JPH08176458A - Phthalocyanine composition and eletrophotographic photoreceptor - Google Patents

Abstract

PURPOSE: To obtain a phthalocyanine composition suitable for making a photoreceptor with high γ characteristics. CONSTITUTION: This composition is one containing at least 50mol% titanyl phthalocyanine and showing Bragg angles (2θ±0.02 deg.) of 7.0 deg., 7.6 deg., 9.7 deg., 10.2 deg., 15.6 deg., 22.4 deg., 23.5 deg., 24.3 deg., 25.4 deg., 27.3 deg. and 28.6 deg. in the X-ray spectrum.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a phthalocyanine composition having a specific crystal type and an electrophotographic photoreceptor using the phthalocyanine composition.

[0002]

2. Description of the Related Art Phthalocyanines have been actively studied as excellent optical semiconductor materials. Electrophotographic photoconductors, electrophotographic plate-making materials, solar cells, photoelectric conversion materials such as image sensors, optical memory materials such as optical disks and photochromism, photo hole burning (PHB) sensitizers, gas sensors that utilize semiconductor characteristics, Research on organic diode materials is becoming active. In particular, phthalocyanine, which has high sensitivity up to a long wavelength region, is being actively researched and developed as a charge generating material for electrophotographic photoreceptors for semiconductor lasers and electrophotographic photoreceptors for light emitting diodes.

Phthalocyanines not only have different absorption spectra and photoconductivity depending on the type of central metal, but also have different physical properties depending on the crystal type. For example, copper phthalocyanine is known to have a large difference in electrophotographic electric properties such as chargeability, dark decay, and sensitivity due to differences in crystal types such as α, β, γ, and ε types [Gaku Sawada: "Dyes and Chemicals" Vol. 24, No. 6, p12
2 (1979)]. In addition, in the case of electrophotographic photoreceptors,
Several examples have been reported in which a particular crystal form has been selected. A photoreceptor using a metal-free phthalocyanine (for example,
JP-A-60-86551), a photoreceptor using an aluminum-containing phthalocyanine (for example, JP-A-63-153).
33462) and many other central metals such as titanium (for example, JP-A-59-49544), indium and gallium are known as the central metal, and most of them select a specific crystal type.

[0004] Titanyl phthalocyanine (hereinafter also referred to as oxytitanium phthalocyanine) exhibits high sensitivity and has been particularly attracting attention in recent years, and various crystal systems have been proposed as effective charge generating materials for electrophotographic photoreceptors. ing. For example, JP-A-61-217050 discloses an α type, JP-A-59-49544 discloses a β type, and JP-A-62-256865 discloses a C type. Japanese Unexamined Patent Publication No. 62-67094 discloses D
Japanese Patent Application Laid-Open No. 64-17066 discloses Y type, Japanese Patent Application Laid-Open No. 1-299874 discloses γ type, and Japanese Patent Application Laid-Open No. 2-99969 discloses ω type. There is. In the X-ray diffraction spectrum, 2θ ± 0.2
The D type is known to have a peak around ° = 27.2 °. On the other hand, Japanese Patent Laid-Open No. 1-1426
No. 59, No. 2-70763, No. 2-170166,
JP-A-2-272067 and JP-A-2-280169.
The publication discloses that a mixed crystal of oxytitanium phthalocyanine and another phthalocyanine or a simple mixture thereof is used as a charge generating material of an electrophotographic photoreceptor.

[0005]

However, the above-mentioned various titanyl phthalocyanines and mixed crystals are useful as charge generating materials, but they are not yet sufficient. In particular, it has been desired to develop a charge generating agent having a high γ characteristic required for an electrophotographic photosensitive member for so-called digital light input and having other favorable characteristics. Therefore, an object of the present invention is to provide a phthalocyanine composition having high γ characteristics and other good photosensitivity characteristics, and an electrophotographic photoreceptor using the same.

[0006]

The present invention is a phthalocyanine composition containing at least 50% by mole of titanyl phthalocyanine in a mole fraction, and has a black angle (2θ ± 0.2 °) of 7.0 ° in an X-ray diffraction spectrum. , 7.6 °,
9.7 °, 10.2 °, 15.6 °, 22.4 °, 2
3.5 °, 24.3 °, 25.4 °, 27.3 °, 2
A phthalocyanine composition having a peak at 8.6 °, which has excellent performance as an electrophotographic photoreceptor,
And an electrophotographic photoreceptor comprising the composition in a photosensitive layer.
Hereinafter, the present invention will be described in detail.

The phthalocyanine composition of the present invention has a molar fraction of titanyl phthalocyanine of at least 50%, preferably 95-60%, more preferably 95-7.
It is 0%. If the mole fraction is low, the photosensitivity will be poor and it will not be suitable for practical use. Examples of titanyl phthalocyanine include, for example, the following general formula [1]

[0008]

Embedded image

(Wherein X represents a halogen atom and n represents a number from 0 to 1). As the other phthalocyanine, one or more compounds selected from metal-free or metal phthalocyanines or their derivatives are used. Examples of these phthalocyanines include metal-free phthalocyanine; beryllium phthalocyanine; magnesium phthalocyanine; aluminum phthalocyanine; silicon phthalocyanine; vanadium phthalocyanine; chromium phthalocyanine; manganese phthalocyanine; iron phthalocyanine; cobalt phthalocyanine; nickel phthalocyanine; copper phthalocyanine; zinc phthalocyanine; gallium phthalocyanine. Germanium phthalocyanine; zirconium phthalocyanine; niobium phthalocyanine; molybdenum phthalocyanine; palladium phthalocyanine: silver phthalocyanine; cadmium phthalocyanine; indium phthalocyanine; tin phthalocyanine; antimonaphthalocyanine; tantalum phthalocyanine; tungsten phthalocyanine; platinum Thallocyanine; gold phthalocyanine; mercury phthalocyanine; metal phthalocyanines such as thallium phthalocyanine and lead phthalocyanine, and hydrogen atoms of the benzene ring of these metal-free or metal phthalocyanines are substituted with a substituent such as chlorine, fluorine, nitro group, cyano group or sulfone group. Examples thereof include substituted phthalocyanine derivatives.

The method for synthesizing phthalocyanine is described in Moser and Thomas's "Phthalocyanine Compound" (MOSER).
and Thomas. "Phthalocianin
eCompounds "), for example, in the case of titanyl phthalocyanine, O-
A method in which phthalonitrile and titanium tetrachloride are melted by heating or heated in the presence of an organic solvent such as α-chloronaphthalene, 1,3-diiminoisoindoline and tetrabutoxytitanium are heated with an organic solvent such as N-methylpyrrolidone. Depending on the method, it can be obtained in good yield. The obtained phthalocyanine may contain a phthalocyanine derivative in which the hydrogen atom of the benzene ring is substituted with a substituent such as chlorine, fluorine, nitro group, cyano group or sulfone group. The phthalocyanine obtained by synthesis may be of any crystal type and may be amorphous. Preferably, it is in the α-type or amorphous state.

Such a phthalocyanine composition is added to an alicyclic organic solvent having a carbonyl group in the presence of water and subjected to solvent treatment to obtain the crystalline form of the present invention. As a method of treating phthalocyanine with an alicyclic organic solvent having a carbonyl group in the presence of water, a method of preliminarily swelling phthalocyanine with water and treating with an organic solvent, or without swelling treatment, water is treated with an organic solvent. Examples thereof include a method in which the phthalocyanine powder is added, and the method is not limited thereto.

As a method of swelling phthalocyanine with water, for example, a method of dissolving phthalocyanine in sulfuric acid and precipitating it in water to form a wet paste. Further, a method of swelling the phthalocyanine with water using a stirring / dispersing device such as a homomixer, a paint mixer, a ball mill, or a sand mill to form a wet paste can be mentioned, but the method is not limited to these. .

Examples of the alicyclic organic solvent having a carbonyl group include carbonates such as ethylene carbonate, propylene carbonate, butylene carbonate, chloroethylene carbonate, γ-butyrolactone, γ-valerolactone, δ-valerolactone, ε-caprolactone, α-methylene-γ-butyrolactone, α-bromo-
γ-valerolactone, γ-caprolactone, 2-acetylbutyrolactone, α-acetyl-α-methyl-γ-butyrolactone, α-bromo-γ-butyrolactone, α-
Lactones such as andiericalactone, 2-cyclohexen-1-one, 4-chromanone, 1-decalone, 3,
4-di-hydrocoumarin, 2 (5H) -furanone, tropone, α-tetralone, 1-indanone, 2H-pyran-2-one and the like can be mentioned. Of these, carbonates such as ethylene carbonate, propylene carbonate, butylene carbonate and chloroethylene carbonate, and lactones such as γ-butyrolactone and δ-valerolactone are preferable.

As a device used for this treatment, a homomixer, a paint mixer, a disperser, an agitator, a ball mill, a sand mill, an attritor, an ultrasonic dispersion device or the like can be used in addition to a general stirring device. . The processing temperature is −80 to 120 ° C. Preferably, it is -50 to 80 ° C, and more preferably -30 to 5
0 ° C. The processing time is 10 minutes to 120 hours, preferably 10 minutes to 50 hours. The amount of the alicyclic organic solvent having a carbonyl group is 1 to 50 with respect to the weight of phthalocyanine.
0 times, preferably 1 to 300 times, and more preferably 1 to
It is set to 100 times. After treatment, filtered, methanol,
It is isolated by washing with an alicyclic organic solvent having a carbonyl group such as ethanol and water and an easy solvent.

The phthalocyanine composition of the present invention is not limited to those produced by the above-mentioned production method, and any production method can be used as long as it exhibits the specific peak of the present invention. Is. Now,
The phthalocyanine composition of the present invention thus obtained,
In an X-ray diffraction spectrum measured by Cu-Kα ray, black angle (2θ ± 0.2 °) 7.0 °, 7.6
°, 9.7 °, 10.2 °, 15.6 °, 22.4 °,
23.5 °, 24.3 °, 25.4 °, 27.3 °, 2
It is characterized by having at least a peak at 8.6 °. Among these, the peak at 7.6 ° or 28.6 °
Phthalocyanine compositions exhibiting higher peak intensity than other peaks are preferable because they exhibit good photosensitivity characteristics.

The phthalocyanine composition thus obtained exhibits particularly excellent properties when used as a carrier generating substance for an electrophotographic photoreceptor. In order to use the phthalocyanine composition of the present invention as an electrophotographic photoreceptor, the phthalocyanine composition produced by the above method is uniformly mixed with a binder resin, a solvent and the like in a kneading disperser such as a ball mill and an attritor. The photosensitive layer may be dispersed and applied on a conductive support to form a photosensitive layer.

That is, the phthalocyanine composition and the binder resin are mixed in a weight ratio of the binder resin to the phthalocyanine composition of about 1 to 10. Then, the mixed phthalocyanine composition and the binder resin are coated on an aluminum plate or a conductive support such as electroconductively treated paper or plastic that is usually used for electrophotographic photoconductors to form a photosensitive layer. Let As the coating method, if necessary, a solvent such as toluene or cyclohexanone is added to the mixture to adjust the viscosity, and an air doctor coater, a plate coater, a rod coater, a reverse coater, a spray coater, a hot coater, a squeeze coater, a gravure coater, The coating is formed by a coating method such as a dip coating method. After coating, appropriate drying is carried out until a sufficient charging potential is imparted as a photoconductive layer.

Examples of the binder resin include melamine resin, epoxy resin, silicon resin, polyurethane resin, polyester resin, alkyd resin, acrylic resin, xylene resin, vinyl chloride vinyl acetate copolymer resin, polycarbonate resin, and fibrin derivative. Volume resistivity of 10 ⁷ Ω
Examples thereof include a binder resin having an insulating property of cm or more, or a binder resin such as polyvinyl carbazole.

The photoconductor prepared by using the phthalocyanine composition of the present invention and the above means (hereinafter referred to as the photoconductor of the present invention) has a resin / photoconductive material weight ratio of 1 or more. . Therefore, for example, the amount of resin is larger than in the case of the conventional photoconductor using zinc oxide in which the weight ratio of resin / photoconductive material is 0.2. Therefore, it is possible to realize a photoconductor having a physical strength of the coating and being highly flexible. Further, the photoconductor of the present invention produced as described above has a large adhesiveness with a conductive support, good moisture resistance, little economic change, few toxicity problems, and easy production. In addition, it has practically excellent features such as being inexpensive. Hereinafter, the present invention will be described with reference to examples.

[0020]

【Example】

(Production example of titanyl phthalocyanine) 58 g of 1,3-diiminoisoindoline and 51 g of tetrabutoxytitanium were reacted in 300 ml of α-chloronaphthalene at 210 ° C. for 5 hours, and then α-chloronaphthalene and dimethylformamide (DMF) were sequentially added. Washed with. Then, it was washed with hot DMF, hot water and methanol and dried to obtain 51 g of titanyl phthalocyanine.

(Production Example of Metal-Free (Hydrogen) Phthalocyanine) 58 g of 1,3-diiminoisoindoline α-
After reacting in 300 ml of chloronaphthalene at 210 ° C. for 5 hours, α-chloronaphthalene and dimethylformamide (DMF) were washed in this order. Then, heat DM at 150 ℃
F, 80 ° C. hot water, and methanol were further washed in this order. Finally, it was dried at 60 ° C. to obtain 42 g of metal-free (hydrogen) phthalocyanine.

(Production Example of Copper Phthalocyanine) 54 g of phthalic anhydride, 93 g of urea, cupric chloride (anhydride) 15.3
and 450 g of ammonium molybdate were reacted in 450 ml of nitrobenzene at 190 ° C. for 5 hours, and then washed with nitrobenzene and methanol in that order. Then, it was boiled for 1 hour in 1000 ml of 1N hydrochloric acid aqueous solution. Immediately after boiling, the mixture was filtered while hot and washed with sufficient water until the filtrate became neutral. Then, 1N sodium hydroxide aqueous solution 1
Boiled in 000 ml for 1 hour. Immediately after boiling, the mixture was filtered while hot and washed with sufficient water until the filtrate became neutral. Finally, it was dried at 120 ° C. to obtain 42 g of copper phthalocyanine.

(Example 1) 2 g of titanyl phthalocyanine
And 0.45 g of the metal-free (hydrogen) phthalocyanine synthesized above was dissolved in 350 g of sulfuric acid at 0 ° C. (mol fraction of titanyl phthalocyanine 80%). Next, the sulfuric acid solution was added dropwise to 600 ml of water and 2200 g of ice, after completion of the addition, the mixture was stirred at room temperature for 1 hour and then filtered, and washed with sufficient water until the filtrate became neutral.

Next, the wet paste is put into 250 ml of propylene carbonate (hereinafter abbreviated as PC) kept at 25 ° C. to carry out the solvent treatment of phthalocyanine with PC in the presence of water. Then, this process was continued for 6 hours while mechanically stirring the PC solution in which the wet paste was mixed. After this treatment was carried out for 6 hours, phthalocyanine was washed with methanol and filtered. Finally, the phthalocyanine composition 1 was dried at 60 ° C. to obtain 2.3 g. The X-ray diagram of this phthalocyanine is shown in FIG. Black angle (2θ ± 0.2 °), 7.0
°, 7.6 °, 9.7 °, 10.2 °, 15.6 °, 2
2.4 °, 23.5 °, 24.3 °, 25.4 °, 2
It can be seen that the phthalocyanine composition of the present invention has peaks at 7.3 ° and 28.6 °.

(Example 2) 2 g of titanyl phthalocyanine
And 0.45 g of the metal-free (hydrogen) phthalocyanine synthesized above was dissolved in 350 g of sulfuric acid at 0 ° C. (mol fraction of titanyl phthalocyanine 80%). Next, the sulfuric acid solution was added dropwise to 600 ml of water and 2200 g of ice, after completion of the addition, the mixture was stirred at room temperature for 1 hour and then filtered, and washed with sufficient water until the filtrate became neutral.

Then, the wet paste is put into 250 ml of γ-butyrolactone (hereinafter abbreviated as GBL) kept at 25 ° C. to carry out a solvent treatment of phthalocyanine with GBL in the presence of water. Then, this treatment was continued for 8 hours while mechanically stirring the GBL solution mixed with the wet paste. After this treatment was carried out for 8 hours, phthalocyanine was washed with methanol and filtered. Finally, the phthalocyanine composition 2 was dried at 60 ° C. to obtain 2.2 g. The X-ray diagram of this phthalocyanine is shown in FIG. Black angle (2θ ± 0.2 °), 7.
0 °, 7.6 °, 9.7 °, 10.2 °, 15.6 °,
22.4 °, 23.5 °, 24.3 °, 25.4 °, 2
It can be seen that the phthalocyanine composition of the present invention has peaks at 7.3 ° and 28.6 °.

Example 3 Titanyl phthalocyanine 1.
2 g and 0.7 g of metal-free (hydrogen) phthalocyanine were dissolved in 270 g of sulfuric acid at 0 ° C. (titanyl phthalocyanine mole fraction 60%). Then, add the sulfuric acid solution to 400 m of water.
1 and 800 g of ice, the mixture was stirred at room temperature for 1 hour after completion of the dropping, filtered, and washed with sufficient water until the filtrate became neutral.

Next, the wet paste is put into 200 ml of PC kept at 25 ° C. to carry out the solvent treatment of phthalocyanine with PC in the presence of water. Then, this process was continued for 6 hours while mechanically stirring the PC solution in which the wet paste was mixed.
After this treatment was carried out for 6 hours, phthalocyanine was washed with methanol and filtered. Finally, the phthalocyanine composition 3 was dried at 60 ° C. to obtain 1.7 g. The X-ray diagram of this phthalocyanine is shown in FIG. Black angle (2θ ±
0.2 °), 7.0 °, 7.6 °, 9.7 °, 10.2
°, 15.6 °, 22.4 °, 23.5 °, 24.3
It can be seen that the phthalocyanine composition of the present invention has peaks at °, 25.4 °, 27.3 °, and 28.6 °.

(Example 4) Titanyl phthalocyanine 1.
5 g and 0.33 g of the above-synthesized copper phthalocyanine were added at 0 ° C.
Dissolved in 260 g of sulfuric acid (titanyl phthalocyanine mole fraction 80%). Next, the sulfuric acid solution was added dropwise to 400 ml of water and 900 g of ice, after completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour and then filtered, and washed with sufficient water until the filtrate became neutral.

Next, the wet paste is put into 200 ml of PC kept at 25 ° C. to carry out a solvent treatment of phthalocyanine with PC in the presence of water. Then, this process was continued for 6 hours while mechanically stirring the PC solution in which the wet paste was mixed.
After this treatment was carried out for 6 hours, phthalocyanine was washed with methanol and filtered. Finally, the phthalocyanine composition 4 was dried at 60 ° C. to obtain 1.7 g. The X-ray diagram of this phthalocyanine is shown in FIG. Black angle (2θ ±
0.2 °), 7.0 °, 7.6 °, 9.7 °, 10.2
°, 15.6 °, 22.4 °, 23.5 °, 24.3
It can be seen that the phthalocyanine composition of the present invention has peaks at °, 25.4 °, 27.3 °, and 28.6 °. Hereinafter, a method for producing phthalocyanine as a comparative example used for evaluating the phthalocyanine composition according to each example of the present invention will be described.

Comparative Example 1 Comparative Example 1 differs from Example 1 in that the wet paste is dried immediately without being treated with propylene carbonate. 2 g of the above-synthesized titanyl phthalocyanine was dissolved in 300 g of sulfuric acid at 0 ° C. Next, the sulfuric acid solution was dropped into 800 ml of water and 1600 g of ice,
After completion of dropping, the mixture was stirred at room temperature for 1 hour, filtered, and washed with sufficient water until the filtrate became neutral. Finally, it was dried at 60 ° C. to obtain 0.9 g. An X-ray diagram of this phthalocyanine is shown in FIG.
Shown in It has a broad diffraction pattern, which is different from the phthalocyanine composition of the present invention.

Comparative Example 2 Comparative Example 2 differs from Example 3 only in that the mole fraction of titanyl phthalocyanine is 40%. 1.1 g of titanyl phthalocyanine and 1.5 g of metal-free (hydrogen) phthalocyanine were added to 380 g of sulfuric acid at 0 ° C.
Dissolved in. Next, the sulfuric acid solution was added to 500 ml of water and 2 pieces of ice.
The mixture was added dropwise to 500 g, and after completion of the dropping, the mixture was stirred at room temperature for 1 hour, filtered, and washed with sufficient water until the filtrate became neutral.

Then, the wet paste is put into 250 ml of PC kept at 25 ° C. to carry out the solvent treatment of phthalocyanine with PC in the presence of water. Then, this process was continued for 6 hours while mechanically stirring the PC solution in which the wet paste was mixed.
After this treatment was carried out for 6 hours, phthalocyanine was washed with methanol and filtered. Finally, the phthalocyanine composition 6 was dried at 60 ° C. to obtain 1.75 g. The X-ray diagram of this phthalocyanine is shown in FIG. Black angle (2θ ±
0.2 °), 7.0 °, 7.6 °, 9.7 °, 10.2
°, 15.6 °, 22.4 °, 24.3 °, 25.4
Has peaks at °, 27.3 °, and 28.6 °, but 2
It has no peak at 3.5 °, which is different from that of the present invention.

Comparative Example 3 Comparative Example 3 differs from Example 2 only in that the wet paste is treated with dimethyl carbonate instead of γ-butyrolactone. 2 g of titanyl phthalocyanine and 0.45 g of the metal-free (hydrogen) phthalocyanine synthesized above were dissolved in 350 g of sulfuric acid at 0 ° C. (Titanyl phthalocyanine mole fraction 80%). Next, the sulfuric acid solution was added with 600 ml of water at 0 ° C. and 2200 g of ice.
After the dropping, the mixture was stirred at room temperature for 1 hour after completion of the dropping, filtered, and washed with sufficient water until the filtrate became neutral.

Next, the wet paste is subjected to a solvent treatment with 250 ml of dimethyl carbonate kept at 25 ° C. Then, this treatment was connected for 12 hours while mechanically stirring the dimethyl carbonate solution mixed with the wet paste. After performing this treatment for 12 hours, the phthalocyanine was washed with water and filtered.
Finally, the phthalocyanine composition 7 was dried at 60 ° C. to obtain 2.3 g. The X-ray diagram of this phthalocyanine is shown in FIG. Black angle (2θ ± 0.2 °), 7.6 °, 9.
7 °, 15.6 °, 22.4 °, 23.5 °, 25.4
7. Has peaks at 2 °, 27.3 ° and 28.6 °, but 7.
The peaks at 0 ° and 24.3 ° are not in the range of ± 0.2 °, and there is no peak at 10.2 °, which is different from that of the present invention.

(Evaluation) The phthalocyanine composition obtained as described above was evaluated as follows. That is, polyester resin solution (Marmatex, P64
5, Mitsui Toatsu Co., Ltd. 2.8 g, melamine resin (Corban,
20 g, manufactured by Mitsui Toatsu Co., Ltd.) and 14 g of toluene are mixed, and 0.8 g of the above-mentioned phthalocyanine is added together with 30 g of glass beads. This was dispersed with a paint mixer for 4 hours to obtain a photoreceptor coating liquid. Next, this photoreceptor coating is coated on a 90-micron-thick aluminum foil so that the dry film thickness is 15 microns, and the temperature is 120 ° C.
It was left still for 5 hours. The photoreceptor was prepared as described above.

Next, the photosensitivity characteristics of the obtained photoconductor were evaluated by using a photoconductor evaluation device (Cynthia 55, manufactured by Gentech). First, the dark decay time was defined as the time (seconds) at the inflection point where the surface potential of the photoconductor drastically drops when corona charged at a voltage of +6.0 KV.

The optical characteristics are defined as follows. That is, 780 nm monochromatic light having different light intensity was irradiated to each corona-charged photoreceptor, and a light decay time curve (characteristic curve of surface potential against irradiation time) for each light intensity was measured. Then, the surface potential after irradiation for a certain period of time (here, 0.075 seconds) obtained from the curve was plotted against the light energy. This is called a γ curve.

The maximum light energy among the light energies capable of maintaining the surface potential at about the same level as the initial charging is E
₁ (light energy at the rising point in the γ curve),
Of the light energies that can reduce the surface potential to about the residual potential (about 30 V), the minimum light energy is E ₂ (light energy at the rising point in the γ curve).
And The smaller E ₁ is, the better the photosensitivity is. Also, E
_The smaller the difference ΔE between _2- E ₁ is, the higher the γ characteristic is, and thus the photoreceptor can be a digital light input photoreceptor. In this evaluation method, it was evaluated that the photoconductor having ΔE of 5 μJ / cm ² or less can be used as a digital photoconductor and the photoconductor having a ΔE of 5 μJ / cm ² or more can be used as an analog photoconductor. Table 1 shows the evaluation results.

[0040]

[Table 1]

[0041]

According to the present invention, a high γ characteristic can be obtained, so that it can be used as a photoreceptor for digital optical input. Also, the residual potential is low and good sensitivity characteristics can be obtained.

[Brief description of drawings]

FIG. 1 is an X-ray diagram of phthalocyanine obtained in Example 1 of the present invention.

FIG. 2 is an X-ray diagram of phthalocyanine obtained in Example 2 of the present invention.

FIG. 3 is an X-ray diagram of phthalocyanine obtained in Example 3 of the present invention.

FIG. 4 is an X-ray diagram of phthalocyanine obtained in Example 4 of the present invention.

5 is an X-ray diagram of phthalocyanine obtained in Comparative Example 1. FIG.

6 is an X-ray diagram of phthalocyanine obtained in Comparative Example 2. FIG.

7 is an X-ray diagram of phthalocyanine obtained in Comparative Example 3. FIG.

Claims (2)

[Claims] 1. A phthalocyanine composition containing at least 50% by mole of titanyl phthalocyanine in a mole fraction, and having a black angle (2θ ± 2) in an X-ray diffraction spectrum.
0.2 °) 7.0 °, 7.6 °, 9.7 °, 10.2
°, 15.6 °, 22.4 °, 23.5 °, 24.3
A phthalocyanine composition having peaks at °, 25.4 °, 27.3 ° and 28.6 °. 2. An electrophotographic photoreceptor having a photosensitive layer provided on a conductive substrate, containing at least 50% by mole of titanyl phthalocyanine in a mole fraction, and having a black angle (2θ ± 0.2 °) in an X-ray diffraction spectrum. 7.0 °, 7.6
°, 9.7 °, 10.2 °, 15.6 °, 22.4 °,
23.5 °, 24.3 °, 25.4 °, 27.3 °, 2
An electrophotographic photoreceptor comprising a phthalocyanine composition having a peak at 8.6 ° in the photosensitive layer.