Resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-11409194-B2
Application number	US-201916530438-A
Country	US
Kind code	B2
Filing date	Aug 2, 2019
Priority date	Aug 9, 2018
Publication date	Aug 9, 2022
Grant date	Aug 9, 2022

Abstract

A resist composition comprising a base polymer and a quencher in the form of an amine compound having an iodized aromatic ring bonded to the nitrogen atom via a divalent hydrocarbon group 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 being an amine compound, wherein the amine compound has the formula (A):

wherein R 1 is hydroxyl, C 1 -C 6 alkyl group, C 1 -C 6 alkoxy group, C 2 -C 6 acyloxy group, fluorine, chlorine, bromine, amino group, —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, C 2 -C 8 alkenyl, C 6 -C 12 aryl or C 7 -C 13 aralkyl group,
R 2 is hydrogen, nitro, or a C 1 -C 20 monovalent hydrocarbon group which may contain at least one moiety selected from hydroxyl, carboxyl, thiol, ether bond, ester bond, nitro, cyano, halogen and amino moiety, in case of p=1, R 2 may bond together to form a ring with the nitrogen atom to which they are attached, the ring optionally containing a double bond, oxygen, sulfur or nitrogen, or R 2 and X may bond together to form a ring with the nitrogen atom to which they are attached, the ring optionally containing a double bond, oxygen, sulfur or nitrogen,
X is a C 1 -C 20 divalent hydrocarbon group which contains at least one moiety selected from ester bond and ether bond,
m and n are independently an integer meeting 1≤m≤5, 0≤n≤4 and 1≤m+n≤5, and p is 1, 2 or 3.

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 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 hydroxy 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.

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

10. The resist composition of claim 1 , further comprising a quencher other than the amine compound.

11. 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 resist film in a developer.

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

13. The process of claim 11 wherein the high-energy radiation is EB or EUV of wavelength 3 to 15 nm.

14. An amine compound having the formula (A′):

wherein R 1 is hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 alkoxy group, C 2 -C 6 acyloxy group, fluorine, chlorine, bromine, amino, —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, C 2 -C 8 alkenyl, C 6 -C 12 aryl or C 7 -C 13 aralkyl group,
X is a C 1 -C 20 divalent hydrocarbon group which may contain at least one moiety selected from ester bond and ether bond,
the ring R 3 is a C 4 -C 6 heterocycle formed with the nitrogen atom, which may contain an ether bond, thioether bond, —N(R 4 )—, carbonyl group or sulfonyl group, R 4 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 8 acyl, C 7 -C 20 aralkyl or C 1 -C 16 alkoxycarbonyl group,
m and n are independently an integer meeting 1≤m≤5, 0≤n≤4 and 1≤m+n≤5.

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun
• Ohashi Masaki
• Fujiwara Takayuki

Classifications

• C07D295/088

  to an acyclic saturated chain · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• G03F7/033

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

• C07D453/02

  containing not further condensed quinuclidine ring systems · CPC title

• C07D211/46

  having a hydrogen atom as the second substituent in position 4 · CPC title