# US 5,707,766 A · Electrophotographic photosensitive material

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- Number: US 5,707,766 A
- Document ID: US5707766A
- Status: Granted
- Kind: A
- Application number: 08/521,741
- Filed: 1995-08-31
- Granted: 1998-01-13
- Earliest claimed: 1994-09-01
- Assignees: Fuji Electric Co., Ltd.
- Inventors: Sumitaka Nogami; Michihiro Kitazawa
- Web page: https://patentgrep.com/patent/US5707766A

## CPC

- G03G 5/047: characterised by the charge-generation layers or charge transport layers {(G03G5/0433 and G03G5/0436 take precedence)}
- G03G 5/0517: {comprising one or more cyclic groups consisting of carbon-atoms only}
- G03G 5/0609: {containing oxygen}
- G03G 5/062: {containing non-metal elements other than hydrogen, halogen, oxygen or nitrogen}
- G03G 5/064: {containing three hetero atoms}
- Y10S 430/103: Radiation sensitive composition or product containing specified antioxidant
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

An electrophotographic photoconductor includes an electroconductive substrate and a photosensitive layer which is provided on the electroconductive substrate and which includes a charge generating agent, a hole charge transporting agent, and antioxidant composed of at least two antioxidant materials. In a second embodiment, the electrophotographic photoconductor includes an electroconductive substrate and a photosensitive layer which is provided on the electroconductive substrate and which includes a charge generating layer containing a charge generating agent and a charge transporting layer containing a hole charge transporting agent, and antioxidant composed of at least two antioxidant materials.

## Claims

### Claim 1

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating layer containing a charge generating agent and a charge transporting layer containing a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.1): ##STR10## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one hindered phenol of formula (B.sub.1): ##STR11## wherein R.sub.1 to R.sub.5 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 2

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating layer containing a charge generating agent and a charge transporting layer containing a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.1): ##STR12## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one quinone of any of formulae (B.sub.2): ##STR13## wherein R.sub.6 to R.sub.25 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, atkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 3

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating layer containing a charge generating agent and a charge transporting layer containing a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.1): ##STR14## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one hydroquinone of formula (B.sub.3): ##STR15## wherein R.sub.26 to R.sub.29 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 4

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating layer containing a charge generating agent and a charge transporting layer containing a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.2): ##STR16## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one hindered phenol of formula (B.sub.1): ##STR17## wherein R.sub.1 to R.sub.4 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 5

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating layer containing a charge generating agent and a charge transporting layer containing a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.2): ##STR18## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one quinone of any of formulae (B.sub.2): ##STR19## wherein R.sub.1 to R.sub.25 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 6

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating layer containing a charge generating agent and a charge transporting layer containing a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.2): ##STR20## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one hydroquinone of formula (B.sub.3): ##STR21## wherein R.sub.26 to R.sub.29 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 7

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating agent, a hole charge transporting agent and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.1): ##STR22## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, and alkyl group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one hindered phenol of formula (B.sub.1): ##STR23## wherein R.sub.1 to R.sub.5 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 8

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating agent, a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.1): ##STR24## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one quinone of any of formulae (B.sub.2): ##STR25## wherein R.sub.6 to R.sub.25 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 9

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating agent, a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.1): ##STR26## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one hydroquinone of formula (B.sub.3): ##STR27## wherein R.sub.26 to R.sub.29 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 10

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating agent, a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.2): ##STR28## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one hindered phenol of formula (B.sub.1): ##STR29## wherein R.sub.1 to R.sub.4 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 11

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating agent, a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.2): ##STR30## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one quinone of any of formulae (B.sub.2): ##STR31## wherein R.sub.1 to R.sub.25 are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.

### Claim 12

An electrophotographic photoconductor, comprising:
an electroconductive substrate; and
a photosensitive layer which is provided on said electroconductive substrate and which comprises a charge generating agent, a hole charge transporting agent, and antioxidant comprised of at least two antioxidant materials,
wherein the antioxidant comprised of at least two antioxidant materials contains:
(a) at least one hydrobenzoin compound of formula (A.sub.2): ##STR32## wherein R and R' are independently selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aryl group optionally having a substituent, and an aralkyl group optionally having a substituent, and
(b) at least one hydroquinone of formula (B.sub.3): ##STR33## wherein R.sub.26 to R.sub.29, are independently selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted aryloxy, alkylthio, arylthio, alkylamino, arylamino, acyl, alkylacylamino, arylacylamino, alkylcarbamoyl, arylcarbamoyl, alkylsulfonamide, arylsulfonamide, alkylsulfamoyl, arylsulfamoyl, alkylsulfonyl, arylsulfonyl, alkyloxycarbonyl, aryloxcarbonyl, alkylacyloxy, arylacyloxy, silyl, or heterocyclic group.