Radiation-sensitive resin composition, method of forming resist pattern, and compound

Inventors: Takuhiro Taniguchi (Tokyo, JP); Katsuaki Nishikori (Tokyo, JP); Hayato Namai (Tokyo, JP); Kazuya Kiriyama (Tokyo, JP); Ken Maruyama (Tokyo, JP)

Assignee: JSR CORPORATION

G03F7/0045 C07C303/32 C07C381/12 C08G75/20 G03F7/0392 G03F7/0397

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Quick Facts

Patent No.: US 11,966,161
App. No.: 17/854,048
Granted: Apr 23, 2024
Kind: B2

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Abstract

A radiation-sensitive resin composition includes: a polymer including a structural unit including an acid-labile group; and a compound represented by formula (1). R 1 , R 2 , and R 3 each independently represent a halogen atom, a hydroxy group, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms; X 1 , X 2 , and X 3 each independently represent a group represented by formula (2); a sum of d, e, and f is no less than 1; R 4 represents a hydrocarbon group having 1 to 20 carbon atoms and R 5 represents a hydrocarbon group having 1 to 20 carbon atoms, or R 4 and R 5 taken together represent a heterocyclic structure having 4 to 20 ring atoms, together with the sulfur atom to which R 4 and R 5 bond; n is 0 or 1; A − represents a monovalent sulfonic acid anion; and Y represents —COO—, —OCO—, or —N(R 7 )CO—.

Claims (73)

1. A compound represented by formula (1):

wherein, in the formula (1),

R 1 , R 2 , and R 3 each independently represent a halogen atom, a hydroxy group, a nitro group, or a monovalent organic group having 1 to 20 carbon atoms;

a is an integer of 0 to 7, wherein in a case in which a is no less than 2, a plurality of R 1 s are identical or different from each other;

b is an integer of 0 to 4, wherein in a case in which b is no less than 2, a plurality of R 2 s are identical or different from each other;

c is an integer of 0 to 4, wherein in a case in which c is no less than 2, a plurality of R 3 s are identical or different from each other;

X 1 , X 2 , and X 3 each independently represent a group represented by formula (2);

d is an integer of 0 to 7, wherein in a case in which d is no less than 2, a plurality of X 1 s are identical or different from each other;

e is an integer of 0 to 4, wherein in a case in which e is no less than 2, a plurality of X 2 s are identical or different from each other;

f is an integer of 0 to 4, wherein in a case in which f is no less than 2, a plurality of X 3 s are identical or different from each other,

wherein a sum of d, e, and f is no less than 1, a sum of a and d is no greater than 7, a sum of b and e is no greater than 4, and a sum of c and f is no greater than 4;

R 4 represents a hydrocarbon group having 1 to 20 carbon atoms and having a valency of (b+e+1) and R 5 represents a hydrocarbon group having 1 to 20 carbon atoms and having a valency of (c+f+1), or R 4 and R 5 taken together represent a heterocyclic structure having 4 to 20 ring atoms, together with the sulfur atom to which R 4 and R 5 bond;

n is 0 or 1; and

A − represents a monovalent sulfonic acid anion,

wherein, in the formula (2),

L represents an organic group having 1 to 20 carbon atoms and having a valency of (m+1);

Y represents —COO—, —OCO—, or —N(R 7 )CO—, wherein R 7 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms;

R 6 represents a monovalent organic group-having 1 to 20 carbon atoms, which is a lactone ring group, a sultone ring group, a carbonate ring group, an alcoholic hydroxyl group-containing alicyclic hydrocarbon group, a phenolic hydroxyl group-containing group, or an amide group;

m is an integer of 1 to 5, wherein in a case in which m is no less than 2, a plurality of Ys are identical or different and a plurality of R 6 s are identical or different; and

* denotes a site of bonding to a part other than the group represented by the formula (2) in the compound.

2. The compound according to claim 1 , wherein n in the formula (1) is 0.

3. The compound according to claim 1 , wherein L in the formula (2) represents a hydrocarbon group having 1 to 20 carbon atoms and having a valency of (m+1).

4. A radiation-sensitive resin composition comprising:

a polymer comprising a structural unit comprising an acid-labile group; and

the compound according to claim 1 .

5. The radiation-sensitive resin composition according to claim 4 , wherein n in the formula (1) is 0.

6. The radiation-sensitive resin composition according to claim 4 , wherein L in the formula (2) represents a hydrocarbon group having 1 to 20 carbon atoms and having a valency of (m+1).

7. A method of forming a resist pattern, the method comprising:

applying a radiation-sensitive resin composition directly or indirectly on a substrate to form a resist film;

exposing the resist film; and

developing the resist film exposed,

wherein the radiation-sensitive resin composition comprises:

a polymer comprising a structural unit comprising an acid-labile group; and

the compound according to claim 1 .

8. The method according to claim 7 , wherein n in the formula (1) is 0.

9. The method according to claim 7 , wherein L in the formula (2) represents a hydrocarbon group having 1 to 20 carbon atoms and having a valency of (m+1).

10. A compound represented by formula (1):