Organic semiconductor materials and precursors thereof

• US 8,022,214 B2
• Filed: 01/23/2008
• Issued: 09/20/2011
• Est. Priority Date: 01/24/2007
• Status: Expired due to Fees

• Current Assignee: Flexterra, Inc.
• Original Assignee: Polyera Corporation
• Inventors: Marks, Tobin J., Yan, He, Facchetti, Antonio
• Primary Examiner(s): Aulakh; Charanjit
• Application Number:
  US12/011,030
• Publication Number:
  US 20080249309A1
• Time in Patent Office: 1,336 Days
• Field of Search: 546/37, 438/483, 313/498, 313/504
• 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′

;

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

are selected from;

3. 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).

4. A thin film semiconductor material comprising the compound of claim 1.

11. 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′

;

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

or wherein b and g are CH, and c and f independently are C(Br) or C(CN).

13. A composite comprising a substrate and the thin film semiconductor material of claim 4 deposited on the substrate.

14. An organic field effect transistor (OFET) device comprising the composite of claim 13.

15. An organic photovoltaic device comprising the composite of claim 13.

16. An organic photodetector an organic light-emitting device comprising the composite of claim 13.

17. The method of claim 11, wherein depositing comprises inkjet printing, screen-printing, gravure printing, pad printing, offset printing, microcontact printing, spin coating, drop-casting, dip coating, or blade coating.

18. The method of claim 11, wherein the thin film semiconductor precursor is converted to the thin film semiconductor material by heating only.

19. The method of claim 11, wherein the thin film semiconductor precursor is converted to the thin film semiconductor material by exposure to one or more of infrared light, ultraviolet light, ionizing radiation, and chemical reagents.

20. The method of claim 11, wherein the thin film semiconductor precursor is converted to the thin film semiconductor material by heating and exposure to one or more of infrared light, ultraviolet light, ionizing radiation, and chemical reagents.

5. A compound of formula II′

;

6. The compound of claim 5, 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.

7. The compound of claim 5, 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.

8. The compound of claim 5, 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.

9. The compound of claim 5 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-anthracene-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).

10. A composition comprising the compound of claim 5.