Resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-11460773-B2
Application number	US-201916729643-A
Country	US
Kind code	B2
Filing date	Dec 30, 2019
Priority date	Jan 25, 2019
Publication date	Oct 4, 2022
Grant date	Oct 4, 2022

Abstract

A resist composition comprising a base polymer and a quencher in the form of an amine compound having an iodized aromatic ring and a tertiary ester structure offers a high sensitivity and minimal LWR or improved CDU, independent of whether it is of positive or negative tone.

First claim

The invention claimed is:

1. A resist composition comprising a base polymer and a quencher, the quencher containing at least one compound selected from amine compounds having the formula (A-1) and amine compounds having the formula (A-2):

wherein X is a single bond or a C 1 -C 20 divalent linking group which may contain an ether bond, carbonyl moiety, ester bond, amide bond, sultone ring, lactam ring, carbonate bond, halogen, hydroxyl moiety or carboxyl moiety,
R 1 is hydrogen, hydroxyl, an optionally halo-substituted C 1 -C 6 alkyl group, optionally halo-substituted C 1 -C 6 alkoxy group, optionally halo-substituted C 2 -C 6 acyloxy group, optionally halo-substituted C 1 -C 4 alkylsulfonyloxy group, fluorine, chlorine, bromine, amino, nitro, cyano, —NR 1A —C(═O)—R 1B , or —NR 1A —C(═O)—O—R 1B , R 1A is hydrogen or a C 1 -C 6 alkyl group, R 1B is a C 1 -C 6 alkyl group or C 2 -C 8 alkenyl group,
R 2 and R 3 are each independently a C 1 -C 6 alkyl group, R 2 and R 3 may bond together to form a ring with the carbon atom to which they are attached,
R 4 and R 6 are each independently hydrogen, a C 1 -C 4 straight or branched alkyl group, C 2 -C 12 straight or branched alkoxycarbonyl group, C 6 -C 15 aryloxycarbonyl group, or C 6 -C 14 aralkyloxycarbonyl group,
R 5 is a C 1 -C 6 alkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 alkynyl group, or C 6 -C 12 aryl group,
R is a C 2 -C 10 alicyclic group to form a ring with the nitrogen atom,
m is an integer of 1 to 5, n is an integer of 0 to 4, and 1≤m+n≤5, and p is 1 or 2.

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, 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 at least one moiety selected from ester bond and lactone ring, and Y 2 is a single bond or ester bond.

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

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

7. The resist composition of claim 6 which is a chemically amplified negative resist composition.

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

9. The resist composition of claim 1 wherein the base polymer further comprises recurring units of at least one type selected from recurring units having 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 —, —C(═O)—O—Z 11 — or —C(═O)—NH—Z 11 —, Z 11 is a C 1 -C 6 alkanediyl group, C 2 -C 6 alkenediyl group, or phenylene group, which may contain a carbonyl, ester bond, ether bond or hydroxyl moiety,
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 alkanediyl group which may contain a carbonyl moiety, ester bond or ether bond,
Z 3 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, —O—Z 31 —, —C(═O)—O—Z 31 —, or —C(═O)—NH—Z 31 —, Z 31 is a C 1 -C 6 alkanediyl group, C 2 -C 6 alkenediyl group, phenylene group, fluorinated phenylene group, or trifluoromethyl-substituted phenylene group, which may contain a carbonyl moiety, ester bond, ether bond or hydroxyl moiety,
R 21 to R 28 are each independently a C 1 -C 20 monovalent hydrocarbon group which may contain a heteroatom, 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,
A is hydrogen or trifluoromethyl, and
M − is a non-nucleophilic counter ion.

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

11. The process of claim 10 wherein the high-energy radiation is ArF excimer laser radiation of wavelength 193 nm or KrF excimer laser radiation of wavelength 248 nm.

12. The process of claim 10 wherein the high-energy radiation is EB or EUV of wavelength 3 to 15 nm.

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Fujiwara Takayuki
• Ohashi Masaki

Classifications

• G03F7/033

  the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers · CPC title

• G03F7/2037

  Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation · CPC title

• G03F7/0045 Primary

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

• G03F7/26

  Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence) · CPC title

• G03F7/2006

  using coherent light; using polarised light · CPC title