Photoconductive imaging members

• US 6,214,504 B1
• Filed: 06/27/2000
• Issued: 04/10/2001
• Est. Priority Date: 06/27/2000
• Status: Expired due to Term

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Esteghamatian, Mohammad, Hor, Ah-Mee, Allen, C. Geoffrey, Duff, James M., Murti, Dasarao K.
• Primary Examiner(s): GOODROW, JOHN L
• Application Number:
  US09/604,243
• Time in Patent Office: 287 Days
• Field of Search: 430/58.65, 430/58.8, 430/59.1, 430/78
• US Class Current: 430/58.65
• CPC Class Codes: G03G 5/0657 containing seven relevant rings
• CPC Class Codes: G03G 5/0659 containing more than seven relevant rings

Abstract

A photoconductive imaging member containing a photogenerator layer comprised of a mixture of bis(methylbenzimidazo)perinone, optionally an (alkylimido)perylene, such as (n-pentylimido)perylene or mixtures of (n-pentylimido)perylene, bisbenzimidazo(2,1-a-1′,2′-b)anthra(2,1,9-def:6,5,10-d′e′f′)diisoquinoline-6,11-dione and bisbenzimidazo(2,1-a:2′,1′-a)anthra(2,1,9-def:6,5,10-d′e′f′)diisoquinoline-10,21-dione, and a charge transport layer.

Claims

1. A photoconductive imaging member comprised of a photogenerator layer comprised of bis(methylbenzimidazo)perinone, or (n-pentylimido)perylene, and bisbenzimidazo(2,1-a-1′

,2′

-b)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-6,11-dione and bisbenzimidazo(2,1-a;

2′

,1′

-a)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-10,21-dione, and a charge transport layer.

19. A photoconductive imaging member in accordance with claim 1 further containing on the substrate a barrier layer of a thickness of from about 0.1 to about 3 microns.

20. A photoconductive imaging member in accordance with claim 19 wherein the barrier layer is a polyester.

21. A method of imaging which comprises generating an electrostatic latent image on the imaging member of claim 1, developing the latent image, and optionally transferring the developed electrostatic image to a suitable substrate.

22. A method in accordance with claim 21 wherein said member is exposed to wavelengths of from about 680 to about 830 nanometers, respectively.

24. A photoconductive imaging member in accordance with claim 1 wherein a mixture of said bis(alkylbenzimidazo)perinone and said (alkylimido)perylene is present.

27. An imaging or printing apparatus containing the imaging member of claim 1.

2. A photoconductive imaging member comprised of a supporting substrate, photogenerator layer comprised of a mixture of bisbenzimidazo(2,1-a-1′

,2′

-b)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-6,11-dione and bisbenzimidazo(2,1-a;

2′

,1′

-a)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-10,21-dione, and a charge transport layer, and wherein said photogenerating layer further contains bis(methylbenzimidazo)perinone or (n-pentylimido)perylene.

3. A photoconductive imaging member in accordance with claim 2 wherein said bis(methylbenzimidazo)perinone, or said (n-pentylimido)perylene is present in an amount of from about 1 to about 50 weight percent.

4. A photoconductive imaging member in accordance with claim 2 wherein said bis(methylbenzimidazo)perinone, or said (n-pentylimido)perylene is present in an amount of from about 1 to about 25 weight percent.

5. A photoconductive imaging member in accordance with claim 2 wherein a mixture is present containing from about 75 to about 100 weight percent of bis(methylbenzimidazo)perinone, and from about zero (0) to about 25 weight percent of (n-pentylimido)perylene, and wherein the total of said two components in the mixture is about 100 percent.

6. A photoconductive imaging member in accordance with claim 2 wherein about 1 weight percent of (n-pentylimido)perylenes is present.

7. A photoconductive imaging member in accordance with claim 2 wherein a mixture of isomers of (n-pentylimido)perylenes or bismethyl benzimidazo)perinone is present.

8. A photoconductive imaging member in accordance with claim 2 wherein the photogenerator layer is situated between the substrate and the charge transport layer.

9. A photoconductive imaging member in accordance with claim 2 wherein the supporting substrate is comprised of a conductive substrate comprised of a metal.

10. A photoconductive imaging member in accordance with claim 2 wherein the substrate is a conductive substrate of aluminum, aluminized polyethylene terephthalate (MYLAR®

), or titanized polyethyl terephthalate wherein said MYLAR®

is of the formula

wherein n represents the number of segments.

11. A photoconductive imaging member in accordance with claim 2 wherein the photogenerator layer has a thickness of from about 0.05 to about 10 microns.

12. A photoconductive imaging member in accordance with claim 2 wherein the transport layer has a thickness of from about 5 to about 75 microns.

13. A photoconductive imaging member in accordance with claim 2 wherein the photogenerating layer is dispersed in a resinous binder in an amount of from about 5 percent by weight to about 95 percent by weight.

14. A photoconductive imaging member in accordance with claim 13 wherein the resinous binder is selected from the group consisting of polyesters, polyvinyl butyrals, polycarbonates, polystyrene-b-polyvinyl pyridine, and polyvinyl formals.

15. A photoconductive imaging member in accordance with claim 2 wherein said charge transport layers comprise aryl amine molecules.

16. A photoconductive imaging member in accordance with claim 15 wherein the aryl amines are of the formula

wherein X is selected from the group consisting of alkyl and halogen.

17. A photoconductive imaging member in accordance with claim 16 wherein alkyl contains from about 1 to about 10 carbon atoms.

18. A photoconductive imaging member in accordance with claim 16 wherein the aryl amines are molecules comprised of N,N′

-diphenyl-N,N-bis(3-methyl phenyl)-1,1′

-biphenyl-4,4′

-diamine.

23. A two-tier photoconductive imaging member comprised in the following sequence of a supporting substrate, a first hydroxygallium phthalocyanine photogenerator layer which absorbs light of a wavelength of from about 550 to about 950 nanometers, a first charge transport layer, a barrier layer, a second photogenerator layer comprised of a mixture of bis(methylbenzimidazo)perinone or (n-pentylimido)perylene, and bisbenzimidazo(2,1-a-1′

,2′

-b)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-6,11-dione and bisbenzimidazo(2,1-a;

2′

,1′

-a)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-10,21-dione (BZP), which absorbs light of a wavelength of from about 500 to about 800 nanometers, and thereover a second charge transport layer.

25. A process for forming an imaging member which comprises adding to a photoconductive imaging member containing (BZP) bisbenzimidazo(2,1-a-1′

,2′

-b)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-6,11-dione and bisbenzimidazo(2,1-a;

2′

,1′

-a)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-10,21-dione, and bis(alkylbenzimidazo)perinone, (alkylimido)perylene, or mixtures of (alkylimido)perylenes.

26. A process in accordance with claim 25 wherein said perinone is bis(methyl benzimidazo)perinone and said alkyl perylene is (n-pentylimido)perylene.

28. A photoconductive imaging member comprised of a photogenerator layer comprised of bis(alkylbenzimidazo)perinone, bisbenzimidazo(2,1-a-1′

,2′

-b)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-6,11-dione and bisbenzimidazo(2,1-a;

2′

,1′

-a)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-10,21-dione, and a charge transport layer.

30. A photoconductive imaging member in accordance with claim 28 wherein said perinone is a dopant.

32. A photoconductive imaging member in accordance with claim 30 wherein said dopant is present in an amount of from about 1 to about 7 weight percent.

35. A photoconductive imaging member in accordance with claim 28 wherein said perylene is of the formula, or mixtures thereof

wherein R₁ to R₈ are independently hydrogen, alkyl, alkoxy, aryl, or aryloxy.

29. A photoconductive imaging member comprised of a photogenerator layer comprised of (alkylimido)perylene, bisbenzimidazo(2,1-a-1′

,2′

-b)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-6,11-dione and bisbenzimidazo(2,1-a;

2′

,1′

-a)anthra(2,1,9-def;

6,5,10-d′

e′

f′

)diisoquinoline-10,21-dione, and a charge transport layer.

31. A photoconductive imaging member in accordance with claim 29 wherein said perylene is a dopant.

33. A photoconductive imaging member in accordance with claim 31 wherein said dopant is present in an amount of from about 1 to about 7 weight percent.

34. A photoconductive imaging member in accordance with claim 29 wherein said perylene is comprised of a mixture of perylenes.

36. A photoconductive imaging member in accordance with claim 29 wherein said perinone is of the formula, or mixtures thereof

wherein R₁ and R₂ are independently alkyl.