JPH06118677A - Electriophotographic sensitive body - Google Patents

Abstract

PURPOSE:To provide an electrophotographic sensitive body which has excellent sensitivity characteristics, is useful for a high-speed printer, high-speed digital copying machine or high-speed facsimile, is less changed in the sensitivity characteristics with a fluctuation in humidity, has the stable characteristics at the time of repetitive use, has excellent production stability and is less fluctuated in the characteristics. CONSTITUTION:This electrophotographic sensitive body contains titanyl phthalocyanine of a crystal type having the max. peak at 27.2+ or -0.2 deg. of a Bragg angle 2theta in X-ray diffraction spectra with Cu-Kalpha rays and contains a non-arom. cyclic compd. having at least one kind among -OH, -COOH, -NHR, -NH2, -SH (where R denotes a substd. or unsubstd. alkyl group) as a substituent in a 0.1 to 1000 pts.wt. range per 100 pts.wt. titanyl phthalocyanine.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an electrophotographic photoreceptor,
In particular, titanyl phthalocyanine having a specific crystal type is used as a photoconductive material, it is effective for a printer, a copying machine and the like, and is also suitable when an image is formed by using a semiconductor laser light and an LED light as an exposing means. Electrophotographic photoconductor.

[0002]

2. Description of the Related Art In recent years, photoconductive materials have been actively researched and applied to photoelectric conversion elements such as electrophotographic photoreceptors, solar cells and image sensors.
Conventionally, inorganic materials are mainly used as these photoconductive materials. For example, in an electrophotographic photoreceptor, a photosensitive layer containing an inorganic photoconductive material such as selenium, zinc oxide, or cadmium sulfide as a main component is provided. Inorganic photoreceptors have been widely used.

However, such an inorganic photoconductor has not always been satisfactory in characteristics such as photosensitivity, thermal stability, moisture resistance and durability required for electrophotographic photoconductors of copying machines, printers and the like. For example, selenium is crystallized by heat, stains on fingerprints, etc., so that the characteristics as an electrophotographic photoreceptor are likely to deteriorate. Further, the electrophotographic photoreceptor using cadmium sulfide is inferior in moisture resistance and durability, and the electrophotographic photoreceptor using zinc oxide also has a problem in durability.

Further, in recent years, environmental problems have been particularly emphasized, but electrophotographic photoconductors such as selenium and cadmium sulfide have a drawback in that production and handling are largely restricted in view of toxicity.

In order to remedy the drawbacks of such inorganic photoconductive materials, various organic photoconductive materials have been attracting attention, and in recent years, attempts have been made to use them in the photosensitive layer of electrophotographic photoreceptors. Active research is being conducted. For example, Japanese Patent Publication No. 50-10496 describes an organic photoreceptor having a photosensitive layer containing polyvinylcarbazole and trinitrofluorenone. However, this photoreceptor is not sufficient in sensitivity and durability. Therefore, a function-separated electrophotographic photosensitive member has been developed in which different substances have different functions of carrier generation and carrier transport.

In such an electrophotographic photosensitive member, since a wide range of materials can be selected, it is easy to obtain arbitrary characteristics,
Therefore, it is expected that an organic photoreceptor having high sensitivity and high durability can be obtained.

Various organic compounds have been proposed as carrier-generating substances and carrier-transporting substances for such a function-separated type electrophotographic photosensitive member. In particular, the carrier-generating substance is important for controlling the basic characteristics of the photosensitive member. Has various functions. As carrier generating substances, photoconductive substances such as polycyclic quinone compounds typified by dibromoanthanthrone, pyrylium compounds and eutectic complexes of pyrylium compounds, squarylium compounds, phthalocyanine compounds, and azo compounds have been put to practical use. It was

Among them, it is known that titanyl phthalocyanine having a specific crystal form exhibits particularly excellent characteristics. Titanyl phthalocyanine has numerous crystal forms,
Although it shows completely different properties depending on the crystal type,
In particular, since crystalline titanyl phthalocyanine having a maximum peak at 27.2 ± 0.2 ° of Bragg angle 2θ in the X-ray diffraction spectrum for Cu-Kα ray has remarkably high photon efficiency, such titanyl phthalocyanine was used as a carrier generating substance. Electrophotographic photoreceptors have become extremely useful in the design of high speed printers, high speed digital copiers and high speed facsimiles.

Fujimaki says that the X-ray diffraction spectrum is 9.5.
Y-type titanyl phthalocyanine, which has characteristic peaks at 2 ° and 27.2 ° and is known to have extremely high photon efficiency, shows that the photon efficiency is reduced by dehydration treatment in a heated or dried inert gas. I found it.
Since the photon efficiency is restored again when water is reabsorbed in a room temperature and normal humidity environment, the Y-type crystal is a crystal that absorbs water, and the dissociation of holes and electrons of excitons generated by light by water molecules. It is considered that this is one of the causes of high photon efficiency (Y.Fujima).
ki: IS & T ′s 7th International Congress on Advance
in Nonimpact Printing Technologies, Paper Summari
es, 269 (1991)). When such a material is used as a carrier-generating substance, the sensitivity characteristics may change due to environmental changes, particularly humidity fluctuations, which causes practical problems and requires improvement.

On the other hand, in order to form the photosensitive layer, the desired titanyl phthalocyanine is usually added with a binder polymer in an organic solvent, and finely dispersed using various dispersing devices to obtain a dispersion liquid. Coating is performed on a conductive substrate. In general, a compound having a crystal polymorphism has different crystal stability depending on environmental conditions, and therefore, a crystal state is often changed in a dispersion liquid under the influence of a solvent or a binder. In particular, titanyl phthalocyanine used in the present invention is used. The crystals show very high photon efficiencies, and it is expected that slight changes in the crystalline state will have an important effect on the photoreceptor properties. Therefore, it is important to suppress such changes in the dispersion liquid, and it is further important to secure crystal stability in the photosensitive layer for a long period of time against environmental conditions and the like.

[0011]

SUMMARY OF THE INVENTION It is an object of the present invention to provide an electrophotographic photosensitive member which overcomes the above problems and which has high sensitivity and is useful for a high speed printer, a high speed digital copying machine or a high speed facsimile.

Another object of the present invention is to provide an electrophotographic photosensitive member which has a small change in sensitivity characteristics with respect to humidity fluctuations.

Another object of the present invention is to obtain an electrophotographic photosensitive member having stable characteristics upon repeated use.

A further object of the present invention is to obtain an electrophotographic photosensitive member which is excellent in production stability and has little characteristic fluctuation.

[0015]

The above-mentioned object of the present invention is Cu-
An electrophotographic photoreceptor using crystalline titanyl phthalocyanine having a maximum peak at 27.2 ± 0.2 ° of Bragg angle 2θ in an X-ray diffraction spectrum for kα ray as a carrier-generating substance, preferably in a dispersion or in a photosensitive layer, preferably titanyl. -OH, -CO in the same layer as phthalocyanine
OH, -NHR, -NH _2, to -SH (where R represents a substituted or unsubstituted alkyl group) non-aromatic cyclic compound, 100 parts by weight of titanyl phthalocyanine having at least one as a substituent of the In the range of 0.1 to 1000 parts by weight, more preferably 1 to 500 parts by weight.

As a result of repeated studies by the inventors for improving the environment resistance property, particularly stability against humidity, when the specific crystal type titanyl phthalocyanine used in the present invention is used as a carrier generating substance, the carrier generating layer is used. It was found that the coexistence of a specific substance can significantly reduce the change in the sensitivity characteristic with respect to humidity fluctuation. Moreover, it has been found that the above-mentioned photoconductor also reduces changes in charging characteristics and sensitivity characteristics at the time of repeated use.

Further, the crystal stability over a long period of time has been earnestly studied, and it has been found that the specific crystal of titanyl phthalocyanine used in the present invention is significantly improved in the presence of the substance having the above-mentioned characteristics. The present invention has been constructed based on these findings.

The chemical structure of titanyl phthalocyanine used in the present invention is represented by the following general formula [I].

[0019]

[Chemical 1]

The X-ray diffraction spectrum is measured under the following conditions, and the peak here is a protrusion having a distinct acute angle different from noise.

X-ray tube Cu voltage 40.0 KV current 100 mA start angle 6.0 deg. Stop angle 35.0 deg. Step angle 0.02 deg. Measurement time 0.50 sec. Various methods can be used for synthesizing the titanyl phthalocyanine used in the present invention, but typically, it can be synthesized according to the following reaction formula (1) or (2).

[0022]

[Chemical 2]

In the formula, R _{1 to} R ₄ represent a leaving group.

The titanyl phthalocyanine obtained as described above can be converted into the crystal form used in the present invention by the following treatment.

For example, titanyl phthalocyanine of any crystal form is dissolved in concentrated sulfuric acid, the sulfuric acid solution is poured into water, and the precipitated crystals are collected by filtration. By this operation, titanyl phthalocyanine is converted into an amorphous state.

Next, the crystalline form used in the present invention can be obtained by treating this amorphous titanyl phthalocyanine with a specific organic solvent in the presence of water. As a specific example of such a method, for example, JP-A-3-35
Examples described in No. 245 can be given.

The non-aromatic cyclic compound used together with these titanyl phthalocyanines is a cyclic compound having no aromaticity, and examples thereof include non-aromatic monocyclic or condensed polycyclic hydrocarbons. However, these cyclic compounds may contain a hetero atom in the ring. In general, those having aromaticity have good crystallinity, and the effects of the non-aromatic cyclic compound of the present invention were not observed. Both of these non-aromatic cyclic compounds _{-OH, -COOH, -NHR, -NH 2} , -SH
It has at least 1 sort (s) as a substituent. Here, R represents a substituted or unsubstituted alkyl group.

Specific examples of such a compound include the following compounds.

[0029]

[Chemical 3]

[0030]

[Chemical 4]

[0031]

[Chemical 5]

These non-aromatic cyclic compounds are used in the range of 0.1 to 1000 parts by weight based on 100 parts by weight of titanyl phthalocyanine. If less than this, the effect is insufficient,
On the other hand, if the amount is too large, the sensitivity characteristic of the photoreceptor is deteriorated.

In the electrophotographic photoreceptor of the present invention, other photoconductive substance may be used in combination with the above-mentioned titanyl phthalocyanine. Examples of other photoconductive substances include A, B, C, and amorphous having a crystal type different from the crystal type used in the present invention, a mixed crystal of titanyl phthalocyanine and other phthalocyanine, and a mixed crystal of titanyl phthalocyanine, and a metal-free metal. Each crystal form of phthalocyanine, various metal phthalocyanines represented by copper phthalocyanine, naphthalocyanine, other porphyrin derivatives, azo compounds, polycyclic quinone compounds represented by dibromoanthanthrone, eutectic complexes of pyrylium compounds and pyrylium compounds, Squarium compounds and the like can be mentioned.

Next, the electrophotographic photoreceptor of the present invention may be used in combination with a carrier transport material. As the carrier-transporting substance, various ones can be used, but as a representative one, for example, a compound having a nitrogen-containing heterocyclic nucleus represented by oxazole, oxadiazole, thiazole, thiadiazole, imidazole, and the like, and a condensed ring nucleus thereof, Polyarylalkane compounds, pyrazoline compounds, hydrazine compounds, triarylamine compounds, styryl compounds, polis (bis) styryl compounds, styryltriphenylamine compounds, β-phenylstyryltriphenylamine compounds, Examples thereof include a butadiene-based compound, a hexatriene-based compound, a carbazole-based compound, and a condensed polycyclic compound. Specific examples of the carrier-transporting substance include the carrier-transporting substances described in JP-A-61-107356. The structures of particularly representative ones are shown below.

[0035]

[Chemical 6]

[0036]

[Chemical 7]

[0037]

[Chemical 8]

[0038]

[Chemical 9]

[0039]

[Chemical 10]

[0040]

[Chemical 11]

Various forms of the photoconductor are known. The photoconductor of the present invention may take any of these forms, but it is preferable to use a laminated or dispersed function-separated photoconductor. In this case, the configuration is usually as shown in FIGS. In the layer structure shown in FIG. 1A, a carrier generation layer 2 is formed on a conductive support 1, a carrier transport layer 3 is laminated on the carrier generation layer 2, and a photosensitive layer 4 is formed. ) Is these carrier generation layer 2 and carrier transport layer 3
To form a photosensitive layer 4 '. FIG. 3C shows an intermediate layer 5 provided between the photosensitive layer 4 and the conductive support 1 having the layer structure shown in FIG. The layer structure of FIG. 5 (5) is one in which a photosensitive layer 4 ″ containing a carrier generating substance 6 and a carrier transporting substance 7 is formed. Intermediate layer 5 between 1 and
Is provided. In the structure shown in FIG. 1, a protective layer may be further provided on the outermost layer.

In forming the photosensitive layer, it is effective to apply a solution in which the carrier-generating substance or the carrier-transporting substance is dissolved alone or together with a binder or an additive. However, since the solubility of the carrier-generating substance is generally low, in such a case, the carrier-generating substance is treated with an ultrasonic disperser,
A method of applying a liquid in which fine particles are dispersed in an appropriate dispersion medium using a dispersing device such as a ball mill, a sand mill, a homomixer, etc. is effective. In this case, the binder and additives are usually used by adding them to the dispersion liquid.

A wide variety of solvents or dispersion media can be used for forming the photosensitive layer. For example, butylamine, ethylenediamine, N, N-dimethylformamide, acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 4-methoxy-4-methyl-2-pentanone, tetrahydrofuran, dioxane, ethyl acetate, butyl acetate,
Acetic acid-t-butyl, methyl cellosolve, ethyl cellosolve, butyl cellosolve, ethylene glycol dimethyl ether, toluene, xylene, acetophenone, chloroform, dichloromethane, dichloroethane, trichloroethane, methanol, ethanol, propanol, butanol and the like can be mentioned.

When a binder is used for forming the carrier generating layer or the carrier transporting layer, any binder can be selected, but a high molecular polymer having hydrophobicity and film forming ability is particularly desirable. Examples of such a polymer include the following,
It is not limited to these. Polycarbonate Polycarbonate Z Resin Acrylic Resin Methacrylic Resin Polyvinyl Chloride Polyvinylidene Chloride Polystyrene Styrene-Butadiene Copolymer Polyvinyl Acetate Polyvinyl Formal Polyvinyl Butyral Polyvinyl Acetal Polyvinylcarbazole Styrene-Alkyd Resin Silicone Resin Silicone-Alkyd Resin Silicone-Butylal Resin Polyester Polyurethane Polyamide Polyurethane Epoxy Resin Phenolic resin Vinylidene chloride-Acrylonitrile copolymer Vinyl chloride-Vinyl acetate copolymer Vinyl chloride-Vinyl acetate-Maleic anhydride copolymer The ratio of the carrier generating substance to the binder is preferably 10 to 600% by weight, and further 50 It is desirable to set it to 400% by weight. The ratio of carrier transport material to binder
It is desirable to be 10 to 500% by weight. The thickness of the carrier generation layer is 0.01 to 20 μm, more preferably 0.05 to 5 μm. The thickness of the carrier transport layer is 1 to 100 μm, more preferably 5 to 30 μm.

The above-mentioned photosensitive layer may contain an electron accepting substance for the purpose of improving sensitivity, reducing residual potential, or reducing fatigue during repeated use. Examples of such an electron accepting substance include succinic anhydride, maleic anhydride, dibromosuccinic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 3-nitrophthalic anhydride and 4-nitrophthalic anhydride. Acid, pyromellitic dianhydride, mellitic dianhydride, tetracyanoethylene, tetracyanoquinodimethane, o-dinitrobenzene, m-dinitrobenzene, 1,3,5-trinitrobenzene, p-nitrobenzonitrile, picryl chloride, Quinone chlorimide, chloranil, bromanil, dichlorodicyano-p-benzoquinone, anthraquinone, dinitroanthraquinone, 9-fluorenylidene malononitrile, polynitro-9-fluorenylidene malononitrile, picric acid, o-nitrobenzoic acid, p- Nitrobenzoic acid, 3,5-dinitrobenzoic acid, pentafluorobenzoic acid Acid, 5-nitro salicylic acid, 3,5-dinitrosalicylic acid, phthalic acid, mellitic acid, and larger compounds of other electron affinity. The addition ratio of the electron accepting substance is 0.0 with respect to 100 by weight of the carrier generating substance.
It is preferably 1 to 200, more preferably 0.1 to 100.

Further, in the above-mentioned photosensitive layer, storability, durability,
For the purpose of improving the resistance to the environment, a deterioration inhibitor such as an antioxidant or a light stabilizer can be contained. Examples of compounds used for such purpose include chromanol derivatives such as tocopherol and its etherified or esterified compounds, polyarylalkane compounds,
Hydroquinone derivatives and mono- and dietherified compounds thereof, benzophenone derivatives, benzotriazole derivatives, thioether compounds, phosphonic acid esters, phosphorous acid esters, phenylenediamine derivatives, phenol compounds, hindered phenol compounds, linear amine compounds,
Cyclic amine compounds and hindered amine compounds are effective. Specific examples of particularly effective compounds include "IRGANOX
"1010", "IRGANOX 565" (manufactured by Ciba-Geigy), "Sumilyzer BHT", "Sumilyzer MDP" (manufactured by Sumitomo Chemical Co., Ltd.)
Hindered phenolic compounds such as "Sanol LS-262
6 ”,“ Sanol LS-622LD ”(manufactured by Sankyo Co., Ltd.) and the like.

As the binder used for the intermediate layer, the protective layer and the like, those mentioned above for the carrier generating layer and the carrier transporting layer can be used. In addition, nylon resin, ethylene-vinyl acetate copolymer, Ethylene resins such as ethylene-vinyl acetate-maleic anhydride copolymer and ethylene-vinyl acetate-methacrylic acid copolymer, polyvinyl alcohol, and cellulose derivatives are effective.
Further, a curable binder utilizing heat curing or chemical curing of melamine, epoxy, isocyanate or the like can be used.

As the conductive support, a metal plate or a metal drum may be used, and a conductive polymer, a conductive compound such as indium oxide, or a thin layer of a metal such as aluminum or palladium may be applied, vapor deposited, laminated or the like. Therefore, the one provided on a substrate such as paper or plastic film can be used.

[0049]

EXAMPLES The present invention will be described in detail with reference to examples.

Example 1 1 part by weight of titanyl phthalocyanine having peaks at 9.5 °, 24.1 °, and 27.2 ° of Bragg angle 2θ in FIG. 2, 100 parts by weight of methyl isopropyl ketone, and further 0.5 parts by weight of exemplary compound (4) of the present invention. Was added and dispersed using a sand mill. After a part of the obtained dispersion liquid was evaporated to dryness, the X-ray diffraction spectrum was measured and it was as shown in FIG. On the other hand, a 0.3 μm-thick undercoating layer made of polyamide resin “CM8000” (manufactured by Toray Industries, Inc.) was formed on a polyester base on which aluminum was vapor-deposited by a wire bar coating method, and then the obtained dispersion was coated with a wire bar to form a thick layer. The carrier generation layer has a thickness of 0.2 μm. Next, 1 part by weight of carrier-transporting substance (21), 1.5 parts by weight of polycarbonate resin "Iupilon Z-200" (manufactured by Mitsubishi Gas Chemical Co., Inc.) and a small amount of silicone oil "KF-54" (manufactured by Shin-Etsu Chemical Co., Ltd.) 1,2- Dichloroethane 8
The solution dissolved in parts by weight was blade-coated to form a carrier transport layer having a thickness of 20 μm. The photoreceptor thus obtained is referred to as Sample 1.

Examples 2 to 10 In Example 1, instead of the exemplified compound (4) of the present invention, exemplified compounds (1), (5), (8), (12), (15),
Example 1 except that (16), (33), (35) and (36) were used
A photoreceptor of the present invention was obtained in the same manner as. This is sample 2
Set to ~ 10. The X-ray diffraction spectrum measured after dispersion was the same as in Example 1, and no change in the crystalline state was observed.

Comparative Example (1) A comparative photoconductor was obtained in the same manner as in Example 1 except that the exemplified compound (4) of the present invention was omitted. This is designated as Comparative Sample (1). An X-ray diffraction spectrum measured by evaporating and drying a part of the obtained dispersion liquid is shown in FIG. A slight peak is seen at 26.2 ° of the Bragg angle 2θ, indicating that the crystalline state has changed.

Comparative Examples (2) to (6) The same as Example 1 except that the following compounds (1) to (5) were used in place of the non-aromatic cyclic compound (4) of the present invention in Example 1. Similarly, a comparative photoconductor was obtained. These are designated as comparative samples (2) to (6), respectively.

[0054]

[Chemical 12]

Comparative Example (7) In Example 1, the amount of the exemplified compound (4) of the present invention was changed to 12
A comparative photoconductor was obtained in the same manner as in Example 1 except that the parts by weight were used. This is designated as Comparative Sample (7).

Comparative Example (8) In Example 1, the amount of the exemplified compound (4) of the present invention was adjusted to 0.
A comparative photoconductor was obtained in the same manner as in Example 1 except that the weight part was changed. This is designated as Comparative Sample (8).

Example 11 1 part by weight of titanyl phthalocyanine having peaks at 9.5 °, 24.1 °, and 27.2 ° of Bragg angle 2θ in FIG. 2, 100 parts by weight of methyl ethyl ketone, 1 part by weight of polyvinyl butyral resin, and the exemplified compound of the present invention ( 4) 0.5 part by weight was added and dispersed using a ball mill. After a part of the obtained dispersion liquid was evaporated to dryness, the X-ray diffraction spectrum was measured and it was as shown in FIG.

On the other hand, an undercoat layer having a thickness of 0.3 μm made of polyamide resin “CM8000” (manufactured by Toray Industries, Inc.) was formed on a polyester base on which aluminum was vapor-deposited by a wire bar coating method, and then the obtained dispersion was coated with a wire bar. Then thickness
The carrier generation layer has a thickness of 0.2 μm. Next, 1 part by weight of carrier-transporting substance (21), 1.5 parts by weight of polycarbonate resin "Iupilon Z-200" (manufactured by Mitsubishi Gas Chemical Co., Inc.) and a small amount of silicone oil "KF-54" (manufactured by Shin-Etsu Chemical Co., Ltd.) 1,2-
A solution dissolved in 8 parts by weight of dichloroethane was blade-coated to form a carrier transport layer having a thickness of 20 μm. The photoconductor thus obtained is referred to as Sample 11.

Example 12 A photoreceptor of the present invention was obtained in the same manner as in Example 11 except that a silicone resin was used instead of the polyvinyl butyral resin in Example 11. This is sample 12.

Example 13 A photoreceptor of the present invention was obtained in the same manner as in Example 11 except that a silicone-butyral resin was used in place of the polyvinyl butyral resin in Example 11. This is sample 13.

Example 14 A photoreceptor of the present invention was obtained in the same manner as in Example 11 except that cyclohexanone was used in place of methyl ethyl ketone and polycarbonate Z resin was used in place of polyvinyl butyral resin. This is sample 14.

Comparative Examples (9) to (12) Comparative photoconductors were obtained in the same manner as in Examples 11 to 14 except that the exemplified compounds of the present invention were omitted. These are designated as comparative samples (9) to (12).

Evaluation 1 The obtained sample was subjected to “Koni” in an environment of 20 ° C. and 50% RH.
ca 9028 "(manufactured by Konica Corp., a semiconductor laser light source used) is mounted on a modified machine, to adjust the grid voltage V _G to -750 V, the potential V _L of the exposed portion at the time of light irradiation of the non-exposed portion potential V _H and 0.7mv
Was measured. Then, the sample was transferred to an environment of 10 ° C. and 20% RH and sufficiently adapted to the environment, and then V _H and V _L were measured under the above-mentioned conditions. In addition, V _H and V _L after repeated use of 10,000 prints in an environment of 10 ° C. and 20% RH were also measured.

Evaluation 2 The sample was also left in an atmosphere of 55 ° C. and 80% RH for one week, then mounted on a modified machine of “Konica 9028” under the environment of 20 ° C. and 50% RH, and V _H , V _L Was measured.

The evaluation results are shown in Table 1. It can be seen that the non-aromatic cyclic compound of the present invention exhibits remarkable effects on fluctuations in humidity, reduction in changes in photoreceptor characteristics due to repeated use, and stabilization of dispersion liquid and photoreceptor.

[0066]

[Table 1]

Example 15 Similar to Example 1 except that the titanyl phthalocyanine in Example 1 was replaced with titanyl phthalocyanine showing an X-ray diffraction spectrum having peaks at Bragg angles 2θ of 27.2 °, 24.1 ° and 9.0 ° in FIG. Thus, a photoconductor of the present invention was obtained.
This is sample 15.

Comparative Example (13) A comparative photoconductor was obtained in the same manner as in Example 15, except that the exemplified compound (4) in the present invention was omitted. This is designated as a comparative sample (13).

Sample 15 and comparative sample (13) were evaluated according to the methods of Evaluations 1 and 2. The results are shown in Table 2.

[0070]

[Table 2]

It is confirmed that the system of the present invention exhibits excellent properties.

[0072]

According to the constitution of the present invention, the stability of the dispersion liquid and the photoconductor can be remarkably improved.

[Brief description of drawings]

FIG. 1 is a sectional view of a photoconductor of the present invention.

FIG. 2 is an X-ray diffraction spectrum diagram of titanyl phthalocyanine used in the present invention.

FIG. 3 is an X-ray diffraction spectrum of the titanyl phthalocyanine obtained in Example 1.

FIG. 4 is an X-ray diffraction spectrum diagram of the titanyl phthalocyanine obtained in Comparative Example (1).

FIG. 5: X of titanyl phthalocyanine used in Example 15
Line diffraction spectrum diagram.

[Explanation of symbols]

 1 Conductive Support 2 Carrier Generation Layer 3 Carrier Transport Layer 4 Photosensitive Layer 5 Intermediate Layer 6 Carrier Generation Material 7 Carrier Transport Material

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Yoshihide Fujimaki 2970 Ishikawa-cho, Hachioji-shi, Tokyo Konica stock company (72) Inventor Kazumasa Watanabe 1-chome, Sakura-cho, Hino-shi, Tokyo Konica Stock Company In-house

Claims (3)

[Claims] 1. A titanyl phthalocyanine having a maximum peak at a Bragg angle 2θ of 27.2 ± 0.2 ° with respect to Cu-Kα characteristic X-rays (wavelength 1.541Å) is contained, and -OH and -COO are contained.
H, -NHR, -NH _2, to -SH (wherein R represents a substituted or unsubstituted alkyl group) non-aromatic cyclic compound, 100 parts by weight of titanyl phthalocyanine having at least one as a substituent of the An electrophotographic photosensitive member characterized by being contained in an amount of 0.1 to 1000 parts by weight. 2. The titanyl phthalocyanine has a Bragg angle of 2θ of 9.5 ± with respect to Cu-Kα characteristic X-rays (wavelength: 1.541Å).
The electrophotographic photosensitive member according to claim 1, which is a crystal having peaks at 0.2 °, 24.1 ± 0.2 °, and 27.2 ± 0.2 °. 3. Titanyl phthalocyanine has a Bragg angle of 2θ of 9.0 ± with respect to Cu-Kα characteristic X-rays (wavelength: 1.541Å).
The electrophotographic photosensitive member according to claim 1, which is a crystal having peaks at 0.2 °, 24.1 ± 0.2 °, and 27.2 ± 0.2 °.