# US 11,029,616 B2 · Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

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- Number: US 11,029,616 B2
- Document ID: US11029616B2
- Status: Granted
- Kind: B2
- Application number: 16/894,977
- Filed: 2020-06-08
- Published: 2020-12-17
- Granted: 2021-06-08
- Earliest claimed: 2019-06-13
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Shubun Kujirai; Koichi Nakata; Haruki Mori
- Web page: https://patentgrep.com/patent/US11029616B2

## CPC

- G03G 5/0732: {comprising pending alkenylarylamine}
- 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 5/0592: {Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity}
- G03G 5/0596: {Macromolecular compounds characterised by their physical properties}
- 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 5/14791: {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 5/14795: {Macromolecular compounds characterised by their physical properties}
- G03G 15/75: {Details relating to xerographic drum, band or plate, e.g. replacing, testing (electrographic recording members per se G03G5/00)}
- G03G 21/1803: {Arrangements or disposition of the complete process cartridge or parts thereof}
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY

## Abstract

An electrophotographic photosensitive member including: a support; and a surface layer, wherein the surface layer contains a cured product of a composition containing a curable hole-transport compound, a specific fluorine-atom-containing compound, and a specific polymerizable compound.

## Claims

### Claim 1

An electrophotographic photosensitive member comprising:
a support; and a surface layer,
wherein the surface layer contains a cured product of a composition containing a curable hole-transport compound, a compound represented by the following formula (1), and a compound represented by the following formula (2),
in the formula (1), Rf11 represents a divalent group having 3 or more carbon atoms and 6 or more fluorine atoms, R12 and R13 each independently represent a hydrogen atom, a fluorine atom, an acryloyloxy group, or a methacryloyloxy group, with the proviso that at least one of R12 and R13 is an acryloyloxy group or a methacryloyloxy group,
in the formula (2), R21 and R22 each independently represent an alkyl group having 1 or more and 4 or less carbon atoms, or a substituted or unsubstituted aryl group having 1 or more and 4 or less carbon atoms, the substituent, which can be a substituent of the aryl group, is an alkyl group having 1 or more and 4 or less carbon atoms, R21 and R22 may be joined together to form a ring, R23 represents an alkyl group having 1 or more and 4 or less carbon atoms, R24 and R25 each independently represent a hydrogen atom or a methyl group, and R26 and R27 each independently represent an alkylene group having 1 or more and 4 or less carbon atoms.

### Claim 2 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein, in the composition, when the mass of the curable hole-transport compound is denoted by A, the mass of the compound represented by the formula (1) is denoted by B, and the mass of the compound represented by the formula (2) is denoted by C, a ratio of A to the sum total of A, B, and C, which is A/(A+B+C), is 0.5 or more and 0.85 or less.

### Claim 3 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein, in the composition, when the mass of the curable hole-transport compound is denoted by A, the mass of the compound represented by the formula (1) is denoted by B, and the mass of the compound represented by the formula (2) is denoted by C, a ratio of B to the sum total of A, B, and C, which is B/(A+B+C), is 0.1 or more and 0.2 or less.

### Claim 4 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein, in the composition, when the mass of the curable hole-transport compound is denoted by A, the mass of the compound represented by the formula (1) is denoted by B, and the mass of the compound represented by the formula (2) is denoted by C, a ratio of C to the sum total of A, B, and C, which is C/(A+B+C), is 0.1 or more and 0.2 or less.

### Claim 5 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein the surface layer is a protection layer, and the film thickness of the protection layer is 2 μm or more and 8 μm or less.

### Claim 6 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein in an infrared spectrum obtained for the surface layer, when the maximum value of peak height within the wavenumber range of from 1100 cm−1 to 1125 cm−1 is denoted by D, and the maximum value of peak height within the wavenumber range of from 1700 cm−1 to 1770 cm−1 is denoted by E, the ratio of D to E, which is D/E, is 0.30 or more and 0.45 or less.

### Claim 7 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (3), or a compound represented by the following formula (4),
(R34R32Rf31R33R35) (3)
in the formula (3), Rf31 represents a group in which 6 or more hydrogen atoms in the alkylene group are each substituted with a fluorine atom, R32 and R33 represent an alkylene group or a phenylene group, R34 and R35 are a hydrogen atom, a fluorine atom, a group represented by the following formula (5), or a group represented by the following formula (6), with the proviso that at least one of R34 and R35 is a group represented by the following formula (5) or a group represented by the following formula (6),
(R44Rf42R41Rf43R45) (4)
in the formula (4), R41 represents an alkylene group or a phenylene group, Rf42 and Rf43 each represent a group in which 3 or more hydrogen atoms in the alkylene group are each substituted with a fluorine atom, R44 and R45 represent a hydrogen atom, a fluorine atom, a group represented by the following formula (5), or a group represented by the following formula (6), with the proviso that at least one of R44 and R45 is a group represented by the following formula (5) or a group represented by the following formula (6),
in the formula (5), the symbol ** represents a position at which the group is bonded to each of R32, R33, R42, and R43, R51 represents a single bond or an alkylene group having 1 or more and 6 or less carbon atoms, and R52 represents a hydrogen atom or a methyl group,
in the formula (6), the symbol ** represents a position at which the group is bonded to each of R32, R33, R42, and R43, R61 represents an alkylene group having 1 or more and 6 or less carbon atoms, R62 represents a hydrogen atom or a methyl group, and subscript s represents an integer of 0 or more and 4 or less.

### Claim 8 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein the curable hole-transport compound is a compound represented by the following formula (7):
in the formula (7), R71 and R72 each independently represent an alkyl group having 2 or more and 8 or less carbon atoms, R73 and R74 each independently represent a hydrogen atom or an alkyl group having 4 or less carbon atoms, R75 and R77 each independently represent an alkylene group having 3 or more and 6 or less carbon atoms, and R76 and R78 each independently represent a hydrogen atom or a methyl group.

### Claim 9 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein at least one of R21 and R22 in the compound represented by the formula (2) is an alkyl group having 2 or more carbon atoms.

### Claim 10

A process cartridge that is detachably attachable to an electrophotographic apparatus main body, and integrally supports:
an electrophotographic photosensitive member; and
at least one unit selected from the group consisting of a charging unit, a developing unit, a transfer unit, and a cleaning unit,
wherein the electrophotographic photosensitive member comprises a support and a surface layer,
the surface layer includes a cured product of a composition containing a curable hole-transport compound, a compound represented by the following formula (1), and a compound represented by the following formula (2),
in the formula (1), Rf11 represents a divalent group having 3 or more carbon atoms and 6 or more fluorine atoms, R12 and R13 each independently represent a hydrogen atom a fluorine atom, an acryloyloxy group, or a methacryloyloxy group, with the proviso that at least one of R12 and R13 is an acryloyloxy group or a methacryloyloxy group,
in the formula (2), R21 and R22 each independently represent an alkyl group having 1 or more and 4 or less carbon atoms or a substituted or unsubstituted aryl group having 1 or more and 4 or less carbon atoms, a substituent, which can be a substituent of the aryl group, is an alkyl group having 1 or more and 4 or less carbon atoms, R21 and R22 may be joined together to form a ring, R23 represents an alkyl group having 1 or more and 4 or less carbon atoms, R24 and R25 each independently represent a hydrogen atom or a methyl group, and R26 and R27 each independently represent an alkylene group having 1 or more and 4 or less carbon atoms.

### Claim 11

An electrophotographic apparatus, comprising: an electrophotographic photosensitive member; and a charging unit, an exposing unit, a developing unit, and a transfer unit,
wherein the electrophotographic photosensitive member comprises a support and a surface layer,
the surface layer includes a cured product of a composition containing a curable hole-transport compound, a compound represented by the following formula (1), and a compound represented by the following formula (2),
in the formula (1), Rf11 represents a divalent group having 3 or more carbon atoms and 6 or more fluorine atoms, R12 and R13 each independently represent a hydrogen atom, a fluorine atom, an acryloyloxy group, or a methacryloyloxy group, with the proviso that at least one of R12 and R13 is an acryloyloxy group or a methacryloyloxy group,
in the formula (2), R21 and R22 each independently represent an alkyl group having 1 or more and 4 or less carbon atoms, or a substituted or unsubstituted aryl group having 1 or more and 4 or less carbon atoms, a substituent, which can be a substituent of the aryl group, is an alkyl group having 1 or more and 4 or less carbon atoms, R21 and R22 may be joined together to form a ring, R23 represents an alkyl group having 1 or more and 4 or less carbon atoms, R24 and R25 each independently represent a hydrogen atom or a methyl group, and R26 and R27 each independently represent an alkylene group having 1 or more and 4 or less carbon atoms.