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-10345706-B2
Application number	US-201414258489-A
Country	US
Kind code	B2
Filing date	Apr 22, 2014
Priority date	Jun 26, 2013
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

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, wherein the monomer is represented by Chemical Formula 1a, 1c to 1k, or 1n to 1o:

wherein, in the above Chemical Formulae 1a, 1c, and 1d,
X a , X b , X e , X f , X g , X h , X i and X j are independently a hydroxy group, a halogen atom, a halogen-containing 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 C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C20 aldehyde group, a substituted or unsubstituted C1 to C4 alkyl ether, a substituted or unsubstituted C7 to C20 arylalkylene ether, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C1 to C20 alkylborane group, a substituted or unsubstituted C6 to C30 arylborane group, or a combination thereof,
Z e is a single bond, a substituted or unsubstituted C1 or C3 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, oxygen (O), sulfur (S), or a combination thereof,
Z g is 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, oxygen (O), sulfur (S), or a combination thereof,
Z a , Z b , and Z f are independently nitrogen (N), CR, or a combination thereof, and
R is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, a halogen-containing group, or a combination thereof,

wherein, in the above Chemical Formulae 1 e to 1k,
X a to X y are each independently a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a halogen atom, a halogen-containing group, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof, and
Z h and Z i 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, oxygen (O), sulfur (S), or a combination thereof:

wherein, in the above Chemical Formulae 1n and 1o,
X i to X o are each independently a hydroxy group, a halogen atom, a halogen-containing 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 C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C20 aldehyde group, a substituted or unsubstituted C1 to C4 alkyl ether, a substituted or unsubstituted C7 to C20 arylalkylene ether, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C1 to C20 alkylborane group, a substituted or unsubstituted C6 to C30 arylborane group, or a combination thereof.

2. The monomer for a hardmask composition as claimed in claim 1 , wherein the monomer has a molecular weight of about 200 to about 5,000.

3. A hardmask composition, comprising:
the monomer as claimed in claim 1 ; and
a solvent.

4. The hardmask composition as claimed in claim 3 , wherein the monomer has a molecular weight of about 200 to about 5,000.

5. The hardmask composition as claimed in claim 3 , wherein the monomer is included in an amount of about 0.1 to about 50 wt % based on the total amount of the hardmask composition.

6. A method of forming a pattern, the method comprising:
providing a material layer on a substrate,
applying the hardmask composition of claim 3 on the material layer,
heat-treating the hardmask composition to form a hardmask layer,
forming a silicon-containing thin layer on the hardmask layer,
forming a photoresist layer on the silicon-containing thin layer,
exposing and developing the photoresist layer to form a photoresist pattern, and
selectively removing the silicon-containing thin layer and the hardmask layer using the photoresist pattern to expose a part of the material layer, and
etching an exposed part of the material layer.

7. The method as claimed in claim 6 , wherein the hardmask composition is applied using a spin-on coating method.

8. The method as claimed in claim 6 , wherein forming the hardmask layer includes heat-treating at about 100° C. to about 500° C.

9. The method as claimed in claim 6 , further comprising forming a bottom antireflective coating (BARC) on the silicon-containing thin layer.

10. The method as claimed in claim 9 , wherein the silicon-containing thin layer includes silicon oxynitride (SiON).

Assignees

• Song Hyun Ji
• Kim Yun Jun
• Kim Go Un
• Kim Young Min
• Kim Hea Jung
• Moon Joon Young
• Park Yo Choul
• Park Yu Shin
• Park You Jung
• Shin Seung Wook
• Yoon Yong Woon
• Lee Chung Heon
• Choi Yoo Jeong
• Hong Seung Hee
• Cheil Ind Inc

Inventors

• Song Hyun-Ji
• Kim Yun-Jun
• Kim Go-Un
• Kim Young-Min
• Kim Hea-Jung
• Moon Joon-Young
• Park Yo-Choul
• Park Yu-Shin
• Park You-Jung
• Shin Seung-Wook
• Yoon Yong-Woon
• Lee Chung-Heon
• Choi Yoo-Jeong
• Hong Seung-Hee

Classifications

• C07D333/50

  condensed with carbocyclic rings or ring systems · CPC title

• C07C39/225

  with at least one hydroxy group on a condensed ring system · CPC title

• G03F7/091

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

• G03F7/38

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

• C07C2603/54

  containing more than five condensed rings · CPC title