Multi-active electrophotographic element and imaging process using free radicals as charge transport material

• US 5,324,604 A
• Filed: 06/17/1991
• Issued: 06/28/1994
• Est. Priority Date: 06/17/1991
• Status: Expired due to Fees

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Kung, Teh-Ming, Young, Ralph H., Bugner, Douglas E.
• Primary Examiner(s): McCamish, Marion E.
• Assistant Examiner(s): Ashton, Rosemary
• Application Number:
  US07/716,197
• Time in Patent Office: 1,107 Days
• Field of Search: 430/54, 430/58, 430/70, 430/71, 430/72
• US Class Current: 430/58.05
• CPC Class Codes: G03G 5/047 characterised by the charge-generation layers or charge transport layers G03G5/0433 and G03G5/0436 take precedence
• CPC Class Codes: G03G 5/06 characterised by the photoconductive material being organic

Abstract

The present invention relates to a multi-active electrophotographic element having a charge-transport layer containing stable free radical compounds as the charge-transport material. A process of forming images with this element is also disclosed.

Claims

1. A multi-active electrophotographic element comprising:

a charge-generation layer;

a charge-transport layer contiguous with said charge-generation layer, wherein said charge-transport layer comprises;

a stable free radical compound defined by the formula;

##STR3## wherein;

°

C. is a carbon atom with an unpaired electron and

R¹, R², and R³ are the same or different and each represent a hydrogen, alkyl, aryl, aralkyl, arylene, alkylene, heterocyclic arylene, imino or halogen group;

or a substituted alkyl, aryl, aralkyl, arylene, alkylene, heterocyclic arylene or imino group;

or an alkyl, aryl, aralkyl, arylene, alkylene or heterocyclic arylene group linking two or more °

C. atoms;

or are themselves linked; and

a conductive support in electrical contact with either said charge-generation layer or said charge-transport layer.

2. The element of claim 1, wherein said stable free radical compound is chosen from the group consisting of α

,γ

-bisdiphenylene-β

-phenylallyl, α

,γ

-bisdiphenylene-β

-(p-isopropylphenyl)allyl, α

,γ

-bisdiphenylene-β

-(p-isopropenylphenyl)allyl, perchlorodiphenylmethyl, triphenylmethyl, diphenylbiphenylmethyl, phenylbis(biphenyl)methyl, alkyl and alkoxy substituted triphenylmethyls, 4,4'"'"'-polymethylenebis(triphenylmethyl)s, pentaphenylcyclopentadienyl, perchlorophenylmethyl, (o-ethoxyphenyl)diphenylmethyl, 9-phenylfluorenyl, diphenyl-β

-naphthylmethyl, α

-methoxydiphenylmethyl, dimesitylmethYl, p,p'"'"'-triphenylenebis(diphenylmethyl), α

-naphthylbis(biphenyl)methyl, pentaphenylethyl, bis(2,5-di-tert-butylphenyl)methyl, dibenzofulvenylmethyl, 4-(perchlorophenyl)diphenylmethyl, 4,4'"'"'-bis(perchlorophenyl)diphenylmethyl, perchlorotriphenylmethyl, 4-(perchlorophenyl)triphenylmethyl, 4,4'"'"'-bis(perchlorophenyl)triphenylmethyl, 4,4'"'"',4"-tris(perchlorophenyl)triphenylmethyl, 4,4'"'"'-bis(diphenylmethyl)biphenyl, and tris(4-E-tetrachlorophenyl)methyl wherein E represents an electron-withdrawing group such as halo, nitro, alkoxycarbonyl, trihalomethyl, cyano, keto, or sulfonyl.

3. The element of claim 2, wherein said stable free radical compound is chosen from the group consisting of α

,γ

-bisdiphenylene-β

-phenylallyl, 4,4'"'"'-bis(diphenylmethyl)biphenyl, and tris (4-E-tetrachlorophenyl)methyl wherein E represents an electron-withdrawing group such as halo, nitro, alkoxycarbonyl, trihalomethyl, cyano, keto, or sulfonyl.

4. The element of claim 1, wherein said charge-generation layer is contiguous to both said charge-transport layer and said conductive support.

5. The element of claim 1, wherein said charge-transport layer is contiguous to both said charge-generation layer and said conductive support.

6. The element of claim 1 further comprising:

a polymeric binder.

7. The element of claim 6, wherein said binder is selected from the group consisting of polycarbonates, polyesters, polyolefins, styrenic polymers, phenolic resins, paraffins, and mineral waxes.

8. The element of claim 7, wherein said binder is chosen from the group consisting of bisphenol-A polycarbonate polymers, copolymers of vinyl benzoates and vinyl acetate, and 5 poly[4,4'"'"'-(2-norbornylidene)bisphenyleneazelate-co-terephthalate)].

9. The element of claim 1 further comprising:

an adhesive interlayer.

10. The element of claim 1, wherein said element is suitable for either neg-pos imaging or pos-pos imaging.

11. A multi-active electrophotographic element comprising:

a charge-generation layer;

a charge-transport layer contiguous with said charge-generation layer, wherein said charge-transport layer comprises;

a polymeric binder;

a stable free radical compound chosen from the group consisting of

α

,γ

-bisdiphenylene-β

-phenylallyl,

α

,γ

-bis(diphenylmethyl) biphenyl, and tris(4-E-tetrachlorophenyl)methyl wherein E represents an electron-withdrawing group such as halo, nitro, alkoxycarbonyl, trihalomethyl, cyano, keto, or sulfonyl; and

a conductive support in electrical contact with said charge-generation layer.

12. An electrophotographic process using a multi-active electrophotographic element comprising:

a charge-generation layer;

a charge-transport layer contiguous with said charge-generation layer, wherein said charge-transport layer comprises;

a stable free radical compound defined by the formula;

##STR4## wherein;

°

C. is a carbon atom with an unpaired electron and

R¹, R², and R³ are the same or different and each represent a hydrogen, alkyl, aryl, aralkyl, arylene, alkylene, heterocyclic arylene, imino or halogen group;

or a substituted alkyl, aryl, aralkyl, arylene, alkylene, heterocyclic arylene or imino group;

or an alkyl, aryl, aralkyl, arylene, alkylene or heterocyclic arylene group linking two or more °

C. atoms;

or are themselves linked; and

a conductive support in electrical contact with either said charge-generation layer or said charge-transport layer,

said process comprising;

charging said element;

exposing said charged element to activating radiation; and

developing the charged and exposed element by applying charged toner particles to said element to produce a toned image.

13. A process according to claim 12, wherein the stable free radical compound is chosen from the group consisting of α

,γ

-bisdiphenylene-β

-phenylallyl, α

,γ

-bisdiphenylene-β

-(p-isopropylphenyl)allyl, α

,γ

-bisdiphenylene-β

-(p-isopropenyIphenyI)allyl, perchlorodiphenylmethyl, triphenylmethyl, diphenylbiphenylmethyl, phenylbis(biphenyl)methyl, alkyl and alkoxy substituted triphenylmethyls, 4,4'"'"'-polymethylenebis(triphenylmethyl)s, pentaphenylcyclopentadienyl, perchlorophenylmethyl, (o-ethoxyphenyl)diphenylmethyl, 9-phenylfluorenyl, diphenyl-β

-naphthylmethyl, α

-methoxydiphenylmethyl, dimesitylmethyl, p,p'"'"'-triphenylenebis(diphenylmethyl), α

-naphthylbis(biphenyl)methyl, pentaphenylethYl, bis(2,5-di-tert-butylphenyl)methyl, dibenzofulvenylmethyl, 4-(perchlorophenyl)diphenylmethyl, 4,4'"'"'-bis(perchlorophenyl)diphenylmethyl, perchlorotriphenylmethyl, 4-(perchlorophenyl)triphenylmethyl, 4,4'"'"'-bis(perchlorophenyl)triphenylmethyl, 4,4'"'"',4"-tris(perchlorophenyl)triphenylmethyl, 4,4'"'"'-bis(diphenylmethyl)biphenyl, and tris(4-E-tetrachlorophenyl)methyl wherein E represents an electron-withdrawing group such as halo, nitro, alkoxycarbonyl, trihalomethyl, cyano, keto, or sulfonyl.

14. A process according to claim 13, wherein the stable free radical compound is chosen from the group consisting of α

,γ

-bisdiphenylene-β

-phenylallyl, 4,4'"'"'-bis(diphenylmethyl)biphenyl, and tris (4-E-tetrachlorophenyl)methyl, wherein E represents an electron-withdrawing group such as halo, nitro, alkoxycarbonyl, trihalomethyl, cyano, keto, or sulfonyl.

15. A process according to claim 12, wherein said element and said toner particles are charged to perform pos-pos imaging.

16. A process according to claim 12, wherein said element and said toner particles are charged to perform neg-pos imaging.

17. A process according to claim 12 further comprising:

transferring the toned image to a suitable receiver.

18. A process according to claim 17 further comprising:

bonding said toned image to said receiver.

19. A process according to claim 17 further comprising:

cleaning any residual toner particles not transferred to the receiver from said element for each print made.

20. A process according to claim 17, wherein the receiver is a substrate suitable for Permanently receiving a toned image as a print.

21. A process according to claim 17 wherein said receiver is suitable for overhead projection.