N-type semiconductors and related devices

• US 7,982,039 B2
• Filed: 12/29/2009
• Issued: 07/19/2011
• Est. Priority Date: 01/26/2004
• Status: Active Grant

• Current Assignee: Northwestern University
• Original Assignee: Northwestern University
• Inventors: Jones, Brooks A., Ahrens, Michael J., Yoon, Myung-Han, Marks, Tobin J., Facchetti, Antonio, Wasielewski, Michael R.
• Primary Examiner(s): Aulakh; Charanjit
• Application Number:
  US12/648,484
• Publication Number:
  US 20100204475A1
• Time in Patent Office: 567 Days
• Field of Search: 546/38, 438/483, 313/498
• US Class Current: 546/38
• 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/or core-substituted with electron-withdrawing groups, for use in the fabrication of various device structures.

Claims

1. An n-type semiconductor compound having formula II:

2. The compound of claim 1, wherein R⁹ is selected from an alkyl moiety, a substituted alkyl moiety, and a substituted aryl moiety.

3. The compound of claim 2, wherein R⁹ is a halo substituted alkyl moiety.

4. The compound of claim 3, wherein the halo substituted alkyl moiety comprises F or Cl.

5. The compound of claim 1, wherein at least one of R¹¹ and R¹² is —

CN.

6. The compound of claim 5, wherein each of R¹, R⁴, and R¹¹ is —

CN.

7. The compound of claim 5, wherein at least one of R¹, R⁴, R⁵, and R⁸ is a halide.

9. A composite comprising a substrate and a semiconductor component thereon, said semiconductor component comprising the compound of claim 1.

10. A field-effect transistor comprising the composite of claim 9.

11. A photovoltaic device comprising the composite of claim 9.

12. A composite comprising a substrate and a semiconductor component thereon, said semiconductor component comprising the compound of claim 2.

13. A field-effect transistor comprising the composite of claim 12.

14. A photovoltaic device comprising the composite of claim 12.

15. A composite comprising a substrate and a semiconductor component thereon, said semiconductor component comprising the compound of claim 5.

16. A field-effect transistor comprising the composite of claim 15.

17. A photovoltaic device comprising the composite of claim 15.

8. An n-type semiconductor compound selected from:

N-(2,5-di-tert-butylphenyl)-9-cyano-1,6-bis(3,5-di-tert-butylphenoxy)-perylene-3,4-dicarboximide; and

N-(2,5-di-tert-butylphenyl)-1,6,9-tricyano-perylene-3,4-dicarboximide.

18. A composite comprising a substrate and a semiconductor component thereon, said semiconductor component comprising the compound of claim 8.

19. A field-effect transistor comprising the composite of claim 18.

20. A photovoltaic device comprising the composite of claim 18.