Organosilicon-modified charge transporting compound and curable composition containing the compound and having charge transporting ability

• US 6,376,695 B1
• Filed: 11/05/1996
• Issued: 04/23/2002
• Est. Priority Date: 11/06/1995
• Status: Expired due to Term

• Current Assignee: Canon Kabushiki Kaisha (Canon Inc.)
• Original Assignee: Canon Kabushiki Kaisha (Canon Inc.), Dow Corning Toray Company Limited (Dow, Inc.), Dow, Inc.
• Inventors: Masatomi, Toru, Nishida, Shunichiro, Takeuchi, Kikuko, Yoshinaga, Kazuo, Kobayashi, Hideki, Kushibiki, Nobuo, Hashimoto, Yuichi
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/744,192
• Time in Patent Office: 1,995 Days
• Field of Search: 556/413, 528/17, 528/33, 528/38
• US Class Current: 556/413
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C08G 77/18 to alkoxy or aryloxy groups
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/70 Siloxanes defined by use of the MDTQ nomenclature
• CPC Class Codes: C08K 9/06 with silicon-containing compounds
• CPC Class Codes: C08L 2666/44 Silicon-containing compounds
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G03G 5/0578 Polycondensates comprising silicon atoms in the main chain
• CPC Class Codes: G03G 5/06142 arylamine
• CPC Class Codes: G03G 5/06144 diamine
• CPC Class Codes: G03G 5/061443 benzidine
• CPC Class Codes: G03G 5/06147 alkenylarylamine
• CPC Class Codes: G03G 5/061473 plural alkenyl groups linked directly to the same aryl group
• CPC Class Codes: G03G 5/0616 Hydrazines; Hydrazones
• CPC Class Codes: G03G 5/0629 containing one hetero atom
• CPC Class Codes: G03G 5/0631 containing two hetero atoms
• CPC Class Codes: G03G 5/0633 containing three hetero atoms
• CPC Class Codes: G03G 5/0637 containing one hetero atom
• CPC Class Codes: G03G 5/0642 being more than six-membered
• CPC Class Codes: G03G 5/078 comprising silicon atoms

Abstract

An organosilicon-modified charge transporting compound having a structure represented by the following Formula (I):

wherein A represents a charge transporting group, Q represents a hydrolytic group or a hydroxyl group, R² represents a monovalent hydrocarbon group or a halogen-substituted monovalent hydrocarbon group having 1 to 15 carbon atoms, n is 1 to 18, m is 1 to 3, and 1 is 1 to 5; and a curable composition containing the organosilicon-modified charge transporting compound and a cure type resin chiefly composed of an organosilicon high polymer.

Claims

1. An organosilicon-modified charge transporting compound having a structure represented by the following

Q represents a hydrolytic group or a hydroxyl group, R² represents a monovalent hydrocarbon group or a halogen-substituted monovalent hydrocarbon group having 1 to 15 carbon atoms, n is 1 to 18, m is 1 to 3, P is 1 to 5, R³, R⁴ and R⁵ each represent an organic group, at least one of which represents an aromatic hydrocarbon ring group or a heterocyclic group and R³, R⁴ and R⁵ are the same or different.

2. The organosilicon-modified charge transporting compound according to claim 1, wherein said hydrolytic group is a group represented by —

OR¹, where R¹ represents an alkyl or alkoxyalkyl group having 1 to 6 carbon atoms.

3. The organosilicon-modified charge transporting compound according to claim 1, which has an ionization potential of from 4.5 eV to 6.2 eV.

4. The organosilicon-modified charge transporting compound according to claim 1, wherein said charge transporting group has a structure represented by the following Formula (II).

wherein R³, R⁴ and R⁵ each represent an organic group, at least one of which represents an aromatic hydrocarbon ring group or a heterocyclic group, and R³, R⁴ and R⁵ may be the same or different.

5. A curable composition having a charge transporting ability, which comprises;

a cure type resin chiefly composed of an organosilicon high polymer in which monovalent hydrocarbon groups bonded to silicon atoms and the silicon atoms are in a ratio of from 0.5 to 1.5; and

an organosilicon-modified charge transporting compound having a structure represented by the following

Q represents a hydrolytic group or a hydroxyl group, R² represents a monovalent hydrocarbon group or a halogen-substituted monovalent hydrocarbon group having 1 to 15 carbon atoms, n is 1 to 18, m is 1 to 3, l is 1 to 5, R³, R⁴ and R⁵ each represent an group, at least one of which represents an aromatic hydrocarbon ring group or a heterocyclic group and R³, R⁴ and R⁵ are the same or different.

6. The curable composition according to claim 5, wherein said hydrolytic group is a group represented by —

OR¹, where R¹ represents an alkyl or alkoxyalkyl group having 1 to 6 carbon atoms.

7. The curable composition according to claim 5, wherein said organosilicon high polymer is an organopolysiloxane having a structural unit represented by the following Formula (III):

8. The curable composition according to claim 5, wherein said organosilicon-modified charge transporting compound is contained in an amount of from 20 parts by weight to 200 parts by weight based on 100 parts by weight of the organosilicon high polymer of the cure type resin.

9. The curable composition according to claim 5, wherein said charge transporting group has a structure represented by the following Formula (II):

wherein R³, R⁴ and R⁵ each represent an organic group, at least one of which represents an aromatic hydrocarbon ring group or a heterocyclic group, and R³, R⁴ and R⁵ may be the same or different.

10. The curable composition according to claim 5, wherein said cure type resin contains a silane compound represented by the following Formula (IV):