# US 2014/0154618 A1 · Electrophotographic photosensitive member, method for producing electrophotographic photosensitive member, process cartridge and electrophotographic apparatus > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0154618 A1 - Document ID: US20140154618A1 - Status: Published application - Kind: A1 - Application number: 14/079,390 - Filed: 2013-11-13 - Published: 2014-06-05 - Earliest claimed: 2012-11-30 - Assignees: Canon Kabushiki Kaisha - Applicants: Canon Kabushiki Kaisha - Inventors: Akihiro Maruyama; Harunobu Ogaki; Yuki Yamamoto - Web page: https://patentgrep.com/patent/US20140154618A1 ## CPC - G03G 5/078: {comprising silicon atoms} - G03G 5/0546: {Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides} - G03G 5/056: {Polyesters} - G03G 5/0564: {Polycarbonates} - G03G 5/0578: {Polycondensates comprising silicon atoms in the main chain} - G03G 5/0589: {Macromolecular compounds characterised by specific side-chain substituents or end groups} - G03G 5/14734: {Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides} - G03G 5/14752: {Polyesters} - G03G 5/14756: {Polycarbonates} - G03G 5/14773: {Polycondensates comprising silicon atoms in the main chain} - G03G 5/14786: {Macromolecular compounds characterised by specific side-chain substituents or end groups} - G03G 5/14791: {Macromolecular compounds characterised by their structure, e.g. block polymers, reticulated polymers, or by their chemical properties, e.g. by molecular weight or acidity} - G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY ## Abstract A charge-transporting layer of an electrophotographic photosensitive member contains a charge-transporting substance, a resin A having a specific structural unit and a resin C having a specific structural unit as resins, and a compound D having a specific structural unit, and the charge-transporting layer contains domains containing the resin A1, the resin A2 and the compound D in a matrix containing the charge-transporting substance and the resin C. ## Claims ### Claim 1 An electrophotographic photosensitive member comprising: a support; a charge-generating layer formed on the support; and a charge-transporting layer formed on the charge-generating layer; wherein the charge-transporting layer is a surface layer of the electrophotographic photosensitive member, and the charge-transporting layer has a matrix-domain structure having: a domain which comprises: a compound D having a structural unit represented by the following formula (O-1) and a structural unit represented by the following formula (O-2); and at least one resin selected from the group consisting of: a resin A1 having a structural unit represented by the following formula (A-1) and a structural unit represented by the following formula (B), and a resin A2 having a structural unit represented by the following formula (A-2) and a structural unit represented by the following formula (B); and a matrix which comprises: a resin C having a structural unit represented by the following formula (C); and a charge-transporting substance; wherein a content of the structural unit represented by the formula (A-1) and the structural unit represented by the formula (A-2) is from 10% by mass to 40% by mass based on the total mass of the resin A1 and the resin A2, where, m11 represents 0 or 1, X11 represents an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a bivalent group having two para-phenylene groups bonded with a methylene group, or a bivalent group having two para-phenylene groups bonded with an oxygen atom, Z11 and Z12 each independently represents an alkylene group having 1 to 4 carbon atoms, R11 to R14 each independently represents an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and n11 represents the repetition number of a structure within brackets, and an average of n11 in the resin A1 ranges from 20 to 150, where, m21 represents 0 or 1, X21 represents an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a bivalent group having two para-phenylene groups bonded with a methylene group, or a bivalent group having two para-phenylene groups bonded with an oxygen atom, Z21 to Z23 each independently represents an alkylene group having 1 to 4 carbon atoms, R16 to R27 each independently represents an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and n21, n22 and n23 each independently represents the repetition number of a structure within brackets, an average of n21 in the resin A2 ranges from 1 to 10, an average of n22 in the resin A2 ranges from 1 to 10, and an average of n23 in the resin A2 ranges from 20 to 200, where, m31 represents 0 or 1, X31 represents an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a bivalent group having two para-phenylene groups bonded with a methylene group, or a bivalent group having two para-phenylene groups bonded with an oxygen atom, Y31 represents a single bond, a methylene group, an ethylidene group, a propylidene group, a cyclohexylidene group, a phenylmethylene group, a phenylethylidene group or an oxygen atom, and R31 to R38 each independently represents a hydrogen atom or a methyl group, where, m41 represents 0 or 1, X41 represents an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a bivalent group having two para-phenylene groups bonded with a methylene group, or a bivalent group having two para-phenylene groups bonded with an oxygen atom, Y41 represents a single bond, a methylene group, an ethylidene group, a propylidene group, a cyclohexylidene group, a phenylmethylene group, a phenylethylidene group or an oxygen atom, and R41 to R48 each independently represents a hydrogen atom or a methyl group, where, R64 represents a hydrogen atom or a methyl group, R62 represents a phenyl group, a cyano group, a carbamoyl group, or a group represented by the formula —COOR64, where R64 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a 2-ethylhexyl group, a nonyl group, an isononyl group, a cyclohexyl group, a 2-methoxyethyl group or a 2-hydroxyethyl group, R63 represents a hydrogen atom or a methyl group, and n61 represents the repetition number of a structure within brackets, and an average of n61 in the compound D ranges from 1 to 500. ### Claim 2 (depends on 1) The electrophotographic photosensitive member according to claim 1, wherein a content of the compound D in the charge-transporting layer is from 1% by mass to 50% by mass based on the total mass of the resin A1 and the resin A2. ### Claim 3 (depends on 1) The electrophotographic photosensitive member according to claim 1, wherein R62 represents a phenyl group or a group represented by the formula —COOR64, where R64 represents a hydrogen atom, a methyl group, a 2-ethylhexyl group, a 2-methoxyethyl group or a 2-hydroxyethyl group. ### Claim 4 (depends on 1) The electrophotographic photosensitive member according to claim 1, wherein a content of the compound D is from 0.1% by mass to 20% by mass based on a total mass of all resins contained in the charge-transporting layer. ### Claim 5 (depends on 1) The electrophotographic photosensitive member according to claim 1, wherein the charge-transporting substance is at least one selected from the group consisting of a triarylamine compound, a hydrazone compound, a butadiene compound and an enamine compound. ### Claim 6 (depends on 1) The electrophotographic photosensitive member according to claim 1, wherein a content of the charge-transporting substance is from 25% by mass to 70% by mass based on a total mass of the charge-transporting layer. ### Claim 7 (depends on 1) The electrophotographic photosensitive member according to claim 1, wherein a total content of the resin A1 and the resin A2 is from 5% by mass to 50% by mass based on a total mass of all resins contained in the charge-transporting layer. ### Claim 8 A method for producing an electrophotographic photosensitive member comprising a support, a charge-generating layer formed on the support, and a charge-transporting layer formed on the charge-generating layer, the charge-transporting layer being a surface layer of the electrophotographic photosensitive member, the method comprising: preparing a charge-transporting layer coating solution containing: at least one resin selected from the group consisting of: a resin A1 having a structural unit represented by the following formula (A-1) and a structural unit represented by the following formula (B); and a resin A2 having a structural unit represented by the following formula (A-2) and a structural unit represented by the following formula (B); a compound D having a structural unit represented by the following formula (O-1) and a structural unit represented by the following formula (O-2); a resin C having a structural unit represented by the following formula (C); and a charge-transporting substance; and forming the charge-transporting layer by forming a coating film of the charge-transporting layer coating solution and drying the coating film, wherein a content of the structural unit represented by the formula (A-1) and the structural unit represented by the formula (A-2) is from 10% by mass to 40% by mass based on a total mass of the resin A1 and the resin A2, where, m11 represents 0 or 1, X11 represents an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a bivalent group having two para-phenylene groups bonded with a methylene group, or a bivalent group having two para-phenylene groups bonded with an oxygen atom, Z11 and Z12 each independently represents an alkylene group having 1 to 4 carbon atoms, R11 to R14 each independently represents an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and n11 represents the repetition number of a structure within brackets, and an average of n11 in the resin A1 ranges from 20 to 150, where, m21 represents 0 or 1, X21 represents an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a bivalent group having two para-phenylene groups bonded with a methylene group, or a bivalent group having two para-phenylene groups bonded with an oxygen atom, Z21 to Z23 each independently represents an alkylene group having 1 to 4 carbon atoms, R16 to R27 each independently represents an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and n21, n22 and n23 each independently represents the repetition number of a structure within brackets, an average of n21 in the resin A2 ranges from 1 to 10, an average of n22 in the resin A2 ranges from 1 to 10, and an average of n23 in the resin A2 ranges from 20 to 200, where, m31 represents 0 or 1, X31 represents an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a bivalent group having two para-phenylene groups bonded with a methylene group, or a bivalent group having two para-phenylene groups bonded with an oxygen atom, Y31 represents a single bond, a methylene group, an ethylidene group, a propylidene group, a cyclohexylidene group, a phenylmethylene group, a phenylethylidene group or an oxygen atom, and R31 to R38 each independently represents a hydrogen atom or a methyl group, where, m41 represents 0 or 1, X41 represents an ortho-phenylene group, a meta-phenylene group, a para-phenylene group, a bivalent group having two para-phenylene groups bonded with a methylene group, or a bivalent group having two para-phenylene groups bonded with an oxygen atom, Y41 represents a single bond, a methylene group, an ethylidene group, a propylidene group, a cyclohexylidene group, a phenylmethylene group, a phenylethylidene group or an oxygen atom, and R41 to R48 each independently represents a hydrogen atom or a methyl group, where, R61 represents a hydrogen atom or a methyl group, R62 represents a phenyl group, a cyano group, a carbamoyl group, or a group represented by the formula —COOR64, where R64 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a 2-ethylhexyl group, a nonyl group, an isononyl group, a cyclohexyl group, a 2-methoxyethyl group or a 2-hydroxyethyl group, R63 represents a hydrogen atom or a methyl group, and n61 represents the repetition number of a structure within brackets, and an average of n61 in the compound D ranges from 1 to 500. ### Claim 9 (depends on 1) A process cartridge detachably attachable to a main body of an electrophotographic apparatus, wherein the process cartridge integrally supports: the electrophotographic photosensitive member according to claim 1, and at least one device selected from the group consisting of a charging device, a developing device, a transferring device and a cleaning device. ### Claim 10 (depends on 1) An electrophotographic apparatus comprising: the electrophotographic photosensitive member according to claim 1; and a charging device, an exposing device, a developing device and a transferring device.