WO2022210315A1 - 電子写真感光体、電子写真感光体カートリッジ及び画像形成装置 - Google Patents
電子写真感光体、電子写真感光体カートリッジ及び画像形成装置 Download PDFInfo
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- WO2022210315A1 WO2022210315A1 PCT/JP2022/014214 JP2022014214W WO2022210315A1 WO 2022210315 A1 WO2022210315 A1 WO 2022210315A1 JP 2022014214 W JP2022014214 W JP 2022014214W WO 2022210315 A1 WO2022210315 A1 WO 2022210315A1
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- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
- G03G5/147—Cover layers
- G03G5/14708—Cover layers comprising organic material
- G03G5/14713—Macromolecular material
- G03G5/14717—Macromolecular material obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G5/1473—Polyvinylalcohol, polyallylalcohol; Derivatives thereof, e.g. polyvinylesters, polyvinylethers, polyvinylamines
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
- G03G5/147—Cover layers
- G03G5/14708—Cover layers comprising organic material
- G03G5/14713—Macromolecular material
- G03G5/14786—Macromolecular compounds characterised by specific side-chain substituents or end groups
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
- G03G5/147—Cover layers
- G03G5/14708—Cover layers comprising organic material
- G03G5/14713—Macromolecular material
- G03G5/14795—Macromolecular compounds characterised by their physical properties
Definitions
- the present invention relates to an electrophotographic photoreceptor used in copiers, printers, etc., a cartridge using the same, and an image forming apparatus.
- the photoreceptor In printers and copiers, when a charged organic photoreceptor (OPC) drum is irradiated with light, the charge is removed from that portion to produce an electrostatic latent image, and an image is obtained by adhering toner to the electrostatic latent image. be able to.
- OPC organic photoreceptor
- the photoreceptor In such devices using electrophotographic technology, the photoreceptor is a basic member.
- This type of organic photoreceptor has a wide range of materials to choose from, and the characteristics of the photoreceptor are easy to control. Therefore, it is a "function-separated photoreceptor" that separates the functions of generating and transferring negative charges to separate compounds. is becoming mainstream.
- a single-layer electrophotographic photoreceptor (hereinafter referred to as a single-layer photoreceptor) having a charge-generating material (CGM) and a charge-transporting material (CTM) in the same layer and a charge-generating material (CGM)
- CGM charge-generating material
- CTM charge-transporting material
- CGM charge-generating material
- a laminate type electrophotographic photoreceptor (hereinafter referred to as a laminate type photoreceptor) is known which is formed by stacking a charge generation layer and a charge transport layer containing a charge transport material (CTM).
- a method of charging the photoreceptor there are a negative charging method of negatively charging the surface of the photoreceptor and a positive charging method of positively charging the surface of the photoreceptor.
- Combinations of the layer structure and charging method of photoreceptors that are currently in practical use include a "negatively charged multi-layer photoreceptor" and a "positively charged single-layer photoreceptor.”
- a “negative charging laminated photoreceptor” is an undercoat layer (UCL) made of resin or the like provided on a conductive substrate such as an aluminum tube, and a charge generation material (CGM) and a charge generation layer made of resin or the like is provided thereon.
- CGL is provided, and a charge transport layer (CTL) made of a hole transport material (HTM) and a resin is provided thereon.
- the "positive charging single layer type photoreceptor” is provided with an undercoat layer (UCL) made of resin or the like on a conductive substrate such as an aluminum tube, and a charge generating material (CGM), a hole transporting material, and a hole transporting material are provided thereon.
- UCL undercoat layer
- CGM charge generating material
- HTM high temperature polymer
- ETM electron transport material
- Patent Document 1 a structure in which a single-layered photosensitive layer made of a material (HTM), an electron transport material (ETM), and a resin is provided (see, for example, Patent Document 1).
- the photoreceptor After the surface of the photoreceptor is charged by the corona discharge method or the contact method, the photoreceptor is exposed to light to neutralize the surface charge, forming an electrostatic latent image due to the potential difference with the surrounding surface. do. After that, a toner image corresponding to the electrostatic latent image is formed by bringing toner into contact with the surface of the photoreceptor, and the image is transferred, heated, melted and fixed to paper or the like to complete the print.
- the basic structure of the electrophotographic photoreceptor is that the photosensitive layer is formed on the conductive support. It is
- a layer containing a compound having a chain polymerizable functional group is formed as a binder resin on the outermost layer of the photoreceptor.
- a photoreceptor has been disclosed in which a cured resin layer is formed by polymerizing by applying energy such as (see, for example, Patent Documents 1 and 2).
- Patent Document 3 discloses an electrophotographic photoreceptor having a layer structure, wherein at least one outermost layer of the layers has a structure in which at least one carbonyl group is bonded to an aromatic group, and the following formula (A) An electrophotographic photoreceptor containing a polymer having the structure represented is disclosed.
- R 11 to R 13 are groups represented by the following formula (2), and in the following formula (2), R 21 represents a hydrogen atom or a methyl group, and R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- a (meth)acrylic monomer structure with low moisture absorption for example, a monomer having a structure in which a substituent having a (meth)acryloyl group is bonded.
- a monomer having a structure in which a substituent having a (meth)acryloyl group is bonded may deteriorate electrical properties when used.
- An object of the present invention is to provide an electrophotographic photoreceptor capable of suppressing image flow and maintaining electrical properties at the same time and having good Martens hardness and elastic deformation rate, and an electrophotographic photoreceptor cartridge using the electrophotographic photoreceptor. and to provide an image forming apparatus.
- the present inventors have proposed an electrophotographic photoreceptor having a photosensitive layer on a conductive support, wherein the protective layer, for example, the outermost layer on the side opposite to the conductive support, has a specific structure.
- the present invention proposes an electrophotographic photoreceptor containing a polymer.
- the gist of the present invention lies in [1] to [20] below.
- An electrophotographic photoreceptor having at least a photosensitive layer and a protective layer in this order on a conductive support
- X represents a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure is an alkylene structure, an alkenylene structure or an alkynylene structure.
- a 1 and A 2 each independently represent the following formula (A).
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by the following formula (2), and among R 11 to R 13 At least two are groups represented by the following formula (2).
- Z 1 indicates a bond with an arbitrary atom.
- R 21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (A) bond.
- Z3 indicates a bond with an arbitrary atom.
- An electrophotographic photoreceptor having a photosensitive layer on a conductive support An electrophotographic photoreceptor in which the outermost layer opposite to the conductive support contains a polymer having a structure represented by the formula (a).
- X represents a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure is an alkylene structure, alkenylene structure or alkynylene structure.
- a 1 and A 2 each independently represent the following formula (A').
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by the following formula (2'), and R 11 to R 13 At least two of them are groups represented by the following formula (2').
- Z 1 indicates a bond with an arbitrary atom.
- R21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in the formula (A') are bonded.
- An electrophotographic photoreceptor having at least a photosensitive layer and a protective layer in this order on a conductive support
- X represents a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure is an alkylene structure, alkenylene structure or alkynylene structure.
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by the following formula (2), and among R 11 to R 13 At least two are groups represented by the following formula (2).
- Z 1 indicates a bond with an arbitrary atom.
- R 21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (A) bond.
- Z3 indicates a bond with an arbitrary atom.
- An electrophotographic photoreceptor having a photosensitive layer on a conductive support An electrophotographic photoreceptor in which the outermost layer opposite to the electrophotographic photoreceptor contains a polymer having a partial structure represented by the formula (b) and a partial structure represented by the formula (A).
- the polymer is a polymer of a compound having a partial structure represented by the above formula (b) and a partial structure represented by the following formula (A') in the same molecule, the above [4] or The electrophotographic photoreceptor according to [5].
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by the following formula (2'), and R 11 to R 13 At least two of them are groups represented by the following formula (2').
- Z 1 indicates a bond with an arbitrary atom.
- R21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in the formula (A') are bonded.
- An electrophotographic photoreceptor having at least a photosensitive layer and a protective layer in this order on a conductive support
- X represents a hydrocarbon structure having 4 or more and 20 or less carbon atoms, and the hydrocarbon structure is an alkylene structure, an alkenylene structure or an alkynylene structure.
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, a group represented by the following formula (2), or represented by the following formula (3) at least two of R 11 to R 13 are a group represented by the following formula (2) or a group represented by the following formula (3).
- R 14 and R 15 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- R16 is a single bond or an oxygen atom.
- R17 is a single bond.
- n11 represents an integer of 1 or more and 10 or less.
- Z4 indicates a bond with an arbitrary atom.
- R 21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (B) bond.
- Z3 indicates a bond with an arbitrary atom.
- R 31 to R 33 each independently represent a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group or a group represented by the above formula (2), and among R 31 to R 33 At least two represent groups represented by the formula (2).
- R 34 to R 37 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n 31 and n 32 each independently represent an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (B) bond.
- X is a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure is an alkylene structure, an alkenylene structure, or an alkynylene structure.
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, a group represented by the following formula (2) or a group represented by the following formula (3). At least two of R 11 to R 13 are groups represented by the following formula (2) or groups represented by the following formula (3).
- R 14 and R 15 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- R16 is a single bond or an oxygen atom.
- R17 is a single bond.
- n12 is 2 and n11 represents an integer of 1 or more and 10 or less.
- R 21 represents a hydrogen atom or a methyl group
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group
- n 21 is an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (1) bond.
- Z3 indicates a bond with an arbitrary atom.
- R 31 to R 33 each independently represent a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group or a group represented by the above formula (2), and among R 31 to R 33 At least two represent groups represented by the formula (2).
- R 34 to R 37 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n 31 and n 32 each independently represent an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (1) bond.
- R 21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (A) bond.
- Z3 indicates a bond with an arbitrary atom.
- R21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in the formula (A') are bonded.
- An electrophotographic photoreceptor having at least a photosensitive layer and a protective layer in this order on a conductive support,
- the protective layer polymerizes a reaction product of an aliphatic dicarboxylic acid or an aliphatic dicarboxylic acid chloride, a polyhydric alcohol, and at least one selected from the group consisting of acrylic acid, methacrylic acid, acrylic acid chloride and methacrylic acid chloride.
- the electrophotographic photoreceptor according to any one of [1] to [16], wherein the protective layer or the outermost layer contains metal oxide particles.
- the content of the metal oxide particles in the protective layer or the outermost layer is 300 parts by mass or less with respect to 100 parts by mass of the polymer in the protective layer or the outermost layer.
- An electrophotographic photoreceptor cartridge comprising the electrophotographic photoreceptor according to any one of [1] to [19].
- An image forming apparatus comprising the electrophotographic photoreceptor according to any one of [1] to [19].
- the electrophotographic photoreceptor of the present invention can both suppress image flow and maintain electrical properties due to the action of the polymer contained in the protective layer (outermost layer), and furthermore, has good Martens hardness and elastic deformation rate. can be
- FIG. 10 is a scanning electron microscope image (SEM image) of a cross section of the laminated photoreceptor obtained in Comparative Example 4.
- FIG. 10 When measuring the Martens hardness and elastic deformation rate of the binder resin forming the photosensitive layer in contact with the protective layer (outermost layer), or when measuring the Martens hardness and elastic deformation rate of the surface of the photoreceptor, the indenter 4 is a graph showing a model of a load curve with respect to indentation depth;
- (Meth)acrylic in the present invention means acrylic or methacrylic.
- (Meth)acryloyl means acryloyl or methacryloyl.
- An electrophotographic photoreceptor (referred to as "this electrophotographic photoreceptor") according to an embodiment of the present invention is an electrophotographic photoreceptor having at least a photosensitive layer and a protective layer in this order on a conductive support. and the protective layer contains a polymer having a specific structure.
- the side opposite to the conductive support is the upper side or front side, and the conductive support side is the lower side or back side. Therefore, the protective layer (outermost layer) is located on the side opposite to the conductive support.
- the present electrophotographic photoreceptor can have a layer structure similar to that of a general electrophotographic photoreceptor.
- a typical electrophotographic photoreceptor has a layer structure in which at least a photosensitive layer and a protective layer (outermost layer) are sequentially provided on a conductive support.
- the protective layer is preferably the outermost layer, that is, the outermost layer located on the side opposite to the conductive support, from the viewpoint of obtaining the effects of the present invention.
- the effects of the present invention can be obtained even if the protective layer is not necessarily the outermost layer.
- the term "protective layer (outermost layer)" includes the meaning that the protective layer is not necessarily the outermost layer, but is preferably a protective layer as the outermost layer.
- This electrophotographic photoreceptor has a conductive support under a photosensitive layer, which will be described later.
- the conductive support is not particularly limited as long as it can support the photosensitive layer positioned thereon and exhibits conductivity.
- the conductive support examples include metal materials such as aluminum, aluminum alloys, stainless steel, copper, and nickel; resin materials imparted with conductivity by the coexistence of conductive powder such as metal, carbon, and tin oxide; A resin, glass, paper, or the like having a surface vapor-deposited or coated with a conductive material such as aluminum, nickel, or ITO (indium tin oxide) can be used.
- metal materials such as aluminum, aluminum alloys, stainless steel, copper, and nickel
- a resin, glass, paper, or the like having a surface vapor-deposited or coated with a conductive material such as aluminum, nickel, or ITO (indium tin oxide) can be used.
- Examples of the form of the conductive support include a drum shape, a sheet shape, and a belt shape.
- the metal material When using a metal material such as an aluminum alloy as the conductive support, the metal material may be coated with an anodized film before use.
- the pore-sealing treatment can be performed by a known method.
- the average thickness of the anodized film is usually 20 ⁇ m or less, preferably 7 ⁇ m or less.
- the surface of the conductive support may be smooth or may be roughened by using a special cutting method or polishing treatment. Alternatively, the surface may be roughened by mixing particles having an appropriate particle size with the material constituting the support.
- An undercoat layer which will be described later, may be provided between the conductive support and the photosensitive layer in order to improve adhesion, blocking properties, and the like.
- This electrophotographic photoreceptor comprises a photosensitive layer on the conductive support.
- the photosensitive layer may be a single-layer type photosensitive layer in which a charge-generating material (CGM), a hole-transporting material (HTM), an electron-transporting material (ETM) and a binder resin are present in the same layer, or It may be a laminate type photosensitive layer in which a charge generation layer and a charge transport layer are separated.
- the laminate-type photosensitive layer may have a form in which the charge generation layer and the charge transport layer are laminated in this order from the conductive support side, or a form in which the charge transport layer and the charge generation layer are laminated in this order.
- the photosensitive layer in contact with the protective layer preferably contains a charge-transporting substance.
- the concentration of the charge transport substance in the photosensitive layer is preferably 30% by mass or more, more preferably 35% by mass or more, and more preferably 40% by mass or more.
- the content is preferably 70% by mass or less, more preferably 65% by mass or less, and more preferably 62% by mass or less.
- the glass transition temperature of the photosensitive layer in contact with the protective layer (outermost layer) is preferably 50°C or higher, especially 60°C or higher, and especially 70°C or higher. is more preferable.
- the glass transition temperature is preferably 130° C. or lower, more preferably 120° C. or lower, and more preferably 110° C. or lower.
- the Martens hardness of the photosensitive layer in contact with the protective layer (outermost layer) is preferably 160 N/mm 2 or more, especially 170 N/mm 2 or more. , more preferably 180 N/mm 2 or more.
- the Martens hardness is preferably 260 N/mm 2 or less, more preferably 250 N/mm 2 or less, and more preferably 240 N/mm 2 or less.
- the elastic deformation rate of the photosensitive layer in contact with the protective layer (outermost layer) is preferably 35% or more, especially 37% or more, especially 39%. % or more is more preferable.
- the elastic deformation rate is preferably 50% or less, more preferably 47% or less, and more preferably 44% or less.
- the Martens hardness and elastic deformation rate of the photosensitive layer in contact with the protective layer (outermost layer) are determined by the method described later for a photoreceptor that does not have a protective layer (outermost layer), i.e., the photosensitive layer is the outermost layer.
- the method for measuring the Martens hardness and elastic deformation rate of the photosensitive layer in contact with the protective layer (outermost layer) is the same as the method for measuring the Martens hardness and elastic deformation rate of the binder resin forming the photosensitive layer, which will be described later.
- the charge generation layer (CGL) usually contains a charge generation material (CGM) and a binder resin.
- the content of the charge-generating substance in the binder resin is preferably 10 parts by mass or more, more preferably 30 parts by mass or more, per 100 parts by mass of the binder resin. On the other hand, it is preferably 1000 parts by mass or less, more preferably 500 parts by mass or less. From the viewpoint of film strength, it is more preferably 300 parts by mass or less, and even more preferably 200 parts by mass or less.
- the thickness of the charge generation layer is preferably 0.1 ⁇ m or more, more preferably 0.15 ⁇ m or more. On the other hand, it is preferably 10 ⁇ m or less, more preferably 0.6 ⁇ m or less.
- the charge transport layer (CTL) usually contains a hole transport material (HTM) and a binder resin. Further, an electron transport material (ETM) may be contained.
- HTM hole transport material
- ETM electron transport material
- the content ratio of the hole transport material (HTM) to the binder resin is preferably 20 parts by mass or more per 100 parts by mass of the binder resin.
- the hole transport material (HTM) is 30 parts by mass or more with respect to 100 parts by mass of the binder resin. From the point of view, it is more preferably 40 parts by mass or more.
- the hole transport material (HTM) is 200 parts by mass or less per 100 parts by mass of the binder resin. From the viewpoint of compatibility with, it is more preferably 150 parts by mass or less, and from the viewpoint of the glass transition temperature, it is particularly preferably 120 parts by mass or less.
- the content ratio of the electron transport material (ETM) to the binder resin is 100 mass of the binder resin from the viewpoint of the electron transport property in the charge transport layer.
- the electron transport material (ETM) is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and more preferably 2 parts by mass or more.
- the amount is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and more preferably 10 parts by mass or less.
- the content ratio (mass ratio) of the electron transport material (ETM) to the hole transport material (HTM) is The electron transport material (ETM) is preferably 0.005 or more, more preferably 0.01 or more, and more preferably 0.02 or more. On the other hand, from the viewpoint of hole transportability, it is preferably 0.2 or less, more preferably 0.1 or less, and more preferably 0.05 or less.
- the thickness of the charge transport layer is not particularly limited. From the viewpoint of electrical properties, image stability, and high resolution, the thickness is preferably 5 ⁇ m or more and 50 ⁇ m or less, more preferably 10 ⁇ m or more or 35 ⁇ m or less, and more preferably 15 ⁇ m or more or 25 ⁇ m or less.
- the single-layer type photosensitive layer usually contains a charge generation material (CGM), a hole transport material (HTM), an electron transport material (ETM) and a binder resin.
- CGM charge generation material
- HTM hole transport material
- ETM electron transport material
- the content ratio of the charge-generating substance to the binder resin is preferably 1 part by mass or more, more preferably 1.5 parts by mass or more, per 100 parts by mass of the binder resin. is more preferable, and more preferably 2 parts by mass or more. On the other hand, it is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 3 parts by mass or less.
- the content ratio of the hole transport material (HTM) to the binder resin is 40 parts by mass of the hole transport material (HTM) with respect to 100 parts by mass of the binder resin, from the viewpoint of the hole transport property. It is preferably 70 parts by mass or more, more preferably 90 parts by mass or more.
- the amount is preferably 200 parts by mass or less, more preferably 150 parts by mass or less, and more preferably 120 parts by mass or less.
- the content ratio of the electron transport material (ETM) to the binder resin is 20 parts by mass or more for 100 parts by mass of the binder resin, from the viewpoint of electron transport properties. is preferred, especially 35 parts by mass or more, more preferably 50 parts by mass or more.
- the amount is preferably 100 parts by mass or less, more preferably 90 parts by mass or less, and more preferably 80 parts by mass or less.
- the content ratio (mass ratio) of the electron transport material (ETM) to the hole transport material (HTM) is set to
- the electron transport material (ETM) is preferably 0.2 or more, more preferably 0.4 or more, more preferably 0.5 or more.
- it is preferably 1.2 or less, more preferably 1 or less, and more preferably 0.8 or less.
- the thickness of the single-layer type photosensitive layer is usually 15 ⁇ m or more, preferably 20 ⁇ m or more, and more preferably 25 ⁇ m or more. On the other hand, it is usually 50 ⁇ m or less, preferably 40 ⁇ m or less, and more preferably 35 ⁇ m or less.
- charge generating material examples include selenium and its alloys, cadmium sulfide, other inorganic photoconductive materials; phthalocyanine pigments, azo pigments, perylene pigments, Organic pigments such as ring quinone pigments; and various photoconductive materials can be used. Among them, organic pigments are particularly preferred, and phthalocyanine pigments and azo pigments are more preferred.
- metal-free phthalocyanines when a phthalocyanine pigment is used as the charge-generating substance, metal-free phthalocyanines, metals such as copper, gallium, tin, and titanium, or coordinated phthalocyanines such as oxides and halides thereof are used. be able to.
- azo pigment various known bisazo pigments and trisazo pigments are preferably used.
- the charge-generating substance may be used singly, or two or more may be used in any combination and ratio. Furthermore, when two or more kinds of charge-generating substances are used in combination, the charge-generating substances used in combination may be mixed after each other, or may be synthesized, pigmented, crystallized, or otherwise manufactured and processed. You may mix and use in a processing process.
- the particle size of the charge-generating substance in the photosensitive layer is sufficiently small. Specifically, it is usually preferably 1 ⁇ m or less, more preferably 0.5 ⁇ m or less.
- the content of the charge-generating substance in the photosensitive layer is usually preferably 0.1% by mass or more, more preferably 0.5% by mass or more. From the viewpoint of sensitivity and chargeability, it is usually preferably 50% by mass or less, more preferably 20% by mass or less.
- the charge-transporting material used in the photosensitive layer includes a hole-transporting material (HTM) mainly having hole-transporting ability and an electron-transporting material ( ETM). Either one of the hole-transporting substance and the electron-transporting substance may be used alone, or both may be used in combination.
- HTM hole-transporting material
- ETM electron-transporting material
- the hole transport material is not particularly limited as long as it is a known material.
- heterocyclic compounds such as carbazole derivatives, indole derivatives, imidazole derivatives, oxazole derivatives, pyrazole derivatives, thiadiazole derivatives, benzofuran derivatives, aniline derivatives, hydrazone derivatives, arylamine derivatives, stilbene derivatives, butadiene derivatives and enamine derivatives, and their compounds.
- Electron-donating substances such as polymers having groups composed of these compounds in the main chain or side chains, and the like can be mentioned.
- carbazole derivatives Among these, carbazole derivatives, arylamine derivatives, stilbene derivatives, butadiene derivatives, enamine derivatives, and combinations of multiple types of these compounds are preferred. Furthermore, among these, arylamine derivatives or enamine derivatives are more preferable from the viewpoint of electrical properties.
- the electron transport material is not particularly limited as long as it is a known material.
- aromatic nitro compounds such as 2,4,7-trinitrofluorenone, cyano compounds such as tetracyanoquinodimethane, electron-withdrawing substances such as quinone compounds such as diphenoquinone, known cyclic ketone compounds and perylene pigments (perylene derivatives) and the like.
- quinone compounds and perylene pigments (perylene derivatives) are preferred, and quinone compounds are more preferred, from the viewpoint of electrical properties.
- quinone compounds examples include benzoquinone, naphthoquinone, anthraquinone, diphenoquinone, and dinaphthoquinone. Among these, diphenoquinone and dinaphthoquinone are preferable from the viewpoint of electron transport properties.
- the binder resin used for the photosensitive layer is not particularly limited.
- acrylic acid ester resin; methacrylic acid ester resin; polyvinyl butyral resin; polyarylate resin; polyamide resin; polycarbonate resin; etc. can be mentioned.
- the resin may be modified with a silicon reagent or the like. One of these may be used alone, or two or more of them may be used in any ratio and combination.
- polyarylate resins, polycarbonate resins, and polyester resins are preferred from the viewpoint of compatibility with the hole-transporting substance and the electron-transporting substance, and polyarylate resins and polycarbonate resins are more preferred from the viewpoint of electrical properties.
- binder resins used in the photosensitive layer bisphenol or a polycarbonate resin containing a biphenol component and a polyarylate resin are preferable from the viewpoint of sensitivity and residual potential, and from the viewpoint of suppressing mixing of the protective layer (outermost layer) and the photosensitive layer.
- Polycarbonate resins and polyarylate resins containing a bisphenol component are preferable from the viewpoint of mobility, and polycarbonate resins containing a bisphenol component are more preferable from the viewpoint of mobility.
- the hydrocarbon structure X and the formula (A' ) in the same molecule and the SP value of the binder resin forming the photosensitive layer in contact with the protective layer (outermost layer) is preferably 2 or more, especially 3 Above, among them, it is more preferable to be 4 or more.
- the viscosity-average molecular weight of the binder resin forming the photosensitive layer in contact with the protective layer (outermost layer) is preferably 30,000 or more, more preferably 40,000 or more.
- the viscosity average molecular weight is preferably 100,000 or less, more preferably 70,000 or less.
- the Martens hardness of the binder resin forming the photosensitive layer in contact with the protective layer (outermost layer) is preferably 120 N/mm 2 or higher, more preferably 130 N/mm 2 or higher, and even more preferably 140 N/mm 2 or higher.
- the Martens hardness is preferably 220 N/mm 2 or less, more preferably 210 N/mm 2 or less, and even more preferably 200 N/mm 2 or less.
- the elastic deformation rate of the binder resin forming the photosensitive layer in contact with the protective layer (outermost layer) is preferably 36% or higher, more preferably 38% or higher, and even more preferably 40% or higher.
- the elastic deformation rate is preferably 55% or less, more preferably 50% or less.
- the Martens hardness and elastic deformation rate mean values obtained by the following method.
- the Martens hardness and elastic deformation rate can be measured under an environment of a temperature of 25° C. and a relative humidity of 50% using a micro hardness tester FISCHERSCOPE HM2000 manufactured by Fischer.
- a Vickers quadrangular pyramid diamond indenter with a facing angle of 136° is used for the measurement.
- the measurement conditions are set as follows, and the load applied to the indenter and the indentation depth under the load are continuously read to obtain profiles plotted on the Y and X axes as shown in FIG. ⁇ Measurement conditions> Maximum push load: 0.2mN Time required for loading: 10 seconds Time required for unloading: 10 seconds
- the elastic deformation rate is a value defined by the following equation and is the ratio of the work done by the membrane elastically during unloading to the total work required for indentation.
- Elastic deformation rate (%) (We/Wt) x 100
- the total work Wt (nJ) is the area surrounded by ABDDA in FIG. 2
- the elastic deformation work We (nJ) is the area surrounded by CBD. indicates The larger the elastic deformation rate, the more difficult it is for deformation to remain under load, and an elastic deformation rate of 100 means that no deformation remains.
- the photosensitive layer (including both single-layer type and laminated type) is used to improve film-forming properties, flexibility, coating properties, stain resistance, gas resistance, light resistance, etc.
- Additives such as well-known antioxidants, plasticizers, ultraviolet absorbers, electron-withdrawing compounds, leveling agents, and visible light shielding agents may be contained. These may be used in the photosensitive layer individually, or two or more of them may be used in an arbitrary ratio and combination. In particular, it is preferable to contain an antioxidant and an electron-withdrawing compound.
- An antioxidant is a kind of stabilizer used to prevent oxidation of the present electrophotographic photoreceptor.
- Any antioxidant may be used as long as it functions as a radical scavenger, and specifically, phenol derivatives, amine compounds, vitamins, and the like are preferable. Hindered phenols or trialkylamine derivatives having a bulky substituent near the hydroxyl group are more preferable. Antioxidants can be used singly or in combination of two or more.
- the amount of the antioxidant used is not particularly limited, but is 0.1 parts by mass or more, preferably 1 part by mass or more, per 100 parts by mass of the binder resin in the photosensitive layer. In order to obtain good electrical properties and printing durability, the amount is preferably 25 parts by mass or less, more preferably 20 parts by mass or less.
- the present electrophotographic photoreceptor may contain an electron-withdrawing compound.
- the electron-withdrawing compound include sulfonate ester compounds, carboxylate ester compounds, organic cyano compounds, nitro compounds, aromatic halogen derivatives, and the like. Preferred are sulfonate ester compounds and organic cyano compounds. and particularly preferably sulfonic acid ester compounds.
- the electron-withdrawing compound may be used singly, or two or more of them may be used in any ratio and combination.
- the amount of the electron-withdrawing compound used in the present electrophotographic photoreceptor is not particularly limited.
- the electron withdrawing compound is used in the photosensitive layer, it is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more based on 100 parts by mass of the binder resin contained in the photosensitive layer.
- it is usually preferably 50 parts by mass or less, more preferably 40 parts by mass or less, and even more preferably 30 parts by mass or less.
- a method for forming the photosensitive layer is not particularly limited.
- a coating liquid obtained by dissolving (or dispersing) a charge-generating substance, a charge-transporting substance, a binder resin, and other substances in a solvent (or dispersion medium) is applied onto a conductive support (such as an undercoat layer described later).
- a conductive support such as an undercoat layer described later.
- the solvent or dispersion medium used for forming the photosensitive layer is not particularly limited.
- alcohols such as methanol, ethanol, propanol and 2-methoxyethanol
- ethers such as tetrahydrofuran, 1,4-dioxane and dimethoxyethane
- aromatic hydrocarbons such as benzene, toluene, xylene and anisole
- dichloromethane and chloroform for example, alcohols such as methanol, ethanol, propanol and 2-methoxyethanol
- ethers such as tetrahydrofuran, 1,4-dioxane and dimethoxyethane
- aromatic hydrocarbons such as benzene, toluene, xylene and anisole
- dichloromethane and chloroform such as benzene, toluene, xylene and anisole
- One of these may be used alone, or two or more of them may be used in combination in an arbitrary ratio and combination.
- Examples of the method of applying the coating liquid for forming the photosensitive layer include a spray coating method, a spiral coating method, a ring coating method, and a dip coating method.
- the viscosity of the coating liquid or dispersion is preferably 50 mPa ⁇ s or more, more preferably 100 mPa ⁇ s or more. Also, it is preferably 700 mPa ⁇ s or less, more preferably 500 mPa ⁇ s or less. As a result, a photosensitive layer having excellent uniformity in film thickness can be obtained.
- the coating film is dried, and it is preferable to adjust the drying temperature and time so that necessary and sufficient drying is performed.
- the drying temperature is usually 80° C. or higher, preferably 90° C. or higher, more preferably 100° C. or higher, from the viewpoint of suppressing residual solvent. From the viewpoints of prevention of bubble generation and electrical properties, the temperature is usually 250° C. or lower, preferably 170° C. or lower, more preferably 140° C. or lower, and the temperature may be changed stepwise.
- a hot air dryer, a steam dryer, an infrared dryer, a far infrared dryer, or the like can be used.
- only air drying at room temperature may be performed after coating the photosensitive layer, and heat drying may be performed by the above method after coating the protective layer (outermost layer).
- the protective layer (outermost layer) is a layer containing a predetermined polymer, and is preferably a layer cured by irradiation with ultraviolet light and/or visible light.
- the protective layer contains a polymer having a structure represented by formula (a) below.
- X represents a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure is an alkylene structure, alkenylene structure or alkynylene structure.
- a 1 and A 2 each independently represent the following formula (A).
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by the following formula (2), and at least R 11 to R 13 Two are groups represented by the following formula (2).
- Z 1 indicates a bond with an arbitrary atom.
- R21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (A) bond.
- Z3 indicates a bond with an arbitrary atom.
- the protective layer has a partial structure represented by the following formula (b) and a partial structure represented by the following formula (A). Contains coalescence.
- X represents a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure is an alkylene structure, alkenylene structure or alkynylene structure.
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by the following formula (2), and at least R 11 to R 13 Two are groups represented by the following formula (2).
- Z 1 indicates a bond with an arbitrary atom.
- R21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (A) bond.
- Z3 indicates a bond with an arbitrary atom.
- the protective layer contains a partial structure X below and a polymer having a partial structure represented by formula (B) below.
- X represents a hydrocarbon structure having 4 or more and 20 or less carbon atoms, and the hydrocarbon structure is an alkylene structure, an alkenylene structure or an alkynylene structure.
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, a group represented by the following formula (2) or a group represented by the following formula (3) and at least two of R 11 to R 13 are a group represented by the following formula (2) or a group represented by the following formula (3).
- R 14 and R 15 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- R16 is a single bond or an oxygen atom.
- R17 is a single bond.
- n11 represents an integer of 1 or more and 10 or less.
- Z4 indicates a bond with an arbitrary atom.
- R21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (B) bond.
- Z3 indicates a bond with an arbitrary atom.
- R 31 to R 33 each independently represent a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by formula (2) above, and at least R 31 to R 33 Two represent groups represented by the above formula (2).
- R 34 to R 37 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n 31 and n 32 each independently represent an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (B) bond.
- the present electrophotographic photoreceptor can achieve both suppression of image flow and maintenance of electrical properties, and has Martens hardness and elastic deformation rate. becomes good.
- the conventional photoreceptor which has a (meth)acrylic monomer-curable protective layer containing a cured product of (meth)acrylic monomer as the outermost layer of the photoreceptor, suffers from image deletion (image blurring) in a high-humidity environment. ) occurred.
- the reason why the conventional (meth)acrylic monomer-curable protective layer causes image deletion in a high humidity environment is considered as follows.
- the acrylic resin portion in the protective layer absorbs moisture, hydrogen ions or hydroxide ions that form water molecules increase the ionic conductivity and lower the surface resistance of the photoreceptor. As a result, the charges in the unexposed areas of the photoreceptor surface move, and the contrast between the exposed and unexposed areas decreases, causing the electrostatic latent image formed by the charges to flow (image blurring). ).
- the polymer contained in the protective layer (outermost layer) of the present electrophotographic photoreceptor has the structure X (hereinafter also referred to as hydrocarbon structure X), that is, an alkylene structure, alkenylene structure or alkynylene structure with low polarity.
- the amount of water absorbed is small even in a high-humidity environment. Therefore, it is possible to suppress the movement of the electric charge charged in the unexposed area of the photoreceptor surface, so that the contrast between the exposed area and the unexposed area does not decrease, and the electrostatic latent image can be prevented from flowing. it is conceivable that.
- some monomers having a structure in which a (meth)acrylic monomer structure with low moisture absorption, such as a substituent having a (meth)acryloyl group, is bonded to the protective layer (outermost layer) have poor electrical properties. It turns out that there are cases. The reason for this is that if the low hygroscopic structure and the components contained in the photosensitive layer (e.g., hole-transporting substance, electron-transporting substance, binder resin, etc.) have a high affinity, the components of both layers will be separated between the two layers. is formed (referred to as a "mixed layer"), which inhibits charge transport from the photosensitive layer to the protective layer (outermost layer).
- a mixed layer which inhibits charge transport from the photosensitive layer to the protective layer (outermost layer).
- the polymer contained in the protective layer (outermost layer) of the present electrophotographic photoreceptor has a partial structure (the above formula (A) or formula (B) ), and this structure of formula (A) or formula (B) can be positioned around the less polar skeleton to provide steric protection.
- the polymer can be prevented from being mixed with the components contained in the photosensitive layer, the formation of a mixed layer can be prevented, and charge transport from the photosensitive layer to the protective layer (outermost layer) can be sufficiently performed. it is conceivable that.
- the polymer is preferably the main component polymer of the protective layer (outermost layer). That is, the polymer is preferably a polymer having the highest mass ratio among the polymers constituting the protective layer (outermost layer), and the total weight of the polymer constituting the protective layer (outermost layer) 50% or more, especially 70% or more, especially 80% or more, especially 90% or more, especially 95% or more (including 100%).
- the polymer contained in the protective layer preferably contains the hydrocarbon structure X in one molecule at a rate of 6 wt% or more, especially 10 wt%. Above all, it is more preferable to contain at a rate of 12 wt % or more.
- the hydrocarbon structure X is preferably contained in one molecule at a rate of 30 wt % or less, preferably 22 wt % or less, and more preferably 18 wt % or less. is more preferred.
- the protective layer (outermost layer) of the present electrophotographic photoreceptor shown in the first to third embodiments above include an aliphatic dicarboxylic acid or an aliphatic dicarboxylic acid chloride,
- a layer containing a polymer obtained by polymerizing a reaction product of a hydric alcohol and at least one selected from the group consisting of acrylic acid, methacrylic acid, acrylic acid chloride and methacrylic acid chloride can be mentioned. More specifically, a layer containing a polymer obtained by radically polymerizing a reactant obtained by reacting an aliphatic dicarboxylic acid, a polyhydric alcohol, and acrylic acid or methacrylic acid by dehydration condensation. can be done.
- the reactant to be radically polymerized is an alcohol obtained by condensing a polyhydric alcohol with acrylic acid or methacrylic acid, acrylic acid chloride or methacrylic acid chloride in advance, and an aliphatic dicarboxylic acid or an aliphatic dicarboxylic acid chloride. It may be a reaction product obtained by
- the aliphatic dicarboxylic acid preferably has 4 or more carbon atoms, more preferably 5 or more carbon atoms, and even more preferably 7 or more carbon atoms.
- those having 16 or less carbon atoms are preferable, those having 12 or less carbon atoms are more preferable, and those having 10 or less carbon atoms are even more preferable.
- the number of carbon atoms referred to here does not include the number of carbon atoms constituting the carboxylic acid.
- aliphatic dicarboxylic acids include adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, Heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, icosanedioic acid, henicosanedioic acid, docosanedioic acid, 3-methyl-1,6-butanedicarboxylic acid, 4-methyl-1,7-pentanedicarboxylic acid, dihydromuconic acid , 2,4-hexadiene-1,6-dicarboxylic acid, acetylenedicarboxylic acid, 1,4
- adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tetradecanedioic acid, and 1,4-cyclohexanedicarboxylic acid are preferred from the viewpoint of electrical properties and image flow. From the viewpoint of properties, adipic acid, suberic acid, azelaic acid, and sebacic acid are more preferable.
- the aliphatic dicarboxylic acid chloride it is preferable to have a dicarboxylic acid chloride having the same structure as the aliphatic dicarboxylic acid.
- the polyhydric alcohol preferably has 2 to 12 carbon atoms, more preferably has 3 to 10 carbon atoms, further preferably has 4 to 6 carbon atoms, and has 3 or more hydroxyl groups. is preferred, and 4 or more is more preferred.
- Specific examples of polyhydric alcohols include pentaerythritol, dipentaerythritol, trimethylolethane, and trimethylolpropane. Among them, pentaerythritol or dipentaerythritol is preferable from the viewpoint of suppressing mixing of the protective layer (outermost layer) and the photosensitive layer, and pentaerythritol is more preferable from the viewpoint of suppressing image flow.
- X is a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure is an alkylene structure, alkenylene structure or alkynylene structure.
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, a group represented by the following formula (2) or a group represented by the following formula (3). At least two of R 11 to R 13 are a group represented by the following formula (2) or a group represented by the following formula (3).
- R 14 and R 15 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- R16 is a single bond or an oxygen atom.
- R17 is a single bond.
- n12 is 2 and n11 represents an integer of 1 or more and 10 or less.
- R21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (1) bond, and Z 3 represents a bond with an arbitrary atom.
- R 31 to R 33 each independently represent a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by formula (2) above. At least two of R 31 to R 33 represent groups represented by formula (2) above.
- R 34 to R 37 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n 31 and n 32 each independently represent an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in formula (1) bond.
- the structure X represents a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure may be an alkylene structure, an alkenylene structure, or an alkynylene structure. Among these, an alkylene structure is preferable from the viewpoint of hydrophobicity.
- the hydrocarbon structure X may have a chain structure or a cyclic structure. When the hydrocarbon structure X is a chain structure, it may be linear or branched containing a side chain. Moreover, from the viewpoint of hydrophobicity, it is preferably composed of carbon and hydrogen. When the hydrocarbon structure X is a cyclic structure, it preferably has a cyclo ring.
- the number of carbon atoms in the hydrocarbon structure X may be 4 or more and 20 or less, and the lower limit is preferably 5 or more, more preferably 6 or more, and even more preferably 7 or more. On the other hand, the upper limit is preferably 16 or less, more preferably 12 or less, and even more preferably 10 or less.
- a 1 and A 2 each independently represent the formula (A).
- Preferred embodiments of formula (A) are as described below. Since A 1 and A 2 each independently represent formula (A), R 11 to R 13 and R 21 to R 23 in A 1 and A 2 may or may not be the same. may be Hereinafter, when a plurality of groups are defined as "independently", the substituents possessed by the plurality of groups may be the same or different from each other.
- examples of hydrocarbon groups for R 11 , R 12 and R 13 include aliphatic hydrocarbon groups and aromatic hydrocarbon groups.
- examples of the aliphatic hydrocarbon group include alkyl groups, alkenyl groups and alkynyl groups.
- the number of carbon atoms in the aliphatic hydrocarbon group is not particularly limited, but the alkyl group is usually 1 or more, and the alkenyl and alkynyl groups are usually 2 or more.
- all of the alkyl group, alkenyl group and alkynyl group are preferably 20 or less, more preferably 10 or less, and particularly preferably 6 or less.
- aliphatic hydrocarbon group examples include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, sec-butyl group, i-butyl group, tert-butyl group, n- pentyl group, isopentyl group, sec-pentyl group, neopentyl group, 1-methylbutyl group, 2-methylbutyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, vinyl group, 1-propenyl group, 2- propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-buty
- aromatic hydrocarbon group examples include an aryl group and an aralkyl group.
- the number of carbon atoms in the aromatic hydrocarbon group is not particularly limited, it is usually 6 or more, and usually 20 or less, preferably 12 or less. By setting it as the said range, it is excellent in solubility and an electrical property.
- aromatic hydrocarbon group examples include phenyl, tolyl, xylyl, ethylphenyl, n-propylphenyl, i-propylphenyl, n-butylphenyl, sec-butylphenyl, i -butylphenyl, tert-butylphenyl, naphthyl, anthracene, biphenyl and pyrene groups.
- alkoxy groups for R 11 , R 12 and R 13 include methoxy, ethoxy, propoxy, butoxy and phenoxy groups.
- R 11 , R 12 and R 13 are groups represented by the formula ( 2 ). and R 13 are preferably groups represented by formula (2).
- R 11 , R 12 and R 13 are groups represented by formula (2) or groups represented by formula (3).
- R 11 , R 12 , and R 13 are each preferably a group represented by formula (2) or a group represented by formula (3), from the viewpoint of film strength after reaction. Details of formulas (2) and (3) will be described later.
- R 14 and R 15 are each independently a hydrogen atom, a hydrocarbon group or an alkoxy group. A group similar to can be mentioned.
- R 14 and R 15 are preferably hydrogen atoms from the viewpoint of solvent solubility.
- R 16 and R 17 are a single bond and an oxygen atom, and from the viewpoint of electrical properties, it is preferred that R 16 is an oxygen atom and R 17 is a single bond.
- n11 is an integer of 1 or more and 10 or less, preferably 6 or less, more preferably 4 or less, and most preferably 1 from the viewpoint of solvent solubility.
- n12 is 2 from the viewpoint of solubility and film strength after reaction.
- X is a hydrocarbon structure having 4 or more and 20 or less carbon atoms, and the above content can be applied to the hydrocarbon structure and its carbon number.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group. can be mentioned.
- n 21 , n 31 and n 32 are each an integer of 1 or more and 10 or less, usually 1 or more and usually 10 or less, preferably 6 or less, more preferably 4 or less. and 1 is most preferable from the viewpoint of solvent solubility.
- R 31 , R 32 and R 33 each independently represent a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group or a group represented by formula (2); At least two of R 33 represent groups represented by the above formula (2).
- examples of the hydrocarbon group and the alkoxy group include the same groups as those described for R 11 to R 13 .
- R 34 , R 35 , R 36 and R 37 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group. Specific examples include the same groups as those described above for R 11 to R 13 .
- the polymer in the first embodiment of the present invention is preferably a polymer of a compound represented by formula (a') described below.
- the polymer in the second embodiment of the present invention is a polymer of a compound having, in the same molecule, the partial structure represented by the formula (b) and the partial structure represented by the formula (A') described later. It is preferable to have In the polymer, the partial structure represented by the formula (b) and the partial structure represented by the formula (A') may be randomly present in the molecule.
- the partial structure represented by is preferably the skeleton of the polymer, that is, the structure of the main chain rather than the substituents.
- the polymer in the third embodiment of the present invention is preferably a polymer of a compound having, in the same molecule, the hydrocarbon structure X and a partial structure represented by formula (B') described later.
- the hydrocarbon structure X and the partial structure represented by the formula (B′) may be present randomly in the molecule. That is, it is preferably the structure of the main chain rather than the substituent.
- X represents a hydrocarbon structure having 4 to 20 carbon atoms, and the hydrocarbon structure is an alkylene structure, alkenylene structure or alkynylene structure.
- a 1 and A 2 each independently represent the following formula (A').
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by the following formula ( 2'); At least two of them are groups represented by the following formula (2').
- Z 1 indicates a bond with an arbitrary atom.
- R21 represents a hydrogen atom or a methyl group.
- R 22 and R 23 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- n21 represents an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in the formula (A') are bonded.
- R 11 to R 13 and R 21 to R 23 in formulas (A′) and (2′) and n 21 are R 11 to R 11 in formulas (A) and (2). Same as R 13 and R 21 to R 23 and n 21 .
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, a group represented by the above formula (2'), or a group represented by the following formula (3'). and at least two of R 11 to R 13 are a group represented by the above formula (2′) or a group represented by the following formula (3′).
- R 14 and R 15 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- R16 is a single bond or an oxygen atom.
- R17 is a single bond.
- n11 represents an integer of 1 or more and 10 or less.
- Z4 indicates a bond with an arbitrary atom.
- R 31 , R 32 , and R 33 each independently represent a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, or a group represented by formula (2′) above, and R 31 At least two of to R 33 represent a group represented by the above formula (2′).
- R 34 to R 37 represent a hydrogen atom, a hydrocarbon group or an alkoxy group, and n 31 and n 32 each independently represent an integer of 1 or more and 10 or less.
- Z 2 represents a bond with the carbon atom to which R 11 to R 13 in the formula (1′) are bonded.
- the raw material for the polymer in the fourth embodiment of the present invention is a reaction product of an aliphatic dicarboxylic acid or an aliphatic dicarboxylic acid chloride, a polyhydric alcohol, and acrylic acid or methacrylic acid or acrylic acid chloride or methacrylic acid chloride is.
- a compound obtained by reacting an aliphatic dicarboxylic acid, a polyhydric alcohol, and acrylic acid or methacrylic acid by dehydration condensation or a polyhydric alcohol and acrylic acid or methacrylic acid or acrylic acid chloride or methacrylic acid chloride in advance with an alcohol compound obtained by condensing with an aliphatic carboxylic acid or a compound obtained by condensation reaction of an aliphatic carboxylic acid chloride.
- the raw material of the polymer in the fifth embodiment of the present invention that is, the polymer having the structure represented by the formula (1). It is preferably obtained by polymerizing a compound having a structure represented by the following formula (1').
- X represents an alkylene structure, an alkenylene structure, or an alkynylene structure.
- R 11 to R 13 are each independently a hydrogen atom, a hydrocarbon group, an alkoxy group, a methylol group, a group represented by the above formula (2') or a group represented by the above formula (3'). At least two of R 11 to R 13 are the group represented by the above formula (2′) or the group represented by the above formula (3′).
- R 14 and R 15 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group, and R 16 is a single bond or an oxygen atom.
- R17 is a single bond.
- n12 is 2 and n11 represents an integer of 1 or more and 10 or less.
- R 11 to R 17 , R 21 to R 23 and R 31 to R 37 , n 11 , n 21 , n 31 and n 32 in formulas (B), (2) and (3) above. are the same.
- Formula (2') has an acryloyl group or a methacryloyl group, which is a chain polymerizable functional group. Therefore, each of the above-described compounds, which are raw materials of the polymer contained in the protective layer (outermost layer), has a plurality of acryloyl groups or methacryloyl groups. From this, it is considered that intermolecular cross-linking occurs at a high density due to the polymerization reaction, and a cured film having excellent mechanical strength is formed.
- the water absorption rate of each compound described above which is a raw material of the polymer contained in the protective layer (outermost layer), is preferably 0.1% or more. 0.2% or more is more preferable, and 0.3% or more is even more preferable. On the other hand, from the viewpoint of suppressing image deletion, it is preferably 1.5% or less, more preferably 1.3% or less, and even more preferably 1.0% or less.
- the water absorption rate can be measured by the method described in the examples below.
- the following compounds (1-1) to (1-6) are preferable from the viewpoint of solubility and electrical properties, and compounds (1-1) to (1-5) are more preferable from the viewpoint of electrical properties. is preferred, and compound (1-2) is particularly preferred.
- the polymer contained in the protective layer (outermost layer) may be polymerized by a method such as radical polymerization in which a reaction is initiated by applying energy such as heat, light, or radiation to the raw materials described above.
- a method such as radical polymerization in which a reaction is initiated by applying energy such as heat, light, or radiation to the raw materials described above.
- energy such as heat, light, or radiation
- each of the above-mentioned polymers contained in the protective layer (outermost layer) should further have a "partial structure having charge-transporting ability" from the viewpoint of improving the mechanical strength and charge-transporting property of the protective layer (outermost layer). is preferred.
- each of the above-mentioned polymers contained in the protective layer (outermost layer) further has a "partial structure having charge-transporting ability".
- Examples of the chain polymerizable functional group of the charge transport material having the chain polymerizable functional group include acryloyl group, methacryloyl group, vinyl group and epoxy group. Among these, an acryloyl group or a methacryloyl group is preferable from the viewpoint of curability.
- Examples of the structure of the charge-transporting substance portion of the charge-transporting substance having the chain-polymerizable functional group, that is, the partial structure of the polymer having charge-transporting ability include carbazole derivatives, indole derivatives, imidazole derivatives, oxazole derivatives, pyrazole derivatives, and thiadiazole derivatives.
- heterocyclic compounds such as benzofuran derivatives, aniline derivatives, hydrazone derivatives, arylamine derivatives, stilbene derivatives, butadiene derivatives and enamine derivatives, and combinations of multiple types of these compounds, and groups consisting of these compounds in the main chain or
- a structure derived from an electron-donating substance such as a polymer having a side chain can be mentioned.
- structures derived from carbazole derivatives, arylamine derivatives, stilbene derivatives, butadiene derivatives, enamine derivatives, and combinations of multiple types of these compounds are preferred, and structures derived from arylamine derivatives. is more preferred.
- a triarylamine structure is preferable as the structure derived from the arylamine derivative.
- the content ratio (mass ratio) of the hydrocarbon structure X to the triarylamine structure is preferably 0.2 or more and 4 or less, and more preferably 0.4 or more. is preferred, and 2 or less is more preferred.
- Each of the aforementioned polymers contained in the protective layer (outermost layer) preferably further has a structure represented by the following formula (4).
- Ar 41 to Ar 43 are aromatic groups.
- R 41 to R 43 are each independently a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, a halogenated alkyl group, a halogen atom, a benzyl group, or a group represented by the following formula (5).
- n 41 to n 43 are each independently an integer of 1 or more. However, when n 41 is 1, R 41 is a group represented by formula (5), and when n 41 is an integer of 2 or more, 2 or more R 41 may be the same or different. Good, but at least one is a group represented by formula (5). When n 42 is an integer of 2 or more, two or more R 42 may be the same or different. When n 43 is an integer of 2 or more, two or more R 43 may be the same or different.
- R 51 represents a hydrogen atom or a methyl group
- R 52 and R 53 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group
- R 54 represents a single bond or an oxygen atom
- n51 represents an integer of 0 or more and 10 or less.
- Z 2 represents a bond with Ar 41 to Ar 43 in the formula (4)
- Z 3 represents a bond with an arbitrary atom.
- Ar 41 to Ar 43 are aromatic groups.
- R 41 to R 43 are each independently a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, a halogenated alkyl group, a halogen atom, a benzyl group, or the above formula (5).
- the number of carbon atoms in the alkyl group, alkoxy group, and halogenated alkyl group is usually 1 or more, while usually 10 or less, preferably 8 or less, more preferably 6 or less, and still more preferably 4 or less.
- alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, isobutyl group, cyclohexyl group and the like.
- alkoxy groups include methoxy, ethoxy, propoxy, and cyclohexoxy groups.
- aryl group examples include a phenyl group and a naphthyl group.
- a chloroalkyl group, a fluoroalkyl group, etc. can be mentioned as a halogenated alkyl group.
- a fluorine atom, a chlorine atom, a bromine atom, etc. can be mentioned as a halogen atom. More preferred are methyl group, ethyl group and phenyl group.
- n 41 to n 43 are each independently an integer of 1 or more, usually 1 or more, usually 5 or less, preferably 3 or less, with 1 being most preferred.
- R 41 is a group represented by formula (5)
- n 41 is an integer of 2 or more
- 2 or more R 41 may be the same or different.
- At least one is preferably a group represented by formula (5).
- n 42 is an integer of 2 or more
- two or more R 42 may be the same or different
- n 43 is an integer of 2 or more, two or more 43 may be the same can be different.
- n 41 to n 43 are 1, R 41 is a group represented by formula (5), and one of R 42 and R 43 is represented by formula (5). or a group where n 41 to n 43 are 1 and R 41 to R 43 are groups represented by formula (5).
- R 41 to n 43 are 1, R 41 is a group represented by formula (5), and one of R 42 and R 43 is a group represented by formula (5). Some cases are more preferable.
- n51 is an integer of 0 or more and 10 or less, usually 0 or more, usually 10 or less, preferably 6 or less, more preferably 4 or less, and still more preferably 3 or less.
- a compound having a structure represented by the following formula (4') is preferable as the charge-transporting substance having the chain polymerizable functional group.
- Ar 41 to Ar 43 are aromatic groups.
- R 41 to R 43 are each independently a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, a halogenated alkyl group, a halogen atom, a benzyl group, or a group represented by the following formula (5').
- n 41 to n 43 are each independently an integer of 1 or more. However, when n 41 is 1, R 41 is a group represented by formula (5′), and when n 41 is an integer of 2 or more, two or more R 41 are the same or different. but at least one is a group represented by formula (5'). When n 42 is an integer of 2 or more, two or more R 42 may be the same or different, and when n 43 is an integer of 2 or more, two or more R 43 may be the same may also be different.
- R51 represents a hydrogen atom or a methyl group.
- R 52 and R 53 each independently represent a hydrogen atom, a hydrocarbon group or an alkoxy group.
- R54 represents a single bond or an oxygen atom.
- n51 represents an integer of 0 or more and 10 or less.
- Z 2 represents a bond with Ar 41 to Ar 43 in formula (4').
- formula (4-1), formula (4-2), formula (4-3), formula (4-4), formula (4-6), formula (4) -7) are preferable, and compounds represented by formulas (4-1), (4-2) and (4-3) are more preferable.
- each of the above-described polymers contained in the protective layer (outermost layer) further has a structure represented by formula (4)
- the structure represented by formula (4) is represented by formula (A )
- the content ratio (mass ratio) of the structure represented by formula (B) or formula (1) is usually 0.2 or more, preferably 0.4 or more, and usually 4 or less, preferably 2 or less.
- Each of the aforementioned polymers contained in the protective layer (outermost layer) may further have other partial structures from the viewpoint of adjusting the mechanical strength of the protective layer (outermost layer).
- the raw material for such a polymer is not particularly limited, but for example, it can be obtained by polymerizing each of the compounds described above, which are raw materials for the polymer contained in the protective layer (outermost layer), and a compound having a chain-polymerizable functional group. preferable.
- chain-polymerizable functional groups of compounds having chain-polymerizable functional groups include acryloyl groups, methacryloyl groups, vinyl groups, and epoxy groups.
- the compound having a chain polymerizable functional group is not particularly limited as long as it is a known material, but from the viewpoint of curability, a monomer, oligomer, or polymer having an acryloyl group or a methacryloyl group is preferable.
- TMPTA Trimethylolpropane triacrylate
- HPA-modified trimethylolpropane triacrylate Trimethylolpropane triacrylate
- EO-modified trimethylolpropane triacrylate Trimethylolpropane triacrylate
- PO-modified trimethylolpropane triacrylate PO-modified trimethylolpropane triacrylate
- caprolactone-modified trimethylolpropane triacrylate HPA-modified trimethylolpropane triacrylate
- Methylolpropane trimethacrylate pentaerythritol triacrylate, pentaerythritol tetraacrylate
- glycerol triacrylate ECH-modified glycerol triacrylate
- EO-modified glycerol triacrylate PO-modified glycerol triacrylate
- tris(acryloxyethyl) isocyanurate caprolactone-modified tris ( acryl
- Urethane acrylates include "EBECRYL (registered trademark) 8301”, “EBECRYL1290”, “EBECRYL1830”, “KRM8200” (manufactured by Daicel Allnex Co., Ltd.), "UV1700B”, “UV7640B”, “UV7605B”, and “UV6300B.” , "UV7550B” (manufactured by Mitsubishi Chemical Corporation), and the like.
- ester acrylate examples include “M-7100”, “M-7300K”, “M-8030”, “M-8060”, “M-8100”, “M-8530”, “M-8560”, “M- 9050” (manufactured by Toagosei Co., Ltd.).
- acrylic acrylate examples include “8BR-600”, “8BR-930MB”, “8KX-078”, “8KX-089”, and “8KX-168” (manufactured by Taisei Fine Chemical Co., Ltd.). These may be used singly or in combination of two or more.
- the protective layer (outermost layer) of the present electrophotographic photoreceptor may contain, in addition to the above-described polymers, a charge transport substance or metal oxide particles for the purpose of imparting charge transport ability. Moreover, a polymerization initiator may be contained in order to accelerate the polymerization reaction. In addition, for the purpose of reducing frictional resistance and abrasion on the surface of the electrophotographic photosensitive member, the protective layer (outermost layer) may contain a fluororesin, a silicone resin, or the like. Particles may be included.
- charge-transporting substances, metal oxide particles, and polymerization initiators will be described in detail as "materials other than the polymer” that may be contained in the protective layer (outermost layer). These materials include those used as raw materials for forming the protective layer (outermost layer).
- charge transport material As the charge-transporting substance contained in the protective layer (outermost layer), the same charge-transporting substance as used in the photosensitive layer can be used.
- the amount of the charge-transporting substance used in at least one protective layer (outermost layer) of the electrophotographic photoreceptor is not particularly limited. From the viewpoint of electrical properties, the amount is preferably 10 parts by mass or more, more preferably 30 parts by mass or more, and particularly preferably 50 parts by mass or more with respect to 100 parts by mass of the binder resin. From the viewpoint of maintaining good surface resistance, the amount is preferably 300 parts by mass or less, more preferably 200 parts by mass or less, and particularly preferably 150 parts by mass or less.
- charge-transporting material as used herein does not include the aforementioned "charge-transporting material having a chain polymerizable functional group" and the metal oxide particles described below.
- the protective layer may contain metal oxide particles from the viewpoint of imparting charge transport ability and improving mechanical strength.
- metal oxide particles any metal oxide particles that can be used in an electrophotographic photoreceptor can be used.
- metal oxide particles more specifically, metal oxide particles containing one metal element such as titanium oxide, tin oxide, aluminum oxide, silicon oxide, zirconium oxide, zinc oxide and iron oxide, calcium titanate, Metal oxide particles containing a plurality of metal elements such as strontium titanate and barium titanate can be mentioned. Among these, metal oxide particles having a bandgap of 2 to 4 eV are preferred.
- metal oxide particles only one type of particles may be used, or a plurality of types of particles may be mixed and used. Among these metal oxide particles, titanium oxide, tin oxide, aluminum oxide, silicon oxide, and zinc oxide are preferred, and titanium oxide and tin oxide are more preferred. Titanium oxide is particularly preferred.
- Any of rutile, anatase, brookite, and amorphous can be used as the crystal type of titanium oxide particles.
- a plurality of crystalline states may be included from those having different crystalline states.
- Metal oxide particles may be subjected to various surface treatments. For example, it may be treated with inorganic substances such as tin oxide, aluminum oxide, antimony oxide, zirconium oxide and silicon oxide, or with organic substances such as stearic acid, polyols and organosilicon compounds. In particular, when titanium oxide particles are used, they are preferably surface-treated with an organosilicon compound.
- inorganic substances such as tin oxide, aluminum oxide, antimony oxide, zirconium oxide and silicon oxide
- organic substances such as stearic acid, polyols and organosilicon compounds.
- titanium oxide particles are preferably surface-treated with an organosilicon compound.
- organosilicon compounds include silicone oils such as dimethylpolysiloxane and methylhydrogenpolysiloxane, organosilanes such as methyldimethoxysilane and diphenyldidimethoxysilane, silazanes such as hexamethyldisilazane, 3-methacryloyloxypropyltrimethoxysilane, 3 -Silane coupling agents such as acryloyloxypropyltrimethoxysilane, vinyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane and ⁇ -aminopropyltriethoxysilane.
- silicone oils such as dimethylpolysiloxane and methylhydrogenpolysiloxane
- organosilanes such as methyldimethoxysilane and diphenyldidimethoxysilane
- silazanes such as hexamethyldisilazane
- 3-methacryloyloxypropyltrimethoxysilane, 3-acryloyloxypropyltrimethoxysilane, and vinyltrimethoxysilane having a chain polymerizable functional group are preferable from the viewpoint of improving the mechanical strength of the protective layer (outermost layer).
- the outermost surface of these surface-treated particles is treated with such a treating agent, it may be treated with a treating agent such as aluminum oxide, silicon oxide or zirconium oxide prior to the treatment. I do not care.
- the metal oxide particles to be used preferably have an average primary particle diameter of 500 nm or less, more preferably 100 nm or less, still more preferably 50 nm or less, more preferably 1 nm or more, and further preferably 1 nm or more. A thickness of 5 nm or more is preferably used.
- This average primary particle size can be obtained from the arithmetic mean value of the particle sizes directly observed with a transmission electron microscope (hereinafter also referred to as TEM).
- titanium oxide particles include ultrafine titanium oxide "TTO-55 (N)” and “TTO-51 (N)” that are not surface-treated. , Al 2 O 3 coated ultrafine titanium oxide “TTO-55 (A)”, “TTO-55 (B)”, ultrafine titanium oxide surface treated with stearic acid “TTO-55 (C) ”, ultrafine titanium oxide “TTO-55 (S)” surface-treated with Al 2 O 3 and organosiloxane, high-purity titanium oxide “C-EL”, sulfuric acid method titanium oxide “R-550”, “R -580", “R-630", “R-670”, “R-680”, “R-780", "A-100", “A-220", “W-10”, chlorine method titanium oxide "CR-50", “CR-58", “CR-60”, “CR-60-2”, “CR-67”, conductive titanium oxide "ET-300W” (manufactured by Ishihara Sangyo Co., Ltd.) and titanium oxide such as
- silicon oxide particles include “200CF”, “R972” (manufactured by Nippon Aerosil Co., Ltd.), and “KEP-30” (manufactured by Nippon Shokubai Co., Ltd.).
- tin oxide particles include “SN-100P”, “SN-100D” (manufactured by Ishihara Sangyo Co., Ltd.), “SnO 2 ” (manufactured by CIK Nanotech Co., Ltd.), and “S-2000”. , phosphorus-doped tin oxide “SP-2”, antimony-doped tin oxide “T-1”, indium-doped tin oxide “E-ITO” (manufactured by Mitsubishi Materials Corporation), and the like.
- MZ-305S manufactured by Tayca Corporation
- metal oxide particles that can be used in the present invention are not limited to these.
- the content of metal oxide particles in at least one protective layer (outermost layer) of the present electrophotographic photoreceptor is not particularly limited.
- the amount is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, and particularly preferably 30 parts by mass or more with respect to 100 parts by mass of the binder resin.
- the amount is preferably 300 parts by mass or less, more preferably 200 parts by mass or less, and particularly preferably 100 parts by mass or less.
- the content of the metal oxide particles in the protective layer (outermost layer) is 300 parts by mass with respect to 100 parts by mass of the polymer contained in the protective layer (outermost layer). It is preferably 200 parts by mass or less, more preferably 160 parts by mass or less, and even more preferably 120 parts by mass or less.
- the amount is preferably 20 parts by mass or more, more preferably 60 parts by mass or more, and more preferably 80 parts by mass or more.
- Polymerization initiators include thermal polymerization initiators, photopolymerization initiators, and the like.
- thermal polymerization initiators include peroxide compounds such as 2,5-dimethylhexane-2,5-dihydroperoxide and azo compounds such as 2,2′-azobis(isobutyronitrile). can.
- Photopolymerization initiators can be classified into direct cleavage type and hydrogen abstraction type depending on the difference in radical generation mechanism.
- Direct cleavage type photopolymerization initiators generate radicals by partly cleaving the covalent bonds in the molecule upon absorption of light energy.
- hydrogen-abstraction type photopolymerization initiator a molecule excited by absorbing light energy abstracts hydrogen from a hydrogen donor to generate a radical.
- Direct cleavage type photopolymerization initiators include acetophenone, 2-benzoyl-2-propanol, 1-benzoylcyclohexanol, 2,2-diethoxyacetophenone, benzyldimethylketal, 2-methyl-4'-(methylthio)- Acetophenone or ketal compounds such as 2-morpholinopropiophenone, benzoin ether compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin isopropyl ether, O-tosylbenzoin, diphenyl (2,4, 6-trimethylbenzoyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, lithium phenyl(2,4,6-trimethylbenzoyl)phosphonate, and other acylphosphine oxide compounds. be able to.
- Hydrogen abstraction type photopolymerization initiators include benzophenone, 4-benzoylbenzoic acid, 2-benzoylbenzoic acid, methyl 2-benzoylbenzoate, methyl benzoylformate, benzyl, p-anisyl, 2-benzoylnaphthalene, 4, Benzophenone compounds such as 4'-bis(dimethylamino)benzophenone, 4,4'-dichlorobenzophenone, 1,4-dibenzoylbenzene, 2-ethylanthraquinone, 2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4- Examples include anthraquinone-based or thioxanthone-based compounds such as dimethylthioxanthone, 2,4-diethylthioxanthone, and 2,4-dichlorothioxanthone.
- photopolymerization initiators include camphorquinone, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl)oxime, acridine compounds, triazine compounds, imidazole compounds, and the like. .
- the photopolymerization initiator preferably has an absorption wavelength in the wavelength region of the light source used for light irradiation.
- an acylphosphine oxide compound and a hydrogen abstraction type initiator are more preferable to use an acylphosphine oxide compound and a hydrogen abstraction type initiator together.
- the content ratio of the hydrogen abstraction type initiator to the acylphosphine oxide compound is not particularly limited. From the viewpoint of supplementing surface curability, it is preferably 0.1 parts by mass or more per 1 part by mass of the acylphosphine oxide compound, and from the viewpoint of maintaining internal curability, it is preferably 5 parts by mass or less.
- one having a photopolymerization promoting effect can be used alone or in combination with the photopolymerization initiator.
- examples include triethanolamine, methyldiethanolamine, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, (2-dimethylamino)ethyl benzoate, and 4,4'-dimethylaminobenzophenone.
- the content of the polymerization initiator is 0.5 to 40 parts by mass, preferably 1 to 40 parts by mass with respect to 100 parts by mass of the total content having radical polymerizability, as the composition of the raw material forming the protective layer (outermost layer). 20 parts by mass.
- the polymerization initiator is consumed in the process of forming the protective layer (outermost layer).
- a method for forming the protective layer (outermost layer) is not particularly limited. For example, it can be formed by applying a coating liquid in which a binder resin, a charge transporting substance, metal oxide particles, and other substances are dissolved in a solvent or dispersed in a dispersion medium.
- the protective layer (outermost layer) containing the polymer When the protective layer (outermost layer) containing the polymer is formed, a coating liquid obtained by dissolving each of the above-described compounds, which are raw materials of the polymer, in a solvent is applied and polymerized.
- the solvent or dispersion medium used to form the protective layer (outermost layer) and the coating method will be described below.
- organic solvent used in the protective layer (outermost layer) forming coating liquid any organic solvent can be used as long as it can dissolve the substance according to the present invention. Specifically, alcohols such as methanol, ethanol, propanol and 2-methoxyethanol; ethers such as tetrahydrofuran, 1,4-dioxane and dimethoxyethane; esters such as methyl formate and ethyl acetate; acetone, methyl ethyl ketone and cyclohexanone.
- alcohols such as methanol, ethanol, propanol and 2-methoxyethanol
- ethers such as tetrahydrofuran, 1,4-dioxane and dimethoxyethane
- esters such as methyl formate and ethyl acetate
- acetone methyl ethyl ketone and cyclohexanone.
- ketones such as benzene, toluene, xylene, and anisole
- aromatic hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, 1,1,2-trichloroethane, 1,1,1-trichloroethane, tetrachloroethane, 1 , 2-dichloropropane, trichlorethylene and other chlorinated hydrocarbons
- n-butylamine isopropanolamine, diethylamine, triethanolamine, ethylenediamine, triethylenediamine and other nitrogen-containing compounds
- acetonitrile, N-methylpyrrolidone, N,N- Examples include aprotic polar solvents such as dimethylformamide and dimethylsulfoxide.
- Mixed solvents in any combination and any ratio among these can also be used.
- an organic solvent that does not dissolve the substance for the protective layer (outermost layer) according to the present invention by itself can be used if, for example, it can be dissolved in a mixed solvent with the above organic solvent. can be done.
- the use of a mixed solvent can reduce coating unevenness.
- dip coating is used in the coating method described below, it is preferable to select a solvent that does not dissolve the lower layer. From this point of view, it is preferable to contain alcohols that have low solubility in polycarbonates and polyarylates that are suitably used in the photosensitive layer.
- the organic solvent used in the coating solution for forming the protective layer (outermost layer) and the amount of solids differ depending on the method of coating the coating solution for forming the protective layer (outermost layer). It may be used by appropriately changing it so that it is used.
- the method of applying the coating liquid for forming the protective layer (outermost layer) is not particularly limited.
- a spray coating method, a spiral coating method, a ring coating method, a dip coating method, and the like can be used.
- the coating film is dried. At this time, as long as necessary and sufficient drying can be obtained, the drying temperature and time are not critical. However, when the protective layer (outermost layer) is applied only by air-drying after coating the photosensitive layer, it is preferable to dry sufficiently by the method described in [Coating method] of the photosensitive layer described above.
- the thickness of the protective layer (outermost layer) an optimum thickness is appropriately selected depending on the material used. From the viewpoint of life, the thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and particularly preferably 0.5 ⁇ m or more. From the viewpoint of electrical properties, the thickness is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and particularly preferably 3 ⁇ m or less.
- the protective layer (outermost layer) is formed by applying energy from the outside to harden the coating solution after coating.
- the external energy used at this time includes heat, light, and radiation.
- Heat energy can be applied by heating from the coating surface side or the support side using gas such as air, nitrogen, steam, various heat media, infrared rays, or electromagnetic waves.
- the heating temperature is preferably 100° C. or higher and 170° C. or lower. When the temperature is higher than the lower limit temperature, the reaction rate is sufficient and the reaction proceeds completely. When the temperature is equal to or lower than the upper limit temperature, the reaction proceeds uniformly, and the generation of large strain in the protective layer (outermost layer) can be suppressed.
- it is also effective to heat the composition at a relatively low temperature of less than 100°C and then heat it to 100°C or more to complete the reaction.
- UV light sources such as high-pressure mercury lamps, metal halide lamps, electrodeless lamp bulbs, and light-emitting diodes that emit light in ultraviolet (UV) wavelengths can be used. It is also possible to select a visible light source according to the absorption wavelength.
- the light irradiation amount is preferably 0.1 J/cm 2 or more, more preferably 1 J/cm 2 or more, and particularly preferably 10 J/cm 2 or more.
- the light irradiation amount is preferably 200 J/cm 2 or less, more preferably 100 J/cm 2 or less, and particularly preferably 50 J/cm 2 or less.
- Examples of radiation energy include those using electron beams (EB).
- EB electron beams
- those using light energy are preferable from the viewpoint of ease of reaction rate control, simplicity of equipment, and length of pod life.
- a heating step may be added from the viewpoint of alleviating residual stress, alleviating residual radicals, and improving electrical properties.
- the heating temperature is preferably 60° C. or higher, more preferably 100° C. or higher, and preferably 200° C. or lower, more preferably 150° C. or lower.
- the present electrophotographic photoreceptor may have an undercoat layer between the photosensitive layer and the conductive support.
- the undercoat layer for example, a resin, or a resin in which particles such as an organic pigment or a metal oxide are dispersed, or the like is used.
- the organic pigment used in the undercoat layer are not particularly limited.
- phthalocyanine pigments and azo pigments used as the aforementioned charge generation substance can be used.
- 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, and titanium oxide.
- metal oxide particles containing a plurality of metal elements such as strontium oxide and barium titanate can be mentioned.
- For the undercoat layer only one type of particles may be used, or a plurality of types of particles may be mixed and used in an arbitrary ratio and combination.
- titanium oxide and aluminum oxide are preferred, and titanium oxide is particularly preferred.
- the surface of the titanium oxide particles may be treated with an inorganic substance, an organic substance, or the like.
- the particle size of the metal oxide particles used for the undercoat layer is not particularly limited. From the viewpoint of the properties of the undercoat layer and the stability of the solution for forming the undercoat layer, the average primary particle size is preferably 10 nm or more, preferably 100 nm or less, more preferably 50 nm or less.
- the undercoat layer is preferably formed by dispersing particles in a binder resin.
- Binder resins used in the undercoat layer include, for example, polyvinyl butyral resins, polyvinyl formal resins, polyvinyl acetal resins, polyarylate resins, polycarbonate resins, polyester resins, phenoxy resins, acrylic resins, methacrylic resins, polyamide resins, polyurethane resins, Insulating resins such as epoxy resins, silicone resins, polyvinyl alcohol resins, styrene-alkyd resins, silicone-alkyd resins, and phenol-formaldehyde resins can be selected and used, but are limited to these polymers. is not.
- binder resins may be used alone or in combination of two or more, or may be used in a form cured together with a curing agent.
- polyvinyl butyral resin, polyvinyl formal resin, polyvinyl acetal resin, and polyamide resin are preferable because they exhibit good dispersibility and coatability.
- the mixing ratio of the particles to the binder resin can be selected arbitrarily, and it is preferable to use the particles in the range of 10% by mass to 500% by mass from the standpoint of dispersion liquid stability and coating properties.
- the thickness of the undercoat layer can be selected arbitrarily, and is preferably 0.1 ⁇ m or more and 20 ⁇ m or less in view of the properties of the electrophotographic photosensitive member and the applicability of the dispersion liquid. Further, the undercoat layer may contain a known antioxidant or the like.
- the present electrophotographic photoreceptor may optionally have other layers in addition to the above-described conductive support, photosensitive layer, protective layer (outermost layer) and undercoat layer.
- An electrophotographic photosensitive member cartridge according to the present invention has the electrophotographic photosensitive member.
- conventionally known ones can be used by known methods.
- an electrophotographic photoreceptor, a charging device for charging the electrophotographic photoreceptor, an exposure device for exposing the charged electrophotographic photoreceptor to form an electrostatic latent image, and on the electrophotographic photoreceptor At least one device selected from the group consisting of a developing device for developing the formed electrostatic latent image is provided.
- An image forming apparatus has the electrophotographic photoreceptor.
- a conventionally known one can be used by a known method.
- an electrophotographic photoreceptor a charging device that charges the electrophotographic photoreceptor, an exposure device that exposes the charged electrophotographic photoreceptor to form an electrostatic latent image, and an electrostatic latent image formed on the electrophotographic photoreceptor.
- a developing device for developing the electrostatic latent image.
- the organic layer was separated and washed twice with 0.1N aqueous sodium hydroxide solution (50 mL), then with 0.05N aqueous hydrochloric acid solution (50 mL), and twice with demineralized water (50 mL). 4-Methoxyphenol (2 mg) was added to the resulting organic layer and the mixture was concentrated under reduced pressure to obtain 23.43 g of a reaction product containing the above compound (1-1) as a yellow oil.
- the reaction product was analyzed by gel permeation chromatography (GPC) and found to have a number average molecular weight (Mn) of 745, a mass average molecular weight (Mw) of 1086 and Mw/Mn of 1.459.
- the polymer of compound (1-1) is the polymer in the first, second, third, fourth and fifth embodiments.
- a laminated photoreceptor was produced by the following procedure.
- Rutile-type titanium oxide having an average primary particle size of 40 nm (“TTO55N” manufactured by Ishihara Sangyo Co., Ltd.) and 3% by mass of methyldimethoxysilane (“TSL8117” manufactured by Toshiba Silicone Co., Ltd.) relative to the titanium oxide are mixed in a Henschel mixer.
- the surface-treated titanium oxide obtained by mixing was dispersed in a methanol solvent by a bead mill to obtain a dispersion slurry of the surface-treated titanium oxide.
- a coating liquid for a pull layer was prepared. This coating solution was dip-coated on a cylinder (conductive support) made of an aluminum alloy having an outer diameter of 30 mm, a length of 254 mm, and a thickness of 0.75 mm so that the film thickness after drying was 1.5 ⁇ m. was air-dried to form an undercoat layer.
- a charge generation layer coating liquid was prepared. This coating liquid was dip-coated on the undercoat layer so that the film thickness after drying was 0.4 ⁇ m, and then air-dried to form a charge generation layer.
- hole transport substance 1 The chemical structure of hole transport substance 1 is shown below.
- This coating liquid was dip-coated on the charge generation layer so that the film thickness after drying was about 30 ⁇ m, and then dried at 125° C. for 24 minutes to form a charge transport layer.
- Binder resin 1 viscosity average molecular weight 45,700 Binder resin 1 has the following chemical structure.
- antioxidant 1 The chemical structure of antioxidant 1 is as follows.
- Example 1 ⁇ Formation of protective layer> 100 parts of the reaction product obtained in Production Example 1, 55 parts of titanium oxide particles ("TTO55N" manufactured by Ishihara Sangyo Co., Ltd.) surface-treated with 7% by mass of 3-methacryloyloxypropyltrimethoxysilane with respect to the particles, light As a polymerization initiator, 1 part of benzophenone, 2 parts of diphenyl (2,4,6-trimethylbenzoyl)phosphine oxide, a mixed solvent of methanol, 1-propanol and toluene (methanol 70% by mass, 1-propanol 10% by mass % and toluene 20% by mass) to prepare a protective layer coating solution.
- TTO55N titanium oxide particles
- diphenyl (2,4,6-trimethylbenzoyl)phosphine oxide a mixed solvent of methanol, 1-propanol and toluene (methanol 70% by mass, 1-propanol 10% by mass % and tolu
- This coating liquid was dip-coated on the charge transport layer of the laminated photoreceptor prepared as described above so that the film thickness after curing would be about 1 ⁇ m. From the surface side of this coating film, using a UV light irradiation device equipped with a UV-LED lamp having a peak wavelength of 385 nm, UV light was irradiated so that the integrated light amount was 30 J / cm 2 . The reactants obtained were polymerized. Further, after heating at 125° C. for 5 minutes, it was allowed to cool to 25° C. to form a protective layer, thereby obtaining a laminated photoreceptor (sample) having a protective layer as the outermost layer.
- Example 2 to 7, Comparative Examples 1 to 6 A laminate having a protective layer was prepared in the same manner as in Example 1, except that the compound used as shown in Table 1 and the mass part of the titanium oxide particles were changed in place of 100 parts of the reactant obtained in Production Example 1. A type photoreceptor (sample) was obtained.
- a single-layer photoreceptor was produced by the following procedure.
- a coating liquid for an undercoat layer was prepared.
- This coating solution was dip-coated onto a cylinder (conductive support) made of an aluminum alloy having an outer diameter of 30 mm, a length of 244 mm, and a thickness of 0.75 mm so that the film thickness after drying was 0.4 ⁇ m. was air-dried to form an undercoat layer.
- KF-96 was mixed with 792 parts of a mixed solvent (THF 80% by mass, TL 20% by mass) to prepare a single-layer photosensitive layer coating solution.
- This coating solution was dip-coated on the undercoat layer so that the film thickness after drying was about 30 ⁇ m, and dried at 100° C. for 24 minutes to form a single-layer type photosensitive layer.
- the chemical structure of the hole transport substance 2 is shown below.
- the chemical structure of perylene pigment 1 is as follows.
- Binder resin 2 viscosity average molecular weight 49,400 Binder resin 2 has the following chemical structure.
- Examples 8 to 10, Comparative Example 7 The single-layer photoreceptor was used instead of the multi-layer photoreceptor, and the compound used as shown in Table 1 and the mass parts of the titanium oxide particles were changed in place of 100 parts of the reactant obtained in Production Example 1.
- a single-layer photoreceptor (sample) having a protective layer was obtained in the same manner as in Example 1 except for the above.
- a multilayer photoreceptor (sample) having no protective layer was obtained in the same manner as in Example 1, except that no protective layer was formed.
- a single-layer type photoreceptor (sample) having no protective layer was obtained in the same manner as in Example 9, except that no protective layer was formed.
- the laminated photosensitive layer had a Martens hardness of 195 N/mm 2 and an elastic deformation rate of 43%
- the single layer type photosensitive layer had a Martens hardness of 234 N/mm 2 and an elastic deformation rate of 41%. there were.
- the Martens hardness of the photoreceptor surface is 240 N/mm 2 or more, it is “passed ( ⁇ )”, when it is less than 240 N/mm 2 , it is “failed (x)”, and the elastic deformation rate of the photoreceptor surface.
- the elastic deformation rate of the photoreceptor surface was 40% or more, it was evaluated as “acceptable (o)", and when the elastic deformation rate of the photoreceptor surface was less than 40%, it was evaluated as "failed (x)”.
- a multilayer photoreceptor (sample) having no protective layer was obtained in the same manner as in Example 1, except that no protective layer was formed.
- a single-layer type photoreceptor (sample) having no protective layer was obtained in the same manner as in Example 9, except that no protective layer was formed.
- the surface of the laminated photoreceptor (sample) having no protective layer was cut with a cutter, the photosensitive layer was peeled off from the undercoat layer, and a sample for measuring the glass transition temperature of the laminated photosensitive layer was obtained.
- the surface of the single-layer photoreceptor (sample) without the protective layer was cut with a cutter, the photosensitive layer was peeled off from the undercoat layer, and a sample for measuring the glass transition temperature of the single-layer photoreceptor was collected. did.
- Differential scanning calorimetry was performed using the samples for glass transition temperature measurement of the laminated photosensitive layer and single-layer photosensitive layer.
- the measurement conditions were set as follows, and the glass transition temperature was determined from the DSC chart obtained by heating once, then quenching, and then heating again.
- the laminated photosensitive layer had a glass transition temperature of 100°C
- the single layered photosensitive layer had a glass transition temperature of 83°C.
- the light from the halogen lamp was converted to monochromatic light of 780 nm through an interference filter, and the surface potential was measured at an arbitrary exposure amount. At this time, the time from exposure to potential measurement was 60 milliseconds, and the surface potential was measured after irradiation of 0.9 ⁇ J/cm 2 .
- the electrical properties were evaluated according to the following criteria according to the absolute value of the obtained surface potential. Table 1 shows the results.
- ⁇ The absolute value of the surface potential is greater than 40 and 50 or less.
- ⁇ The absolute value of the surface potential is greater than 50 and 70 or less.
- x The absolute value of the surface potential is greater than 70.
- One failed D ⁇ in both electrical characteristics and image flow (pass or fail in Martens hardness and elastic deformation rate of photoreceptor surface)
- E At least one of electrical characteristics and image flow is x or x (regardless of acceptance or rejection of Martens hardness and elastic deformation rate of photoreceptor surface)
- each polymer of Comparative Examples 1 to 5 and 7 is obtained by curing the following commercially available products.
- UV6300B Urethane acrylate oligomer (manufactured by Mitsubishi Chemical Corporation)
- ABE300 EO-modified bisphenol A diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.)
- A-DCP Tricyclodecanedimethanol diacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.)
- A-BPEF 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene (manufactured by Shin-Nakamura Chemical Co., Ltd.)
- the water absorption of the reaction products obtained in Production Examples 1 to 7 and the commercially available acrylic monomers used in Comparative Examples was measured as follows. 100 parts of the reaction product obtained in Production Examples 1 to 7 or the commercially available acrylic monomer used in Comparative Example, 1 part of benzophenone as a photopolymerization initiator, 2 diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide The parts were stirred and mixed. The obtained mixture was formed into a film on a glass plate to obtain a coating film having a thickness of 200 ⁇ m.
- a UV light irradiation device equipped with a UV-LED lamp having a peak wavelength of 385 nm
- the surface of this coating film was irradiated with UV light so that the integrated light amount was 30 J/cm 2 to obtain a polymerization reaction product.
- rice field The resulting polymerized reaction product was peeled off from the glass plate and pulverized to obtain a sample for water absorption measurement.
- X (g) is the weight of the water absorption measurement sample in an environment of 25 ° C. and 50% relative humidity
- Y (g) is the weight after standing for two days and nights in an environment of 32 ° C. and 80% relative humidity.
- the value obtained from the following formula was taken as the water absorption rate. Table 2 shows the results.
- the ions or hydroxide ions increase the ionic conductivity and lower the surface resistance of the photoreceptor, which moves the charges in the unexposed areas of the photoreceptor surface, increasing the contrast between the exposed and unexposed areas. It is presumed that the decrease causes the electrostatic latent image formed by the charges to flow (the image becomes blurred).
- a (meth)acrylic monomer structure with low moisture absorption for example, a monomer having a structure in which a substituent having a (meth)acryloyl group is bonded.
- a monomer having a low moisture absorption structure and a high affinity with the components of the photosensitive layer is selected and used, a mixed layer is formed between the two layers, and the photosensitive layer It is presumed that the charge transport from the layer to the protective layer may be hindered, and the electrical properties may be deteriorated.
- the protective layer as the outermost layer is a structure substituted with a hydrocarbon structure X selected from an alkylene structure, an alkenylene structure or an alkynylene structure with low polarity and a structure having 2 to 3 (meth)acryloyl groups
- a hydrocarbon structure X selected from an alkylene structure, an alkenylene structure or an alkynylene structure with low polarity and a structure having 2 to 3 (meth)acryloyl groups
- the structure of the formula (A) is located around the hydrocarbon structure X and sterically protects it, the polymer can be prevented from being mixed with the components contained in the photosensitive layer. , the formation of a mixed layer can be prevented, and the charge can be sufficiently transported from the photosensitive layer to the protective layer, so that the deterioration of the electrical properties can be prevented.
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Abstract
Description
現在実用化されている感光体の層構成と帯電方式の組み合わせとしては、“負帯電積層型感光体”と、“正帯電単層型感光体”とを挙げることができる。
前記保護層が、下記式(a)で表される構造を有する重合体を含有する電子写真感光体。
導電性支持体と反対側の最表層が、前記式(a)で表される構造を有する重合体を含有する電子写真感光体。
前記保護層が、下記式(b)で表される部分構造及び下記式(A)で表される部分構造を有する重合体を含有する電子写真感光体。
電子写真感光体と反対側の最表層が、前記式(b)で表される部分構造及び前記式(A)で表される部分構造を有する重合体を含有する電子写真感光体。
前記保護層が、下記部分構造X及び下記式(B)で表される部分構造を有する重合体を含有する電子写真感光体。
[12] 前記Xが、炭素と水素からなる鎖状構造である、前記[1]~[11]のいずれか1に記載の電子写真感光体。
前記保護層が、脂肪族ジカルボン酸又は脂肪族ジカルボン酸クロライドと、多価アルコールと、アクリル酸、メタクリル酸、アクリル酸クロライド及びメタクリル酸クロライドからなる群から選ばれる少なくとも1種との反応物を重合させてなる重合体を含有する電子写真感光体。
[15] 前記保護層又は前記最表層と接する感光層のガラス転移温度が50℃以上130℃以下である、前記[1]~[14]のいずれか1に記載の電子写真感光体。
[18] 前記保護層又は前記最表層中の前記金属酸化物粒子の含有量は、前記保護層又は前記最表層の前記重合体100質量部に対して300質量部以下である、前記 [17]に記載の電子写真感光体。
[21] 前記[1]~[19]のいずれか1に記載の電子写真感光体を有する画像形成装置。
本発明の実施形態の一例に係る電子写真感光体(「本電子写真感光体」と称する)は、導電性支持体上に、少なくとも感光層と保護層とを順次有する電子写真感光体であって、前記保護層が、特定の構造を有する重合体を含有するものである。
なお、保護層は、本発明の効果がより得られる観点から、最表層、すなわち導電性支持体と反対側に位置する最表層であるのが好ましい。但し、保護層は必ずしも最表層でなくても、本発明の効果を享受することができる。例えば感光体の最表層に、何らかの偏析層が存在する場合など、保護層が最表層でなくても効果を享受できる。そこで本明細書において、「保護層(最表層)」は、保護層は必ずしも最表層でなくてもよいが、好ましくは最表層としての保護層であるという意味を包含する。
本電子写真感光体は、後述する感光層の下側に導電性支持体を備えている。
導電性支持体としては、その上に位置する感光層を支持することができ、導電性を示すものであれば、特に限定されない。
なお、前記導電性支持体と感光層との間には、接着性・ブロッキング性等の改善のために、後述する下引き層を設けてもよい。
本電子写真感光体は、前記導電性支持体上に感光層を備えている。
当該感光層は、電荷発生物質(CGM)、正孔輸送物質(HTM)、電子輸送物質(ETM)及びバインダー樹脂が同一層内に存在する単層型感光層であってもよいし、また、電荷発生層と電荷輸送層とに分離された積層型感光層であってもよい。
なお、前記保護層(最表層)と接する感光層のマルテンス硬さ及び弾性変形率は、保護層(最表層)を有しない、すなわち、感光層が最表面層である感光体について、後述する方法で求めた値を意味する。
前記保護層(最表層)と接する感光層のマルテンス硬さ及び弾性変形率の測定方法は、後述する、感光層を形成するバインダー樹脂のマルテンス硬さ及び弾性変形率の測定方法と同様である。
先ず、積層型感光層の構成について説明する。
前記電荷発生層(CGL)は、通常、電荷発生物質(CGM)とバインダー樹脂を含有する。
前記電荷輸送層(CTL)は、通常、正孔輸送物質(HTM)及びバインダー樹脂を含有する。また、さらに電子輸送物質(ETM)を含有してもよい。
また、電荷輸送層(CTL)において、前記正孔輸送物質(HTM)に対する前記電子輸送物質(ETM)の含有比率(質量比)は、電子輸送性の観点から、前記正孔輸送物質(HTM)に対して前記電子輸送物質(ETM)が0.005以上であるのが好ましく、中でも0.01以上、その中でも0.02以上であることがさらに好ましい。他方、正孔輸送性の観点から、0.2以下であるのが好ましく、中でも0.1以下、その中でも0.05以下であることがさらに好ましい。
前記単層型感光層は、通常、電荷発生物質(CGM)、正孔輸送物質(HTM)、電子輸送物質(ETM)及びバインダー樹脂を含有する。
感光層(単層型及び積層型のいずれも包含する)に用いる電荷発生物質としては、例えば、セレン及びその合金、硫化カドミウム、その他無機系光導電材料;フタロシアニン顔料、アゾ顔料、ペリレン顔料、多環キノン顔料などの有機顔料;などの各種光導電材料を使用することができる。中でも、特に有機顔料が好ましく、更に、フタロシアニン顔料、アゾ顔料がより好ましい。
感光層(単層型及び積層型のいずれも包含する)に用いる電荷輸送物質は、主に正孔輸送能を有する正孔輸送物質(HTM)と、主に電子輸送能を有する電子輸送物質(ETM)に分類される。正孔輸送物質と電子輸送物質の何れか一方のみを用いてもよく、両方を併用してもよい。
前記正孔輸送物質としては、公知の材料であれば特に限定されるものではない。例えばカルバゾール誘導体、インドール誘導体、イミダゾール誘導体、オキサゾール誘導体、ピラゾール誘導体、チアジアゾール誘導体、ベンゾフラン誘導体等の複素環化合物、アニリン誘導体、ヒドラゾン誘導体、アリールアミン誘導体、スチルベン誘導体、ブタジエン誘導体及びエナミン誘導体並びにこれらの化合物の複数種が結合したもの、及びこれらの化合物からなる基を主鎖若しくは側鎖に有する重合体等の電子供与性物質等を挙げることができる。これらの中でも、カルバゾール誘導体、アリールアミン誘導体、スチルベン誘導体、ブタジエン誘導体及びエナミン誘導体並びにこれらの化合物の複数種が結合したものが好ましい。さらにこれらの中でも、電気特性の観点から、アリールアミン誘導体又はエナミン誘導体がより好ましい。
前記電子輸送物質としては、公知の材料であれば特に限定されるものではない。例えば2,4,7-トリニトロフルオレノン等の芳香族ニトロ化合物、テトラシアノキノジメタン等のシアノ化合物、ジフェノキノン等のキノン化合物等の電子吸引性物質や、公知の環状ケトン化合物やペリレン顔料(ペリレン誘導体)等を挙げることができる。これらの中でも、電気特性の観点から、キノン化合物、ペリレン顔料(ペリレン誘導体)が好ましく、キノン化合物がより好ましい。
感光層(単層型及び積層型のいずれも包含する)に用いるバインダー樹脂は、特に限定されない。例えば、アクリル酸エステル樹脂;メタクリル酸エステル樹脂;ポリビニルブチラール樹脂;ポリアリレート樹脂;ポリアミド樹脂;ポリカーボネート樹脂;ポリエステル樹脂;ポリエステルカーボネート樹脂;フェノキシ樹脂;エポキシ樹脂;シリコーン樹脂;及びこれらの部分的架橋硬化物等を挙げることができる。また前記樹脂は珪素試薬等で修飾されていてもよい。これらは1種を単独で用いてもよく、また2種以上を任意の比率及び組み合わせで用いることもできる。前記樹脂の中でも、正孔輸送物質や電子輸送物質との相溶性の観点から、ポリアリレート樹脂、ポリカーボネート樹脂、ポリエステル樹脂が好ましく、電気特性の観点から、ポリアリレート樹脂、ポリカーボネート樹脂がより好ましい。
また、当該保護層(最表層)と接する感光層を形成するバインダー樹脂の弾性変形率は、36%以上が好ましく、38%以上がより好ましく、40%以上がさらに好ましい。他方、クラック抑制の観点から、前記弾性変形率は、55%以下が好ましく、50%以下がより好ましい。
なお、前記マルテンス硬さ及び弾性変形率は、次に述べる方法で求めた値を意味する。
<測定条件>
最大押込み加重:0.2mN
負荷所要時間:10秒
除荷所要時間:10秒
マルテンス硬さ(N/mm2)=試験荷重(N)/試験荷重下でのビッカース圧子の表面積(mm2)
弾性変形率(%)=(We/Wt)×100
上記式中、全仕事量Wt(nJ)は図2中のA-B-D-Aで囲まれる面積を示し、弾性変形仕事量We(nJ)はC-B-D-C で囲まれる面積を示す。弾性変形率が大きいほど、負荷に対する変形が残留しにくく、弾性変形率が100の場合には変形が残らないことを意味する。
感光層(単層型及び積層型のいずれも包含する)は、前記材料以外にも、成膜性、可撓性、塗布性、耐汚染性、耐ガス性、耐光性等を向上させるために周知の酸化防止剤、可塑剤、紫外線吸収剤、電子吸引性化合物、レベリング剤、可視光遮光剤などの添加物を含有してもよい。
感光層には、これらを適宜、1種単独で、または2種以上を任意の比率及び組み合わせで用いることができる。特に、酸化防止剤及び電子吸引性化合物が含有されていることが好ましい。
酸化防止剤は、本電子写真感光体の酸化を防止するために用いられる安定剤の一種である。
酸化防止剤は1種または2種以上を任意の比率及び組み合わせで用いることができる。
また、本電子写真感光体中には電子吸引性化合物を有してもよい。
電子吸引性化合物の例として具体的には、スルホン酸エステル化合物、カルボン酸エステル化合物、有機シアノ化合物、ニトロ化合物、芳香族ハロゲン誘導体等が挙げられ、好ましくは、スルホン酸エステル化合物、有機シアノ化合物であり、特に好ましくはスルホン酸エステル化合物である。前記電子吸引性化合物は1種のみを単独で用いてもよく、また2種以上を任意の比率及び組み合わせで用いてもよい。
前記感光層の形成方法は特に限定されない。例えば、電荷発生物質や電荷輸送物質、バインダー樹脂及びその他の物質を、溶媒(または分散媒)に溶解(または分散)して得た塗布液を、導電性支持体上(後述する下引き層等の中間層を設ける場合は、これらの中間層上)に塗布することにより形成することができる。
感光層の形成に用いられる溶媒または分散媒としては、特に限定されない。例えば、メタノール、エタノール、プロパノール、2-メトキシエタノール等のアルコール類;テトラヒドロフラン、1,4-ジオキサン、ジメトキシエタン等のエーテル類;ベンゼン、トルエン、キシレン、アニソール等の芳香族炭化水素類;ジクロロメタン、クロロホルム、1,2-ジクロロエタン、1,1,2-トリクロロエタン、1,1,1-トリクロロエタン、テトラクロロエタン、1,2-ジクロロプロパン、トリクロロエチレン等の塩素化炭化水素類;などを挙げることができる。これらは1種を単独で用いてもよく、また2種以上を任意の比率及び組み合わせで併用して用いてもよい。
感光層を形成するための塗布液の塗布方法としては、例えば、スプレー塗布法、スパイラル塗布法、リング塗布法、浸漬塗布法等を挙げることができる。
乾燥温度は、残留溶媒抑制の観点から、通常80℃以上、好ましくは90℃以上、より好ましくは100℃以上である。また、気泡の発生防止、電気特性の観点から、通常250℃以下、好ましくは170℃以下、さらに好ましくは140℃以下であり、段階的に温度を変更してもよい。
乾燥方法としては、熱風乾燥機、蒸気乾燥機、赤外線乾燥機および遠赤外線乾燥機等を用いることができる。
次に、本電子写真感光体の保護層(最表層)について説明する。
(1)第一の実施態様
本発明の第一の実施態様においては、前記保護層は、下記式(a)で表される構造を有する重合体を含有する。
本発明の第二の実施態様においては、前記保護層は、下記式(b)で表される部分構造及び下記式(A)で表される部分構造を有する重合体を含有する。
本発明の第三の実施態様においては、前記保護層は、下記部分構造X及び下記式(B)で表される部分構造を有する重合体を含有する。
前述の通り、(メタ)アクリルモノマーの硬化物を含有する(メタ)アクリルモノマー硬化型保護層を、感光体の最表層として備えた従来の感光体は、高湿度環境下で像流れ(画像ボケ)が発生する課題を抱えていた。
従来の(メタ)アクリルモノマー硬化型保護層が高湿度環境下で像流れを発生する理由は、次のように考えられる。当該保護層中のアクリル樹脂部分が吸湿することで、水分子を構成する水素イオンまたは水酸化物イオンによりイオン伝導性が高まって感光体の表面抵抗が低下する。これにより、感光体表面の未露光部に帯電している電荷が動き、露光部と未露光部のコントラストが低下することで、電荷が形成する静電潜像が流れてしまう(画像がボケる)と推察される。
一方、本電子写真感光体の保護層(最表層)が含有する前記重合体は、前記構造X(以下、炭化水素構造Xとも称する)、すなわち、極性の低いアルキレン構造、アルケニレン構造またはアルキニレン構造を有する骨格を有することから、高湿度環境下においても水分の吸着量が少ないため、吸湿による感光体の表面抵抗の低下を抑制することができる。そのため、感光体表面の未露光部に帯電している電荷が動くのを抑制することができ、露光部と未露光部のコントラストが低下せず、静電潜像が流れるのを防ぐことができると考えられる。
本電子写真感光体の保護層(最表層)が含有する前記重合体は、(メタ)アクリロイル基を2ないし3個有する構造が重合してなる部分構造(前記式(A)又は式(B))を有しており、この式(A)又は式(B)の構造が、前記の低極性な骨格の周囲に位置して立体的に保護することができる。これにより、当該重合体が感光層の含有成分と混合するのを抑制することができ、混合層の形成を防ぎ、感光層から保護層(最表層)への電荷輸送を十分に行うことができると考えられる。
上記第一~第三の実施態様に示した本電子写真感光体の保護層(最表層)の好ましい例として、脂肪族ジカルボン酸又は脂肪族ジカルボン酸クロライドと、多価アルコールと、アクリル酸、メタクリル酸、アクリル酸クロライド及びメタクリル酸クロライドからなる群から選ばれる少なくとも1種との反応物を重合させてなる重合体を有する層を挙げることができる。より具体的には、脂肪族ジカルボン酸と、多価アルコールと、アクリル酸又はメタクリル酸とを脱水縮合により反応させて得られた反応物を、ラジカル重合させてなる重合体を有する層を挙げることができる。また、ラジカル重合させる反応物は、予め多価アルコールとアクリル酸又はメタクリル酸又はアクリル酸クロライド又はメタクリル酸クロライドとを縮合させたアルコール体と、脂肪族ジカルボン酸又は脂肪族ジカルボン酸クロライドとを縮合して得られた反応物でもよい。
脂肪族ジカルボン酸として、具体的には、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ウンデカン二酸、ドデカン二酸、トリデカン二酸、テトラデカン二酸、ペンタデカン二酸、ヘキサデカン二酸、ヘプタデカン二酸、オクタデカン二酸、ノナデカン二酸、イコサン二酸、ヘンイコサン二酸、ドコサン二酸、3-メチル-1,6-ブタンジカルボン酸、4-メチル-1,7-ペンタンジカルボン酸、ジヒドロムコン酸、2,4-ヘキサジエン-1,6-ジカルボン酸、アセチレンジカルボン酸、1,4-シクロヘキサンジカルボン酸、1,3-シクロヘキサンジカルボン酸、1,2-シクロヘキサンジカルボン酸、デカヒドロ-1,4-ナフタレンジカルボン酸、シス-4-シクロヘキセン-1,2-ジカルボン酸等を挙げることができる。その中でも、電気特性と像流れの観点から、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ウンデカン二酸、ドデカン二酸、テトラデカン二酸、1,4-シクロヘキサンジカルボン酸が好ましく、電気特性の観点から、アジピン酸、スベリン酸、アゼライン酸、セバシン酸がより好ましい。
脂肪族ジカルボン酸クロライドについても、前記脂肪族ジカルボン酸と同様の構造でジカルボン酸クロライドとなっているものが好ましい。
多価アルコールとして、具体的には、ペンタエリスリトール、ジペンタエリスリトール、トリメチロールエタン、トリメチロールプロパン等を挙げることができる。その中でも、保護層(最表層)と感光層との混合を抑制する観点から、ペンタエリスリトール又はジペンタエリスリトールが好ましく、像流れ抑制の観点から、ペンタエリスリトールがより好ましい。
上記第一~第三の実施態様に示した本電子写真感光体の保護層(最表層)の主成分重合体である前記重合体のより好ましい一例として、下記式(1)で表される構造を有する重合体を挙げることができる。
前記構造Xは、炭素数4以上20以下の炭化水素構造を表し、前記炭化水素構造は、アルキレン構造、アルケニレン構造またはアルキニレン構造であればよい。この中でも、疎水性の観点から、アルキレン構造が好ましい。
当該炭化水素構造Xは、鎖状構造のものであっても環状構造のものであってもよい。炭化水素構造Xが鎖状構造である場合、直鎖状でも側鎖を含む分岐鎖状のものであってもよい。また、疎水性の観点から、炭素と水素からなることが好ましい。炭化水素構造Xが環状構造である場合、シクロ環を有するものであることが好ましい。これらの中でも、鎖状構造のものが好ましく、炭素と水素からなる直鎖状構造のものがより好ましい。
炭化水素構造Xの炭素数は、4以上20以下であればよく、下限としては、5以上が好ましく、6以上がより好ましく、7以上がさらに好ましい。一方、上限としては、16以下が好ましく、12以下がより好ましく、10以下がさらに好ましい。
前記式(a)中の構造Xの好ましい態様は、前述の通りである。
L1、L2はそれぞれ独立して、-O-、-CO-,-O(C=O)-,-(C=O)-O-,-O(C=O)O-を表す。その中でも、合成の容易さの観点から、-O(C=O)-,-(C=O)-O-が好ましい。
A1、A2は、それぞれ独立して、前記式(A)を表す。式(A)の好ましい態様は、後述の通りである。なお、A1、A2は、それぞれ独立して、前記式(A)を表すことから、当然、A1、A2におけるR11~R13、R21~R23同士はそれぞれ互いに同一でも異なっていてもよい。以下、複数の基を“それぞれ独立して”と定義する場合は、同様に該複数の基が有する置換基は、それぞれ互いに同一でも異なっていてもよい。
前記式(b)中の構造Xの好ましい態様は、前述の通りである。
前記式(A)、式(B)及び式(1)中、R11、R12、R13の炭化水素基として、脂肪族炭化水素基及び芳香族炭化水素基を挙げることができる。
当該脂肪族炭化水素基としては、アルキル基、アルケニル基及びアルキニル基を挙げることができる。脂肪族炭化水素基の炭素数に特に制限はないが、アルキル基は通常1以上、アルケニル基及びアルキニル基は通常2以上である。
一方、アルキル基、アルケニル基及びアルキニル基ともに、好ましくは20以下、より好ましくは10以下、特に好ましくは6以下である。前記炭素数の範囲とすることで、高い溶媒親和性が得られる。
また、前記式(B)及び(1)中、R11、R12およびR13のうち、少なくとも2つは、式(2)で表される基または式(3)で表される基であり、反応後の膜強度の観点から、R11、R12、R13のいずれもが、式(2)で表される基、または、式(3)で表される基であるのが好ましい。
式(2)及び(3)の詳細については、後述する。
R16、R17は単結合、酸素原子であり、電気特性の観点から、R16が酸素原子、R17が単結合であることが好ましい。
前記式(1)中、n12は、溶解性および反応後の膜強度の観点から、2である。
前記式(2)中、R22、R23はそれぞれ独立して、水素原子、炭化水素基またはアルコキシ基を表し、具体的には、前記R11~R13において説明したものと同様の基を挙げることができる。
R34、R35、R36、R37は、それぞれ独立して、水素原子、炭化水素基またはアルコキシ基を表す。具体的には、前記R11~R13において説明したものと同様の基を挙げることができる。
本発明の第一、第二又は第三の実施態様における前記重合体の原料に特に制限はない。
当該重合体において、前記式(b)で表される部分構造及び前記式(A´)で表される部分構造は、分子内にランダムに存在していればよく、中でも、前記式(b)で表される部分構造は、重合体の骨格、すなわち置換基ではなく主鎖の構造であるのが好ましい。
当該重合体において、炭化水素構造X及び前記式(B´)で表される部分構造は、分子内にランダムに存在していればよく、中でも、前記炭化水素構造Xは、重合体の骨格、すなわち置換基ではなく主鎖の構造であるのが好ましい。
A1-L1-X-L2-A2 (a´)
なお、前記吸水率は、後述する実施例に記載の方法で測定することができる。
保護層(最表層)が含有する重合体は、上述した原料に、熱、光、放射線などのエネルギーを与えることで反応が開始するラジカル重合などの方法で重合すればよい。但し、前記重合体を得ることができれば、特に制限はない。
保護層(最表層)が含有する前述の各重合体はそれぞれ、保護層(最表層)の機械的強度と電荷輸送性を向上させる観点から、「電荷輸送能を有する部分構造」をさらに有することが好ましい。
前記連鎖重合性官能基を有する電荷輸送物質の電荷輸送物質部分の構造、すなわち重合体の電荷輸送能を有する部分構造としては、カルバゾール誘導体、インドール誘導体、イミダゾール誘導体、オキサゾール誘導体、ピラゾール誘導体、チアジアゾール誘導体、ベンゾフラン誘導体等の複素環化合物、アニリン誘導体、ヒドラゾン誘導体、アリールアミン誘導体、スチルベン誘導体、ブタジエン誘導体及びエナミン誘導体並びにこれらの化合物の複数種が結合したもの、及びこれらの化合物からなる基を主鎖若しくは側鎖に有する重合体等の電子供与性物質由来の構造を挙げることができる。これらの中でも、電気特性の観点から、カルバゾール誘導体、アリールアミン誘導体、スチルベン誘導体、ブタジエン誘導体及びエナミン誘導体並びにこれらの化合物の複数種が結合したものに由来する構造が好ましく、アリールアミン誘導体に由来する構造がより好ましい。
前記アリールアミン誘導体に由来する構造としては、トリアリールアミン構造が好ましい。
アルキル基の具体例としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、tert-ブチル基、イソブチル基、シクロヘキシル基等を挙げることができる。アルコキシ基の具体例としては、メトキシ基、エトキシ基、プロポキシ基、シクロヘキソキシ基等を挙げることができる。アリール基としては、フェニル基またはナフチル基等を挙げることができる。ハロゲン化アルキル基としては、クロロアルキル基、フルオロアルキル基等を挙げることができる。ハロゲン原子としては、フッ素原子、塩素原子、臭素原子等を挙げることができる。より好ましくはメチル基、エチル基、フェニル基である。
ただし、n41が1の場合、R41は式(5)で表される基であり、n41が2以上の整数の場合、2以上存在するR41はそれぞれ同一であっても異なってもよいが少なくとも1つは式(5)で表される基である。
n42が2以上の整数の場合、2以上存在するR42はそれぞれ同一であっても異なってもよく、n43が2以上の整数の場合、2以上存在する 43はそれぞれ同一であっても異なってもよい。
硬化膜の強度の観点から、n41~n43が1であり、R41が式(5)で表される基であり、かつR42とR43のどちらか一方が式(5)で表される基である場合、または、n41~n43が1であり、R41~R43が式(5)で表される基である場合が好ましい。
溶解性の観点から、n41~n43が1であり、R41が式(5)で表される基、かつR42とR43のどちらか一方が式(5)で表される基である場合がより好ましい。
n51は0以上10以下の整数であり、通常0以上、通常10以下、好ましくは6以下、より好ましくは4以下であり、更に好ましくは3以下である。
R41~R43は、それぞれ独立に、水素原子、アルキル基、アルコキシ基、アリール基、ハロゲン化アルキル基、ハロゲン原子、ベンジル基または下記式(5´)で表される基である。
n41~n43はそれぞれ独立して1以上の整数である。ただし、n41が1の場合、R41は式(5´)で表される基であり、n41が2以上の整数の場合、2以上存在するR41はそれぞれ同一であっても異なってもよいが、少なくとも1つは式(5´)で表される基である。n42が2以上の整数の場合、2以上存在するR42はそれぞれ同一であっても異なってもよく、n43が2以上の整数の場合、2以上存在するR43はそれぞれ同一であっても異なってもよい。
かかる重合体の原料に特に制限はないが、例えば、保護層(最表層)が含有する重合体の原料である前述の各化合物と、連鎖重合性官能基を有する化合物を重合して得ることが好ましい。
トリメチロールプロパントリアクリレート(TMPTA)、トリメチロールプロパントリメタクリレート、HPA変性トリメチロールプロパントリアクリレート、EO変性トリメチロールプロパントリアクリレート、PO変性トリメチロールプロパントリアクリレート、カプロラクトン変性トリメチロールプロパントリアクリレート、HPA変性トリメチロールプロパントリメタクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、グリセロールトリアクリレート、ECH変性グリセロールトリアクリレート、EO変性グリセロールトリアクリレート、PO変性グリセロールトリアクリレート、トリス(アクリロキシエチル)イソシアヌレート、カプロラクトン変性トリス(アクリロキシエチル)イソシアヌレート、EO変性トリス(アクリロキシエチル)イソシアヌレート、PO変性トリス(アクリロキシエチル)イソシアヌレート、ジペンタエリスリトールヘキサアクリレート、カプロラクトン変性ジペンタエリスリトールヘキサアクリレート、ジペンタエリスリトールヒドロキシペンタアクリレート、アルキル変性ジペンタエリスリトールペンタアクリレート、アルキル変性ジペンタエリスリトールテトラアクリレート、アルキル変性ジペンタエリスリトールトリアクリレート、ジメチロールプロパンテトラアクリレート、ペンタエリスリトールエトキシテトラアクリレート、EO変性リン酸トリアクリレート、2,2,5,5,-テトラヒドロキシメチルシクロペンタノンテトラアクリレート、2-ヒドロキシ-3-アクリロイロキシプロピルメタクリレート、ポリエチレングリコールジアクリレート、ポリプロピレングリコールジアクリレート、ポリテトラメチレングリコールジアクリレート、EO変性ビスフェノールAジアクリレート、PO変性ビスフェノールAジアクリレート、9,9-ビス[4-(2-アクリロイルオキシエトキシ)フェニル]フルオレン、トリシクロデカンジメタノールジアクリレート、デカンジオールジアクリレート、ヘキサンジオールジアクリレート、エチレングリコールジメタクリレート、ポリエチレングリコールジメタクリレート、EO変性ビスフェノールAジメタクリレート、PO変性ビスフェノールAジメタクリレート、トリシクロデカンジメタノールジメタクリレート、デカンジオールジメタクリレート、ヘキサンジオールジメタクリレート等を挙げることができる。
ここで、EOとはエチレンオキシドを意味し、POとはプロピレンオキシドを意味し、HPAとは2-ヒドロキシプロピルアクリレートを意味し、ECHとはエピクロロヒドリンを意味する。
ウレタンアクリレートとしては、「EBECRYL(登録商標)8301」、「EBECRYL1290」、「EBECRYL1830」、「KRM8200」(以上、ダイセル・オルネクス株式会社製)、「UV1700B」、「UV7640B」、「UV7605B」、「UV6300B」、「UV7550B」(以上、三菱ケミカル株式会社製)等を挙げることができる。
エステルアクリレートとしては、「M-7100」、「M-7300K」、「M-8030」、「M-8060」、「M-8100」、「M-8530」、「M-8560」、「M-9050」(以上、東亞合成株式会社製)等を挙げることができる。
アクリルアクリレートとしては、「8BR-600」、「8BR-930MB」、「8KX―078」、「8KX-089」、「8KX-168」(以上、大成ファインケミカル株式会社製)等を挙げることができる。
これらは、単独又は2種類以上を併用しても差し支えない。
本電子写真感光体の保護層(最表層)は、前述の各重合体の他に、電荷輸送能を付与する目的で、電荷輸送物質や金属酸化物粒子を含有させてもよい。
また、重合反応を促進するため、重合開始剤を含有させてもよい。
また、電子写真感光体表面の摩擦抵抗や摩耗を軽減する目的で、保護層(最表層)にフッ素樹脂、シリコーン樹脂等を含んでもよく、これらの樹脂からなる粒子や酸化アルミニウム等の無機化合物の粒子を含有させてもよい。
保護層(最表層)に含有させる電荷輸送物質は、前記感光層に用いられる電荷輸送物質と同様のものを用いることができる。
保護層(最表層)には、電荷輸送能を付与する観点及び機械的強度を向上させる観点から、金属酸化物粒子を含有させてもよい。
金属酸化物粒子として、より具体的には、酸化チタン、酸化スズ、酸化アルミニウム、酸化珪素、酸化ジルコニウム、酸化亜鉛、酸化鉄等の1種の金属元素を含む金属酸化物粒子、チタン酸カルシウム、チタン酸ストロンチウム、チタン酸バリウム等の複数の金属元素を含む金属酸化物粒子を挙げることができる。これらの中でもバンドギャップが2~4eVの金属酸化物粒子が好ましい。
金属酸化物粒子は、一種類の粒子のみを用いてもよいし、複数の種類の粒子を混合して用いてもよい。これらの金属酸化物粒子の中でも、酸化チタン、酸化スズ、酸化アルミニウム、酸化珪素、および酸化亜鉛が好ましく、より好ましくは酸化チタンおよび酸化スズである。特には酸化チタンが好ましい。
有機珪素化合物としては、ジメチルポリシロキサン、メチル水素ポリシロキサン等のシリコーンオイル、メチルジメトキシシラン、ジフェニルジジメトキシシラン等のオルガノシラン、ヘキサメチルジシラザン等のシラザン、3-メタクリロイルオキシプロピルトリメトキシシラン、3-アクリロイルオキシプロピルトリメトキシシラン、ビニルトリメトキシシラン、γ-メルカプトプロピルトリメトキシシラン、γ-アミノプロピルトリエトキシシラン等のシランカップリング剤等を挙げることができる。特に、保護層(最表層)の機械的強度を向上させる観点から、連鎖重合性官能基を有する、3-メタクリロイルオキシプロピルトリメトキシシラン、3-アクリロイルオキシプロピルトリメトキシシラン、ビニルトリメトキシシランが好ましい。
なお、これらの表面処理された粒子の最表面はこのような処理剤で処理されているが、該処理のその前に酸化アルミニウム、酸化珪素または酸化ジルコニウム等の処理剤などで処理されていても構わない。
この平均一次粒子径は、透過型電子顕微鏡(Transmission electron microscope 以下、TEMとも称する)により直接観察される粒子の径の算術平均値によって求めることが可能である。
また、酸化アルミニウム粒子の具体的な商品名としては、「Aluminium Oxide C」(日本アエロジル社製)等を挙げることができる。
重合開始剤には、熱重合開始剤、光重合開始剤等が含まれる。
熱重合開始剤としては、2,5-ジメチルヘキサン-2,5-ジヒドロパーオキサイド等の過酸化物系化合物、2,2’-アゾビス(イソブチロニトリル)等のアゾ系化合物を挙げることができる。
また、保護層(最表層)表面の硬化性を補う観点から、アシルフォスフィンオキサイド系化合物と水素引き抜き型開始剤を併用することがさらに好ましい。
アシルフォスフィンオキサイド系化合物に対する水素引き抜き型開始剤の含有割合は、特に限定されるものではない。表面硬化性を補う観点から、アシルフォスフィンオキサイド系化合物1質量部に対し、0.1質量部以上が好ましく、内部硬化性を維持する観点から、5質量部以下が好ましい。
次に、保護層(最表層)の形成方法について説明する。
前記保護層(最表層)の形成方法は、特に限定されない。例えば、バインダー樹脂、電荷輸送物質、金属酸化物粒子、及びその他の物質を溶媒に溶解した塗布液または分散媒に分散した塗布液を塗布することにより形成することができる。
保護層(最表層)形成用塗布液に用いる有機溶媒としては、本発明に係る物質を溶解することができる有機溶媒であれば、どのようなものでも使用することができる。
具体的には、メタノール、エタノール、プロパノール、2-メトキシエタノール等のアルコール類;テトラヒドロフラン、1,4-ジオキサン、ジメトキシエタン等のエーテル類;ギ酸メチル、酢酸エチル等のエステル類;アセトン、メチルエチルケトン、シクロヘキサノン等のケトン類;ベンゼン、トルエン、キシレン、アニソール等の芳香族炭化水素類;ジクロロメタン、クロロホルム、1,2-ジクロロエタン、1,1,2-トリクロロエタン、1,1,1-トリクロロエタン、テトラクロロエタン、1,2-ジクロロプロパン、トリクロロエチレン等の塩素化炭化水素類;n-ブチルアミン、イソプロパノールアミン、ジエチルアミン、トリエタノールアミン、エチレンジアミン、トリエチレンジアミン等の含窒素化合物類;アセトニトリル、N-メチルピロリドン、N,N-ジメチルホルムアミド、ジメチルスルホキシド等の非プロトン性極性溶剤類等を挙げることができる。これらの中から任意の組み合わせ及び任意の割合の混合溶媒を用いることもできる。
また、単独では本発明に係る保護層(最表層)用の物質を溶解しない有機溶媒であっても、例えば、前記の有機溶媒との混合溶媒とすることで溶解可能であれば、使用することができる。
一般に、混合溶媒を用いた方が塗布ムラを少なくすることができる。後述の塗布方法において浸漬塗布法を用いる場合、下層を溶解しない溶媒を選択することが好ましい。この観点から、感光層に好適に用いられるポリカーボネート、ポリアリレートへの溶解性が低い、アルコール類を含有させることが好ましい。
保護層(最表層)を形成するための塗布液の塗布方法は、特に限定されない。例えば、スプレー塗布法、スパイラル塗布法、リング塗布法、浸漬塗布法等を挙げることができる。
保護層(最表層)の厚みは、使用される材料などにより適宜最適な厚みが選択される。寿命の観点より、0.1μm以上が好ましく、0.2μm以上がより好ましく、0.5μm以上が特に好ましい。電気特性の観点より、10μm以下が好ましく、5μm以下がより好ましく、3μm以下が特に好ましい。
該保護層(最表層)は、かかる塗工液を塗布後、外部からエネルギーを与え硬化させて形成するものである。このとき用いられる外部エネルギーとしては熱、光、放射線がある。熱のエネルギーを加える方法としては、空気、窒素などの気体、蒸気、あるいは各種熱媒体、赤外線、電磁波を用い塗工表面側あるいは支持体側から加熱することによって行なわれる。
加熱温度は100℃以上、170℃以下が好ましく、前記下限温度以上では、充分な反応速度となり、完全に反応が進行する。前記上限温度以下では、反応が均一に進行し保護層(最表層)中に大きな歪みが発生するのを抑制できる。硬化反応を均一に進めるために、100℃未満の比較的低温で加熱後、さらに100℃以上に加温し反応を完結させる方法も有効である。
光照射量は、硬化性の観点から0.1J/cm 2以上が好ましく、1J/cm 2以上がさらに好ましく、10J/cm 2以上が特に好ましい。また、電気特性の観点から、200J/cm 2以下が好ましく、100J/cm 2以下がさらに好ましく、50J/cm 2以下が特に好ましい。
本電子写真感光体は、前記感光層と導電性支持体との間に下引き層を有していてもよい。
下引き層に用いる有機顔料の例としては特に限定されない。例えば、前述した電荷発生物質として用いる場合のフタロシアニン顔料やアゾ顔料等を挙げることができる。
また下引き層の膜厚は、任意に選ぶことができ、中でも電子写真感光体の特性、および前記分散液の塗布性から、通常0.1μm以上、20μm以下とすることが好ましい。また下引き層には、公知の酸化防止剤等を含んでいてもよい。
また本電子写真感光体は、上述した導電性支持体、感光層、保護層(最表層)及び下引き層以外に必要に応じて適宜他の層を有していてもよい。
本発明に係る電子写真感光体カートリッジは、前記電子写真感光体を有する。
電子写真感光体カートリッジのその他の構成は、従来公知のものを公知の方法で用いることができる。例えば、電子写真感光体、並びに、前記電子写真感光体を帯電させる帯電装置、帯電した前記電子写真感光体を露光させて静電潜像を形成する露光装置、及び、前記電子写真感光体上に形成された静電潜像を現像する現像装置よりなる群から選ばれる少なくとも1の装置を備える。
本発明に係る画像形成装置は、前記電子写真感光体を有する。
画像形成装置のその他の構成は、従来公知のものを公知の方法で用いることができる。例えば、電子写真感光体、前記電子写真感光体を帯電させる帯電装置、帯電した前記電子写真感光体を露光させて静電潜像を形成する露光装置、及び、前記電子写真感光体上に形成された前記静電潜像を現像する現像装置を備える。
本発明において「X~Y」(X,Yは任意の数字)と表現する場合、特にことわらない限り「X以上Y以下」の意と共に、「好ましくはXより大きい」或いは「好ましくはYより小さい」の意も包含する。
また、「X以上」(Xは任意の数字)或いは「Y以下」(Yは任意の数字)と表現した場合、「Xより大きいことが好ましい」或いは「Y未満であることが好ましい」旨の意図も包含する。
以下の実施例、及び比較例中の「部」の記載は、特に指定しない限り「質量部」を示す。
200mL4つ口反応容器に、アジピン酸(2.15g)とペンタエリスリトール(10.00g)をはかりとり、トルエン(30.00g)、アクリル酸(22.23g)、ハイドロキノン(0.05g)、p-トルエンスルホン酸一水和物(1.58g)、塩化銅(II)(0.05g)を加えた。昇温して還流状態とし、反応の進行と共に生成する水を留去しながら4時間撹拌を続けた後、60℃まで冷却し水50mLを添加した。有機層を分離して、0.1規定水酸化ナトリウム水溶液(50mL)で2回洗浄後、0.05規定塩酸水溶液(50mL)で洗浄し、さらに脱塩水(50mL)で2回洗浄した。得られた有機層に4-メトキシフェノール(2mg)を添加し減圧濃縮することにより、前述の化合物(1-1)を含有する反応物23.43gを黄色オイルとして得た。
当該反応物をゲルパーミエーションクロマトグラフィー(GPC)で分析したところ、数平均分子量(Mn)=745、質量平均分子量(Mw)=1086、Mw/Mn=1.459であった。
ちなみに、化合物(1-1)の重合体は、第一、二、三、四、五の実施形態における重合体となる。
製造例1で使用したアジピン酸の代わりにアゼライン酸(2.76g)を使用した以外は、製造例1と同様にして、前述の化合物(1-2)を含有する反応物23.48gを黄色オイルとして得た。
当該反応物をGPCで分析したところ、Mn=768、Mw=1262、Mw/Mn=1.643であった。
ちなみに、化合物(1-2)の重合体は、第一、二、三、四、五の実施形態における重合体となる。
製造例1で使用したアジピン酸の代わりにセバシン酸(2.97g)を使用した以外は、製造例1と同様にして、前述の化合物(1-3)を含有する反応物26.28gを黄色オイルとして得た。
当該反応物をGPCで分析したところ、Mn=764、Mw=1280、Mw/Mn=1.675であった。
ちなみに、化合物(1-3)の重合体は、第一、二、三、四、五の実施形態における重合体となる。
製造例1で使用したアジピン酸の代わりにテトラデカン二酸(3.80g)を使用した以外は、製造例1と同様にして、前述の化合物(1-4)を含有する反応物26.62gを黄色オイルとして得た。
当該反応物をGPCで分析したところ、Mn=765、Mw=1330、Mw/Mn=1.739であった。
ちなみに、化合物(1-4)の重合体は、第一、二、三、四、五の実施形態における重合体となる。
製造例1で使用したアジピン酸の代わりに1,4-シクロヘキサンジカルボン酸(2.53g)を使用した以外は、製造例1と同様にして、前述の化合物(1-5)を含有する反応物24.08gを黄色オイルとして得た。
当該反応物をGPCで分析したところ、Mn=752、Mw=1080、Mw/Mn=1.436であった。
ちなみに、化合物(1-5)の重合体は、第一、二、三、四、五の実施形態における重合体となる。
製造例1で使用したペンタエリスリトールの代わりにトリメチロールエタン(2.53g)を使用し、アジピン酸(2.92g)、トルエン(36.00g)、アクリル酸(23.03g)ハイドロキノン(0.06g)、p-トルエンスルホン酸一水和物(1.61g)、塩化銅(II)(0.06g)を使用した以外は、製造例1と同様にして、前述の化合物(1-6)を含有する反応物27.29gを黄色オイルとして得た。
当該反応物をGPCで分析したところ、Mn=537、Mw=675、Mw/Mn=1.257であった。
ちなみに、化合物(1-6)の重合体は、第一、二、三、四、五の実施形態における重合体となる。
200mL4つ口反応容器に、イソフタル酸クロライド(東京化成工業株式会社製)(5.00g)とペンタエリスリトールトリアクリレート(トリエステル57%)(商品名:NKエステル A-TMM-3LM-N、新中村化学工業株式会社製)(22.04g)を秤取り、トルエン(90mL)に溶解させた。続いて、トリエチルアミン(7.48g)とトルエン(10mL)との混合溶液を0℃~5℃に冷却した反応容器内へ20分かけて滴下した。反応温度を室温とし5時間攪拌を続けた後、0.1規定塩酸(80mL)を添加し、酸洗浄を行った。次いで有機層を分離し、この有機層を0.1規定塩酸(80mL)にて洗浄を2回行い、さらに、脱塩水(80mL)にて洗浄を2回行った。その後、分離した有機層に4-メトキシフェノール1mgを添加し濃縮することにより、以下の化合物(2)を含有する反応物を得た。
以下の手順により、積層型感光体を作製した。
平均一次粒子径40nmのルチル型酸化チタン(石原産業社製「TTO55N」)と、該酸化チタンに対して3質量%のメチルジメトキシシラン(東芝シリコーン社製「TSL8117」)とを、ヘンシェルミキサーにて混合して得られた表面処理酸化チタンを、メタノール溶媒中でビーズミルにより分散させることにより、表面処理酸化チタンの分散スラリーとした。
該分散スラリーと、メタノール/1-プロパノール/トルエンの混合溶媒と、ε-カプロラクタム/ビス(4-アミノ-3-メチルシクロヘキシル)メタン/ヘキサメチレンジアミン/デカメチレンジカルボン酸/オクタデカメチレンジカルボン酸の組成モル比率が、60%/15%/5%/15%/5%からなる共重合ポリアミドのペレットとを加熱しながら撹拌、混合してポリアミドペレットを溶解させた後、超音波分散処理を行った。
このようにして、メタノール/1-プロパノール/トルエンの質量比が7/1/2で、表面処理酸化チタン/共重合ポリアミドを質量比3/1で含有する、固形分濃度18.0%の下引き層用塗布液を作製した。
この塗布液を、外径30mm、長さ254mm、肉厚0.75mmのアルミニウム合金よりなるシリンダー(導電性支持体)上に、乾燥後の膜厚が1.5μmとなるように浸漬塗布した後、風乾して下引き層を形成した。
電荷発生物質として、CuKα線を用いた粉末X線回折において、回折角2θ±0.2°が27.3°に明瞭なピークを示すD型チタニルフタロシアニン20部と、1,2-ジメトキシエタン280部を混合し、サンドグラインドミルで2時間粉砕して微粒化分散処理を行った。続いて、ポリビニルブチラール(電気化学工業(株)製、商品名「デンカブチラール」#6000C)の2.5% 1,2-ジメトキシエタン溶液400部と、170部の1,2-ジメトキシエタンを混合して電荷発生層用塗布液を作製した。
この塗布液を、前記下引き層上に、乾燥後の膜厚が0.4μmとなるように浸漬塗布した後、風乾して電荷発生層を形成した。
下記構造の正孔輸送物質1を75部、下記構造のバインダー樹脂1を100部、下記構造の酸化防止剤1を4部、レベリング剤としてシリコーンオイル(信越シリコーン社製「KF-96」)0.05部を、テトラヒドロフラン(以下適宜THFと略する)とトルエン(以下適宜TLと略する)の混合溶媒(THF 80質量%、TL 20質量%)616部に混合し、電荷輸送層用塗布液を作製した。
バインダー樹脂1は次の化学構造を有する。
<保護層の形成>
製造例1で得られた反応物を100部、粒子に対し7質量%の3-メタクリロイルオキシプロピルトリメトキシシランで表面処理した酸化チタン粒子(石原産業株式会社製「TTO55N」)を55部、光重合開始剤として、ベンゾフェノンを1部、ジフェニル(2,4,6-トリメチルベンゾイル)フォスフィンオキサイドを2部を、メタノール、1-プロパノール及びトルエンの混合溶媒(メタノール 70質量%、1-プロパノール 10質量%、トルエン 20質量%)720部と混合し、保護層用塗布液を作製した。
この塗布液を、前記のように作製した積層型感光体の電荷輸送層上に、硬化後の膜厚が約1μmになるように浸漬塗布した。この塗膜の表面側から、385nmにピーク波長を有するUV-LEDランプを搭載したUV光照射装置を用いて、積算光量 30J/cm2となるようにUV光を照射し、製造例1で得られた反応物を重合させた。さらに、125℃で5分間加熱した後、25℃まで放冷して保護層を形成し、最表層としての保護層を有する積層型感光体(サンプル)を得た。
製造例1で得られた反応物100部の代わりに、表1のように使用する化合物と、酸化チタン粒子の質量部を変更した以外は、実施例1と同様にして、保護層を有する積層型感光体(サンプル)を得た。
以下の手順により、単層型感光体を作製した。
CuKα線を用いた粉末X線回折において、回折角2θ±0.2°が27.3°に明瞭なピークを示すD型チタニルフタロシアニン20部と、1,2-ジメトキシエタン280部を混合し、サンドグラインドミルで2時間粉砕して微粒化分散処理を行った。続いて、ポリビニルブチラール(電気化学工業(株)製、商品名「デンカブチラール」#6000C)の2.5%1,2-ジメトキシエタン溶液400部と、170部の1,2-ジメトキシエタンを混合して下引き層用塗布液を作製した。
この塗布液を、外径30mm、長さ244mm、肉厚0.75mmのアルミニウム合金よりなるシリンダー(導電性支持体)上に、乾燥後の膜厚が0.4μmとなるように浸漬塗布した後、風乾して下引き層を形成した。
CuKα線を用いた粉末X線回折において、回折角2θ±0.2°が27.3°に明瞭なピークを示すD型チタニルフタロシアニンを2.6部、下記構造のペリレン顔料1を1.3部、下記構造の正孔輸送物質2を100部、前述のET-2で表される電子輸送物質を60部、下記構造のバインダー樹脂2を100部、レベリング剤としてシリコーンオイル(信越シリコーン社製「KF-96」)を0.05部を、混合溶媒(THF 80質量%、TL 20質量%)792部と混合し、単層型感光層用塗布液を作製した。
この塗布液を、前記下引き層上に、乾燥後の膜厚が約30μmになるように浸漬塗布した後、100℃で24分間乾燥させ、単層型感光層を形成した。
バインダー樹脂2は次の化学構造を有する。
積層型感光体の代わりに前記単層型感光体を用い、製造例1で得られた反応物100部の代わりに、表1のように使用する化合物と、酸化チタン粒子の質量部を変更した以外は、実施例1と同様にして、保護層を有する単層型感光体(サンプル)を得た。
保護層の形成を行わないこと以外は実施例1と同様にして、保護層を有しない積層型感光体(サンプル)を得た。また、保護層の形成を行わないこと以外は実施例9と同様にして、保護層を有しない単層型感光体(サンプル)を得た。
次に、前述の方法で、前記保護層を有しない積層型感光体(サンプル)及び前記保護層を有しない単層型感光体(サンプル)を用いて、実施例で使用した積層型感光層及び単層型感光層のマルテンス硬さ及び弾性変形率を測定した。
その結果、前記積層型感光層のマルテンス硬さは195N/mm2、弾性変形率は43%であり、前記単層型感光層のマルテンス硬さは234N/mm2、弾性変形率は41%であった。
前述の通り作製した保護層(最表層)を有する積層型感光体(サンプル)及び単層型感光体(サンプル)について、前記感光層のマルテンス硬さ・弾性変形率測定と同様の方法で、感光体表面のマルテンス硬さ及び弾性変形率を測定した。測定結果を表1に示す。
本発明では、感光体表面のマルテンス硬さが240N/mm2以上の場合を「合格(〇)」、240N/mm2未満の場合を「不合格(×)」、感光体表面の弾性変形率が40%以上の場合を「合格(〇)」、感光体表面の弾性変形率が40%未満の場合を「不合格(×)」、と評価した。
保護層の形成を行わないこと以外は実施例1と同様にして、保護層を有しない積層型感光体(サンプル)を得た。また、保護層の形成を行わないこと以外は実施例9と同様にして、保護層を有しない単層型感光体(サンプル)を得た。
次に、前記保護層を有しない積層型感光体(サンプル)の表面にカッターで切り込みを入れ、下引き層から感光層を剥がして、積層型感光層のガラス転移温度測定用サンプルを採取した。同様に、前記保護層を有しない単層型感光体(サンプル)の表面にカッターで切り込みを入れ、下引き層から感光層を剥がして、単層型感光層のガラス転移温度測定用サンプルを採取した。
<測定条件>
測定装置:株式会社島津製作所製 DSC-60
温度範囲:30~150℃
昇温速度:10℃/min
雰囲気:N2フロー(50mL/min)
測定の結果、前記積層型感光層のガラス転移温度は100℃であり、前記単層型感光層のガラス転移温度は83℃であった。
前記の実施例及び比較例で得られた感光体(サンプル)を、電子写真学会測定標準に従って作製された電子写真特性評価装置(続電子写真技術の基礎と応用、電子写真学会編、コロナ社、404~405頁記載)に装着し、帯電、露光、電位測定、除電のサイクルによる電気特性の評価を行った。温度25℃、相対湿度50%の環境下で、感光体の初期表面電位V0が、積層型感光体の場合は-700Vとなるように、単層型感光体の場合は+700Vとなるように帯電させ、ハロゲンランプの光を干渉フィルターで780nmの単色光としたものを照射して、任意の露光量で表面電位を測定した。この時、露光から電位測定までの時間を60ミリ秒とし、0.9μJ/cm2照射した後の表面電位を測定した。得られた表面電位の絶対値に応じて、電気特性を以下の基準で評価した。結果を表1に示す。
◎:表面電位の絶対値が40以下である。
○:表面電位の絶対値が40より大きく50以下である。
△:表面電位の絶対値が50より大きく70以下である。
×:表面電位の絶対値が70より大きい。
前記の実施例及び比較例で得られた積層型感光体(サンプル)を、電子写真方式のプリンター(ML-6510ND、Samsung社製)に装着し、温度32℃、相対湿度80%の環境下で印刷して、常温常湿下で画像を観察した。全く像流れ(画像ボケ)が見られない場合を「〇」と評価し、わずかに像流れ(画像ボケ)が見られる場合を「△」と評価し、はっきり像流れ(画像ボケ)が見られる場合を「×」と評価し、著しく像流れ(画像ボケ)が見られる場合を「××」とし、○/△/×/××の4段階で像流れの程度を評価した。
次に、前記の実施例及び比較例で得られた単層型感光体(サンプル)を、電子写真方式のプリンターに装着し、前記の積層型感光体(サンプル)の場合と同様の方法で、像流れの程度を評価した。結果を表1に示す。
前記の実施例及び比較例で得られた積層型感光体(サンプル)および単層型感光体(サンプル)の断面を、走査型電子顕微鏡(ZEISS社製、装置名ultra55)を用いて加速電圧3kVの条件で観察した。
得られた画像の中で、保護層と、電荷輸送層または単層型感光層の界面に、両者が混合した層(混合層)が見られるかどうかを観察した。結果を表1に示す。
混合層が見られないものを「〇(very good)」、わずかに混合層が見られるものを「△(good)」、はっきりと混合層が見られる場合を「×(poor)」とした。
観察した画像の例として、比較例4で得られた積層型感光体の断面の走査型電子顕微鏡画像(SEM画像)を図1に示す。図1の上部が保護層側である。
前記電気特性、像流れ、感光体表面のマルテンス硬さ及び弾性変形率の評価を合わせた総合評価を以下の基準で評価した。本発明では、総合評価が「A」又は「B」の場合を、総合的な「合格」と評価した。
A:電気特性と像流れのどちらも○又は◎であり、かつ、感光体表面のマルテンス硬さ及び弾性変形率が合格
B:電気特性と像流れの一方が○又は◎であり、他方が△、かつ、感光体表面のマルテンス硬さ及び弾性変形率が合格
C:電気特性と像流れの一方が○又は◎であり、他方が△、かつ、感光体表面のマルテンス硬さと弾性変形率の少なくとも一方が不合格
D:電気特性と像流れのどちらも△(感光体表面のマルテンス硬さ及び弾性変形率の合否は問わない)
E:電気特性と像流れの少なくとも一方が×又は××(感光体表面のマルテンス硬さ及び弾性変形率の合否は問わない)
UV6300B:ウレタンアクリレートオリゴマー(三菱ケミカル株式会社製)
ABE300:EO変性ビスフェノールAジアクリレート(新中村化学株式会社製)
A-DCP:トリシクロデカンジメタノールジアクリレート(新中村化学株式会社製)
A-BPEF:9,9-ビス[4-(2-アクリロイルオキシエトキシ)フェニル]フルオレン(新中村化学株式会社製)
製造例1~7で得られた反応物、および比較例で使用した市販品のアクリルモノマーについて、次のようにして吸水率を測定した。
製造例1~7で得られた反応物または比較例で使用した市販品のアクリルモノマー100部、光重合開始剤として、ベンゾフェノン1部、ジフェニル(2,4,6-トリメチルベンゾイル)フォスフィンオキサイド2部を攪拌混合した。
得られた混合物をガラス板上に製膜し、厚さが200μmの塗膜を得た。この塗膜の表面に、385nmにピーク波長を有するUV-LEDランプを搭載したUV光照射装置を用いて、積算光量が30J/cm2となるようにUV光を照射し、重合反応物を得た。得られた重合反応物をガラス板から剥がし、粉砕したものを吸水率測定用サンプルとした。
吸水用測定サンプルの温度25℃、相対湿度50%の環境下での重量をX(g)、温度32℃、相対湿度80%の環境下に2昼夜静置した後の重量をY(g)としたとき、下記の式から求めた値を吸水率とした。結果を表2に示す。
前記実施例・比較例、並びに、これまで本発明者が行ってきた試験結果から、次のようなことが分かった。
このような像流れ抑制のための手段として、低吸湿な(メタ)アクリルモノマー構造、例えば(メタ)アクリロイル基を有する置換基を結合させた構造のモノマーを選択して使用することが考えられたが、そのような構造のモノマーの中でも、前記の低吸湿な構造と感光層の含有成分との親和性が高いモノマーを選択して使用すると、両層の間に混合層が形成され、感光層から保護層への電荷輸送が阻害され、電気特性が悪化する場合があると推察される。
これに対し、最表層としての保護層が、極性の低いアルキレン構造、アルケニレン構造またはアルキニレン構造から選ばれる炭化水素構造Xと、(メタ)アクリロイル基を2ないし3個有する構造で置換した構造(「式(A)構造」と称する)とを有していれば、前記炭化水素構造Xの極性が低いため、高湿度環境下においても水分の吸着量が少なくなり、吸湿による抵抗の低下を抑制することができる。そのため、感光体表面の未露光部に帯電している電荷が動くのを抑制することができ、露光部と未露光部のコントラストが低下せず、静電潜像が流れるのを防ぐことができると考えられる。同時に、前記式(A)構造が、前記炭化水素構造Xの周囲に位置して立体的に保護することになるため、当該重合体が感光層の含有成分と混合するのを抑制することができ、混合層の形成を防ぎ、感光層から保護層への電荷輸送を十分に行うことができるため、電気特性の悪化を防ぐことができる。
Claims (21)
- 導電性支持体上に、少なくとも感光層と保護層とを順次有する電子写真感光体であって、
前記保護層が、下記式(a)で表される構造を有する重合体を含有する電子写真感光体。
A1-L1-X-L2-A2 (a)
(式(a)中、Xは炭素数4以上20以下の炭化水素構造を表し、前記炭化水素構造はアルキレン構造、アルケニレン構造またはアルキニレン構造である。L1、L2はそれぞれ独立して、-O-、-CO-,-O(C=O)-,-(C=O)-O-,-O(C=O)O-を表す。A1、A2はそれぞれ独立して下記式(A)を表す。)
(式(A)中、R11~R13はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基または下記式(2)で表される基であり、R11~R13のうち少なくとも2つは、下記式(2)で表される基である。Z1は任意の原子との結合手を示す。)
(式(2)中、R21は水素原子またはメチル基を表す。R22、R23はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n21は1以上10以下の整数を表す。Z2は前記式(A)におけるR11~R13が結合する炭素原子との結合手を示す。Z3は任意の原子との結合手を示す。) - 導電性支持体上に感光層を有する電子写真感光体であって、
導電性支持体と反対側の最表層が、下記式(a)で表される構造を有する重合体を含有する電子写真感光体。
A1-L1-X-L2-A2 (a)
(式(a)中、Xは炭素数4以上20以下の炭化水素構造を表し、前記炭化水素構造は、アルキレン構造、アルケニレン構造またはアルキニレン構造である。L1、L2はそれぞれ独立して、-O-、-CO-,-O(C=O)-,-(C=O)-O-,-O(C=O)O-を表す。A1、A2はそれぞれ独立して下記式(A)を表す。)
(式(A)中、R11~R13はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基または下記式(2)で表される基であり、R11~R13の内少なくとも2つは下記式(2)で表される基である。Z1は任意の原子との結合手を示す。)
(式(2)中、R21は水素原子またはメチル基を表す。R22、R23はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n21は1以上10以下の整数を表す。Z2は前記式(A)におけるR11~R13が結合する炭素原子との結合手を示す。Z3は任意の原子との結合手を示す。) - 前記重合体は、下記式(a´)で表される化合物の重合体である、請求項1又は2に記載の電子写真感光体。
A1-L1-X-L2-A2 (a´)
(式(a´)中、Xは炭素数4以上20以下の炭化水素構造を表し、前記炭化水素構造は、アルキレン構造、アルケニレン構造またはアルキニレン構造である。L1、L2はそれぞれ独立して、-O-、-CO-,-O(C=O)-,-(C=O)-O-,-O(C=O)O-を表す。A1、A2はそれぞれ独立して下記式(A´)を表す。)
(式(A´)中、R11~R13はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基または下記式(2´)で表される基であり、R11~R13のうち少なくとも2つは下記式(2´)で表される基である。Z1は任意の原子との結合手を示す。)
(式(2´)中、R21は水素原子またはメチル基を表す。R22、R23はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n21は1以上10以下の整数を表す。Z2は前記式(A´)におけるR11~R13が結合する炭素原子との結合手を示す。) - 導電性支持体上に、少なくとも感光層と保護層とを順次有する電子写真感光体であって、
前記保護層が、下記式(b)で表される部分構造及び下記式(A)で表される部分構造を有する重合体を含有する電子写真感光体。
-CO-X-CO- (b)
(式(b)中、Xは炭素数4以上20以下の炭化水素構造を表し、前記炭化水素構造は、アルキレン構造、アルケニレン構造またはアルキニレン構造である。)
(式(A)中、R11~R13はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基または下記式(2)で表される基であり、R11~R13の内少なくとも2つは下記式(2)で表される基である。Z1は任意の原子との結合手を示す。)
(式(2)中、R21は水素原子またはメチル基を表す。R22、R23はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n21は1以上10以下の整数を表す。Z2は前記式(A)におけるR11~R13が結合する炭素原子との結合手を示す。Z3は任意の原子との結合手を示す。) - 導電性支持体上に感光層を有する電子写真感光体であって、
電子写真感光体と反対側の最表層が、下記式(b)で表される部分構造及び下記式(A)で表される部分構造を有する重合体を含有する電子写真感光体。
-CO-X-CO- (b)
(式(b)中、Xは炭素数4以上20以下の炭化水素構造を表し、前記炭化水素構造は、アルキレン構造、アルケニレン構造またはアルキニレン構造である。)
(式(A)中、R11~R13はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基または下記式(2)で表される基であり、R11~R13のうち少なくとも2つは下記式(2)で表される基である。Z1は任意の原子との結合手を示す。)
(式(2)中、R21は水素原子またはメチル基を表す。R22、R23はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n21は1以上10以下の整数を表す。Z2は前記式(A)におけるR11~R13が結合する炭素原子との結合手を示す。Z3は任意の原子との結合手を示す。) - 前記重合体は、前記式(b)で表される部分構造及び下記式(A´)で表される部分構造を同一分子内に有する化合物の重合体である、請求項4又は5に記載の電子写真感光体。
(式(A´)中、R11~R13はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基または下記式(2´)で表される基であり、R11~R13のうち少なくとも2つは下記式(2´)で表される基である。Z1は任意の原子との結合手を示す。)
(式(2´)中、R21は水素原子またはメチル基を表す。R22、R23はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n21は1以上10以下の整数を表す。Z2は前記式(A´)におけるR11~R13が結合する炭素原子との結合手を示す。) - 導電性支持体上に、少なくとも感光層と保護層とを順次有する電子写真感光体であって、
前記保護層が、下記部分構造X及び下記式(B)で表される部分構造を有する重合体を含有する電子写真感光体。
X:炭素数4以上20以下の炭化水素構造を表し、前記炭化水素構造は、アルキレン構造、アルケニレン構造またはアルキニレン構造である。
(式(B)中、R11~R13はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基、下記式(2)で表される基または下記式(3)で表される基を表し、R11~R13のうち少なくとも2つは下記式(2)で表される基または下記式(3)で表される基である。R14、R15はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。R16は単結合または酸素原子である。R17は単結合である。n11は1以上10以下の整数を表す。Z4は任意の原子との結合手を示す。)
(式(2)中、R21は水素原子またはメチル基を表す。R22、R23はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n21は1以上10以下の整数を表す。Z2は前記式(B)におけるR11~R13が結合する炭素原子との結合手を示す。Z3は任意の原子との結合手を示す。)
(式(3)中、R31~R33はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基または前記式(2)で表される基を表し、R31~R33のうち少なくとも2つは前記式(2)で表される基を表す。R34~R37はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n31、n32はそれぞれ独立に、1以上10以下の整数を表す。Z2は前記式(B)におけるR11~R13が結合する炭素原子との結合手を示す。) - 前記重合体は、下記式(1)で表される構造を有する重合体である、請求項1~7のいずれか1項に記載の電子写真感光体。
(式(1)中、Xは炭素数4以上20以下の炭化水素構造であり、前記炭化水素構造は、アルキレン構造、アルケニレン構造またはアルキニレン構造である。R11~R13はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基、下記式(2)で表される基または下記式(3)で表される基である。R11~R13のうち少なくとも2つは下記式(2)で表される基または下記式(3)で表される基である。R14、R15はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。R16は単結合または酸素原子である。R17は単結合である。n12は2であり、n11は1以上10以下の整数を表す。)
(式(2)中、R21は水素原子またはメチル基を表し、R22、R23はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表し、n21は1以上10以下の整数を表す。Z2は前記式(1)におけるR11~R13が結合する炭素原子との結合手を示す。Z3は任意の原子との結合手を示す。)
(式(3)中、R31~R33はそれぞれ独立に、水素原子、炭化水素基、アルコキシ基、メチロール基または前記式(2)で表される基を表し、R31~R33のうち少なくとも2つは前記式(2)で表される基を表す。R34~R37はそれぞれ独立に、水素原子、炭化水素基またはアルコキシ基を表す。n31、n32はそれぞれ独立に、1以上10以下の整数を表す。Z2は前記式(1)におけるR11~R 13が結合する炭素原子との結合手を示す。) - 前記Xの炭素数が10以下である、請求項1~10のいずれか1項に記載の電子写真感光体。
- 前記Xが、炭素と水素からなる鎖状構造である、請求項1~11のいずれか1項に記載の電子写真感光体。
- 導電性支持体上に、少なくとも感光層と保護層とを順次有する電子写真感光体であって、
前記保護層が、脂肪族ジカルボン酸又は脂肪族ジカルボン酸クロライドと、多価アルコールと、アクリル酸、メタクリル酸、アクリル酸クロライド及びメタクリル酸クロライドからなる群から選ばれる少なくとも1種との反応物を重合させてなる重合体を含有する電子写真感光体。 - 前記保護層又は前記最表層と接する感光層は、電荷輸送物質を含み、当該感光層における電荷輸送物質の濃度が30質量%以上70重量%以下である、請求項1~13のいずれか1項に記載の電子写真感光体。
- 前記保護層又は前記最表層と接する感光層のガラス転移温度が50℃以上130℃以下である、請求項1~14のいずれか1項に記載の電子写真感光体。
- 前記保護層又は前記最表層は、紫外光又は/及び可視光の照射により硬化されてなる層である、請求項1~15のいずれか1項に記載の電子写真感光体。
- 前記保護層又は前記最表層は、金属酸化物粒子を含有する、請求項1~16のいずれか1項に記載の電子写真感光体。
- 前記保護層又は前記最表層中の前記金属酸化物粒子の含有量は、前記保護層又は前記最表層の前記重合体100質量部に対して300質量部以下である、請求項17に記載の電子写真感光体。
- 前記感光層が積層型感光層である、請求項1~18に記載の電子写真感光体。
- 請求項1~19のいずれか1項に記載の電子写真感光体を有する電子写真感光体カートリッジ。
- 請求項1~19のいずれか1項に記載の電子写真感光体を有する画像形成装置。
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JPH04294361A (ja) * | 1991-03-22 | 1992-10-19 | Ricoh Co Ltd | 電子写真感光体 |
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JP2012013750A (ja) * | 2010-06-29 | 2012-01-19 | Konica Minolta Business Technologies Inc | 有機感光体、画像形成装置及びプロセスカートリッジ |
JP2016114894A (ja) * | 2014-12-17 | 2016-06-23 | コニカミノルタ株式会社 | 電子写真感光体およびそれを備えた画像形成装置 |
JP2019007994A (ja) * | 2017-06-20 | 2019-01-17 | キヤノン株式会社 | 電子写真感光体、電子写真感光体の製造方法、プロセスカートリッジおよび電子写真装置 |
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JPH04294361A (ja) * | 1991-03-22 | 1992-10-19 | Ricoh Co Ltd | 電子写真感光体 |
JPH05323625A (ja) * | 1992-05-22 | 1993-12-07 | Fujitsu Ltd | 感光性耐熱性樹脂組成物 |
JPH06102693A (ja) * | 1992-09-21 | 1994-04-15 | Canon Inc | 電子写真感光体 |
JP2004287361A (ja) * | 2003-03-20 | 2004-10-14 | Ricoh Co Ltd | 電子写真感光体、並びにそれを使用する画像形成装置およびプロセスカートリッジ |
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