# US 10,372,048 B2 · Electrophotographic photosensitive member

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- Number: US 10,372,048 B2
- Document ID: US10372048B2
- Status: Granted
- Kind: B2
- Application number: 16/035,859
- Filed: 2018-07-16
- Published: 2019-01-24
- Granted: 2019-08-06
- Earliest claimed: 2017-07-21
- Assignees: KYOCERA Document Solutions Inc.
- Applicants: KYOCERA Document Solutions Inc.
- Inventors: Jun Azuma; Kensuke Kojima; Tomofumi Shimizu
- Web page: https://patentgrep.com/patent/US10372048B2

## CPC

- G03G 5/0618: {containing oxygen and nitrogen}
- 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 5/0607: {containing at least one non-six-membered ring}
- G03G 5/0609: {containing oxygen}
- G03G 5/061446: {terphenyl-diamine}
- G03G 5/0651: {containing four relevant rings}
- G03G 5/0677: {Monoazo dyes}
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY

## Abstract

An electrophotographic photosensitive member includes a conductive substrate and a photosensitive layer. The photosensitive layer includes a charge generating layer and a charge transport layer. The charge generating layer contains a charge generating material. The charge transport layer contains a hole transport material and a binder resin. The charge transport layer further contains an electron acceptor compound. The hole transport material includes a compound represented by general formula (1). In general formula (1), R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 each represent, independently of one another, a hydrogen atom or a methyl group.

## Claims

### Claim 1

An electrophotographic photosensitive member comprising a conductive substrate and a photosensitive layer, wherein
the photosensitive layer includes a charge generating layer and a charge transport layer,
the charge generating layer contains a charge generating material,
the charge transport layer contains a hole transport material and a binder resin,
the charge transport layer further contains an electron acceptor compound, and
the hole transport material includes only a compound represented by a chemical formula (1-2),

### Claim 2 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
a ratio of a mass of the hole transport material to a mass of the binder resin is at least 0.50.

### Claim 3 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
the binder resin includes a polyarylate resin, and
the polyarylate resin includes at least one repeating unit represented by a general formula (10), a repeating unit represented by a chemical formula (11-X1), and at least one repeating unit represented by a general formula (11′)
where in the general formula (10),
R11 and R12 each represent, independently of each other, a hydrogen atom or a methyl group, and
R13 represents a hydrogen atom or an alkyl group having a carbon number of at least 1 and no greater than 4 and R14 represents an alkyl group having a carbon number of at least 1 and no greater than 4, or R13 and R14 bond together to represent a cycloalkylidene group having a carbon number of at least 5 and no greater than 14, and
X′ in the general formula (11′) represents a divalent group represented by a chemical formula (X2), (X3), (X4), (X5) or (X6)

### Claim 4 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
the binder resin includes a polyarylate resin, and
the polyarylate resin is
a polyarylate resin including repeating units represented by chemical formulas (10-1), (11-X1), and (11-X3),
a polyarylate resin including repeating units represented by a chemical formula (10-2), the chemical formula (11-X1), and the chemical formula (11-X3),
a polyarylate resin including repeating units represented by the chemical formula (10-2), the chemical formula (11-X1), and a chemical formula (11-X2), or
a polyarylate resin including repeating units represented by a chemical formula (10-3), the chemical formula (11-X1), and the chemical formula (11-X3)

### Claim 5 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
the binder resin includes a polycarbonate resin, and
the polycarbonate resin includes a repeating unit represented by a chemical formula (R-5) or (R-6)

### Claim 6 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
a ratio of a mass of the electron acceptor compound to a mass of the hole transport material is at least 0.01 and no greater than 0.30.

### Claim 7 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
the electron acceptor compound includes a compound represented by a general formula (20), (21), (22), (23), or (24),
where in the general formula (20), Q1, Q2, Q3, and Q4 each represent, independently of one another, an alkyl group having a carbon number of at least 1 and no greater than 6, an alkoxy group having a carbon number of at least 1 and no greater than 6, a cycloalkyl group having a carbon number of at least 5 and no greater than 7, or an aryl group having a carbon number of at least 6 and no greater than 14,
in the general formula (21), Q11 and Q12 each represent, independently of each other, an alkyl group having a carbon number of at least 1 and no greater than 6, an alkoxy group having a carbon number of at least 1 and no greater than 6, a cycloalkyl group having a carbon number of at least 5 and no greater than 7, or an aryl group having a carbon number of at least 6 and no greater than 14,
in the general formula (22), Q21 and Q22 each represent, independently of each other, an aryl group having a carbon number of at least 6 and no greater than 14 and optionally having an alkyl group having a carbon number of at least 1 and no greater than 6 or an alkoxy group having a carbon number of at least 1 and no greater than 6,
in the general formula (23), Q31 represents an alkoxycarbonyl group having a carbon number of at least 2 and no greater than 7, and
in the general formula (24), Q41 and Q42 each represent, independently of each other, an alkyl group having a carbon number of at least 1 and no greater than 6, and Q43 represents a halogen atom.

### Claim 8 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
the electron acceptor compound includes a compound represented by a chemical formula (20-E1), (20-E2), (21-E3), (22-E4), (23-E5), or (24-E6)

### Claim 9 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
the binder rein includes a polyarylate resin, and
the polyarylate resin includes at least one repeating unit represented by a general formula (10), a repeating unit represented by a chemical formula (11-X1), and at least one repeating unit represented by a general formula (11′),
where in the general formula (10),
R11 and R12 each represent, independently of each other, a hydrogen atom or a methyl group, and
R13 represents a hydrogen atom or an alkyl group having a carbon number of at least 1 and no greater than 4 and R14 represents an alkyl group having a carbon number of at least 1 and no greater than 4, or R13 and R14 bond together to represent a cycloalkylidene group having a carbon number of at least 5 and no greater than 14, and
X′ in the general formula (11′) represents a divalent group represented by a chemical formula (X2),

### Claim 10 (depends on 9)

The electrophotographic photosensitive member according to claim 9, wherein
the polyarylate resin includes repeating units represented by chemical formulas (10-2), (11-X1), and (11-X2),

### Claim 11 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
the binder rein includes a polycarbonate resin, and
the polycarbonate resin includes only a repeating unit represented by a chemical formula (R-6) as a repeating unit,

### Claim 12 (depends on 1)

The electrophotographic photosensitive member according to claim 1, wherein
the electron acceptor compound includes a compound represented by a general formula (22) or (23),
where in the general formula (22), Q21 and Q22 each represent, independently of each other, an aryl group having a carbon number of at least 6 and no greater than 14 and optionally having an alkyl group having a carbon number of at least 1 and no greater than 6 or an alkoxy group having a carbon number of at least 1 and no greater than 6, and
in the general formula (23), Q31 represents an alkoxycarbonyl group having a carbon number of at least 2 and no greater than 7.

### Claim 13 (depends on 12)

The electrophotographic photosensitive member according to claim 12, wherein
the compound represented by the general formula (22) is a compound represented by a chemical formula (22-E4), and
the compound represented by the general formula (23) is a compound represented by a chemical formula (23-E5),