JPH07128889A - Electrophotographic photoreceptor - Google Patents

Abstract

PURPOSE:To provide a photoreceptor excellent in photosensitivity, durability and environmental stability and having satisfactory photosensitivity over a wide range from a visible light region to a near IR region. CONSTITUTION:This photoreceptor contains a gallium phthalocyanine compd. and a perylene compd. represented by formula I or an anthanthrone compd. represented by formula II as carrier generating materials in the photosensitive layer. In the formula I, each of A1, A1', A2 and A2' is a divalent arom. hydrocarbon group or a divalent heterocyclic group contg. an N atom in the ring. In the formula II, X is halogen, nitro, cyano, acyl or carboxy and (n) is an integer of 0-4.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electrophotographic photoreceptor using a gallium phthalocyanine compound as a photoconductive material.

[0002]

BACKGROUND OF THE INVENTION Phthalocyanine compounds are materials useful as paints, printing inks, catalysts or electronic materials.
Particularly in recent years, it has been extensively studied as a material for an electrophotographic photoreceptor, an optical recording material and a photoelectric conversion material. Regarding electrophotographic photoconductors, in recent years, the photosensitivity wavelength range of conventionally proposed organic photoconductive materials has been extended to the wavelength (780 to 830 nm) of semiconductor lasers in the near infrared region, and photoconductors for digital recording such as laser printers have been developed. There is a growing demand for its use as a squarium compound, and from this point of view, the squarylium compound (Japanese Patent Application Laid-Open Nos. 49-105536 and 58-58
21416), triphenylamine-based trisazo compounds (JP-A-61-151659), phthalocyanine compounds (JP-A-48-34189 and 57).
No. 148745) has been proposed as a photoconductive material for semiconductor lasers. In particular, many compounds are known for electrophotographic photoreceptors using phthalocyanine, and x-type H2Pc (US Pat. No. 3,816,118) is known.
Specification), ClInPc (JP-A-59-44054), α-type TiOPc (JP-A-62-134651), β-type TiOPc (JP-A-63-218768), Y-type TiOPc (special JP-A No. 64-17066) and the like, and regarding gallium phthalocyanine, a photosensitive member using a specific crystal type is disclosed in JP-A 1-222.
With respect to ClGaPc, Japanese Patent Laid-Open No. 59-44053 proposes a photoreceptor to be used after vapor deposition for ClGaPc.

By the way, development of an apparatus in which a printer using a near-infrared semiconductor laser is provided with a function of a copying machine using white light is under way. In this case, the photoconductor used is required to have a wide range of visible light to near-infrared light and good photosensitivity. However, although the phthalocyanine compound has a good photosensitivity in the near infrared region, the photosensitivity in the visible light region is not sufficient. Therefore, it cannot be applied to a photoconductor having a wide range of visible light to near-infrared light and good photosensitivity. On the other hand, in order to obtain a photoconductor having a wide and good photosensitivity from the visible light region to the near infrared region, it is preferable to mix and use a phthalocyanine compound and another photoconductive material having a good photosensitivity in the visible light region. It is proposed in the following publication. For example, JP-A-59-151158 and JP-A-1-270060.
Japanese Unexamined Patent Application Publication No. Hei 1-246557 proposes a photosensitive member using phthalocyanine and a specific bisazo pigment, and Japanese Unexamined Patent Publication No. 1-246557 proposes a photosensitive member using phthalocyanine and a polycyclic quinone compound. Moreover, although the purpose is different,
Japanese Patent Laid-Open No. 2-54266 proposes a photoconductor using a phthalocyanine and a perinone compound.

[0004]

However, the previously proposed photoreceptors as described above are not suitable for speeding up the apparatus,
When it comes to downsizing, it is still insufficient in terms of light sensitivity, durability, and environmental stability. The present invention has been made in view of the above circumstances, and its purpose is to provide a wide range of good photosensitivity from visible light region to near infrared region, which is excellent in light sensitivity, durability, and environmental stability. It is intended to provide a photoconductor having the same.

[0005]

Means for Solving the Problems As a result of earnest search for a photoconductive material excellent in the above characteristics, the present inventors have found that by using a gallium phthalocyanine compound and a perylene compound or an anthanthrone compound in combination, photosensitivity, The inventors have found that a photoreceptor having excellent photosensitivity in a wide range from the visible light region to the near infrared region, which has excellent durability and environmental stability, can be obtained, and completed the present invention. In particular, this combination has the effects of increasing the dispersion stability of the photosensitive layer coating liquid and further increasing the photosensitivity in the visible light region as compared with the case of using the gallium phthalocyanine compound alone. That is, the electrophotographic photoreceptor of the present invention comprises a gallium phthalocyanine compound and a perylene compound represented by the following general formula (1) or an anthanthrone compound represented by the general formula (2) in the photosensitive layer as a carrier generating substance. It is characterized by doing.

[0006]

[Chemical 3] (In the formula, A ₁ , A ₁ ′, A ₂ and A ₂ ′ may be the same or different and each represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group containing a nitrogen atom in the ring. Represents.)

[0007]

[Chemical 4] (In the formula, X represents a halogen atom, a nitro group, a cyano group, an acyl group or a carboxy group, and n represents an integer of 0 to 4.)

The present invention will be described in detail below. In the present invention, the gallium phthalocyanine compound is preferably “chlorogallium phthalocyanine” (hereinafter, ClGaP
abbreviated as c) or "hydroxygallium phthalocyanine" (hereinafter abbreviated as HOGaPc) is used as the charge generation material. Among these, CuKα characteristic X
Bragg angle (2θ ± 0.2 in line diffraction spectrum
°), i) 7.4 °, 16.6 °, 25.5 ° and 28.3.
ClGaPc crystal having a strong diffraction peak at °, ii) 7.5 °, 9.9 °, 12.5 °, 16.3 °, 1
HOGaPc crystals with strong diffraction peaks at 8.6 °, 25.1 ° and 28.3 °, iii) 7.7 °, 16.5 °, 25.1 ° and 26.6.
HOGaPc crystals having a strong diffraction peak at °, iv) 7.9 °, 16.5 °, 24.4 ° and 27.6
HOGaPc crystals having a strong diffraction peak at °, v) 6.8 °, 12.8 °, 15.8 ° and 26.0
A HOGaPc crystal having a strong diffraction peak at 0 can be particularly preferably used.

These crystals can be obtained by crystallizing ClGaPc synthesized by a known method, or by crystallizing HOGaPc obtained by further hydrolysis. Specifically, i) the ClGaPc crystal is manufactured by Inorg. Chem. , 1
ClGaPc synthesized by the method described in 9,3131 (1980) and the like is made amorphous by dry pulverization and then treated with an aromatic alcohol solvent such as benzyl alcohol. ii) The HOGaPc crystal was prepared by adding ClGaPc to Bull. S
oc. Chim. France, 23 (1962), etc., after hydrolyzing by the method described in HOGaPc,
It can be obtained by crystal conversion treatment with an amide solvent such as dimethylformamide (DMF) or an acetic acid ester solvent such as butyl acetate. iii) The HOGaPc crystal is obtained by subjecting HOGaPc synthesized by the method described in the above literature to a crystal conversion treatment with an alcohol solvent such as methanol. iv) HOGaPc crystals are obtained by subjecting HOGaPc synthesized in the same manner as above to a crystal conversion treatment with an amide solvent such as DMF or an organic amine solvent such as pyridine or piperidine. v) The HOGaPc crystal is obtained by subjecting HOGaPc synthesized in the same manner as above to a crystal conversion treatment with a glycol solvent such as ethylene glycol.

These crystal conversion treatments may be carried out by washing with the solvent used, stirring in the solvent, or wet pulverization treatment with a ball mill, sand mill or the like. The amount of the solvent used is 1 to 200 parts by weight, preferably 10 to 100 parts by weight, based on the gallium phthalocyanine compound. The treatment temperature is 0 to 150 ° C., preferably room temperature to 100 ° C. The obtained gallium phthalocyanine crystal has absorptivity for light having a wavelength of 600 to 800 nm, and gives good photosensitivity characteristics, durability, and environmental stability.

Next, in the present invention, the perylene compound represented by the general formula (1) and the anthanthrone compound represented by the general formula (2), which are used together with the gallium phthalocyanine compound as a charge generation material, will be described. In the perylene compound represented by the general formula (1), A ₁ , A ₁ ′, A ₂ and A ₂ ′ each represent a divalent aromatic hydrocarbon group or a divalent heterocyclic group containing a nitrogen atom in the ring.
Examples of the aromatic hydrocarbon group such as o-phenylene group, o-naphthylene group, peri-naphthylene group, 1,2-anthraquinonylene group, 9,10-phenanthrylene group, and pyrazole-3,4-diyl group. Group, pyridine-2,3
-Diyl group, pyrimidine-4,5-diyl group, indazole-6,7-diyl group, benzimidazole-5,6
And nitrogen-containing heterocyclic groups such as -diyl group and quinoline-6,7-diyl group. These divalent groups may be the same or different from each other. The perylene-based pigment in the present invention is used in the state of a mixture of a trans-type compound represented by the upper formula of the general formula (1) and a cis-type compound represented by the lower formula, among which the following chemical formula (A) is used. The bisbenzimidazole perylene compounds shown can be preferably used.

[Chemical 5]

This perylene pigment is disclosed, for example, in J. Che
m. Soc. 1764 (1937), JP-A-3-24
It can be synthesized by a known method described in, for example, 059 publication. Further, it is preferable that the perylene compound is purified by sublimation by the method described in the above publication before being made into a pigment. These perylene compounds are mechanically crushed into a pigment by mechanically crushing a perylene pigment after synthesis or sublimation purification. As a method of mechanically pulverizing, any known means such as a ball mill, a mortar, a sand mill, a kneader, an attritor, a vibration mill and the like can be adopted. By using, it is possible to very efficiently pulverize into crystals with a regular grain size. The amount of the grinding aid used may be 5 to 200 parts by weight based on 10 parts by weight of the pigment. However, if the amount of the grinding aid is increased, although the grinding efficiency is increased to some extent, it is necessary to wash and remove after grinding, so excessive use is not preferable in production,
About 10 to 30 parts by weight is preferable.

In the anthanthrone compound represented by the general formula (2), the symbol X in the formula is a halogen atom,
It represents a nitro group, a cyano group, an acyl group or a carboxy group, and n represents an integer of 0-4. These substituents X
May be the same or different from each other when n represents an integer of 2 to 4, that is, when two or more substituents are present on the anthanthrone ring. Among these antoanthrone pigments, dibromoanthanthrone represented by the following chemical formula (B) can be preferably used, and commercially available products thereof can be used. In addition, it is preferable that the anthanthrone compound is purified by sublimation before being made into a pigment, and the anthanthrone compound can be made into a pigment by the same method as the above-mentioned perylene compound.

[Chemical 6] These perylene compounds and anthanthrone compounds have absorptivity for light having a wavelength of 450 to 600 nm and give good sensitivity characteristics.

In the present invention, a photosensitive layer containing the gallium phthalocyanine crystal and a perylene compound or an anthanthrone compound is provided on a conductive support, so that a wide range of good photosensitivity from visible light region to near infrared region can be obtained. It is possible to provide a photoreceptor having. The electrophotographic photosensitive member of the present invention may have a photosensitive layer having a single-layer structure or a laminated structure in which a charge-generating layer and a charge-transporting layer are functionally separated. The photosensitive layer or charge generating layer having a single-layer structure may be a single layer in which a gallium phthalocyanine compound and a perylene compound or an anthanthrone compound are mixed, or may be an independent layer. Further, an undercoat layer may be provided between the conductive support and the photosensitive layer. The conductive support may be any material that can be used as a support for an electrophotographic photoreceptor, such as a metal such as aluminum, a plastic film coated with a thin film of aluminum tin oxide, indium oxide, ITO, or the like. Further, an undercoat layer may be provided in order to prevent injection of charges from the conductive support to the photosensitive layer when the photosensitive layer is charged. For the undercoat layer, known materials such as polyamide resin, zirconium chelate compound and titanyl chelate compound can be used.

In the case where the photosensitive layer has a laminated structure and the gallium phthalocyanine compound and the perylene compound or the anthanthrone compound are laminated as the charge generation layer, the perylene pigment or the anthanthrone pigment is used because of carrier injection. It is desirable to stack so that electrons move toward the pigment and holes move toward the gallium phthalocyanine pigment. These independent layers may be formed by vacuum deposition of a perylene pigment or an anthrone pigment, or each charge generating material may be dispersed in a binder resin. In any case, the compounding ratio of the gallium phthalocyanine compound and the perylene compound or the anthanthrone compound in the photosensitive layer is
A weight ratio of 10: 1 to 1:10 is suitable, preferably 2: 1 to 1: 2. When the binder resin is used, the compounding ratio of the pigment and the resin is appropriately in the range of 10: 1 to 1:20, preferably 3: 1 to 1:10. The binder resin used is selected from a wide range of resins such as polyvinyl butyral resin and polyvinyl formal resin. The solvent that dissolves the binder resin is selected from those that do not dissolve the undercoat layer that is provided as necessary. For the dispersion of the pigment, a usual method such as a ball mill dispersion method, an attritor dispersion method or a sand mill dispersion method can be adopted. The application of the coating solution can be carried out by a usual method such as a blade coating method, a wire bar coating method, a spray coating method, a dip coating method, a bead coating method, an air knife coating method or a curtain coating method. The appropriate thickness of the charge generation layer is about 0.05 to 5 μm.

Similarly, when the photosensitive layer has a laminated structure, the charge transport layer is N, N'-diphenyl-N, N'-bis-.
(M-tolyl) benzidine, 4-diethylaminobenzaldehyde 2,2-diphenylhydrazone, p- (2,
It is formed by including a charge transport material such as 2-diphenylvinyl) -N, N-diphenylaniline in a suitable binder resin. The binder resin used for forming the charge transport layer may be a known resin such as a polycarbonate resin or a polyester resin, but is not limited thereto. The compounding ratio of the charge transport material and the binder resin is 1 by weight.
0: 1 to 1: 5 is preferable. The thickness of the charge transport layer is generally 5 to 50 μm, preferably 10 to 30 μm.

When the photosensitive layer has a single layer structure, the photosensitive layer is composed of the gallium phthalocyanine compound, the perylene compound or the anthanthrone compound, the charge transport material and the binder resin. As the charge transport material and the binder resin, the same materials as those having a laminated structure can be used. In this case, the compounding ratio of the charge transport material and the binder resin is 5: by weight.
The range of 1 to 1:20, the compounding ratio of the pigment and the charge transport material is 1
A range of 0: 1 to 1:10 is suitable. When the photosensitive layer has such a single layer structure, the residual potential is reduced as compared with the case where the gallium phthalocyanine compound is used alone. Further, in the electrophotographic photoreceptor of the present invention, a protective layer may be provided on the surface of the photosensitive layer, if necessary.

[0018]

EXAMPLES The present invention will be described in more detail with reference to the following examples. In the examples and comparative examples, "part" means "part by weight". Production Example 1 30 parts of 1,3-diiminoisoindoline and 9.1 parts of gallium trichloride were added to 230 parts of quinoline to give 200
After reacting at 0 ° C. for 3 hours, the product was filtered off, washed with acetone and methanol, and then the wet cake was dried to obtain 28 parts of ClGaPc crystals. The obtained ClGa
3 parts of Pc crystals were ground in an automatic mortar for 24 hours. After ball milling 1 part of crushed ClGaPc and 15 parts of benzyl alcohol with glass beads at room temperature for 24 hours, the crystal was washed with methanol to obtain 0.9 part of ClGaPc crystal. Powder X-ray diffraction pattern (XR
D) is shown in FIG. This crystal has a Bragg angle (2θ ± 0.2 °) in the CuKα characteristic X-ray diffraction spectrum.
Are 7.4 °, 16.6 °, 25.5 ° and 28.3 °
Had a strong diffraction peak.

Production Example 2 10 parts of gallium trichloride and 29.1 parts of phthalonitrile were added to 100 parts of α-chloronaphthalene, and the mixture was reacted at 200 ° C. for 24 hours under a nitrogen stream, and then the resulting ClGaP was formed.
The crystals of c were filtered off. The wet cake was dispersed in 100 parts of DMF, heated and stirred at 150 ° C. for 30 minutes, and then filtered.
Then, wash thoroughly with methanol, then dry to dry
28.9 parts (82.5%) of aPc crystal was obtained. 2 parts of ClGaPc synthesized by the above method was dissolved in 50 parts of concentrated sulfuric acid, stirred for 2 hours, and then added dropwise to a mixed solution of 170 parts of distilled water and 66 parts of concentrated ammonia water that had been ice-cooled to precipitate crystals. Let Wash the precipitated crystals thoroughly with distilled water,
It was dried to obtain 1.8 parts of HOGaPc crystal. This HOG
After ball milling 1 part of aPc crystals and 15 parts of DMF with glass beads at room temperature for 24 hours, the crystals were mixed with acetic acid
-Washing with butyl gave 0.9 parts of HOGaPc crystals.
The XRD of the obtained crystal is shown in FIG. This crystal is Cu
In the Kα characteristic X-ray diffraction spectrum, the Bragg angles (2θ ± 0.2 °) are 7.5 °, 9.9 °, and 12.5.
°, 16.3 °, 18.6 °, 25.1 ° and 28.
It had a strong diffraction peak at 3 °.

Production Example 3 3 parts of ClGaPc crystals of the cyclization reaction product obtained in Production Example 1 were dissolved in 60 parts of concentrated sulfuric acid at 0 ° C. and then added dropwise to 450 parts of distilled water at 5 ° C. to precipitate crystals. Let After washing with distilled water, diluted ammonia water, etc., it is dried to obtain HOGaPc crystals.
I got 5 copies. 1 part of this HOGaPc crystal and 15 parts of methanol were ball-milled with glass beads at room temperature for 24 hours, and then the crystal was washed with methanol to obtain HOGaPc.
0.9 parts of crystals were obtained. The XRD of the obtained crystal is shown in FIG. This crystal has a Bragg angle (2θ ± 0.2 °) of 7.7 ° and 1 in the CuKα characteristic X-ray diffraction spectrum.
It had strong diffraction peaks at 6.5 °, 25.1 ° and 26.6 °.

Production Example 4 HOGaPc crystal 1 obtained in Production Example 3 after treatment with concentrated sulfuric acid
And 15 parts of piperidine were ball-milled with glass beads at room temperature for 24 hours, and then the crystals were washed with methanol to obtain 0.9 parts of HOGaPc crystals. The XRD of the obtained crystal is shown in FIG. This crystal has a Bragg angle (2θ ± 0.2) in a CuKα characteristic X-ray diffraction spectrum.
°) is 7.9 °, 16.5 °, 24.4 ° and 27.
It had a strong diffraction peak at 6 °. Production Example 5 HOGaPc crystal 1 obtained in Production Example 3 after the concentrated sulfuric acid treatment
And 15 parts of ethylene glycol were stirred at 100 ° C. for 24 hours, and the crystals were washed with methanol to obtain HOGaP.
0.9 part of a c crystal was obtained. The XRD of the obtained crystal is shown in FIG. This crystal has a Bragg angle (2θ ± 0.2 °) of 6.8 ° in a CuKα characteristic X-ray diffraction spectrum.
It had strong diffraction peaks at 12.8 °, 15.8 ° and 26.0 °.

Production Example 6 (Synthesis of Bisbenzimidazole Perylene and Pigmentation) By the method described in JP-A-3-24059, bisbenzimidazole perylene (mixture of cis and trans isomers).
Was synthesized and purified by sublimation. 10 g of bisbenzimidazole perylene after sublimation purification was mixed with a planetary ball mill (Fri
tsch P-5) (menopot inner diameter 100 mmφ,
It was pulverized for 27 hours using 44 pieces of 20 mmφ menor balls and 3 pieces of 25 mmφ used. FIG. 6 shows a powder X-ray diffraction pattern of the obtained finely divided bisbenzimidazole perylene pigment.
Shown in. Production Example 7 (Pigmentation of dibromoanthanthrone) Dibromoanthanthrone (Monolight Red 2Y, IC
1 part (manufactured by Company I) was added to 2 parts of ethanol and stirred. Then, the mixture was poured into 6 parts of 6N hydrochloric acid, stirred at 90 ° C. for 1 hour, washed with distilled water, and dried. 45 g of dibromoanthanthrone treated as described above was added to a planetary ball mill (Fritsch P-5, above) (menopatting inner diameter 1
Using 12 pieces of 00 mmφ and 20 mmφ of menoballs), it was pulverized for 8 hours to obtain pigmented dibromoanthanthrone.

Examples 1 to 7 Zirconium compound (trade name: Organix ZC54
0, manufactured by Matsumoto Pharmaceutical Co., Ltd.) and 1 part of a silane compound (trade name: A1110, manufactured by Nippon Unicar Co., Ltd.), 40 parts of i-propanol and 20 parts of butanol are applied onto an aluminum substrate by a dip coating method. And heat-dry at 150 ° C for 10 minutes to obtain a film thickness of 0.2.
An undercoat layer of μm was formed. Then, 1 part of a mixture of the charge generation materials (CGM) obtained in Production Examples 1 to 7 as shown in Table 1 below was used as a polyvinyl butyral resin (trade name: S-REC BM-S, manufactured by Sekisui Chemical Co., Ltd.). After mixing with 1 part and 100 parts of cyclohexanone and treating with glass beads for 1 hour with a paint shaker to disperse, the obtained coating solution is applied on the above subbing layer by a dip coating method and heated at 100 ° C. for 10 minutes. 0.2 μm after drying
The charge generation layer of was formed. Next, 2 parts of the charge transport material represented by the following structural formula (I) and 3 parts of the polycarbonate resin represented by the structural formula (II) are dissolved in 20 parts of monochlorobenzene, and the resulting coating solution is formed into a charge generation layer. On the coated aluminum substrate by the dip coating method,
It was heated and dried at 0 ° C. for 1 hour to form a charge transport layer having a film thickness of 20 μm.

[0024]

[Chemical 7]

The electrophotographic characteristics of each electrophotographic photosensitive member thus produced were measured at room temperature and normal humidity (20 ° C., 40 ° C.) by using an electrostatic copying paper test apparatus (electrostatic analyzer EPA8100, manufactured by Kawaguchi Denki KK). % RH)
Under an environment of -6 KV, charged by corona discharge, exposed by white light with an illuminance of 5lux, and its surface potential becomes 1/2 of the initial potential E _1/2 (lux · sec), and Exposure amount E at which the surface potential becomes ½ of the initial potential after exposure with the light of a tungsten lamp of 1 μW / cm ² which is separated into monochromatic light of 780 nm using a monochromator.
_1/2 (mJ / m ² ) was measured. The results are shown in Table 1.

Comparative Examples 1 and 2 An electrophotography was conducted in the same manner as in Example 1 except that the bisbenzimidazole perylene pigment synthesized in Production Examples 6 and 7 and the dibromoanthanthrone pigment were used alone as the charge generating material. A photoconductor was prepared and its electrophotographic characteristics were measured. The results are shown in Table 1.

[0027]

[Table 1]

[0028]

INDUSTRIAL APPLICABILITY In the electrophotographic photoreceptor of the present invention, by using a gallium phthalocyanine compound having a high photosensitivity in the near infrared region in combination with a perylene compound or an anthanthrone compound, the dispersion stability of the coating liquid for the photosensitive layer is improved. And the photosensitivity in the visible light range becomes higher, and the photosensitivity, durability,
It has good photosensitivity in a wide range from visible light region, which has excellent environmental stability, to near infrared region.

[Brief description of drawings]

FIG. 1 shows a powder X-ray diffraction diagram of a chlorogallium phthalocyanine crystal obtained in Production Example 1.

FIG. 2 shows a powder X-ray diffraction pattern of the hydroxygallium phthalocyanine crystal obtained in Production Example 2.

FIG. 3 shows a powder X-ray diffraction pattern of the hydroxygallium phthalocyanine crystal obtained in Production Example 3.

FIG. 4 shows a powder X-ray diffraction pattern of the hydroxygallium phthalocyanine crystal obtained in Production Example 4.

FIG. 5 shows a powder X-ray diffraction pattern of the hydroxygallium phthalocyanine crystal obtained in Production Example 5.

FIG. 6 shows a powder X-ray diffraction pattern of the bisbenzimidazole perylene pigment obtained in Production Example 6.

Claims (9)

[Claims] 1. An electrophotographic photosensitive member comprising a gallium phthalocyanine compound and a perylene compound represented by the following general formula (1) as a carrier-generating substance in a photosensitive layer. [Chemical 1] (In the formula, A ₁ , A ₁ ′, A ₂ and A ₂ ′ may be the same or different and each represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group containing a nitrogen atom in the ring. Represents.) 2. An electrophotographic photoconductor comprising a gallium phthalocyanine compound and an anthanthrone compound represented by the following general formula (2) as a carrier generating substance in a photosensitive layer. [Chemical 2] (In the formula, X represents a halogen atom, a nitro group, a cyano group, an acyl group or a carboxy group, and n represents an integer of 0 to 4.) 3. The electrophotographic photosensitive member according to claim 1, wherein the gallium phthalocyanine compound is chlorogallium phthalocyanine. 4. The electrophotographic photosensitive member according to claim 1, wherein the gallium phthalocyanine compound is hydroxygallium phthalocyanine. 5. The chlorogallium phthalocyanine is Cu
In the Kα characteristic X-ray diffraction spectrum, the Bragg angles (2θ ± 0.2 °) are 7.4 °, 16.6 °, and 25.5.
The electrophotographic photosensitive member according to claim 3, which is a chlorogallium phthalocyanine crystal having a strong diffraction peak at 2 ° and 28.3 °. 6. The hydroxygallium phthalocyanine is
In the CuKα characteristic X-ray diffraction spectrum, the Bragg angles (2θ ± 0.2 °) were 7.5 °, 9.9 °, and 12.5.
°, 16.3 °, 18.6 °, 25.1 ° and 28.
The electrophotographic photosensitive member according to claim 4, which is a hydroxygallium phthalocyanine crystal having a strong diffraction peak at 3 °. 7. The hydroxygallium phthalocyanine comprises:
In the CuKα characteristic X-ray diffraction spectrum, the Bragg angle (2θ ± 0.2 °) was 7.7 °, 16.5 °, 25.
The electrophotographic photosensitive member according to claim 4, which is a hydroxygallium phthalocyanine crystal having strong diffraction peaks at 1 ° and 26.6 °. 8. The hydroxygallium phthalocyanine comprises:
In the CuKα characteristic X-ray diffraction spectrum, the Bragg angle (2θ ± 0.2 °) was 7.9 °, 16.5 °, 24.
The electrophotographic photosensitive member according to claim 4, which is a hydroxygallium phthalocyanine crystal having strong diffraction peaks at 4 ° and 27.6 °. 9. A hydroxygallium phthalocyanine,
In the CuKα characteristic X-ray diffraction spectrum, the Bragg angle (2θ ± 0.2 °) was 6.8 °, 12.8 °, 15.
The electrophotographic photosensitive member according to claim 4, which is a hydroxygallium phthalocyanine crystal having strong diffraction peaks at 8 ° and 26.0 °.