Resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-10606172-B2
Application number	US-201815920746-A
Country	US
Kind code	B2
Filing date	Mar 14, 2018
Priority date	Mar 17, 2017
Publication date	Mar 31, 2020
Grant date	Mar 31, 2020

Abstract

A resist composition comprising a base polymer and a quencher in the form of an iodonium salt capable of generating fluorobenzoic acid bonded to iodized benzene offers a high sensitivity and minimal LWR independent of whether it is of positive or negative tone.

First claim

The invention claimed is:

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

wherein R 1 is a hydroxyl group, C 1 -C 6 straight, branched or cyclic alkyl or alkoxy group, C 2 -C 6 straight, branched or cyclic acyloxy group, fluorine, chlorine, bromine, amino, —NR 5 —C(═O)—R 6 , or —NR 5 —C(═O)—O—R 6 , R 5 is hydrogen or a C 1 -C 6 straight, branched or cyclic alkyl group, R 6 is a C 1 -C 6 straight, branched or cyclic alkyl group or C 2 -C 8 straight, branched or cyclic alkenyl group; X 1 is a single bond or a (q+1)-valent C 1 -C 20 linking group which may contain at least one moiety selected from ether, carbonyl, ester, amide, sultone, lactam, carbonate, halogen, hydroxyl and carboxyl; X 2 is an ether, ester or amide group; R 2 and R 3 are each independently trifluoromethyl or a C 6 -C 10 aryl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl group in which at least one hydrogen atom may be substituted by halogen, trifluoromethyl, C 1 -C 10 straight, branched or cyclic alkyl, C 1 -C 10 straight, branched or cyclic alkoxy, hydroxyl, carboxyl, C 2 -C 10 straight, branched or cyclic alkoxycarbonyl, nitro and/or cyano; m is an integer of 1 to 5, n is an integer of 0 to 3, p is an integer of 1 to 4, and q is an integer of 1 to 3.

2. The resist composition of claim 1 wherein m is equal to 3.

3. The resist composition of claim 1 wherein the acid generator is capable of generating a sulfonic acid, imide acid or methide acid.

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

5. 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, R 11 and R 12 each are an acid labile group, Y 1 is a single bond, phenylene group, naphthylene group, or C 1 -C 12 linking group containing an ester moiety and/or lactone ring, and Y 2 is a single bond or ester group.

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

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

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

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

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

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

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

wherein R 1 is a hydroxyl group, C 1 -C 6 straight, branched or cyclic alkyl or alkoxy group, C 2 -C 6 straight, branched or cyclic acyloxy group, fluorine, chlorine, bromine, amino, —NR 5 —C(═O)—R 6 , or —NR 5 —C(═O)—O—R 6 , R 5 is hydrogen or a C 1 -C 6 straight, branched or cyclic alkyl group, R 6 is a C 1 -C 6 straight, branched or cyclic alkyl group or C 2 -C 8 straight, branched or cyclic alkenyl group, X 1 is a single bond or a (q+1)-valent C 1 -C 20 linking group which may contain at least one moiety selected from ether, carbonyl, ester, amide, sultone, lactam, carbonate, halogen, hydroxyl and carboxyl; X 2 is an ether, ester or amide group; R 2 and R 3 are each independently trifluoromethyl or a C 6 -C 10 aryl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl group in which at least one hydrogen atom may be substituted by halogen, trifluoromethyl, C 1 -C 10 straight, branched or cyclic alkyl, C 1 -C 10 straight, branched or cyclic alkoxy, hydroxyl, carboxyl, C 2 -C 10 straight, branched or cyclic alkoxycarbonyl, nitro and/or cyano; m is an integer of 1 to 5, n is an integer of 0 to 3, p is an integer of 1 to 4, and q is an integer of 1 to 3,
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 12 — or —C(═O)—Z 11 -Z 12 —, Z 11 is —O— or —NH—, Z 12 is a C 1 -C 6 straight, branched or cyclic alkylene group, C 2 -C 6 straight, branched or cyclic alkenylene group or phenylene group, which may contain a carbonyl, ester, ether or hydroxy moiety,
R 21 to R 28 are each independently a C 1 -C 12 straight, branched or cyclic alkyl group which may contain a carbonyl, ester or ether moiety, or a 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, any two of R 23 , R 24 and R 25 , or any two of R 26 , R 27 and R 28 may bond together 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 C 1 -C 12 straight, branched or cyclic alkylene group which may contain a carbonyl, ester or ether moiety,
A is hydrogen or trifluoromethyl,
Z 3 is a single bond, methylene group, ethylene group, phenylene group, fluorinated phenylene group, —O—Z 32 —, or —C(═O)—Z 31 -Z 32 —, Z 31 is —O— or —NH—, Z 32 is a C 1 -C 6 straight, branched or cyclic alkylene group, phenylene, fluorinated phenylene or trifluoromethyl-substituted phenylene group, or C 2 -C 6 straight, branched or cyclic alkenylene group, which may contain a carbonyl, ester, ether or hydroxyl moiety, and
M − is a non-nucleophilic counter ion.

13. 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.

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

15. The process of claim 13 wherein the high-energy radiation is electron beam or extreme ultraviolet radiation of wavelength 3 to 15 nm.

16. A process for forming a pattern comprising the steps of applying the resist composition of claim 12 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.

17. The process of claim 16 wherein the high-energy radiation is ArF excimer laser radiation of wavelength 193 nm or KrF excimer laser radiation of wavelength 248 nm.

18. The process of claim 16 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

• G03F7/2006

  using coherent light; using polarised light · CPC title

• G03F7/325

  Non-aqueous compositions · CPC title

• G03F7/0046

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

• C07C309/39

  containing halogen atoms bound to the carbon skeleton · CPC title

• G03F7/322

  Aqueous alkaline compositions · CPC title