JP2002229228A - Electrophotographic photoreceptor, process cartridge and electrophotographic device having the electrophotographic photoreceptor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an electrophotographic photoreceptor which can form images with no image defects while keeping high sensitivity, in particular, while keeping high sensitivity characteristics in the wavelength region of a semiconductor laser. SOLUTION: The photosensitive layer of the electrophotographic photoreceptor contains a resolcinarene compound expressed by formula (1). The process cartridge and the electrophotographic device have the above electrophotographic photoreceptor. In formula (1), R1 is hydrogen atom, an alkyl group or the like, R2 is hydrogen atom, an alkyl group, Ar-N=N- group or the like, and Ar is an aromatic hydrocarbon cyclic group, heterocyclic group or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an electrophotographic photoreceptor,
The present invention relates to a process cartridge having the electrophotographic photosensitive member and an electrophotographic apparatus.

[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, azo pigment and phthalocyanine have advantages such as non-pollution and high productivity compared to inorganic photoconductive materials, but have low sensitivity and are difficult to commercialize. Met. For this reason, several sensitization methods have been proposed, and as an effective method, use of a function-separated type photoconductor in which a charge generation layer and a charge transport layer are laminated has become mainstream, and as a practical method, It has become.

On the other hand, in recent years, non-impact printers to which electrophotographic technology has been applied have been widely used in place of conventional impact-type printers as terminal printers. These are mainly laser beam printers using laser light as a light source, and a semiconductor laser is used as the light source in terms of cost, size of the apparatus, and the like.

At present, mainly used semiconductor lasers have a long oscillation wavelength of 650 to 820 nm, and therefore, development of an electrophotographic photosensitive member having sufficient sensitivity to such long wavelength light has been promoted.

Azo pigments and phthalocyanine pigments are extremely effective as charge generation materials having sensitivity up to such a long wavelength region.
1962 and JP-A-1-183663, as phthalocyanines, oxytitanium phthalocyanine and gallium phthalocyanine have excellent sensitivity characteristics as compared with conventional phthalocyanine compounds, and until now, JP-A-61-239248, JP-A-61-217050, JP-A-62-67094 and JP-A-63-218768.
JP-A-6-17066, JP-A-5-098
Nos. 181 and 5-263007 and 10-6
Various crystal forms are disclosed in, for example, JP-A-7946.
Further, JP-A-7-128888 and JP-A-9-34
No. 149 discloses a combination with a specific azo compound in order to improve the problem of the phthalocyanine compound. However, a photoreceptor that provides an image free from image defects while maintaining higher sensitivity characteristics is desired. I was

[0006]

The electrophotographic photoreceptor using an azo compound and a phthalocyanine has such excellent sensitivity characteristics, but the generated photocarriers are liable to remain in the photosensitive layer. There is a drawback that a potential change easily occurs as a memory.

Although not confirmed in principle, the electrons left in the charge generation layer may be, for some reason, at the interface between the charge generation layer and the charge transport layer, or between the charge generation layer and the undercoat layer or the undercoat layer. It is thought that it migrates to the interface with the conductive layer and raises or lowers the barrier property of hole injection near the interface.

A phenomenon that appears when an electrophotographic photosensitive member is actually used is that when electrons stay at the interface between the charge transport layer and the charge generation layer, they appear as a decrease in the light portion potential or residual potential during continuous printing. For example, when used in a development process (a so-called reversal development system) in which a dark portion potential portion and a light portion potential portion, which are often used in printers at present, are used as a non-development portion, a sensitivity at a location irradiated with light at the time of pre-printing is used. If a full white image is taken at the time of the next print, the so-called ghost phenomenon (hereinafter abbreviated as positive ghost) in which the previous print portion becomes black appears.

When electrons remain at the interface between the charge generation layer and the undercoat layer or between the undercoat layer and the conductive layer, the increase appears in the bright portion potential during printing. When used in a reversal development system, the sensitivity at the place where light hits during the previous print becomes slow, and when taking a full black image at the next print, the so-called ghost phenomenon (hereinafter abbreviated as “negative ghost”) where the previous print part appears white. Appears noticeably.

Of these phenomena, a negative ghost often appears at the beginning of printing, and a positive ghost often appears during continuous printing. This phenomenon is particularly remarkable in a photoreceptor using an undercoat layer as an adhesive layer of the charge generation layer, and the volume resistance of the charge generation layer and the undercoat layer to electrons increases in an environment such as low temperature and low humidity. There is a drawback that electrons easily fill the charge generation layer and a ghost phenomenon easily occurs.

Accordingly, an object of the present invention is to provide an electrophotographic photosensitive member for supplying an image free from image defects while maintaining high sensitivity, particularly high sensitivity characteristics in a semiconductor laser wavelength region, a process cartridge having the electrophotographic photosensitive member, and a process cartridge having the same. An object of the present invention is to provide an electrophotographic apparatus.

[0012]

According to the present invention, there is provided an electrophotographic photoreceptor having a photosensitive layer on a conductive support, wherein the photosensitive layer contains a resorcinarene compound represented by the following general formula (1). Characteristic electrophotographic photoreceptor. General formula (1)

[0013]

Embedded image Wherein, R ₁ represents a hydrogen atom, which may have a an optionally substituted alkyl group or an optionally substituted aryl group, R ₂
Represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent or an Ar-N = N- group, and Ar represents an aromatic hydrocarbon which may have a substituent. Ring group,
A heterocyclic group which may have a substituent, a group to which a plurality of aromatic hydrocarbon rings are bonded, or a group to which a plurality of heterocycles are bonded is shown.

Further, according to the present invention, the electrophotographic photosensitive member and at least one means selected from the group consisting of a charging means, a developing means and a cleaning means are integrally supported, and are detachably mountable to an electrophotographic apparatus main body. Is a process cartridge characterized by the above-mentioned.

Further, the present invention is an electrophotographic apparatus comprising the above electrophotographic photosensitive member, charging means, image exposure means, developing means and transfer means.

[0016]

BEST MODE FOR CARRYING OUT THE INVENTION The resorcinarene compound used in the present invention is represented by the following general formula (1). General formula (1)

[0017]

Embedded image Wherein, R ₁ represents a hydrogen atom, which may have a an optionally substituted alkyl group or an optionally substituted aryl group, R ₂
Represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent or an Ar-N = N- group, and Ar represents an aromatic hydrocarbon which may have a substituent. Ring group,
A heterocyclic group which may have a substituent, a group to which a plurality of aromatic hydrocarbon rings are bonded, or a group to which a plurality of heterocycles are bonded is shown.

The alkyl group in the above expression includes groups such as methyl, ethyl, propyl, hexyl, undecyl and tridecyl, the aryl group includes groups such as phenyl and naphthyl, and the aromatic hydrocarbon ring includes benzene. , Naphthalene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene and the like, and the heterocycle is furan, thiophene, pyridine, indole, benzothiazole, carbazole, benzocarbazole, acridone, dibenzothiophene,
Benzoxazole, benzotriazole, oxathiazole, thiazole, phenazine, cinnoline and benzocinnoline, and the like, and further, those in which a plurality of aromatic hydrocarbon rings or a plurality of heterocycles are bonded,
Triphenylamine, diphenylamine, N-methyldiphenylamine, biphenyl, terphenyl, binaphthyl, fluorenone, phenanthrenequinone, anthraquinone, benzanthrone, diphenyloxazole, phenylbenzoxazole, diphenylmethane, diphenylsulfone, diphenylether, benzophenone,
Stilbene, distyrylbenzene, tetraphenyl-p
-Phenylenediamine and tetraphenylbenzidine.

The substituents in the above expression include alkyl groups such as methyl, ethyl, propyl and butyl, phenyl,
Aryl groups such as biphenyl and naphthyl; alkoxy groups such as methoxy and ethoxy; alkylamino groups such as dimethylamino and diethylamino; arylamino groups such as phenylamino and diphenylamino; halogen atoms such as fluorine, chlorine, bromine and iodine; Groups, nitro groups, cyano groups, halomethyl groups such as trifluoromethyl and the like.

Next, examples of the resorcinarene compound used in the present invention are shown below, but the present invention is not limited to these.

Basic skeleton

[0022]

Embedded image

[0023]

[Table 1]

[0024]

[Table 2]

The resorcinarene compound represented by the general formula (1) is a known example (for example, J. Am. Chem. Soc., Vol. 111, No.
14,1989 p 5397-5404), and can be synthesized by dehydrating and condensing a resorcinol derivative and various aldehyde compounds with an acid such as sulfuric acid and hydrochloric acid. Furthermore,
Method for introducing the azo group in R ₂ may, R ₂ can be synthesized by azo reduction coupling reaction with Rezorushinaren compound and a diazo compound derivative of hydrogen (Reference Example: CHEMISTRY LETTER
S, pp. 1219-1222, 1990).

Hereinafter, "%" and "part" mean "% by mass" and "part by mass", respectively.

Synthesis Example 1 <Synthesis of Exemplified Compound 15> Under an atmosphere of nitrogen, 25.6 parts of resorcinol, 42.3 parts of dodecyl aldehyde, and 230 parts of ethanol were added to an eggplant flask equipped with a condenser, and concentrated hydrochloric acid 37 was added thereto. The mixture was treated at 70 ° C. for 10 hours, cooled, collected, washed sufficiently with hot water, dried, and recrystallized with methanol to give white crystalline Compound 15. Three copies were obtained.

The following shows 1H-NMR and IR data of the obtained compound.

1N-NMR (CDCL3, 40 ° C.) δ 0.91 (t, 12H), 1.30 (brs, 64)
H), 1.41 (brs, 8H), 2.24 (brs,
8H), 4.33 (t, 4H), 6.15 (s, 4
H), 7.24 (s, 4H), 9.27, 9.37,
9.55, 9.62 (eachbrs, 4H) IR (KBr) 3548, 3492, 2924, 28
52, 1618, 1508, 1465, 1432, 13
02, 1196, 1167, 903, 837 cm ^-1

Synthesis Example 2 <Synthesis of Exemplified Compound 1> In a nitrogen atmosphere, 4.4 parts of Exemplified Compound 15 was added to DMF36.
After cooling the solution dissolved in 0 parts to 0 ° C., the following compound

[0031]

Embedded image 5.6 parts and 60 parts of pyridine are added, and
After stirring for an hour, the mixture was poured into 1500 parts of water, and the precipitate was collected by filtration. The obtained crystals are sufficiently washed with 2% hydrochloric acid and then with water,
After drying, the crystals were recrystallized from tetrahydrofuran to obtain 5 parts of Exemplified Compound 1 as red crystals.

The IR data of the obtained compound are shown below.

IR (KBr) 3101, 2925, 1
542, 1491, 1342 cm ^-1

As the azo pigment used as the charge generating material in the present invention, any azo pigment such as bisazo, trisazo and tetrakisazo can be used. Among them, JP-A-59-31962 and JP-A-1-18-18 are particularly preferable.
The benzanthrone-based azo pigment disclosed in JP-A-3663 has excellent sensitivity characteristics and is preferred.

As the phthalocyanine pigment, any phthalocyanine such as metal-free phthalocyanine and metal phthalocyanine which may have an axial ligand can be used and may have a substituent. Particularly, oxytitanium phthalocyanine and gallium Phthalocyanines are preferred.
Further, any crystal form may be used.
7.4 ° ± 0.2 of Bragg angle 2θ in characteristic X-ray diffraction.
Hydroxygallium phthalocyanine in crystalline form having strong peaks at 2 ° and 28.2 ° ± 0.2 °, 7.4 with a Bragg angle of 2θ ± 0.2 ° in CuKα characteristic X-ray diffraction
Chlorogallium phthalocyanine in crystalline form with strong peaks at °, 16.6 °, 25.5 ° and 28.3 °, C
27.2 of Bragg angle 2θ in uKα characteristic X-ray diffraction
Crystalline oxytitanium phthalocyanine having a strong peak at ° ± 0.2 ° is preferred because it has excellent sensitivity characteristics. Furthermore, hydroxygallium phthalocyanine in a crystalline form having strong peaks at Bragg angles 2θ of 7.4 ° ± 0.2 ° and 28.2 ° ± 0.2 ° in CuKα characteristic X-ray diffraction, and CuKα characteristic X-ray diffraction Bragg angle 2
Crystalline oxytitanium phthalocyanine having a strong peak at θ of 27.2 ° ± 0.2 ° is preferred. Also,
Among them, in particular, 7.3 °, 24.9 ° and 28.25 of Bragg angles 2θ ± 0.2 ° in CuKα characteristic X-ray diffraction.
Crystalline hydroxygallium phthalocyanine having a strong peak at 1 °, 7.5 °, 9.9 °, 16.3 with Bragg angle 2θ ± 0.2 ° in CuKα characteristic X-ray diffraction
Crystalline forms of hydroxygallium phthalocyanine having strong peaks at °, 18.6 °, 25.1 ° and 28.3 °, Bragg angle 2θ ± in CuKα characteristic X-ray diffraction
9.0 °, 14.2 °, 23.9 ° and 2 of 0.2 °
Crystalline form of oxytitanium phthalocyanine having a strong peak at 7.1 °, 9.5 °, 9.7 °, 11.7 at Bragg angle 2θ ± 0.2 ° in CuKα characteristic X-ray diffraction
°, 15.0 °, 23.5 °, 24.1 ° and 27.3
Oxytitanium phthalocyanine in a crystalline form having a strong peak at ° is preferred.

The layer constitution of the electrophotographic photoreceptor in the present invention is such that a photosensitive layer consisting of a single layer simultaneously containing a resorcinarene compound represented by the general formula (1), a charge generating material and a charge transporting material is formed on a conductive support. And a photosensitive layer in which a charge generation layer containing a resorcinarene compound and a charge generation material and a charge transport layer containing a charge transport material are laminated on a conductive support. The stacking relationship between the charge generation layer and the charge transport layer may be reversed.

The conductive support may be any material having conductivity, such as metal such as aluminum and stainless steel, or metal provided with a conductive layer, plastic, and paper. And the like.

An undercoat layer having a barrier function and an adhesive function may be provided between the conductive support and the photosensitive layer. Polyvinyl alcohol, polyethylene oxide, ethyl cellulose, methyl cellulose,
Casein, polyamide, glue and gelatin are used. These are dissolved in a suitable solvent and applied on a conductive support. The thickness is preferably from 0.2 to 3.0 μm.

Further, it is preferable to provide a conductive layer between the support and the undercoat layer for the purpose of covering unevenness or defects of the support or preventing interference fringes. This can be formed by dispersing conductive powder such as carbon black, metal particles and metal oxide in a binder resin. The thickness of the conductive layer is preferably 5 to 40 μm,
More preferably, it is 30 μm.

When a photosensitive layer consisting of a single layer is formed, a resorcinalane compound, a charge generating material and a charge transporting material are mixed in an appropriate binder resin solution, and the mixture is applied on a conductive support and dried. Formed.

When forming a photosensitive layer having a laminated structure,
The charge generation layer may be formed by dispersing a resorcinarene compound and a charge generation material together with a suitable binder resin solution, applying the dispersion, and drying the dispersion.

The charge transport layer is formed by applying a coating material in which a charge transport material and a binder resin are dissolved in a solvent and then drying the coating. Examples of the charge transport material include various triarylamine compounds, hydrazone compounds, stilbene compounds, pyrazoline compounds, oxazole compounds, thiazole compounds, and triallylmethane compounds.

Examples of the binder resin used for each layer include polyester, acrylic resin, polyvinyl carbazole, phenoxy resin, polycarbonate, polyvinyl butyral, polystyrene, polyvinyl acetate, polysulfone, polyarylate, vinylidene chloride, acrylonitrile copolymer, and polyvinyl benzal. Is mentioned.

Examples of the method for applying the photosensitive layer include dipping, spray coating, spinner coating, bead coating, blade coating, and beam coating.

When the photosensitive layer is a single layer, the thickness is 5 to 40 μm.
m, more preferably 10 to 30 μm. In the case of a laminated structure, the thickness of the charge generation layer is preferably 0.05 to 10 μm, and 0.1 to 5 μm.
μm, and the thickness of the charge transport layer is 5 μm.
It is preferably from 40 to 40 μm, and more preferably from 10 to 30 μm.

In the case of a laminated structure, the content of the resorcinarene compound is preferably from 0.01 to 10% by mass, more preferably from 0.1 to 5% by mass, based on the charge generation layer. The content of the charge generation material is preferably from 30 to 90% by mass, and more preferably from 50 to 80% by mass of the charge generation layer.
More preferably, it is mass%. The content of the charge transport material is preferably from 20 to 80% by mass, more preferably from 30 to 70% by mass, based on the charge transport layer.

When the photosensitive layer is a single layer, the content of the resorcinarene compound is preferably 0.01 to 5% by mass based on the photosensitive layer. The content of the charge generation material is preferably 3 to 30% by mass based on the photosensitive layer. The content of the charge transport layer is preferably from 30 to 70% by mass based on the photosensitive layer.

A protective layer may be provided on the photosensitive layer if necessary. The protective layer is made of a resin such as polyvinyl butyral, polyester, polycarbonate (such as polycarbonate Z and modified polycarbonate), polyamide, polyimide, polyarylate, polyurethane, styrene-butadiene copolymer, styrene-acrylic acid copolymer and styrene-acrylonitrile copolymer. By dissolving, coating on the photosensitive layer and drying. The thickness of the protective layer is preferably 0.05 to 20 μm. Further, the protective layer may contain conductive particles, an ultraviolet absorber, and the like. As the conductive particles, for example, metal oxides such as tin oxide particles are preferable.

Next, an electrophotographic apparatus using the electrophotographic photosensitive member of the present invention will be described.

In FIG. 1, reference numeral 1 denotes a drum type electrophotographic photosensitive member of the present invention, which is driven to rotate around an axis 1a in a direction indicated by an arrow at a predetermined peripheral speed. The photoreceptor 1 is uniformly charged at a predetermined positive or negative potential on its peripheral surface by a charging means 2 during the rotation process, and then the image exposure L (slit exposure or 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 a developing unit 4, and the toner image is transferred by a corona transfer unit 5 from a feeding unit (not shown) to the photosensitive member 1.
The recording material 9 is sequentially transferred onto the surface of the fed recording material 9 in synchronization with the rotation of the photosensitive member 1 between the recording medium 9 and the transfer means 5. The recording material 9 to which the image has been transferred is separated from the photosensitive member surface and
And the image is fixed and printed out of the machine as a copy. The surface of the photoreceptor 1 after the image transfer is cleaned and cleaned by the removal of the untransferred toner by the cleaning means 6, subjected to the charge removal treatment by the pre-exposure means 7, and used repeatedly for image formation.

In the apparatus shown in FIG. 2, at least the photosensitive member 1, the charging means 2 and the developing means 4 are housed in a container 20 to form a process cartridge, and the process cartridge is formed by using a guide means 12 such as a rail of the present invention. It is configured to be removable. The cleaning means 6 may or may not be disposed in the container 20.

As shown in FIGS. 3 and 4, the contact charging member 10 is used as charging means, and the contact charging member 10 to which voltage is applied is brought into contact with the photosensitive member 1 to charge the photosensitive member 1. (This charging method is hereinafter referred to as contact charging). 3 and 4, the toner image on the photoconductor 1 is also transferred to the recording material 9 by the contact charging member 23. That is, the toner image on the photoconductor 1 is transferred to the recording material 9 by bringing the contact charging member 23 to which the voltage is applied into contact with the recording material 9.

Further, in the apparatus shown in FIG. 4, at least the photosensitive member 1 and the contact charging member 10 are housed in a first container 21 to form a first process cartridge, and at least the developing means 4 is housed in a second container 22. The first process cartridge and the second process cartridge are detachably configured as a second process cartridge. The cleaning means 6 may or may not be disposed in the container 21.

When the electrophotographic apparatus is used as a copier or a printer, the image exposure L uses reflected light or transmitted light from the original, or scans the original with a laser beam according to the read signal. The driving is performed by driving a light emitting diode array or a liquid crystal shutter array.

[0055]

EXAMPLES Example 1 50 parts of titanium oxide powder coated with tin oxide containing 10% antimony oxide, 25 parts of resole type phenol resin, 20 parts of methyl cellosolve,
5 parts of methanol and silicone oil (polydimethylsiloxane polyoxyalkylene copolymer, average molecular weight 3
000) was dispersed in a sand mill using glass beads having a diameter of 1 mm for 2 hours to prepare a coating for a conductive layer.

Aluminum cylinder (φ30 mm × 2
60.5 mm), the coating material was applied by a dipping method, and dried at 140 ° C. for 30 minutes.
m conductive layers were formed.

A solution obtained by dissolving 5 parts of a 6-66-610-12 quaternary polyamide copolymer resin in a mixed solvent of 70 parts of methanol and 25 parts of butanol was applied thereon by dipping, dried and dried. An undercoat layer having a thickness of 1 μm was provided.

Next, in the CuKα characteristic X-ray diffraction, the Bragg angles 2θ ± 0.2 ° of 7.5 °, 9.9 °, 16.3 °
°, 18.6 °, 25.1 ° and 28.3 °, 10 parts of crystalline hydroxygallium phthalocyanine having strong peaks, 0.1 part of the exemplified compound (1), and a polyvinyl butyral resin (trade name: Eslek BX) -1; Sekisui Chemical Co., Ltd.) (5 parts) was added to 250 parts of cyclohexanone, and 1 part was added by a sand mill using glass beads having a diameter of 1 mm.
The mixture was dispersed over time, diluted with 250 parts of ethyl acetate, applied to the undercoat layer, and dried at 100 ° C. for 10 minutes to form a charge generation layer having a thickness of 0.16 μm. .

Next, the following structural formula

[0060]

Embedded image Is prepared by dissolving 10 parts of a charge transport material represented by the following formula and 10 parts of a polycarbonate resin (trade name: Iupilon Z-200, manufactured by Mitsubishi Gas Chemical Industry Co., Ltd.) in 70 parts of monochlorobenzene, and dipping on the charge generation layer. Was applied. This was dried at 110 ° C. for 1 hour to obtain a film having a thickness of 25 μm.
m of a charge transport layer was formed, and an electrophotographic photosensitive member was prepared.

Example 2 A photoconductor of Example 2 was prepared in exactly the same manner as in Example 1 except that the amount of the exemplified compound (1) was changed to 0.5 part.

Example 3 A photoconductor of Example 3 was prepared in the same manner as in Example 1 except that the exemplified compound (1) was replaced with the exemplified compound (2).

Example 4 A photoconductor of Example 4 was prepared in the same manner as in Example 3, except that the amount of the exemplary compound (2) was changed to 0.5 part.

Example 5 A photoconductor of Example 5 was prepared in the same manner as in Example 1 except that the exemplified compound (1) was changed to the exemplified compound (3).

Example 6 A photoconductor of Example 6 was prepared in the same manner as in Example 1 except that the example compound (1) was replaced with the example compound (15).

Example 7 In the CuKα characteristic X-ray diffraction, the Bragg angles 2θ ± 0.2 ° of 7.5 °, 9.9 °, 1
Hydroxygallium phthalocyanine in a crystalline form having strong peaks at 6.3 °, 18.6 °, 25.1 ° and 28.3 ° was converted to a Bragg angle 2θ in CuKα characteristic X-ray diffraction.
9.0 °, 14.2 °, 23.9 ° and 2 of ± 0.2 °
A photoconductor of Example 7 was prepared in the same manner as Example 1, except that the crystalline form of oxytitanium phthalocyanine having a strong peak at 7.1 ° was used.

Example 8 A charge generation layer was formed in the same manner as in Example 1. Next, the following structural formula

[0068]

Embedded image A solution prepared by dissolving 10 parts of a charge transporting material represented by the following formula and 10 parts of a polycarbonate resin (trade name: Iupilon Z-400, manufactured by Mitsubishi Gas Chemical Industry Co., Ltd.) in 100 parts of monochlorobenzene is prepared and dipped on the charge generating layer. Was applied. This was dried at 150 ° C. for 30 minutes to give a film thickness of 1
An electrophotographic photoreceptor was formed by forming a 5 μm charge transport layer.

Example 9 A charge generation layer was formed in the same manner as in Example 1. Next, the following structural formula

[0070]

Embedded image 7 parts of a charge transporting material represented by the following structural formula

[0071]

Embedded image Is prepared by dissolving 3 parts of the charge transporting material represented by the following formula and 10 parts of a polycarbonate resin (trade name: Iupilon Z-200, manufactured by Mitsubishi Gas Chemical Industry Co., Ltd.) in 70 parts of monochlorobenzene, and dipping on the charge generating layer. Was applied. This is dried at 110 ° C. for 1 hour to have a thickness of 32 μm.
To form an electrophotographic photoreceptor.

Comparative Example 1 A photoconductor of Comparative Example 1 was prepared in exactly the same manner as in Example 1 except that the exemplified compound (1) was not added.

Comparative Example 2 A photoconductor of Comparative Example 2 was prepared in exactly the same manner as in Example 7 except that the exemplified compound (1) was not added.

Comparative Example 3 Bisazo pigment having the following structural formula in place of Exemplified Compound (1)

[0075]

Embedded image Comparative Example 3 was performed in exactly the same manner as in Example 7 except that 3 parts were added.
Was made.

Using these electrophotographic photosensitive members, the measurement of the light portion potential and the evaluation of the ghost image were performed. For the evaluation, a laser beam printer (trade name: Laser Jet 4000: manufactured by Hewlett Packard) was modified and used. First, after measuring the initial bright portion potential and evaluating the ghost image under the environment of a temperature of 23 ° C. and 55% RH, an endurance test of 1,000 sheets was conducted under the same environmental conditions. Was measured for the bright part potential and the ghost image was evaluated.

Next, these photoreceptors were left together with an evaluator under low temperature and low humidity (L / L) at a temperature of 15 ° C. and 10% RH for 3 days, and then a measurement of a light portion potential and evaluation of a ghost image were performed. Was.

The conditions for the paper passing durability were set to an intermittent mode for printing four sheets per minute, and a durability pattern was performed in a mode in which lines having a width of about 0.5 mm were printed every 10 mm in a vertical direction.

The ghost image evaluation method was as follows. As the ghost image, a black square pattern of 5 mm square was printed by an arbitrary number for one round of the drum, and thereafter, an entire halftone image (an image having a dot density of one dot and one space), an entire white image, or an entire black image was printed. Ghost image samples were sampled at the development volume of the machine, F5 (center value) and F9 (light density). The evaluation was made visually, and the degree of ghost was ranked as follows.

Rank 1 is "a ghost is not visible at all in any mode". Rank 2 is "a level at which a ghost is slightly visible in a specific mode". Rank 3 is "a level at which a ghost is slightly visible in any mode." The level at which ghosts can be seen even in the mode described above. "

[0081]

[Table 3]

[0082]

As described above, according to the present invention, an electrophotographic photoreceptor for supplying an image free from image defects while maintaining high sensitivity, particularly high sensitivity characteristics in a semiconductor laser wavelength range, A process cartridge having a photoreceptor and an electrophotographic apparatus are provided.

[Brief description of the drawings]

FIG. 1 is a view showing a schematic configuration of an electrophotographic apparatus having an electrophotographic photosensitive member of the present invention.

FIG. 2 is a view showing a schematic configuration of an electrophotographic apparatus having a process cartridge having an electrophotographic photosensitive member of the present invention.

FIG. 3 is a view showing a schematic configuration of an electrophotographic apparatus having a process cartridge having an electrophotographic photosensitive member of the present invention.

FIG. 4 is a view showing a schematic configuration of an electrophotographic apparatus having a process cartridge having an electrophotographic photosensitive member according to the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Electrophotographic photoreceptor 1a shaft 2 Charging means 3 Exposure unit 4 Developing means 5 Transfer means 6 Cleaning means 7 Pre-exposure means 8 Fixing means 9 Recording material 10, 23 Contact charging member 12 Guide means 20, 21, 22 Container L Image exposure

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Atsushi Fujii 3-30-2 Shimomaruko, Ota-ku, Tokyo Inside Canon Inc. (72) Inventor Ichie Hama 3-30-2 Shimomaruko, Ota-ku, Tokyo Kia Non-corporation F term (reference) 2H068 AA14 AA19 BA12 BA39 BA41

Claims (9)

[Claims] 1. An electrophotographic photosensitive member having a photosensitive layer on a conductive support, wherein the photosensitive layer contains a resorcinarene compound represented by the following general formula (1). General formula (1) Wherein, R ₁ represents a hydrogen atom, which may have a an optionally substituted alkyl group or an optionally substituted aryl group, R ₂
Represents a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent or an Ar-N = N- group, and Ar represents an aromatic hydrocarbon which may have a substituent. Ring group,
A heterocyclic group which may have a substituent, a group to which a plurality of aromatic hydrocarbon rings are bonded, or a group to which a plurality of heterocycles are bonded is shown. 2. The electrophotographic photoreceptor according to claim 1, wherein the resorcinarene compound is a compound represented by the following general formula (2). General formula (2) In the formula, R ₁ represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent;
Represents an aromatic hydrocarbon ring group which may have a substituent, a heterocyclic group which may have a substituent, a group in which a plurality of aromatic hydrocarbon rings are bonded, or a group in which a plurality of heterocycles are bonded. . 3. The electrophotographic photoreceptor according to claim 1, wherein the photosensitive layer contains a phthalocyanine pigment or an azo pigment as a charge generation material. 4. The electrophotographic photosensitive member according to claim 3, wherein said phthalocyanine pigment is oxytitanium phthalocyanine. 5. The electrophotographic photoreceptor according to claim 3, wherein said phthalocyanine pigment is gallium phthalocyanine. 6. The electrophotographic photosensitive member according to claim 5, wherein said gallium phthalocyanine pigment is hydroxygallium phthalocyanine. 7. The photosensitive layer according to claim 1, wherein the photosensitive layer has a charge generation layer and a charge transport layer, and the charge generation layer contains a resorcinarene compound represented by the general formula (1). Electrophotographic photoreceptor. 8. An electrophotographic apparatus main body, wherein the electrophotographic photosensitive member according to claim 1 and at least one unit selected from the group consisting of a charging unit, a developing unit and a cleaning unit are integrally supported. A process cartridge which is detachably attached to the cartridge. 9. An electrophotographic apparatus comprising the electrophotographic photosensitive member according to claim 1, a charging unit, an exposing unit, a developing unit, and a transferring unit.