# US 4,396,696 A · Electrophotographic plate having azo compound photosensitive layer

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- Number: US 4,396,696 A
- Document ID: US4396696A
- Status: Granted
- Kind: A
- Application number: 06/363,883
- Filed: 1982-03-31
- Granted: 1983-08-02
- Earliest claimed: 1981-04-21
- Assignees: Mitsubishi Chemical Industries Limited
- Inventors: Hideki Nagasaka; Tetsuo Murayama
- Web page: https://patentgrep.com/patent/US4396696A

## CPC

- C09B 29/36: from heterocyclic compounds
- C09B 35/03: in which the coupling component is a heterocyclic compound
- C09B 35/378: Trisazo dyes of the type [IMAGE cpc-sch-C09B-1017.gif]
- G03G 5/0677: {Monoazo dyes}
- G03G 5/0681: {containing hetero rings in the part of the molecule between the azo-groups}
- G03G 5/0688: {containing hetero rings}
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY

## Abstract

An electrophotographic plate comprising an electroconductive substrate and a photosensitive layer coated thereon, wherein said photosensitive layer comprises an azo compound represented by the general formula (I) ##STR1## wherein A is a divalent group of an aromatic hydrocarbon or a divalent group of a heterocyclic ring containing at least one nitrogen atom in the ring, Ar is an aromatic hydrocarbon group or a heterocyclic group which may be bonded through a connecting group, and n is an integer of 1, 2 or 3.

## Claims

### Claim 1

An electrophotographic plate comprising an electroconductive substrate and a photosensitive layer coated thereon, wherein said photosensitive layer comprises an azo compound represented by the general formula (I) ##STR62## wherein A is a divalent group of an aromatic hydrocarbon or a divalent group of a heterocyclic ring containing at least one nitrogen atom in the ring, Ar is an aromatic hydrocarbon group or a heterocyclic group which may be bonded through a connecting group, and n is an integer of 1, 2 or 3.

### Claim 2 (depends on 1)

The electrophotographic plate according to claim 1 wherein A is an o-phenylene, o-naphthylene, perinaphthylene, 2,3-pyridinediyl or 4,5-pyrimidinediyl group, each of which may optionally have one or more substituents.

### Claim 3 (depends on 1)

The electrophotographic plate according to claim 1 wherein A is an o-phenylene or o-naphthylene group, each of which may optionally have one or more substituents.

### Claim 4 (depends on 2, 3)

The electrophotographic plate according to claim 2 or 3 wherein the substituent is selected from the group consisting of methyl, methoxy, nitro, chloro and hydroxy.

### Claim 5 (depends on 1)

The electrophotographic plate according to claim 1 wherein Ar is a phenyl group, a naphthyl group, a 1-pyrenyl group, a naphthylene group, an anthraquinonylene group, a biphenylene group, a bisphenylene group represented by the general formula: ##STR63## where Y is --O--, --S--, --CH.sub.2 --, --CH.dbd.CH--, ##STR64## or a naphthoylenebenzimidazolyl group, each of which may optionally have one or more substituents.

### Claim 6 (depends on 5)

The electrophotographic plate according to claim 5 wherein the substituent is selected from the group consisting of nitro, cyano, methyl, ethoxy and chloro.

### Claim 7 (depends on 1)

The electrophotographic plate according to claim 1 wherein Ar is ##STR65##

### Claim 8 (depends on 1, 2, 3, 4, 5, 6, 7)

The electrophotographic plate according to any one of claims 1 to 7 wherein the photosensitive layer comprises a charge-generating layer containing the azo compound of claim 1 and a charge-transporting layer coated thereon and containing a pyrazoline compound represented by the general formula (VI) ##STR66## where Ar.sup.1, Ar.sup.2 and Ar.sup.3 are independently substituted or unsubstituted aromatic hydrocarbon groups or aromatic heterocyclic groups, and n is an integer of 0 or 1.

### Claim 9 (depends on 1, 2, 3, 4, 5, 6, 7)

The electrophotographic plate according to any one of claims 1 to 7 wherein the photosensitive layer comprises a charge-generating layer containing the azo compound of claim 1 and a charge transporting layer coated thereon and containing a hydrazone compound represented by the general formula (VII) ##STR67## where Ar.sup.4 is a substituted or unsubstituted aromatic hydrocarbon group or aromatic heterocyclic group, R.sup.1 and R.sup.2 are independently alkyl, aryl or aralkyl, and l is an integer of 1 or 2.

### Claim 10 (depends on 1)

The electrophotographic plate according to claim 1 wherein the azo compound is pulverized into fine particles having a particle size of at most 5.mu..