Polymer, resist composition including the same, and method of forming pattern using the resist composition

Patent metadata

Field	Value
Publication number	US-2024124635-A1
Application number	US-202318164841-A
Country	US
Kind code	A1
Filing date	Feb 6, 2023
Priority date	Sep 23, 2022
Publication date	Apr 18, 2024
Grant date	—

Abstract

Provided are a polymer, a resist composition including the same, and a method of forming a pattern using the resist composition, the polymer including one or more of a first repeating unit represented by Formula 1 and a second repeating unit represented by Formula 2, and free of a repeating unit of which a structure changes by an acid:In Formulae 1 and 2, R11 to R16, b12, X−, R21 to R24, b22, and Y are as described in the specification.

First claim

What is claimed is:

1 . A polymer comprising:
at least one of a first repeating unit represented by Formula 1 or a second repeating unit represented by Formula 2, and being free of a repeating unit of which a structure changes by an acid:

wherein, in Formulae 1 and 2,
R 11 and R 21 are each independently hydrogen, deuterium, halogen, a C 1 -C 6 linear or branched alkyl group, or a halogenated C 1 -C 6 linear or branched alkyl group;
R 12 to R 14 and R 22 to R 24 are each independently hydrogen, deuterium, halogen, or a linear, branched, or cyclic monovalent C 1 -C 20 hydrocarbon group optionally containing a heteroatom;
b12 and b22 are each independently integers of 1 to 4;
R 15 and R 16 are each independently a linear, branched, or cyclic monovalent C 1 -C 20 hydrocarbon group optionally containing a heteroatom, and R 15 and R 16 optionally bond together to form a ring;
X − is a counter ion;
Y is at least one of a halogen, R 18 SO 3 , R 18 CO 2 , R 18 PO 4 , or NO 3 ;
R 18 is a linear, branched, or cyclic monovalent C 1 -C 20 hydrocarbon group optionally containing a heteroatom; and
* and *′ are each a bonding site with a neighboring atom.

2 . The polymer of claim 1 , wherein R 12 to R 14 and R 22 to R 24 are each independently hydrogen, deuterium, halogen, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkoxy group, or a C 6 -C 20 aryl group.

3 . The polymer of claim 1 , wherein
R 13 is one of hydrogen or deuterium; and Rio is hydrogen, deuterium, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkoxy group, or a C 6 -C 20 aryl group, and R 23 is one of hydrogen or deuterium; and R 24 is one of hydrogen, deuterium, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkoxy group, or a C 6 -C 20 aryl group.

4 . The polymer of claim 1 , wherein R 15 and R 16 are each independently a substituted or unsubstituted C 1 -C 20 alkyl group or a substituted or unsubstituted C 3 -C 20 carbocyclic group, and R 15 and R 16 optionally bond together to form a ring.

5 . The polymer of claim 1 , wherein R 15 and R 16 are each independently
a C 1 -C 10 alkyl group unsubstituted or substituted with at least one of halogen, a hydroxy group, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkoxy group, or a C 6 -C 10 aryl group; or a C 6 -C 20 aryl group unsubstituted or substituted with at least one of halogen, a hydroxy group, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, and a C 3 -C 6 cycloalkoxy group, and R 15 and R 16 optionally bond together to form a ring.

6 . The polymer of claim 1 , wherein

is represented by at least one of Formulae 3-1 to 3-3 below:

wherein, in Formulae 3-1 to 3-3,
L31 and L32 are each independently a single bond, 0, S, CO, SO, SO 2 , CRR′, or NR;
R and R′ are each independently hydrogen, deuterium, halogen, a hydroxyl group, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, or a C 3 -C 6 cycloalkoxy group;
X 31 and X 32 are each independently hydrogen, halogen, a C 1 -C 6 alkyl group, or a halogenated C 1 -C 6 alkyl group;
b31 is an integer of 1 to 8,
b32 is an integer of 1 to 5, and
b33 is an integer of 1 to 4.

7 . The polymer of claim 1 , wherein
X − is a halogen ion, R 17 SO 3 − , R 17 CO 2 − , R 17 PO 4 − , PF 6 − , or BF 4 − , and R 17 is a C 1 -C 10 alkyl group unsubstituted or substituted with at least one of halogen, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkoxy group, and a C 6 -C 10 aryl group; or a C 6 -C 20 aryl group unsubstituted or substituted with at least one of halogen, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, or a C 3 -C 6 cycloalkoxy group.

8 . The polymer of claim 1 , wherein Rib is a C 1 -C 10 alkyl group unsubstituted or substituted with at least one of halogen, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkoxy group, and a C 6 -C 10 aryl group; or a C 6 -C 20 aryl group unsubstituted or substituted with at least one of halogen, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, or a C 3 -C 6 cycloalkoxy group.

9 . The polymer of claim 1 , wherein the first repeating unit is represented by Formula 1-1; and the second repeating unit is represented by Formula 2-1:

10 . The polymer of claim 1 , further comprising:
a third repeating unit represented by Formula 4:

wherein, in Formula 4,
R 41 is hydrogen, deuterium, halogen, a linear or branched C 1 -C 6 alkyl group, or a linear or branched halogenated C 1 -C 6 alkyl group,
L 41 is a single bond, a substituted or unsubstituted C 1 -C 10 alkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 3 -C 10 heterocycloalkylene group, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, *—O—*′, *—C(═O)O—*′, —OC(═O)—*′, *—C(═O)NH—*′, −NHC(═O)—*′, or any combination thereof,
a41 is an integer of 1 to 6, and
X 41 is a non-acid labile group.

11 . The polymer of claim 10 , wherein X 41 is hydrogen or a linear, branched, or cyclic monovalent C 1 -C 20 hydrocarbon group containing at least one polar moiety selected from among a hydroxy group, halogen, a cyano group, a carbonyl group, a carboxyl group, *—O—*′, *—C(═O)O—*′, —OC(═O)—*′, *—S(═O)O—*′, —OS(═O)—*′, a lactone ring, a sultone ring, and a carboxylic anhydride moiety.

12 . The polymer of claim 10 , wherein X 41 is represented by any one of Formulae 5-1 to 5-5:

wherein, in Formulae 5-1 to 5-5,
a51 is 1 or 2;
R 51 to R 59 are each independently a bonding site with a neighboring atom, hydrogen, a hydroxy group, halogen, a cyano group, a C 1 -C 6 alkyl group, a halogenated C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkoxy group, or a C 6 -C 10 aryl group,
one of R 51 to R 53 , one of R 54 , one of R 55 , one of R 56 and R 57 , and one of R 58 and R 59 are each a bonding site with a neighboring atom,
b51 is an integer of 1 to 4,
b52 is wan integer of 1 to 10,
b53 and b54 are each independently integers of 1 to 8, and
b55 is a

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kim Minsang
• Koh Haengdeog
• Kwak Yoonhyun
• Kim Beomseok
• Ahn Chanjae
• Chae Jungha
• Choi Sungwon

Classifications

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title

• G03F7/2004 Primary

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/0045

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

• G03F7/004

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

• C08F220/18

  with acrylic or methacrylic acids · CPC title