Resist composition and pattern forming process

Patent metadata

Field	Value
Publication number	US-11720019-B2
Application number	US-202117157011-A
Country	US
Kind code	B2
Filing date	Jan 25, 2021
Priority date	Feb 27, 2020
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

A resist composition comprising a quencher containing a sulfonium salt having the formula (A).

First claim

The invention claimed is:

1. A resist composition comprising a quencher containing a sulfonium salt having the formula (A):

wherein k, m, and n are each independently an integer of 1 to 3, p is 0 or 1, q is an integer of 0 to 4, r is an integer of 1 to 3,
X BI is iodine or bromine,
R a1 is a C 1 -C 20 (k+1)-valent aliphatic hydrocarbon group which may contain at least one selected from an ether bond, a carbonyl group, an ester bond, an amide bond, a sultone ring, a lactam ring, a carbonate group, a halogen other than iodine, a C 6 -C 12 aryl group, a hydroxyl group, or a carboxyl group,
X 1 is a single bond, an ether bond, an ester bond, an amide bond, a carbonyl group, or a carbonate group,
X 2 is a single bond or a C 1 -C 20 (m+1)-valent hydrocarbon group which may contain at least one selected from an ether bond, a carbonyl group, an ester bond, an amide bond, a sultone ring, a lactam ring, a carbonate group, a halogen other than iodine, a hydroxyl group, or a carboxyl group,
X 3 is a single bond, an ether bond, or an ester bond,
R 1 is a single bond or a C 1 -C 20 saturated hydrocarbylene group which may contain an ether bond, an ester bond, or a hydroxyl group,
R 2 is a C 1 -C 20 hydrocarbyl group which may contain a heteroatom, two R 2 s may be the same or different, and may bond together to form a ring with a sulfur atom to which the two R 2 s are attached when r=1,
R 3 is a hydroxyl group, a carboxyl group, a nitro group, a cyano group, fluorine, chlorine, bromine, iodine, an amino group, or a C 1 -C 20 saturated hydrocarbyl group, C 1 -C 20 saturated hydrocarbyloxy group, C 2 -C 20 saturated hydrocarbylcarbonyloxy group, C 2 -C 20 saturated hydrocarbyloxycarbonyl group, or C 1 -C 4 saturated hydrocarbylsulfonyloxy group which may contain fluorine, chlorine, bromine, iodine, a hydroxyl group, an amino group, or an ether bond, and
Xq − is a halide ion, a sulfonic acid anion not having fluorine at an α-position, a carboxylic acid anion, or a sulfonamide anion.

2. The resist composition of claim 1 , further comprising an organic solvent.

3. The resist composition of claim 1 , further comprising an acid generator capable of generating fluorosulfonic acid, fluoroimidic acid, or fluoromethide acid.

4. The resist composition of claim 1 , further comprising a base polymer.

5. The resist composition of claim 4 , wherein the base polymer comprises recurring units having the formula (a1) or recurring units having the formula (a2):

wherein R A is each independently hydrogen or a methyl group,
Y 1 is a single bond, a phenylene group, a naphthylene group, or a C 1 -C 12 linking group containing at least one selected from an ester bond or a lactone ring,
Y 2 is a single bond or an ester bond,
Y 3 is a single bond, an ether bond, or an ester bond,
R 11 and R 12 are each independently an acid labile group,
R 13 is fluorine, a trifluoromethyl group, a cyano group, a C 1 -C 6 saturated hydrocarbyl group, a C 1 -C 6 saturated hydrocarbyloxy group, a C 2 -C 7 saturated hydrocarbylcarbonyl group, a C 2 -C 7 saturated hydrocarbylcarbonyloxy group, or a C 2 -C 7 saturated hydrocarbyloxycarbonyl group,
R 14 is a single bond or a C 1 -C 6 alkanediyl group in which some carbon may be replaced by an ether bond or an ester bond,
a is 1 or 2, b is an integer of 0 to 4, and 1≤a+b≤5.

6. The resist composition of claim 5 which is a chemically amplified positive resist composition.

7. The resist composition of claim 4 , wherein the base polymer is free of an acid labile group.

8. The resist composition of claim 7 which is a chemically amplified negative resist composition.

9. The resist composition of claim 1 , wherein the base polymer comprises recurring units having any one of the formulae (f1) to (f3):

wherein R A is each independently hydrogen or a methyl group,
Z 1 is a single bond, a C 1 -C 6 aliphatic hydrocarbylene group, a phenylene group, a naphthylene group, a C 7 -C 18 combination thereof, —O—Z 11 —, —C(═))—O—Z 11 —, or —C(═O)—NH—Z 11 —, Z 11 is a C 1 -C 6 aliphatic hydrocarbylene group, a phenylene group, a naphthylene group, or a C 7 -C 18 combination thereof, which may contain a carbonyl group, an ester bond, an ether bond, or a hydroxyl group,
Z 2 is a single bond, —Z 21 —C(═O)—O—, —Z 21 —O—, or —Z 21 —O—C(═O)—, Z 21 is a C 1 -C 12 saturated hydrocarbylene group which may contain a carbonyl group, an ester bond, or an ether bond,
Z 3 is a single bond, a methylene group, an ethylene group, a phenylene group, a fluorinated phenylene group, —O—Z 31 —, —C(═O)—O—Z 31 —, or —C(═O)—NH—Z 31 —, Z 31 is a C 1 -C 6 aliphatic hydrocarbylene group, a phenylene group, a fluorinated phenylene group, or a trifluoromethyl-substituted phenylene group which may contain a carbonyl group, an ester bond, an ether bond, or a hydroxyl group,
R 21 to R 28 are each independently a halogen or a C 1 -C 20 hydrocarbyl group which may contain a heteroatom, a pair of R 23 and R 24 or R 26 and R 27 may bond together to form a ring with a sulfur atom to which they are attached,
R HF is hydrogen or a trifluoromethyl group, and
M − is a non-nucleophilic counter ion.

10. The resist composition of claim 1 , further comprising a surfactant.

11. The resist composition of claim 1 wherein the halide ion is a chloride ion, a bromide ion, or an iodide ion, the sulfonic acid anion not having fluorine at the α-position is represented by the formula (B), the carboxylic acid anion is represented by the formula (C) or (D), and the sulfonamide anion is represented by the formula (E),
R q1 —SO 3 −   (B)

wherein R q1 is hydrogen or a C 1 -C 40 hydrocarbyl group which may contain a heteroatom, exclusive of the hydrocarbyl group in which the hydrogen bonded to the carbon atom at α-position of the sulfo group is substituted by fluorine or a fluoroalkyl group,
R q2 —CO 2 −   (C)

wherein R q2 is a C 1 -C 40 hydrocarbyl group which may contain a heteroatom,

wherein R q3 is hydroxyl, fluorine, chlorine, bromine, amino, nitro, cyano, or a C 1 -C 6 saturated hydrocarbyl, C 1 -C 6 saturated hydrocarbyloxy, C 2 -C 6 saturated hydrocarbylcarbonyloxy, or C 1 -C 4 saturated hydrocarbylsulfonyloxy group, in which some or all hydrogen may be substituted by a halogen, or —N(R q3A )—C(═O)—R q3B , or —N(R q3A )—C(═O)—O—R q3B , R q3A is hydrogen or a C 1 -C 6 saturated hydrocarbyl group, R q3B is a C 1 -C 6 saturated hydrocarbyl or C 2 -C 8 unsaturated aliphatic hydrocarbyl group, x′ is an integer of 1 to 5, y′ is an integer of 0 to 3, z′ is an integer of 1 to 3, and L 1 is a single bond, or a C 1 -C 20 (z′+1)-valent linking group which may contain at least one group selected from an ether bond, a carbonyl group, an ester bond, an amide bond, a sultone ring, a lactam ring, a carbonate group, a halogen, a hydroxyl group, or a carboxyl group,

wherein R q4 is fluorine, a C 1 -C 10 hydrocarbyl group, or a C 1 -C 10 fluorinated hydrocarbyl group, which may contain a hydroxyl group, an ether bond, or an ester bond, R q5 is hydrogen or a C 1 -C 10 hydrocarbyl group which may contain a hydroxyl group, an ether bond, or a

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Watanabe Tomomi

Classifications

• G03F7/0045 Primary

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

• C07C59/115

  containing halogen · CPC title

• C07C61/135

  having three rings · CPC title

• C07C63/70

  Monocarboxylic acids · CPC title

• C07C65/10

  Salicylic acid · CPC title