Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus

• US 6,416,915 B1
• Filed: 11/12/1999
• Issued: 07/09/2002
• Est. Priority Date: 11/13/1998
• Status: Expired due to Term

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Uematsu, Hiroki, Kikuchi, Toshihiro, Maruyama, Akio
• Primary Examiner(s): Dote, Janis L.
• Application Number:
  US09/438,529
• Time in Patent Office: 970 Days
• Field of Search: 430/56, 430/58.4, 430/58.45, 430/58.7, 430/59.6, 430/96, 430/66, 430/67, 430/73, 430/74, 430/75, 430/72, 399/116, 399/159
• US Class Current: 430/56
• CPC Class Codes: G03G 5/0666 containing a methine or polymethine group
• CPC Class Codes: G03G 5/0668 containing only one methine or polymethine group
• CPC Class Codes: G03G 5/071 obtained by reactions only involving carbon-to-carbon unsaturated bonds G03G5/078 takes precedence
• CPC Class Codes: G03G 5/0763 comprising arylamine moiety
• CPC Class Codes: G03G 5/0764 triarylamine
• CPC Class Codes: G03G 5/0765 alkenylarylamine
• CPC Class Codes: G03G 5/0767 comprising hydrazone moiety

Abstract

An electrophotographic photosensitive member is provided by forming a photosensitive layer on an electroconductive support. The photosensitive layer is provided with particularly excellent durability while retaining good electrophotographic performances when formed as a layer comprising a polymerizate of a hole-transporting compound having at least two chain polymerization function groups in its molecule represented by formula (1) below:

P¹_aAZ—(P²)_d)_b  (1),

wherein A denotes a hole-transporting group, P¹ and P² independently denote a chain polymerization function group and Z denotes a bonding organic group; a, b and d are independently an integer of at least 0 satisfying a+b×d≧2 provided that if a≧2. plural groups P¹ can be identical or different; if b≧2, plural groups Z can be identical or different; and if b×d≧2, plural groups P² can be identical or different.

Claims

1. An electrophotographic photosensitive member, comprising:

an electroconductive support and a photosensitive layer disposed on the electroconductive support;

wherein the photosensitive layer comprises a polymerizate of a hole-transporting compound having at least two chain polymerization function groups in its molecule represented by formula (1) below;

2. A photosensitive member according to claim 1, wherein the chain-polymerization function groups of the hole-transporting compound are represented by a formula selected from the group consisting of formulae (8)-(10) below:

wherein E denotes a hydrogen atom, a halogen atom, an alkyl group capable of having a substituent, an aralkyl group capable of having a substituent, an aryl group capable of having a substituent, CN group, nitro group, an alkoxy group, —

COOR¹⁸ or —

CONR¹⁹R²⁰ wherein R¹⁸-R²⁰ independently denote a hydrogen atom, a halogen atom, an alkyl group capable of having a substituent, an aralkyl group capable of having a substituent, or an aryl group capable of having a substituent; and

W denotes a divalent group selected from an arylene group capable of having a substituent;

an alkylene group capable of having a substituent;

—

COO—

, —

O—

, —

OO—

, —

S—

or —

CONR²¹;

wherein R²¹ denotes a hydrogen atom, a halogen atom, an alkyl group capable of having a substituent, an aralkyl group capable of having a substituent, or an aryl group capable of having a substituent; and

f is 0 or 1;

 

wherein R²² and R²³ independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aralkyl group capable of having a substituent, or an aryl group capable of having a substituent; and

g is an integer of 1-10;

 

wherein R²⁴ and R²⁵ independently denote a hydrogen atom, an alkyl group capable of having a substituent, an aralkyl group capable of having a substituent, or an aryl group capable of having a substituent; and

h is an integer of 0-10.

3. A photosensitive member according to claim 2, wherein the chain-polymerization function groups are represented by the formula (8).

4. A photosensitive member according to claim 2, wherein the chain-polymerization function groups are represented by the formula (9).

5. A photosensitive member according to claim 2, wherein the chain-polymerization function groups are represented by the formula (10).

6. A photosensitive member according to claim 1, wherein the chain-polymerization function groups of the hole-transporting compound are represented by a formula selected from formulae (11)-(17) below:

7. A photosensitive member according to claim 6, wherein the chain-polymerization function groups are represented by the formula (11) or (12).

8. A photosensitive member according to claim 1, wherein Z is an organic group obtained by selecting one member or combining at least two members arbitrarily selected from the group consisting of an alkylene group capable of having a substituent, an arylene group capable of having a substituent, —

CR²⁶═

CR²⁷—

(wherein R²⁶ and R²⁷ independently denote an alkyl group, an aryl group or a hydrogen atom), —

CO—

, —

SO—

, —

SO₂—

, an oxygen atom and a sulfur atom.

9. A photosensitive member according to claim 1, wherein the group A in the formula (1) is a group such that a combination of A with a number (a+b) of hydrogen atoms would provide a hole-transporting compound of the formula (4).

10. A photosensitive member according to claim 1, wherein the group A in the formula (1) is a group such that a combination of A with a number (a+b) of hydrogen atoms would provide a hole-transporting compound of the formula (6).

11. A photosensitive member according to claim 1, wherein the group A in the formula (1) is a group such that a combination of A with a number (a+b) of hydrogen atoms would provide a hole-transporting cyclic hydrocarbon compound having a group of the formula (5).

12. A photosensitive member according to claim 1, wherein the polymerizate of the hole-transporting compound comprises a three-dimensionally crosslinked structure.

13. A photosensitive member according to claim 1, wherein the electron beam is irradiated at an acceleration voltage of at most 300 kV.

14. A photosensitive member according to claim 1, wherein the electron beam is irradiated at a dose of 1-100 Mrad.

15. A photosensitive member according to claim 1, wherein Z in the formula (1) is an organic group represented by formula (18) or (19) below:

16. A process cartridge, comprising:

an electrophotographic photosensitive member and at least one means selected from the group consisting of charging means, developing means and cleaning means;

said electrophotographic photosensitive member and said at least one means being integrally supported and detachably mountable to a main assembly of an electrophotographic apparatus, wherein said electrophotographic photosensitive member is an electrophotographic photosensitive member according to any one of claims 1-8, 9-11, 12, 13, 14 and 15.

17. An electrophotographic apparatus, comprising:

an electrophotographic photosensitive member, and charging means, developing means and transfer means respectively disposed opposite to the electrophotographic photosensitive member,

wherein said electrophotographic photosensitive member is an electrophotographic photosensitive member according to any one of claims 1-8, 9-11, 12, 13, 14 and 15.