# US 2013/0280652 A1 · P-terphenyl compound mixture and electrophotographic photoreceptors made by using the same

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- Number: US 2013/0280652 A1
- Document ID: US20130280652A1
- Status: Published application
- Kind: A1
- Application number: 13/916,110
- Filed: 2013-06-12
- Published: 2013-10-24
- Earliest claimed: 2006-01-25
- Assignees: Hodogaya Chemical Co., Ltd.
- Applicants: Hodogaya Chemical Co., Ltd.
- Inventors: Shinya NAGAI; Atsushi Takesue; Makoto Koike; Katsumi Abe; Takehiro Nakajima
- Web page: https://patentgrep.com/patent/US20130280652A1

## CPC

- G03G 5/061446: {terphenyl-diamine}
- C07C 211/54: having amino groups bound to two or three six-membered aromatic rings
- G03G 5/0618: {containing oxygen and nitrogen}
- G03G 5/0696: {Phthalocyanines}
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

An object of the invention is to provide a method of making a p-terphenyl compound mixture which includes two symmetric p-terphenyl compounds respectively represented by formula (1) and formula (2) and an asymmetric p-terphenyl compound represented by formula (3)

## Claims

### Claim 1

A p-terphenyl compound mixture which comprises two symmetric p-terphenyl compounds respectively represented by the following general formula (1) and general formula (2) and an asymmetric p-terphenyl compound represented by the following general formula (3) which has both a group of substituents of the compound represented by general formula (1) and a group of substituents of the compound represented by general formula (2):
wherein R1, R2, R3, R4, R5, R6, R7, and R8 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aralkyl group, a halogen atom, a di-substituted amino group, or a substituted or unsubstituted phenyl group, provided that R1 and R2, R3 and R4, R5 and R6, and R7 and R8 may collectively form a ring, and that the group of the substituents R5, R6, R7, and R8 differ from the group of the substituents R1, R2, R3, and R4 in at least one substituent or substitution position.

### Claim 2 (depends on 1)

The p-terphenyl compound mixture according to claim 1, wherein the content of the p-terphenyl compound represented by general formula (1) is 50-80% by mass.

### Claim 3

A p-terphenyl compound mixture for electrophotographic photoreceptors which comprises two symmetric p-terphenyl compounds respectively represented by the following general formula (1) and general formula (2) and an asymmetric p-terphenyl compound represented by the following general formula (3) which has both a group of substituents of the compound represented by general formula (1) and a group of substituents of the compound represented by general formula (2):
wherein R1, R2, R3, R4, R5, R6, R7, and R8 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aralkyl group, a halogen atom, a di-substituted amino group, or a substituted or unsubstituted phenyl group, provided that R1 and R2, R3 and R4, R5 and R6, and R7 and R8 may collectively form a ring, and that the group of the substituents R5, R6, R7, and R8 differ from the group of the substituents R1, R2, R3, and R4 in at least one substituent or substitution position.

### Claim 4 (depends on 3)

The p-terphenyl compound mixture for electrophotographic photoreceptors according to claim 3, wherein the content of the p-terphenyl compound represented by general formula (1) is 50-80% by mass.

### Claim 5 (depends on 1)

An electrophotographic photoreceptor which has a layer containing the p-terphenyl compound mixture according to claim 1.

### Claim 6 (depends on 5)

The electrophotographic photoreceptor according to claim 5, wherein the content of the p-terphenyl compound represented by general formula (1) in the p-terphenyl compound mixture is 50-80% by mass.

### Claim 7 (depends on 1)

A process for producing the p-terphenyl compound mixture according to claim 1, the process comprising obtaining the target mixture from two diphenylamine compounds respectively represented by the following general formula (4) and general formula (5) and 4,4″-diiodo-p-terphenyl through a one-stage reaction:
wherein R1, R2, R3, R4, R5, R6, R7, and R8 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aralkyl group, a halogen atom, a di-substituted amino group, or a substituted or unsubstituted phenyl group, provided that R1 and R2, R3 and R4, R5 and R6, and R7 and R8 may collectively form a ring, and that the group of the substituents R5, R6, R7, and R8 differ from the group of the substituents R1, R2, R3, and R4 in at least one substituent or substitution position.

### Claim 8 (depends on 1)

A method of preventing an electrophotographic photoreceptor from cracking, comprising using the p-terphenyl compound mixture according to claim 1.

### Claim 9 (depends on 8)

The method of preventing an electrophotographic photoreceptor from cracking according to claim 8, wherein the content of the p-terphenyl compound represented by general formula (1) in the p-terphenyl compound mixture is 50-80% by mass.

### Claim 10 (depends on 1)

A method of preventing an electrophotographic photoreceptor from cracking by improving solubility in organic solvents, comprising using the p-terphenyl compound mixture according to claim 1.

### Claim 11 (depends on 10)

The method of preventing an electrophotographic photoreceptor from cracking by improving solubility in organic solvents according to claim 10, wherein the content of the p-terphenyl compound represented by general formula (1) in the p-terphenyl compound mixture is 50-80% by mass.