IP Library Granted Patent US 7,153,980
Granted Patent B2
US 7,153,980 · App. 10/783,674 · Granted Dec 26, 2006

Thiophene-containing compound and thiophene-containing compound polymer

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Quick Facts
Patent No.
US 7,153,980
App. No.
10/783,674
Granted
Dec 26, 2006
Kind
B2
Abstract

The present invention relates to a thiophene-containing compound and a thiophene-containing compound polymer which are useful for organo-electronic devices such as electrophotographic photoreceptors (photosensitive elements), organic electroluminescent elements and organic transistors. More specifically, the invention relates to a thiophene-containing compound and a thiophene-containing compound polymer which are excellent in terms of both charge-transporting properties and luminous properties.

Claims (24)

1. A thiophene-containing compound represented by the following formula (I):

wherein, in formula (I), Ar represents one or more thiophene rings, a monovalent aromatic group containing one or more thiophene rings or a monovalent aromatic group; X represents one or more thiophene rings, a monovalent or divalent aromatic group containing one or more thiophene rings or a monovalent or divalent aromatic group, in which all of the thiophene rings and aromatic groups may be unsubstituted or further may have a substituent; R 1 represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group; n indicates an integer of from 0 to 5; and k indicates 0 or 1; provided that at least one of Ar and X contains a thiophene ring.

2. The thiophene-containing compound according to claim 1 , wherein X in formula (I) represents a group represented by any one selected from the group consisting of the following formulae (II-1) to (II-4):

wherein, in formulae (II-1) to (II-4), R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group or a halogen atom; c and d each indicate an integer of from 0 to 5; and V represents a group represented by any one selected from the group consisting of the following formulae (III-1) to (III-11):

wherein, in formulae (III-1) to (III-11), e indicates an integer of from 1 to 5; and f and g each indicate an integer of from 0 to 5.

3. The thiophene-containing compound according to claim 1 , wherein X in formula (I) represents a group represented by any one selected from the group consisting of the following formulae (IV-1) to (IV-4):

wherein, in formulae (II-1) to (II-4), a indicates an integer of from 0 to 10; and b indicates an integer of from 1 to 10.

4. The thiophene-containing compound according to claim 1 , wherein the one or more thiophene rings represented by Ar are selected from the group consisting of a thienyl group, bithienyl group and terthienyl group.

5. The thiophene-containing compound according to claim 1 , wherein the monovalent aromatic group represented by Ar is a monovalent aromatic group having 1 to 10 aromatic rings.

6. The thiophene-containing compound according to claim 1 , wherein R 1 in formula (I) is selected from the group consisting of a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group and a substituted or unsubstituted aralkyl group.

7. The thiophene-containing compound according to claim 6 , wherein the alkyl group represented by R 1 is selected from the group consisting of a methyl group, an ethyl group, a propyl group and an isopropyl group.

8. The thiophene-containing compound according to claim 6 , wherein the substituted or unsubstituted aryl group represented by R 1 is a phenyl group or a tolyl group.

9. The thiophene-containing compound according to claim 6 , wherein the substituted or unsubstituted aralkyl group represented by R 1 is a benzyl group or a phenethyl group.

10. A thiophene-containing compound polymer represented by the following formula (V-1) or (V-2):

wherein, in formulae (V-1) and (V-2), Y represents a divalent hydrocarbon group; Z represents a divalent hydrocarbon group; B and B′ each independently represent —O—(Y—O) m —H or —O—(Y—O) m —CO-Z-CO—OR 2 , in which R 2 represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted aralkyl group; m indicates an integer of from 1 to 5, and p indicates an integer of from 5 to 5,000; and A represents a group represented by the following formula (VI):

wherein, in formula (VI), Ar represents one or more thiophene rings, a monovalent aromatic group containing one or more thiophene rings or a substituted or unsubstituted monovalent aromatic group; X represents one or more thiophene rings, a divalent aromatic group containing one or more thiophene rings or a divalent aromatic group, in which all of the thiophene rings and aromatic groups may be unsubstituted or further may have a substituent; and n indicates an integer of from 0 to 5; provided that at least one of Ar and X contains a thiophene ring.

11. The thiophene-containing compound polymer according to claim 10 , wherein X in formula (VI) represents a group represented by any one selected from the group consisting of the following formulae (II-1) to (II-4):

wherein, in formulae (II-1) to (II-4), R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group or a halogen atom; c and d each indicate an integer of from 0 to 5; and V represents a group represented by any one selected from the group consisting of the following formulae (III-1) to (III-11):

wherein, in formulae (III-1) to (III-11), e indicates an integer of from 1 to 5; and f and g each indicate an integer of from 0 to 5.

12. The thiophene-containing compound polymer according to claim 10 , wherein X in formula (VI) represents a group represented by any one selected from the group consisting of the following formulae (IV-1) to (IV-4):

wherein, in formulae (II-1) to (II-4), a indicates an integer of from 0 to 10; and b indicates an integer of from 1 to 10.

13. The thiophene-containing compound polymer according to claim 10 , having a polymerization degree ranging from 5 to 5,000.

14. The thiophene-containing compound polymer according to claim 13 , having a polymerization degree ranging from 10 to 1,000.

15. The thiophene-containing compound polymer according to claim 10 , having a weight average molecular weight Mw ranging from 10,000 to 300,000.

Assignments (3)
CHANGE OF NAME Recorded Aug 12, 2021
From: FUJI XEROX CO., LTD.
To: FUJIFILM BUSINESS INNOVATION CORP.
Reel/Frame 058287/0056 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED ON REEL 015351 FRAME 0859. Recorded Dec 6, 2004
From: OHBA, YOSHIHIRO; SATO, KAZUAKI; SEKI, MIEKO; AGATA, TAKESHI; SATO, KATSUHIRO; MASHIMO, KIYOKAZU; YONEYAMA, HIROHITO; HIROSE, HIDEKAZU
To: FUJI XEROX CO., LTD.
Reel/Frame 016046/0331 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2004
From: OHBA, YOSHIHIRO; SATO, KAZUAKI; SEKI, MIEKO; AGATA, TAKESHI; SATO, KATSUHIRO; MASHIMO, KIYOKAZU; YONEYAMA, HIROHITO; HIROSE, HIDEKAZU
To: FUJI XEROX CO., LTD.
Reel/Frame 015351/0859 →