# US 2019/0377262 A1 · Resist underlayer composition, and method of forming patterns using the composition

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- Number: US 2019/0377262 A1
- Document ID: US20190377262A1
- Status: Published application
- Kind: A1
- Application number: 16/436,140
- Filed: 2019-06-10
- Published: 2019-12-12
- Earliest claimed: 2018-06-11
- Assignees: Samsung SDI Co., Ltd.
- Applicants: Samsung SDI Co., Ltd.
- Inventors: Shinhyo BAE; Soonhyung KWON; Hyeon PARK; Jaeyeol BAEK; Beomjun JOO; Yoojeong CHOI
- Web page: https://patentgrep.com/patent/US20190377262A1

## CPC

- C08G 18/3853: {containing cyanurate and/or isocyanurate groups}
- G03F 7/091: {characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement}
- C08G 18/022: {the polymeric products containing isocyanurate groups}
- C08G 18/3876: {containing mercapto groups}
- C08L 61/06: of aldehydes with phenols
- C08L 61/28: with melamine
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 71/00: Compositions of polyethers obtained by reactions forming an ether link in the main chain (of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06); Compositions of derivatives of such polymers
- C08L 75/04: Polyurethanes
- G03F 7/0041: {providing an etching agent upon exposure (G03F7/075 takes precedence; photolytic halogen compounds G03F7/0295)}
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/094: {Multilayer resist systems, e.g. planarising layers}
- G03F 7/36: Imagewise removal not covered by groups G03F7/30 - G03F7/34, e.g. using gas streams, using plasma
- C08G 73/0644: {Poly(1,3,5)triazines}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A resist underlayer composition and a method of forming patterns using a resist underlayer composition, the resist underlayer composition including a polymer, the polymer including a structural unit that is a reaction product of an isocyanurate compound, the isocyanurate compound having at least one thiol group thereon, and a solvent.

## Claims

### Claim 1

A resist underlayer composition, comprising:
a polymer including a structural unit that is a reaction product of an isocyanurate compound, the isocyanurate compound having at least one thiol group, and
a solvent.

### Claim 2 (depends on 1)

The resist underlayer composition as claimed in claim 1, wherein the isocyanurate compound is represented by Chemical Formula 1:
wherein, in Chemical Formula 1, R1 to R3 are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, provided that at least one of R1 to R3 includes a thiol group substituent.

### Claim 3 (depends on 1)

The resist underlayer composition as claimed in claim 1, wherein the isocyanurate compound is represented by Chemical Formula 1-1:
wherein, in Chemical Formula 1-1,
L1 and L2 are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C1 to C10 heteroalkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, a substituted or unsubstituted C2 to C10 heterocycloalkylene group, a substituted or unsubstituted C6 to C10 arylene group, or a substituted or unsubstituted C1 to C10 heteroarylene group, and
R3 is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 heteroalkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 heterocycloalkyl group, a substituted or unsubstituted C6 to C10 aryl group, or a substituted or unsubstituted C1 to C10 heteroaryl group.

### Claim 4 (depends on 1)

The resist underlayer composition as claimed in claim 1, wherein the structural unit is a reaction product of the isocyanurate compound and a compound having at least one reactive functional group.

### Claim 5 (depends on 4)

The resist underlayer composition as claimed in claim 4, wherein the structural unit is a reaction product of the thiol group of the isocyanurate compound and the at least one reactive functional group of the compound including the at least one reactive functional group.

### Claim 6 (depends on 4)

The resist underlayer composition as claimed in claim 4, wherein the compound including at least one reactive functional group is represented by Chemical Formula 2:
A1-D-A2 [Chemical Formula 2]
wherein, in Chemical Formula 2,
A1 and A2 are each independently a substituted or unsubstituted C1 to C10 alkoxide group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C1 to C10 carbonate group, —C(═O)Ra, or —C(═O)ORa, in which Ra and Rb are each independently hydrogen or a halogen atom, and
D is a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C1 to C30 heteroalkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C1 to C30 heteroarylene group.

### Claim 7 (depends on 6)

The resist underlayer composition as claimed in claim 6, wherein the compound represented by Chemical Formula 2 is a compound represented by one of the following Chemical Formula 2-1 to Chemical Formula 2-4:
wherein, in Chemical Formulae 2-1 to 2-4,
X1 to X4 are each independently C142, 0, or S,
R11 to R14 are each independently a substituted or unsubstituted C1 to C6 alkenyl group,
R15 and R16 are each independently hydrogen or a halogen atom, and
k, l, m, n, o, p, and q are each independently an integer of 0 to 10.

### Claim 8 (depends on 1)

The resist underlayer composition as claimed in claim 1, wherein the structural unit of the polymer is represented by one of the following Chemical Formula 3 to Chemical Formula 6:
wherein, in Chemical Formula 3 to Chemical Formula 6,
X1 to X4 are each independently CH2, O, or S,
L1 and L2 are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C1 to C10 heteroalkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, a substituted or unsubstituted C2 to C10 heterocycloalkylene group, a substituted or unsubstituted C6 to C10 arylene group, or a substituted or unsubstituted C1 to C10 heteroarylene group,
R3 is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 heteroalkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 heterocycloalkyl group, a substituted or unsubstituted C6 to C10 aryl group, or a substituted or unsubstituted C1 to C10 heteroaryl group, and
k, l, m, n, o, p, and q are each independently an integer of 0 to 10.

### Claim 9 (depends on 1)

The resist underlayer composition as claimed in claim 1, wherein the polymer has a weight average molecular weight of about 1,000 to about 100,000.

### Claim 10 (depends on 1)

The resist underlayer composition as claimed in claim 1, wherein the polymer is included in the composition in an amount of about 0.1 wt % to about 30 wt %, based on a total weight of the resist underlayer composition.

### Claim 11 (depends on 1)

The resist underlayer composition as claimed in claim 1, further comprising an additional polymer, the additional polymer including an acryl resin, an epoxy resin, a novolac resin, a glycoluril resin, or a melamine resin.

### Claim 12 (depends on 1)

The resist underlayer composition as claimed in claim 1, further comprising a surfactant, thermal acid generator, a plasticizer, or a combination thereof.

### Claim 13 (depends on 1)

A method of forming patterns, the method comprising:
forming an etching subject layer on a substrate,
coating the resist underlayer composition as claimed in claim 1 on the etching subject layer to form a resist underlayer,
forming a photoresist pattern on the resist underlayer, and
sequentially etching the resist underlayer and the etching subject layer using the photoresist pattern as an etching mask.

### Claim 14 (depends on 13)

The method as claimed in claim 13, wherein forming the photoresist pattern includes:
forming a photoresist layer on the resist underlayer,
exposing the photoresist layer, and
developing the photoresist layer.

### Claim 15 (depends on 14)

The method as claimed in claim 14, wherein forming the resist underlayer further includes heat-treating the coated resist underlayer composition at a temperature of about 100° C. to about 500° C.