Chemically amplified positive resist composition and pattern forming process

Patent metadata

Field	Value
Publication number	US-2016246175-A1
Application number	US-201615044827-A
Country	US
Kind code	A1
Filing date	Feb 16, 2016
Priority date	Feb 25, 2015
Publication date	Aug 25, 2016
Grant date	—

Abstract

A resist composition comprising a resin adapted to be decomposed under the action of acid to increase its solubility in alkaline developer and a sulfonium or iodonium salt of nitrogen-containing carboxylic acid has a high resolution. By lithography, a pattern with minimal LER can be formed.

First claim

1 . A chemically amplified positive resist composition for high-energy radiation lithography, comprising (A) an onium salt compound having the general formula (1) or (2) and (B) a resin comprising recurring units having the general formula (U-1), adapted to be decomposed under the action of acid to increase its solubility in alkaline developer,

wherein R 01 , R 02 , R 03 and R 04 are each independently hydrogen, -L-CO 2 − , or a straight C 1 -C 20 , branched or cyclic C 3 -C 20 monovalent hydrocarbon group which may be substituted with or separated by a heteroatom, or a pair of R 01 and R 02 , R 02 and R 03 , or R 03 and R 04 may bond together to form a ring with the carbon atoms to which they are attached, L is a single bond or a straight C 1 -C 20 , branched or cyclic C 3 -C 20 divalent hydrocarbon group which may be substituted with or separated by a heteroatom, R 05 is hydrogen or a straight C 1 -C 20 , branched or cyclic C 3 -C 20 monovalent hydrocarbon group which may be substituted with or separated by a heteroatom, R 06 , R 07 , R 08 , R 09 , R 010 and R 011 are each independently hydrogen or a straight C 1 -C 20 , branched or cyclic C 3 -C 20 monovalent hydrocarbon group which may be substituted with or separated by a heteroatom, or a pair of R 06 and R 07 may bond together to form a ring with the carbon atoms to which they are attached, a pair of R 08 and R 011 may bond together to form a ring with the carbon atoms to which they are attached and any intervening carbon atoms, or a pair of R 09 and R 010 may bond together to form a ring with the nitrogen atom, j is 0 or 1, k is a number in the range: 0≦k≦1 when j=0, or 0≦k≦3 when j=1, and Z + is a sulfonium cation of the general formula (a) or an iodonium cation of the general formula (b):

wherein R 100 , R 200 , and R 300 are each independently a straight C 1 -C 20 , branched or cyclic C 3 -C 20 , monovalent hydrocarbon group which may be substituted with or separated by a heteroatom, or any two or more of R 100 , R 200 , and R 300 may bond together to form a ring with the sulfur atom, R 400 and R 500 are each independently a straight C 1 -C 20 , branched or cyclic C 3 -C 20 monovalent hydrocarbon group which may be substituted with or separated by a heteroatom,
the partial structure represented by the formula:

is a cyclic structure having the intervening nitrogen atom in which a hydrogen atom bonded to a cyclic structure-forming carbon atom may be replaced by a straight C 1 -C 20 , branched or cyclic C 3 -C 20 monovalent hydrocarbon group or -L-CO 2 − , or in which a cyclic structure-forming carbon atom may be replaced by sulfur, oxygen or nitrogen, with the proviso that one substituent: -L-CO 2 − is essentially included in formula (1),

wherein q is 0 or 1, r is an integer of 0 to 2, R 1 is hydrogen, fluorine, methyl or trifluoromethyl, R 2 is each independently hydrogen or C 1 -C 6 alkyl, B 1 is a single bond or C 1 -C 10 alkylene group which may contain an ether bond, a is an integer satisfying a≦5+2r−b, and b is an integer of 1 to 3.

2 . The resist composition of claim 1 wherein the anion moiety of the onium salt compound having formula (1) is selected from the following formulae (1)-1 to (1)-65, and the anion moiety of the onium salt compound having formula (2) is selected from the following formulae (2)-1 to (2)-43.

3 . The resist composition of claim 1 wherein said resin (B) further comprises recurring units having the general formula (U-2):

wherein s is 0 or 1, t is an integer of 0 to 2, R 1 , R 2 and B 1 are as defined above, c is an integer satisfying c≦5+2t−e, d is 0 or 1, e is an integer of 1 to 3, X is an acid labile group when a is 1, and X is hydrogen or an acid labile group when e is 2 or 3, at least one X being an acid labile group.

4 . The resist composition of claim 1 wherein said resin (B) further comprises recurring units of at least one type selected from units having the general formulae (U-3) and (U-4):

wherein f is an integer of 0 to 6, R 3 is each independently hydrogen, an optionally halo-substituted C 1 -C 6 alkyl or primary or secondary alkoxy group, or an optionally halo-substituted C 1 -C 7 alkylcarbonyloxy group, g is an integer of 0 to 4, and R 4 is each independently hydrogen, an optionally halo-substituted C 1 -C 6 alkyl or primary or secondary alkoxy group, or an optionally halo-substituted C 1 -C 7 alkylcarbonyloxy group.

5 . The resist composition of claim 1 wherein said resin (B) further comprises recurring units of at least one type selected from units having the general formulae (a1), (a2) and (a3):

wherein R 12 is each independently hydrogen or methyl; R 13 is a single bond, phenylene, —O—R 22 —, or —C(O)—Z 2 —R 22 —, Z 2 is oxygen or NH, R 22 is a straight, branched or cyclic C 1 -C 6 alkylene, alkenylene or phenylene group, which may contain a carbonyl (—CO—), ester (—COO—), ether (—O—), or hydroxyl moiety; L n is a single bond or —Z 3 —C(═O)—O—, Z 3 is a straight, branched or cyclic C 1 -C 20 divalent hydrocarbon group which may be substituted with or separated by a heteroatom, Z 1 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, —O—R 23 — or —C(═O)—Z 4 —R 23 —, Z 4 is oxygen or NH, R 23 is a straight, branched or cyclic C 1 -C 6 alkylene, alkenylene or phenylene group, which may contain a carbonyl, ester, ether, or hydroxyl moiety; M − is a non-nucleophilic counter ion; R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , and R 21 are each independently a straight C 1 -C 20 , branched or cyclic C 3 -C 20 monovalent hydrocarbon group in which a hydrogen atom may be substituted by a heteroatom selected from oxygen, sulfur, nitrogen and halogen or in which a heteroatom selected from oxygen, sulfur and nitrogen may intervene, so that a hydroxyl, cyano, carbonyl, ether bond, eater

Assignees

• Shinetsu Chemical Co

Inventors

• Kotake Masaaki
• Fujiwara Takayuki
• Masunaga Keiichi
• Domon Daisuke
• Watanabe Satoshi

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• H10P76/20

  of masks comprising organic materials · CPC title

• G03F7/0395

  the macromolecular compound having a backbone with alicyclic moieties · CPC title

• G03F7/0392 Primary

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

• G03F7/0045

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