Radiation-sensitive resin composition and resist pattern-forming method

Patent metadata

Field	Value
Publication number	US-11609495-B2
Application number	US-202017081000-A
Country	US
Kind code	B2
Filing date	Oct 27, 2020
Priority date	Oct 28, 2019
Publication date	Mar 21, 2023
Grant date	Mar 21, 2023

Abstract

A radiation-sensitive resin composition includes a polymer including a phenolic hydroxyl group, a compound represented by formula (1-1) or formula (1-2), and a compound represented by formula (2). In the formula (1-1), a sum of a, b, and c is no less than 1; at least one of R 1 , R 2 , and R 3 represents a fluorine atom or the like; and R 4 and R 5 each independently represent a hydrogen atom, a fluorine atom, or the like. In the formula (1-2), in a case in which d is 1, R 6 represents a fluorine atom or the like, and in a case in which d is no less than 2, at least one of the plurality of R 6 s represents a fluorine atom or the like; and R 8 represents a single bond or a divalent organic group having 1 to 20 carbon atoms.

First claim

What is claimed is:

1. A radiation-sensitive resin composition comprising:
a polymer comprising a first structural unit represented by at least one formula selected from the group consisting of formula (I-1), formula (I-2), formula (I-3), formula (I-4), formula (I-5), formula (I-6), formula (I-7), formula (I-8), formula (I-9), formula (I-10), formula (I-11), formula (I-12), formula (I-13), and formula (I-14) and a second structural unit comprising an acid-labile group which is dissociated by an action of an acid to give a carboxy group;
a first compound represented by formula (1-1) or formula (1-2); and
a second compound represented by formula (2):

wherein
in each of the formulae (I-1) to (I-14), R P represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group,

wherein
in each of the formula (1-1) and the formula (1-2), A − represents a monovalent sulfonic acid anion,
in the formula (1-1), a is an integer of 0 to 11, b is an integer of 0 to 4, and c is an integer of 0 to 4, wherein a sum of a, b, and c is no less than 1; R 1 , R 2 , and R 3 each independently represent a hydroxy group, a nitro group, a halogen atom, or a monovalent organic group having 1 to 20 carbon atoms, wherein at least one of R 1 , R 2 , and R 3 represents a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 10 carbon atoms, in a case in which a is no less than 2, a plurality of R 1 s are identical or different, in a case in which b is no less than 2, a plurality of R 2 s are identical or different, and in a case in which c is no less than 2, a plurality of R 3 s are identical or different; ni is 0 or 1; and R 4 and R 5 each independently represent a hydrogen atom, a fluorine atom, or a monovalent fluorinated hydrocarbon group having 1 to 10 carbon atoms, or R 4 and R 5 taken together represent a single bond,
in the formula (1-2), d is an integer of 1 to 11 and e is an integer of 0 to 10, wherein in a case in which d is 1, R 6 represents a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 10 carbon atoms, and in a case in which d is no less than 2, a plurality of R 6 s are identical or different, and each R 6 represents a hydroxy group, a nitro group, a halogen atom, or a monovalent organic group having 1 to 20 carbon atoms, wherein at least one of the plurality of R 6 s represents a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 10 carbon atoms; R 7 represents a hydroxy group, a nitro group, a halogen atom, or a monovalent organic group having 1 to 20 carbon atoms, wherein in a case in which e is no less than 2, a plurality of R 7 s are identical or different; R 8 represents a single bond or a divalent organic group having 1 to 20 carbon atoms; n 2 is 0 or 1; and n 3 is an integer of 0 to 3, and
R 9 —COO − X +   (2)

in the formula (2), R 9 represents a monovalent organic group having 1 to 30 carbon atoms; and X + represents a monovalent radiation-sensitive onium cation, and
wherein a molar amount of the first structural unit relative to a total molar amount of structural units constituting the polymer is 25 mol % or more, and a molar amount of the second structural unit relative to the total molar amount of the structural units constituting the polymer is 30 mol % or more.

2. The radiation-sensitive resin composition according to claim 1 , wherein the monovalent sulfonic acid anion comprises a ring structure.

3. The radiation-sensitive resin composition according to claim 2 , wherein the ring structure is at least one selected from a norbornane structure, an adamantane structure, and a sultone structure.

4. The radiation-sensitive resin composition according to claim 2 , wherein the ring structure is an aromatic ring structure comprising at least one iodine atom as a substituent.

5. The radiation-sensitive resin composition according to claim 2 , wherein the ring structure comprises a steroid skeleton or a 9,10-ethanoanthracene skeleton.

6. The radiation-sensitive resin composition according to claim 1 , wherein the monovalent sulfonic acid anion comprises a partial structure represented by formula (3),

wherein
in the formula (3), R 10 and R 11 each independently represent a hydrogen atom, a fluorine atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms, wherein at least one of R 10 and R 11 represents a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms; m is an integer of 1 to 10, wherein in a case in which m is no less than 2, a plurality of R 10 s are identical or different and a plurality of R 11 s are identical or different; and * denotes a binding site to a part other than the partial structure represented by the formula (3) in the monovalent sulfonic acid anion.

7. The radiation-sensitive resin composition according to claim 6 , wherein in the formula (3), R 10 and R 11 each independently represent a fluorine atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms, wherein at least one of R 10 and R 11 represents a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms; m is an integer of 2 to 10, wherein a plurality of R 10 s are identical or different and a plurality of R 11 s are identical or different.

8. The radiation-sensitive resin composition according to claim 1 , wherein the second structural unit is represented by formula (4-1), formula (4-2), or formula (4-3),

wherein
in each of the formulae (4-1) to (4-3), each R T independently represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group,
in the formula (4-1), R X represents a monovalent hydrocarbon group having 1 to 20 carbon atoms; and R Y and R Z each independently represent a monovalent hydrocarbon group having 1 to 20 carbon atoms, or R Y and R Z taken together represent an alicyclic structure having 3 to 20 ring atoms, together with the carbon atom to which R Y and R z bond, in the formula (4-2), R A represents a hydrogen atom; R B and R C each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms; and R D represents a divalent hydrocarbon group having 1 to 20 carbon atoms constituting an unsaturated alicyclic structure having 4 to 20 ring atoms together with the carbon atom to which each of R A , R B , and R C bonds, and
in the formula (4-3), R U and R V each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and R W represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, and R U and R V optionally taken together represent an alicyclic structure having 3 to 20 ring atoms, together with the carbon atom to which R U and R V bond, and R U and R W optionally taken together represent an alicyclic heterocyclic structure having 5 to 20 ring atoms, together with the carbon atom to which R U bonds and the oxygen

Assignees

• Jsr Corp

Inventors

• NISHIKORI Katsuaki
• Kiriyama Kazuya
• Taniguchi Takuhiro
• Maruyama Ken

Classifications

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• G03F7/0392

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

• C07D327/04

  Five-membered rings · CPC title

• C07D317/70 Primary

  condensed with ring systems containing two or more relevant rings · CPC title

• C07C381/12

  Sulfonium compounds · CPC title