Resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-11644753-B2
Application number	US-202117212275-A
Country	US
Kind code	B2
Filing date	Mar 25, 2021
Priority date	Jun 25, 2020
Publication date	May 9, 2023
Grant date	May 9, 2023

Abstract

A resist composition is provided comprising a base polymer and a quencher comprising a salt compound consisting of a cyclic ammonium cation and a 1,1,1,3,3,3-hexafluoro-2-propoxide anion having a trifluoromethyl, hydrocarbylcarbonyl or hydrocarbyloxycarbonyl group bonded thereto. The resist composition has a high sensitivity and forms a pattern with improved LWR or 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,
said quencher comprising a salt compound consisting of a cyclic ammonium cation having the formula (A-1) or (A-2) and a 1,1,1,3,3,3-hexafluoro-2-propoxide anion having bonded thereto a group selected from trifluoromethyl, hydrocarbylcarbonyl and hydrocarbyloxycarbonyl,

wherein m is an integer of 1 to 6,
R 1 is a C 1 -C 30 hydrocarbyl group when m=1, a single bond or C 1 -C 30 hydrocarbylene group when m=2, and a m-valent C 1 -C 30 hydrocarbon group when m is an integer of 3 to 6, the hydrocarbyl, hydrocarbylene and m-valent hydrocarbon groups may contain at least one moiety selected from hydroxyl, thiol, ester bond, thioester bond, thionoester bond, ether bond, sulfide bond, halogen, nitro, amino, amide bond, sulfonyl, sulfonate bond, sultone ring, lactam ring, and carbonate, exclusive of an aromatic hydrocarbon group having iodine bonded to the aromatic ring,
R 2 and R 3 are each independently a C 1 -C 6 saturated hydrocarbyl 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 alkyl group or C 2 -C 12 alkoxycarbonyl group,
R 5 is a C 1 -C 6 aliphatic hydrocarbyl group or C 6 -C 12 aryl group, which may be substituted with halogen or trifluoromethyl,
the ring R is a C 2 -C 10 alicyclic group containing the nitrogen atom.

2. The resist composition of claim 1 wherein the 1,1,1,3,3,3-hexafluoro-2-propoxide anion having bonded thereto a group selected from trifluoromethyl, hydrocarbylcarbonyl and hydrocarbyloxycarbonyl has the formula (B):

wherein R 7 is a trifluoromethyl group, C 1 -C 20 hydrocarbyloxy group or C 2 -C 21 hydrocarbyloxycarbonyl group, the hydrocarbyl moiety in the hydrocarbyloxy group or hydrocarbyloxycarbonyl group may contain at least one moiety selected from ether bond, ester bond, thiol, cyano, nitro, hydroxyl, sultone, sulfonate bond, amide bond, and halogen.

3. The resist composition of claim 1 , further comprising an acid generator 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,
X 1 is a single bond, phenylene, naphthylene, or a C 1 -C 12 linking group containing an ester bond and/or lactone ring,
X 2 is a single bond or ester bond,
X 3 is a single bond, ether bond or ester bond,
R 11 and R 12 are each independently an acid labile group,
R 13 is fluorine, trifluoromethyl, cyano or C 1 -C 6 saturated hydrocarbyl 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 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 1 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 , further comprising a surfactant.

10. The resist composition of claim 1 wherein the base polymer 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, a C 1 -C 6 aliphatic hydrocarbylene group, phenylene group, naphthylene group, or C 7 -C 18 group obtained by combining the foregoing, or —O—Z 11 —, —C(═O)—O—Z 11 — or —C(═O)—NH—Z 11 —, Z 11 is a C 1 -C 6 aliphatic hydrocarbylene group, phenylene group, naphthylene group, or C 7 -Cis group obtained by combining the foregoing, which may contain a carbonyl moiety, 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 saturated hydrocarbylene 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 aliphatic hydrocarbylene 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 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 the sulfur atom to which they are attached,
R HF is hydrogen or trifluoromethyl, and
M − is a non-nucleophilic counter ion.

11. A pattern forming process 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.

12. The process of claim 11 wherein the high-energy radiation is i-line of wavelength 365 nm, ArF excimer laser of wavelength 193 nm or KrF excimer laser of wavelength 248 m.

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

Assignees

• Shinetsu Chemical Co

Inventors

• Hatakeyama Jun

Classifications

• G03F7/0397

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

• C07C211/62

  Quaternary ammonium compounds · CPC title

• G03F7/0045 Primary

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

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• G03F7/26

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