Method for forming pattern using antireflective coating composition including photoacid generator

Patent metadata

Field	Value
Publication number	US-11269252-B2
Application number	US-201916517950-A
Country	US
Kind code	B2
Filing date	Jul 22, 2019
Priority date	Jul 22, 2019
Publication date	Mar 8, 2022
Grant date	Mar 8, 2022

Abstract

An antireflective coating composition, including a polymer, a photoacid generator having a crosslinkable group, a compound capable of crosslinking the polymer and the photoacid generator, a thermal acid generator, and an organic solvent.

First claim

The invention claimed is:

1. An antireflective coating composition, comprising:
a polymer, wherein the polymer comprises a cyanurate structural unit,
a photoacid generator comprising a crosslinkable group,
a compound capable of crosslinking the polymer and the photoacid generator,
a thermal acid generator, and
an organic solvent,
wherein the photoacid generator is an onium salt having G + A − formula wherein G + has Formula 1 and A − is a non-polymerizable organic anion:

wherein, in Formula 1,
Y is I or S,
each R 1 is independently a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-30 cycloalkyl group, a substituted or unsubstituted polycyclic or monocyclic C 6-30 aryl group, wherein when Y is S, one of the R 1 is optionally attached to one adjacent R 1 by a single bond or a linking group,
provided that at least one R 1 is a monocyclic C 6-30 aryl group bearing a hydroxyl group attached thereto through a single bond or an unsubstituted or substituted C 1 -C 30 linking group optionally including at least one heteroatom selected from O, S, N, and P, and
z is 2 or 3, wherein when Y is I, z is 2, or when Y is S, z is 3.

2. The antireflective coating composition of claim 1 , wherein G + is represented by Formula 2:

wherein, in Formula 2,
each R a is independently hydrogen, halogen, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted C 2-30 alkenyl group, a substituted or unsubstituted C 2-30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group,
each R b is a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-30 cycloalkyl group, a substituted or unsubstituted polycyclic or monocyclic C 6-30 aryl group, wherein groups R b are optionally attached to each other by a single bond or a linking group,
each L is a single bond, a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 2 -C 30 alkynylene group, a substituted or unsubstituted C 3 -C 30 cycloalkenylene group, a substituted or unsubstituted C 3 -C 30 cycloalkynylene group, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 6 -C 30 heteroarylene group, in each of which groups at least one non-adjacent —CH 2 — group is optionally replaced by —SO 2 —, —C(═O)—, —O—, —S—, —SO—, —C(═O)O—, —OC(═O)—, —C(═O)NR—, or —NRC(═O)—, wherein R is hydrogen or a C 1 -C 10 alkyl group, or a combination thereof;
n1 is an integer from 1 to 5, and
n2 is an integer from 0 to 4,
provided that the sum of n1 and n2 does not exceed 5.

3. The antireflective coating composition of claim 1 , wherein G + is represented by Formula 3:

wherein, in Formula 3,
each R a is hydrogen, a halogen, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted C 2-30 alkenyl group, a substituted or unsubstituted C 2-30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, wherein groups R a are optionally attached to each other by a single bond or a linking group,
R b is independently a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted polycyclic or monocyclic C 3-30 cycloalkyl group, a substituted or unsubstituted polycyclic or monocyclic C 6-30 aryl group,
each L is a single bond, a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 2 -C 30 alkynylene group, a substituted or unsubstituted C 3 -C 30 cycloalkenylene group, a substituted or unsubstituted C 3 -C 30 cycloalkynylene group, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 6 -C 30 heteroarylene group, in each of which groups at least one non-adjacent —CH 2 — group is optionally replaced by —SO 2 —, —C(═O)—, —O—, —S—, —SO—, —C(═O)O—, —OC(═O)—, —C(═O)NR—, or —NRC(═O)—, wherein R is hydrogen or a C 1 -C 10 alkyl group, or a combination thereof;
each n1 is an integer from 1 to 5,
each n2 is an integer from 0 to 4, and
provided that each sum of n1 and n2 does not exceed 5.

4. The antireflective coating composition of claim 1 , wherein G + is represented by Formula 4:

wherein, in Formula 4,
each R a is hydrogen, a halogen, a cyano group, a nitro group, an amino group, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted C 2-30 alkenyl group, a substituted or unsubstituted C 2-30 alkynyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group,
each L is a single bond, a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 2 -C 30 alkynylene group, a substituted or unsubstituted C 3 -C 30 cycloalkenylene group, a substituted or unsubstituted C 3 -C 30 cycloalkynylene group, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 6 -C 30 heteroarylene group, in each of which groups at least one non-adjacent —CH 2 — group is optionally replaced by —SO 2 —, —C(═O)—, —O—, —S—, —SO—, —C(═O)O—, —OC(═O)—, —C(═O)NR—, or —NRC(═O)—, wherein R is hydrogen or a C 1 -C 10 alkyl group, or a combination thereof;
each n1 is an integer from 1 to 5,
each n2 is an integer from 0 to 4, and
provided that each sum of n1 and n2 does not exceed 5.

5. The antireflective coating composition of claim 1 , wherein the cyanurate structural unit is derived from a compound represented by Formula 5:

wherein, in Formula 5,
R 2 , R 3 , R 4 , and each X are independently hydrogen, a substituted or unsubstituted C 1-30 alkyl group, a substituted or unsubstituted C 2-30 alkenyl group, a substituted or unsubstituted C 2-30 alkynyl group, a substituted or unsubstituted C 2-30 alkanoyl group, a substituted or unsubstitut

Assignees

• Rohm & Haas Elect Materials Korea Ltd
• Rohm & Haas Elect Mat

Inventors

• Lee Jung-June
• Ahn Jae-Yun
• Sim Jae-Hwan
• Lim Jae-Bong
• Aqad Emad
• Kim Myung-Yeol

Classifications

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/004 Primary

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

• C08G73/0655

  from polycyanurates · CPC title

• C08G12/427

  Melamine · CPC title

• G03F7/091 Primary

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