Phenolic hole transport polymers

• US 20070087276A1
• Filed: 10/13/2005
• Published: 04/19/2007
• Est. Priority Date: 10/13/2005
• Status: Active Grant

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Vong, Cuong, Hu, Nan-Xing, Qi, Yu, McGuire, Greg
• Granted Patent: US 7,538,175 B2
• Time in Patent Office: Days
• US Class Current: 430/58.700
• CPC Class Codes: C08G 8/24 with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
• CPC Class Codes: G03G 5/0567 Other polycondensates comprising oxygen atoms in the main chain; Phenol resins
• CPC Class Codes: G03G 5/0589 Macromolecular compounds characterised by specific side-chain substituents or end groups
• CPC Class Codes: G03G 5/0616 Hydrazines; Hydrazones
• 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 5/14708 comprising organic material
• CPC Class Codes: G03G 5/14713 Macromolecular material
• CPC Class Codes: G03G 5/1476 Other polycondensates comprising oxygen atoms in the main chain; Phenol resins
• CPC Class Codes: G03G 5/14786 Macromolecular compounds characterised by specific side-chain substituents or end groups
• CPC Class Codes: G03G 9/0819 characterised by the dimensions of the particles

Abstract

A polymer having hole transport functionality and antioxidant properties is disclosed. The polymer comprises a phenolic segment and a hole transport segment. The polymer is suitable for use in the charge transport layer of an imaging member. Processes for producing the polymer are also disclosed.

Claims

1. A phenolic hole transport polymer, comprising a phenolic segment (A), a hole transport segment (B), and a divalent linkage (D):

QAQ QFQ-D-

wherein Q indicates a link site from a segment A or B to a divalent linkage D; and

wherein D is alkylene containing from 1 to 15 carbon atoms and optionally containing a heteroatom selected from the group consisting of oxygen, sulfur, silicone, and nitrogen.

2. The phenolic hole transport polymer of claim 1, wherein A is represented by formula (I):

3. The phenolic hole transport polymer of claim 1, wherein said B is represented by the following general formula (II)

4. The phenolic hole transport polymer of claim 1, wherein the phenolic segment (A) comprises from about 10 to about 80 wt-% of the polymer.

5. The phenolic hole transport polymer of claim 4, wherein the phenolic segment (A) comprises from about 15 to about 50 wt-% of the polymer.

6. The phenolic hole transport polymer of claim 1, wherein the polymer is represented by Formula (III):

7. The phenolic hole transport polymer of claim 6, wherein said polymer has an average molecular weight ranging from about 1,000 to about 100,000.

8. The phenolic hole transport polymer of claim 6, wherein D is methylene and Ar is 3,4-dimethylphenyl or biphenyl.

9. The phenolic hole transport polymer of claim 8, wherein D is methylene, R₂ and R₄ are hydrogen, R₃ is methyl or ethoxyl, and Ar is 3,4-dimethylphenyl.

10. The phenolic hole transport polymer of claim 6, wherein the hole transport polymer is selected from the group consisting of formulas (III-a) to (III-k):

11. The phenolic hole transport polymer of claim 6, wherein the hole transport polymer is selected from the group consisting of Formulas (III-m) and (III-p):

12. The imaging member of claim 1, wherein the phenolic segment and the hole transport segment are present in a molar ratio of from 1:

9 to 9;

1.

13. An imaging member having a layer comprising a phenolic hole transport polymer, the polymer comprising a phenolic segment (A), a hole transport segment (B), and a divalent linkage (D):

QAQ QBQ-D-

wherein Q indicates a link site from a segment A or B to a divalent linkage D; and

wherein D is alkylene containing from 1 to 15 carbon atoms and optionally containing a heteroatom selected from the group consisting of oxygen, sulfur, silicone, and nitrogen.

14. The imaging member of claim 13, wherein A is represented by formula (I):

15. The imaging member of claim 13, wherein said B is represented by the following general formula (II)

16. The imaging member of claim 13, wherein the polymer is represented by Formula (III):

17. The imaging member of claim 13, wherein said polymer has an average molecular weight ranging from about 1,000 to about 100,000.

18. The imaging member of claim 13, wherein the layer is a charge transport layer or an overcoat layer.

19. The imaging member of claim 13, wherein the phenolic hole transport polymer is crosslinked.

20. A method of imaging, comprising:

generating an electrostatic latent image on an imaging member;

developing the latent image; and

transferring the developed electrostatic image to a suitable substrate;

wherein the imaging member has a layer comprising a phenolic hole transport polymer, the polymer comprising a phenolic segment (A), a hole transport segment (B), and a divalent linkage (D);

QAQ QBQ-D-

wherein Q indicates a link site from a segment A or B to a divalent linkage D; and

wherein D is alkylene containing from 1 to 15 carbon atoms and optionally containing a heteroatom selected from the group consisting of oxygen, sulfur, silicone, and nitrogen.