Uv patternable polymer blends for organic thin-film transistors

Patent metadata

Field	Value
Publication number	US-2024334806-A1
Application number	US-202418743348-A
Country	US
Kind code	A1
Filing date	Jun 14, 2024
Priority date	Nov 5, 2018
Publication date	Oct 3, 2024
Grant date	—

Abstract

A cross-bred organic semiconductor (OSC) polymer, includes a diketopyrrolopyrrole (DPP)-fused thiophene polymeric material, such that: the DPP-fused thiophene polymeric material comprises a first linear alkyl-substituted DPP portion and a second branched alkyl-substituted DPP portion, the cross-bred OSC polymer comprises a repeat unit having both the first linear alkyl-substituted DPP portion and the second branched alkyl-substituted DPP portion, and the fused thiophene is beta-substituted.

First claim

What is claimed is:

1 . A cross-bred organic semiconductor (OSC) copolymer, comprising:
a first diketopyrrolopyrrol (DPP)-fused thiophene portion comprising a first fused thiophene and a first linear alkyl-substituted DPP; and a second DPP-fused thiophene portion comprising a second fused thiophene and a second branched alkyl-substituted DPP; wherein, the first fused thiophene and second fused thiophene are beta-substituted.

2 . The copolymer of claim 1 , wherein the first DPP-fused thiophene portion and the second DPP-fused thiophene portion are present in a mole ratio of about 3:7.

3 . The copolymer of claim 1 , having the structure of:

where n is at least 4, x is at least 1, y is at least 1.

4 . The copolymer of claim 3 , wherein x and y are provided in a mole ratio of about 3:7.

5 . The copolymer of claim 3 , wherein each n is independently selected from 8, 10, 16, and 17.

6 . The copolymer of claim 1 , wherein the first DPP-fused thiophene portion and the second DPP-fused thiophene portion are each, independently, a repeat unit of Formula 1 or Formula 2, or a salt or isomer thereof:

wherein in Formula 1 and Formula 2:
m is an integer greater than or equal to one;
n is 0, 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. e and f cannot both be 0; and
iii. if either e or f is 0, then c and d, independently, are integers greater than or equal to 5.

7 . The copolymer of claim 6 , wherein the first DPP-fused thiophene portion is a repeat unit of Formula 2 or a salt or isomer thereof, wherein one of R 5 or R 6 and one of R 7 or R 8 is H.

8 . The copolymer of claim 7 , wherein one of R 1 or R 2 and one of R 3 or R 4 is H.

9 . The copolymer of claim 6 , wherein the first DPP-fused thiophene portion is a repeat unit of Formula 5:

10 . The copolymer of claim 6 , wherein the second DPP-fused thiophene portion is a repeat unit of Formula 2 or a salt or isomer thereof, wherein both of R 5 and R 6 and both of R 7 and R 8 are a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, or cycloalkyl.

11 . The copolymer of claim 10 , wherein one of R 1 or R 2 and one of R 3 or R 4 is H.

12 . The copolymer of claim 6 , wherein the second DPP-fused thiophene portion is a repeat unit of Formula 4:

13 . The copolymer of claim 6 , wherein the first DPP-fused thiophene portion and the second DPP-fused thiophene portion are present in a mole ratio of about 3:7.

14 . An organic semiconductor device comprising the copolymer of claim 1 .

15 . A method of making a cross-bred organic semiconductor (OSC) copolymer according to claim 1 , comprising:
reacting the first DPP-fused thiophene portion and the second DPP-fused thiophene portion.

16 . The method of claim 15 , further comprising:
reacting a first fused thiophene monomer with a first linear alkyl-substituted DPP monomer to form the first DPP-fused thiophene portion; and reacting a second fused thiophene monomer with a second branched alkyl-substituted DPP monomer to form the second DPP-fused thiophene portion.

17 . The method of claim 16 , wherein the step of reacting the first fused thiophene monomer with the first linear alkyl-substituted DPP monomer comprises:

where n is at least 4.

18 . The method of claim 16 , wherein the step of reacting the second fused thiophene monomer with the second branched alkyl-substituted DPP monomer comprises:

where n is at least 4.

19 . The method of claim 16 , wherein the steps of: (1) reacting the first fused thiophene monomer with the first linear alkyl-substituted DPP monomer; (2) reacting the second fused thiophene monomer with the second branched alkyl-substituted DPP monomer, and (3) reacting the first DPP-fused thiophene portion and the second DPP-fused thiophene portion comprises:

where n is at least 4. x is at least 1, y is at least 1.

20 . The method of claim 15 , wherein the step of reacting the first DPP-fused thiophene portion and the second DPP-fused thiophene portion comprises:

where n is at least 4.

Assignees

• Corning Inc

Inventors

• Deng Huayun
• He Mingqian
• Li Xin
• Li Yang
• Niu Weijun
• Wallace Arthur Lawrence
• Wang Hongxiang

Classifications

• C08G2261/3223

  containing one or more sulfur atoms as the only heteroatom, e.g. thiophene · CPC title

• C08G2261/3241

  containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole · CPC title

• C08G2261/3243

  containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene · CPC title

• C08G2261/1412

  Saturated aliphatic units · CPC title

• C08G2261/122

  statistical · CPC title