Dpp with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers

Patent metadata

Field	Value
Publication number	US-2016222167-A1
Application number	US-201514968168-A
Country	US
Kind code	A1
Filing date	Dec 14, 2015
Priority date	Jan 29, 2015
Publication date	Aug 4, 2016
Grant date	—

Abstract

Described herein are compositions including hereocyclic fused thiophene based compounds, polymers based on fused thiophene compounds, and methods for making the monomer and polymer along with uses in thin film-based and other devices.

First claim

What is claimed is:

1 . A polymer comprising the repeat unit of formula 1′ or 2′

wherein, in the structure 1′ and 2′, m is an integer greater than or equal to one; n is 1 or 2; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may be, independently, hydrogen, substituted or unsubstituted C 4 or greater alkyl, substituted or unsubstituted C 4 or greater alkenyl, substituted or unsubstituted C 4 or greater alkynyl, or C 5 or greater cycloalkyl; a, b, c, and d are independently, integers greater than or equal to 3; e and f are integers greater than or equal to zero; X and Y are, independently a covalent bond, an optionally substituted aryl group, an optionally substituted heteroaryl, an optionally substituted fused aryl or fused heteroaryl group, an alkyne or an alkene; and A and B may be, independently, either S or O, with the provisos that:
i. at least one of R 1 or R 2 ; one of R 3 or R 4 ; one of R 5 or R 6 ; and one of R 7 or R 8 is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, or cycloalkyl;
ii. if any of R 1 , R 2 , R 3 , or R 4 is hydrogen, then none of R 5 , R 6 , R 7 , or R 8 are hydrogen;
iii. if any of R 5 , R 6 , R 7 , or R 8 is hydrogen, then none of R 1 , R 2 , R 3 , or R 4 are hydrogen;
iv. e and f cannot both be 0;
v. if either e or f is 0, then c and d, independently, are integers greater than or equal to 5; and
vi. the polymer having a molecular weight, wherein the molecular weight of the polymer is greater than 10,000.

2 . The polymer of claim 1 , wherein m is from 1 to 1000.

3 . The polymer of claim 1 , wherein A and B are O.

4 . The polymer of claim 1 , wherein A and B are S.

5 . The polymer of claim 1 , wherein a and b are integers greater than or equal to 3, and c and d are integers greater than or equal to 4.

6 . The polymer of claim 1 , wherein f is an integer greater than or equal to 1.

7 . The polymer of claim 6 , wherein f is 1 and e is 0.

8 . The polymer of claim 1 , wherein either R 1 , R 2 , R 3 , and R 4 , or R 5 , R 6 , R 7 , and R 8 , are an optionally substituted alkyl group comprising from 8 to 40 carbon atoms.

9 . The polymer of claim 8 , wherein all of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , are an optionally substituted alkyl group comprising from 8 to 40 carbon atoms.

10 . The polymer of claim 8 , wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 is an optionally substituted alkyl group comprising from 8 to 40 carbon atoms and R 6 and R 8 each are hydrogen.

11 . The polymer of claim 10 , wherein a and b are 3, 4, 5, or 6.

12 . The polymer of claim 8 , wherein each of R 5 , R 6 , R 7 , R 8 , R 1 , and R 3 is an optionally substituted alkyl group comprising from 8 to 40 carbon atoms and R 2 and R 4 each are hydrogen.

13 . The polymer of claim 12 , wherein c and d are 3, 4, 5, 6, or 7.

14 . The polymer of claim 1 , wherein each X and Y, independently, have one of the structures:

wherein each R 9 and R 10 is independently, hydrogen, substituted or unsubstituted alkyl having from 1 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 1 to 30 carbon atoms, substituted or unsubstituted alkynyl, having from 1 to 30 carbon atoms, substituted or unsubstituted aryl having from 4 to 30 carbon atoms, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aralkyl.

15 . The polymer of claim 14 , wherein each X and Y, independently, is one of the structures:

16 . The polymer of claim 14 , wherein each X and Y, independently, is one of the structures:

17 . The polymer of claim 16 , wherein at least one of X and Y is selected from substituted and unsubstituted thiophene groups.

18 . The polymer of claim 1 , wherein f is 1, e is 0, a and b are 3, 4, 5, or 6, c and d are 5, 6, or 7, all of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , are an optionally substituted alkyl group comprising from 8 to 40 carbon atoms, and X is one of the structures:

19 . The polymer of claim 1 , wherein f is 1, e is 0, a and b are 3, 4, 5, or 6, c and d are 5, 6, or 7, each of R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 is an optionally substituted alkyl group comprising from 8 to 40 carbon atoms and R 6 and R 8 each are hydrogen, and X is one of the structures:

20 . The polymer of claim 1 , wherein f is 1, e is 0, a and b are 3, 4, 5, or 6, c and d are 5, 6, or 7, each of R 5 , R 6 , R 7 , R 8 , R 1 , and R 3 is an optionally substituted alkyl group comprising from 8 to 40 carbon atoms and R 2 and R 4 each are hydrogen, and X is one of the structures.

21 . The polymer of claim 1 , chosen from compounds of formula 1A′ or 2A′:

wherein a and b are equal and are chosen from integers greater than or equal to 3, wherein c and d are equal and are chosen from integers greater than or equal to 3, n is 1 or 2, and A=B=0.

22 . The polymer of claim 21 , wherein a=b=c=d=3, 4, 5, or 6 and each of R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 is an optionally substituted alkyl group comprising from 8 to 40 carbon atoms and R 6 and R 8 each are hydrogen.

23 . The polymer of claim 21 , wherein a=b=c=d=3, 4, 5, or 6 and all of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , are an optionally substituted alkyl group comprising from 8 to 40 carbon atoms.

24 . The polymer of claim 21 , wherein a=b=c=d=3, 4, 5, or 6 and each of R 5 , R 6 , R 7 , R 8 , R 1 , and R 3 is an optionally substituted alkyl group comprising from 8 to 40 carbon atoms and R 2 and R 4 each are hydrogen.

25 . The polymer of claim 1 , chosen from compounds of formula 1AA′ or 2AA′:

wherein a and b are equal and are chosen from integers greater than or equal to 3, wherein c and d are equal and are chosen from integers greater than or equal to 5, n is 1 or 2, A=B=0, and R 9 =R 10 =H.

26 . The polymer of claim 25 , wherein a and b are 3, 4, 5, or 6, c and d are 5, 6, or 7, and each of R 1 , R 2 , R 3 , R 4 , R 5 , and R 7 is an optionally substituted alkyl group comprising from 8 to 40 carbon atoms and R 6 and R 8 each are hydrogen.

27 . The polymer of claim 25 , wherein a and b are 3, 4, 5, or 6, c and d are 5, 6, or 7, and all of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , are an optionally substituted alkyl group comprising from 8 to 40 carbon atoms.

28 . The polymer of claim 25 , wherein a and b are 3, 4, 5, or 6, c and d are 5, 6, or 7 and each of R 5 , R 6 ,

Assignees

• Corning Inc

Inventors

• He Mingqian
• Matthews James Robert
• Niu Weijun

Classifications

• H01L51/0558

  Electricity · mapped topic

• C08G75/00 Primary

  Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule · CPC title

• H01L51/0036

  Electricity · mapped topic

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• H10K10/484

  characterised by the channel regions · CPC title