Polymer and composition for forming an anti-reflective film and method of manufacturing an integrated circuit device using the anti-reflective film

Patent metadata

Field	Value
Publication number	US-11650502-B2
Application number	US-201916695569-A
Country	US
Kind code	B2
Filing date	Nov 26, 2019
Priority date	Mar 28, 2019
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

A polymer having a repeating unit represented by Formula 1:wherein each of R1, R2, and R3 is independently selected from a substituted or unsubstituted C1-C6 chain-like saturated or unsaturated hydrocarbon group having 0 to 2 first heteroatoms or a substituted or unsubstituted C3-C6 cyclic saturated or unsaturated hydrocarbon group having 0 to 2 first heteroatoms, wherein at least one of R1, R2, and R3 is a hydrocarbon group substituted with a fluorine atom. R4 is a C1-C10 chain-like saturated or unsaturated hydrocarbon group having 0 to 2 second heteroatoms or a C3-C10 cyclic saturated or unsaturated hydrocarbon group having 0 to 2 second heteroatoms. R5 is a C1-C10 chain-like saturated or unsaturated hydrocarbon group having 1 to 6 third heteroatoms or a C3-C10 cyclic saturated or unsaturated hydrocarbon group having 1 to 6 third heteroatoms.

First claim

What is claimed is:

1. A polymer having a repeating unit represented by Formula 1:

wherein each of R 1 , R 2 , and R 3 is independently selected from a substituted or unsubstituted C1-C6 saturated or unsaturated hydrocarbon group having 0 to 2 first heteroatoms or a substituted or unsubstituted C3-C6 cyclic saturated or unsaturated hydrocarbon group having 0 to 2 first heteroatoms, wherein at least one of R 1 , R 2 , and R 3 is a hydrocarbon group substituted with at least one fluorine atom,
R 4 is a C1-C10 saturated or unsaturated hydrocarbon group having 0 to 2 second heteroatoms or a C3-C10 cyclic saturated or unsaturated hydrocarbon group having 0 to 2 second heteroatoms, and
R 5 is a C1-C10 saturated or unsaturated hydrocarbon group having 1 to 6 third heteroatoms or a C3-C10 cyclic saturated or unsaturated hydrocarbon group having 1 to 6 third heteroatoms.

2. The polymer of claim 1 , wherein the first heteroatoms are an oxygen atom (O), and each of the second heteroatoms and the third heteroatoms are at least one selected out of the oxygen atom (O) and a nitrogen atom (N).

3. The polymer of claim 1 , wherein each of R 1 , R 2 , and R 3 is independently selected from a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C1-C6 heteroalkyl group, a substituted or unsubstituted C1-C6 alkoxy group, a substituted or unsubstituted C1-C6 heteroalkoxy group, a substituted or unsubstituted C2-C6 alkenyl group, a substituted or unsubstituted C2-C6 heteroalkenyl group, a substituted or unsubstituted C2-C6 alkynyl group, or a substituted or unsubstituted C2-C6 heteroalkynyl group.

4. The polymer of claim 1 , wherein:
each of R 1 , R 2 , and R 3 is independently selected from —CF 3 , —CH 2 CF 3 , —CF 2 CF 3 , —CF 2 CF 2 CF 3 , —OC(CH 3 ) 3 , —OCH 2 CF 3 , —OCF 3 , or —OCF 2 CF 3 ; and
at least one of R 1 , R 2 , and R 3 comprises the at least one fluorine atom.

5. The polymer of claim 1 , wherein R 1 , R 2 , and R 3 have a same structure.

6. The polymer of claim 1 , wherein two of R 1 , R 2 and R 3 have a same structure.

7. The polymer of claim 1 , wherein R 4 is selected from the following structures:

wherein * is a bonding position.

8. The polymer of claim 1 , wherein R 5 is selected from the following structures:

wherein * is a bonding position.

9. A composition comprising an organic solvent and a polymer having a repeating unit represented by Formula 1:

wherein each of R 1 , R 2 , and R 3 is independently selected from a substituted or unsubstituted C1-C6 saturated or unsaturated hydrocarbon group having 0 to 2 first heteroatoms or a substituted or unsubstituted C3-C6 cyclic saturated or unsaturated hydrocarbon group having 0 to 2 first heteroatoms, wherein at least one of R 1 , R 2 , and R 3 is a hydrocarbon group that is substituted with at least one fluorine atom,
R 4 is a C1-C10 saturated or unsaturated hydrocarbon group having 0 to 2 second heteroatoms or a C3-C10 cyclic saturated or unsaturated hydrocarbon group having 0 to 2 second heteroatoms, and
R 5 is a C1-C10 saturated or unsaturated hydrocarbon group having 1 to 6 third heteroatoms or a C3-C10 cyclic saturated or unsaturated hydrocarbon group having 1 to 6 third heteroatoms.

10. The composition of claim 9 , wherein:
each of R 1 , R 2 , and R 3 is independently selected from —CF 3 , —CH 2 CF 3 , —CF 2 CF 3 , —CF 2 CF 2 CF 3 , —OC(CH 3 ) 3 , —OCH 2 CF 3 , —OCF 3 , or —OCF 2 F 3 ; and
at least one of R 1 , R 2 , and R 3 comprises the at least one fluorine atom.

11. The composition of claim 9 , further comprising a polymer having a repeating unit represented by Formula 2:

wherein R 6 is a C6-C12 saturated or unsaturated hydrocarbon group having 0 to 2 fourth heteroatoms.

12. The composition of claim 11 , wherein R 6 is selected from one of the following structures:

wherein * is a bonding position.

13. The composition of claim 9 , further comprising at least one of a crosslinking agent and an acid generator.

Assignees

• Samsung Electronics Co Ltd
• Dongjin Semichem Co Ltd

Inventors

• Kang Miyeong
• Hong Sukkoo
• Kim Hyereun
• Kim Jihyun
• Kim Hyunjin
• Roh Hyojung
• Park Jongkyoung
• Lee Jungyoul

Classifications

• C09D175/04 Primary

  Polyurethanes · CPC title

• C08G71/04

  Polyurethanes · CPC title

• C08G18/3802

  having halogens · CPC title

• G03F7/26

  Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence) · CPC title

• G03F7/091 Primary

  characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement · CPC title