Carbonyl-functionalized thiophene compounds and related device structures

• US 20060186401A1
• Filed: 09/14/2005
• Published: 08/24/2006
• Est. Priority Date: 09/14/2004
• Status: Active Grant

• Current Assignee: Northwestern University
• Original Assignee: Northwestern University
• Inventors: Marks, Tobin J., Facchetti, Antonio
• Granted Patent: US 7,528,176 B2
• Time in Patent Office: Days
• US Class Current: 257/40
• CPC Class Codes: C07D 333/22 Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 10/486 the channel region comprising two or more active layers, e.g. forming pn heterojunctions
• CPC Class Codes: H10K 71/40 Thermal treatment, e.g. annealing in the presence of a solvent vapour
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/655 comprising only sulfur as heteroatom

Abstract

Carbonyl-functionalized oligo/polythiophene compounds, and related semiconductor components and related device structures.

Claims

1. A semiconductor compound of a formula

2. The compound of claim 1 wherein each said x and z are 0, and y is an integer ranging from about 4 to about 8.

3. The compound of claim 1 wherein R¹ is selected from alkyl, perfluoroalkyl, phenyl and perfluorophenyl moieties.

4. The compound of claim 3 wherein each said x and z are 0, and y is an integer ranging from about 4 to about 8.

5. The compound of claim 4 selected from

6. The compound of claim 1 incorporated into a semiconductor component of an electronic device.

7. The compound of claim 6 wherein said component comprises a composition comprising at least one of said compounds and a polymer enhancing solubility of said compound in a solvent.

8. The compound of claim 4 selected from

25. An organic field effect transistor device comprising a semiconductor component comprising a compound selected from compounds of claims 1, 9 and 16 and combinations of said compounds.

26. A device of claim 25 wherein said semiconductor component comprises at least one compound exhibiting hole and electron mobilities under device operation conditions.

27. The device of claim 25 wherein said semiconductor component is fabricated with a composition comprising at least one of said compounds and a polymer enhancing solvent solubility of said compounds.

28. The device of claim 25 comprising a semiconductor component comprising at least one said compound exhibiting hole mobility and at least one said compound exhibiting electron mobility, under device operation conditions.

9. A semiconductor compound of a formula

10. The compound of claim 9 wherein R¹ is selected from alkyl, and fluorosubstituted alkyl, phenyl and fluorosubstituted phenyl moieties.

11. The compound of claim 10 wherein each said x is 1, y is 1, z and y′

are 0, each said w is 1 and each said v is 1.

12. The compound of claim 11 wherein R′

is selected from alkyl and perfluoroalkyl.

13. The compound of claim 12 wherein R′

is selected from hexyl and perfluorohexyl.

14. The compound of claim 9 wherein R¹ is fluorosubstituted phenyl, said compound of a formula

15. The compounds of claim 14 wherein R′

is F.

16. A semiconductor compound of the formula

17. The compound of claim 16 wherein R¹ is selected from H, alkyl, perfluoroalkyl, phenyl and perfluorophenyl;

each said w is 1;

each said x is selected from 2 to about 4; and

y, y′

, z and a are 0.

18. The compound of claim 17 wherein R¹ is selected from phenyl and perfluorophenyl.

19. The compound of claim 18 blended with a polymer enhancing the solvent solubility of said compound.

20. The compound of claim 19 wherein said blended composition is incorporated into the semiconductor component of an electronic device.

21. The compound of claim 16 wherein R¹ is selected from H, alkyl, perfluoroalkyl, phenyl and perfluorophenyl;

each said w is 1;

each said x is selected from 2 to about 4;

y′

, z and a are 0;

each said Ar is selected from phenyl, diacylphenyl, fluorosubstituted phenyl and diacylperfluorophenyl; and

y is 1.

22. The compound of claim 21 wherein each said w is 0, R¹ is H and each said x is 2.

23. The compound of claim 22 selected from compounds wherein Ar is diacylperfluorophenyl and polymers of said compound.

24. The compound of claim 21 wherein Ar is perfluorophenyl.