JP4119826B2 - Arylamine compound, and electrophotographic photoreceptor and image forming apparatus using the same - Google Patents

Description

The present invention is useful as a charge transporting material contained in the photosensitive layer of the electrophotographic photosensitive member, using a novel arylamine type compound, an electrophotographic photoreceptor and an image forming apparatus.

In recent years, electrophotographic technology has been widely used and applied not only in the field of copying machines but also in the fields of various printers and printing presses because of its immediacy and high quality images.
Photoconductors that are the core of electrophotographic technology have been used as conventional photoconductive materials for inorganic photoconductors such as selenium, arsenic-selenium alloys, cadmium sulfide, and zinc oxide. The use of a photoconductor using an organic photoconductive material having advantages such as easy and easy manufacture has become the mainstream.

  As a layer structure of the organic photoreceptor, a so-called single-layer type photoreceptor in which a charge generation material is dispersed in a binder resin and a so-called laminated type photoreceptor in which a charge generation layer and a charge transport layer are laminated are known. Multilayer photoconductors can provide highly sensitive and stable photoconductors by combining highly efficient charge generation materials and charge transport materials into separate layers and combining them optimally. It is often used because it is easy to adjust. Single layer type photoconductors are slightly inferior to multilayer photoconductors in terms of electrical characteristics, and material selectivity is narrow, but high resolution can be achieved by generating charges in the vicinity of the photoconductor surface. Since the image is not blurred, high printing durability can be achieved by increasing the film thickness. In addition, the single-layer type photosensitive member requires fewer coating processes, is advantageous for interference fringes and tube defects derived from a conductive substrate (support), and can be used with a low-priced substrate such as a non-cutting tube. It has the advantage that cost can be reduced.

In addition, since the electrophotographic photosensitive member is repeatedly used in an electrophotographic process, that is, a cycle of charging, exposure, development, transfer, cleaning, static elimination, and the like, it is deteriorated by various stresses during that time. Among them, strongly oxidizing ozone or NO _X that as the chemical degradation arising from a corona charger which is normally used as, for example, the charger is useless in the photosensitive layer - include giving di, if used repeatedly, the charging Deterioration in electrical stability such as increase in residual potential and increase in residual potential, and accompanying image defects may occur. These are largely derived from chemical deterioration of charge transport materials contained in the photosensitive layer in a large amount.

  Furthermore, with the recent increase in the speed of electrophotographic processes, higher sensitivity and faster response are essential. Of these, in order to achieve high sensitivity, it is necessary not only to optimize charge generation materials, but also to develop charge transport materials with good matching with them. For high-speed response, high mobility and exposure It is sometimes necessary to develop charge transport materials that exhibit a sufficiently low residual potential.

As conventional techniques, Patent Documents 1 to 5 and Non-Patent Document 1 describe various compounds contained as a charge transport material in a photosensitive layer of an electrophotographic photoreceptor.
However, the photoconductor using the benzidine compound group described in Patent Document 1 has a relatively low mobility, and there is a point to be improved in electric characteristics.
The benzidine compounds described in Patent Document 2 and Patent Document 3 have difficulties in solubility in a solvent and stability of a coating solution during production of a photoreceptor.
The photoreceptor using the benzidine compound described in Non-Patent Document 1 has difficulty in image characteristics during repeated image formation.
The photoreceptors using the p-phenylenediamine derivative group described in Patent Literature 4 and Patent Literature 5 have relatively large dark decay, and there is a possibility that fogging or the like may occur during actual use.

JP-A-3-225345 JP-A-6-214409 JP 2000-56490 A JP-A-4-182655 European Patent 314195 Electrophotographic Society Journal VOL30, No1, P16-21

  With the recent increase in the speed of electrophotographic processes, higher performance and faster response are essential. However, each of the above-described conventional techniques has a problem in achieving both the electric characteristics (low residual potential, high mobility, etc.) and solubility of the charge transport material, and a new charge transport material that is balanced in both characteristics. Was demanded. Even if this requirement is satisfied, there are many problems in image characteristics, and a balanced material is also required in this respect.

The present invention has been made in view of the above problems, and an object can improve the electrical characteristics and image characteristics of the electrophotographic photosensitive member, and, had use excellent charge transporting material in solubility, The object is to provide an electrophotographic photosensitive member and an image forming apparatus.

  As a result of intensive studies to solve the above problems, the present inventors have found that an arylamine compound having a specific structural formula is excellent in solubility and used as a charge transport material for an electrophotographic photoreceptor. The inventors have found that the characteristics, image characteristics, and repetition characteristics can be improved and the above problems can be solved, and the present invention has been completed.

That is, the gist of the present invention is an electrophotographic photosensitive member having at least a photosensitive layer on an electroconductive substrate, the photosensitive layer, contains represented luer reel amine compound of the following general formula [1] The present invention resides in an electrophotographic photosensitive member (claim 1).

(In the general formula [1], R ¹ and R ² each represents a methyl group, R ³ and R ⁴ each independently represent a hydrogen atom or a methyl group. Also, R ¹及beauty R ² is nitrogen and to atoms bonded at p-position. (However,. except when R ³ and R ⁴ are methyl groups attached to the m-position to the nitrogen atom))

At this time, R ³ and R ⁴ are preferably hydrogen atoms .

  Still another subject matter of the present invention is the electrophotographic photosensitive member, a charging portion for charging the electrophotographic photosensitive member, and an exposure portion for exposing the charged electrophotographic photosensitive member to form an electrostatic latent image. And an image forming apparatus comprising: a developing unit that develops the electrostatic latent image formed on the electrophotographic photosensitive member by exposure using toner (claim 3).

Arylamine-based compounds represented by the formula (1) has excellent solubility in Rukoto used as a charge-transporting material of an electrophotographic photoreceptor of the present invention, electric characteristics of the electrophotographic photosensitive member of the present invention, image characteristics , repetition characteristics are improved.

  Hereinafter, although an embodiment of the present invention is described in detail, the present invention is not limited to the following description, and can be appropriately modified and implemented without departing from the gist of the present invention.

[1. Arylamine compound]
The arylamine compound contained in the electrophotographic photoreceptor of the present invention (hereinafter sometimes referred to as “arylamine compound of the present invention”) is represented by the following general formula [1].

In the general formula [1], R ¹ and R ² each represents a methyl group. In addition, the position at which R ¹ and R ² are bonded to the corresponding benzene ring is arbitrary, and may be bonded to any position that can be bonded to each of the o-position and p-position with respect to the nitrogen atom. . Furthermore, the position at which R ¹ and R ² are bonded to the benzene ring may be the same or different, but from the viewpoint of ease of synthesis, the bonding positions are preferably the same.

In general formula [1], R ³ and R ⁴ each independently represents a hydrogen atom or a methyl group. In view of improving the residual potential, a methyl group is preferable, but a hydrogen atom is preferable from the viewpoint of raw material procurement. Further, the position at which R ³ and R ⁴ are bonded to the benzene ring is arbitrary, and it may be bonded at any position that can be bonded to each of the o-position and the m-position. The type of R ³ and R ⁴ and the position bonded to the benzene ring may be the same or different, but from the viewpoint of ease of synthesis, the type and the bonding position are preferably the same. .

  Hereinafter, the following exemplary compounds 1 to 8 are given as examples of the arylamine-based compound of the present invention, and these exemplary compounds 1 to 8 are shown for illustration, and the present invention includes these exemplary compounds 1 There is no limitation to ~ 8.

  The arylamine-based compound of the present invention described above has preferable characteristics as a charge transporting material, exhibiting a hole transporting property, a sufficiently low residual potential at the time of exposure, and high mobility. In addition, since the arylamine compound of the present invention exhibits high solubility in an organic solvent, it is suitable for use as a charge transport material contained in the photosensitive layer of an electrophotographic photoreceptor.

Next, the manufacturing method of the arylamine type compound of this invention is demonstrated.
The method for producing the arylamine compound of the present invention is not particularly limited as long as the arylamine compound having the structure represented by the general formula [1] can be produced. For example, after synthesizing the diphenylamine derivative, The method of making it react with dihalogenated biphenyl can be mentioned.

This manufacturing method will be described in detail. The following reaction formula (1) is a reaction formula showing an outline of this production method.

  In the reaction formula (1), X represents a bromine atom or an iodine atom. From the viewpoint of reactivity, preferred as X is an iodine atom, but from the viewpoint of inexpensive production, a bromine atom may be used.

  In the production method shown in the reaction formula (1), first, 3,4-xylidine or a 3,4-xylidine derivative is acetylated with acetic anhydride to prepare an amide derivative. This amide derivative is coupled with bromotoluene or iodotoluene, and the acetyl group is further deprotected with potassium hydroxide / propanol to derive a diarylamine form. Finally, the diarylamine form is coupled with dihalogenated biphenyl to synthesize the final product.

  In addition, each coupling reaction in the said manufacturing method may be performed by the Ullmann (Ullmann) reaction using a copper catalyst or an iron catalyst, and may be performed by the method of using a Pd catalyst. However, it is preferable to use a Pd catalyst from the viewpoint of improving electrical characteristics. Moreover, as a ligand of a Pd catalyst, a phosphorus derivative is preferable. In particular, from the viewpoint of reducing the purification load, that is, since the coupling reaction proceeds well, considering that the raw material hardly remains in the product and is easy to purify, the diarylamine compound and dihalogen in the final reaction step are considered. It is preferable to use a Pd catalyst in the coupling reaction with biphenyl fluoride.

  When coupling using a Pd catalyst, it is preferable to forcibly discharge the generated alcohol or the like out of the system at an early stage from the viewpoint of efficiently proceeding the reaction. When discharging, it is effective to use nitrogen flow. The flow rate of nitrogen is the ratio of the nitrogen flow volume per minute to the reaction vessel volume, usually 0.0001% or more, preferably 0.001% or more, and usually 5% or less, preferably 3% or less. It is. Nitrogen to be used is preferably of high purity, but nitrogen produced from liquid nitrogen may be used for inexpensive production.

  Moreover, as another manufacturing method of the arylamine type compound of this invention, the method led to the arylamine type compound of this invention after synthesize | combining a diphenylbenzidine derivative from dihalogenated biphenyl can be mentioned, for example.

[2. Electrophotographic photoreceptor]
Next, the electrophotographic photoreceptor of the present invention will be described in detail.
The structure of the electrophotographic photoreceptor of the present invention is not particularly limited as long as the above-described photosensitive layer containing the arylamine compound of the present invention is provided on a conductive support (substrate).

<Conductive support>
There is no particular limitation on the conductive support, but for example, metal materials such as aluminum, aluminum alloy, stainless steel, copper, and nickel, and conductive powder such as metal, carbon, and tin oxide are added to impart conductivity. A resin material, a resin, glass, paper, or the like on which a conductive material such as aluminum, nickel, or ITO (indium tin oxide alloy) is deposited or applied on its surface is mainly used. Moreover, these may be used individually by 1 type and may use 2 or more types together by arbitrary combinations and a ratio. As the form, for example, a drum shape, a sheet shape, a belt shape or the like is used. Further, a conductive material having an appropriate resistance value may be used on a conductive support made of a metal material in order to control conductivity and surface properties or to cover defects.

  Further, when a metal material such as an aluminum alloy is used as the conductive support, it may be used after anodizing. In addition, when anodizing is performed, it is desirable to perform sealing by a known method.

  The surface of the support may be smooth, or may be roughened by using a special cutting method or performing a polishing treatment. Further, it may be roughened by mixing particles having an appropriate particle diameter with the material constituting the support. In order to reduce the cost, it is possible to use the drawing tube as it is without performing the cutting process.

<Underlayer>
An undercoat layer may be provided between the conductive support and the photosensitive layer described later for improving adhesion and blocking properties. As the undercoat layer, a resin, a resin in which particles such as a metal oxide are dispersed, or the like is used.

  Examples of metal oxide particles used for the undercoat layer include metal oxide particles containing one metal element such as titanium oxide, aluminum oxide, silicon oxide, zirconium oxide, zinc oxide, iron oxide, calcium titanate, titanium Examples thereof include metal oxide particles containing a plurality of metal elements such as strontium acid and barium titanate. One kind of these particles may be used alone, or a plurality of kinds of particles may be mixed and used. Among these metal oxide particles, titanium oxide and aluminum oxide are preferable, and titanium oxide is particularly preferable. The surface of the titanium oxide particles may be treated with an inorganic substance such as tin oxide, aluminum oxide, antimony oxide, zirconium oxide or silicon oxide, or an organic substance such as stearic acid, polyol or silicone. As the crystal form of the titanium oxide particles, any of rutile, anatase, brookite, and amorphous can be used. Moreover, the thing of a several crystal state may be contained.

  In addition, various particle sizes of metal oxide particles can be used. Among them, the average primary particle size is usually 1 nm or more, preferably from the viewpoint of the characteristics of the resin as the raw material for the undercoat layer and the stability of the liquid. Is preferably 10 nm or more, and usually 100 nm or less, preferably 40 nm or less.

  The undercoat layer is preferably formed in a form in which metal oxide particles are dispersed in a binder resin. Examples of the binder resin used for the undercoat layer include phenoxy, epoxy, polyvinyl pyrrolidone, polyvinyl alcohol, casein, polyacrylic acid, celluloses, gelatin, starch, polyurethane, polyimide, and polyamide. These may be used alone or in combination of two or more in any combination and ratio. Moreover, you may use with the hardening | curing form with the hardening | curing agent. Among these, alcohol-soluble copolymerized polyamide, modified polyamide, and the like are preferable because they exhibit good dispersibility and coating properties.

  The mixing ratio of the inorganic particles to the binder resin used for the undercoat layer can be arbitrarily selected, but it is usually used in the range of 10% by weight to 500% by weight in terms of stability of the dispersion and coatability. Is preferable.

  Furthermore, the thickness of the undercoat layer can be arbitrarily selected, but from the viewpoint of improving the photoreceptor characteristics and applicability, it is usually 0.1 μm or more, preferably 0.2 μm or more, and usually 20 μm or less. Preferably it is 5 μm or less. Moreover, you may mix a well-known antioxidant etc. in an undercoat layer.

<Photosensitive layer>
Next, the photosensitive layer formed on the conductive support (if an undercoat layer described later is provided) will be described.
The photosensitive layer is a layer containing the above-described arylamine compound of the present invention as a charge transport material. As the type, the charge generation material and the charge transport material exist in the same layer and are dispersed in the binder resin. A single layer type, and a stacked type consisting of two layers of a charge generation layer in which a charge generation material is dispersed in a binder resin and a charge transport layer in which a charge transport material is dispersed in a binder resin. There may be. In general, it is known that the charge transport material exhibits the same performance as a charge transfer function regardless of whether it is a single layer type or a multilayer type.

  In addition, as the laminated photosensitive layer, a charge generation layer and a charge transport layer are laminated in this order from the conductive support side, and a charge transport layer and a charge generation layer are laminated in this order. There are reverse laminated type photosensitive layers, and any of them can be adopted, but a forward laminated type photosensitive layer capable of exhibiting the most balanced photoconductivity is preferable.

(Charge generation layer)
In the case of a multilayer photoreceptor, the charge generation layer is prepared by dispersing a charge generation material in a solution in which a binder resin is dissolved in an organic solvent to prepare a coating solution, which is applied onto a conductive support, and generating a charge. It is formed by binding substances with various binder resins.

  Examples of the charge generating material include selenium and its alloys, cadmium sulfide, and other inorganic photoconductive materials, and organic photoconductive materials such as organic pigments. Organic photoconductive materials are preferred, especially organic Pigments are preferred. Specific examples of organic pigments include phthalocyanine pigments, azo pigments, dithioketopyrrolopyrrole pigments, squalene (squarylium) pigments, quinacridone pigments, indigo pigments, perylene pigments, polycyclic quinone pigments, anthanthrone pigments, and benzimidazole pigments. It is done.

  Among the organic pigments exemplified above, a phthalocyanine pigment or an azo pigment is particularly preferable as the charge generation material. The phthalocyanine pigment provides a highly sensitive photoreceptor for a relatively long wavelength laser beam having a wavelength of 600 nm to 900 nm, and the azo pigment is a white light and a relatively short wavelength laser having a wavelength of 300 to 500 nm. Each is excellent in that it has sufficient sensitivity to light.

When a phthalocyanine compound is used as the charge generation material, specifically, a metal such as metal-free phthalocyanine, copper, indium, gallium, tin, titanium, zinc, vanadium, silicon, germanium, or an oxide, halide, hydroxide thereof And various crystal forms of coordinated phthalocyanines such as alkoxides. In particular, titanyl phthalocyanines (also known as oxytitanium) such as X-type, τ-type metal-free phthalocyanine, A-type (also known as β-type), B-type (also known as α-type), and D-type (also known as Y-type), which are highly sensitive crystal types Phthalocyanine), vanadyl phthalocyanine, chloroindium phthalocyanine, chlorogallium phthalocyanine such as type II, hydroxygallium phthalocyanine such as type V, μ-oxo-gallium phthalocyanine dimer such as type G and I, μ-oxo such as type II -Aluminum phthalocyanine dimer is preferred.

  Among the phthalocyanines, oxytitanium phthalocyanine having a main diffraction peak at a Bragg angle (2θ ± 0.2 °) of X-ray diffraction spectrum with respect to CuKa characteristic X-ray of 27.3 ° is 9.3 °, 13. Titanyl phthalocyanine (oxytitanium phthalocyanine) showing main diffraction peaks at 2 °, 26.2 ° and 27.1 °, 9.2 °, 14.1 °, 15.3 °, 19.7 °, 27.1 ° Dihydroxy silicon phthalocyanine having main diffraction peaks at 8.5 °, 12.2 °, 13.8 °, 16.9 °, 22.4 °, 28.4 ° and 30.1 ° Dichlorotin phthalocyanine, hydroxy potassium phthalose showing main diffraction peaks at 7.5 °, 9.9 °, 12.5 °, 16.3 °, 18.6 °, 25.1 ° and 28.3 ° Nin, and, 7.4 °, 16.6 °, chlorogallium phthalocyanine preferably exhibits a diffraction peak at 25.5 ° and 28.3 °. Among these, titanyl phthalocyanine (oxytitanium phthalocyanine) showing a main diffraction peak at 27.3 ° is particularly preferable, and in this case, titanyl phthalocyanine showing main diffraction peaks at 9.5 °, 24.1 ° and 27.3 °. (Oxytitanium phthalocyanine) is particularly preferred.

  As the phthalocyanine compound, one kind of compound may be used alone, or plural kinds of compounds may be used in a mixed or mixed crystal state. As the mixed state in the phthalocyanine compound or crystal state here, the respective constituent elements may be mixed and used later, or a mixed state is generated in the production / treatment process of phthalocyanine compound such as synthesis, pigmentation, crystallization, etc. It can be stuffed. As such treatment, acid paste treatment, grinding treatment, solvent treatment and the like are known. In order to generate a mixed crystal state, as described in JP-A-10-48859, two types of crystals are mixed, mechanically ground and made amorphous, and then converted into a specific crystal state by solvent treatment. The method of doing is mentioned.

  On the other hand, when an azo pigment is used as the charge generation material, various known bisazo pigments and trisazo pigments are preferably used. When an azo pigment is used as the charge generation material, various known bisazo pigments and trisazo pigments are preferably used. Examples of preferred azo pigments are shown below.

  The organic pigments exemplified above may be used alone or as a mixture of two or more pigments. In this case, it is preferable to use a combination of two or more kinds of charge generating materials having spectral sensitivity characteristics in different spectral regions of the visible region and the near red region, and among them, it is preferable to use a disazo pigment or a trisazo pigment and a phthalocyanine pigment in combination. More preferred.

  When an organic pigment is used as the charge generation material, these fine particles are used in a form bound with a binder resin. The type of binder resin is not particularly limited. For example, polyester resin, polyvinyl acetate, polyacrylic ester, polymethacrylic ester, polyester, polycarbonate, polyvinyl acetoacetal, polyvinyl propional, polyvinyl butyral, phenoxy resin, epoxy resin, urethane resin , Cellulose ester, cellulose ether and the like.

The use ratio of the charge generating material to the binder resin is usually in the range of 30 to 500 parts by weight of the charge generating material with respect to 100 parts by weight of the binder resin.
The thickness of the charge generation layer is usually 0.1 μm or more, preferably 0.15 μm or more, and usually 1 μm or less, preferably 0.6 μm or less.

(Charge transport layer)
The charge transport layer of the multilayer photoreceptor contains a charge transport material and usually contains a binder resin and other components used as necessary. Specifically, such a charge transport layer is prepared by, for example, preparing a coating solution by dissolving or dispersing a charge transport material and a binder resin in a solvent. In addition, in the case of a reverse lamination type photosensitive layer, it can be obtained by coating and drying on a conductive support (on the undercoat layer when an undercoat layer is provided).

As the charge transport material, the above-described arylamine compound of the present invention is used. The arylamine compounds of the present invention may be used alone or in combination of two or more in any ratio.
In addition to the arylamine compound of the present invention, other known charge transport materials may be used in combination. When other charge transport materials are used in combination, the kind thereof is not particularly limited. For example, carbazole derivatives, hydrazone compounds, aromatic amine derivatives, stilbene derivatives, butadiene derivatives, and those obtained by bonding a plurality of these derivatives are preferable. More specifically, compounds described in JP-A-2-230255, JP-A-63-225660, JP-A-58-198043, JP-B-58-32372, and JP-B-7-21646 Are preferably used.

  The binder resin is used for securing the film strength. Examples of the binder resin include polymers and copolymers of vinyl compounds such as butadiene, styrene, vinyl acetate, vinyl chloride, acrylic acid ester, methacrylic acid ester, vinyl alcohol, and ethyl vinyl ether, polyvinyl butyral, polyvinyl formal, and partially modified polyvinyl. Examples include acetal, polycarbonate, polyester, polyarylate, polyamide, polyurethane, cellulose ether, phenoxy resin, silicon resin, epoxy resin, and poly-N-vinylcarbazole resin. Of these, polycarbonate and polyarylate are particularly preferred. These can also be used after being crosslinked with heat, light or the like using an appropriate curing agent or the like. Moreover, these binders may be used individually by 1 type, and 2 or more types can also be used together by arbitrary combinations and a ratio.

  The ratio of the binder resin to the charge transport material is 20 parts by weight or more of the charge transport material with respect to 100 parts by weight of the binder resin. Among these, 30 parts by weight or more is preferable from the viewpoint of residual potential reduction, and 40 parts by weight or more is more preferable from the viewpoint of stability and charge mobility when repeatedly used. On the other hand, from the viewpoint of thermal stability of the photosensitive layer, the charge transport material is usually used at a ratio of 150 parts by weight or less. Among these, 110 parts by weight or less is preferable from the viewpoint of compatibility between the charge transport material and the binder resin, 80 parts by weight or less is more preferable from the viewpoint of printing durability, and 70 parts by weight or less is most preferable from the viewpoint of scratch resistance.

  The thickness of the charge transport layer is not particularly limited, but is usually 5 μm or more, preferably 10 μm or more, and usually 50 μm or less, preferably 45 μm or less, from the viewpoint of long life, image stability, and high resolution. Is in the range of 30 μm or less.

(Photosensitive layer of single layer type photoreceptor)
In addition to the charge generation material and the charge transport material, the photosensitive layer of the single-layer photoconductor is formed using a binder resin in order to ensure film strength, in the same manner as the charge transport layer of the multilayer photoconductor. Specifically, a charge generation material, a charge transport material, and various binder resins are dissolved or dispersed in a solvent to prepare a coating solution, and on a conductive support (or an undercoat layer when an undercoat layer is provided). It can be obtained by coating and drying.

  The types of the charge transport material and the binder resin and the use ratios thereof are the same as those described for the charge transport layer of the multilayer photoreceptor. The charge generating material is further dispersed in the charge transport medium comprising these charge transport material and binder resin.

  As the charge generation material, the same materials as those described for the charge generation layer of the multilayer photoreceptor can be used. However, in the case of a photosensitive layer of a single-layer type photoreceptor, it is necessary to sufficiently reduce the particle size of the charge generating material. Specifically, the range is usually 1 μm or less, preferably 0.5 μm or less.

  If the amount of the charge generating material dispersed in the single-layer type photosensitive layer is too small, sufficient sensitivity cannot be obtained, but if it is too large, there are adverse effects such as a decrease in chargeability and a decrease in sensitivity. It is usually used in the range of 0.5% by weight or more, preferably 1% by weight or more, and usually 50% by weight or less, preferably 20% by weight or less based on the whole layer-type photosensitive layer.

Further, the use ratio of the binder resin and the charge generating material in the single-layer type photosensitive layer is such that the charge generating material is usually 0.1 parts by weight or more, preferably 1 part by weight or more, based on 100 parts by weight of the binder resin. It is 30 parts by weight or less, preferably 10 parts by weight or less.
The film thickness of the single-layer type photosensitive layer is usually 5 μm or more, preferably 10 μm or more, and usually 100 μm or less, preferably 50 μm or less.

(Other)
For the purpose of improving film forming properties, flexibility, coating properties, contamination resistance, gas resistance, light resistance, etc., in both the photosensitive layer and the layers constituting the photosensitive layer, both of the multilayer type photosensitive member and the single layer type photosensitive member. Additives such as well-known antioxidants, plasticizers, ultraviolet absorbers, electron-withdrawing compounds, leveling agents, and visible light shielding agents may be included.

In both the multilayer type photoreceptor and the single-layer type photoreceptor, the photosensitive layer formed by the above-described procedure may be used as the uppermost layer, that is, the surface layer. However, another layer may be provided on the photosensitive layer and used as the surface layer. .
For example, a protective layer may be provided for the purpose of preventing the photosensitive layer from being worn out or preventing or reducing the deterioration of the photosensitive layer due to discharge products generated from a charger or the like.

  Further, for the purpose of reducing the frictional resistance and wear on the surface of the photoreceptor, a resin such as a fluorine-based resin or a silicone resin, or particles made of these resins or particles of an inorganic compound may be contained in the surface layer. Alternatively, a layer containing these resins and particles may be newly formed as a surface layer.

<Method for forming each layer>
Each layer constituting these photoreceptors is formed by immersing, coating, spraying, nozzle coating, bar coating, roll coating, blade coating, etc., on a support, a coating solution obtained by dissolving or dispersing a substance to be contained in a solvent. Are formed by sequential application by the known method.

  There are no particular restrictions on the solvent or dispersion medium used for the preparation of the coating solution, but specific examples include alcohols such as methanol, ethanol, propanol and 2-methoxyethanol, tetrahydrofuran, 1,4-dioxane, dimethoxyethane and the like. Ethers, esters such as methyl formate and ethyl acetate, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aromatic hydrocarbons such as benzene, toluene and xylene, dichloromethane, chloroform, 1,2-dichloroethane, 1,1, Chlorinated hydrocarbons such as 2-trichloroethane, 1,1,1-trichloroethane, tetrachloroethane, 1,2-dichloropropane, trichloroethylene, n-butylamine, isopropanolamine, diethylamine, triethanolamine, ethylenedi Min, nitrogen-containing compounds such as triethylenediamine, acetonitrile, N- methylpyrrolidone, N, N- dimethylformamide, aprotic polar solvents such as dimethyl sulfoxide and the like. Moreover, these may be used individually by 1 type and may use 2 or more types together by arbitrary combinations and kinds.

  The amount of the solvent or dispersion medium used is not particularly limited, but considering the purpose of each layer and the properties of the selected solvent / dispersion medium, it is appropriate so that the physical properties such as solid content concentration and viscosity of the coating liquid are within a desired range. It is preferable to adjust.

  For example, in the case of a photosensitive layer of a single layer type photoreceptor and a charge transport layer of a laminated type photoreceptor, the solid content concentration of the coating liquid or dispersion is usually 5% by weight or more, preferably 10% by weight or more. The range is usually 40% by weight or less, preferably 35% by weight or less. Furthermore, the viscosity of the coating solution or dispersion is usually in the range of 10 cps or more, preferably 50 cps or more, and usually 500 cps or less, preferably 400 cps or less.

  In the case of a charge generating layer of a multilayer photoreceptor, the solid content concentration of the coating solution or dispersion is usually 0.1% by weight or more, preferably 1% by weight or more, and usually 15% by weight or less, preferably Is in the range of 10% by weight or less. Furthermore, the viscosity of the coating solution or dispersion is usually in the range of 0.01 cps or more, preferably 0.1 cps or more, and usually 20 cps or less, preferably 10 cps or less.

  Examples of the coating method include a dip coating method, a spray coating method, a spinner coating method, a bead coating method, a wire bar coating method, a blade coating method, a roller coating method, an air knife coating method, and a curtain coating method. Other known coating methods can also be used.

  The coating liquid is preferably dried by touching at room temperature, usually in the temperature range of 30 ° C. or higher and 200 ° C. or lower, for 1 minute to 2 hours, statically or under ventilation. The heating temperature may be constant or the heating may be performed while changing the temperature during drying.

[3. Image forming apparatus]
Next, an embodiment of an image forming apparatus using the electrophotographic photosensitive member of the present invention (an image forming apparatus of the present invention) will be described with reference to FIG. However, the embodiment is not limited to the following description, and can be arbitrarily modified without departing from the gist of the present invention.

  As shown in FIG. 1, the image forming apparatus includes an electrophotographic photosensitive member 1, a charging device (charging unit) 2, an exposure device (exposure unit) 3, and a developing device (developing unit) 4. Accordingly, a transfer device 5, a cleaning device 6 and a fixing device 7 are provided.

  The electrophotographic photoreceptor 1 is not particularly limited as long as it is the above-described electrophotographic photoreceptor of the present invention, but in FIG. 1, as an example, a drum in which the above-described photosensitive layer is formed on the surface of a cylindrical conductive support. The photoconductor is shown. A charging device 2, an exposure device 3, a developing device 4, a transfer device 5, and a cleaning device 6 are disposed along the outer peripheral surface of the electrophotographic photosensitive member 1.

  The charging device 2 charges the electrophotographic photosensitive member 1 and uniformly charges the surface of the electrophotographic photosensitive member 1 to a predetermined potential. In FIG. 1, a roller-type charging device (charging roller) is shown as an example of the charging device 2, but other corona charging devices such as corotron and scorotron, and contact-type charging devices such as charging brushes are often used.

  In many cases, the electrophotographic photosensitive member 1 and the charging device 2 are designed to be removable from the main body of the image forming apparatus as a cartridge including both of them (hereinafter, appropriately referred to as a photosensitive cartridge). For example, when the electrophotographic photoreceptor 1 or the charging device 2 deteriorates, the photoreceptor cartridge can be removed from the image forming apparatus main body, and another new photosensitive cartridge can be mounted on the image forming apparatus main body. ing. Also, the toner described later is often stored in the toner cartridge and designed to be removable from the main body of the image forming apparatus. When the toner in the used toner cartridge runs out, this toner cartridge is removed. It can be removed from the main body of the image forming apparatus and another new toner cartridge can be mounted. Further, a cartridge equipped with all of the electrophotographic photosensitive member 1, the charging device 2, and the toner may be used.

  The type of the exposure apparatus 3 is not particularly limited as long as it can expose the electrophotographic photoreceptor 1 to form an electrostatic latent image on the photosensitive surface of the electrophotographic photoreceptor 1. Specific examples include halogen lamps, fluorescent lamps, lasers such as semiconductor lasers and He—Ne lasers, LEDs, and the like. Further, exposure may be performed by a photoreceptor internal exposure method. The light used for the exposure is arbitrary. For example, the exposure may be performed using monochromatic light with a wavelength of 780 nm, monochromatic light with a wavelength slightly shorter than 600 nm to 700 nm, or monochromatic light with a short wavelength of 380 nm to 500 nm. .

  The type of the developing device 4 is not particularly limited as long as it can develop the exposed electrostatic latent image on the electrophotographic photosensitive member 1 into a visible image. Specific examples include dry development methods such as cascade development, one-component conductive toner development, and two-component magnetic brush development, and wet development methods. In FIG. 1, the developing device 4 includes a developing tank 41, an agitator 42, a supply roller 43, a developing roller 44, and a regulating member 45, and has a configuration in which toner T is stored inside the developing tank 41. . Further, a replenishing device (not shown) for replenishing the toner T may be attached to the developing device 4 as necessary. The replenishing device is configured to be able to replenish toner T from a container such as a bottle or a cartridge.

  The supply roller 43 is formed from a conductive sponge or the like. The developing roller 44 is made of a metal roll such as iron, stainless steel, aluminum, or nickel, or a resin roll obtained by coating such a metal roll with a silicon resin, a urethane resin, a fluorine resin, or the like. The surface of the developing roller 44 may be smoothed or roughened as necessary.

  The developing roller 44 is disposed between the electrophotographic photoreceptor 1 and the supply roller 43 and is in contact with the electrophotographic photoreceptor 1 and the supply roller 43, respectively. The supply roller 43 and the developing roller 44 are rotated by a rotation drive mechanism (not shown). The supply roller 43 carries the stored toner T and supplies it to the developing roller 44. The developing roller 44 carries the toner T supplied by the supply roller 43 and contacts the surface of the electrophotographic photosensitive member 1.

  The regulating member 45 is formed of a resin blade such as silicon resin or urethane resin, a metal blade such as stainless steel, aluminum, copper, brass, phosphor bronze, or a blade obtained by coating such a metal blade with resin. The regulating member 45 contacts the developing roller 44 and is pressed against the developing roller 44 side with a predetermined force by a spring or the like (a general blade linear pressure is 5 to 500 g / cm). If necessary, the regulating member 45 may be provided with a function of imparting charging to the toner T by frictional charging with the toner T.

  The agitator 42 is rotated by a rotation driving mechanism, and agitates the toner T and conveys the toner T to the supply roller 43 side. A plurality of agitators 42 may be provided with different blade shapes and sizes.

  The type of the toner T is arbitrary, and in addition to the powdery toner, a polymerized toner using a suspension polymerization method, an emulsion polymerization method, or the like can be used. In particular, when a polymerized toner is used, a toner having a small particle diameter of about 4 to 8 μm is preferable, and the toner particles are used in various shapes ranging from a nearly spherical shape to a shape outside the spherical shape on the potato. be able to. The polymerized toner is excellent in charging uniformity and transferability and is suitably used for high image quality.

  The type of the transfer device 5 is not particularly limited, and an apparatus using an arbitrary system such as an electrostatic transfer method such as corona transfer, roller transfer, or belt transfer, a pressure transfer method, or an adhesive transfer method can be used. . Here, it is assumed that the transfer device 5 includes a transfer charger, a transfer roller, a transfer belt, and the like that are disposed to face the electrophotographic photoreceptor 1. The transfer device 5 applies a predetermined voltage value (transfer voltage) having a polarity opposite to the charging potential of the toner T, and transfers the toner image formed on the electrophotographic photosensitive member 1 to a recording paper (paper, medium) P. Is.

  There is no restriction | limiting in particular about the cleaning apparatus 6, Arbitrary cleaning apparatuses, such as a brush cleaner, a magnetic brush cleaner, an electrostatic brush cleaner, a magnetic roller cleaner, a blade cleaner, can be used. The cleaning device 6 is for scraping off residual toner adhering to the photoreceptor 1 with a cleaning member and collecting the residual toner.

  The fixing device 7 includes an upper fixing member (fixing roller) 71 and a lower fixing member (fixing roller) 72, and a heating device 73 is provided inside the fixing member 71 or 72. FIG. 1 shows an example in which a heating device 73 is provided inside the upper fixing member 71. Each of the upper and lower fixing members 71 and 72 includes a fixing roll in which a metal base tube such as stainless steel or aluminum is coated with silicon rubber, a fixing roll in which Teflon (registered trademark) resin is coated, and a fixing sheet. A member can be used. Further, each of the fixing members 71 and 72 may be configured to supply a release agent such as silicone oil in order to improve releasability, or may be configured to forcibly apply pressure to each other by a spring or the like.

When the toner transferred onto the recording paper P passes between the upper fixing member 71 and the lower fixing member 72 heated to a predetermined temperature, the toner is heated to a molten state and cooled after passing through the recording paper. Toner is fixed on P.
The type of the fixing device is not particularly limited, and a fixing device of any type such as heat roller fixing, flash fixing, oven fixing, pressure fixing, etc. can be provided including those used here.

  In the electrophotographic apparatus configured as described above, an image is recorded as follows. That is, first, the surface (photosensitive surface) of the photoreceptor 1 is charged to a predetermined potential (for example, −600 V) by the charging device 2. At this time, charging may be performed by a DC voltage, or charging may be performed by superimposing an AC voltage on the DC voltage.

  Subsequently, the photosensitive surface of the charged photoreceptor 1 is exposed by the exposure device 3 according to the image to be recorded, and an electrostatic latent image is formed on the photosensitive surface. The developing device 4 develops the electrostatic latent image formed on the photosensitive surface of the photoreceptor 1.

  The developing device 4 thins the toner T supplied by the supply roller 43 with a regulating member (developing blade) 45 and has a predetermined polarity (here, the same polarity as the charging potential of the photosensitive member 1) and the negative polarity. ), And conveyed while being carried on the developing roller 44 to be brought into contact with the surface of the photoreceptor 1.

When the charged toner T carried on the developing roller 44 comes into contact with the surface of the photoreceptor 1, a toner image corresponding to the electrostatic latent image is formed on the photosensitive surface of the photoreceptor 1. This toner image is transferred onto the recording paper P by the transfer device 5. Thereafter, the toner remaining on the photosensitive surface of the photoreceptor 1 without being transferred is removed by the cleaning device 6.
After the transfer of the toner image onto the recording paper P, the final image is obtained by passing the fixing device 7 and thermally fixing the toner image onto the recording paper P.

  In addition to the above-described configuration, the image forming apparatus may have a configuration capable of performing, for example, a static elimination process. The neutralization step is a step of neutralizing the electrophotographic photosensitive member by exposing the electrophotographic photosensitive member, and a fluorescent lamp, an LED, or the like is used as the neutralizing device. In addition, the light used in the static elimination process is often light having an exposure energy that is at least three times that of the exposure light.

  The image forming apparatus may be further modified. For example, the image forming apparatus may be configured to perform a pre-exposure process, an auxiliary charging process, or the like, or may be configured to perform offset printing. A full-color tandem system configuration using toner may be used.

  Hereinafter, the present invention will be described in more detail with reference to production examples, examples and comparative examples. In addition, the following examples are shown in order to describe the present invention in detail, and the present invention is not limited to the following examples unless it is contrary to the gist thereof.

<Production of arylamine compounds>
(Production Example 1: Production of Exemplary Compound 1)
122.0 g of 3,4-xylidine was dissolved in 219 ml of acetic anhydride with mechanical stirring under ice cooling. Thereafter, the reactor was heated to 150 ° C., refluxed at the same temperature for 10 hours, and then cooled to room temperature. To the obtained reaction mixture, 100 ml of toluene and 200 ml of water were added and stirred for about 1 hour, followed by liquid separation. The organic layer was transferred to a 500 ml beaker, and with stirring, a saturated sodium bicarbonate solution was slowly poured and neutralized until the pH was weakly basic. Thereafter, the layers were separated, and the organic layer was washed three times with 100 mL / time of water, dried over magnesium sulfate, and concentrated under reduced pressure. To the obtained oily substance, 70 mL of a mixed solution of toluene / hexane (1/2) was added, stirred under ice-cooling, and the precipitated white crystals were separated by filtration, and N-acetyl-3,4- was obtained as an amide derivative. 131.0 g of xylidine was obtained.

Under a nitrogen atmosphere, 24.8 g of the obtained N-acetyl-3,4-xylidine, 33.2 g of 4-iodotoluene, 4.9 g of copper powder, and 42.0 g of potassium carbonate were mixed, and the mixture was stirred at 180 ° C. for 7 The coupling reaction was carried out with heating and stirring for ˜8 hours.
After cooling to room temperature, 200 ml of toluene was added with stirring, insoluble matters were removed by filtration, and the mixture was concentrated under reduced pressure. To the obtained oil, 100 mL of 2-propanol and 10.2 g of potassium hydroxide were added, and the mixture was further heated under reflux for 3 hours to deprotect the acetyl group.
After cooling to room temperature, 100 ml of toluene and 150 ml of water were added to separate the layers. The organic layer was washed 3 times with 50 mL / time of water, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained oily substance was dissolved in a mixed solution of toluene / hexane (1/1) and then passed through column chromatography (silica gel 1000 g, developing solvent: toluene / hexane = 1/1) to give N- ( There were obtained 29.9 g of 4-tolyl) -N- (3,4-xylyl) amine as a white solid.

  In a 300 ml four-necked flask under a nitrogen atmosphere, 8.7 g of the obtained N- (4-tolyl) -N- (3,4-xylyl) amine, 100 ml of xylene, 4,4′-diiodobiphenyl 8 0.1 g and 4.6 g of sodium-tert-butoxide were added, and 10 ml of a xylene solution containing 9.0 mg of palladium acetate and 32.4 mg of tri-tert-butylphosphine was added with stirring. Thereafter, the reactor was heated to 120 ° C. and continued to be heated at that temperature for 2 to 3 hours to be reacted. After completion of the reaction, the reaction mixture was cooled, and 100 ml of toluene and 100 ml of water were added for liquid separation. The organic layer was washed with 50 mL / time of water three times, contacted with magnesium sulfate, dried, and then concentrated under reduced pressure. The obtained crude product was dissolved in 10-15 mL of a toluene / hexane (1/1) mixed solution by heat and then passed through column chromatography (silica gel 500 g, developing solvent: toluene / hexane = 1/1). Exemplified compound 1 was obtained (10.8 g).

<Production of electrophotographic photoreceptor>
(Example 1: Electrophotographic photoreceptor A1)
Using a conductive support in which an aluminum vapor-deposited layer (thickness 70 nm) is formed on the surface of a biaxially stretched polyethylene terephthalate resin film (thickness 75 μm), the following undercoat layer dispersion is formed on the aluminum vapor-deposited layer of the conductive support The liquid was applied by a bar coater so that the film thickness after drying was 1.25 μm and dried to form an undercoat layer.

  The undercoat layer dispersion was produced as follows. That is, a rutile type titanium oxide having an average primary particle size of 40 nm (“TTO55N” manufactured by Ishihara Sangyo Co., Ltd.) and 3% by weight of methyldimethoxysilane with respect to the titanium oxide were mixed in a ball mill to obtain a slurry. The obtained slurry was dried, further washed with methanol and dried, and the obtained hydrophobic treated titanium oxide was dispersed by a ball mill in a mixed solvent of methanol / 1-propanol to obtain a hydrophobized treated titanium oxide dispersed slurry. . The dispersion slurry, a mixed solvent of methanol / 1-propanol / toluene (weight ratio 7/1/2), ε-caprolactam / bis (4-amino-3-methylphenyl) methane / hexamethylenediamine / decamethylenedicarboxylic After stirring and mixing the pellets of copolymerized polyamide comprising acid / octadecamethylenedicarboxylic acid (composition mol%: 75 / 9.5 / 3 / 9.5 / 3) to dissolve the polyamide pellets Then, ultrasonic dispersion treatment was performed. As a result, a dispersion for an undercoat layer having a solid content concentration of 18.0% by weight containing a hydrophobically treated titanium oxide / copolymerized polyamide at a weight ratio of 3/1 was produced.

  Separately, A-type oxytitanium phthalocyanine (showing diffraction peaks at 9.3 °, 10.6 °, and 26.3 ° at Bragg angles (2θ ± 0.2 °) in the X-ray diffraction spectrum for CuKa characteristic X-ray) 10 Part by weight was added to 150 parts by weight of 4-methoxy-4-methylpentanone-2 and pulverized and dispersed in a sand grind mill for 1 hour. Thereafter, 100 parts by weight of a 5% by weight 1,2-dimethoxyethane solution of polyvinyl butyral (“Decbutyral # 6000C” manufactured by Denki Kagaku Kogyo Co., Ltd.) as a binder resin, and phenoxy resin (“PKHH” manufactured by Union Carbide) The charge generation layer coating solution was prepared by adding 100 parts by weight of a 5 wt% 1,2-dimethoxyethane solution. The charge generation layer coating solution was applied onto the undercoat layer of the conductive support with a bar coater so that the film thickness after drying was 0.4 μm, and dried to form a charge generation layer. .

  Separately, 50 parts by weight of Exemplified Compound 1 (high-purity arylamine) obtained in Production Example 1 as a charge transport material, 100 parts by weight of a binder resin, and 0.03 part by weight of silicone oil as a leveling agent were added in tetrahydrofuran. / Toluene (weight ratio 8/2) was dissolved in 640 parts by weight of a mixed solvent to prepare a charge transport layer coating solution. In addition, as binder resin, the repeating unit 51 mol% which uses the following 2, 2-bis (4-hydroxy-3-methylphenyl) propane as an aromatic diol component, and 1,1-bis (4-hydroxyphenyl) are shown. ) A polycarbonate resin (viscosity average molecular weight 30000) having a terminal structure derived from pt-butylphenol, comprising 49 mol% of repeating units containing 1-phenylethane as an aromatic diol component.

  The charge transport layer coating solution is applied onto the charge generation layer with a film applicator so that the film thickness after drying is 20 μm, and is dried to form a charge transport layer. Photoreceptor A1 was produced.

(Comparative Example 1: Electrophotographic photoreceptor P1)
An electrophotographic photosensitive member P1 as a comparative example was obtained in the same manner as in Example 1 except that the charge transport material a represented by the following structural formula was used in place of the exemplified compound 1.

(Comparative Example 2: Electrophotographic photoreceptor P2)
An electrophotographic photosensitive member P2 as a comparative example was obtained in the same manner as in Example 1 except that the following charge transport material b exemplified in Non-Patent Document 1 was used in place of the exemplified compound 1.

(Comparative Example 3: Electrophotographic photoreceptor P3)
An electrophotographic photoreceptor P3 as a comparative example was obtained in the same manner as in Example 1 except that the following charge transport material c exemplified in Patent Document 3 was used instead of the exemplified compound 1. Crystals were deposited during the coating of the film, and the characteristics were not measured.

(Comparative Example 4: Electrophotographic photoreceptor P4)
An electrophotographic photosensitive member P4 was obtained in the same manner as in Example 1 except that the following charge transport material d exemplified in JP-A-5-188665 was used in place of the exemplified compound 1.

(Comparative Example 5: electrophotographic photoreceptor P5)
An electrophotographic photosensitive member P5 was obtained in the same manner as in Example 1 except that the following charge transport material e exemplified in JP-A-6-324502 was used in place of the exemplified compound 1.

(Comparative Example 6: electrophotographic photoreceptor P6)
An electrophotographic photosensitive member P6 was obtained in the same manner as in Example 1 except that the following charge transport material f exemplified in Patent Document 5 was used in place of the exemplified compound 1. It was confirmed that the charge transport material f has difficulty in solubility, although the preparation of the coating solution requires heat dissolution. In addition, crystallization was observed in a part of the photoreceptor.

<Evaluation of electrical characteristics of electrophotographic photoreceptor>
The electrophotographic characteristics of the obtained electrophotographic photoreceptors A1, P1, P2, P4 to P6 were measured by the static method as follows using a photoreceptor evaluation apparatus (Cynthia 55, manufactured by Gentec Corporation). .

First, an electrophotographic photosensitive member is discharged with a scorotron charger in a dark place so that the surface potential is about 700 V, and charged by passing through the electrophotographic photosensitive member at a constant speed (125 mm / sec). Was measured, and the initial charging voltage (V ₀ ) was determined. Thereafter, the potential drop (DD) was measured when left for 2.5 seconds. Next, irradiation with 780 nm monochromatic light having an intensity of 1.0 μW / cm ² , and half exposure energy E _1/2 (μJ / cm ² ) required until the photoreceptor surface potential is changed from −550 V to −275 V, The residual potential (V _r ) 10 seconds after irradiation was determined.
Table 1 shows the evaluation results of the electrophotographic photoreceptors A1, P1, P2, and P4 to P6.

  As described above, in Comparative Example 3, the charge transport material c was poorly soluble and an excellent electrophotographic photosensitive member could not be produced. In Example 1, the arylamine compound of the present invention was used. Exemplified Compound 1 showed high solubility, so that a good electrophotographic photoreceptor A1 could be produced.

As shown in Table 1, the electrophotographic photosensitive member A1 has a half-exposure energy smaller than that of the electrophotographic photosensitive members P1, P2, P4 to P6, and a residual voltage V _r after 10 seconds from irradiation. Therefore, the electrophotographic photoreceptor A1 using the exemplified compound 1 which is the arylamine compound of the present invention as a charge transport material is better than the electrophotographic photoreceptor using the conventional charge transport materials a, b and df. It was confirmed that the electrical characteristics were exhibited.

<Image formation test and photoreceptor stability / durability test>
Example 4
A coating solution for a charge generation layer and a charge transport layer prepared in the same manner as the electrophotographic photoreceptor A1 is dip-coated on an aluminum tube having a diameter of 3 cm and a length of 25.4 cm, which has been anodized and sealed. Were sequentially coated and dried to produce an electrophotographic photosensitive drum having a film thickness of 0.3 μm and a charge transport layer of 20 μm. When this electrophotographic photosensitive drum was mounted on a laser printer, Laser Jet 4 (LJ4) manufactured by Hewlett Packard, an image test was performed, and a good image free from image defects and noise was obtained. Subsequently, 10,000 sheets were continuously printed, but no image deterioration such as ghosting, fogging, and black spots was observed, and the printing was stable.

(Comparative Example 8)
In the procedure of Example 4, an electrophotographic photosensitive drum was prepared in the same procedure as in Example 4 except that the charge transport layer coating solution prepared in the same manner as that of the electrophotographic photosensitive member P1 was used. As a result, a good image free from image defects and noise was obtained. Next, when 10,000 sheets were continuously printed, no change was observed in the ghost, but deterioration was observed in fog.

  From Example 4 and Comparative Example 8, the electrophotographic photosensitive member P1 has a problem in repeatability and is difficult to use, but the electrophotographic photoreceptor A1 that is an example of the present invention has excellent repeatability. confirmed.

  The present invention can be carried out in any field that requires an electrophotographic photoreceptor, and is suitable for use in, for example, a copying machine, a printer, a printing machine, and the like.

1 is a schematic diagram illustrating a main configuration of an embodiment of an image forming apparatus of the present invention.

Explanation of symbols

1 Photoconductor (Electrophotographic photoconductor)
2 Charging device (charging roller; charging unit)
3 Exposure equipment (exposure section)
4 Development device (development unit)
DESCRIPTION OF SYMBOLS 5 Transfer apparatus 6 Cleaning apparatus 7 Fixing apparatus 41 Developing tank 42 Agitator 43 Supply roller 44 Developing roller 45 Control member 71 Upper fixing member (fixing roller)
72 Lower fixing member (fixing roller)
73 Heating device T Toner P Recording paper (paper, medium)

Claims (3)

An electrophotographic photoreceptor having at least a photosensitive layer on a conductive support,
The electrophotographic photoreceptor, wherein the photosensitive layer contains an arylamine compound represented by the following general formula [1].

(In the general formula [1], R ¹ and R ² each represents a methyl group, R ³ and R ⁴ each independently represent a hydrogen atom or a methyl group. Also, R ¹及beauty R ² is nitrogen and to atoms bonded at p-position. (However,. except when R ³ and R ⁴ are methyl groups attached to the m-position to the nitrogen atom)) The electrophotographic photosensitive member according to claim 1, wherein R ³ and R ⁴ are hydrogen atoms. An electrophotographic photosensitive member, a charging portion that charges the electrophotographic photosensitive member, an exposure portion that exposes the charged electrophotographic photosensitive member to form an electrostatic latent image, and is formed on the electrophotographic photosensitive member by exposure. An image forming apparatus comprising: a developing unit that develops the electrostatic latent image formed using toner;
An image forming apparatus, wherein the electrophotographic photosensitive member is the electrophotographic photosensitive member according to claim 1.

Images