# US 2025/0147415 A1 · Resist composition and method of forming patterns using the same

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- Number: US 2025/0147415 A1
- Document ID: US20250147415A1
- Status: Published application
- Kind: A1
- Application number: 18/635,761
- Filed: 2024-04-15
- Published: 2025-05-08
- Earliest claimed: 2023-11-06
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Sunyoung LEE; Haengdeog KOH; Yoonhyun KWAK; Jiyoun LEE; Kyuhyun IM; Jinwon JEON; Jungha CHAE; Minyoung HA
- Web page: https://patentgrep.com/patent/US20250147415A1

## CPC

- G03F 7/0042: {with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists (G03F7/075 takes precedence)}
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)

## 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 M11, L11 to L14, a11 to a14, R11 to R14, b11 to b14, Y11 to Y13, X11 to X13, Y21, Y22, L21, and a21 in Formulae 1-1 to 1-4 and 2 are described in the specification.

## Claims

### Claim 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,
M11 is indium (In), tin (Sn), antimony (Sb), tellurium (Te), thallium (Tl), lead (Pb), bismuth (Bi), or polonium (Po),
L11 to L14 are each independently a single bond or a linear, branched, or cyclic C1-C30 divalent hydrocarbon group,
a11 to a14 are each independently an integer from 1 to 4, and
R11 to R14 are each independently a substituted or unsubstituted C3-C30 branched alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocycloalkenyl group, a substituted or unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C7-C30 arylalkyl group, a substituted or unsubstituted C1-C30 heteroaryl group, or a substituted or unsubstituted C2-C30 heteroarylalkyl group,
an adjacent two of R11 to R14 are optionally combined with each other to form a condensed ring,
b11 to b14 are each independently an integer from 1 to 4,
Y11 to Y13 are each independently O, O(C═O), S, S(C═O), NX14, or N(C═O),
X11 to X14 are each independently hydrogen, deuterium, or a linear, branched, or cyclic C1-C30 monovalent hydrocarbon group optionally including a heteroatom,
Y21 and Y22 are each independently a linear, branched, or cyclic C1-C30 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,
L21 is a single bond, a double bond, or a linear, branched, or cyclic C1-C30 divalent hydrocarbon group,
a21 is an integer from 1 to 4, and
an adjacent two of Y21, Y22, and L21 are optionally combined with each other to form a condensed ring.

### Claim 2 (depends on 1)

The resist composition of claim 1, wherein
M11 is In, Sn, or Sb.

### Claim 3 (depends on 1)

The resist composition of claim 1, wherein
L11 to L14 are each independently a single bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C3-C30 heterocycloalkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C3-C30 cycloalkenylene group, a substituted or unsubstituted C3-C30 heterocycloalkenylene group, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C1-C30 heteroarylene group.

### Claim 4 (depends on 1)

The resist composition of claim 1, wherein
R11 to R14 are each independently selected from a branched C3-C30 alkyl group, a C3-C30 cycloalkyl group, a C3-C30 heterocycloalkyl group, a C2-C30 alkenyl group, a C3-C30 cycloalkenyl group, a C3-C30 heterocycloalkenyl group, a C2-C30 alkynyl group, a C6-C30 aryl group, a C7-C30 arylalkyl group, a C1-C30 heteroaryl group, and a C2-C30 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 C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C1-C20 halogenated alkoxy group, a C1-C20 halogenated alkylthio group, a C3-C20 cycloalkyl group, a C3-C20 cycloalkoxy group, a C3-C20 cycloalkylthio group, a C6-C20 aryl group, a C1-C20 heteroaryl group, a C6-C20 aryloxy group, a C6-C20 arylthio group, a C1-C20 heteroaryloxy group, a C1-C20 heteroarylthio group, or a combination thereof.

### Claim 5 (depends on 1)

The resist composition of claim 1, wherein
the organometallic compound is represented by one of Formulae 1-1 to 1-3,
Y11 to Y13 are each independently O, O(C═O), S, or S(C═O).

### Claim 6 (depends on 1)

The resist composition of claim 1, wherein
X11 to X14 are each independently selected from: hydrogen; deuterium; and a C1-C30 alkyl group, a C1-C30 halogenated alkyl group, a C1-C30 alkoxy group, a C1-C30 alkylthio group, a C1-C30 halogenated alkoxy group, a C1-C30 halogenated alkylthio group, a C3-C30 cycloalkyl group, a C3-C30 cycloalkoxy group, a C3-C30 cycloalkylthio group, a C3-C30 heterocycloalkyl group, a C2-C30 alkenyl group, a C3-C30 cycloalkenyl group, a C3-C30 heterocycloalkenyl group, a C2-C30 alkynyl group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C6-C30 arylthio group, a C7-C30 arylalkyl group, a C1-C30 heteroaryl group, a C1-C30 heteroaryloxy group, a C1-C30 heteroarylthio group, and a C2-C30 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 C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C1-C20 halogenated alkoxy group, a C1-C20 halogenated alkylthio group, a C3-C20 cycloalkyl group, a C3-C20 cycloalkoxy group, a C3-C20 cycloalkylthio group, a C6-C20 aryl group, a C1-C20 heteroaryl group, a C6-C20 aryloxy group, a C6-C20 arylthio group, a C1-C20 heteroaryloxy group, a C1-C20 heteroarylthio group, or a combination thereof.

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 1)

The resist composition of claim 1, wherein
Y21 is represented by one of Formulae 4-1 to 4-5, and
Y22 is represented by one of Formulae 4-6 to 4-10:
wherein, in Formulae 4-1 to 4-10,
X41 and X44 are each independently N or P,
X42 and X45 are each independently O or S,
X43 and X46 are each independently O, S, N, or P,
Y41 and Y42 are each independently C, S, or P,
A41 is a C1-C30 heterocyclic group including X43 as a ring member,
A42 is a C1-C30 heterocyclic group including X46 as a ring member,
R41 to R44 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 C1-C30 divalent hydrocarbon group,
b41 and b42 are each independently an integer from 1 to 10, and
* indicates a binding site to a neighboring atom.

### Claim 9 (depends on 8)

The resist composition of claim 8, wherein
A41 and A42 are each i) independently a monovalent group derived from a first ring, ii) a monovalent group derived from a condensed ring in which two or more first rings are condensed with each other, or iii) a monovalent group derived from a condensed ring in which one or more first rings are condensed with one or more second rings,
the first ring is tetrahydropyran, dihydropyran, pyrane, tetrahydrothiopyrane, dihydrothiopyrane, thiopyrane, tetrahydrofurane, dihydrofurane, tetrahydrothiophene, dihydrothiophene, piperidine, tetrahydropyridine, dihydropyridine, pyrrolidine, dihydropyrrole, pyrrole, imidazole, pyrazole, furan, thiophene, oxazole, thiazole, pyridine, pyrazine, pyridazine, pyrimidine, or triazine, and
the second ring is cyclopentane, cyclopentadiene, cyclohexane, cyclohexene, cyclohexadiene, benzene, or naphthalene.

### Claim 10 (depends on 8)

The resist composition of claim 8, wherein
Y21 is represented by Formula 4-5, and Y22 is represented by one of Formulae 4-6 to 4-10, or
Y21 is represented by one of Formulae 4-1 to 4-5, and Y22 is represented by Formula 4-10.

### Claim 11 (depends on 1)

The resist composition of claim 1, wherein
L21 is a single bond, a double bond, a substituted or unsubstituted C1-C30 alkylene group, a substituted or unsubstituted C3-C30 cycloalkylene group, a substituted or unsubstituted C3-C30 heterocycloalkylene group, a substituted or unsubstituted C2-C30 alkenylene group, a substituted or unsubstituted C3-C30 cycloalkenylene group, a substituted or unsubstituted C3-C30 heterocycloalkenylene group, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C1-C30 heteroarylene group.

### Claim 12 (depends on 1)

The resist composition of claim 1, wherein
the additive is represented by Formula 2-1:
wherein, in Formula 2-1,
X43 and X46 are each independently O, S, N, or P,
A41 is a C1-C30 heterocyclic group including X43 as a ring member,
A42 is a C1-C30 heterocyclic group including X46 as a ring member,
L21 is a single bond, a double bond, or a linear, branched, or cyclic C1-C30 divalent hydrocarbon group,
a21 is an integer from 1 to 4,
R41 to R44 are each independently a linear, branched, or cyclic C1-C30 divalent hydrocarbon group,
b41 and b42 are each independently an integer from 1 to 10, and
an adjacent two of R41, R43, and L21 are optionally combined with each other to form a condensed ring.

### Claim 13 (depends on 1)

The resist composition of claim 1, wherein
the additive is selected from Group II:

### Claim 14 (depends on 1)

The resist composition of claim 1, wherein
the additive is included in an amount of about 0.1 parts by weight to about 100,000 parts by weight based on 100 parts by weight of the organometallic compound.

### Claim 15 (depends on 1)

The resist composition of claim 1, wherein
the resist composition does not include a photoacid generator.

### Claim 16 (depends on 1)

The resist composition of claim 1, wherein
the resist composition substantially does not include a compound having a molecular weight of 1,000 or more.

### Claim 17 (depends on 1)

A pattern formation method comprising:
forming a resist film by applying the resist composition of claim 1 on a substrate;
exposing at least a portion of the resist film to high energy rays to provide an exposed resist film; and
developing the exposed resist film using a developer.

### Claim 18 (depends on 17)

The pattern formation method of claim 17, wherein
the exposing at least a portion of the resist film is performed by at least one of irradiating deep ultraviolet (DUV) rays, extreme ultraviolet (EUV) rays, or electron beams (EBs).

### Claim 19 (depends on 17)

The pattern formation method of claim 17, wherein
the organometallic compound is subjected to a condensation reaction during the exposing at least the portion of the resist film.

### Claim 20 (depends on 17)

The pattern formation method of claim 17, wherein
the exposed resist film includes an exposed portion and a non-exposed portion, and
in the developing, the non-exposed portion is removed.