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US 12,216,401 B2Granted
Sulfonium salt, chemically amplified resist composition, and patterning process
AssigneeShin-Etsu Chemical Co., Ltd.
InventorsMasahiro Fukushima, Kazuhiro Katayama
Life of this patent
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Abstract
A sulfonium salt having formula (1) is novel. A chemically amplified resist composition comprising the sulfonium salt as a PAG has advantages including solvent solubility and improved lithography properties such as EL and LWR when processed by photolithography using high-energy radiation such as KrF or ArF excimer laser, EB or EUV.
Claims19
A sulfonium salt having the formula (1):
- wherein p is an integer of 1 to 5, q is an integer of 1 to 3,
- RHF is hydrogen or fluorine,
- R1 is a C1-C20 (p+1)-valent hydrocarbon group which may contain a heteroatom,
- R2 is a C6-C20 aryl group or C7-C20 aralkyl group which may contain a heteroatom,
- in case of q=1, any two of R1 and two R2 may bond together to form a ring with the sulfur atom to which they are attached, in case of q=2, any two of two R1 and R2 may bond together to form a ring with the sulfur atom to which they are attached, in case of q=3, any two of three R1 may bond together to form a ring with the sulfur atom to which they are attached, wherein the ring is selected from the group consisting of the following formulae:
- X− is a non-nucleophilic anion selected from the formulae (2A) to (2D):
- wherein Q1 and Q2 are each independently fluorine or a C1-C6 fluorinated alkyl group,
- Q3 and Q4 are each independently hydrogen, fluorine or a C1-C6 fluorinated alkyl group,
- k is an integer of 0 to 4,
- L1 to L4 are each independently a single bond, ether bond, ester bond, sulfonic ester bond, carbonate bond or carbamate bond,
- R5 is a C1-C30 hydrocarbyl group which may contain a heteroatom,
- A1 is a C1-C30 hydrocarbylene group which may contain a heteroatom,
- RA is each independently hydrogen, fluorine, methyl or trifluoromethyl,
- X1 is a single bond, phenylene, naphthylene or (backbone)-C(═O)—O—X11—, X11 is a C1-C10 aliphatic hydrocarbylene group which may contain a hydroxy moiety, ether bond, ester bond or lactone ring, or phenylene or naphthylene group,
- X2 is a single bond or —X21—C(═O)—O—, X21 is a C1-C20 hydrocarbylene group which may contain a heteroatom, and
- X3 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, trifluoromethyl-substituted phenylene, —O—X31—, —C(═O)—O—X31—, or —C(═O)—NH—X31—, X31 is a C1-C6 aliphatic hydrocarbylene group, phenylene group, fluorinated phenylene group, or trifluoromethyl-substituted phenylene group, which may contain a carbonyl moiety, ester bond, ether bond or hydroxy moiety.
13 more elements
A photoacid generator comprising a sulfonium salt having the formula (1):
- wherein p is an integer of 1 to 5, q is an integer of 1 to 3,
- RHF is hydrogen or fluorine,
- R1 is a C1-C20 (p+1)-valent hydrocarbon group which may contain a heteroatom,
- R2 is a C6-C20 aryl group or C7-C20 aralkyl group which may contain a heteroatom,
- in case of q=1, any two of R1 and two R2 may bond together to form a ring with the sulfur atom to which they are attached, in case of q=2, any two of two R1 and R2 may bond together to form a ring with the sulfur atom to which they are attached, in case of q=3, any two of three R1 may bond together to form a ring with the sulfur atom to which they are attached, wherein the ring is selected from the group consisting of the following formulae:
- X− is a non-nucleophilic anion.
3 more elements
A chemically amplified resist composition comprising a base polymer comprising repeat units having the formula (a1) or (a2) and repeat units having the formula (a3) or (a4):
- wherein RA is each independently hydrogen, fluorine, methyl or trifluoromethyl,
- Y1 is a single bond, phenylene, naphthylene or (backbone)-C(═O)—O—Y11—, Y11 is a C1-C10 alkanediyl group which may contain a hydroxy moiety, ether bond, ester bond or lactone ring, or phenylene or naphthylene group,
- Y2 is a single bond or (backbone)-C(═O)—O—,
- AL1 and AL2 are each independently an acid labile group,
- R11 is a C1-C20 hydrocarbyl group which may contain a heteroatom, and
- a is an integer of 0 to 4,
- wherein p is an integer of 1 to 5, q is an integer of 1 to 3,
- RHF is hydrogen or fluorine,
- R1 is a C1-C20 (p+1)-valent hydrocarbon group which may contain a heteroatom,
- R2 is a C6-C20 aryl group or C7-C20 aralkyl group which may contain a heteroatom,
- in case of q=1, any two of R1 and two R2 may bond together to form a ring with the sulfur atom to which they are attached, in case of q=2, any two of two R1 and R2 may bond together to form a ring with the sulfur atom to which they are attached, in case of q=3, any two of three R1 may bond together to form a ring with the sulfur atom to which they are attached, wherein the ring is selected from the group consisting of the following formulae:
- L4 is each independently a single bond, ether bond, ester bond, sulfonic ester bond, carbonate bond or carbamate bond,
- RA is each independently hydrogen, fluorine, methyl or trifluoromethyl,
- X1 is a single bond, phenylene, naphthylene or (backbone)-C(═O)—O—X11—, X11 is a C1-C10 aliphatic hydrocarbylene group which may contain a hydroxy moiety, ether bond, ester bond or lactone ring, or phenylene or naphthylene group,
- X2 is a single bond or —X21—C(═O)—O—, X21 is a C1-C20 hydrocarbylene group which may contain a heteroatom,
- X3 is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, trifluoromethyl-substituted phenylene, —O—X31—, —C(═O)—O—X31—, or —C(═O)—NH—X31—, X31 is a C1-C6 aliphatic hydrocarbylene group, phenylene group, fluorinated phenylene group, or trifluoromethyl-substituted phenylene group, which may contain a carbonyl moiety, ester bond, ether bond or hydroxy moiety, and
- k is an integer of 0 to 4.
14 more elements
Dependencies are inferred from the claim text.