Resist underlayer composition, and method of forming patterns using the composition

Patent metadata

Field	Value
Publication number	US-11698587-B2
Application number	US-201916436140-A
Country	US
Kind code	B2
Filing date	Jun 10, 2019
Priority date	Jun 11, 2018
Publication date	Jul 11, 2023
Grant date	Jul 11, 2023

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.

First claim

What is claimed is:

1. A resist underlayer composition, comprising:
a polymer including a structural unit that is a reaction product of an isocyanurate compound and a compound having at least one reactive functional group, and
a solvent,
wherein:
the isocyanurate compound is represented by Chemical Formula 1:

in Chemical Formula 1, R 1 to R 3 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 R 1 to R 3 includes a thiol group substituent,
the compound having at least one reactive functional group is represented by one of the following Chemical Formula 2-1 to Chemical Formula 2-4:

in Chemical Formulae 2-1 to 2-4,
X 1 to X 4 are each independently CH 2 , O, or S,
R 11 to R 14 are each independently a substituted or unsubstituted C1 to C6 alkenyl group,
R 15 and R 16 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.

2. The resist underlayer composition as claimed in claim 1 , wherein the isocyanurate compound represented by Chemical Formula 1 is represented by Chemical Formula 1-1:

wherein, in Chemical Formula 1-1,
L 1 and L 2 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
R 3 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.

3. 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,
X 1 to X 4 are each independently CH 2 , O, or S,
L 1 and L 2 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,
R 3 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.

4. 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.

5. 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.

6. 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.

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

8. 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.

9. The method as claimed in claim 8 , wherein forming the photoresist pattern includes:
forming a photoresist layer on the resist underlayer,
exposing the photoresist layer, and
developing the photoresist layer.

10. The method as claimed in claim 9 , 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.

11. The resist underlayer composition as claimed in claim 1 , wherein the polymer has a weight average molecular weight of 2,200 to 100,000.

Assignees

• Samsung Sdi Co Ltd

Inventors

• Bae Shinhyo
• Kwon Soonhyung
• Park Hyeon
• Baek Jaeyeol
• Joo Beomjun
• Choi Yoojeong

Classifications

• C08G18/022

  the polymeric products containing isocyanurate groups · CPC title

• C08L61/28

  with melamine · CPC title

• G03F7/0045

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

• C08L75/04

  Polyurethanes · CPC title

• G03F7/36

  Imagewise removal not covered by groups G03F7/30 - G03F7/34, e.g. using gas streams, using plasma · CPC title