Perylene n-type semiconductors and related devices

• US 20050176970A1
• Filed: 01/26/2005
• Published: 08/11/2005
• Est. Priority Date: 01/26/2004
• Status: Active Grant

• Current Assignee: Northwestern University
• Original Assignee: DARPA
• Inventors: Marks, Tobin J., Facchetti, Antonio, Wasielewski, Michael R., Jones, Brooks A., Ahrens, Michael J., Yoon, Myung-Han
• Granted Patent: US 7,671,202 B2
• Time in Patent Office: Days
• US Class Current: 549/41
• CPC Class Codes: C07D 221/14 Aza-phenalenes, e.g. 1,8-naphthalimide
• CPC Class Codes: C07D 221/18 Ring systems of four or more rings
• CPC Class Codes: C07D 471/06 Peri-condensed systems
• CPC Class Codes: C09B 5/62 Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
• CPC Class Codes: C09B 57/08 Naphthalimide dyes; Phthalimide dyes
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Mono- and diimide perylene and naphthalene compounds, N- and core-substituted with electron-withdrawing groups, for use in the fabrication of various device structures.

Claims

1. An n-type semiconductor compound of a formula selected from

2. The compound of claim 1 wherein at least one of A, D, E, H, K and L is one of said substituents and said moieties.

3. The compound of claim 2 wherein said substituents are selected from fluorine and substituents having a Hammett σ

⁺ value ≧

0.3; and

said moieties are selected from alkyl, cycloalkyl and aryl.

4. The compound of claim 3 wherein at least one of A, D, E, H, K and L is a cyano substituent.

5. The compound of claim 1 wherein at least one of I and J are selected from C_n alkyl and halo-substituted alkyl moieties.

6. The compound of claim 5 wherein n ranges from about 3 to about 16.

7. The compound of claim 6 wherein I and J are independently selected from C_n alkyl and fluoro-substituted alkyl moieties;

and at least one of A, D, E, H, K and L is a cyano substituent.

8. An n-type semiconductor compound of a formula selected from

9. The compound of claim 8 wherein I and J are selected from C_n alkyl and halo-substituted alkyl moieties, and n ranges from about 3 to about 16.

10. The compound of claim 9 wherein compound is dicyano-substituted.

11. An n-type semiconductor compound of a formula selected from

12. The compound of claim 11 wherein A and D are cyano substituents.

13. The compound of claim 11 wherein one of G and H is a cyano substituent.

14. The compound of claim 11 wherein E and F are selected from C_n alkyl and fluoro-substituted alkyl moieties, and n ranges from about 3 to about 16.

15. A composite comprising a substrate;

and a semiconductor component thereon, said component comprising a compound of a formula selected from

16. The composite of claim 15 wherein said compound is dicyano-substituted;

and I and J are selected from C_n alkyl and fluoro-substituted alkyl moieties, and n ranges from about 3 to about 16.

17. The composite of claim 16 incorporated into an OFET device.

18. A method of using perylene core substitution to enhance oxidative stability, said method comprising:

providing a cyano-substituted perylene compound of a formula selected from

wherein each of A, D, E, H, K and L is independently selected from H and a cyano substituent, and at least one of A, D, E, H, K and L is a cyano substituent; and

I and J are independently selected from H, alkyl, halo-substituted alkyl, cycloalkyl, and halo-substituted cycloalkyl moieties, said compound cyano-substituted sufficient to lower the reduction potential of said compound compared to perylene.

19. The method of claim 18 wherein at least one of A, D, E, H, K and L is a cyano substituent.

20. The method of claim 19 incorporating said compound into an OFET device.