Water-soluble diacetylene, photolithography composition comprising water-soluble diacetylene monomer and conductive polymer, and fine pattern preparation method using same

Patent metadata

Field	Value
Publication number	US-11131925-B2
Application number	US-201716098358-A
Country	US
Kind code	B2
Filing date	Apr 26, 2017
Priority date	May 2, 2016
Publication date	Sep 28, 2021
Grant date	Sep 28, 2021

Abstract

Provided are a novel water-soluble diacetylene monomer, a composition for photolithography including the novel water-soluble diacetylene monomer and a conductive polymer, and a method of forming micropatterns using the composition. The water-soluble diacetylene monomer may not aggregate even when mixed with a water-soluble conductive polymer. Accordingly, a uniform composition for photolithography can be prepared by mixing a water-soluble conductive polymer with the diacetylene monomer, and micropatterns can be formed using the composition. More particularly, when the composition is formed into a thin film and then is irradiated with light, only light-irradiated portions of the diacetylene monomer are selectively crosslinked due to photopolymerization, thereby resulting in insoluble negative-type micropatterns.

First claim

The invention claimed is:

1. A composition for photolithography comprising a water-soluble conductive polymer and a water-soluble diacetylene monomer of the following Formula 1:
CH 3 —(CH 2 ) n —C≡C—C≡C—(CH 2 ) m -A-(CH 2 ) x -B  [Formula 1]

wherein n is 2 to 20, m is 2 to 15, and x is 0 to 10,
A is CONH, COO, or CONH—Ar wherein Ar is a phenyl group or a naphthalene group, and when A is CONH—Ar, x is 0,
B is OSO 3 B′ or OPO 3 B′, and
B′ is H, Li, Na, K, Rb or Cs.

2. The composition of claim 1 , wherein the water-soluble conductive polymer is poly(3,4-ethylenedioxythiophene)(PEDOT):poly(styrenesulfonate)(PSS).

3. The composition of claim 1 , wherein the compound of Formula 1 is a compound of the following Formula 2:
CH 3 —(CH 2 ) 11 —C≡C—C≡C—(CH 2 ) 8 —C(O)—NH—(CH 2 ) 2 —OSO 3 Na  [Formula 2]

4. The composition of claim 2 , further comprising water, wherein the water is included in an amount of 10,000 to 50,000 parts by weight based on 100 parts by weight of the water-soluble conductive polymer.

5. The composition of claim 2 , wherein the water-soluble diacetylene monomer is included in an amount of 0.01 to 50 parts by weight based on 100 parts by weight of the water-soluble conductive polymer.

6. A method of forming fine patterns comprising:
providing the composition of claim 1 ;
forming a conductive polymer-containing thin film by coating the composition for photolithography on a substrate; and
forming conductive polymer fine patterns by disposing a photomask on the conductive polymer-containing thin film, irradiating the photomask with ultraviolet light to form a first region, which includes polydiacetylene formed by crosslinking of the diacetylene monomer along with the conductive polymer, and a second region, in which the diacetylene monomer remains due to the photomask blocking ultraviolet light, and selectively removing the second region.

7. The method of claim 6 , wherein the substrate is a silicon wafer, a glass substrate, a plastic substrate, a paper, or a metal substrate.

8. The method of claim 6 , further comprising doping the conductive polymer fine patterns by applying a dopant of one or more selected from the group consisting of sulfuric acid, sulfonic acid, formic acid, hydrochloric acid, perchloric acid, nitric acid, acetic acid, dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and ethylene glycol.

9. The method of claim 8 , wherein the polydiacetylene in the fine patterns is decomposed during the doping step.

10. The method of claim 6 , wherein the fine patterns are electrodes for an organic electronic device.

Assignees

• Univ Hanyang Ind Univ Coop Found

Inventors

• Kim Jongman
• Lee Chanwoo
• Kim Taegeun
• Uh Kyungchan

Classifications

• G03F7/025 Primary

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon triple bonds, e.g. acetylenic compounds (G03F7/075 takes precedence) · CPC title

• C07C305/04 Primary

  being acyclic and saturated · CPC title

• C08L81/02

  Polythioethers; Polythioether-ethers · CPC title

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• C08F38/00

  Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds · CPC title