Acene-based organic semiconductor materials and methods of preparing and using the same

• US 7,892,454 B2
• Filed: 11/19/2007
• Issued: 02/22/2011
• Est. Priority Date: 11/17/2006
• Status: Active Grant

• Current Assignee: Flexterra, Inc., Northwestern University
• Original Assignee: Northwestern University, Polyera Corporation
• Inventors: Marks, Tobin J., Wang, Zhiming M., Facchetti, Antonio
• Primary Examiner(s): Kopec; Mark
• Assistant Examiner(s): Thomas; Jaison P
• Application Number:
  US11/986,017
• Publication Number:
  US 20080185555A1
• Time in Patent Office: 1,191 Days
• Field of Search: 252/500, 257/40, 548/418
• US Class Current: 252/500
• CPC Class Codes: C09B 5/62 Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 30/20 comprising organic-organic junctions, e.g. donor-acceptor junctions
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• 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
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product

Abstract

Acene-based compounds that can be used to prepare n-type semiconductor materials are provided with processes for preparing the same. Composites and electronic devices including n-type semiconductor materials prepared from these compounds also are provided.

Claims

1. A field effect transistor device comprising a thin film semiconductor comprising a compound having the formula:

2. The device of claim 1, wherein R^g is CN.

3. The device of claim 1, wherein R⁹ and R¹⁰ are C(CN), and q and q′

are 0.

4. The device of claim 3, wherein R^a is a straight chain C_1-10 alkyl group or a branched chain C_1-10 alkyl group.

5. The device of claim 3, wherein R^a is a straight chain C_2-10 alkenyl group or a branched chain C_2-10 alkenyl group.

6. The device of claim 3, wherein R^a is a C_1-10 haloalkyl group or a phenyl group substituted with 1-5 halogen groups.

7. The device of claim 1 comprising a thin film semiconductor comprising a compound selected from:

8. A field effect transistor device comprising a thin film semiconductor comprising a compound having the formula:

9. A field effect transistor device comprising a thin film semiconductor comprising a compound having the formula:

10. The device of claim 9, wherein each R^a is a perfluorophenyl group.