Semiconductors containing perfluoroether acyl oligothiophene compounds

• US 7,151,276 B2
• Filed: 03/09/2005
• Issued: 12/19/2006
• Est. Priority Date: 03/09/2005
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Vogel, Dennis E., Ender, David A., Gerlach, Christopher P.
• Primary Examiner(s): Baumeister, B. William
• Assistant Examiner(s): Such, Matthew W.
• Application Number:
  US11/075,978
• Publication Number:
  US 20060202191A1
• Time in Patent Office: 650 Days
• Field of Search: 257/40, 438/99, 438/82, 438/103, 438/30
• US Class Current: 257/40
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 10/474 the gate dielectric comprising a multilayered structure
• 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

Semiconductor devices are described that include a semiconductor layer that comprises a perfluoroether acyl oligothiophene compound, preferably an α,ω-bis-perfluoroether acyl oligothiophene compound. Additionally, methods of making semiconductor devices are described that include depositing a semiconductor layer that contains a perfluoroether acyl oligothiophene compound, preferably an α,ω-bis(2-perfluoroether acyl oligothiophene compound.

Claims

1. A semiconductor device comprising an n-channel semiconductor layer comprising a compound of the formula:

2. The semiconductor device of claim 1, wherein said semiconductor layer comprises a compound of the formula:

3. The device of claim 1 wherein each R_f is independently a perfluoroalkoxyalkylene group or a perfluoropolyether group.

4. The device of claim 1 wherein each R_f corresponds to the formula:

R_f¹—

O—

(R_f²)_x—

(R_f³)—

wherein R¹_f represents a perfluoroalkyl group, R_f² represents a perfluorinated polyalkyleneoxy group consisting of perfluoroalkyleneoxy groups having 1 to 4 perfluorinated carbon atoms or a mixture of such perfluoroalkyleneoxy groups, R_f³ represents a perfluoroalkylene group, x is 0 to 25.

5. The device of claim 4 wherein each R_f² is independently selected from —

CF₂—

CF₂—

O—

, —

CF(CF₃)—

CF₂—

O—

, —

CF₂—

CF(CF₃)—

O—

, —

CF₂—

CF₂—

CF₂—

O—

, —

CF₂—

O—

, —

CF(CF₃)—

O—

, and —

CF₂—

CF₂—

CF₂—

CF₂—

O—

.

6. The device of claim 4 wherein each R_f³ is independently selected from —

CF₂—

CF₂—

, —

CF(CF₃)—

CF₂—

, —

CF₂—

CF(CF₃)—

, —

CF₂—

CF₂—

CF₂—

, —

CF₂—

O—

, —

CF(CF₃)—

, and —

CF₂—

CF₂—

CF₂—

CF₂—

.

7. The device of claim 4 wherein x is 1 to 4.

8. The device of claim 2 wherein R_f is R_f¹—

O—

[CF(CF₃)—

CF₂O]_x—

CF(CF₃)—

wherein R_f¹ is a perfluoroalkyl group and x is at least one.

9. The device of claim 4 wherein R_f¹ represents a perfluorinated alkyl group having 1 to 6 carbon atoms.

10. The device of claim 1 wherein n is 3 to 6.

11. The semiconductor device of claim 1, further comprising conducting layer, a dielectric layer, or a combination thereof adjacent to the semiconductor layer.

12. The semiconductor device of claim 1, wherein said semiconductor device comprises an organic thin film transistor.

13. The semiconductor device of claim 1, further comprising a source electrode and a drain electrode in contact with the semiconductor layer, wherein the source electrode and the drain electrode are separated by an area on the surface of the semiconductor layer.

14. The semiconductor device of claim 1, further comprising a conducting layer adjacent to one surface of the semiconducting layer and a dielectric layer adjacent to an opposite surface of the semiconducting layer.

21. A Schottky diode comprising the device of claim 1, wherein a first metal is in contact with a first surface of said semiconductor, and a second metal in contact with a second surface of said semiconductor layer.

15. A method of preparing an organic thin film transistor, said method comprising:

providing a gate electrode;

depositing a gate dielectric layer on a surface of the gate electrode;

preparing a semiconductor layer adjacent to the gate dielectric layer opposite the gate electrode, said semiconductor layer comprising a compound of the formula;

16. The method of claim 15 wherein said semiconductor layer comprises a compound of the formula:

17. The method of claim 15, further comprising depositing a surface treatment layer between the gate dielectric layer and the semiconductor layer.

18. A method of preparing an organic thin film transistor, said method comprising:

providing a gate electrode;

depositing a gate dielectric layer on a surface of the gate electrode;

positioning a source electrode and a drain electrode adjacent to the gate dielectric layer opposite the gate electrode, wherein the source electrode and the drain electrode are separated by an area over the gate dielectric layer;

preparing a semiconductor layer on a surface of the source electrode, on the surface of the drain electrode, and in the area between the source electrode and the drain electrode, said semiconductor layer comprising a compound of the formula;

19. The method of claim 18 wherein said semiconductor layer comprises a compound of the formula:

20. The method of claim 19, said method further comprising depositing a surface treatment layer that contacts the surface of the gate dielectric layer opposite the gate electrode.