IP Library Granted Patent US 7,589,166
Granted Patent B2
US 7,589,166 · App. 11/404,991 · Granted Sep 15, 2009

Thiophene-containing compound and polymer thereof

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Quick Facts
Patent No.
US 7,589,166
App. No.
11/404,991
Granted
Sep 15, 2009
Kind
B2
Abstract

The present invention provides a thiophene-containing compound represented by Formula (I) and a thiophene-containing compound polymer using the thiophene-containing compound. In Formula (I), Ar 1 represents a substituted or unsubstituted monovalent aromatic group; X represents a divalent straight-chain hydrocarbon group having 1 to 6 carbon atoms, a divalent branched-chain hydrocarbon group having 2 to 10 carbon atoms, or a substituted or unsubstituted divalent aromatic group; R 1 to R 5 each independently represent a hydrogen atom, an alkyl group, a cyano group, a halogen group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; 1 represents an integer from 1 to 5; and m and k each independently represent 0 or 1.

Claims (23)

1. A thiophene-containing compound represented by Formula (I):

wherein in Formula (I), Ar 1 represents a substituted or unsubstituted monovalent aromatic group; X represents a divalent straight-chain hydrocarbon group having 1 to 6 carbon atoms, a divalent branched-chain hydrocarbon group having 2 to 10 carbon atoms, or a substituted or unsubstituted divalent aromatic group; R 1 to R 5 each independently represent a hydrogen atom, an alkyl group, a cyano group, a halogen group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; 1 represents an integer from 1 to 5; and m and k each independently represent 0 or 1.

2. The thiophene-containing compound of claim 1 , wherein in Formula (I), X represents a divalent straight-chain hydrocarbon group having 2 to 6 carbon atoms, a divalent branched-chain hydrocarbon group having 3 to 7 carbon atoms, a substituted or unsubstituted divalent polynuclear aromatic hydrocarbon having 1 to 8 aromatic rings, a substituted or unsubstituted divalent condensed aromatic hydrocarbon having 1 to 8 aromatic rings, or a substituted or unsubstituted divalent aromatic heterocyclic ring having 1 to 11 heterocyclic rings.

3. The thiophene-containing compound of claim 1 , wherein in Formula (I), X represents a group represented by one selected from the group consisting of Structural Formulae (II-1) to (II-5):

wherein in Structural Formula (II-1), R 6 represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; and in Structural Formula (II-5), k′ represents an integer from 1 to 5.

4. The thiophene-containing compound of claim 1 , wherein in Formula (I), Ar 1 represents a substituted or unsubstituted phenyl group.

5. The thiophene-containing compound of claim 1 , wherein in Formula (I), Ar 1 represents a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 20 aromatic rings.

6. The thiophene-containing compound of claim 1 , wherein in Formula (I), Ar 1 represents a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 20 aromatic rings.

7. The thiophene-containing compound of claim 1 , wherein in Formula (I), Ar 1 represents a substituted or unsubstituted monovalent aromatic heterocyclic ring.

8. The thiophene-containing compound of claim 1 , wherein in Formula (I), Ar 1 represents a substituted or unsubstituted monovalent aromatic group containing at least one aromatic heterocyclic ring.

9. A thiophene-containing compound polymer represented by Formula (III-1) or (III-2):

wherein in Formulae (III-1) and (III-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 7 ; R 7 represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group; m′ represents an integer from 1 to 5; p represents an integer from 5 to 5,000; and A represents a group represented by Formula (IV),

wherein in Formula (IV), Ar 1 represents a substituted or unsubstituted monovalent aromatic group; X represents a divalent straight-chain hydrocarbon group having 1 to 6 carbon atoms, a divalent branched-chain hydrocarbon group having 2 to 10 carbon atoms, or a substituted or unsubstituted divalent aromatic group; R 1 to R 4 each independently represent a hydrogen atom, an alkyl group, a cyano group, a halogen group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; 1 represents an integer from 1 to 5; and m and k each independently represent 0 or 1.

10. The thiophene-containing compound polymer of claim 9 , wherein in Formula (IV), X represents a divalent straight-chain hydrocarbon group having 2 to 6 carbon atoms, a divalent branched-chain hydrocarbon group having 3 to 7 carbon atoms, a substituted or unsubstituted divalent polynuclear aromatic hydrocarbon having 1 to 8 aromatic rings, a substituted or unsubstituted divalent condensed aromatic hydrocarbon having 1 to 8 aromatic rings, or a substituted or unsubstituted divalent aromatic heterocyclic ring having 1 to 11 heterocyclic rings.

11. The thiophene-containing compound polymer of claim 9 , wherein in Formula (IV), X represents a group represented by one selected from the group consisting of Structural Formulae (II-1) to (II-5):

wherein in Structural Formula (II-1), R 6 represents a hydrogen atom, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aralkyl group; and in Structural Formula (II-5), k′ represents an integer from 1 to 5.

12. The thiophene-containing compound polymer of claim 9 , wherein in Formula (IV), Ar 1 represents a substituted or unsubstituted phenyl group.

13. The thiophene-containing compound polymer of claim 9 , wherein in Formula (IV), Ar 1 represents a substituted or unsubstituted monovalent polynuclear aromatic hydrocarbon having 2 to 20 aromatic rings.

14. The thiophene-containing compound polymer of claim 9 , wherein in Formula (IV), Ar 1 represents a substituted or unsubstituted monovalent condensed aromatic hydrocarbon having 2 to 20 aromatic rings.

15. The thiophene-containing compound polymer of claim 9 , wherein in Formula (IV), Ar 1 represents a substituted or unsubstituted monovalent aromatic heterocyclic ring.

16. The thiophene-containing compound polymer of claim 9 , wherein in Formula (IV), Ar 1 represents a substituted or unsubstituted monovalent aromatic group containing at least one aromatic heterocyclic ring.

17. The thiophene-containing compound polymer of claim 9 , wherein in Formulae (III-1) and (III-2), p represents an integer from 10 to 1,000.

18. The thiophene-containing compound polymer of claim 9 , wherein a weight-average molecular weight Mw of the polymer is in a range of 10,000 to 300,000.

Assignments (2)
CHANGE OF NAME Recorded Aug 12, 2021
From: FUJI XEROX CO., LTD.
To: FUJIFILM BUSINESS INNOVATION CORP.
Reel/Frame 058287/0056 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2006
From: OHBA, YOSHIHIRO; SATO, KAZUAKI; NISHINO, YOHEI; SEKI, MIEKO; AGATA, TAKESHI; MASHIMO, KIYOKAZU; SATO, KATSUHIRO; YONEYAMA, HIROHITO; OKUDA, DAISUKE; HIROSE, HIDEKAZU; ISHII, TORU
To: FUJI XEROX CO., LTD.
Reel/Frame 017796/0506 →