Organic semiconductor materials and precursors thereof

• US 20080249309A1
• Filed: 01/23/2008
• Published: 10/09/2008
• Est. Priority Date: 01/24/2007
• Status: Active Grant

• Current Assignee: Flexterra, Inc.
• Original Assignee: Polyera Corporation
• Inventors: Marks, Tobin J., Yan, He, Facchetti, Antonio
• Granted Patent: US 8,022,214 B2
• Time in Patent Office: Days
• US Class Current: 546/37
• CPC Class Codes: C07D 471/06 Peri-condensed systems
• CPC Class Codes: C07D 471/12 in which the condensed system contains three hetero rings
• 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

The present teachings provide novel organic semiconductor compounds and their soluble precursors, methods for preparing these compounds and precursors, as well as compositions, materials, articles, structures, and devices that incorporate such compounds.

Claims

1. A compound of formula I:

3. The compound of claim 1, wherein the compound has formula I′

4. The compound of claim 1, wherein c and g are CH, and b and f independently are C(Br) or C(CN).

5. The compound of claim 1, wherein L and L′

independently are selected from —

(CH₂)_p—

O—

(CH₂)_p—

, —

[(CH₂)_p—

O]_q—

, —

(CH₂)_q—

, —

C_qX_2q—

, and a covalent bond, X is F, p is 1, 2 or 3, and q is as defined in claim 1.

7. The compound of claim 1, wherein Q and Q′

independently are selected from;

8. The compound of claim 1, wherein Q and Q′

are selected from;

10. The compound of claim 1 selected from:

N,N′

-bis(9-anthracenyl)-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(9-anthracenyl)-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(9-anthracenyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(9-anthracenyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(anthracen-9-ylmethyl)-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(anthracen-9-ylmethyl)-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(anthracen-9-ylmethyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(anthracen-9-ylmethyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(2-(anthracen-9-yl)-ethyl)-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(2-(anthracen-9-yl)-ethyl)-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(2-(anthracen-9-yl)-ethyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(2-(anthracen-9-yl)-ethyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(3-(anthracen-9-yl)-propyl)-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(3-(anthracen-9-yl)-propyl)-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(3-(anthracen-9-yl)-propyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(3-(anthracen-9-yl)-propyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(2-(10-cyano-anthracen-9-yl)-ethyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(2-(10-cyano-anthracen-9-yl)-ethyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(2-(10-hexyl-anthracen-9-yl)-ethyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(2-(10-hexyl-anthracen-9-yl)-ethyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

-bis(3-(anthracen-2-yl)-propyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide), and

N,N′

-bis(3-(anthracen-2-yl)-propyl)-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide).

11. A thin film semiconductor comprising the compound of claim 1.

30. A method of preparing a thin film semiconductor material comprising the compound of claim 1, the method comprising:

preparing a precursor composition that comprises a compound of formula II

2. (canceled)

6. (canceled)

9. (canceled)

12-16. -16. (canceled)

17. A compound of formula II:

18. The compound of claim 17, wherein the compound has formula II′

19. The compound of claim 17, wherein c and g are CH, and b and f independently are C(Br) or C(CN).

20. The compound of claim 17, wherein L and L′

independently are selected from a covalent bond, —

CH₂—

, —

CH₂CH₂—

, and —

CH₂CH₂CH₂—

.

21. The compound of claim 17, wherein T and T′

independently are selected from;

22. The compound of claim 17, wherein T and T′

independently are selected from;

23. The compound of claim 17, wherein U′

, U″

, V′ and

V″

are C;

U′

″

is O, S, or S(O);

U and V independently are CH, CR^h, or N; and

R^h, at each occurrence, is selected from —

CN, —

CHO, —

C(O)—

C_1-10 alkyl, —

S(O)₂—

OC_1-10 alkyl, a C_1-10 alkyl group, a C_1-10 haloalkyl group, and a C_6-14 aryl group.

24. The compound of claim 17, wherein W and Z independently are selected from H, —

CN, —

CHO, —

C(O)—

OC_1-10 alkyl, —

S(O)₂—

OC_1-10 alkyl, a C_1-10 alkyl group, a C_1-10 haloalkyl group, and a C_6-14 aryl group, and W′ and

Z′

independently are selected from O, CH₂, CHF, CF₂, C(CN)₂, CH(CN), and C(CF₃)₂.

25. The compound of claim 17, wherein U and V, together with W and Z, form an optionally substituted C_3-10 cycloalkyl group or an optionally substituted 3-12 membered cycloheteroalkyl group, wherein the C_3-10 cycloalkyl group and the 3-12 membered cycloheteroalkyl group are selected from a cyclohexenyl group, a tetrahydrofuranyl group, a 1,3-dioxolanyl group, a pyrrolidinyl group, a pyrazolidinyl group, a triazolidinyl group, and a bicyclo[2.2.1]heptanyl group, and each of these groups optionally is substituted with 1-4 groups independently selected from an oxo group, a methyl group, and a phenyl group.

27. The compound of claim 17 selected from:

N,N′

-bis[9′

,10′

-dihydro-9′

, 10′

-(1,2′

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[9′

,10′

-dihydro-9′

, 10′

-(1″

,2″

-dicarbomethoxy)-etheno-antlrlacene-9′

-yl]-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[9′

,10′

-dihydro-9′

, 10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl-methyl]-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl-methyl]-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl-methyl]-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl-methyl]-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{2-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-ethyl}-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{2-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-ethyl}-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{2-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-ethyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{2-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-ethyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-propyl}-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-propyl}-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-propyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-etheno-anthracene-9′

-yl]-propyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-ethano-anthracene-9′

-yl]-propyl}-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-ethano-anthracene-9′

-yl]-propyl}-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-ethano-anthracene-9′

-yl]-propyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-dicarbomethoxy)-ethano-anthracene-9′

-yl]-propyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-ditrifluoromethyl)-etheno-anthracene-9′

-yl]-propyl}-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-ditrifluoromethyl)-etheno-anthracene-9′

-yl]-propyl}-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-ditrifluoromethyl)-etheno-anthracene-9′

-yl]-propyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,2″

-ditrifluoromethyl)-etheno-anthracene-9′

-yl]-propyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(2″

,5″

-dioxo-tetrahydrofura-3″

,4″

-no)-anthracene-9′

-yl]-propyl}-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(2″

,5″

-dioxo-tetrahydrofura-3″

,4″

-no)-anthracene-9′

-yl]-propyl}-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(2″

,5″

-dioxo-tetrahydrofura-3″

,4″

-no)-anthracene-9′

-yl]-propyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(2″

,5″

-dioxo-tetrahydrofura-3″

,4″

-no)-anthracene-9′

-yl]-propyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,3″

-dioxolan-2″

-one-4″

,5″

-no)-anthracene-9′

-yl]-propyl}-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(1″

,3″

-dioxolan-2″

-one-4″

,5″

-no)-anthracene-9′

-yl]-propyl}-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

dihydro-9′

,10′

-(1″

,3″

-dioxolan-2″

-one-4″

,5″

-no)-anthracene-9′

-yl]-propyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

dihydro-9′

,10′

-(1″

,3″

-dioxolan-2″

-one-4″

,5″

-no)-anthracene-9′

-yl]-propyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(4″

-phenyl-1″

,2″

,4″

-triazolidine-3,5-dione-1″

,2″

-no)-anthracene-9′

-yl]-propyl}-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(4″

-phenyl-1″

,2″

,4″

-triazolidine-3,5-dione-1″

,2″

-no)-anthracene-9′

-yl]-propyl}-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(4″

-phenyl-1″

,2″

,4″

-triazolidine-3,5-dione-1″

,2″

-no)-anthracene-9′

-yl]-propyl}-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis{3-[9′

,10′

-dihydro-9′

,10′

-(4″

-phenyl-1″

,2″

,4″

-triazolidine-3,5-dione-1″

,2″

-no)-anthracene-9′

-yl]-propyl}-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[(methylurazolyl)anthracene-9′

-yl-propyl]-1,7-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[(methylurazolyl)anthracene-9′

-yl-propyl]-1,6-dibromoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[(methylurazolyl)anthracene-9′

-yl-propyl]-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide), and

N,N′

-bis[(methylurazolyl)anthracene-9′

-yl-propyl]-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide).

28. A composition comprising the compound of claim 17.

26. (canceled)

29. (canceled)

31-35. -35. (canceled)