Polymer, organic layer composition and method of forming patterns

Patent metadata

Field	Value
Publication number	US-11512162-B2
Application number	US-201916509804-A
Country	US
Kind code	B2
Filing date	Jul 12, 2019
Priority date	Jul 18, 2018
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

A polymer, an organic layer composition including the polymer, and a method of forming a pattern using the organic layer composition, the polymer including a reaction product of a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2:(CHO)n1—Ar1—X—Ar2—(CHO)n2  [Chemical Formula 1]wherein, in Chemical Formula 1, X is O, S, or NR, in which R is a hydrogen, or a substituted or unsubstituted C1 to C30 alkyl group, Ar1 and Ar2 are independently a substituted or unsubstituted C6 to C30 aromatic ring group, and n1 and n2 are independently an integer of 1 to 3;Ar3—(OH)m  [Chemical Formula 2]wherein, in Chemical Formula 2, Ar3 is a substituted or unsubstituted C10 to C30 fused aromatic ring group in which at least two rings are fused, and m is an integer of 1 to 3.

First claim

What is claimed is:

1. A polymer comprising a reaction product of a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2:
(CHO) n1 —Ar 1 —X—Ar 2 —(CHO) n2   [Chemical Formula 1]

wherein, in Chemical Formula 1,
X is O, S, or NR, in which R is a hydrogen, or a substituted or unsubstituted C1 to C30 alkyl group,
Ar 1 and Ar 2 are independently a substituted or unsubstituted C6 to C30 aromatic ring group, and
n1 and n2 are independently an integer of 1 to 3;
Ar 3 —(OH) m   [Chemical Formula 2]

wherein, in Chemical Formula 2,
Ar 3 is a substituted or unsubstituted C10 to C30 fused aromatic ring group in which at least two rings are fused, and
m is an integer of 1 to 3.

2. The polymer as claimed in claim 1 , wherein Ar 1 and Ar 2 are independently a substituted or unsubstituted C10 to C30 fused aromatic ring group in which at least two rings are fused.

3. The polymer as claimed in claim 2 , wherein Ar 1 and Ar 2 are independently a substituted or unsubstituted C14 fused aromatic ring group in which three rings are fused, a substituted or unsubstituted C16 to C18 fused aromatic ring group in which four rings are fused, or a combination thereof.

4. The polymer as claimed in claim 1 , wherein the first compound is unsubstituted or is substituted with a hydroxy group or a C1 to C5 alkoxy group.

5. The polymer as claimed in claim 1 , wherein n1 and n2 are both 1.

6. The polymer as claimed in claim 1 , wherein the first compound is represented by Chemical Formula 1-1 or Chemical Formula 1-2:

wherein, in Chemical Formula 1-1 and 1-2,
X is O, S, or NR, in which R is a hydrogen, or a substituted or unsubstituted C1 to C30 alkyl group, and
R 1 to R 15 are independently hydrogen, a hydroxy group, or a C1 to C5 alkoxy group.

7. The polymer as claimed in claim 1 , wherein the first compound is a compound of Group 1:

8. The polymer as claimed in claim 1 , wherein Ar 3 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a combination thereof.

9. The polymer as claimed in claim 1 , wherein a weight average molecular weight of the polymer is about 1,500 to about 4,000.

10. An organic layer composition, comprising:
the polymer as claimed in claim 1 , and
a solvent.

11. The organic layer composition as claimed in claim 10 , wherein Ar 1 and Ar 2 are independently a substituted or unsubstituted C10 to C30 fused aromatic ring group in which at least two rings are fused.

12. The organic layer composition as claimed in claim 11 , wherein Ar 1 and Ar 2 are independently a substituted or unsubstituted C14 fused aromatic ring group in which three rings are fused, a substituted or unsubstituted C16 to C18 fused aromatic ring group in which four rings are fused, or a combination thereof.

13. The organic layer composition as claimed in claim 10 , wherein the first compound is unsubstituted or is substituted with a hydroxy group or a C1 to C5 alkoxy group.

14. The organic layer composition as claimed in claim 10 , wherein n1 and n2 are both 1.

15. The organic layer composition as claimed in claim 10 , wherein the first compound is represented by Chemical Formula 1-1 or Chemical Formula 1-2:

wherein, in Chemical Formula 1-1 and 1-2,
X is O, S, or NR, in which R is a hydrogen, or a substituted or unsubstituted C1 to C30 alkyl group, and
R 1 to R 15 are independently hydrogen, a hydroxy group, or a C1 to C5 alkoxy group.

16. The organic layer composition as claimed in claim 10 , wherein the first compound is a compound of Group 1:

17. The organic layer composition as claimed in claim 10 , wherein Ar 3 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a combination thereof.

18. The organic layer composition as claimed in claim 10 , wherein a weight average molecular weight of the polymer is about 1,500 to about 4,000.

19. A method of forming patterns, the method comprising:
providing a material layer on a substrate,
applying the organic layer composition as claimed in claim 10 on the material layer,
heat-treating the organic layer composition 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 part of the material layer, and
etching an exposed part of the material layer.

Assignees

• Samsung Sdi Co Ltd

Inventors

• Kim Sunghwan
• Park Yushin
• Jung Hyeonil

Classifications

• C08G16/0212 Primary

  with acyclic or carbocyclic organic 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

• C09D161/06

  of aldehydes with phenols · CPC title

• C08G8/04 Primary

  of aldehydes · CPC title

• C08G16/0231

  containing nitrogen · CPC title