Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus

• US 6,146,800 A
• Filed: 10/16/1998
• Issued: 11/14/2000
• Est. Priority Date: 10/17/1997
• Status: Expired due to Term

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Inventors: Yoshida, Akira, Anayama, Hideki
• Primary Examiner(s): Dote, Janis L.
• Application Number:
  US09/173,440
• Time in Patent Office: 760 Days
• Field of Search: 430/59.6, 430/96, 430/56, 430/66, 430/67, 399/159, 399/116, 525/437, 525/461
• US Class Current: 430/67
• CPC Class Codes: G03G 5/0564 Polycarbonates
• CPC Class Codes: G03G 5/0578 Polycondensates comprising silicon atoms in the main chain

Abstract

An electrophotographic photosensitive member is disclosed which is provided with a surface layer containing a polyarylate resin or polycarbonate resin. The polyarylate resin and polycarbonate resin have a structural unit having a cyclic siloxane structure in its backbone chain. Also a process cartridge and an electrophotographic apparatus using the photosensitive member are disclosed.

Claims

1. An electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided on the conductive support;

said electrophotographic photosensitive member having a surface layer which contains a polyarylate resin or polycarbonate resin having a structural unit having a cyclic siloxane structure in its backbone chain.

2. The electrophotographic photosensitive member according to claim 1, wherein said surface layer contains the polyarylate resin.

3. The electrophotographic photosensitive member according to claim 2, wherein the structural unit having a cyclic siloxane structure of said polyarylate resin is represented by the following Formula (1) ##STR20## wherein R₁ to R₄ and R₂₁ to R₂₈ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group or a substituted or unsubstituted aryl group;

R₅ to R₂₀ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₁ to X₄ are the same or different and each represent a substituted or unsubstituted alkylene group;

a represents an integer of 0 to 100;

b, c, d and e are the same or different and each represent an integer which is 0 to 10 and wherein b+c≧

2 and d+e≧

2; and

f represents an integer of 0 to 10.

4. The electrophotographic photosensitive member according to claim 3, wherein said polyarylate resin further has a structural unit represented by the following Formula (2) ##STR21## wherein R₂₉ to R₄₀ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₅ represents a single bond, --O--, --S-- or a group represented by the following formula;

##STR22## wherein R₄₁ and R₄₂ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

or R₄₁ and R₄₂ are joined together to form a substituted or unsubstituted cycloalkylidene group together with the intervening carbon atom.

5. The electrophotographic photosensitive member according to claim 4, wherein R₁ to R₄, R₂₁ to R₂₈, R₃₀, R₃₁, R₃₃, R₃₆ to R₃₉ and R₄₀ are all hydrogen atoms.

6. The electrophotographic photosensitive member according to claim 1, wherein said surface layer contains the polycarbonate resin.

7. The electrophotographic photosensitive member according to claim 6, wherein the structural unit having a cyclic siloxane structure of said polycarbonate resin is represented by the following Formula (3) ##STR23## wherein R₄₃ to R₄₆ and R₆₃ to R₆₆ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group or a substituted or unsubstituted aryl group;

R₄₇ to R₆₂ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₆ to X₉ are the same or different and each represent a substituted or unsubstituted alkylene group;

g represents an integer of 0 to 100;

h, i, j and k are the same or different and each represent an integer which is 0 to 10 and wherein h+i≧

2 and j+k≧

2; and

represents an integer of 0 to 10.

8. The electrophotographic photosensitive member according to claim 7, wherein said polycarbonate resin further has a structural unit represented by the following Formula (4) ##STR24## wherein R₆₇ to R₇₄ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₁₀ represents a single bond, --O--, --S-- or a group represented by the following formula;

##STR25## wherein R₇₅. and R₇₆ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

or R₇₅ and R₇₆ are joined together to form a substituted or unsubstituted cycloalkylidene group together with the intervening carbon atom.

9. The electrophotographic photosensitive member according to claim 8, wherein R₄₃ to R₄₆, R₆₃ to R₆₆, R₆₈, R₆₉, R₇₁ and R₇₄ are all hydrogen atoms.

10. A process cartridge comprising an electrophotographic photosensitive member and at least one means selected from the group consisting of a charging means, a developing means and a cleaning means;

said electrophotographic photosensitive member and said at least one means being supported as one unit and being detachably mountable to the main body of an electrophotographic apparatus; and

said electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided on the conductive support;

said electrophotographic photosensitive member having a surface layer which contains a polyarylate resin or polycarbonate resin having a structural unit having a cyclic siloxane structure in its backbone chain.

11. The process cartridge according to claim 10, wherein said surface layer of the electrophotographic photosensitive member contains the polyarylate resin.

12. The process cartridge according to claim 11, wherein the structural unit having a cyclic siloxane structure of said polyarylate resin is represented by the following Formula (1) ##STR26## wherein R₁ to R₄ and R₂₁ to R₂₈ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group or a substituted or unsubstituted aryl group;

R₅ to R₂₀ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₁ to X₄ are the same or different and each represent a substituted or unsubstituted alkylene group;

a represents an integer of 0 to 100;

b, c, d and e are the same or different and each represent an integer which is 0 to 10 and wherein b+c≧

2 and d+e≧

2; and

f represents an integer of 0 to 10.

13. The process cartridge according to claim 12, wherein said polyarylate resin further has a structural unit represented by the following Formula (2) ##STR27## wherein R₂₉ to R₄₀ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₅ represents a single bond, --O--, --S-- or a group represented by the following formula;

##STR28## wherein R₄₁ and R₄₂ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

or R₄₁ and R₄₂ are joined together to form a substituted or unsubstituted cycloalkylidene group together with the intervening carbon atom.

14. The process cartridge according to claim 13, wherein R₁ to R₄, R₂₁ to R₂₈, R₃₀, R₃₁, R₃₃, R₃₆ to R₃₉ and R₄₀ are all hydrogen atoms.

15. The process cartridge according to claim 10, wherein said surface layer of the electrophotographic photosensitive member contains the polycarbonate resin.

16. The process cartridge according to claim 15, wherein the structural unit having a cyclic siloxane structure of said polycarbonate resin is represented by the following Formula (3) ##STR29## wherein R₄₃ to R₄₆ and R₆₃ to R₆₆ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group or a substituted or unsubstituted aryl group;

R₄₇ to R₆₂ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₆ to X₉ are the same or different and each represent a substituted or unsubstituted alkylene group;

g represents an integer of 0 to 100;

h, i, j and k are the same or different and each represent an integer which is 0 to 10 and wherein h+i≧

2 and j+k≧

2; and

l represents an integer of 0 to 10.

17. The process cartridge according to claim 16, wherein said polycarbonate resin further has a structural unit represented by the following Formula (4) ##STR30## wherein R₆₇ to R₇₄ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₁₀ represents a single bond, --O--, --S-- or a group represented by the following formula;

##STR31## wherein R₇₅ and R₇₆ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

or R₇₅ and R₇₆ are joined together to form a substituted or unsubstituted cycloalkylidene group together with the intervening carbon atom.

18. The process cartridge according to claim 17, wherein R₄₃ to R₄₆, R₆₃ to R₆₆, R₆₈, R₆₉, R₇₁ and R₇₄ are all hydrogen atoms.

19. An electrophotographic apparatus comprising an electrophotographic photosensitive member, a charging means, an exposure means, a developing means and a transfer means;

said electrophotographic photosensitive member comprising a conductive support and a photosensitive layer provided on the conductive support;

said electrophotographic photosensitive member having a surface layer which contains a polyarylate resin or polycarbonate resin having a structural unit having a cyclic siloxane structure in its backbone chain.

20. The electrophotographic apparatus according to claim 19, wherein said surface layer of the electrophotographic photosensitive member contains the polyarylate resin.

21. The electrophotographic apparatus according to claim 20, wherein the structural unit having a cyclic siloxane structure of said polyarylate resin is represented by the following Formula (1) ##STR32## wherein R₁ to R₄ and R₂₁ to R₂₈ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group or a substituted or unsubstituted aryl group;

R₅ to R₂₀ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₁ to X₄ are the same or different and each represent a substituted or unsubstituted alkylene group;

a represents an integer of 0 to 100;

b, c, d and e are the same or different and each represent an integer which is 0 to 10 and wherein b+c≧

2 and d+e≧

2; and

f represents an integer of 0 to 10.

22. The electrophotographic apparatus according to claim 21, wherein said polyarylate resin further has a structural unit represented by the following Formula (2) ##STR33## wherein R₂₉ to R₄₀ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₅ represents a single bond, --O--, --S-- or a group represented by the following formula;

##STR34## wherein R₄₁ and R₄₂ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

or R₄₁ and R₄₂ are joined together to form a substituted or unsubstituted cycloalkylidene group together with the intervening carbon atom.

23. The electrophotographic apparatus according to claim 22, wherein R₁ to R₄, R₂₁ to R₂₈, R₃₀, R₃₁, R₃₃, R₃₆ to R₃₉ and R₄₀ are all hydrogen atoms.

24. The electrophotographic apparatus according to claim 19, wherein said surface layer of the electrophotographic photosensitive member contains the polycarbonate resin.

25. The electrophotographic apparatus according to claim 24, wherein the structural unit having a cyclic siloxane structure of said polycarbonate resin is represented by the following Formula (3) ##STR35## wherein R₄₃ to R₄₆ and R₆₃ to R₆₆ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxyl group or a substituted or unsubstituted aryl group;

R₄₇ to R₆₂ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₆ to X₉ are the same or different and each represent a substituted or unsubstituted alkylene group;

g represents an integer of 0 to 100;

h, i, j and k are the same or different and each represent an integer which is 0 to 10 and werein h+i≧

2 and j+k≧

2; and

l represents an integer of 0 to 10.

26. The electrophotographic apparatus according to claim 25, wherein said polycarbonate resin further has a structural unit represented by the following Formula (4) ##STR36## wherein R₆₇ to R₇₄ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

X₁₀ represents a single bond, --O--, --S-- or a group represented by the following formula;

##STR37## wherein R₇₅ and R₇₆ are the same or different and each represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group;

or R₇₅ and R₇₆ are joined together to form a substituted or unsubstituted cycloalkylidene group together with the intervening carbon atom.

27. The electrophotographic apparatus according to claim 26, wherein R₄₃ to R₄₆, R₆₃ to R₆₆, R₆₈, R₆₉, R₇₁ and R₇₄ are all hydrogen atoms.