# US 9,753,385 B2 · Electrophotographic photosensitive member, method for manufacturing electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

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- Number: US 9,753,385 B2
- Document ID: US9753385B2
- Status: Granted
- Kind: B2
- Application number: 15/054,017
- Filed: 2016-02-25
- Published: 2016-09-01
- Granted: 2017-09-05
- Earliest claimed: 2015-02-27
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Yota Ito; Daisuke Miura; Shoma Hinata; Hiroyuki Tomono; Takashi Anezaki; Tatsuya Yamaai; Kazumichi Sugiyama; Masataka Kawahara; Hirotoshi Uesugi; Akihiro Maruyama; Hirofumi Kumoi; Masato Tanaka
- Web page: https://patentgrep.com/patent/US9753385B2

## CPC

- G03G 5/0564: {Polycarbonates}
- G03G 5/047: characterised by the charge-generation layers or charge transport layers {(G03G5/0433 and G03G5/0436 take precedence)}
- G03G 5/0525: {Coating methods}
- G03G 5/14756: {Polycarbonates}
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY

## Abstract

An electrophotographic photosensitive member has a support, a charge generation layer, and a charge transport layer in this order, the charge transport layer containing a charge transport material. The charge transport layer is a surface layer of the electrophotographic photosensitive member and contains a polycarbonate resin having a structural unit selected from group A and a structural unit selected from group B (groups A and B defined in the disclosure).

## Claims

### Claim 1

An electrophotographic photosensitive member comprising a support, a charge generation layer, and a charge transport layer In this order, the charge transport layer containing a charge transport material,
the charge transport layer being a surface layer of the electrophotographic photosensitive member,
the charge transport layer containing a polycarbonate resin having a structural unit selected from group A and a structural unit selected from group B,
the group A including structural units represented by formulae (101) and (102):
where R211 to R214 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, R215 represents an alkyl, aryl, or alkoxy group, R216 and R217 each independently represent an alkyl group containing 1 to 9 carbon atoms, i211 represents an integer of 0 to 3, and R2 and (CH2)iCHR216R217 are different croons;
where R221 to R224 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, R225 and R226 each independently represent an alkyl group containing 1 to 9 carbon atoms, R225 and R226 are different croons, and i221 represents an integer of 0 to 3;
the group d including structural units represented by formulae (104), (105), and (106):
where R242 to R244 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and X represents a single bond, an oxygen atom, a sulfur atom, or a sulfonyl group;
where R251 to R254 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and R256 and R257 each independently represent a hydrogen atom or an alkyl, aryl, or halogenated alkyl group;
where R261 to R264 independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and W represents a cycloalkylidene group containing 5 to 12 carbon atoms.

### Claim 2 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein the polycarbonate resin has a weight-average molecular weight of 40,000 or more and 80,000 or less.

### Claim 3 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein a proportion of the structural unit selected from the group A in the polycarbonate resin is 20 mol % or more and 70 mol % or less.

### Claim 4 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein in the charge transport layer, a quantity of the charge transport material is 70% by mass or less of a quantity of the polycarbonate resin.

### Claim 5

A method for manufacturing an electrophotographic photosensitive member, the electrophotographic photosensitive member having a support, a charge generation layer, and a charge transport layer in this order, the charge transport layer containing a charge transport material,
the charge transport layer being a surface layer of the electrophotographic photosensitive member,
the charge transport layer containing a polycarbonate resin having a structural unit selected from group A and a structural unit selected from group B,
the group A including structural units represented by formulae (101) and (102):
where R211 to R214 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, R215 represents an alkyl, aryl, or alkoxy group, R216 and R217 each independently represent an alkyl group containing 1 to 9 carbon atoms, i211 represents an integer of 0 to 3, and R215 and (CH2)iCHR216R217 are different groups;
where R221 to R224 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, R225 and R226 each independently represent an alkyl group containing 1 to 9 carbon atoms, R225 and R226 are different groups, and i221 represents an integer of 0 to 3;
the group B including structural units represented by formulae (104) (105), and (106):
where R241 to R244 to each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and X represents a single bond, an oxygen atom, a sulfur atom, or a sulfonyl group;
where R251 to R254 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and R256 and R257 each independently represent a hydrogen atom or an alkyl, aryl, or halogenated alkyl group;
where R261 to R264 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and W represents a cycloalkylidene group containing 5 to 12 carbon atoms,
the method comprising:
producing the charge transport layer by forming a wet coating of a coating liquid configured to form the charge transport layer, the coating liquid containing the charge transport material, the polycarbonate resin, and a solvent having a dipole moment of 1.0 D or less; and
drying the wet coating.

### Claim 6 (depends on 5)

The method according to claim 5 for manufacturing an electrophotographic photosensitive member, wherein the solvent having a dipole moment of 1.0 D or less is one selected from xylene and methylal.

### Claim 7

A process cartridge comprising an electrophotographic photosensitive member and at least one unit selected from the group consisting of a charging unit, a development unit, a transfer unit, and a cleaning unit, the process cartridge integrally holding the electrophotographic photosensitive member and the at least one unit and configured to be detachably attached to a main body of an electrophotographic apparatus,
the electrophotographic photosensitive member having a support, a charge generation layer, and a charge transport layer in this order, the charge transport layer containing a charge transport material,
the charge transport layer being a surface layer of the electrophotographic photosensitive member,
the charge transport layer containing a polycarbonate resin having a structural unit selected from group A and a structural unit selected from group B,
the group A including structural units represented by formulae (101) and (102):
where R211 to R214 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, R215 represents an alkyl, aryl, or alkoxy group, R216 and R217 each independently represent an alkyl group containing 1 to 9 carbon atoms, i211 represents an integer of 0 to 3, and R215 and (CH2)1CHR216R217 are different groups;
where R221 to R224 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, R225 and R226 each independently represent an alkyl group containing 1 to 9 carbon atoms, R225 and R226 are different groups, and i221 represents an integer of 0 to 3;
the group B including structural units represented by formulae (104) (105), and (106):
Where R241 and R244 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and X represents a single bond, an oxygen atom, a sulfur atom, or a sulfonyl group;
where R251 to R254 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and R256 and R257 each independently represent a hydrogen atom or an alkyl, aryl, or halogenated alkyl group;
where B261 to R264 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and W represents a cycloalkylidene group containing 5 to 12 carbon atoms.

### Claim 8

An electrophotographic apparatus comprising an electrophotographic photosensitive member and a charging unit, an exposure unit, a development unit, and a transfer unit,
the electrophotographic photosensitive member having a support, a charge generation layer, and a charge transport layer in this order, the charge transport layer containing a charge transport material,
the charge transport layer being a surface layer of the electrophotographic photosensitive member,
the charge transport layer containing a polycarbonate resin having a structural unit selected from group A and a structural unit selected from group B,
the group A including structural units represented by formulae (101) and (102)
where R211 to R214 each independently represent a represents a single bond, an oxygen atom, a sulfur atom, or a sulfonyl group;
where R251 to R254 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and R256 and R257 each independently represent a hydrogen atom or an alkyl, aryl, or halogenated alkyl group;
where R261 to R264 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and W represents a cycloalkylidene group containing 5 to 12 carbon atoms.
hydrogen atom or an alkyl, aryl, or alkoxy group, R215 represents an alkyl, aryl, or alkoxy group, R216 and R217 each independently represent an alkyl group containing 1 to 9 carbon atoms, i211 represents an integer of 0 to 3, and R215 and (CH2)iCHR216R217 are different groups;
where R221 to R224 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, R225 and R226 each independently represent an alkyl group containing 1 to 9 carbon atoms, R225 and R226 are different groups, and i221 represents an integer of 0 to 3;
the group B including structural units represented by formulae (104), (105), and (106):
where R241 to R244 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and X represents a single bond, an oxygen atom, a sulfur atom, or a sulfonyl group;
where R251 to R254 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and R256 and R257 each independently represent a hydrogen atom or an alkyl, aryl, or halogenated alkyl group;
where R261 to R264 each independently represent a hydrogen atom or an alkyl, aryl, or alkoxy group, and W represents a cycloalkylidene group containing 5 to 12 carbon atoms.