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

Patent metadata

Field	Value
Publication number	US-11720022-B2
Application number	US-202016788467-A
Country	US
Kind code	B2
Filing date	Feb 12, 2020
Priority date	Feb 12, 2019
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

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

First claim

What is claimed is:

1. A compound represented by Formula 1 below:

wherein in Formula 1, A 1 , A 2 , A 3 , A 4 , A 5 , A 6 A 7 , A 8 , and A 9 are each independently one of hydrogen, deuterium, and an alkyl group having 1 to 5 carbon atoms, B 1 , B 2 , and B 3 are each independently one of hydrogen, deuterium, and an alkyl group having 1 to 5 carbon atoms, Z is one of hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, and a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, and R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently comprise one of deuterium, a halogen-substituted alkyl group having 3 to 20 carbon atoms, an alkenyl group having 3 to 20 carbon atoms, a silyl group having 1 to 10 carbon atoms, a carbonyl group having 2 to 10 carbon atoms, and a halogen-substituted hydrocarbon ring having 5 to 20 carbon atoms; provided that when at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is comprise a carbonyl group having 2 to 10 carbon atoms, Z is a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms.

2. The compound of claim 1 , wherein in the Formula 1, at least one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 is represented by Formula 2 below:

wherein in Formula 2, X 1 , X 2 , and X 3 each independently comprise one of halogen elements, R 10 comprises perhalogenated alkyl having 1 to 18 carbon atoms or perhalogenated alkyl ether halogenated alkyl having 1 to 18 carbon atoms.

3. The compound of claim 2 , wherein the material represented by the Formula 2 comprises at least one of the materials represented by Formula 2-1, Formula 2-2, and Formula 2-3:

4. The compound of claim 2 , wherein in the Formula 1, another one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 is represented by Formula 3, Formula 4, or Formula 5:

wherein in Formula 3, R 31 , R 32 , R 33 , R 34 , and R 35 are each independently one selected from hydrogen, deuterium, and an alkyl group having 1 to 3 carbon atoms,
in Formula 4, R 41 , R 42 , and R 43 are each independently one selected from hydrogen, deuterium, and an alkyl group having 1 to 3 carbon atoms, and
in Formula 5, R 51 , R 52 , R 53 , R 54 , and R 55 are each independently one selected from hydrogen, deuterium, and an alkyl group having 1 to 3 carbon atoms.

5. The compound of claim 1 , wherein in the Formula 1, Z is represented by Formula Z:

wherein in Formula Z, R 7 and R 8 are each independently one of hydrogen, deuterium, a halogen-substituted alkyl group having 3 to 20 carbon atoms, an alkenyl group having 3 to 20 carbon atoms, a silyl group having 1 to 10 carbon atoms, and a carbonyl group having 1 to 10 carbon atoms, A 10 , A 11 , and A 12 are each independently one of hydrogen, deuterium, and an alkyl group having 1 to 5 carbon atoms, and B 4 is independently hydrogen, deuterium, or an alkyl group having 1 to 5 carbon atoms.

6. The compound of claim 5 , wherein in the Formula 1, at least one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 is represented by Formula 6:

wherein in Formula 6, R 60 is a single bond or an alkyl group having 1 to 3 carbon atoms, and R 61 is an alkyl group having 1 to 10 carbon atoms.

7. The compound of claim 6 , wherein in the Formula 1, Z is one of hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, and a substituted or unsubstituted aromatic ring having 5 to 15 carbon atoms.

8. The compound of claim 1 , wherein in the Formula 1, at least one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 is represented by Formula 7:

wherein in Formula 7, X 10 , X 11 , X 12 , X 13 , and Y each independently comprise one of halogen, substituted or unsubstituted alkyl having 1 to 5 carbon atoms, and a substituted or unsubstituted alkenyl group having 1 to 5 carbon atoms.

9. The compound of claim 8 , wherein in the Formula 7, X 10 , X 11 , X12, and X 13 each independently comprise one of halogen elements, and Y comprises halogen, substituted or unsubstituted alkyl having 1 to 5 carbon atoms, or an alkenyl group having 1 to 5 carbon atoms.

10. The compound of claim 1 , wherein in the Formula 1, at least one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 comprises one selected from the materials represented by Formulas 7-1, 7-2, 7-3, and 7-4:

11. The compound of claim 1 , wherein the compound has a glass transition temperature of about 100° C. to about 180° C.

12. A method for forming a pattern, the method comprising:
applying a compound represented by Formula 1 on a substrate to form a resist layer, and
patterning the resist layer,

wherein in Formula 1, A 1 , A 2 , A 3 , A 4 , A 5 , A 6 A 7 , A 8 , and A 9 are each independently one of hydrogen, deuterium, and an alkyl group having 1 to 5 carbon atoms, B 1 , B 2 , and B 3 are each independently one of hydrogen, deuterium, and an alkyl group having 1 to 5 carbon atoms, Z is one of hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms, and a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, and R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently comprise one of deuterium, a halogen-substituted alkyl group having 3 to 20 carbon atoms, an alkenyl group having 3 to 20 carbon atoms, a silyl group having 1 to 10 carbon atoms, a carbonyl group having 2 to 10 carbon atoms, and a halogen-substituted hydrocarbon ring having 5 to 20 carbon atoms; provided that when at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is comprise a carbonyl group having 2 to 10 carbon atoms, Z is a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms.

13. The method of claim 12 , wherein at least one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 in the Formula 1 comprises perhalogenated alkyl having 1 to 20 carbon atoms or perhalogenated alkyl ether halogenated alkyl having 1 to 20 carbon atoms.

14. The method of claim 13 , wherein another one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 in the Formula 1 comprises an alkenyl group having 3 to 20 carbon atoms.

15. The method of claim 12 , wherein the patterning of the resist layer comprises:
irradiating light on the resist layer; and
using a developing solution to remove a portion of the resist layer,
wherein the light comprises electron beams or extreme ultraviolet rays, and
the developing solution comprises a high fluorine-based solution.

16. The method of claim 12 , wherein in the Formula 1, at least one of R 1 , R 2 , R 3 , R 4 , R 5 , or R 6 is represented by Formula 2:

wherein in Formula 2, X 1 , X 2 , and X 3 are each independently halogen, and R 10 is perhal

Assignees

• Univ Inha Res & Business Found
• Samsung Electronics Co Ltd

Inventors

• Lee Jin-Kyun
• Oh Hyun-Taek
• Jung Seok-Heon
• Mun Jeong-Seok

Classifications

• G03F7/0392 Primary

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• G03F7/2004

  characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title