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

• US 20080177073A1
• Filed: 01/07/2008
• Published: 07/24/2008
• 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
• Granted Patent: US 7,893,265 B2
• Time in Patent Office: Days
• US Class Current: 546/34
• 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 having formula I:

2. The compound of claim 1, wherein Q—

(R^a)_n is selected from;

3. The compound of claim 1, wherein R^a is —

CN, —

NO₂, or —

C(O)CH₃.

4. The compound of claim 2, wherein a, b, c, d, e, f, g, and h, at each occurrence, are independently selected from CH, C(CN), and C[C(O)CH₃].

5. The compound of claim 1, wherein n is 2 or 4.

6. The compound of claim 1, the compound being selected from:

7. A method for preparing a compound having formula II:

8. The method of claim 7, wherein Q—

(R^a)_n is selected from;

9. The method of claim 7, wherein R^a is —

CN, —

NO₂, or —

C(O)CH₃.

10. The method of claim 8, wherein a, b, c, d, e, f, g, and h, at each occurrence, independently are selected from CH, C(CN), and C[C(O)CH₃].

11. The method of claim 7, wherein n is 2 or 4.

12. The method of claim 7, wherein the compound having the formula Ia or Ib is selected from:

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

14. The method of claim 7, 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 7.

15. The method of claim 7, 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 anthracene-9-ylmethyl group, and a 2-(anthracen-9-yl)-ethyl group.

16. The method of claim 7, 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(anthracene-9-ylmethyl)-1,7-dicyanoperylene-3,4;

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

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

9,10-bis(dicarboximide),

N,N′

-bis(2-(anthracene-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).

17. The method of claim 7, 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.

18. The method of claim 7, wherein the reacting step is carried out in a co-solvent system.

19. The method of claim 18, wherein the co-solvent system comprises a polar protic solvent and a non-polar or low-polarity solvent.

20. The method of claim 7, wherein the reacting step is carried out in xylene and propanoic acid.

21. The method of claim 7, wherein the compound of formula II is used to fabricate a semiconductor material.