Methods for preparing arene-BIS (dicarboximide)-based semiconducting materials and related intermediates for preparing same

• US 7,893,265 B2
• Filed: 01/07/2008
• Issued: 02/22/2011
• Est. Priority Date: 01/08/2007
• Status: Active Grant

• Current Assignee: Flexterra, Inc.
• Original Assignee: Polyera Corporation
• Inventors: Marks, Tobin J., Yan, He, Facchetti, Antonio
• Primary Examiner(s): AULAKH, CHARANJIT
• Application Number:
  US12/006,934
• Publication Number:
  US 20080177073A1
• Time in Patent Office: 1,142 Days
• Field of Search: 546/37, 546/66, 548/418, 549/232, 549/234
• US Class Current: 546/37
• CPC Class Codes: C07D 471/06 Peri-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 491/06 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

Abstract

The present teachings provide compounds of formulae I and II:

• • where Q, R^a, R¹, W, and n are as defined herein. The present teachings also provide methods of preparing compounds of formulae I and II, including methods of preparing compounds of formula II from compounds of formula I. The compounds disclosed herein can be used to prepare semiconductor materials and related composites and electronic devices.

Claims

1. A compound of formula I:

2. The compound of claim 1 selected from:

3. A method of using a compound of formula I according to claim 1 for preparing a compound of formula II:

4. The method of claim 3, wherein the compound of formula I is selected from:

5. The method of claim 3, wherein R¹ is selected from a straight chain C_1-20 alkyl group, a branched C_1-20 alkyl group, a branched C_2-20 alkenyl group, a —

Y—

C_3-10 cycloalkyl group, a —

Y—

C_6-14 aryl group, a —

Y-3-12 membered cycloheteroalkyl group, a —

Y-5-14 membered heteroaryl group, wherein each of the C_1-20 alkyl groups, the C_2-20 alkenyl group, the C_3-10 cycloalkyl group, the C_6-14 aryl group, the 3-12 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group optionally is substituted with 1-5 -L-R³ groups, and L and R³ are as defined in claim 3.

6. The method of claim 3, wherein R¹ is selected from an n-octyl group, a (3S)-3,7-dimethyl-6-octenyl group, a (3S)-3,7-dimethyloctyl group, a 4-n-hexylphenyl group, a 4-picolyl group, a 6-tert-butyloxycarbonylaminohexyl group, a 9-anthracenyl group, an anthracen-9-ylmethyl group, and a 2-(anthracen-9-yl)-ethyl group.

7. The method of claim 3, wherein the compound of formula II is selected from:

N,N′

-bis[n-octyl]-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis[n-octyl]-1,6-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

-bis[(3S)-3,7-dimethyloctyl]-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

-bis(6-tert-butyloxycarbonylaminohexyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

-bis(6-tert-butyloxycarbonylaminohexyl)-1,6-dicyanoperylene-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-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-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′

-dioctyl-2,6-dicyanonapthalene-1,4;

5,8-bis(dicarboximide),

N,N′

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

5,8-bis(dicarboximide), and

N,N′

-dioctyl-9,10-dicyanoanthracene-2,3;

6,7-bis(dicarboximide).

8. The method of claim 3, wherein R¹ is selected from an optionally substituted aryl group, an optionally substituted biaryl group, an optionally substituted arylalkyl group, and an optionally substituted biarylalkyl group.

9. The method of claim 3, wherein the co-solvent system comprises a first solvent and a second solvent, wherein the first solvent is a polar protic solvent and the second solvent is a non-polar solvent or an aprotic solvent.

10. The method of claim 3, wherein the co-solvent system comprises xylene and propanoic acid.

11. The method of claim 9, wherein the first solvent is propanoic acid.

12. The method of claim 9, wherein the second solvent is xylene.

13. The compound of claim 1, wherein Q is a perylene moiety.

14. The compound of claim 1, wherein Q is a naphthalene moiety.

15. The method of claim 3, wherein Q is a perylene moiety.

16. The method of claim 3, wherein Q is a naphthalene moiety.

17. The method of claim 3, wherein the compound of formula I is obtained by reacting a cyanide with a compound of formula III

18. The method of claim 17, wherein the cyanide is selected from LiCN, NaCN, KCN, CuCN, AgCN, and trimethylsilyl cyanide.

19. A method for preparing a compound of formula I according to claim 1: