CNT film coated substrate using click reaction and manufacturing method thereof

Patent metadata

Field	Value
Publication number	US-12516196-B2
Application number	US-202217655698-A
Country	US
Kind code	B2
Filing date	Mar 21, 2022
Priority date	Apr 19, 2021
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

Provided is a CNT film coated substrate in which CNT is fixed to a substrate using a click reaction, so that a CNT film is uniformly formed with a high density and adhesive strength between the CNT film and the substrate is excellent to have high stability to water or an organic solvent. In the case of the conventional CNT film which was manufactured by spin coating, most of CNT was peeled off in a washing process, but in the case of the CNT film coated substrate according to the present invention, a high-density uniform CNT film coated substrate may be manufactured even after washing, and reproducibility between substrates may be secured.

First claim

The invention claimed is:

1 . A manufacturing method of a CNT film coated substrate, the method comprising:
applying and fixing a compound represented by Chemical Formula 2 on a base substrate layer; immersing the base substrate layer on which the compound is applied and fixed into a P 2 (CNT) solution; performing a click reaction of the compound represented by Chemical Formula 2 and a compound represented by Chemical Formula 3 to form Chemical Formula 1; and after completing the click reaction, washing unreacted compounds with an organic solvent, wherein
the CNT film coated substrate comprises:
the base substrate layer;
a P 1 polymer coating layer formed on the base substrate layer; and
a P 2 (CNT) polymer coating layer formed on the P 1 polymer coating layer, wherein
in the P 2 (CNT) polymer coating layer, CNT is wrapped by a P 2 polymer, and
the P 1 polymer coating layer and the P 2 (CNT) polymer coating layer are bonded by a triazole ring,
the CNT of the P 2 (CNT) polymer coating layer includes a semiconductive single-walled carbon nanotube (sc-SWCNT),
the CNT film coated substrate includes Chemical Formula 1:

the P 1 polymer coating layer is formed from the compound represented by Chemical Formula 2:
P 1 —(F 1 ) x ,  Chemical Formula 2

wherein F 1 is an alkynyl functional group, and x is an integer of 1 or more, and
the P 2 (CNT) polymer coating layer is formed from the compound represented by Chemical Formula 3:
P 2 —(F 2 ) y ,  Chemical Formula 3

wherein F 2 is an azide functional group, and y is an integer of 1 or more.

2 . The manufacturing method of the CNT film coated substrate of claim 1 , wherein the applying and fixing of the compound represented by Chemical Formula 2 on the base substrate layer includes:
washing the base substrate layer with a solvent; applying a self-assembled monolayer (SAM); applying the compound represented by Chemical Formula 2; performing UV curing; and washing compounds unfixed to the substrate layer with a solvent.

3 . The manufacturing method of the CNT film coated substrate of claim 2 , wherein in the applying of the compound represented by Chemical Formula 2, the compound represented by Chemical Formula 2 is represented by the following Chemical Formula 4:

wherein
F 1 is an alkynyl functional group;
p 1 and p 2 are repeating units derived from a monomer having the F 1 functional group at the end;
z and k are an integer of 1 to 7; and
a and b are an integer of 1 or more.

4 . The manufacturing method of the CNT film coated substrate of claim 3 , wherein Chemical Formula 4 is represented by the following Chemical Formula 6:

wherein
Ar is a trivalent aromatic radical;
R 1 and R 2 are independently of each other C 1-50 alkylene, C 3-50 cycloalkylene, C 6-50 arylene, C 3-50 heteroarylene, C 1-50 alkoxycarbonylene, or a combination thereof;
the alkylene, cycloalkylene, arylene, heteroarylene, and alkoxycarbonylene are optionally substituted with one or more selected from hydroxy, halogen, nitro, cyano, amino, carboxyl, a carboxylic acid salt, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 1-20 haloalkyl, C 1-20 alkoxy, C 1-20 alkoxycarbonyl, C 3-30 cycloalkyl, (C 6-30 ) aryl (C 1-20 ) alkyl, C 6-30 aryl, and C 3-30 heteroaryl;
F 1 is an alkynyl functional group;
z and k are an integer of 1 to 7; and
a and b are an integer of 1 or more.

5 . The manufacturing method of the CNT film coated substrate of claim 1 , wherein the applying and fixing of the compound represented by Chemical Formula 2 on the base substrate layer includes:
washing the base substrate layer with a solvent; applying the compound represented by Chemical Formula 2; performing a heat treatment; and washing compounds unfixed to the substrate layer with a solvent.

6 . The manufacturing method of the CNT film coated substrate of claim 5 , wherein the compound represented by Chemical Formula 2 is represented by the following Chemical Formula 5:

wherein
F 1 is an alkynyl functional group;
F 3 is an epoxy functional group;
p 1 and p 2 are repeating units derived from a monomer having the F 1 functional group at the end;
p 3 is a repeating unit derived from a monomer having the F 3 functional group at the end;
z, k, and t are an integer of 1 to 7; and
a, b, and c are an integer of 1 or more.

7 . The manufacturing method of the CNT film coated substrate of claim 6 , wherein Chemical Formula 5 is represented by the following Chemical Formula 8:

wherein
Ar is a trivalent aromatic radical;
R 1 , R 2 and R 4 are independently of one another C 1-50 alkylene, C 3-50 cycloalkylene, C 6-50 arylene, C 3-50 heteroarylene, C 1-50 alkoxycarbonylene, or a combination thereof;
the alkylene, cycloalkylene, arylene, heteroarylene, and alkoxycarbonylene are optionally substituted with one or more selected from hydroxy, halogen, nitro, cyano, amino, carboxyl, a carboxylic acid salt, C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 1-20 haloalkyl, C 1-20 alkoxy, C 1-20 alkoxycarbonyl, C 3-30 cycloalkyl, (C 6-30 ) aryl (C 1-20 ) alkyl, C 6-30 aryl, and C 3-30 heteroaryl;
R 5 is hydrogen or C 1-3 alkyl;
F 1 is an alkynyl functional group;
F 3 is an epoxy functional group;
z, k, and t are an integer of 1 to 7; and
a, b, and c are an integer of 1 or more.

8 . The manufacturing method of the CNT film coated substrate of claim 1 , wherein in the immersing the coated base substrate layer in the P 2 (CNT) solution, the P 2 (CNT) solution includes the compound represented by Chemical Formula 3, CNT, and a solvent.

9 . The manufacturing method of the CNT film coated substrate of claim 1 , wherein in the performing a click reaction of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3, a density of the CNT film is adjusted depending on a click reaction time.

Assignees

• Korea Res Inst Chemical Tech

Inventors

• Lim Bogyu
• Jung Seo Hyun
• Jung Yu Jin
• Park Jong Mok
• Kong Ho Youl
• Yoon Suyeol
• Kim Ye Jin
• Kim Ga Young
• Park Kwang Hun

Classifications

• C08K3/041

  Carbon nanotubes · CPC title

• B05D2201/02

  Polymeric substrate · CPC title

• C09D139/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers · CPC title

• C01B32/168

  After-treatment · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title