Polymer, hardmask composition, and method of forming patterns

Patent metadata

Field	Value
Publication number	US-11220570-B2
Application number	US-201916724777-A
Country	US
Kind code	B2
Filing date	Dec 23, 2019
Priority date	Dec 26, 2018
Publication date	Jan 11, 2022
Grant date	Jan 11, 2022

Abstract

A polymer, a hardmask composition, and a method of forming patterns, the polymer including structural units obtained by a reaction of a reaction mixture that includes a substituted or unsubstituted indole compound, a first aromatic aldehyde compound including a substituted or unsubstituted C3 to C20 branched alkyl group thereon, and a second aromatic aldehyde compound that is different from the first aromatic aldehyde compound.

First claim

What is claimed is:

1. A polymer comprising structural units obtained by a reaction of a reaction mixture that includes:
a substituted or unsubstituted indole compound,
a first aromatic aldehyde compound including a substituted or unsubstituted C3 to C20 branched alkyl group thereon, and
a second aromatic aldehyde compound that is different from the first aromatic aldehyde compound.

2. The polymer as claimed in claim 1 , wherein the indole compound is represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Z 1 is hydrogen, a hydroxy group, a halogen atom, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
Z 2 and Z 3 are independently a hydroxy group, a halogen atom, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
m is an integer of 0 to 4, and
n is an integer of 0 to 2.

3. The polymer as claimed in claim 1 , wherein the substituted or unsubstituted C3 to C20 branched alkyl group is a substituted or unsubstituted tert-butyl group.

4. The polymer as claimed in claim 1 , wherein the first aromatic aldehyde compound includes a substituted or unsubstituted aromatic ring moiety of Group 1:

5. The polymer as claimed in claim 1 , wherein the first aromatic aldehyde compound is a benzaldehyde substituted with a C3 to C20 branched alkyl group, a naphthaldehyde substituted with a C3 to C20 branched alkyl group, an anthracenecarboxaldehyde substituted with a C3 to C20 branched alkyl group, or a pyrenecarboxaldehyde substituted with a C3 to C20 branched alkyl group.

6. The polymer as claimed in claim 1 , wherein the second aromatic aldehyde compound includes a substituted or unsubstituted aromatic ring moiety of Group 2:

7. The polymer as claimed in claim 1 , wherein the second aromatic aldehyde compound includes a C6 to C30 aromatic ring substituted at least one hydroxy group.

8. The polymer as claimed in claim 1 , wherein at least one of the first aromatic aldehyde compound and the second aromatic aldehyde compound includes a condensed ring.

9. The polymer as claimed in claim 1 , wherein:
the first aromatic aldehyde compound is a benzaldehyde substituted with a C3 to C20 branched alkyl group, a naphthaldehyde substituted with a C3 to C20 branched alkyl group, an anthracenecarboxaldehyde substituted with a C3 to C20 branched alkyl group, or a pyrenecarboxaldehyde substituted with a C3 to C20 branched alkyl group, and
the second aromatic aldehyde compound is a substituted or unsubstituted pyrenecarboxaldehyde.

10. The polymer as claimed in claim 1 , wherein:
the indole compound is included in the reaction mixture in an amount of about 1 mol % to about 50 mol %,
the first aromatic aldehyde compound is included in the reaction mixture in an amount of about 1 mol % to about 80 mol %, and
the second aromatic aldehyde compound is included in the reaction mixture in an amount of about 1 mol % to about 80 mol %, all mol % being based on a total number of moles of the indole compound, the first aromatic aldehyde compound, and the second aromatic aldehyde compound in the reaction mixture.

11. A hardmask composition, comprising:
the polymer as claimed in claim 1 , and
a solvent.

12. A method of forming patterns, the method comprising:
applying the hardmask composition as claimed in claim 11 on a material layer and heat-treating the same to form a hardmask layer,
forming a photoresist layer on the hardmask layer,
exposing and developing the photoresist layer to form a photoresist pattern,
selectively removing the hardmask layer using the photoresist pattern to expose a portion of the material layer, and
etching the exposed portion of the material layer.

Assignees

• Samsung Sdi Co Ltd

Inventors

• Park Soyeon
• Kim Youngmin
• Yoo Yongsik

Classifications

• C08G12/26 Primary

  with heterocyclic compounds · CPC title

• G03F7/11

  having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• G03F7/094 Primary

  Multilayer resist systems, e.g. planarising layers · CPC title

• C09D161/26

  of aldehydes with heterocyclic compounds · CPC title