Resist composition and method of forming patterns using the same

Patent metadata

Field	Value
Publication number	US-2025147415-A1
Application number	US-202418635761-A
Country	US
Kind code	A1
Filing date	Apr 15, 2024
Priority date	Nov 6, 2023
Publication date	May 8, 2025
Grant date	—

Abstract

Provided are a resist composition and a pattern formation method using the same. The resist composition may include an organometallic compound represented by one of Formulae 1-1 to 1-4, and an additive represented by Formula 2:

wherein M 11 , L 11 to L 14 , a11 to a14, R 11 to R 14 , b11 to b14, Y 11 to Y 13 , X 11 to X 13 , Y 21 , Y 22 , L 21 , and a21 in Formulae 1-1 to 1-4 and 2 are described in the specification.

First claim

What is claimed is:

1 . A resist composition comprising:
an organometallic compound represented by one of Formulae 1-1 to 1-4; and an additive represented by Formula 2,

wherein, in Formulae 1-1 to 1-4 and 2,
M 11 is indium (In), tin (Sn), antimony (Sb), tellurium (Te), thallium (Tl), lead (Pb), bismuth (Bi), or polonium (Po),
L 11 to L 14 are each independently a single bond or a linear, branched, or cyclic C 1 -C 30 divalent hydrocarbon group,
a11 to a14 are each independently an integer from 1 to 4, and
R 11 to R 14 are each independently a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 3 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 3 -C 30 cycloalkenyl group, a substituted or unsubstituted C 3 -C 30 heterocycloalkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, or a substituted or unsubstituted C 2 -C 30 heteroarylalkyl group,
an adjacent two of R 11 to R 14 are optionally combined with each other to form a condensed ring,
b11 to b14 are each independently an integer from 1 to 4,
Y 11 to Y 13 are each independently O, O(C═O), S, S(C═O), NX 14 , or N(C═O),
X 11 to X 14 are each independently hydrogen, deuterium, or a linear, branched, or cyclic C 1 -C 30 monovalent hydrocarbon group optionally including a heteroatom,
Y 21 and Y 22 are each independently a linear, branched, or cyclic C 1 -C 30 monovalent hydrocarbon group containing, as a heteroatom, at least one selected from an oxygen atom, a sulfur atom, a nitrogen atom and a phosphorus atom,
L 21 is a single bond, a double bond, or a linear, branched, or cyclic C 1 -C 30 divalent hydrocarbon group,
a21 is an integer from 1 to 4, and
an adjacent two of Y 21 , Y 22 , and L 21 are optionally combined with each other to form a condensed ring.

2 . The resist composition of claim 1 , wherein
M 11 is In, Sn, or Sb.

3 . The resist composition of claim 1 , wherein
L 11 to L 14 are each independently a single bond, a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 3 -C 30 cycloalkylene group, a substituted or unsubstituted C 3 -C 30 heterocycloalkylene group, a substituted or unsubstituted C 2 -C 30 alkenylene group, a substituted or unsubstituted C 3 -C 30 cycloalkenylene group, a substituted or unsubstituted C 3 -C 30 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 30 arylene group, or a substituted or unsubstituted C 1 -C 30 heteroarylene group.

4 . The resist composition of claim 1 , wherein
R 11 to R 14 are each independently selected from a branched C 3 -C 30 alkyl group, a C 3 -C 30 cycloalkyl group, a C 3 -C 30 heterocycloalkyl group, a C 2 -C 30 alkenyl group, a C 3 -C 30 cycloalkenyl group, a C 3 -C 30 heterocycloalkenyl group, a C 2 -C 30 alkynyl group, a C 6 -C 30 aryl group, a C 7 -C 30 arylalkyl group, a C 1 -C 30 heteroaryl group, and a C 2 -C 30 heteroarylalkyl group, each unsubstituted or substituted with deuterium, a halogen atom, a cyano group, a nitro group, a hydroxy group, a thiol group, an amino group, a carboxylate group, an ether moiety, a thioether moiety, a carbonyl moiety, an ester moiety, a phosphonate moiety, a sulfonate moiety, a carbonate moiety, an amide moiety, a lactone moiety, a sultone moiety, a carboxylic anhydride moiety, a C 1 -C 20 alkyl group, a C 1 -C 20 halogenated alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a C 1 -C 20 halogenated alkoxy group, a C 1 -C 20 halogenated alkylthio group, a C 3 -C 20 cycloalkyl group, a C 3 -C 20 cycloalkoxy group, a C 3 -C 20 cycloalkylthio group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, a C 6 -C 20 aryloxy group, a C 6 -C 20 arylthio group, a C 1 -C 20 heteroaryloxy group, a C 1 -C 20 heteroarylthio group, or a combination thereof.

5 . The resist composition of claim 1 , wherein
the organometallic compound is represented by one of Formulae 1-1 to 1-3, Y 11 to Y 13 are each independently O, O(C═O), S, or S(C═O).

6 . The resist composition of claim 1 , wherein
X 11 to X 14 are each independently selected from: hydrogen; deuterium; and a C 1 -C 30 alkyl group, a C 1 -C 30 halogenated alkyl group, a C 1 -C 30 alkoxy group, a C 1 -C 30 alkylthio group, a C 1 -C 30 halogenated alkoxy group, a C 1 -C 30 halogenated alkylthio group, a C 3 -C 30 cycloalkyl group, a C 3 -C 30 cycloalkoxy group, a C 3 -C 30 cycloalkylthio group, a C 3 -C 30 heterocycloalkyl group, a C 2 -C 30 alkenyl group, a C 3 -C 30 cycloalkenyl group, a C 3 -C 30 heterocycloalkenyl group, a C 2 -C 30 alkynyl group, a C 6 -C 30 aryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, a C 7 -C 30 arylalkyl group, a C 1 -C 30 heteroaryl group, a C 1 -C 30 heteroaryloxy group, a C 1 -C 30 heteroarylthio group, and a C 2 -C 30 heteroarylalkyl group, each unsubstituted or substituted with deuterium, a halogen atom, a cyano group, a nitro group, a hydroxy group, a thiol group, an amino group, a carboxylate group, an ether moiety, a thioether moiety, a carbonyl moiety, an ester moiety, a phosphonate moiety, a sulfonate moiety, a carbonate moiety, an amide moiety, a lactone moiety, a sultone moiety, a carboxylic anhydride moiety, a C 1 -C 20 alkyl group, a C 1 -C 20 halogenated alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a C 1 -C 20 halogenated alkoxy group, a C 1 -C 20 halogenated alkylthio group, a C 3 -C 20 cycloalkyl group, a C 3 -C 20 cycloalkoxy group, a C 3 -C 20 cycloalkylthio group, a C 6 -C 20 aryl group, a C 1 -C 20 heteroaryl group, a C 6 -C 20 aryloxy group, a C 6 -C 20 arylthio group, a C 1 -C 20 heteroaryloxy group, a C 1 -C 20 heteroarylthio group, or a combination thereof.

7 . The resist composition of claim 1 , wherein
the organometallic compound represented by one of Formulae 1-1 to 1-4 is selected from Group I:

wherein n in Group I is an integer from 1 to 4.

8 . The resist composition of claim 1 , wherein
Y 21 is represented by one of Formulae 4-1 to 4-5, and Y 22 is represented by one of Formulae 4-6 to 4-10:

wherein, in Formulae 4-1 to 4-10,
X 41 and X 44 are each independently N or P,
X 42 and X 45 are each independently O or S,
X 43 and X 46 are each independently O, S, N, or P,
Y 41 and Y 42 are each independently C, S, or P,
A 41 is a C 1 -C 30 heterocyclic group including X 43 as a ring member,
A 42 is a C 1 -C 30 heterocyclic group including X 46 as a ring member,
R 41 to R 44 are each independently hydrogen, deuterium, a halogen atom, a cyano group, a nitro group, a hydroxy group, a thiol group, an amino group, a carboxylate group, or a linear, branched, or cyclic C 1 -C 30 divalent hydrocarbon group,
b41 and b42 are each independent

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Sunyoung
• Koh Haengdeog
• Kwak Yoonhyun
• Lee Jiyoun
• Im Kyuhyun
• Jeon Jinwon
• Chae Jungha
• Ha Minyoung

Classifications

• Y10S430/1055

  Radiation sensitive composition or product or process of making · CPC title

• G03F7/32

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

• G03F7/2004

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

• G03F7/004

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

• G03F7/0042 Primary

  with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists (G03F7/075 takes precedence) · CPC title