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

• US 20080185577A1
• Filed: 11/19/2007
• Published: 08/07/2008
• Est. Priority Date: 11/17/2006
• Status: Active Grant

• Current Assignee: Flexterra, Inc.
• Original Assignee: Polyera Corporation
• Inventors: Marks, Tobin J., Yan, He, Facchetti, Antonio
• Granted Patent: US 7,902,363 B2
• Time in Patent Office: Days
• US Class Current: 257/40
• 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 Q is:

3. The compound of claim 2, wherein a, b, c, d, e, f, g and h are independently CH or C(CN).

4. The compound of claim 1, the compound having the formula:

5. The compound of claim 4, wherein each R¹ independently is a branched C_3-20 alkyl group or a branched C_3-20 alkenyl group.

7. The compound of claim 4, 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.

8. The compound of claim 4, wherein each R¹ independently is

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

16. The compound of claim 13, wherein each R² is an n-butyl group, a sec-butyl group, a hexyl group, an octyl group, a dodecanyl group, a tridecanyl group, a decenyl group, an —

O-dodecanyl group, or an —

O-tridecanyl group.

17. The compound of claim 16, wherein each R² is:

20. The compound of claim 4, wherein R¹ is:

23. The compound of claim 20, wherein R³ is an n-butyl group, a sec-butyl group, a hexyl group, an octyl group, a dodecanyl group, a tridecanyl group, a decenyl group, an —

O-dodecanyl group, or an —

O-tridecanyl group.

24. The compound of claim 23, wherein R³ is:

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

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

32. An article of manufacture comprising one or 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.

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

46. A method of making an article of manufacture, the method comprising depositing a composition of claim 29 onto a substrate, wherein the depositing a composition comprises at least one of printing, spin coating, drop-casting, zone casting, dip coating, blade coating, spraying, and vapor deposition.

49. 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 1.

6. (canceled)

9-12. -12. (canceled)

14. (canceled)

15. (canceled)

18. (canceled)

19. (canceled)

21. (canceled)

22. (canceled)

25. (canceled)

26. (canceled)

28. 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-n-hexylphenyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(4-n-dodecylphenyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

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

9,10-bis(dicarboxiamide);

N,N′

-bis(4-heptyloxyphenyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(4-biphenylyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis[4-(4′

-n-octylbiphenylyl)]-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-(2′

,3′

,4′

,5′

,6′

-pentafluorobiphenyl)]-1,7-dibromoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis[4-(4′

-n-octyl-2′

,3′

,5′

,6′

-tetrafluorobiphenyl)]-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis[4-(4′

-n-octyl-2,3,5,6-tetrafluorobiphenyl)]-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(benzyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(4-n-butylbenzyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide);

N,N′

-bis(4-sec-butylphenyl)-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(4-benzylphenyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis{4-[1-(2-phenylethyl)]phenyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(4-n-benzoylphenyl)-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-n-hexylphenyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(4-n-dodecylphenyl)-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-heptyloxyphenyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(4-biphenylyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis[4-(4′

-n-octylbiphenylyl)]-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);

N,N′

-bis[4-(2′

,3′

,4′

,5′

,6′

-pentafluorobiphenyl)]-1,6-dibromoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis[4-(4′

-n-octyl-2′

,3′

,5′

,6′

-tetrafluorobiphenyl)]-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis[4-(4′

-n-octyl-2,3,5,6-tetrafluorobiphenyl)]-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(benzyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(4-n-butylbenzyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide);

N,N′

-bis(4-sec-butylphenyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

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

9,10-bis(dicarboxiamide);

N,N′

-bis(4-benzylphenyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis{4-[1-(2-phenylethyl)]phenyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-bis(4-n-benzoylphenyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboxiamide);

N,N′

-{4-[(3S)-3,7-dimethyl-6-octenyl]phenyl}-2,6-dicyanonapthalene-1,4;

5,8-tetracarboxylicdiimide; and

N,N′

-bis{4-[(3S)-3,7-dimethyl-6-octenyl]phenyl}-2,3;

6,7-anthracenedicarboximide.

30. (canceled)

31. (canceled)

33. (canceled)

34. (canceled)

36-45. -45. (canceled)

47. (canceled)

48. (canceled)