Resist composition and patterning process

Patent metadata

Field	Value
Publication number	US-11340527-B2
Application number	US-202017082175-A
Country	US
Kind code	B2
Filing date	Oct 28, 2020
Priority date	Nov 7, 2019
Publication date	May 24, 2022
Grant date	May 24, 2022

Abstract

A resist composition containing: (A) a resin containing a repeating unit having an acid-labile group and not containing a repeating unit having an aromatic substituent; (B) a photo-acid generator shown by a general formula (B-1); and (C) a solvent, where W1 represents a cyclic divalent hydrocarbon group having 4 to 12 carbon atoms and containing a heteroatom; W2 represents a cyclic monovalent hydrocarbon group having 4 to 14 carbon atoms and not containing a heteroatom; Rf represents a divalent organic group shown by the following general formula; and M+ represents an onium cation. This provides a resist composition and a patterning process that uses the resist composition that show a particularly favorable mask dimension dependency (mask error factor: MEF), LWR, and critical dimension uniformity (CDU) particularly in photolithography where a high-energy beam such as an ArF excimer laser beam is used as a light source.

First claim

The invention claimed is:

1. A resist composition comprising:
(A) a resin containing a repeating unit having an acid-labile group and not containing a repeating unit having an aromatic substituent, the repeating unit having an acid-labile group shown by the following general formula (a1):

where R 1 represents a hydrogen atom or a methyl group; and X represents at least one acid-labile group selected from (I) and (II):
(I) 1-methylcyclopentyl, 1-ethylcyclopentyl, 1-n-propylcyclopentyl, 1-isopropylcyclopentyl, 1-n-butylcyclopentyl, 1-sec-butylcyclopentyl, 1-tert-butylcyclopentyl, 1-cyclohexylcyclopentyl, 1-(4-methoxy-n-butyl)cyclopentyl, 1-methylcyclohexyl, 1-ethylcyclohexyl, 3-methyl-1-cyclopenten-3-yl, 3-ethyl-1-cyclopenten-3-yl, 3-methyl-1-cyclohexen-3-yl, and 3-ethyl-1-cyclohexen-3-yl;
(II) groups shown by the following formulae:

(B) a photo-acid generator

that (III) consists of the photo-acid generator shown by the general formula (B-1); or (IV) includes a combination of the photo-acid generator shown by the general formula (B-1) and at least one other photo-acid generator selected from the photo-acid generators shown by formula (B-2), formula (B-3), and formula (B-4); and
(C) a solvent,
General Formula (B-1):

wherein W 1 represents a cyclic divalent hydrocarbon group having 4 to 12 carbon atoms and containing a heteroatom; W 2 represents a cyclic monovalent hydrocarbon group having 4 to 14 carbon atoms and not containing a heteroatom; Rf represents a divalent organic group shown by the above general formula; A 1 and A 2 each independently represent a hydrogen atom or a trifluoromethyl group; B 1 and B 2 each independently represent a hydrogen atom or a fluorine atom; * represents an attachment point for a carbonyloxy group; “m” represents an integer of 0 to 4; “n” represents an integer of 1; and M + represents an onium cation that is at least one cation selected from the cations of the following formula group (b1) and formula (b2):
(i) formula group (b1):

(ii) formula (b2):

wherein R 44 and R 45 each independently represent a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms and optionally containing a heteroatom,

General Formulas (B-2), (B-3), and (B-4):

wherein A 1 represents a hydrogen atom or a trifluoromethyl group; R 21 represents a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 35 carbon atoms optionally containing an oxygen atom, a nitrogen-containing heterocyclic group, or a group represented by the following formula (i); M B + represents the same onium cation as M + ;

where R 31 and R 32 each independently represent a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms optionally containing a heteroatom; R 31 and R 32 optionally bond with each other to form a ring with a nitrogen atom bonded to R 31 and R 32 ; R 33 represents a linear, branched, or cyclic divalent hydrocarbon group having 1 to 20 carbon atoms optionally containing a heteroatom; wherein A 2 represents a hydrogen atom or a trifluoromethyl group; R 22 , R 23 , and R 24 each independently represent a hydrogen atom or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms optionally containing a heteroatom; “p” and “q” each independently represent an integer of 0 to 5; “r” represents an integer of 0 to 4; L represents a single bond, an ether group, or a linear, branched, or cyclic divalent hydrocarbon group having 1 to 20 carbon atoms optionally containing a heteroatom; A 3 and A 4 each independently represent a hydrogen atom or a trifluoromethyl group, and are not both a hydrogen atom at the same time; and R 25 represents a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 35 carbon atoms optionally containing an oxygen atom, a nitrogen-containing heterocyclic group, or a group shown by the formula (i).

2. The resist composition according to claim 1 , wherein W 1 in the general formula (B-1) represents a cyclic divalent hydrocarbon group containing a lactone ring structure having 6 to 12 carbon atoms.

3. The resist composition according to claim 1 , wherein W 2 in the general formula (B-1) represents a polycyclic monovalent hydrocarbon group having 7 to 14 carbon atoms and not containing a heteroatom.

4. The resist composition according to claim 2 , wherein W 2 in the general formula (B-1) represents a polycyclic monovalent hydrocarbon group having 7 to 14 carbon atoms and not containing a heteroatom.

5. The resist composition according to claim 1 , wherein the group Rf in the general formula (B-1) is selected from groups shown by the following formulae (Rf-1) and (Rf-3) to (Rf-6),

wherein * represents an attachment point for a carbonyloxy group.

6. The re

Assignees

• Shinetsu Chemical Co

Inventors

• Adachi Teppei
• Yamashita Shinya
• Ohashi Masaki
• Fujiwara Takayuki

Classifications

• G03F7/0382

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

• G03F7/0048

  characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents · CPC title

• C08F220/1808

  C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate · CPC title

• C07C381/12

  Sulfonium compounds · CPC title

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title