Diimide-based semiconductor materials and methods of preparing and using the same

• US 7,902,363 B2
• Filed: 11/19/2007
• Issued: 03/08/2011
• Est. Priority Date: 11/17/2006
• Status: Active Grant

• Current Assignee: Flexterra, Inc.
• Original Assignee: Polyera Corporation
• Inventors: Yan, He, Marks, Tobin J., Facchetti, Antonio
• Primary Examiner(s): AULAKH, CHARANJIT
• Application Number:
  US11/986,019
• Publication Number:
  US 20080185577A1
• Time in Patent Office: 1,205 Days
• Field of Search: 546/37, 313/504
• US Class Current: 546/37
• CPC Class Codes: C07D 471/06 Peri-condensed systems
• CPC Class Codes: C07D 487/06 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
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product

Abstract

Diimide-based semiconductor materials are provided with processes for preparing the same. Composites and electronic devices including the diimide-based semiconductor materials also are provided.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein R¹ independently is a 2-alkyl substituted butyl group, a 2-alkyl substituted pentyl group, a 2-alkyl substituted hexyl group, a 2-alkyl substituted heptyl group, a 3-alkyl substituted butyl group, a 3-alkyl substituted pentyl group, a 3-alkyl substituted hexyl group, a 3-alkyl substituted heptyl group, a 3-alkyl substituted octyl group, or a 3,7-dialkyl substituted octyl group.

3. The compound of claim 1, wherein each R¹ independently is

4. The compound of claim 1, wherein each R¹ is:

5. The compound of claim 4, wherein each R² is:

6. The compound of claim 1, wherein R¹ is:

7. The compound of claim 6, wherein R³ is:

8. The compound of claim 1, wherein each R¹ is:

10. A composition comprising one or more compounds of claim 1 dissolved or dispersed in a liquid medium.

11. An article of manufacture comprising one or more compounds of claim 1, wherein the article of manufacture is a field effect transistor device, a photovoltaic device, or an organic light emitting diode device.

12. A thin film semiconductor comprising one or more compounds of claim 1.

13. A method of making an article of manufacture, the method comprising depositing a composition of claim 10 onto a substrate.

14. A method of making a compound of claim 1, the method comprising reacting a secondary imide nitrogen of a core structure of the compound to substitute a R¹ group thereon, wherein R¹ is as defined in claim 4.

15. A thin film semiconductor prepared from spin-coating a composition comprising one or more compounds of claim 1 onto a substrate.

16. An article of manufacture comprising the thin film semiconductor of claim 15, wherein the article of manufacture is a field effect transistor device, a photovoltaic device, or an organic light emitting diode device.

17. The article of manufacture of claim 16, wherein the article of manufacture is a field effect transistor device.

18. The article of manufacture of claim 11, wherein the article of manufacture is a field effect transistor device.

19. The method of claim 13, wherein depositing a composition comprises at least one of printing, spin coating, drop-casting, zone casting, dip coating, blade coating, spraying, and vapor deposition.

9. A compound selected from:

N,N′

-bis[(3S)-3,7-dimethyl-6-octenyl]-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(2-methylhexyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(2-ethylhexyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis{4-[(3S)-3,7-dimethyl-6-octenyl]phenyl}-1-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis{4-[4′

-((3S)-3,7-dimethyl-6-octenyl]biphenylyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis{4-[(3S)-3,7-dimethyl-6-octenyloxy]benzyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis[(3S)-3,7-dimethyl-6-octenyl]-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(2-methylhexyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(2-ethylhexyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis{4-[(3S)-3,7-dimethyl-6-octenyl]phenyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis{4-[4′

-((3S)-3,7-dimethyl-6-octenyl]biphenylyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide); and

N,N′

-bis{4-[(3S)-3,7-dimethyl-6-octenyloxy]benzyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide).

20. A field effect transistor device comprising a thin film semiconductor, wherein the thin film semiconductor comprises a compound of claim 9.