Photoconductive imaging members with imidazole perinones

• US 4,808,506 A
• Filed: 08/17/1987
• Issued: 02/28/1989
• Est. Priority Date: 08/17/1987
• Status: Expired due to Fees

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Burt, Richard A., Hor, Ah-Mee, Kazmaier, Peter M., Loutfy, Rafik O.
• Primary Examiner(s): Goodrow, John L.
• Application Number:
  US07/086,333
• Time in Patent Office: 561 Days
• Field of Search: 430/59, 430/78, 430/73
• US Class Current: 430/58.8
• CPC Class Codes: C07D 471/22 in which the condensed systems contains four or more hetero rings
• CPC Class Codes: G03G 5/0651 containing four relevant rings
• CPC Class Codes: G03G 5/0655 containing six relevant rings
• CPC Class Codes: G03G 5/0659 containing more than seven relevant rings

Abstract

Disclosed is an improved layered photoresponsive imaging member comprised of a supporting substrate; an imidazole perinone comprised of components with a mixture of cis and trans isomers of Formulas III, IV, and V, including trans indanthrene Brilliant Orange, cis indanthrene Bordeaux Red; bis(4,5-dimethyl)benzimidazole perinone and bis 2,3 naphthimidazole perinone, and an aryl amine hole transport layer comprised of molecules of the following formula: ##STR1## dispersed in a resinous binder and wherein X is selected from the group consisting of halogen and alkyl.

Claims

1. An improved layered photoresponsive imaging member comprised of a supporting substrate;

a photogenerator layer comprised of a perinone as represented by the following formula ##STR8## wherein R is selected from the group consisting of hydrogen substituent, alkyl, aryl, substituted alkyl, and substituted aryl; and

an aryl amine hole transport layer comprised of molecules of the following formula;

##STR9## dispersed in a resinous binder and wherein X is selected from the group consisting of halogen and alkyl.

2. An imaging member in accordance with claim 1 wherein the supporting substrate is comprised of a conductive metallic substance, or an insulating polymeric composition overcoated with an electrically conductive layer.

3. An imaging member in accordance with claim 1 wherein the supporting substrate is aluminum.

4. An imaging member in accordance with claim 1 wherein the supporting substrate is overcoated with a polymeric adhesive layer.

5. An imaging member in accordance with claim 4 wherein the adhesive layer is a polyester resin.

6. An imaging member in accordance with claim 1 wherein X is selected from (ortho) CH₃, (meta) CH₃, (para) CH₃, (ortho) Cl, (meta) Cl, and (para) Cl.

7. An imaging member in accordance with claim 1 wherein the aryl amine is N,N'"'"'-diphenyl-N,N'"'"'-bis(3-methylphenyl)-[1,1'"'"'-biphenyl]-4,4'"'"'-diamine.

8. An imaging member in accordance with claim 1 wherein the resinous binder is a polycarbonate or polyvinylcarbazole.

9. An imaging member in accordance with claim 1 wherein the perinones are dispersed in a resinous binder in an amount of from about 5 percent to about 95 percent by volume, and the aryl amine hole transport molecules are dispersed in a resinous binder in an amount of from about 10 to about 75 percent by weight.

10. An imaging member in accordance with claim 9 wherein the resinous binder for the perinones is a polyester, polyvinylcarbazole, polyvinylbutyral, a polycarbonate, or a phenoxy resin;

and the resinous binder for the aryl amine hole transport material is a polycarbonate, a polyester, or a vinyl polymer.

11. A imaging member in accordance with claim 1 wherein the aryl amine hole transport layer is situated between the supporting substrate and the photogenerating layer.

21. A method of imaging which comprises forming an electrostatic latent image on the imaging member of claim 1, causing development thereof with toner particles;

subsequently transferring the developed image to a suitable substrate; and

permanently affixing the image thereto.

25. An imaging member in accordance with claim 1 wherein the perinone is comprised of a mixture of the cis and trans isomers of bis(4,5-dimethyl)benzimidazole perinone.

12. An improved layered photoresponsive imaging member which comprises a supporting substrate, a photogenerator layer comprising a perinone as represented by the following formula ##STR10## and an aryl amine hole transport layer comprising molecules of the following formula:

##STR11## dispersed in a resinous binder and wherein X is selected from the group consisting of halogen and alkyl.

13. An imaging member in accordance with claim 12 wherein the perinones are of the following formula ##STR12##

14. An imaging member in accordance with claim 12 wherein the perinones are of the following formula ##STR13##

15. An imaging member in accordance with claim 13 wherein the supporting conductive substrate is overcoated with a thin polymeric adhesive layer.

16. An imaging member in accordance with claim 15 wherein the aryl amine charge transporting layer comprises molecules of the formula:

##STR14## dispersed in a resinous binder, and wherein X is selected from the group consisting of halogen and alkyl.

17. An imaging member in accordance with claim 16 wherein X is selected from (ortho) CH₃, (meta) CH₃, (para) CH₃, (ortho) Cl, (meta) Cl, and (para) Cl.

18. An imaging member in accordance with claim 16 wherein the aryl amine is N,N'"'"'-diphenyl-N,N'"'"'-bis(3-methylphenyl)-[1,1'"'"'-biphenyl]-4,4'"'"'-diamine.

19. An imaging member in accordance withh claim 16 wherein the resinous binder is a polycarbonate or polyvinyl carbazole.

20. An imaging member in accordance with claim 16 wherein the perinones are dispersed in a resinous binder in an amount of from about 5 percent to about 95 percent by volume, and the aryl amine hole transport molecules are dispersed in a resinous binder in an amount of from about 10 to about 75 percent by weight.

22. A method of imaging which comprises forming an electrostatic latent image on the imaging member of claim 12, causing development thereof with toner particles, subsequently transferring the developed image to a suitable substrate;

and permanently affixing the image thereto.

23. A method of imaging which comprises forming an electrostatic latent image on the imaging member of claim 13, causing development thereof with toner particles;

subsequently transferring the developed image to a suitable substrate; and

permanently affixing the image thereto.

24. A method of imaging which comprises forming an electrostatic latent image on the imaging member of claim 14, causing development thereof with toner particles;

subsequently transferring the developed image to a suitable substrate; and

permanently affixing the image thereto.

26. An imaging member in accordance with claim 12 wherein the perinone is trans indanthrene Brilliant Orange.

27. An imaging member in accordance with claim 12 wherein the perinone is cis indanthrene Bordeaux RR.

28. An imaging member in accordance with claim 12 wherein the perinone is comprised of a mixture of trans indanthrene Brilliant Orange and indanthrene Bordeaux RR.

29. An imaging member in accordance with claim 12 wherein the perinones are of the following formula ##STR15##

30. An imaging member in accordance with claim 12 wherein the perinone is comprised of a mixture of cis and trans isomers of Formula I.