Resist compound, method for forming pattern using same, and method for manufacturing semiconductor device using same

Patent metadata

Field	Value
Publication number	US-12560865-B2
Application number	US-202217890409-A
Country	US
Kind code	B2
Filing date	Aug 18, 2022
Priority date	Feb 19, 2020
Publication date	Feb 24, 2026
Grant date	Feb 24, 2026

Abstract

Provided are a resist compound, a method of forming a pattern by using the same, and a method of manufacturing a semiconductor device using the same. According to the present disclosure, the compound may be represented by Formula 1:

First claim

The invention claimed is:

1 . A compound represented by Formula 1:

wherein, in Formula 1,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently one selected from hydrogen, deuterium, and a C 1 -C 3 alkyl,
R 10 is a single bond, a linear C 1 -C 11 alkyl, or a branched C 1 -C 11 alkyl,
R 20 is a C 2 -C 11 perhalogenated alkyl or a C 2 -C 11 perhalogenated alkyl ether perhalogenated alkyl,
X is one selected from H, F, Cl, Br, and I,
n is an integer from 10 to 150, and
wherein a total number of Sn is equal to a total number of R 20 .

2 . The compound of claim 1 , wherein, in Formula 1,
R 20 is represented by C b X 2b O Z , wherein X is one selected from F and I, b is an integer from 2 to 11, and z is an integer selected from 0, 1, 2, and 3.

3 . The compound of claim 1 , wherein, in Formula 1, the C 2 -C 11 perhalogenated alkyl or the C 2 -C 11 perhalogenated alkyl ether perhalogenated alkyl in R 20 is a C 2 -C 11 perfluoroalkyl or a C 2 -C 11 perflouroalkyl ether perflouroalkyl.

4 . The compound of claim 1 , wherein the compound represented by Formula 1 comprises a compound represented by Formula 2:

wherein, in Formula 2,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently one selected from hydrogen, deuterium, and a C 1 -C 3 alkyl,
X is one selected from F, Cl, Br, and I,
a is an integer selected from 0 to 11,
b is an integer selected from 2 to 11,
z is an integer selected from 0, 1, 2, and 3, and
n is an integer from 10 to 150.

5 . The compound of claim 4 , wherein
in Formula 2, X is F.

6 . The compound of claim 1 , wherein the compound represented by Formula 1 comprises a compound represented by Formula 3 or a compound represented by Formula 4:

wherein, in Formula 3, n is an integer from 10 to 150,

wherein, in Formula 4, n is an integer from 10 to 150.

7 . The compound of claim 6 , wherein
the compound represented by Formula 1 comprises the compound represented by Formula 3.

8 . The compound of claim 6 , wherein the compound represented by Formula 1 comprises the compound represented by Formula 4.

9 . A method of forming a pattern, the method comprising:
forming a film using the compound of claim 1 ; and patterning the film.

10 . A method of manufacturing a semiconductor device, the method comprising:
forming a resist film by coating a substrate with a compound represented by Formula 1; and patterning the resist film,

wherein, in Formula 1,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently one selected from hydrogen, deuterium, and a C 1 -C 3 alkyl,
R 10 is a single bond, a linear C 1 -C 11 alkyl, or a branched C 1 -C 11 alkyl,
R 20 is C 2 -C 11 perhalogenated alkyl or C 2 -C 11 perhalogenated alkyl ether perhalogenated alkyl,
X is one selected from H, F, Cl, Br, and I,
n is an integer from 10 to 150,
wherein a total number of Sn is equal to a total number of R 20 .

11 . The method of claim 10 , wherein, in Formula 1,
R 20 is represented by C b X 2b O Z , X is one selected from F and I, b is an integer from 2 to 11, and z is an integer selected from 0, 1, 2, and 3.

12 . The method of claim 10 , wherein, in Formula 1, the C 2 -C 11 perhalogenated alkyl or the C 2 -C 11 perhalogenated alkyl ether perhalogenated alkyl in R 20 is a C 2 -C 11 perfluoroalkyl, and X is F.

13 . The method of claim 12 , wherein the patterning of the resist film comprises:
irradiating a light on the resist film; and removing a portion of the resist film using a developing solution, wherein the light includes an electron beam or an extreme ultraviolet ray, and the developing solution includes a highly fluorinated solution.

14 . The method of claim 10 , wherein the compound represented by Formula 1 comprises a compound represented by Formula 2:

wherein, in Formula 2,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently one selected from hydrogen, deuterium, and a C 1 -C 3 alkyl,
X is one selected from F and I,
a is an integer selected from 0 to 11,
b is an integer selected from 2 to 11,
z is an integer selected from 0, 1, 2, and 3, and
n is an integer from 10 to 150.

15 . The method of claim 14 , wherein
in Formula 2, X is F.

16 . The method of claim 14 , wherein the compound represented by Formula 2 comprises a compound represented by Formula 3:

wherein, in Formula 3, n is an integer from 10 to 150.

17 . The method of claim 14 , wherein the compound represented by Formula 2 comprises a compound represented by Formula 4:

wherein, in Formula 4, n is an integer from 10 to 150.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Lee Jin Kyun
• Oh Hyun Taek

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• H10P50/71

  using masks for conductive or resistive materials · CPC title

• C08F230/04

  containing a metal · CPC title

• C08F222/402 Primary

  Alkyl substituted imides · CPC title

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title