Coating composition for forming resist underlayer film for EUV lithography process

Patent metadata

Field	Value
Publication number	US-12228858-B2
Application number	US-201816176245-A
Country	US
Kind code	B2
Filing date	Oct 31, 2018
Priority date	Oct 31, 2018
Publication date	Feb 18, 2025
Grant date	Feb 18, 2025

Abstract

A monomer represented by Chemical Formula (1):wherein, X, Y, and Z are the same as described in the specification, and the polymer including repeat units derived from the monomer.

First claim

The invention claimed is:

1. An underlayer coating composition, comprising:
a polymer comprising:
repeat units derived from a monomer represented by Chemical Formula (1):

wherein,
X is a linear or branched C1 to C10 hydrocarbon group, a C1 to C10 alkoxycarbonyl group, a carboxylic acid group, or a linear or branched C1 to C10 hydroxyalkyl group optionally substituted with a C1 to C5 alkoxycarbonyl group or a C1 to C5 substituted alkoxy group;
Y is a hydrogen, a linear or branched C1 to C10 hydrocarbon group, a C1 to C10 alkoxycarbonyl group, a carboxylic acid group, or a linear or branched C1 to C10 hydroxyalkyl group optionally substituted with a C1 to C5 alkoxycarbonyl group or a C1 to C5 alkoxy group; and
Z is a linear or branched C1 to C10 hydrocarbon group, a C1 to C10 alkoxycarbonyl group, a carboxylic acid group, or a linear or branched C1 to C10 hydroxyalkyl group optionally substituted with a C1 to C5 alkoxycarbonyl group or a C1 to C5 alkoxy group,
wherein each of the C1 to C10 hydrocarbon group, the C1 to C10 alkoxycarbonyl group, and the C1 to C10 hydroxyalkyl group is optionally substituted with at least one selected from the group consisting of fluorine, chlorine, bromine, iodine, a hydroxyl group, a thiol group, a carboxylic acid group, a C1 to C5 alkyl group, a C3 to C8 cycloalkyl group, a C2 to C5 alkenyl group, a C1 to C5 alkoxy group, a C2 to C5 alkenoxy group, a C6 to C10 aryl group, a C6 to C10 aryloxy group, a C7 to C10 alkylaryl group, and a C7 to C10 alkylaryloxy group,
provided that at least one selected from X, Y, and Z is:
a linear or branched C1 to C10 hydrocarbon group substituted with at least one selected from the group consisting of a hydroxyl group, a thiol group, a carboxylic acid group, a C2 to C5 alkenyl group, a C1 to C5 alkoxy group, a C2 to C5 alkenoxy group, a C6 to C10 aryloxy group, and a C7 to C10 alkylaryloxy group,
a C1 to C10 alkoxycarbonyl group,
a carboxylic acid group, or
a linear or branched C1 to C10 hydroxyalkyl group optionally substituted with a C1 to C5 alkoxycarbonyl group or a C1 to C5 alkoxy group, and

repeat units derived from a monomer represented by Chemical Formula (3):

wherein,
K, L, and M are each independently a linear or branched C1 to C10 hydrocarbon group, a C1 to C10 alkoxycarbonyl group, a C1 to C10 alkanoyloxy group, each of which is optionally substituted with a carboxylic acid group, or a linear or branched C1 to C10 hydroxyalkyl group optionally substituted with a C1 to C5 alkoxycarbonyl group or a C1 to C5 substituted alkoxy group,
wherein each of the C1 to C10 hydrocarbon group, the C1 to C10 alkoxycarbonyl group, the C1 to C10 alkanoyloxy group, and the C1 to C10 hydroxyalkyl group is optionally substituted with at least one selected from the group consisting of fluorine, chlorine, bromine, iodine, C1 to C5 alkyl, C3 to C8 cycloalkyl, C2 to C5 alkenyl, C1 to C5 alkoxy, C2 to C5 alkenoxy, C6 to C10 aryl, C6 to C10 aryloxy, C7 to C10 alkylaryl, and C7 to C10 alkylaryloxy, and

4 to 15 wt % of a photoacid generator comprising an iodonium cation, based on total solid content of the underlayer coating composition.

2. The underlayer coating composition of claim 1 , further comprising repeat units derived from a monomer represented by Chemical Formula (2):

wherein,
A, B, C, D, E, and F are each independently a hydrogen, a halogen, a hydroxyl group, a carboxylic acid group, a C1 to C10 alkoxycarbonyl group, a C1 to C10 alkoxy group, a linear or branched C1 to C10 hydrocarbon group, or a C1 to C10 alkanoyloxy group,
wherein each of the C1 to C10 alkoxycarbonyl group, the C1 to C10 alkoxy group, the C1 to C10 hydrocarbon group, and the C1 to C10 alkanoyloxy group is optionally substituted with at least one selected from the group consisting of fluorine, chlorine, bromine, iodine, C1 to C5 alkyl, C3 to C8 cycloalkyl, C2 to C5 alkenyl, C1 to C5 alkoxy, C2 to C5 alkenoxy, C6 to C10 aryl, C6 to C10 aryloxy, C7 to C10 alkylaryl, and C7 to C10 alkylaryloxy, and
wherein at least two selected from A, B, C, D, E, and F are independently selected from the group consisting of:
a linear or branched C1 to C10 hydrocarbon group substituted with at least one selected from the group consisting of a hydroxyl group, a carboxylic acid group, a C2 to C5 alkenyl group, a C1 to C5 alkoxy group, a C2 to C5 alkenoxy group, a C6 to C10 aryloxy group, and a C7 to C10 alkylaryloxy group,
a C1 to C10 alkoxy group,
a C1 to C10 alkoxycarbonyl group,
a C1 to C10 alkanoyloxy group,
a carboxylic acid group, or
a hydroxyl group.

3. The underlayer coating composition of claim 1 , wherein in Chemical Formula (1), at least one selected from X, Y, and Z comprises a carboxylic acid group.

4. The underlayer coating composition of claim 2 , wherein in Chemical Formula (2), at least one selected from A, B, C, D, E, and F comprises an iodine.

5. The underlayer coating composition of claim 1 , wherein in Chemical Formula (3), at least one selected from K, L, and M comprises a hydroxyalkyl group.

6. The underlayer coating composition of claim 1 , further comprising:
a crosslinking agent; and
a solvent.

7. A coated substrate comprising:
a layer of the underlayer coating composition of claim 1 disposed on a substrate, and
a photoresist layer disposed on the layer of the underlayer coating composition.

8. A method of forming an electronic device, comprising:
(a) applying a layer of the underlayer coating composition of claim 1 on a substrate;
(b) curing the underlayer coating composition to form an underlayer film;
(c) applying a layer of a photoresist composition on the underlayer film to form a photoresist layer;
(d) pattern-wise exposing the photoresist layer to radiation; and
(e) developing the exposed photoresist layer to provide a resist relief image.

9. The underlayer coating composition of claim 1 , wherein the photoacid generator is selected from:

10. The underlayer coating composition of claim 1 , wherein the monomer represented by Chemical Formula (1) does not comprise an aromatic ring group, a heteroaromatic ring group, or an epoxy group.

11. The underlayer coating composition of claim 1 , wherein Y is not hydrogen.

Assignees

• Rohm & Haas Elect Materials Korea Ltd
• Dupont Specialty Materials Korea Ltd

Inventors

• Sim Jae Hwan
• Kim Suwoong
• Park Jin Hong
• Kim Myung Yeol
• Ghang Yoo-Jin
• Lim Jae-Bong

Classifications

• G03F7/092

  characterised by backside coating or layers, by lubricating-slip layers or means, by oxygen barrier layers or by stripping-release layers or means · 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

• G03F7/30

  Imagewise removal using liquid means · CPC title

• G03F7/0045

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