Radiation-sensitive resin composition, resist pattern-forming method, acid diffusion control agent, carboxylic acid salt and carboxylic acid

Patent metadata

Field	Value
Publication number	US-11320735-B2
Application number	US-201916552339-A
Country	US
Kind code	B2
Filing date	Aug 27, 2019
Priority date	Mar 1, 2017
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

A radiation-sensitive resin composition contains: a polymer having an acid-labile group, a radiation-sensitive acid generator, a compound represented by the following formula (1), and a solvent. In the formula (1), X represents an oxygen atom or a sulfur atom; R1 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R2 to R5 each independently represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally two or more of R2 to R5 taken together represent an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which the two or more of R2 to R5 bond; Zn+ represents a cation having a valency of n; and n is an integer of 1 to 3.

First claim

What is claimed is:

1. A radiation-sensitive resin composition, comprising:
a solvent;
a polymer comprising an acid-labile group;
a radiation-sensitive acid generator; and
a compound of formula (1),

wherein X is an oxygen atom or a sulfur atom; R 1 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 and R 3 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group-substituted hydrocarbon group, a hydroxy group- and a fluorine atom-substituted hydrocarbon group, or a group comprising an aliphatic heterocyclic structure, or R 2 and R 3 taken together an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond: R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally R 4 and R 5 taken together are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 4 and R 5 bond; Z n+ represents a cation having a valency of n; and n is an integer of 1 to 3.

2. The radiation-sensitive resin composition according to claim 1 , wherein R 1 in the formula (1) is the hydrogen atom.

3. The radiation-sensitive resin composition according to claim 2 , wherein R 2 and R 3 in the formula (1) taken together are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond.

4. The radiation-sensitive resin composition according to claim 2 , wherein R 2 and R 3 in the formula (1) each independently are the group comprising an aliphatic heterocyclic structure, the hydrogen atom, the hydrocarbon group, the hydroxy group-substituted hydrocarbon group, or the hydroxy group- and fluorine atom-substituted hydrocarbon group.

5. The radiation-sensitive resin composition according to claim 2 , wherein R 4 and R 5 in the formula (1) each independently is a hydrogen atom.

6. The radiation-sensitive resin composition according to claim 1 , wherein R 2 and R 3 in the formula (1) taken together are the alicyclic structure having 3 to 20 ring atoms or the aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond.

7. The radiation-sensitive resin composition according to claim 6 , wherein R 4 and R 5 in the formula (1) each independently is a hydrogen atom.

8. The radiation-sensitive resin composition according to claim 1 , wherein R 2 and R 3 in the formula (1) are each independently the group comprising an aliphatic heterocyclic structure, the hydrogen atom, the hydrocarbon group, the hydroxy group-substituted hydrocarbon group, or the hydroxy group- and fluorine atom-substituted hydrocarbon group.

9. The radiation-sensitive resin composition according to claim 8 , wherein R 4 and R 5 in the formula (1) each independently is a hydrogen atom.

10. The radiation-sensitive resin composition according to claim 1 , wherein R 4 and R 5 in the formula (1) is each independently the hydrogen atom.

11. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator generates sulfonic acid upon irradiation with a radioactive ray.

12. A resist pattern-forming method comprising:
applying the radiation-sensitive resin composition of claim 1 directly or indirectly on one face of a substrate to obtain a resist film;
exposing the resist film; and
developing the resist film exposed.

13. An acid diffusion control agent of formula (1′),

wherein X is an oxygen atom or a sulfur atom; R 1 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 and R 3 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group-substituted hydrocarbon group, a hydroxy group- and a fluorine atom-substituted hydrocarbon group, or a group comprising an aliphatic heterocyclic structure, or R 2 and R 3 taken together an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond; R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally R 4 and R 5 taken together are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 4 and R 5 bond; Z n+ is a radiation-sensitive cation having a valency of n; and n is an integer of 1 to 3.

14. A carboxylic acid salt of formula (i),

wherein X is an oxygen atom or a sulfur atom; R 1 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 and R 3 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group-substituted hydrocarbon group, a hydroxy group- and a fluorine atom-substituted hydrocarbon group, or a group comprising an aliphatic heterocyclic structure, or R 2 and R 3 taken together an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 2 and R 3 bond: R 4 and R 5 are each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and optionally R 4 and R 5 taken together represent are an alicyclic structure having 3 to 20 ring atoms or an aliphatic heterocyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 4 and R 5 bond; Z n+ is a radiation-sensitive cation having a valency of n; and n is an integer of 1 to 3.

15. The carboxylic acid salt according to claim 14 , wherein R 2 and R 3 in the formula (i) are each independently the group comprising an aliphatic heterocyclic structure, the hydrogen atom, the hydrocarbon group, the hydroxy group-substituted hydrocarbon group, or the hydroxy group- and fluorine atom-substituted hydrocarbon group.

16. The carboxylic acid salt according to claim 14 , wherein Z n+ in the formula (i) is an onium cation.

17. The carboxylic acid salt according to claim 16 , wherein the onium cation is a sulfonium cation, an iodonium cation, a tetrahydrothiophenium cation or a combination thereof.

18. The carboxylic acid salt according to claim 16 , wherein n in the formula (i) is 2 or 3.

19. The carboxylic acid salt according to claim 14 , wherein
n in the formula (i) is 1, and
Z n+ is an alkali metal cation.

20. A carboxylic acid of formula (i′),

wherein X is an oxygen atom or a sulfur atom; R 1 is a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; R 2 and R 3 are each independently a hydrogen atom, a hydrocarbon group, a hydroxy group-substituted hydrocarbon group, a hydroxy group- and a fluorine atom-substituted hydrocarbon group, or a group comprising an aliphatic heterocyclic structure, or R 2 and R 3 taken together an alicyclic structure having 3 to 20 ring atoms or an ali

Assignees

• Jsr Corp

Inventors

• NISHIKORI Katsuaki
• Okazaki Satoshi

Classifications

• G03F7/2006

  using coherent light; using polarised light · CPC title

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/20

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

• G03F7/0045 Primary

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

• G03F7/325

  Non-aqueous compositions · CPC title