Photo-patternable cross-bred organic semiconductor polymers for organic thin-film transistors

Patent metadata

Field	Value
Publication number	US-2022155683-A1
Application number	US-202017440387-A
Country	US
Kind code	A1
Filing date	Mar 5, 2020
Priority date	Mar 27, 2019
Publication date	May 19, 2022
Grant date	—

Abstract

A polymer blend, including at least one organic semiconductor (OSC) polymer, such that: the at least one OSC polymer is a diketopyrrolopyrrole-fused thiophene polymeric material, the fused thiophene is beta-substituted, the at least one OSC polymer has a first portion and a second portion, and at least one of the first portion or the second portion includes at least one UV-curable side chain.

First claim

1 . A polymer blend, comprising:
at least one organic semiconductor (OSC) polymer, wherein the at least one OSC polymer is a diketopyrrolopyrrole-fused thiophene polymeric material, wherein the fused thiophene is beta-substituted, and wherein the at least one OSC polymer comprises a first portion and a second portion, wherein at least one of the first portion or the second portion comprises at least one UV-curable side chain.

2 . The polymer blend of claim 1 , wherein the at least one UV-curable side chain comprises at least one of acrylates, epoxides, oxetanes, alkenes, alkynes, azides, thiols, allyloxysilanes, phenols, anhydrides, amines, cyanate esters, isocyanate esters, silyl hydrides, chalones, cinnamates, coumarins, fluorosulfates, silyl ethers, or combinations thereof.

3 . The polymer blend of claim 1 , wherein only the first portion comprises at least one UV-curable side chain.

4 . The polymer blend of claim 1 , wherein both the first portion and the second portion comprise the at least one UV-curable side chain.

5 . The polymer blend of claim 1 , further comprising: at least one crosslinker, wherein the at least one crosslinker comprises at least one of acrylates, epoxides, oxetanes, alkenes, alkynes, azides, thiols, allyloxysilanes, phenols, anhydrides, amines, cyanate esters, isocyanate esters, silyl hydrides, chalones, cinnamates, coumarins, fluorosulfates, silyl ethers, or combinations thereof.

6 . The polymer blend of claim 1 , further comprising: at least one photoinitiator, wherein the at least one photoinitiator is present in a range of 0.1 wt. % to 10 wt. %.

7 . (canceled)

8 . (canceled)

9 . The polymer blend of claim 1 , wherein the at least one OSC polymer comprises the repeat unit of Formula 1 or Formula 2, or a salt, isomer, or analog 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. 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.

10 . The polymer blend of claim 9 , wherein for the first portion, R 5 and R 7 are hydrogen and R 6 and R 8 are substituted or unsubstituted C 4 or greater alkenyl.

11 . The polymer blend of claim 9 , wherein for the first portion and the second portion, R 5 and R 7 are hydrogen and R 6 and R 8 are substituted or unsubstituted C 4 or greater alkenyl.

12 . The polymer blend of claim 9 , wherein at least one of R 5 , R 6 , R 7 , and R 8 comprise acrylates, epoxides, oxetanes, alkenes, alkynes, azides, thiols, allyloxysilanes, phenols, anhydrides, amines, cyanate esters, isocyanate esters, silyl hydrides, chalones, cinnamates, coumarins, fluorosulfates, silyl ethers, or combinations thereof.

13 . The polymer blend of claim 9 , wherein at least one of R 1 , R 2 , R 3 , and R 4 comprise acrylates, epoxides, oxetanes, alkenes, alkynes, azides, thiols, allyloxysilanes, phenols, anhydrides, amines, cyanate esters, isocyanate esters, silyl hydrides, chalones, cinnamates, coumarins, fluorosulfates, silyl ethers, or combinations thereof.

14 . The polymer blend of claim 1 , wherein the at least one UV-curable side chain comprises at least one of:
(A) a polymer selected from:

wherein n is an integer greater than or equal to two, or
(B) a small-molecule selected from:

or,
(C) a combination thereof.

15 - 17 . (canceled)

18 . A polymer blend, comprising:
at least one organic semiconductor (OSC) polymer, wherein the at least one OSC polymer comprises a structure of Formula 7:

wherein in Formula 7:
Acceptor 1 and Acceptor 2 are each electron withdrawing groups;
Donor 1 and Donor 2 are electron-donating groups;
a and b are, independently, integers greater than or equal to one;
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,
wherein:
(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) one of R 1 or R 2 and one of R 3 or R 4 are, independently, connected with Acceptor 1 and Acceptor 2;
(v) one of R 5 or R 6 and one of R 7 or R 5 are, independently, connected with Donor 1 and Donor 2; and
(vi) the at least one OSC polymer has a molecular weight of greater than 10,000.

19 . The polymer blend of claim 18 , wherein Acceptor 1 and Acceptor 2 are independently selected from the group comprising:

wherein A and B may be, independently, either S or O, and T is a connection terminus to

Assignees

• Corning Inc

Inventors

• Deng Huayun
• He Mingqian
• Li Yang
• Niu Weijun
• Wang Hongxiang

Classifications

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title

• G03F7/0382 Primary

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title