Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus, and process for producing the same photosensitive member

• US 6,180,303 B1
• Filed: 06/11/1999
• Issued: 01/30/2001
• Est. Priority Date: 06/12/1998
• 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): GOODROW, JOHN L
• Application Number:
  US09/330,602
• Time in Patent Office: 599 Days
• Field of Search: 430/59.6, 430/58.85, 399/156
• US Class Current: 430/59.6
• CPC Class Codes: G03G 5/071 obtained by reactions only involving carbon-to-carbon unsaturated bonds G03G5/078 takes precedence
• CPC Class Codes: G03G 5/075 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds G03G5/078 takes precedence
• CPC Class Codes: G03G 5/0764 triarylamine
• CPC Class Codes: G03G 5/0765 alkenylarylamine

Abstract

An electrophotographic photosensitive member, process cartridge and electrophotographic apparatus which use the same photosensitive member, and process for producing the same photosensitive member. The electrophotographic photosensitive member, includes a support and photosensitive layer thereon, wherein said photosensitive layer contains at least one of a hole-transporting compound with two or more chain-polymerizing functional groups in the same molecule and the compound hardened by polymerizing or cross-linking the above hole-transporting compound.

Claims

1. An electrophotographic photosensitive member, comprising a support and photosensitive layer thereon, wherein said photosensitive layer contains at least one of a hole-transporting compound with two or more chain-polymerizing functional groups in the same molecule and the compound hardened by polymerizing or cross-linking the above hole-transporting compound.

2. The electrophotographic photosensitive member according to claim 1, wherein said hole-transporting compound is shown by the general formula (1):

wherein A is a hole-transporting group;

P¹ and P² are each a chain-polymerizing functional group, and may be the same or different;

Z is an organic residue which may have a substituent;

Y is hydrogen atom; and

a, b and d are each an integer of 0 or more, where b+d is an integer of 3 or more when a is zero, a is an integer of 2 or more when b or d is zero, and a+b+d is an integer of 3 or more in all other cases; and

P¹ may be the same or different when a is 2 or more, P² may be the same or different when d is 2 or more, and Z may be the same or different when b is 2 or more.

3. The electrophotographic photosensitive member according to claim 2, wherein Z in the general formula (1) is an alkylene group which may have a substituent;

arylene group which may have a substituent;

CR¹═

CR² (wherein R¹ and R² are each an alkyl group which may have a substituent, aryl group which may have a substituent, or hydrogen atom, and may be the same or different);

C═

O , S═

O, SO₂, or organic residue containing at least one of oxygen and sulfur atoms, which may be arbitrarily combined with each other.

4. The electrophotographic photosensitive member according to claim 3, wherein Z in the general formula (1) is shown by the following general formula (2):

wherein, X¹ to X³ are each an alkylene group which may have a substituent, (CR¹═

CR²)_m, C═

O, S═

O, SO₂, or oxygen or sulfur atom;

Ar¹ and Ar² are each an aryl group which may have a substituent;

R¹ and R² are each an alkyl group which may have a substituent, aryl group which may have a substituent or hydrogen atom, where R¹ and R² may be the same or different; and

m is an integer of 1 to 5 and p to t are each an integer of 0 to 10, where p to t are not simultaneously zero.

5. The electrophotographic photosensitive member according to claim 4, wherein Z in the general formula (1) is shown by the following general formula (3):

wherein, Ar³ is an arylene group which may have a substituent;

X⁴ and X⁵ are each (CH₂)_m′

, (CH═

CR³)_n′

, C═

O or oxygen atom;

R³ is an alkyl group which may have a substituent, aryl group which may have a substituent or hydrogen atom; and

m is an integer of 1 to 10, n is an integer of 1 to 5 and u to w are each an integer of 0 to 10, where u to w are not simultaneously zero.

6. The electrophotographic photosensitive member according to claim 2, wherein each of P′

and Z in A is substituted by hydrogen atom to form a hydrogen adduct shown by the following general formula (4);

wherein, R⁴, R⁵ and R⁶ are each an alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent, R⁴, R⁵ and R⁶ may be the same or different, and at least two of them are aryl groups.

7. The electrophotographic photosensitive member according to claim 6, wherein all of R⁴, R⁵ and R⁶ are an aryl group.

8. The electrophotographic photosensitive member according to claim 2, wherein at least one of P¹ and P² is an unsaturated polymerizing functional group shown by the following general formula (5):

wherein, E is hydrogen atom, a halogen atom, alkyl group which may have a substituent, aralkyl group which may have a substituent, aryl group which may have a substituent, cyano group, nitro group, alkoxy group, —

COOR⁷ (wherein R⁷ is hydrogen atom, a halogen atom, alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent), CONR⁸R⁹ (R⁸ and R⁹ are each hydrogen atom, a halogen atom, alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent, where R⁸ and R⁹ may be the same or different); and

W is an arylene group which may have a substituent, alkylene group which may have a substituent, or —

COO—

, —

CH₂—

, —

O—

, —

OO—

, —

S—

or CONR¹⁰—

(wherein R¹⁰ is hydrogen atom, a halogen atom, alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent); and

f is 0 or 1.

9. The electrophotographic photosensitive member according to claim 2, wherein at least one of P¹ and P² is a cyclic ether group shown by the following general formula (6):

wherein R¹¹ and R¹² are each hydrogen atom, an alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent; and

g is an integer of 1 to 10.

10. The electrophotographic photosensitive member according to claim 2, wherein at least one of P¹ and P² is an alicyclic epoxy group shown by the following general formula (7):

wherein R¹³ and R¹⁴ are each hydrogen atom, an alkyl group which may have a substituent, aralkyl group which may have a substituent;

or aryl group which may have a substituent; and

h is an integer of 0 to 10.

11. The electrophotographic photosensitive member according to claim 2, wherein at least one of P¹ and P² is shown by the formula selected from the group consisting of formulae (8) to (14):

wherein i is an integer of 1 to 3

wherein j is an integer of 1 to 3.

12. The electrophotographic photosensitive member according to claim 11, wherein at least one of P¹ and P² is shown by the formula selected from the group consisting of formulae (8) and (9):

13. A process cartridge comprising an electrophotographic photosensitive member and at least one of the means selected from the group consisting of those for electrification, development and cleaning,

wherein said electrophotographic photosensitive member and at least one of said means are monolithically supported to form an assembly freely attachable to or detachable from an electrophotographic apparatus body, and

said electrophotographic photosensitive member comprises a support and photosensitive layer thereon, said photosensitive layer containing at least one of a hole-transporting compound with two or more chain-polymerizing functional groups in the same molecule and the compound hardened by polymerizing or cross-linking the above hole-transporting compound.

14. An electrophotographic apparatus comprising an electrophotographic photosensitive member, and means for electrification, exposure, development and transferring,

said electrophotographic photosensitive member comprising a support and photosensitive layer thereon,

wherein said photosensitive layer contains at least one of a hole-transporting compound with two or more chain-polymerizing functional groups in the same molecule and the compound hardened by polymerizing or cross-linking the above hole-transporting compound.

15. A process for producing an electrophotographic photosensitive member which has a support and photosensitive layer thereon, comprising a step for forming a photosensitive layer for said electrophotographic photosensitive member,

wherein said step hardens a hole-transporting compound with two or more chain-polymerizing functional groups in the same molecule by polymerization or cross-linking.

16. The process for producing an electrophotographic photosensitive member according to claim 15, wherein said hole-transporting compound is shown by the general formula (1):

wherein A is a hole-transporting group;

P¹ and P² are each a chain-polymerizing functional group, and may be the same or different;

Z is an organic residue which may have a substituent;

Y is hydrogen atom; and

a, b and d are each an integer of 0 or more, where b+d is an integer of 3 or more when a is zero, a is an integer of 2 or more when b or d is zero, and a+b+d is an integer of 3 or more in all other cases; and

P¹ may be the same or different when a is 2 or more, P² may be the same or different when d is 2 or more, and Z may be the same or different when b is 2 or more.

17. The process for producing an electrophotographic photosensitive member according to claim 16, wherein Z in the general formula (1) is an alkylene group which may have a substituent;

arylene group which may have a substituent;

CR¹═

CR² (wherein R¹ and R² are each an alkyl group which may have a substituent, aryl group which may have a substituent, or hydrogen atom, and may be the same or different);

C═

O , S═

O, SO₂, or organic residue containing at least one of oxygen and sulfur atoms, which may be arbitrarily combined with each other.

18. The process for producing an electrophotographic photosensitive member according to claim 17, wherein Z in the general formula (1) is shown by the following general formula (2):

wherein, X¹ to X³ are each an alkylene group which may have a substituent, (CR¹═

CR²)_m, C═

O, S═

O, SO₂, or oxygen or sulfur atom;

Ar¹ and Ar² are each an arylene group which may have a substituent;

R¹ and R² are each an alkyl group which may have a substituent, aryl group which may have a substituent or hydrogen atom, where R¹ and R² may be the same or different; and

m is an integer of 1 to 5 and p to t are each an integer of 0 to 10, where p to t are not simultaneously zero.

19. The process for producing an electrophotographic photosensitive member according to claim 18, wherein Z in the general formula (1) is shown by the following general formula (3):

wherein, Ar³ is an arylene group which may have a substituent;

X⁴ and X⁵ are each (CH₂)_m′

, (CH═

CR³)_n′

, C═

O or oxygen atom;

R³ is an alkyl group which may have a substituent, aryl group which may have a substituent or hydrogen atom; and

m is an integer of 1 to 10, n is an integer of 1 to 5 and u to w are each an integer of 0 to 10, where u to w are not simultaneously zero.

20. The process for producing an electrophotographic photosensitive member according to claim 16, wherein each of P¹ and Z in A is substituted by hydrogen atom to form a hydrogen adduct shown by the following general formula (4):

wherein, R⁴, R⁵ and R⁶ are each an alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent, R⁴, R⁵ and R⁶ may be the same or different, and at least two of them are aryl groups.

21. The process for producing an electrophotographic photosensitive member according to claim 20, wherein all of R⁴, R⁵ and R⁶ are an aryl group.

22. The process for producing an electrophotographic photosensitive member according to claim 16, wherein at least one of P¹ and P² is an unsaturated polymerizing functional group shown by the following general formula (5):

wherein E is hydrogen atom, a halogen atom, alkyl group which may have a substituent, aralkyl group which may have a substituent, aryl group which may have a substituent, cyano group, nitro group, alkoxy group, —

COOR⁷ (wherein R⁷ is hydrogen atom, a halogen atom, alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent), CONR⁸R⁹ (wherein R⁸ and R⁹ are each hydrogen atom, a halogen atom, alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent, where R⁸ and R⁹ may be the same or different); and

W is an arylene group which may have a substituent, alkylene group which may have a substituent, or —

COO—

, —

CH₂—

, —

O—

, —

OO—

, —

S—

or CONR¹⁰—

(wherein R¹⁰ is hydrogen atom, a halogen atom, alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent); and

f is 0 or 1.

23. The process for producing an electrophotographic photosensitive member according to claim 16, wherein at least one of P¹ and P² is a cyclic ether group shown by the following general formula (6):

wherein R¹¹ and R¹² are each hydrogen atom, an alkyl group which may have a substituent, aralkyl group which may have a substituent, or aryl group which may have a substituent; and

g is an integer of 1 to 10.

24. The process for producing an electrophotographic photosensitive member according to claim 16, wherein at least one of P¹ and P² is an alicyclic epoxy group shown by the following general formula (7):

wherein R¹³ and R¹⁴ are each hydrogen atom, an alkyl group which may have a substituent, aralkyl group which may have a substituent;

or aryl group which may have a substituent; and

h is an integer of 0 to 10.

25. The process for producing an electrophotographic photosensitive member according to claim 16, wherein at least one of P¹ and P² is shown by the formula selected from the group consisting of formulae (8) to (14):

wherein i is an integer of 1 to 3

wherein j is an integer of 1 to 3.

26. The process for producing an electrophotographic photosensitive member according to claim 25, wherein at least one of P¹ and P² is shown by the formula selected from the group consisting of formulae (8) and (9):

27. The process for producing an electrophotographic photosensitive member according to claim 15, wherein said polymerization/cross-linking is effected by the aid of one of radioactive ray, heat and light.

28. The process for producing an electrophotographic photosensitive member according to claim 27, wherein said polymerization/cross-linking is effected by the aid of radioactive ray.

29. The process for producing an electrophotographic photosensitive member according to claim 28, wherein said radioactive ray is electron ray.

30. The process for producing an electrophotographic photosensitive member according to claim 28, wherein said polymerization/cross-linking is effected without using a polymerization initiator.

31. The process for producing an electrophotographic photosensitive member according to claim 28, wherein said electrophotographic photosensitive member is irradiated with electron ray at an acceleration voltage of 300 KV or less.

32. The process for producing an electrophotographic photosensitive member according to claim 28, wherein said electrophotographic photosensitive member is irradiated with electron ray at a dose of 1 to 100 Mrad.