JPH0560858B2 - - Google Patents

Description

[Detailed description of the invention] [Industrial application field]

The present invention relates to electrophotographic photoreceptors, and more particularly to improvements in organic photoconductive electrophotographic photoreceptors.

[Prior art]

In the Carlson method electrophotographic copying machine,
After the surface of the photoreceptor is charged, an electrostatic latent image is formed by exposure, the electrostatic latent image is developed with toner, and the visible image is then transferred and fixed onto paper or the like. At the same time, the photoreceptor is subjected to removal of adhered toner, neutralization of static electricity, and surface cleaning, and is used repeatedly over a long period of time. Therefore, as an electrophotographic photoreceptor, it is of course necessary to have electrophotographic properties such as good charging characteristics and sensitivity, and low dark decay, but also printing durability, abrasion resistance, moisture resistance, etc. during repeated use. It is also required to have good physical properties and resistance to ozone generated during corona discharge, ultraviolet rays during exposure, etc. (environmental resistance). Conventionally, as electrophotographic photoreceptors, inorganic photoreceptors having a photosensitive layer mainly composed of an inorganic photoconductive substance such as selenium, zinc oxide, or cadmium sulfide have been widely used. On the other hand, the use of various organic photoconductive substances as materials for photosensitive layers of electrophotographic photoreceptors has been actively developed and researched in recent years. For example, in Japanese Patent Publication No. 50-10496, poly-N
- describes an organic photoreceptor having a photosensitive layer containing vinylcarbazole and 2,4,7,-trinitro-9-fluorenone. However, this photoreceptor is not necessarily satisfactory in sensitivity and durability. In order to improve these drawbacks, attempts have been made to develop organic photoreceptors with high sensitivity and durability by assigning the charge generation function and charge transport function to different substances in the photosensitive layer. ing. In such so-called function-separated type electrophotographic photoreceptors, substances that exhibit each function can be selected from a wide range of materials, so it is relatively easy to produce electrophotographic photoreceptors with arbitrary characteristics. Is possible. Many substances have been proposed as charge-generating substances that are effective for such functionally separated electrophotographic photoreceptors. Examples of using inorganic substances include, for example, as described in Japanese Patent Publication No. 16198/1983,
There is amorphous selenium. This is combined with an organic charge transport material. In addition, many electrophotographic photoreceptors using organic dyes or organic pigments as carrier generating substances have been proposed. 22834
No. 54-79632, No. 56-116040, and other publications. By the way, known photoreceptors using organic photoconductive substances are generally used for negative charging. The reason for this is that when negative charging is used, the mobility of holes among the charges is large, which is advantageous in terms of photosensitivity and the like. However, it has been found that using such negative charging causes the following problems. That is, the first problem is that ozone is likely to be generated in the atmosphere during negative charging by the charger, worsening the environmental conditions. Another problem is that positive polarity toner is required for development of negatively charged photoreceptors, but positive polarity toner is difficult to manufacture due to the triboelectrification system for ferromagnetic charged particles. . Therefore, it has been proposed to use a positively charged photoreceptor using an organic photoconductive substance. for example,
In the case of a positive charging photoreceptor in which a charge transport layer is laminated on a charge generation layer and the charge transport layer is formed of a substance with a high electron transport ability, the charge transport layer contains trinitrofluorenone, etc., but this substance does not emit light. It is unsuitable because it is cancerous. On the other hand, a positive charging photoreceptor may be considered in which a charge generation layer is laminated on a charge transport layer with a large hole transport ability, but this has poor printing durability due to the presence of a very thin charge generation layer on the surface side. This is not a practical layer structure. In addition, as a photoreceptor for positive charging, the U.S. Patent No.
No. 3,615,414 discloses a material containing a thiapyrylium salt (charge generating substance) so as to form a eutectic complex with polycarbonate (binder resin). However, with this known photoreceptor,
The disadvantage is that the memory phenomenon is large and ghosts are likely to occur. U.S. Patent No. 3,357,989 also discloses a photoreceptor containing phthalocyanine, but the characteristics of phthalocyanine change depending on the crystal form, and the crystal form must be strictly controlled. Furthermore, it lacks short wavelength sensitivity and has a large memory phenomenon, making it unsuitable for copying machines that use light sources in the visible wavelength range. Due to the above-mentioned circumstances, conventionally, it has been difficult to use a photoreceptor using an organic photoconductive substance for positive charging, and for this reason, it has been used exclusively for negative charging.

[Purpose of the invention]

An object of the present invention is to provide an organic photoconductive electrophotographic photoreceptor that can be used for positive charging, has good sensitivity, has excellent scratch resistance and ozone resistance, and is durable. be.

[Configuration and effects of the invention]

The above-mentioned object of the present invention is to provide an electrophotographic photoreceptor in which a photosensitive layer containing a charge generating substance and a charge transporting substance as main components is provided on a conductive support, and the photosensitive layer contains a compound represented by the following general formula. This was achieved by forcing. general formula In the formula, R represents a substituted or unsubstituted amino group. Ozone deterioration of the photoreceptor is caused by repeatedly applied corona discharge, but it is also thought to be enhanced by singlet oxygen generated by exposure.
The degree of ozone oxidation varies depending on the structure of the photosensitive layer of the photoreceptor, the types of charge-generating substances and charge-transporting substances, etc., but charge-transporting substances are more susceptible to oxidation, especially organic photoconductive materials. When using sexual substances, the consequences are extremely large. As a result of extensive research into improving ozone deterioration (particularly potential drop) of photoreceptors, the present inventors found that a specific 1,2-dihydroquinoline derivative represented by the above general formula in the photosensitive layer significantly prevents ozone oxidation. The present inventors have discovered that the present invention also contributes to improvements in other electrophotographic properties and physical properties. The present invention will be explained in more detail below. The 1,2-dihydroquinoline derivative used in the present invention is characterized by a so-called hindered amine-like structure having two methyl groups at the 2-position and a methyl group at the 4-position, and a substituted or unsubstituted amino group at the 6-position. is not particularly restricted. For example, amino group,
Examples include ethylamino group, diethylamino group, acetamino group, and benzoylamino group. Typical specific examples of the compounds of the present invention are shown below, but the compounds used in the present invention are not limited thereto.

[Table] The amount of the compound represented by the above general formula used in the present invention (hereinafter referred to as the compound of the present invention) varies depending on the layer structure of the photoreceptor, the type of charge transport material, etc. 0.1 to 100% by weight, preferably 1 to 50% by weight, based on the transported substance;
It is particularly preferably used in a range of 5 to 25% by weight. Next, the structure of the photoreceptor of the present invention will be explained with reference to the drawings. For example, as shown in FIG. 1, the photoreceptor of the present invention has a charge generating material 5 (hereinafter referred to as
CGM) and a charge generating layer 2 (hereinafter referred to as CGL) containing a binder resin as necessary.
) as the lower layer, and a charge transport material 6
(hereinafter sometimes referred to as CTM) and a charge transport layer 3 (hereinafter referred to as CTM) containing a binder resin as necessary.
As shown in FIG. 2, a photosensitive layer 4 is provided in a laminated structure with CTL3 as the lower layer and CGL2 as the upper layer on the support 1, as shown in FIG. and the third
As shown in the figure, a photosensitive layer 4 having a single layer structure containing CGL, CTM and, if necessary, a binder resin is provided on a support 1, and the like. In addition, the upper layer CGL has the same layer configuration as shown in Figure 2.
Both CGM and CTM may be contained, a protective layer (OCL) may be provided on the photosensitive layer, and an intermediate layer may be provided between the support and the photosensitive layer. An example is shown in FIG. That is, support 1
CTL3 and CGM5 containing CTM6a and binder resin, with intermediate layer 7 provided thereon;
CGL containing CTM6b and binder resin
This photoreceptor has a photoreceptor layer 4 in which the photoreceptor 2 is laminated, and a protective layer 8 whose main component is a binder is further provided. The compound of the present invention comprises CGL, which constitutes the photoreceptor;
It may be contained in any of the CTL, single-layer photosensitive layer, or OCL, or may be contained in multiple layers. The effect of the present invention is more pronounced in CGL.
This is a photoreceptor with a laminated structure in which CTL is an upper layer and CTL is a lower layer. Next, as the charge generating substance suitable for the present invention, any of inorganic pigments and organic dyes can be used as long as it absorbs visible light and generates free charges. In addition to inorganic pigments such as amorphous selenium, trigonal selenium, selenium-arsenic alloy, selenium-tellurium alloy, cadmium sulfide, cadmium selenide, cadmium selenide sulfide, mercury sulfide, lead oxide, lead sulfide, the following representative examples Organic pigments such as those shown may also be used. (1) Azo pigments such as monoazo pigments, polyazo pigments, metal complex azo pigments, pyrazolone azo pigments, stilbene azo and thiazole azo pigments. (2) Perylene pigments such as perylene anhydride and perylene imide. (3) Anthraquinone or polycyclic quinone pigments such as anthraquinone derivatives, anthanthrone derivatives, dibenzpyrenequinone derivatives, pyrantrone derivatives, violanthrone derivatives, and isoviolanthrone derivatives (4) Indigoid pigments such as indigo derivatives and thioindigo derivatives (5) Phthalocyanine pigments such as metal phthalocyanine and metal-free phthalocyanine (6) Carbonium pigments such as diphenylmethane pigment, triphenylmethane pigment, xanthene pigment and acridine pigment (7) Quinone imide such as azine pigment, oxazine pigment and thiazine pigment Cyanine pigments and azomethine pigments (9) Quinoline pigments (10) Nitro pigments (11) Nitroso pigments (12) Benzoquinone and naphthoquinone pigments (13) Naphthalimide pigments (14) ) Perinone pigments such as bisbezimidazole derivatives Various azo pigments with electron-withdrawing groups are used because of their good electrophotographic properties such as sensitivity, memory phenomenon, and residual potential, but polycyclic quinones are preferred due to their good ozone resistance. pigments are most preferred. Although the details are unknown, this is probably because the azo group is susceptible to ozone oxidation and the electrophotographic properties deteriorate, whereas polycyclic quinones are inert to ozone. As the azo pigment used in the present invention,
For example, there are compounds shown in the following exemplified compound groups [] to [].

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[Table] Furthermore, the following exemplified compound groups [] to [] consisting of polycyclic quinone pigments can be most preferably used as CGM.

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[Table] Next, there are no particular limitations on charge transport substances that can be used in the present invention, but examples include oxazole derivatives, oxadiazole derivatives, thiazole derivatives, thiadiazole derivatives, triazole derivatives, imidazole derivatives, imidazolone derivatives,
Imidazolidine derivatives, bisimidazolidine derivatives, styryl compounds, hydrazone compounds, pyrazoline derivatives, oxazolone derivatives, benzothiazole derivatives, benzimidazole derivatives, quinazoline derivatives, benzofuran derivatives, acridine derivatives, phenazine derivatives, aminostilbene derivatives, poly-N-vinyl Carbazole, poly-1-
It may be vinylpyrene, poly-9-vinylanthracene, etc. However, it is preferable to use a CTM that has an excellent ability to transport holes generated during light irradiation to the support side and is suitable for combination with the carrier generating substance. Examples of such CTM include the following exemplified compound group [] or [ ] is used.

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[Table] In addition, the following exemplified compound groups [XI] ~
Hydrazine compounds represented by [ ] can also be used.

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[Table] In addition, pyrazoline compounds shown in the exemplified compounds [] can also be used as CTMs.

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[Table] In addition, the following exemplified compound group as CTM []
Amino derivatives represented by can also be used.

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[Table] The layer structure of the photosensitive layer of the photoreceptor of the present invention has a laminated structure and a single layer structure as described above.
Either CTL, CGL, single layer photosensitive layer or OCL,
Alternatively, the plurality of layers may contain one or more electron-accepting substances for the purpose of improving sensitivity, reducing residual potential, or reducing fatigue during repeated use. Examples of electron-accepting substances that can be used in the photoreceptor of the present invention include succinic anhydride, maleic anhydride, dibromaleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride,
3-nitro-phthalic anhydride, 4-nitro-phthalic anhydride, pyromellitic anhydride, mellitic anhydride, tetracyanoethylene, tetracyanoquinodimethane,
o-dinitrobenzene, m-dinitrobenzene,
1,3,5,-trinitrobenzene, paranitrobenzonitrile, picryl chloride, quinone chlorimide, chloranil, brumanil, 2-methylnaphthoquinone, dichlorodicyanoparabenzoquinone, anthraquinone, dinitroanthraquinone, trinitrofluorenone, 9-fluorenylidene dicyanomethylenemalonodinitrile], polynitro-9-fluorenylidene-[dicyanomethylenemalonodinitrile], picric acid, o-nitrobenzoic acid, p-nitrobenzoic acid, 3,5-dinitrobenzoic acid, pentafluorobenzoic acid, 5 −
Examples include nitrosalicylic acid, 3,5-dinitrosalicylic acid, and phthalic acid. Examples of binder resins that can be used in the photosensitive layer in the present invention include polyethylene, polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin, epoxy resin, polyurethane resin, phenolic resin, polyester resin, alkyd resin, and polycarbonate resin. , addition polymerization resins such as silicone resins and melamine resins,
Polyaddition resins, polycondensation resins, and copolymer resins containing two or more repeating units of these resins, such as vinyl chloride-vinyl acetate copolymer resins, vinyl chloride-vinyl acetate-maleic anhydride In addition to insulating resins such as copolymer resins, polymeric organic semiconductors such as poly-N-vinylcarbazole may be used. Further, the intermediate layer functions as an adhesive layer or a barrier layer, and in addition to the binder resin, for example, polyvinyl alcohol, ethyl cellulose, carboxymethyl cellulose, vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-anhydrous Maleic acid copolymers, casein, N-alkoxymethylated nylon, starch, etc. are used. Next, the conductive support supporting the photosensitive layer may be a metal plate made of aluminum or nickel, a metal drum or metal foil, a plastic film deposited with aluminum, tin oxide, indium oxide, etc., or paper coated with a conductive substance. , a film or drum of plastic or the like can be used. CGL can be provided by vacuum-depositing the above-mentioned CGM onto the support, or by applying a solution or dispersion of CGM alone or together with a suitable binder resin in a suitable solvent, and drying it. When CGL is formed by dispersing the CGM, the CGM is preferably in the form of powder having an average particle size of 2 μm or less, preferably 1 μm or less. That is, if the particle size is too large, dispersion in the layer will be poor, and some of the particles will protrude from the surface, resulting in poor surface smoothness. Toner particles tend to adhere to the toner, causing a toner filming phenomenon. However, if the above particle size is too small, it tends to aggregate, which increases the resistance of the layer, increases crystal defects and reduces sensitivity and repeatability, or there is a limit to miniaturization. Lower limit of diameter
It is desirable to set it to 0.01 μm. CGL can be provided by the following method. That is, this is a method in which the CGM described above is made into fine particles in a dispersion medium using a ball mill, a homomixer, etc., a binder resin is added, and a dispersion obtained by mixing and dispersing is applied. When the particles are dispersed under the action of ultrasound in this method, uniform dispersion is possible. Solvents used in the formation of CGL include, for example, N,N-dimethylformamide, benzene, toluene, xylene, monochlorobenzene, 1,2
-dichloroethane, dichloromethane, 1,1,2
-Trichloroethane, tetrahydrofuran, methyl ethyl ketone, ethyl acetate, butyl acetate, and the like. CGM per 100 weight of binder resin in CGL
The amount is 20 to 200 parts by weight, preferably 25 to 100 parts by weight. If the CGM is less than this, the photosensitivity will be low and the residual potential will increase, and if it is more than this, the dark decay will increase and the acceptance potential will decrease. The thickness of the CGL formed in the above manner is
In the case of a configuration for positive charging, it is preferably 1 to 10 μm, particularly preferably 3 to 7 μm, and in the case of a configuration for negative charging, it is preferably 0.01 to 10 μm, particularly preferably 0.1
~3 μm. In addition, CTL is prepared by applying the above-mentioned CTM in the same manner as the above-mentioned CGL (i.e., applying it alone or by dissolving and dispersing it together with the above-mentioned binder resin).
dry). CTM per 100 parts by weight of binder resin in CTL
is 20 to 200 parts by weight, preferably 30 to 150 parts by weight. If the CTM content is less than this, the photosensitivity will be poor and the residual potential will tend to be high, and if it is more than this, the solvent solubility will be poor. The thickness of the CTM to be formed is preferably 5 to 5.
50 μm, particularly preferably 5 to 30 μm. Also,
The film thickness ratio of CGL and CTL is preferably 1:(1 to 30). In the case of the single-layer structure, the proportion of CGM contained in the binder resin is 20 to 200 parts by weight, preferably 25 to 100 parts by weight, based on 100 parts by weight of the binder resin. If the CGM content is less than this, the photosensitivity will be low and the residual potential will increase, and if it is more than this, the dark decay and acceptance potential will decrease. Next, the ratio of CTM to binder resin is 20 parts by weight per 100 parts by weight of binder resin.
~200 parts by weight, preferably 30 to 150 parts by weight. If the CTM content is less than this, the photosensitivity will be poor and the residual potential will tend to be high, and if it is more than this, the solvent solubility will be poor. The weight ratio of CTM to CGM in the single-layer photosensitive layer is preferably 1:3 to 1:2. In the present invention, the protective layer provided as necessary has a volume resistivity of 10 ⁸ Ω・cm or more as a binder,
Preferably 10 ¹⁰ Ω・cm or more, more preferably
A transparent resin with a resistance of 10 ¹³ Ω・cm or more is used. Further, the binder contains at least 50% by weight of a resin that is cured by light or heat. Such resins that harden with light or heat include:
Examples include thermosetting acrylic resins, silicone resins, epoxy resins, urethane resins, urea resins, phenolic resins, polyester resins, alkyd resins, melamine resins, photocurable/cinnamic acid resins, and copolymerized or cocondensed resins thereof. , as well as photo- or thermosetting resins used in electrophotographic materials. If necessary, the protective layer may contain less than 50% by weight of a thermoplastic resin for the purpose of improving processability and physical properties (preventing cracks, imparting flexibility, etc.). Examples of such thermoplastic resins include polypropylene, acrylic resin, methacrylic resin, vinyl chloride resin, vinyl acetate resin,
Epoxy resin, butyral resin, polycarbonate resin, silicone resin, or copolymer resin thereof, such as vinyl chloride-vinyl acetate copolymer resin, vinyl chloride-vinyl acetate-maleic anhydride copolymer resin, poly-N-vinylcarbazole All of the thermoplastic resins used in electrophotographic materials, such as polymeric organic semiconductors and other electrophotographic materials, can be used. Further, the protective layer may contain an electron-accepting substance, and may also contain an ultraviolet absorber or the like for the purpose of protecting the CGM if necessary. Applied and dried by spray coating, blade coating, roll coating, etc. to a thickness of 2 μm or less, preferably
Formed to a layer thickness of 1 μm or less.

【Example】

EXAMPLES The present invention will be explained below with reference to Examples, but the embodiments of the present invention are not limited thereby. Example 1 A conductive support made of polyester film laminated with aluminum foil was coated with a layer of vinyl chloride-vinyl acetate-maleic anhydride copolymer (Eslec MF-10, manufactured by Sekisui Chemical Co., Ltd.).
An intermediate layer of 0.1 μm was formed. Next, CTM (-75)/polycarbonate resin (Panlite L-1250, manufactured by Teijin Chemicals) = 75/100
A 1,2-dichloroethane solution containing 16.5% by weight (weight ratio) was dip-coated onto the intermediate layer and dried to obtain a CTL with a thickness of 15 μm. Then, 4,10-dibromoanthrone(-3)/panlite L- was sublimated as CGM.
1250 = 50/100 (weight ratio) was ground in a ball mill for 24 hours, 1,2-dichloroethyne was added to make it 9% by weight, and the mixture was further dispersed in a ball mill for 24 hours.
CTM (-75) to 75 against Panlite L-1250
Weight% and compound (1) of the present invention relative to CTM
Added 10% by weight. Monochlorobenzene was added to this dispersion so that the ratio of monochlorobenzene/1,2-dichloroethane was 3/7 (volume ratio).
A photoreceptor of the present invention was obtained by forming a CGL of 5 μm and having a photosensitive layer having a laminated structure. Comparative Example 1 A comparative photoreceptor was obtained in the same manner as in Example 1 except that compound (1) in CGL was removed. Example 2 Compound (3) was substituted for compound (1) in Example 1.
A photoreceptor of the present invention was obtained in the same manner as in Example 1 except that . Example 3 A thermosetting acrylic-melamine-epoxy (1:1:1) resin was placed on a photoreceptor (same as the photoreceptor of Comparative Example 1) obtained by removing compound (1) from the CGL of Example 1.
Spray coating with a coating solution obtained by dissolving 1.55 parts by weight and 0.155 parts by weight of the compound (1) of the present invention in 100 parts by weight of a monochlorobenzene/1,1,2-trichloroethane (1/1 volume ratio) mixed solvent. , and dried to form a protective layer with a thickness of 1 μm to obtain a photoreceptor of the present invention. Example 4 A silicone hard coat primer PH91 was applied onto the photoconductor obtained by removing compound (1) from the CGL of Example 1.
(manufactured by Toshiba Silicon Co., Ltd.) is spray applied to a thickness of 0.1 μm, and then silicone hard coat guard is applied on top of that.
510 (manufactured by Toshiba Silicon Co., Ltd.) and compound (1) as a resin.
A solution added in an amount of 10 parts by weight per 100 parts by weight was spray-coated and dried to form a protective layer of 1 μm to obtain a photoreceptor of the present invention. Example 5 An intermediate layer exactly the same as in Example 1 was formed on a conductive support made of polyester film laminated with aluminum foil. Next, as a coating liquid for CTL, a solution obtained by dissolving butyral resin (Erex BX-1, manufactured by Sekisui Chemical Co., Ltd.) in methyl ethyl ketone so that 8% by weight and CTM (-75) by 6% by weight was applied onto the intermediate layer. was applied and dried to form a 10 μm thick CTL. Next, 0.2 g of CGM (-7) was pulverized for 30 minutes using a paint conditioner (Paint Conditioner, manufactured by Red Devil), and carbonate resin (Panlite L-1250, mentioned above) was mixed with 1,2-dichloroethane/1. , 1,2-trichloroethane mixed solvent
After adding 8.3g of a solution dissolved to a concentration of 0.5% by weight and dispersing for 3 minutes, polycarbonate resin, CTM (-75) and compound (1) were added to this, respectively.
Solution 19.1 obtained by dissolving in a mixed solvent of 1,2-dichloroethane/1,1,2-trichloroethane to give 3.3% by weight, 2.6% by weight and 0.26% by weight
g was added and dispersed for an additional 30 minutes. The thus obtained dispersion was spray-coated onto the CTL and dried to form a 5 μm thick CGL, thereby obtaining a photoreceptor according to the present invention having a photosensitive layer having a laminated structure. Comparative Example 2 A comparative photoreceptor was obtained in the same manner as in Example 5 except that compound (1) in CGL was removed. Example 6 Compound (3) was substituted for compound (1) in Example 5.
A photoreceptor of the present invention was obtained in the same manner as in Example 5 except that . Example 7 A protective layer containing the compound (1) used in Example 3 was provided on a photoreceptor (same as the photoreceptor of Comparative Example 2) obtained by removing compound (1) from the CGL of Example 5. A photoreceptor of the invention was obtained. Example 8 A protective layer containing the compound (1) used in Example 4 was provided on a photoreceptor obtained by removing compound (1) from the CGL of Example 5 to obtain a photoreceptor of the present invention. Example 9 An intermediate layer exactly the same as in Example 1 was formed on a polyester film on which aluminum was vapor-deposited. Next, 40 g of sublimed 4,10-dibromoanthrone (-3) was milled at 40 rpm in a porcelain ball mill.
Grind for 24 hours with Panlite L-1250 (mentioned above) 20
Add g and 1,2-dichloroethane 1300ml, and
It was dispersed for 24 hours to prepare a CGL coating solution. This was applied onto the intermediate layer to form a CGL with a film thickness of 1 μm. Next, CTM (-61) 7.5g, Panlite L-
A solution prepared by dissolving 10 g of 1250 and 0.75 g of compound (1) in 80 ml of 1,2-dichloroethane was applied onto the CGL to form a CTL having a thickness of 15 μm, thereby producing a photoreceptor of the present invention. Comparative Example 3 A comparative photoreceptor was obtained in the same manner as in Example 9 except that compound (1) in CTL was removed. Example 10 On a conductive support made of polyethylene terephthalate with a thickness of 100 μm and deposited with aluminum,
An intermediate layer exactly the same as in Example 1 was formed. Then bisazo compound (-7) as CGL
A dispersion in which 1.5 g of 1,2-dichloroethane/ethanolamine (1000/1 volume ratio) was dispersed in 100 ml of a mixed solvent using a ball mill for 8 hours was coated on the above intermediate layer and thoroughly dried to form a 0.3 μm thick CGL. Established. Then styryl compound (−43) as CTM
11.25g, 15g of Panlite L-1250 (above) and 1.125g of compound (1) in 100ml of 1,2-dichloroethane
A solution dissolved in the above was applied onto the CGL and sufficiently dried to form a CTL with a thickness of 15 μm, thereby producing a photoreceptor of the present invention. Comparative Example 4 A comparative photoreceptor was prepared in the same manner as in Example 10 except that compound (1) in CTL was removed. The ozone resistance of the 14 types of photoreceptors thus obtained was evaluated in the following manner. That is, an ozone generator (manufactured by Nippon Ozone Co., Ltd., 0-1-2
Using an ozone fatigue tester equipped with an ozone monitor (manufactured by Ebara Jitsugyo Co., Ltd., model EG-2001) and a photoreceptor mounted at an ozone concentration of 90 ppm, the following characteristic tests were conducted. In other words, a voltage of +6KV is applied for a positively charged photoreceptor, and -6KV is applied for a negatively charged photoreceptor, the photosensitive layer is charged by corona discharge for 5 seconds, and then left for 5 seconds (the potential at this time is set to the initial value). Then, the surface of the photosensitive layer was irradiated with light from a tungsten lamp with an illuminance of 14 lux, and this operation was repeated 100 times. Residual potential _VI after 100 cycles was measured, and ozone resistance was evaluated by _VI /Vo x 100 (%). We also measured the exposure amount E ⁶⁰⁰ ₁₀₀ (lux seconds) required to attenuate the initial potential from ±600V to ±100V. The larger the value of V _I /Vo×100 (%), the
It shows less ozone deterioration, and E ⁶⁰⁰ ₁₀₀ (The smaller the lux-second value, the more sensitive the photoreceptor is. The results are shown in the attached table.

[Table] As is clear from the table, by adding the compound of the present invention, the potential drop due to corona charging in the presence of ozone is significantly improved. Moreover,
It can be seen that the addition of the compound of the present invention causes almost no decrease in sensitivity.

[Brief explanation of the drawing]

1 to 4 are cross-sectional views of the photoreceptor of the present invention. DESCRIPTION OF SYMBOLS 1... Support, 2... Charge generation layer (CGL), 3... Charge transport layer (CTL), 4... Photosensitive layer, 5... Charge generation material (CGM), 6... Charge transport material (CTM), 7... Intermediate layer , 8...protective layer (OCL).

Claims (1)

[Scope of Claims] 1. An electrophotographic photoreceptor in which a photosensitive layer containing a charge generating substance and a charge transporting substance as main components is provided on a conductive support, in which a compound represented by the following general formula is incorporated in the photosensitive layer. An electrophotographic photoreceptor comprising: general formula [In the formula, R represents a substituted or unsubstituted amino group. ]