Monomer for hardmask composition and hardmask composition including the monomer and method of forming patterns using the hardmask composition

Patent metadata

Field	Value
Publication number	US-9158201-B2
Application number	US-201314079990-A
Country	US
Kind code	B2
Filing date	Nov 14, 2013
Priority date	Dec 28, 2012
Publication date	Oct 13, 2015
Grant date	Oct 13, 2015

Abstract

A monomer for a hardmask composition is represented by the following Chemical Formula 1,

First claim

What is claimed is:

1. A monomer for a hardmask composition, the monomer being represented by the following Chemical Formula 1:

wherein, in the above Chemical Formula 1,
A 1 is a substituted or unsubstituted aliphatic cyclic group or a substituted or unsubstituted aromatic cyclic group,
A 2 to A 4 are each a phenylene group,
X 1 is a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C20 alkylamine group, or a substituted or unsubstituted C1 to C30 alkoxy group,
X 2 and X 3 are each independently a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkylamine group, or a substituted or unsubstituted C1 to C30 alkoxy group,
M is CR a , SiR b , N, P, PR c R d , or PR e , wherein R a , R b , R c , and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof, and R e is oxygen (O) or sulfur (S), and
n is an integer ranging from 1 to 4.

2. The monomer as claimed in claim 1 , wherein A 1 is a substituted or unsubstituted cyclic group selected from the following Group 1:

wherein, in Group 1,
Z 1 and Z 2 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, C═O, NR f , oxygen (O), sulfur (S), or a combination thereof, wherein R f is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, or a combination thereof, and
Z 3 to Z 17 are independently C═O, NR g , oxygen (O), sulfur (S), CR h R i , or a combination thereof, wherein R g to R i are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof.

3. The monomer as claimed in claim 1 , wherein X 1 is a hydroxy group.

4. The monomer as claimed in claim 1 , wherein:
A 1 is a substituted or unsubstituted divalent pyrene, benzoperylene, or coronene group,
A 2 to A 4 are each a phenylene group,
X 1 is a hydroxy group, and X 2 to X 3 are each independently a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkylamine group, or a substituted or unsubstituted C1 to C30 alkoxy group,
M is CR a , wherein R a is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof, and
n is 2.

5. The monomer as claimed in claim 1 , wherein the monomer is represented by the following Chemical Formula 2, Chemical Formula 3, or Chemical Formula 4:

wherein, in the above Chemical Formulae 2 to 4,
X a , X b , X c , X d , X e , X g , X h , X i , X j , X k , and X l are each independently a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkylamine group, or a substituted or unsubstituted C1 to C30 alkoxy group.

6. The monomer as claimed in claim 1 , wherein the monomer has a molecular weight of about 300 to about 3,000.

7. A hardmask composition, comprising:
a monomer represented by the following Chemical Formula 1; and
a solvent,

wherein, in the above Chemical Formula 1,
A 1 is a substituted or unsubstituted aliphatic cyclic group or a substituted or unsubstituted aromatic cyclic group,
A 2 to A 4 are each a phenylene group,
X 1 is a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C20 alkylamine group, or a substituted or unsubstituted C1 to C30 alkoxy group,
X 2 and X 3 are each independently a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkylamine group, or a substituted or unsubstituted C1 to C30 alkoxy group,
M is CR a , SiR b , N, P, PR c R d , or PR e , wherein R a , R b , R c , and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof, and R e is oxygen (O) or sulfur (S), and
n is an integer ranging from 1 to 4.
R e is oxygen (O) or sulfur (S).

8. The hardmask composition as claimed in claim 7 , wherein A 1 a substituted or unsubstituted cyclic group selected from the following Group 1:

wherein, in Group 1,
Z 1 and Z 2 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heteroarylene group, a substituted or unsubstituted C2 to C20 alkenylene group, a substituted or unsubstituted C2 to C20 alkynylene group, C═O, NR f , oxygen (O), sulfur (S), or a combination thereof, wherein R f is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, or a combination thereof, and
Z 3 to Z 17 are independently C═O, NR g , oxygen (O), sulfur (S), CR h R i , or a combination thereof, wherein R g to R i are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof.

9. The hardmask composition as claimed in claim 7 , wherein the X 1 is a hydroxy group.

10. The hardmask composition as claimed in claim 7 , wherein:
A 1 is a substituted or unsubstituted divalent pyrene, benzoperylene, or coronene group,
A 2 to A 4 are each a phenylene group,
X 1 is a hydroxy group, and X 2 to X 3 are each independently a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkylamine group, or a substituted or unsubstituted C1 to C30 alkoxy group,
M is CR a , wherein R a is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof, and
n is 2.

11. The hardmask composition as claimed in claim 7 , wherein the monomer is re

Assignees

• Lee Bum-Jin
• Kim Yun-Jun
• Cho Youn-Jin
• Cheil Ind Inc

Inventors

• Lee Bum-Jin
• Kim Yun-Jun
• Cho Youn-Jin

Classifications

• C07C33/36

  Polyhydroxylic alcohols containing six-membered aromatic rings and other rings · CPC title

• G03F7/26 Primary

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

• G03F7/11 Primary

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

• C07C39/04

  Phenol · CPC title

• G03F7/094 Primary

  Multilayer resist systems, e.g. planarising layers · CPC title