Resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-2018239249-A1
Application number	US-201815891633-A
Country	US
Kind code	A1
Filing date	Feb 8, 2018
Priority date	Feb 20, 2017
Publication date	Aug 23, 2018
Grant date	—

Abstract

A resist composition comprising a base polymer and a quencher in the form of an iodonium salt of fluorinated aminobenzoic acid, fluorinated nitrobenzoic acid or fluorinated hydroxybenzoic acid offers a high dissolution contrast and minimal LWR independent of whether it is of positive or negative tone.

First claim

1 . A resist composition comprising a base polymer and a quencher containing an iodonium salt having the formula (A):

wherein R 1 is a nitro group, hydroxyl group or a group having the formula (A-1) below, R 2 is fluorine or trifluoromethyl, R 3 is methyl or cyano, R 4 is hydroxyl, halogen, trifluoromethyl, nitro, carboxyl, a C 2 -C 10 acyl group, C 2 -C 10 acyloxy group, C 2 -C 10 alkoxycarbonyl group, a straight, branched or cyclic C 1 -C 12 alkyl group which may contain oxo, a straight, branched or cyclic C 2 -C 12 alkenyl group which may contain oxo, a straight, branched or cyclic C 1 -C 12 alkoxy group, C 6 -C 20 aryl group, or C 7 -C 12 aralkyl or aryloxyalkyl group, R 5 is an optionally substituted phenyl group having the formula (A-2) below or an optionally substituted ethynyl group having the formula (A-3) below, m is an integer of 1 to 4, n is an integer of 0 to 3, and p is an integer of 0 to 5,

wherein R 6 and R 7 are each independently hydrogen or a straight, branched or cyclic C 1 -C 6 alkyl group, R 6 and R 7 may bond together to form a ring with the nitrogen atom to which they are attached, which ring may contain an ether bond,
R 8 is hydroxyl, halogen, trifluoromethyl, nitro, carboxyl, a C 2 -C 10 acyl group, C 2 -C 10 acyloxy group, C 2 -C 10 alkoxycarbonyl group, a straight, branched or cyclic C 1 -C 12 alkyl group which may contain oxo, a straight, branched or cyclic C 2 -C 12 alkenyl group which may contain oxo, a straight, branched or cyclic C 1 -C 12 alkoxy group, C 6 -C 20 aryl group, or C 7 -C 12 aralkyl or aryloxyalkyl group,
R 9 is hydrogen, hydroxyl, halogen, trifluoromethyl, nitro, carboxyl, a C 2 -C 10 acyl group, C 2 -C 10 acyloxy group, C 2 -C 10 alkoxycarbonyl group, a straight, branched or cyclic C 1 -C 12 alkyl group which may contain oxo, a straight, branched or cyclic C 2 -C 12 alkenyl group which may contain oxo, a straight, branched or cyclic C 1 -C 12 alkoxy group, C 6 -C 20 aryl group, or C 7 -C 12 aralkyl or aryloxyalkyl group, and q is an integer of 0 to 5.

2 . The resist composition of claim 1 , further comprising an acid generator capable of generating a sulfonic acid, imide acid or methide acid.

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

4 . The resist composition of claim 1 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 methyl, X 1 is a single bond, phenylene group, naphthylene group, or C 1 -C 12 linking group containing an ester moiety and/or lactone ring, X 2 is a single bond or ester group, R 11 and R 12 each are an acid labile group.

5 . The resist composition of claim 4 , further comprising a dissolution inhibitor.

6 . The resist composition of claim 4 which is a chemically amplified positive resist composition.

7 . The resist composition of claim 1 wherein the base polymer is free of an acid labile group.

8 . The resist composition of claim 7 , further comprising a crosslinker.

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

10 . The resist composition of claim 1 wherein the base polymer further comprises recurring units of at least one type selected from the formulae (f1) to (f3):

wherein R A is each independently hydrogen or methyl,
Z 1 is a single bond, phenylene group, —O—Z 11 — or —C(═O)—Z 12 —Z 11 —, Z 11 is a straight, branched or cyclic C 1 -C 6 alkylene or C 2 -C 6 alkenylene group which may contain a carbonyl, ester, ether or hydroxy moiety, or phenylene group, Z 12 is —O— or —NH—,
R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 and R 28 are each independently a straight, branched or cyclic C 1 -C 12 alkyl group which may contain a carbonyl, ester or ether moiety, or C 6 -C 12 aryl group or C 7 -C 20 aralkyl group, in which at least one hydrogen may be substituted by a C 1 -C 10 straight, branched or cyclic alkyl moiety, halogen, trifluoromethyl, cyano, nitro, hydroxyl, mercapto, C 1 -C 10 straight, branched or cyclic alkoxy moiety, C 2 -C 10 straight, branched or cyclic alkoxycarbonyl moiety, or C 2 -C 10 straight, branched or cyclic acyloxy moiety, R 23 and R 24 , or R 26 and R 27 may bond together directly or via a methylene moiety or ether bond to form a ring with the sulfur atom to which they are attached,
Z 2 is a single bond, —Z 21 —C(═O)—O—, —Z 21 —O— or —Z 21 —O—C(═O)—, Z 21 is a straight, branched or cyclic C 1 -C 12 , alkylene group which may contain a carbonyl, ester or ether moiety,
Z 3 is a single bond, methylene group, ethylene group, phenylene group, fluorinated phenylene group, —O—Z 31 —, or —C(═O)—Z 32 —Z 31 —, Z 31 is a straight, branched or cyclic C 1 -C 6 alkylene group or C 2 -C 6 alkenylene group which may contain a carbonyl, ester, ether, fluorine or hydroxyl moiety, or a phenylene, fluorinated phenylene or trifluoromethyl-substituted phenylene group, Z 32 is —O— or —NH—,
A 1 is hydrogen or trifluoromethyl, and
M − is a non-nucleophilic counter ion.

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

12 . A process for forming a pattern comprising the steps of applying the resist composition of claim 1 onto a substrate, baking to form a resist film, exposing the resist film to high-energy radiation, and developing the exposed film in a developer.

13 . The process of claim 12 wherein the high-energy radiation is ArF excimer laser radiation of wavelength 193 nm or KrF excimer laser radiation of wavelength 248 nm.

14 . The process of claim 12 wherein the high-energy radiation is electron beam or extreme ultraviolet radiation of wavelength 3 to 15 nm.

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Ohashi Masaki

Classifications

• G03F7/0397

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

• G03F7/0382

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

• G03F7/0046

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

• G03F7/0392 Primary

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

• G03F7/0045

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