Granted Patent B2

US 7,902,363 · App. 11/986,019 · Granted Mar 8, 2011

Abstract

Claims (40)

1. A compound having the formula:

wherein each R 1 is an organic group comprising a 2-alkyl substituted alkyl group, a 3-alkyl substituted alkyl group, or a 3-alkyl substituted alkenyl group.

2. The compound of claim 1 , wherein R 1 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 R 1 independently is

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

wherein i, j, k, l, o, r, s and u are independently CH, CF, or N; L is a divalent C 1-10 alkyl group, a divalent C 1-10 haloalkyl group, or a covalent bond; and R 2 is a 2-alkyl substituted alkyl group, a 3-alkyl substituted alkyl group, or a 3-alkyl substituted alkenyl group.

5. The compound of claim 4 , wherein each R 2 is:

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

wherein:

i, j, k, l, o, r, s, u, i′, j′, k′, l′, o′, r′, s′, and u′ are independently CH, CF, or N;

L is a divalent C 1-10 alkyl group, a divalent C 1-10 haloalkyl group, or a covalent bond;

L′ is —C(O)—, —O—, —S—, or —S(O)—, a divalent C 1-10 alkyl group, a divalent C 1-10 haloalkyl group, or a covalent bond; and

R 3 is a 2-alkyl substituted alkyl group, a 3-alkyl substituted alkyl group, or a 3-alkyl substituted alkenyl group.

7. The compound of claim 6 , wherein R 3 is:

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

wherein R d is F; p is 0, 1 or 2; each q independently is 0 or 4; L′ is —CH 2 —, —CH 2 CH 2 —, —C(O)—, —O—, —S—, —S(O)—, or a covalent bond; and R 3 is a 2-alkyl substituted alkyl group, a 3-alkyl substituted alkyl group, or a 3-alkyl substituted alkenyl group.

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).

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 R 1 group thereon, wherein R 1 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.

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

Assignments (8)