JPH10104861A - Electrophotographic photoreceptor, process cartridge having the electrophotographic photoreceptor, and electrophotographic apparatus - Google Patents

Abstract

PROBLEM TO BE SOLVED: To ensure superior electrophotographci characteristics, durability and environmental stability and to avoid cracking and crystallization by forming a photosensitive layer contg. a specified fluorene compd. and a specified stilbene compd. SOLUTION: This electrophotographci photoreceptor has a photosensitive layer contg. a fluorene compd. represented by formula I and a stilbene compd. represented by formula II. In the formula I, each of R1 and R2 is optionally substd. alkyl, etc., each of R3 -R10 is optionally substd. diarylamino, etc., and at least two of R3 -R10 are optionally substd. diarylamino. In the formula II, each of Ar3 and Ar4 is optionally substd. aryl, etc., Ar5 is optionally substd. arylene, etc., each of Ar11 and Ar12 is optionally substd. alkyl, etc., (n) is 1 or 2, and in the case of n=1, R11 and R12 may form a ring by bonding to each other.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an electrophotographic photosensitive member, and more particularly, to an electrophotographic photosensitive member having improved electrophotographic characteristics. Further, the present invention relates to a process cartridge and an electrophotographic apparatus having the electrophotographic photosensitive member.

[0002]

2. Description of the Related Art In recent years, research and development of an electrophotographic photosensitive member using an organic photoconductive substance have been actively conducted due to advantages such as high safety, excellent productivity, and low cost. Has been proposed and put into practical use.

However, an electrophotographic photoreceptor containing a photoconductive polymer represented by poly-N-vinylcarbazole and a charge transfer complex formed from 2,4,7-trinitrofluorene or the like as main components has been proposed. They were not always satisfactory in terms of sensitivity, durability, residual potential and the like.

On the other hand, a function-separated type electrophotographic photoreceptor in which a charge generation function and a charge transport function are shared by different substances, respectively, has remarkably improved sensitivity and durability, which have been disadvantages of conventional organic photoreceptors. Brought. Further, the function-separated type photoreceptor has the advantage that the material selection range of the charge generating substance and the charge transporting substance is wide, and an electrophotographic photoreceptor having arbitrary characteristics can be relatively easily prepared.

[0005] As the charge generating material, various azo pigments,
Polycyclic quinone pigments, phthalocyanine pigments, cyanine dyes,
Squaric acid dyes and pyrylium salt dyes are known.

Examples of the charge transport material include pyrazoline compounds such as JP-B-52-4188, hydrazone compounds such as JP-B-55-42380 and JP-A-55-52063, and JP-B-58-32372. JP, JP-A-61-132855, JP-A-62
JP-A-20854, JP-A-2-230255, JP-A-3-78756, JP-A-7-72639 and the like, triphenylamine compounds, JP-A-54-15
Stilbene compounds and the like disclosed in JP-A-19555 and JP-A-58-198043 are known.

[0007]

However, with the recent improvement in image quality and durability, further improvements in sensitivity and durability have been demanded.

In recent years, printers, copiers, facsimile machines, and the like using electrophotographic photosensitive members have been used in a wide variety of fields, and it has been required to provide a stable image even in various environments. Strictly required.

Further, in recent years, a charge transport layer has cracks caused by providing a protective layer on the photosensitive layer, storing the photoreceptor in a copying machine or a printer for a long time, and an image caused by crystallization of the charge transport material. Defects have been highlighted as a major problem.

An object of the present invention is to provide an electrophotographic photosensitive member having excellent electrophotographic characteristics and excellent durability.

Another object of the present invention is to provide an electrophotographic photosensitive member having excellent environmental stability.

Another object of the present invention is to provide an electrophotographic photosensitive member having excellent crack resistance and excellent crystal resistance.

Another object of the present invention is to provide a process cartridge and an electrophotographic apparatus having the above electrophotographic photosensitive member.

[0014]

That is, the present invention relates to an electrophotographic photosensitive member having a photosensitive layer on a support, wherein the photosensitive layer has the following formula (1):

[0015]

[Outside 7] (Wherein R ₁ and R ₂ are the same or different and are each a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a ring group formed by bonding to each other, and hydrogen Represents an atom, R ₃
To R ₁₀ are the same or different and each is a substituted or unsubstituted diarylamino group, a substituted or unsubstituted alkyl group,
It represents a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a halogen atom, a nitro group and a hydrogen atom, and at least two of R _{3 to} R ₁₀ represent a substituted or unsubstituted diarylamino group. ) And a fluorene compound represented by the following formula (3):

[0016]

[Outside 8] (Wherein, Ar ₃ and Ar ₄ are the same or different and represent a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group, and Ar ₅ is a substituted or unsubstituted arylene group and a substituted or unsubstituted R ₁₁ and R ₁₂ are the same or different and represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a hydrogen atom. , N represents 1 or 2, and when n is 1, R ₁₁ and R ₁₂
May combine with each other to form a ring. An electrophotographic photoreceptor characterized by containing a stilbene compound represented by the following formula:

Further, the present invention is a process cartridge and an electrophotographic apparatus having the above electrophotographic photosensitive member.

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION In the formula (1), examples of the alkyl group include a methyl group, an ethyl group, a propyl group and a butyl group, and examples of the aryl group include a phenyl group, a naphthyl group and a pyrenyl group. The aralkyl group includes a benzyl group, a phenethyl group and a naphthylmethyl group. Examples of the ring formed by combining R ₁ and R ₂ include a cyclopentane ring and a cyclohexane ring. Examples of the diarylamino group include a diphenylamino group and a dinaphthylamino group, and include the following formula (2)

[0019]

[Outside 9] (In the formula, Ar ₁ and Ar ₂ are the same or different and represent a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group.) Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the formula (2), examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group and a pyrenyl group, and examples of the heterocyclic group include a pyridyl group, a thienyl group and a furyl group.

In the formula (3), examples of the alkyl group include a methyl group, an ethyl group, a propyl group and a butyl group.
Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group and a pyrenyl group, and examples of the heterocyclic group include a pyridyl group, a phenyl group, a furyl group and a quinolyl group. Examples of the arylene group include groups such as phenylene and naphthylene, and examples of the divalent heterocyclic group include divalent groups such as a pyridine ring, a thiophene ring, a furan ring, and a quinoline ring. The ring formed by the bonding of R ₁₁ and R ₁₂ includes indene, 5H-
Dibenzo [a, d] cycloheptene and 10,11-dihydro-5H-dibenzo [a, d] cycloheptene;

Examples of the substituent which these groups may have include alkyl groups such as methyl group, ethyl group, propyl group and butyl group, aralkyl groups such as benzyl group, phenethyl group and naphthylmethyl group, phenyl group, Aryl groups such as naphthyl group, anthryl group, pyrenyl group, fluorenyl group and carbazolyl group, heterocyclic groups such as pyridyl group, thienyl group, quinolyl group and furyl group, alkoxy groups such as methoxy group, ethoxy group and propoxy group, phenoxy And aryloxy groups such as naphthoxy group, halogen atoms such as fluorine, chlorine, bromine and iodine, nitro group, cyano group and hydroxyl group.

In the present invention, the content ratio of the fluorene compound represented by the formula (1) and the stilbene compound represented by the formula (3) in the photosensitive layer is represented by a weight ratio of the compound of the formula (1): The compound of 3) is preferably from 9: 1 to 1: 9, and particularly preferably from 9: 1 to 3: 2.

In the present invention, R in formula (1)
It is preferred that ₄ and R ₉ are diarylamino groups.

Preferred examples of the compounds represented by formulas (1) and (3) are shown below, but the invention is not limited to these compounds.

Examples of the fluorene compound represented by the formula (1)

[0027]

[Outside 10]

[0028]

[Outside 11]

[0029]

[Outside 12]

[0030]

[Outside 13]

[0031]

[Outside 14]

[0032]

[Outside 15]

[0033]

[Outside 16]

[0034]

[Outside 17]

[0035]

[Outside 18]

[0036]

[Outside 19]

[0037]

[Outside 20]

[0038]

[Outside 21]

[0039]

[Outside 22]

[0040]

[Outside 23]

[0041]

[Outside 24]

[0042]

[Outside 25]

[0043]

[Outside 26]

[0044]

[Outside 27]

[0045]

[Outside 28]

[0046]

[Outside 29]

[0047]

[Outside 30]

[0048]

[Outside 31]

[0049]

[Outside 32]

[0050]

[Outside 33]

[0051]

[Outside 34]

[0052]

[Outside 35]

[0053]

[Outside 36]

[0054]

[Outside 37]

[0055]

[Outside 38]

Examples of the stilbene compound represented by the formula (3)

[0057]

[Outside 39]

[0058]

[Outside 40]

[0059]

[Outside 41]

[0060]

[Outside 42]

[0061]

[Outside 43]

[0062]

[Outside 44]

[0063]

[Outside 45]

[0064]

[Outside 46]

[0065]

[Outside 47]

[0066]

[Outside 48]

[0067]

[Outside 49]

Among the above compounds, the fluorene compound represented by the formula (1) can be synthesized by a method described in JP-A-62-208054. Also,
The stilbene compound represented by the formula (3) is disclosed in
It can be synthesized by a method described in, for example, JP-A-225660.

The structure of the photosensitive layer of the electrophotographic photosensitive member of the present invention includes, for example, the following forms. (1) layer containing charge generating material / layer containing charge transporting material (lower / upper layer) (2) layer containing charge transporting material / layer containing charge generating material (lower / upper layer) (3) charge Layer containing generator and charge transport material

Since both the fluorene compound represented by the formula (1) and the stilbene compound represented by the formula (3) have a high transporting ability to holes, they are used as the charge transporting substance in the photosensitive layer of the above-described embodiment. Can be. When the form of the photosensitive layer is (1), the polarity of the primary charge is negative, (2)
In the case of (3), it is preferably positive, and in the case of (3), it may be either positive or negative.

In the present invention, the above configurations (1) to (1)
Among (3), the form of (1) is particularly preferable, and will be described in more detail below.

The support in the present invention may be any one as long as it has conductivity, and examples thereof include the following. (1) Plates or drums made of metals or alloys such as aluminum, stainless steel and copper. (2) Aluminum, palladium, etc. on a non-conductive support such as glass, resin and paper or the conductive support of the above (1).
A thin film formed by depositing or laminating metals or alloys such as rhodium, gold and platinum. (3) A layer containing a conductive polymer, a conductive compound such as tin oxide and indium oxide is deposited or coated on a non-conductive support such as glass, resin and paper or the conductive support of (1). What was formed by doing.

Examples of the charge generating substance that can be used in the present invention include the following substances. These charge generating substances may be used alone or in combination of two or more. (1) Azo pigments such as monoazo, bisazo and trisazo (2) Phthalocyanine pigments such as metal phthalocyanine and nonmetal phthalocyanine (3) Indigo pigments such as indigo and thioindigo (4) Perylene anhydride and perylene imide (5) Polycyclic quinone pigments such as anthraquinone and pyrenequinone (6) Squarylium dyes (7) Pyrilium salts and thiopyrylium salts (8) Triphenylmethane dyes (9) Selenium and amorphous silicon Inorganic substances

The layer containing the charge-generating substance, that is, the charge-generating layer, can be formed by applying a solution in which the above-described charge-generating substance is dispersed in an appropriate binder resin onto a support. Also, vapor deposition, sputtering or C
It can also be formed by forming a thin film by a dry method such as VD.

The binder resin can be selected from a wide range of resins, for example, polycarbonate resin, polyester resin, polyarylate resin, butyral resin, polystyrene resin, polyvinyl acetal resin, diallyl phthalate resin, acrylic resin, methacrylic resin, and acetic acid. Vinyl resin, phenolic resin, silicone resin, polysulfone resin, styrene-butadiene copolymer resin, alkyd resin, epoxy resin, urea resin, vinyl chloride vinyl acetate copolymer resin and the like, but are not limited to these Absent. These may be used alone, or two or more of them may be used as a mixture or a copolymer.

The ratio of the binder resin in the charge generation layer is preferably 80% by weight or less, particularly preferably 40% by weight or less, based on the total weight of the layer. Further, the thickness of the charge generation layer is preferably 5 μm or less, particularly preferably 0.01 to 2 μm.

Various sensitizers may be added to the charge generation layer.

The layer containing the charge transporting material, that is, the charge transporting layer, comprises a fluorene compound represented by the formula (1) and a compound represented by the formula (3)
And a suitable binder resin. Examples of the binder resin used for the charge transport layer include photoconductive polymers such as polyvinyl carbazole and polyvinyl anthracene in addition to those used for the charge generation layer.

The compounding ratio of the binder resin to the compound of the present invention is preferably 10 to 500 parts by weight per 100 parts by weight of the binder resin.

The charge transport layer is electrically connected to the above-described charge generation layer, and has a function of receiving charge carriers injected from the charge generation layer in the presence of an electric field and transporting these charge carriers. doing. Since the charge transport layer has a limited ability to transport charge carriers, it cannot be unnecessarily thick.
It is preferably 40 μm, especially 10 to 30 μm
It is preferred that

Further, an antioxidant, an ultraviolet absorber, plasticity and another charge transporting substance can be added to the charge transporting layer as required.

When the photosensitive layer is a single layer, the photosensitive layer can be formed by applying a solution obtained by dissolving and dispersing the compound of the present invention and the above-mentioned charge generating substance in the above resin on a support. The film thickness is preferably from 5 to 40 μm, and particularly preferably from 10 to 30 μm.

In the present invention, an undercoat layer may be formed between the support and the photosensitive layer in order to improve the adhesion and prevent the carrier from being injected from the support.

Examples of the method for applying the various layers include a dip coating method, a spray coating method, a spinner coating method, a roller coating method, a Meyer bar coating method and a blade coating method.

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

FIG. 1 shows a schematic configuration of an electrophotographic apparatus having a process cartridge having the electrophotographic photosensitive member of the present invention.

In FIG. 1, reference numeral 1 denotes a drum-shaped electrophotographic photosensitive member of the present invention, which is driven to rotate around an axis 2 in a direction indicated by 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 above-described process is transferred to a transfer material 7 fed 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. The image is sequentially transferred by the transfer unit 6.

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

After the transfer of the image, the surface of the photoreceptor 1 is cleaned by removing the untransferred toner by the cleaning means 9, and the pre-exposure light 10 from the pre-exposure means (not shown).
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, among the above-mentioned components such as the electrophotographic photosensitive member 1, the primary charging means 3, the developing means 5 and the cleaning means 9, a plurality of components are integrally connected as a process cartridge. The process cartridge may be configured to be detachable from an electrophotographic photosensitive member such as a copying machine or a laser beam printer.

For example, at least one of the primary charging means 3, the developing means 5 and the cleaning means 9 is integrally supported together with the photoreceptor 1 to form a cartridge, and the cartridge is mounted on the apparatus main body using guide means such as the rail 12 of the apparatus main body. The process cartridge 11 can be detachably attached.

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

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

[0095]

【Example】

(Example 1) A coating solution was prepared by adding 4 g of a bisazo pigment represented by the following formula to a solution of 2 g of butyral resin (butyralization degree: 68 mol%) dissolved in 100 ml of cyclohexanone, and dispersed with a sand mill for 24 hours.

[0096]

[Outside 50]

This coating solution was applied onto an aluminum sheet,
By applying with a Meyer bar and drying, a charge generation layer having a thickness of 0.22 μm was produced.

Next, as the charge transporting substance, the above-mentioned Compound No. (1) -127 g, (3) -53 g and 10 g of bisphenol Z-type polycarbonate resin (weight average molecular weight 25,000) were dissolved in 70 g of monochlorobenzene, and this solution was applied to the previous charge generating layer with a Meyer bar. By applying and drying, a charge transport layer having a thickness of 22 μm was formed.

The obtained electrophotographic photosensitive member was corona-charged at −5 kV in a static manner using an electrostatic copying paper tester Model SP-428 manufactured by Kawaguchi Electric Co., Ltd., and was held for 1 second in a dark place. The charging characteristics were examined by exposing with 20 Lux halogen light.

As the charging characteristics, the exposure amount (E _1/5 ) required to attenuate the surface potential (V ₀ ) immediately after charging and the surface potential (V ₁ ) after dark decay for 1 second to 1/5 was obtained. ), That is, the sensitivity was measured.

Further, in order to measure the fluctuation of the light portion potential and the dark portion potential when repeatedly used, the above electrophotographic photosensitive member was attached to a photosensitive member cylinder of a PPC copier NP-3825 manufactured by Canon Inc. 2,000 sheets are copied at 23 ° C. and 50% RH, and the variation ΔV _L of the light part potential (V _L ) and the dark part potential (V _L ) between the initial and after 2,000 sheets are copied.
The variation ΔV _D of _D ) was measured. Note that ΔV _D and ΔV _L
A positive value indicates that the absolute value of the potential has increased,
A negative value indicates that the absolute value of the potential has decreased. The initial V _D and V _L are −700 V and −20, respectively.
It was set to be 0V.

Further, the electrophotographic photosensitive member was heated at 30 ° C. and 80% R
After leaving overnight under H, the same environment as above, 1,0
Performed 00 sheet copying were measured initial and 'variation [Delta] V _D and of dark portion potential (V _D)' variation [Delta] V _L of the light portion potential after 1,000 sheet copying (V _L).

Further, as a test for accelerating the cracking of the photosensitive layer, a resin was adhered to the surface of the electrophotographic photosensitive member and allowed to stand at room temperature and normal pressure for 8 hours to observe whether or not cracks had occurred in the photosensitive layer.

As a test for accelerating the crystallization of the charge transport material, a resin was adhered to the surface of the electrophotographic photosensitive member.
It was left at 0 ° C. for one week, and it was observed whether or not crystallization of the charge transporting material occurred.

Observation of cracks and crystallization was performed with a microscope (V
ERSAMET 6390 (manufactured by UNION) at a magnification of 50 times, and was evaluated as ○ when cracks and crystallization were not observed at all, and as × when even slight was observed.

(Examples 2 to 13 and Comparative Examples 1 to 10) An electrophotographic photosensitive member was prepared in the same manner as in Example 1 except that the compounds shown in the following Tables 1 and 2 were used as charge transporting substances. Created and evaluated.

The results of Examples 1 to 13 are shown in Table 1, and the results of Comparative Examples 1 to 10 are shown in Table 2.

The structures of Comparative Compounds (A) to (D) used in Comparative Examples are shown below.

[0109]

[Outside 51]

[0110]

[Table 1]

[0111]

[Table 2]

[0112]

[Table 3]

[0113]

[Table 4]

(Example 14) On an aluminum sheet,
A solution prepared by dissolving 5 g of N-methoxymethylated 6 nylon resin (weight average molecular weight 30,000) and 10 g of alcohol-soluble copolymerized nylon resin (weight average molecular weight 30,000) in 80 g of methanol is applied with a Meyer bar and dried. Thus, an undercoat layer having a thickness of 1 μm was formed.

Next, 5 g of oxytitanium phthalosinin
Was added to a solution of 4 g of a phenoxy resin dissolved in 160 g of cyclohexanone, and dispersed in a ball mill for 70 hours. This dispersion was applied onto the undercoat layer by a blade coating method and dried to form a charge generation layer having a thickness of 0.2 μm.

Next, the exemplified compound No. (1) -33
8g and No. (3) -48 2 g of bisphenol Z
Type polycarbonate resin (weight average molecular weight 35,000)
0) 13 g was dissolved in 70 g of monochlorobenzene, and the solution was coated on the charge generation layer by blade coating.
By drying, a charge transport layer having a thickness of 17 μm was formed.

V ₀ , V ₁ and sensitivity of the obtained electrophotographic photosensitive member were measured in the same manner as in Example 1. The sensitivity is V
Exposure amount (E _1/6 ) required to attenuate ₁ to 1/6 is used. As a light source, a ternary semiconductor laser of gallium / aluminum / arsenic (output: 5 mW; oscillation wavelength: 780)
nm).

Next, the electrophotographic photosensitive member was heated at 15 ° C. for 10 seconds.
After leaving overnight at% RH, it was attached to a cylinder for a photoreceptor of a laser beam printer LBP-EX manufactured by Canon, and the following evaluation was performed under the same environment.

First, a cartridge from which the developing unit and the cleaner have been removed is prepared, the entire surface is exposed corresponding to the printing of five A4 sheets, the surface potential of the fifth sheet is set to _VL, and then the primary charging is stopped while the laser is irradiated. The surface potential at the rotation was defined as residual potential _Vr .

Next, a 1,000-sheet running durability test was performed, and the light portion potential V _L 'and the residual potential V _r ' immediately after the running were measured by the same method as described above. The variation amount ΔV _L = | V _L −V _L '| and ΔV _r = |
V _r −V _r ′ |

The same method as in Example 1 was used to evaluate the cracks in the photosensitive layer and the crystallization of the charge transporting substance.

The results are shown in Table 3.

(Examples 15 to 20 and Comparative Examples 11 to 1)
6) An electrophotographic photosensitive member was prepared and evaluated in the same manner as in Example 14 except that the compounds shown in Table 3 below were used as the charge transporting substance.

Table 3 shows the results.

The structures of Comparative Compounds (E) to (G) used in Comparative Examples are shown below.

[0126]

[Outside 52]

[0127]

[Table 5]

[0128]

As described above, according to the present invention, an electrophotographic photoreceptor having excellent electrophotographic properties, durability and environmental stability and hardly causing cracks and crystallization, Process cartridge and an electrophotographic apparatus having the same.

[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.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Tetsuro Kanamaru 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside Canon Inc. (72) Inventor Koichi Nakata 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside the corporation

Claims (6)

[Claims] 1. An electrophotographic photosensitive member having a photosensitive layer on a support, wherein the photosensitive layer has the following formula (1). (Wherein R ₁ and R ₂ are the same or different and each is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a ring group formed by bonding to each other, Represents a hydrogen atom;
_{3 to} R ₁₀ may be the same or different and each may be a substituted or unsubstituted diarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a halogen atom, a nitro group and a hydrogen atom; Represents an atom, and at least two of R _{3 to} R ₁₀ represent a substituted or unsubstituted diarylamino group. ) And a fluorene compound represented by the following formula (3): (Wherein, Ar ₃ and Ar ₄ are the same or different and represent a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group, and Ar ₅ is a substituted or unsubstituted arylene group and a substituted or unsubstituted R ₁₁ and R ₁₂ represent the same or different and represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a hydrogen atom. , N represents 1 or 2, and when n is 1, R ₁₁ and R
₁₂ may combine with each other to form a ring. An electrophotographic photosensitive member comprising a stilbene compound represented by the formula (1): 2. The electrophotographic photosensitive member according to claim 1, wherein the photosensitive layer is a surface layer. 3. A photosensitive layer having a charge generation layer and a charge transport layer, wherein the charge transport layer is a surface layer containing a fluorene compound represented by the formula (1) and a triarylamine represented by the formula (3). The electrophotographic photoreceptor according to claim 2. 4. The substituent which the diarylamino group of R _{3 to} R ₁₀ in the formula (1) may have is an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a halogen. 4. The electrophotographic photoreceptor according to claim 1, which is at least one group selected from the group consisting of an atom, a nitro group, a cyano group and a hydroxyl group. 5. A process cartridge which integrally supports at least one means selected from the group consisting of an electrophotographic photoreceptor, a charging means, a developing means and a cleaning means and is detachable from an electrophotographic apparatus main body. The photographic photoreceptor has a photosensitive layer on a support, and the photosensitive layer has the following formula (1). (Wherein R ₁ and R ₂ are the same or different and each is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a ring group formed by bonding to each other, Represents a hydrogen atom;
_{3 to} R ₁₀ may be the same or different and each may be a substituted or unsubstituted diarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a halogen atom, a nitro group and a hydrogen atom; Represents an atom, and at least two of R _{3 to} R ₁₀ represent a substituted or unsubstituted diarylamino group. ) And a fluorene compound represented by the following formula (3): (Wherein, Ar ₃ and Ar ₄ are the same or different and represent a substituted or unsubstituted aryl group and a substituted or unsubstituted hetero group, and Ar ₅ is a substituted or unsubstituted arylene group and a substituted or unsubstituted hetero group. And R ₁₁ and R ₁₂ are the same or different and represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a hydrogen atom. , N represents 1 or 2, and when n is 1, R ₁₁ and R ₁₂
May combine with each other to form a ring. A process cartridge comprising a stilbene compound represented by the formula (1): 6. An electrophotographic photoreceptor, charging means, exposure means,
In an electrophotographic apparatus having a developing unit and a transfer unit, the electrophotographic photosensitive member has a photosensitive layer on a support, and the photosensitive layer has the following formula (1). (Wherein R ₁ and R ₂ are the same or different and each is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a ring group formed by bonding to each other, Represents a hydrogen atom;
_{3 to} R ₁₀ may be the same or different and each may be a substituted or unsubstituted diarylamino group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a halogen atom, a nitro group and a hydrogen atom; Represents an atom, and at least two of R _{3 to} R ₁₀ represent a substituted or unsubstituted diarylamino group. ) And a fluorene compound represented by the following formula (3): (Wherein, Ar ₃ and Ar ₄ are the same or different and represent a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group, and Ar ₅ is a substituted or unsubstituted arylene group and a substituted or unsubstituted R ₁₁ and R ₁₂ are the same or different and represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, and a hydrogen atom. , N represents 1 or 2, and when n is 1, R ₁₁ and R ₁₂
May combine with each other to form a ring. An electrophotographic apparatus comprising a stilbene compound represented by the following formula: