various measurements.

Table 1 shows the obtained results.

The electrophotographic photoreceptor of the present invention has excellent durability, abrasion resistance, and abrasion resistance, and also has improved gelling properties and solvent crack resistance of a polycarbonate resin as a binder resin. Is easy to manufacture,
It is industrially very advantageous.

[0117]

[Table 1]

Example 11 50 parts of conductive titanium oxide powder coated with tin oxide containing 10% of antimony oxide, 25 parts of phenol resin,
20 parts of methyl cellosolve, 5 parts of methanol, and 0.002 parts of silicone oil (polydimethylsiloxane polyoxyalkylene copolymer, average molecular weight: 3,000) were dispersed in a sand mill using φ1 mm glass beads for 2 hours to form a conductive layer. Paint was obtained. This paint was dip-coated on an aluminum cylinder and dried at 140 ° C. for 30 minutes to form a conductive layer having a thickness of 20 μm.

Next, 5 parts of N-methoxymethylated nylon was dissolved in 95 parts of methanol to prepare a coating for an intermediate layer. This paint is dip-coated on the conductive layer,
After drying at 0 ° C. for 20 minutes, a 0.6 μm intermediate layer was formed.

Next, the following structural formula

[0121]

Embedded image Was dispersed in a sand mill using φ1 mm glass beads for 12 hours, and then 60 parts of methyl ethyl ketone was dispersed in the mixture. In addition, a charge generation layer dispersion was obtained. This dispersion was applied to the above-mentioned intermediate layer by dip coating,
After drying at 0 ° C. for 20 minutes, a charge generation layer having a thickness of 0.2 μm was obtained.

Next, the structural formula

[0123]

Embedded image 10 parts of a hydrazone compound of the following structural formula

[0124]

Embedded image (Viscosity average molecular weight 2.16 × 10 ⁴ : DSC
10% or less of homopolymer by measurement)
Was dissolved in a mixed solvent of 20 parts of dichloromethane and 40 parts of monochlorobenzene, and this solution was coated on the above-mentioned charge generating layer with a wire bar and dried at 120 ° C. for 60 minutes to form a charge transporting layer having a thickness of 18 μm. Formed.

Next, abrasion resistance and electrophotographic characteristics were measured using this photoreceptor. Regarding the abrasion resistance, the abrasion tester No. A 101 Taber type was used, and commercially available copy paper was used as an abrasive. The electrophotographic characteristics were obtained by measuring photodischarge characteristics using a conductive glass of 10 cm 2. Further, finger oil was adhered to this surface layer, and after 24 hours, the presence or absence of solvent cracks was observed with a microscope. Table 2 shows the results.

Example 12 A copolymer having the following composition:

[0127]

Embedded image A photoreceptor was prepared in the same manner as in Example 11 except that a charge transport layer was formed using (a viscosity-average molecular weight of 2.51 × 10 ⁴ : a homopolymer mixture of 5% or less as measured by DSC). Then, various measurements were performed.

Table 2 shows the obtained results.

Example 13 A copolymer having the following composition (viscosity average molecular weight 9.56 ×
10 ⁴ : 30% of homopolymer mixed by DSC measurement
), And various measurements were made in the same manner as in Example 11, except that a charge transport layer was formed.

[0130]

Embedded image Table 2 shows the obtained results.

Example 15 A copolymer having the following composition:

[0132]

Embedded image A photoreceptor was prepared in exactly the same manner as in Example 11 except that a charge transporting layer was formed using (having a viscosity average molecular weight of 2.35 × 10 ^{4, the} homopolymer content of which was 5% or less as measured by DSC). Various measurements were made.

Table 2 shows the obtained results.

(Example 16) A charge generating material having the following structure

[0135]

Embedded image To form a charge generation layer and have the following composition:

[0136]

Embedded image (Viscosity average molecular weight 2.23 × 10 ⁴ : those having a homopolymer content of 5% or less by DSC measurement) and a charge transport material having the following structural formula

[0137]

Embedded image Example 11 except that a charge transport layer was formed using
A photoreceptor was prepared in exactly the same manner as described above, and various measurements were made.

The results are shown in Table 2.

Example 17 A copolymer having the following composition:

[0140]

Embedded image A photoreceptor was prepared in the same manner as in Example 16 except that a charge transport layer was formed by using (viscosity average molecular weight 2.98 × 10 ⁴ : homopolymer contained by 10% or less by DSC measurement). Various measurements were made.

Table 2 shows the obtained results.

Example 18 A copolymer having the following composition:

[0143]

Embedded image A photoconductor was prepared in the same manner as in Example 16 except that a charge transporting layer was formed using (a viscosity average molecular weight of 2.34 × 10 ^{4, in which the} homopolymer was mixed by 5% or less by DSC measurement). Various measurements were made.

Table 2 shows the obtained results.

Example 19 A copolymer having the following composition:

[0146]

Embedded image (Viscosity average molecular weight 4.10 × 10 ⁴ : homopolymer mixed by 20% by DSC measurement) and a charge transport material having the following structural formula

[0147]

Embedded image Example 16 except that the charge transport layer was formed using
A photoreceptor was prepared in exactly the same manner as described above, and various measurements were made.

Table 2 shows the obtained results.

Example 20 A copolymer having the following composition:

[0150]

Embedded image (Viscosity average molecular weight 2.86 × 10 ⁴ : those having a homopolymer content of 10% or less by DSC measurement) and a charge transport material having the following structural formula

[0151]

Embedded image Example 16 except that the charge transport layer was formed using
A photoreceptor was prepared in exactly the same manner as described above, and various measurements were made.

Table 2 shows the obtained results.

Comparative Example 5 Polycarbonate Z (viscosity average molecular weight 3.6 × 10 ⁴ )
Example 11 except that a charge transport layer was formed using
A photoreceptor was prepared in exactly the same manner as described above, and various measurements were made.

Table 2 shows the obtained results.

(Comparative Example 6) Copolymer of the following structural formula

[0156]

Embedded image A photoreceptor was prepared in exactly the same manner as in Example 11 except that a charge transport layer was formed using the same (viscosity average molecular weight: 2.57 × 10 ⁴ : homopolymer mixed by DSC measurement: 35%). And various measurements.

Table 2 shows the obtained results.

(Comparative Example 7) A copolymer having the following structural formula

[0159]

Embedded image A photoreceptor was prepared in the same manner as in Example 11 except that a charge transport layer was formed using (a viscosity-average molecular weight of 2.57 × 10 ⁴ : a mixture of a homopolymer of 5% by DSC measurement). And various measurements.

Table 2 shows the obtained results.

(Comparative Example 8) A copolymer having the following structural formula

[0162]

Embedded image A photoreceptor was prepared in the same manner as in Example 11 except that a charge transport layer was formed using (viscosity average molecular weight 2.05 × 10 ⁴ : homopolymer mixed in 5% by DSC measurement). And various measurements.

Table 2 shows the obtained results.

The electrophotographic photoreceptor of the present invention has excellent durability, abrasion resistance and abrasion resistance, and also improves the gelling property of a polycarbonate resin as a binder resin and the solvent crack resistance. Therefore, it is easy to manufacture, and is extremely industrially advantageous.

[0165]

[Table 2]

(Example 21) 50 parts of conductive titanium oxide powder coated with tin oxide containing 10% of antimony oxide, 25 parts of phenol resin,
20 parts of methyl cellosolve, 5 parts of methanol, and 0.002 parts of silicone oil (polydimethylsiloxane polyoxyalkylene copolymer, average molecular weight: 3,000) were dispersed in a sand mill using φ1 mm glass beads for 2 hours to form a conductive layer. Paint was obtained. This paint was applied on an aluminum sheet with a wire bar and dried at 140 ° C. for 30 minutes to obtain a conductive layer having a thickness of 20 μm.

Next, N-methoxymethylated nylon 5
Was dissolved in 95 parts of methanol to obtain an undercoat paint.
This paint was applied on the conductive layer and dried at 100 ° C. for 20 minutes to form a 0.6 μm undercoat layer. Then, the following structural formula

[0168]

Embedded image Was dispersed in a sand mill using φ1 mm glass beads for 12 hours, and then 60 parts of methyl ethyl ketone was dispersed in the mixture. In addition, a charge generation layer dispersion was obtained. This dispersion was applied on the above-mentioned intermediate layer with a wire bar and dried at 80 ° C. for 20 minutes to obtain a charge generation layer having a thickness of 0.2 μm.

Next, the structural formula

[0170]

Embedded image Of a styryl compound of the formula:

[0171]

Embedded image (A viscosity average molecular weight of 2.10 ×
10 ⁴ : those having a homopolymer content of 5% or less by DSC measurement) 10 parts are dissolved in a mixed solvent of 20 parts of dichloromethane and 40 parts of monochlorobenze, and the solution is coated on the above-mentioned charge generating layer with a wire bar. At 120 ° C
After drying for a minute, a charge transporting layer having a thickness of 18 μm was formed to obtain a photoconductor.

A rotary taper abrasion test was performed on the surface layer of this photoreceptor.
No weight loss due to abrasion was observed even after repeated friction, indicating very good abrasion resistance. Using this photoreceptor, a sliding resistance against a urethane cleaning blade at a load of 10 g was measured using a surface property tester (HEIDON-14, manufactured by Shinto Kagaku Co., Ltd.). The output value was 100 mV.

In this case, the smaller the output value on the chart recorder, the smaller the slip resistance, that is, the higher the lubricity. Table 4 shows the results.

(Example 22) In place of the copolymer used in Example 21, the following formula was used.

[0175]

Embedded image (A viscosity average molecular weight of 2.10 ×
10 ⁴ : 30% of homopolymer mixed by DSC measurement
A photoreceptor was prepared and evaluated in the same manner as in Example 21 except that the photoreceptor was used.

Table 4 shows the results.

Example 23 Instead of the copolymer used in Example 21, the following formula was used.

[0178]

Embedded image (A viscosity average molecular weight of 3.
05 × 10 ⁴ : A photoreceptor was prepared and evaluated in the same manner as in Example 21 except that a mixture of 10% of homopolymer by DSC measurement was used.

Table 4 shows the results.

(Example 24) In place of the copolymer used in Example 21, the following formula was used.

[0181]

Embedded image (A viscosity average molecular weight of 4.
05 × 10 ⁴ : A photoreceptor was prepared and evaluated in the same manner as in Example 21 except that a mixture of 10% of homopolymer by DSC measurement was used.

Table 4 shows the results. (Example 25)

Instead of the copolymer used in Example 21,
The following formula

[0184]

Embedded image (A viscosity average molecular weight of 2.
03 × 10 ⁴ : A photoreceptor was prepared and evaluated in the same manner as in Example 21 except that a mixture of 20% of homopolymer by DSC measurement was used.

Table 4 shows the results.

(Example 26) Instead of the charge generation material used in Example 21, the following formula was used.

[0187]

Embedded image Using a diazo pigment represented by

[0188]

Embedded image The hydrazone compound represented by the following formula was used.
A photoreceptor was prepared and evaluated in the same manner as in Example 1.

Table 4 shows the results.

Example 27 Instead of the copolymer used in Example 26, the following formula was used.

[0191]

Embedded image A photoreceptor was prepared and evaluated in the same manner as in Example 26 using the copolymer shown in (viscosity average molecular weight: 2.10 × 10 ⁴ : homopolymer mixed by 5% by DSC measurement). .

Table 4 shows the results.

(Example 28) 50 parts of conductive titanium oxide powder coated with tin oxide containing 10% of antimony oxide, 25 parts of phenol resin,
20 parts of methyl cellosolve, 5 parts of methanol, and 0.002 parts of silicone oil (polydimethylsiloxane polyoxyalkylene copolymer, average molecular weight: 3,000) were dispersed in a sand mill using φ1 mm glass beads for 2 hours to form a conductive layer. Paint was obtained. This paint was applied on an aluminum sheet with a wire bar and dried at 140 ° C. for 30 minutes to obtain a conductive layer having a thickness of 20 μm.

Subsequently, N-methoxymethylated nylon 5
Was dissolved in 95 parts of methanol to obtain an undercoat paint.
This paint was applied on the conductive layer and dried at 100 ° C. for 20 minutes to form a 0.6 μm undercoat layer. Then, the following structural formula

[0195]

Embedded image Was dispersed in a sand mill using φ1 mm glass beads for 12 hours, and then 60 parts of methyl ethyl ketone was dispersed in the mixture. In addition, a charge generation layer dispersion was obtained. This dispersion was applied on the above-mentioned intermediate layer with a wire bar and dried at 80 ° C. for 20 minutes to obtain a charge generation layer having a thickness of 0.2 μm.

Next, the structural formula

[0197]

Embedded image Of a styryl compound of the formula:

[0198]

Embedded image (A viscosity average molecular weight of 2.10 ×
10 ⁴ : 10% of homopolymer mixed by DSC measurement
The following was dissolved in a mixed solvent of 10 parts, 20 parts of dichloromethane and 40 parts of monochlorobenzene, and the solution was applied on the above-mentioned charge generating layer with a wire bar, dried at 120 ° C. for 60 minutes, and dried to a film thickness of 18 μm. Was formed into a photoreceptor, and evaluated in the same manner as in Example 21. Table 4 shows the results.

(Example 29) Instead of the disazo pigment used in Example 28, the following structural formula

[0200]

Embedded image A photoconductor was prepared and evaluated in the same manner as in Example 21, except that the photoconductor was prepared using a disazo pigment having the following formula:

Table 4 shows the results.

Examples 30 to 34 Copolymers (DSC) having the structures and molecular weights shown in Table 3
A photoreceptor was prepared and evaluated in the same manner as in Example 21 for the case where the mixture of polymers was 30% by measurement).

The results are shown in Table 4 .

[0204]

[Table 3]

Comparative Example 9 Instead of the copolymer used in Example 21, the following formula was used.

[0206]

Embedded image (A viscosity average molecular weight of 4.
0 × 10 ⁴ : 3 mixed homopolymers by DSC measurement
A photoreceptor was prepared and evaluated in the same manner as in Example 21 except that the photoreceptor was used.

The results are shown in Table 4 .

(Comparative Example 10) In place of the copolymer used in Example 21, the following formula was used.

[0209]

Embedded image (A viscosity average molecular weight of 2.
05 × 10 ⁴ : A photoreceptor was prepared and evaluated in the same manner as in Example 21 except that dichloromethane was used as a solution of the same (having a homopolymer content of 35% by DSC measurement).

The results are shown in Table 4 .

(Example 35) 50 parts of conductive titanium oxide powder coated with tin oxide containing 10% of antimony oxide, 25 parts of phenol resin,
20 parts of methyl cellosolve, 5 parts of methanol, and 0.002 parts of silicone oil (polydimethylsiloxane polyoxyalkylene copolymer, average molecular weight: 3,000) were dispersed in a sand mill using φ1 mm glass beads for 2 hours to form a conductive layer. Paint was obtained. This paint was applied on an aluminum sheet with a wire bar and dried at 140 ° C. for 30 minutes to obtain a conductive layer having a thickness of 20 μm.

Next, N-methoxymethylated nylon 5
Was dissolved in 95 parts of methanol to obtain an undercoat paint.
This paint was applied on the conductive layer and dried at 100 ° C. for 20 minutes to form a 0.9 μm undercoat layer. Then, the following structural formula

[0213]

Embedded image Was dispersed in a sand mill using φ1 mm glass beads for 12 hours, and then 60 parts of methyl ethyl ketone was dispersed in the mixture. In addition, a charge generation layer dispersion was obtained. This dispersion was applied on the above-mentioned intermediate layer with a wire bar and dried at 80 ° C. for 20 minutes to obtain a charge generation layer having a thickness of 0.2 μm.

Next, the structural formula

[0215]

Embedded image Of a styryl compound of the formula:

[0216]

Embedded image (A viscosity average molecular weight of 2.10 ×
10 ⁴ : Dissolved in a mixed solvent of 10 parts, 20 parts of dichloromethane, and 40 parts of monochlorobenzene by a DSC measurement with a wire bar, and the solution was coated on the above-mentioned charge generating layer with a wire bar. 6 at 120 ° C
After drying for 0 minute to form a charge transport layer having a film thickness of 18 μm, the photosensitive member is mounted on a color copier having a process of charging, exposing, developing, transferring and cleaning to repeatedly produce an image. When the image defects due to the reversal of the cleaning blade were evaluated, no scratches or abrasion occurred on the surface of the photoreceptor even after the running of 1,000 sheets, and the film was filled even after the running of 10,000 sheets. No deterioration due to durability was observed in the image quality that caused the occurrence of poor cleaning or the reversal of the cleaning blade, and no decrease in film thickness due to abrasion was observed with the eddy current film thickness meter.

Example 36 In place of the disazo pigment used in Example 35, the following formula was used.

[0218]

Embedded image Using a disazo pigment having a structure represented by the following formula,

[0219]

Embedded image A photoreceptor was prepared in the same manner as in Example 35, except that a hydrazone compound having the structure shown in Table 1 was used as a charge transporting agent, and was evaluated using a commercially available laser printer. No cleaning blade reversal during that time, no image defects due to ghosts on the surface of the photoreceptor occurred, and no decrease in the film thickness of the surface layer due to abrasion was observed with the eddy current film thickness meter.

(Comparative Example 11) Instead of the copolymer used in Example 35, the following formula

[0221]

Embedded image A polymer having a structure represented by the formula (viscosity average molecular weight 4.0
A photoreceptor was prepared in the same manner as in Example 35 except that × 10 ⁴ ) was used, and the evaluation was performed in the same manner as in Example 35. Scratch due to rubbing with the cleaning blade occurred, and especially in the early stage of the endurance, the cleaning blade was frequently inverted. Further, a deep scratch was generated by the rubbing, so that deterioration of image quality was observed, such as progress of durability and deterioration of reproducibility of small points. The decrease in film thickness due to wear after 10,000 sheets was 8 μm.

(Example 37) A photoconductor was manufactured in the same manner as in Comparative Example 10, and Example 2 was repeated.
5 parts of the copolymer used in 1 were dissolved in 95 parts of chlorobenzene to obtain a coating for a protective layer. This paint is spray-coated on the photoreceptor and dried at 120 ° C. for 60 minutes to form a 2.5 μm
Was obtained. When this was evaluated in the same manner as in Example 35, the photoreceptor had good surface lubricity even after 1,000 sheets, and no reduction in image quality, reversal of the cleaning blade, and the like were observed.

(Example 38) In place of the paint for a protective layer obtained in Example 37, 2 parts of fine powder of tin oxide, 10 parts of the copolymer used in Example 21 and
A photoreceptor was prepared and evaluated in the same manner as in Example 32 except that a dispersion liquid composed of 100 parts of monochlorobenzene was used. The photoreceptor showed good surface lubricity even after running for 1,000 sheets. No deterioration in image quality, reversal of the cleaning blade, etc. were observed.

(Example 39) Instead of the protective layer coating obtained in Example 37, a charge transport material represented by the following structural formula

[0225]

Embedded image A photoreceptor was prepared and evaluated in the same manner as in Example 32 except that a coating composed of 10 parts of the copolymer used in Example 21 and 100 parts of monochlorobenzene was used. Even after running, the photoreceptor had good surface lubricity, and no deterioration in image quality or reversal of the cleaning blade was observed.

According to the present invention, there is provided an electrophotographic photoreceptor having sufficient mechanical strength and lubricity and excellent electrophotographic characteristics.

[0227]

[Table 4]

[0228]

As described above, according to the present invention, an electrophotographic photosensitive member having excellent durability and abrasion resistance was obtained.

[Brief description of the drawings]

FIG. 1 is a schematic view of a general electrophotographic apparatus.

FIG. 2 is a block diagram of a facsimile using the electrophotographic apparatus as a printer.

[Description of Signs] 1 photoreceptor 2 charging means 3 exposure unit 4 developing means 5 transfer means 6 cleaning means 7 pre-exposure means 8 image fixing means

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Hiroshi Aoto 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon Inc. (72) Inventor Yoshiyuki Yoshihara 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside Canon Inc. (72) Inventor Hideki Anayama 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon Inc. (72) Inventor Shinya Mayama 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon Inc. (56) References JP-A-3-273255 (JP, A) JP-A-2-236557 (JP, A) JP-A-4-37763 (JP, A) JP-A-2-240657 (JP, A) JP-A-4-163559 (JP, A) JP-A-5-72753 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) G03G 5/05 101 G03G 5/147 502

Claims (14)

(57) [Claims] 1. An electrophotographic photosensitive member having a functionally separated photosensitive layer on a conductive support, wherein the photosensitive layer has the following general formulas [1] and [2]: (Wherein, R ₁ to R ₈ represent a hydrogen atom, a halogen atom, a methyl group or an ethyl group, A represents —S— or —O—, and B represents a divalent group derived from an aromatic compound). And the copolymerization ratio [1]: [2] is 3
0:70 to 70:30 (molar ratio), and a homopolymer having a structure represented by the general formula [1] and a general formula [2]
An electrophotographic photoreceptor characterized in that the total content of homopolymers having the structure represented by the formula is 30% by weight or less of the whole polymer. 2. The electrophotographic photoreceptor according to claim 1, wherein said copolymer is a random copolymer. 3. The compound according to claim 1, wherein B is the following general formula [3]: 3. The electrophotographic photosensitive member according to claim 1, wherein R ₁ to R ₈ are the same as those described above. 4. The above-mentioned B is represented by the following general formula [4]: 3. The electrophotographic photosensitive member according to claim 1, wherein R ₁ to R ₈ are the same as those described above. 5. The method according to claim 4, wherein B is a compound represented by the following general formula [5]: 3. The electrophotographic photosensitive member according to claim 1, wherein R ₁ to R ₈ are the same as those described above. 6. The above-mentioned B is represented by the following general formula [6]: 3. The electrophotographic photosensitive member according to claim 1, wherein R ₁ to R ₈ are the same as those described above. 7. An electrophotographic photosensitive member having at least a photosensitive layer on a conductive support, wherein the surface layer of the photosensitive member has the following general formulas [11] and [12]: (Wherein D is a linear, branched or cyclic alkylidene group having 1 to 10 carbon atoms, an alkylene group, an aryl-substituted alkylene group, an arylene group, -O-, -CO-, -S-,-
SO— or —SO ₂ —, R ₁₁ to R ₁₄ are a hydrogen atom, a halogen atom, an alkyl group or an aryl group having 1 to 4 carbon atoms, R ₁₅ to R ₁₈ are an alkyl group having 1 to 4 carbon atoms, a phenyl group or It represents a substituted phenyl group, and n represents a positive integer. ) And a homopolymer having a structure represented by the general formula [11] and a homopolymer having the structure represented by the general formula [1]
2) An electrophotographic photoreceptor, wherein the total content of the homopolymer having the structure represented by 2) is 30% by weight or less of the whole polymer. 8. The electrophotographic photoconductor according to claim 7, wherein the copolymer is a random copolymer. 9. The structure represented by the general formula [11] is represented by the following formula [13]: The electrophotographic photosensitive member according to claim 7 or 8, wherein 10. The structure represented by the general formula [11] is represented by the following formula [14]: The electrophotographic photosensitive member according to claim 7 or 8, wherein 11. The structure represented by the general formula [11] is represented by the following formula [15]: The electrophotographic photosensitive member according to claim 7 or 8, wherein 12. The structure represented by the general formula [11] is represented by the following formula [16]: The electrophotographic photosensitive member according to claim 7 or 8, wherein 13. An electrophotographic apparatus comprising the electrophotographic photoreceptor according to claim 1. Description: 14. A facsimile comprising: the electrophotographic photosensitive member according to claim 1; and receiving means for receiving image information from a remote terminal.