CN112782935A - Resist composition and pattern forming method - Google Patents
Resist composition and pattern forming method Download PDFInfo
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- CN112782935A CN112782935A CN202011225387.2A CN202011225387A CN112782935A CN 112782935 A CN112782935 A CN 112782935A CN 202011225387 A CN202011225387 A CN 202011225387A CN 112782935 A CN112782935 A CN 112782935A
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- 238000000034 method Methods 0.000 title claims abstract description 36
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- -1 R201Is a single bond Chemical group 0.000 claims description 192
- 125000004432 carbon atom Chemical group C* 0.000 claims description 98
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- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000004434 sulfur atom Chemical group 0.000 claims description 25
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000005380 borophosphosilicate glass Substances 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- CSYSRRCOBYEGPI-UHFFFAOYSA-N diazo(sulfonyl)methane Chemical compound [N-]=[N+]=C=S(=O)=O CSYSRRCOBYEGPI-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000000671 immersion lithography Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- MBAHGFJTIVZLFB-UHFFFAOYSA-N methyl pent-2-enoate Chemical compound CCC=CC(=O)OC MBAHGFJTIVZLFB-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical group 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 108010001861 pregnancy-associated glycoprotein 1 Proteins 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/70—Microphotolithographic exposure; Apparatus therefor
- G03F7/70008—Production of exposure light, i.e. light sources
- G03F7/70025—Production of exposure light, i.e. light sources by lasers
Abstract
The invention relates to a resist composition and a pattern forming method. The present invention addresses the problem of providing a resist composition that exhibits particularly good mask dimension dependence (mask error factor: MEF) and dimensional uniformity (CDU) in photolithography using high-energy rays such as KrF excimer laser light, electron beam, and extreme ultraviolet light as a light source, and also providing a pattern formation method using the resist composition. The solution of the problem is a resist composition, which is characterized by comprising: (A) a resin containing a repeating unit having an acid-labile group and further containing at least 1 repeating unit having an aromatic substituent, (B) a photoacid generator represented by the general formula (B-1), and (C) a solvent.
In the formula, W1Represents a C4-12 hetero atom-containing cyclic 2-valent hydrocarbon group. W2Represents a C4-C14 cyclic 1-valent hydrocarbon group containing no hetero atom. Rf is a 2-valent organic group represented by the above general formula. M+Represents an onium cation.
Description
Technical Field
The invention relates to a resist composition and a pattern forming method.
Background
Along with the high integration and high speed of LSI, the miniaturization is rapidly progressing. In the most advanced miniaturization technology, the mass production by ArF immersion lithography in which exposure is performed by inserting a liquid such as water between a projection lens and a substrate has been carried out, and the multiple exposure (multiple-patterning) of ArF lithography, Extreme Ultraviolet (EUV) lithography with a wavelength of 13.5nm, and the like have been studied.
Among the chemically amplified resist materials used for the above-mentioned lithography, a compound which decomposes and generates an acid upon exposure (hereinafter referred to as "acid generator") is used, and by optimizing the structure in the acid generator, it is possible to form a pattern with high resolution while suppressing the diffusion of an acid. Such acid generators have been studied, and are disclosed in patent documents 1 to 4, for example.
Documents of the prior art
Patent document
[ patent document 1] Japanese patent laid-open No. 2008 + 074843
[ patent document 2] Japanese patent laid-open No. 2009- & gt 191054
[ patent document 3] Japanese patent application laid-open publication No. 2011-
[ patent document 4] Japanese patent laid-open No. 2012 and 072108
Disclosure of Invention
Problems to be solved by the invention
When the resist pattern is further miniaturized, the acid generators which have been conventionally investigated are not necessarily sufficient in terms of various performances such as resolution and resist pattern shape.
The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a resist composition and a pattern forming method which exhibit good mask dimension dependency (mask error factor: MEF) and dimensional uniformity (CDU) in photolithography.
Means for solving the problems
In order to solve the above problems, the present invention provides a resist composition comprising: (A) a resin containing a repeating unit having an acid-labile group and further containing at least 1 repeating unit having an aromatic substituent, (B) a photoacid generator represented by the general formula (B-1), and (C) a solvent.
[ solution 1]
In the formula, W1Represents a C4-12 hetero atom-containing cyclic 2-valent hydrocarbon group. W2Represents a C4-C14 cyclic 1-valent hydrocarbon group containing no hetero atom. Rf is a 2-valent organic group represented by the general formula1、A2Each independently represents a hydrogen atom or a trifluoromethyl group, B1、B2Each independently represents a hydrogen atom, a fluorine atom or a trifluoromethyl group, and represents an atomic bond to a carbonyloxy group. m represents 0 to 4, and n represents an integer of 0 to 1. M+Represents an onium cation.
The resist composition of the present invention exhibits excellent mask dimension dependency (mask error factor: MEF) and dimension uniformity (CDU) in photolithography.
In this case, W in the above general formula (B-1)1Preferably, the cyclic 2-valent hydrocarbon group has a lactone ring structure having 6 to 12 carbon atoms.
In the resist composition, when an acid is generated after exposure, the lactone ring is arranged at a position near the sulfonic acid group, whereby the acid diffusion can be further suppressed, and thus, more favorable mask dimension dependency and dimensional uniformity can be exhibited.
W in the above general formula (B-1)2Preferably a C7-14 hetero atom-free polycyclic 1-valent hydrocarbon group.
In such a resist composition, a hydrocarbon group having a high degree of ring shrinkage is disposed at the end, and thus appropriate solubility can be provided, and thus more excellent mask size dependency and size uniformity can be exhibited.
Further, the Rf group in the general formula (B-1) is preferably selected from the groups represented by the following formulas (Rf-1) to (Rf-6).
[ solution 2]
Represents an atomic bond to a carbonyloxy group.
Such a resist composition can exhibit more favorable mask size dependency, LWR, and size uniformity because the solubility is improved by the effect of fluorine atoms in Rf, and the sulfonic acid generated after exposure has an appropriate acid strength.
In the resin of the component (A), 1 kind of the repeating units having an aromatic substituent is preferably a repeating unit represented by the following formula (A-1).
[ solution 3]
In the formula, RARepresents a hydrogen atom or a methyl group. R61Represents a hydrogen atom, or a linear, branched or cyclic hydrocarbon group having 1 to 10 carbon atoms and into which a heteroatom may be inserted. R62Represents a C1-C8 linear, branched or cyclic hydrocarbon group which may be interrupted by a heteroatom. t is an integer of 1-3, and u is an integer satisfying u not more than 5+2 s-t. s is 0 or 1. L is1Represents a single bond or any of-C (═ O) O-, -C (═ O) NH-.
The resist composition of the present invention can exhibit more favorable mask size dependency or size uniformity by combining the component (a) and the component (B).
In the resin of the component (A), 1 kind of the repeating units having an aromatic substituent is preferably a repeating unit represented by the following general formulae (A-2) to (A-4).
[ solution 4]
In the formula, RAEach independently is a hydrogen atom or a methyl group, R201Is a single bond, phenylene, -O-R210-, or-C (═ O) -Z2-R210-。Z2Is oxygen atom or NH, R210Is a linear, branched or cyclic alkylene, alkenylene or phenylene group having 1 to 6 carbon atoms, and may contain a carbonyl group (-CO-), an ester group (-COO-), an ether group (-O-) or a hydroxyl group. L is2Represents a single bond, or-Z3-C(＝O)-O-，Z3Represents a C1-20 linear, branched or cyclic 2-valent hydrocarbon group which may be substituted with a hetero atom. Z1Is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, -O-R211-, or-C (═ O) -Z4-R211-。Z4Is oxygen atom or NH, R211Is a linear, branched or cyclic alkylene, alkenylene or phenylene group having 1 to 6 carbon atoms, and may contain a carbonyl group, an ester group, an ether group or a hydroxyl group. M-Denotes a non-nucleophilic counter ion. R202、R203、R204、R205、R206、R207、R208、R209Each independently represents a C1-20 linear or branched or cyclic C3-20 hydrocarbon group which may be substituted with a heteroatom or may be interrupted by a heteroatom. And R is202And R203Or may be bonded to each other and form a ring together with the sulfur atom in the formula, or R204、R205And R206Or R is 2 or more of207、R208And R209Any 2 or more of them may be bonded to each other and form a ring together with the sulfur atom in the formula. However, the repeating units represented by the general formulae (A-2) to (A-4) have 1 or more aromatic substituents.
The resist composition of the present invention can exhibit more favorable mask size dependency or size uniformity by using the component (a) as described above.
The resist composition preferably further contains component (D), is a resin different from the resin of component (A), and is a fluorine-containing resin having at least 1 kind selected from the group consisting of repeating units represented by the following formulae (D-1), (D-2) and (D-3).
[ solution 5]
In the formula, RAEach independently is a hydrogen atom or a methyl group. R51And R52Each independently represents a hydrogen atom, or a linear, branched or cyclic 1-valent hydrocarbon group having 1 to 10 carbon atoms. R53Is a single bond, or a straight or branched 2-valent hydrocarbon group having 1 to 5 carbon atoms. R54、R55And R56Each independently represents a hydrogen atom, or a linear, branched or cyclic 1-valent hydrocarbon group having 1 to 15 carbon atoms, a fluorinated 1-valent hydrocarbon group, an acyl group or an acid-labile group. R54、R55And R56In the case of a 1-valent hydrocarbon group or a fluorinated 1-valent hydrocarbon group, a part of carbon atoms thereof may be substituted with ether groups or carbonyl groups. R57Is a linear, branched or cyclic (v +1) -valent hydrocarbon group or fluorinated hydrocarbon group having 1 to 20 carbon atoms. v is an integer of 1 to 3.
By further containing the component (D), the resist composition of the present invention can improve the contact angle between the surface of the resist film and water, and suppress the dissolution of defects or acid generators or quenchers due to the residual wetting water. Furthermore, the solubility of the surface of the resist film can be adjusted, and excellent dimensional uniformity can be achieved.
Further, the present invention provides a pattern forming method, characterized by comprising the steps of: the resist composition is applied to a substrate and subjected to a heat treatment to form a resist film, the resist film is exposed to a high-energy ray, and the exposed resist film is developed using a developer.
In such a pattern forming method, it is possible to achieve good mask dimension dependency and dimension uniformity in photolithography.
In the pattern forming method of the present invention, the high-energy radiation may be ArF excimer laser having a wavelength of 193nm or KrF excimer laser having a wavelength of 248 nm.
The exposure may be immersion exposure in which a liquid having a refractive index of 1.0 or more is inserted between a resist film and a projection lens, or immersion exposure may be performed to form a pattern by forming a protective film on the resist film and inserting the liquid between the protective film and the projection lens.
In such a patterning method, it is possible to achieve more excellent mask size dependency and size uniformity in photolithography.
In the pattern forming method of the present invention, the high-energy radiation may be an electron beam or extreme ultraviolet radiation having a wavelength of 3 to 15 nm.
With such a pattern forming method, a pattern having good sensitivity and excellent MEF and CDU can be formed.
ADVANTAGEOUS EFFECTS OF INVENTION
The resist composition of the present invention can form a resist pattern having excellent mask dimension dependency (mask error factor: MEF) and LWR.
The present invention can provide a resist composition and a pattern formation method which exhibit excellent mask dimension dependency (mask error factor: MEF) and dimensional uniformity (CDU) particularly in photolithography using high-energy rays such as KrF excimer laser, electron beam, and extreme ultraviolet as a light source.
Drawings
[ FIG. 1] A]Is a PAG1 sample obtained in example 1-11Graph of HNMR atlas.
[ FIG. 2]]Is a PAG1 sample obtained in example 1-119Map of FNMR atlas.
[ FIG. 3]]Is a PAG2 sample obtained in example 1-21Graph of HNMR atlas.
[ FIG. 4]]Is a PAG2 sample obtained in example 1-219Map of FNMR atlas.
Detailed Description
As described above, when the resist is further miniaturized, the acid generator which has been conventionally studied is not necessarily sufficient in terms of various performances such as resolution and resist pattern shape.
The inventors of the present invention have made extensive studies to achieve the above object, and as a result, have found that: a resist composition using an acid generator represented by the following formula (B-1) exhibits good mask dimension dependency (mask error factor: MEF) and dimensional uniformity (CDU), and is extremely effective for precise microfabrication.
That is, the present invention is a resist composition characterized by containing: (A) a resin containing a repeating unit having an acid-labile group and further containing at least 1 repeating unit having an aromatic substituent, (B) a photoacid generator represented by the general formula (B-1), and (C) a solvent.
[ solution 6]
In the formula, W1Represents a C4-12 hetero atom-containing cyclic 2-valent hydrocarbon group. W2Represents a C4-C14 cyclic 1-valent hydrocarbon group containing no hetero atom. Rf is a 2-valent organic group represented by the general formula1、A2Each independently represents a hydrogen atom or a trifluoromethyl group, B1、B2Each independently represents a hydrogen atom, a fluorine atom or a trifluoromethyl group, and represents an atomic bond to a carbonyloxy group. m represents 0 to 4, and n represents an integer of 0 to 1. M+Represents an onium cation.
The present invention will be described in detail below, but the present invention is not limited thereto. In the following chemical formulae, enantiomers (enantiomers) or diastereomers (diameteromers) may be present in the chemical structure, but unless otherwise specified, each chemical formula represents all of these stereoisomers. These stereoisomers may be used alone or in a mixture.
[ resist composition ]
The resist composition of the present invention contains: (A) a resin (base resin) containing a repeating unit having an acid-labile group and further containing at least 1 repeating unit having an aromatic substituent group, (B) a photoacid generator represented by the general formula (B-1), and (C) a solvent. The resin composition may further contain, as necessary, a specific fluorine-containing resin different from the resin of the component (A) as the component (D), or other components such as a quencher, a surfactant and the like. Hereinafter, each component will be described.
[ (A) base resin ]
In the resist composition of the present invention, the base resin (resin a) of component (a) is a resin containing a repeating unit having an acid labile group and containing at least 1 repeating unit having an aromatic substituent.
(A) The repeating unit having an aromatic substituent in the base resin of component (A) may be represented by the following general formula (A-1).
[ solution 7]
In the formula, RARepresents a hydrogen atom or a methyl group. R61Represents a hydrogen atom, or a linear, branched or cyclic hydrocarbon group having 1 to 10 carbon atoms and into which a heteroatom may be inserted. R62Represents a C1-C8 linear, branched or cyclic hydrocarbon group which may be interrupted by a heteroatom. t is an integer of 1-3, and u is an integer satisfying u not more than 5+2 s-t. s is 0 or 1. L is1Represents a single bond or any of-C (═ O) O-, -C (═ O) NH-.
In the above formula, R61The hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, which may be a straight chain, branched or cyclic hydrocarbon group into which a hetero atom may be inserted, includes: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopentyl, cyclohexyl, 1-methylcyclopentyl, 1-methylcyclohexyl, and the like, but are not limited thereto.
In the above formula, R62Examples of the straight-chain, branched or cyclic hydrocarbon group having 1 to 8 carbon atoms, preferably 1 to 5 carbon atoms, into which a heteroatom may be inserted include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, and,The following may be specifically exemplified in addition to hexyl, heptyl, octyl, cyclopentyl and cyclohexyl, but the present invention is not limited thereto.
[ solution 8]
Here, broken lines indicate atomic bonds (the same applies hereinafter).
Specific examples of the repeating unit represented by the general formula (A-1) include, but are not limited to, those described below.
[ solution 9]
In the formula, RAThe same as described above.
[ solution 10]
In the formula, RAThe same as described above.
[ solution 11]
(A) In the base resin of component (A), the repeating units having an aromatic substituent may be represented by the following general formulae (A-2) to (A-4).
[ solution 12]
In the formula, RAEach independently is a hydrogen atom or a methyl group, R201Is a single bond, phenylene, -O-R210-, or-C (═ O) -Z2-R210-。Z2Is oxygen atom or NH, R210Is straight with 1-6 carbon atomsA linear, branched or cyclic alkylene, alkenylene or phenylene group, and may further contain a carbonyl group (-CO-), an ester group (-COO-), an ether group (-O-) or a hydroxyl group. L is2Represents a single bond, or-Z3-C(＝O)-O-，Z3Represents a C1-20 linear, branched or cyclic 2-valent hydrocarbon group which may be substituted with a hetero atom. Z1Is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, -O-R211-, or-C (═ O) -Z4-R211-。Z4Is oxygen atom or NH, R211Is a linear, branched or cyclic alkylene, alkenylene or phenylene group having 1 to 6 carbon atoms, and may contain a carbonyl group, an ester group, an ether group or a hydroxyl group. M-Denotes a non-nucleophilic counter ion. M-Examples thereof include: hydroxyl ions, carboxylate ions, halogen ions, nitrate ions, nitrite ions, chlorate ions, bromate ions, methanesulfonate ions, p-toluenesulfonate ions, monomethyl sulfate ions, carbonate ions, sulfate ions and the like. R202、R203、R204、R205、R206、R207、R208、R209Each independently represents a C1-20 linear or branched or cyclic C3-20 hydrocarbon group which may be substituted with a heteroatom or may be interrupted by a heteroatom. Specific examples thereof include: alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, 4-methylcyclohexyl, cyclohexylmethyl, norbornyl and adamantyl; alkenyl groups such as vinyl, allyl, propenyl, butenyl, hexenyl, and cyclohexenyl; aryl groups such as phenyl, naphthyl, and thienyl; aralkyl groups such as benzyl, 1-phenylethyl and 2-phenylethyl, and aryl is preferable. Further, hydrogen atoms of a part of these groups may be substituted with a hetero atom such as an oxygen atom, a sulfur atom, a nitrogen atom, or a halogen atom, or a hetero atom such as an oxygen atom, a sulfur atom, or a nitrogen atom may be inserted, and as a result, a hydroxyl group, a cyano group, a carbonyl group, an ether bond, an ester bond, a sulfonate bond, a carbonate bond, a lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group, or the like may be formed or inserted. And R is202And R203Can also be mutually bondedCombined with the sulfur atom in the formula to form a ring, or R204、R205And R206Or R is 2 or more of207、R208And R209Any 2 or more of them may be bonded to each other and form a ring together with the sulfur atom in the formula. However, the repeating units represented by the general formulae (A-2) to (A-4) have 1 or more aromatic substituents.
In the above formula, L2is-Z3-C (═ O) -O-, Z3The 2-valent hydrocarbon group which may be a straight chain, branched or cyclic hydrocarbon group having 1 to 20 carbon atoms and which may be substituted with a heteroatom is exemplified by the following, but is not limited thereto.
[ solution 13]
In the formula, the broken line represents an atomic bond.
In the above formula, R202And R203Or may be bonded to each other and form a ring together with the sulfur atom in the formula, or R204、R205And R206Or R is 2 or more of207、R208And R209Any 2 or more of them may be bonded to each other to form a ring together with the sulfur atom in the formula, and in this case, a group represented by the following formula, and the like may be mentioned.
[ solution 14]
In the formula, R212Shown and exemplified as R201Or exemplified as the above R202、R203、R204、R205、R206、R207、R208、R209The same as above.
Specific structures of the sulfonium cations represented by the general formulae (A-3) to (A-4) are shown below. However, the present invention is not limited thereto.
[ solution 15]
(A) The repeating unit having an acid labile group in the base resin of component (a) may be represented by the following general formula (a 1).
[ solution 16]
In the formula, R1Is a hydrogen atom or a methyl group. X represents an acid labile group.
The repeating unit represented by the above general formula (a1) can provide a polymer which is decomposed by the action of an acid to produce a carboxylic acid and is soluble in an alkali. As the acid-labile group X, various groups can be used, and specific examples thereof include groups represented by the following general formulae (L1) to (L9), tertiary alkyl groups having 4 to 20 carbon atoms, preferably 4 to 15 carbon atoms, trialkylsilyl groups having 1 to 6 carbon atoms in each alkyl group, and oxoalkyl groups having 4 to 20 carbon atoms.
[ solution 17]
In the formula (L1), RL01、RL02Represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and specifically includes: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, 2-ethylhexyl, n-octyl, norbornyl, tricyclodecyl, tetracyclododecyl, adamantyl, and the like. RL03The 1-valent hydrocarbon group which may have a heteroatom such as an oxygen atom and has 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, includes straight-chain, branched or cyclic alkyl groups in which some of the hydrogen atoms are substituted with hydroxyl, alkoxy, oxy, amino, alkylamino, and the like, and specific examples thereof include the following substituted alkyl groups.
[ solution 18]
RL01And RL02、RL01And RL03、RL02And RL03Or may be bonded to each other and form a ring together with the carbon atom and the oxygen atom to which they are bonded, when R forms a ringL01、RL02、RL03Each represents a straight-chain or branched alkylene group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms.
In the formula (L2), RL04A tertiary alkyl group having 4 to 20 carbon atoms, preferably 4 to 15 carbon atoms, a trialkylsilyl group having 1 to 6 carbon atoms for each alkyl group, an oxoalkyl group having 4 to 20 carbon atoms, or a group represented by the above general formula (L1), and specific examples thereof include: tert-butyl, tert-amyl, 1-diethylpropyl, 2-cyclopentylpropan-2-yl, 2-cyclohexylpropan-2-yl, 2- (bicyclo [2.2.1]]Heptane-2-yl) propan-2-yl, 2- (adamantan-1-yl) propan-2-yl, 1-ethylcyclopentyl, 1-butylcyclopentyl, 1-ethylcyclohexyl, 1-butylcyclohexyl, 1-ethyl-2-cyclopentenyl, 1-ethyl-2-cyclohexenyl, 2-methyl-2-adamantyl, 2-ethyl-2-adamantyl, and the like, and specific examples thereof include a trialkylsilyl group: trimethylsilyl, triethylsilyl, dimethyl-t-butylsilyl and the like, and specific examples of the oxoalkyl group include: 3-oxocyclohexyl, 4-methyl-2-oxooxacyclohex-4-yl, 5-methyl-2-oxooxacyclopent-5-yl and the like. l is an integer of 0 to 6.
In the formula (L3), RL05The alkyl group which may be substituted, is a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 20 carbon atoms, and the alkyl group which may be substituted specifically includes: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-pentyl, n-hexyl, cyclopentyl, cyclohexyl and other straight-chain, branched or cyclic alkyl groups, wherein a part of the hydrogen atoms of these groups is replaced with a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, an oxy group, an amino group, an alkylamino group, a cyano group, a mercapto group, an alkylthio group, a sulfo group, and the likeThe following examples are given: phenyl, methylphenyl, naphthyl, anthryl, phenanthryl, pyrenyl and the like. In the formula (L3), m is 0 or 1, n is any one of 0, 1, 2, and 3, and is a number satisfying 2m + n ═ 2 or 3.
In the formula (L4), RL06Represents an optionally substituted straight-chain or branched or cyclic alkyl group having 1 to 8 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms, and specifically, RL05The same, etc. RL07～RL16Each independently represents a hydrogen atom or a 1-valent hydrocarbon group having 1 to 15 carbon atoms, and specific examples thereof include: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-pentyl, n-hexyl, n-octyl, n-nonyl, n-decyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylbutyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylbutyl and other linear, branched or cyclic alkyl groups, some of the hydrogen atoms of which are substituted with hydroxyl, alkoxy, carboxyl, alkoxycarbonyl, oxy, amino, alkylamino, cyano, mercapto, alkylthio, sulfo and the like. RL07～RL16May be bonded to each other to form a ring (e.g., R)L07And RL08、RL07And RL09、RL08And RL10、RL09And RL10、RL11And RL12、RL13And RL14Etc.), in which case the alkyl group represents a 2-valent hydrocarbon group having 1 to 15 carbon atoms, and specifically, the alkyl group is exemplified by one obtained by removing 1 hydrogen atom from the 1-valent hydrocarbon group. And R isL07～RL16Wherein adjacent carbons are bonded to each other without any material and form a double bond (e.g., R)L07And RL09、RL09And RL15、RL13And RL15Etc.).
In the formula (L5), RL17、RL18、RL19Each independently represents a linear, branched or cyclic alkyl group having 1 to 15 carbon atoms. Specific examples thereof include: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl, 2-ethylhexyl, n-octyl, 1-adamantyl, 2-adamantyl, and the like.
In the formula (L6), RL20Represents an optionally substituted straight-chain or branched or cyclic alkyl group having 1 to 10 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms, and specifically, RL05The same, etc.
In the formula (L7), RL21Represents an optionally substituted straight-chain or branched or cyclic alkyl group having 1 to 10 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms, and specifically, RL05The same, etc.
RL24Represents a 2-valent group which forms a substituted or unsubstituted cyclopentane, cyclohexane or norbornane ring together with the carbon atom to which it is bonded. RL22、RL23Each independently represents a hydrogen atom or a linear, branched or cyclic 1-valent hydrocarbon group having 1 to 10 carbon atoms. RL22And RL23Or may be bonded to each other and form a ring together with the carbon atom to which they are bonded, and in this case, represents a 2-valent group forming a substituted or unsubstituted cyclopentane ring or cyclohexane ring. p represents 1 or 2.
In the formula (L8), RL25Represents an optionally substituted straight-chain or branched or cyclic alkyl group having 1 to 10 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms, and specifically, RL05The same, etc.
RL28Represents a 2-valent group which forms a substituted or unsubstituted cyclopentane, cyclohexane or norbornane ring together with the carbon atom to which it is bonded. RL26、RL27Each independently represents a hydrogen atom or a linear, branched or cyclic 1-valent hydrocarbon group having 1 to 10 carbon atoms. RL26And RL27Or may be bonded to each other and form a ring together with the carbon atom to which they are bonded, and in this case, represents a 2-valent group forming a substituted or unsubstituted cyclopentane ring or cyclohexane ring. q represents 1 or 2.
In the formula (L9), RL29Represents an optionally substituted straight-chain or branched or cyclic alkyl group having 1 to 10 carbon atoms or an optionally substituted aryl group having 6 to 20 carbon atoms, and specifically, RL05The same, etc.
RL32Means substituted or unsubstituted together with the carbon atom to which they are bondedA cyclopentane ring, a cyclohexane ring or a norbornane ring. RL30、RL31Each independently represents a hydrogen atom or a linear, branched or cyclic 1-valent hydrocarbon group having 1 to 10 carbon atoms. RL30And RL31Or may be bonded to each other and form a ring together with the carbon atom to which they are bonded, and in this case, represents a 2-valent group forming a substituted or unsubstituted cyclopentane ring or cyclohexane ring.
Among the acid-labile groups represented by the above formula (L1), the following groups are specifically exemplified as being linear or branched.
[ solution 19]
Among the acid-labile groups represented by the above formula (L1), the cyclic one is specifically exemplified by: tetrahydrofuran-2-yl, 2-methyltetrahydrofuran-2-yl, tetrahydropyran-2-yl, 2-methyltetrahydropyran-2-yl, and the like.
Specific examples of the acid-labile group of the formula (L2) include: t-butoxycarbonyl, t-butoxycarbonylmethyl, t-pentyloxycarbonyl, t-pentyloxycarbonylmethyl, 1-diethylpropyloxycarbonyl, 1-diethylpropyloxycarbonylmethyl, 1-ethylcyclopentyloxycarbonyl, 1-ethylcyclopentyloxycarbonylmethyl, 1-ethyl-2-cyclopentenyloxycarbonyl, 1-ethyl-2-cyclopentenyloxycarbonylmethyl, 1-ethoxyethoxycarbonylmethyl, 2-tetrahydropyranyloxycarbonylmethyl, 2-tetrahydrofuranyloxycarbonylmethyl and the like.
Specific examples of the acid-labile group of the formula (L3) include: 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, 3-ethyl-1-cyclohexen-3-yl, and the like.
The acid-labile group of the above formula (L4) is particularly preferably a group represented by the following formulae (L4-1) to (L4-4).
[ solution 20]
In the general formulae (L4-1) to (L4-4), the broken lines indicate the bonding positions and bonding directions. RL41Each independently represents a 1-valent hydrocarbon group such as a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms, and specific examples thereof include: methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-pentyl, n-hexyl, cyclopentyl, cyclohexyl and the like.
In the formulae (L4-1) to (L4-4), an enantiomer (enantiomer) or a diastereomer (diasteromer) may be present, and the formulae (L4-1) to (L4-4) represent all of these stereoisomers. These stereoisomers can be used either individually or in the form of mixtures.
For example, the general formula (L4-3) represents a mixture of 1 or 2 selected from the group represented by the following general formula (L4-3-1) and (L4-3-2).
[ solution 21]
The above general formula (L4-4) represents 1 or a mixture of 2 or more selected from the group represented by the following general formulae (L4-4-1) to (L4-4-4).
[ solution 22]
The above-mentioned general formulae (L4-1) to (L4-4), (L4-3-1), (L4-3-2) and (L4-4-1) to (L4-4-4) also represent their enantiomers and mixtures of enantiomers.
Further, high reactivity in the acid catalyst elimination reaction can be achieved by making the bonding directions of (L4-1) to (L4-4), (L4-3-1), (L4-3-2) and (L4-4-1) to (L4-4-4) outward (exo) with respect to the bicyclo [2.2.1] heptane ring, respectively (see Japanese patent application laid-open No. 2000-336121). In the production of these monomers having a tertiary exo-alkyl group having a bicyclo [2.2.1] heptane skeleton as a substituent, there may be a case where a monomer substituted with an inward (endo) alkyl group represented by the following general formulae (L4-1-endo) to (L4-4-endo) is contained, and in order to achieve good reactivity, the exo ratio is preferably 50% or more, and more preferably 80% or more.
[ solution 23]
In the formula, R13Shown and exemplified as RL41The same as above.
Refer to Japanese patent application laid-open No. 2000-336121.
Specific examples of the acid-labile group of the formula (L4) include the following groups.
[ solution 24]
Further, examples of the tertiary alkyl group having 4 to 20 carbon atoms, the trialkylsilyl group having 1 to 6 carbon atoms in each alkyl group, and the oxoalkyl group having 4 to 20 carbon atoms include RL04The same ones as listed above.
Specific examples of the acid-labile group of the formula (L5) include: t-butyl, t-pentyl, and the following groups.
[ solution 25]
Specific examples of the acid-labile group of the formula (L6) include the following groups.
[ solution 26]
Specific examples of the acid-labile group of the formula (L7) include the following groups.
[ solution 27]
Specific examples of the acid-labile group of the formula (L8) include the following groups.
[ solution 28]
Specific examples of the acid-labile group of the formula (L9) include the following groups.
[ solution 29]
Specific examples of the monomer represented by the general formula (a1) include, but are not limited to, those described below.
[ solution 30]
In the formula, R1Represents a hydrogen atom or a methyl group.
[ solution 31]
In the formula, R1Represents a hydrogen atom or a methyl group.
[ solution 32]
In the formula, R1Represents a hydrogen atom or a methyl group.
[ solution 33]
In the formula, R1Represents a hydrogen atom or a methyl group.
In addition to the unit represented by the above general formula (a1), a monomer represented by the following general formulae (a2) to (a4) may be used as necessary for the base resin of the component (a).
[ chemical 34]
In the formula, R1The same as described above. R5And R6Each independently represents a hydrogen atom or a hydroxyl group. Y represents a substituent having a lactone structure or a substituent having a sultone structure. Z represents a hydrogen atom, a fluorinated hydrocarbon group having 1 to 15 carbon atoms, or a substituent of a fluorinated alcohol having 1 to 15 carbon atoms.
Specific examples of the unit represented by the general formula (a2) include, but are not limited to, those described below.
[ solution 35]
Specific examples of the monomer represented by the general formula (a3) include, but are not limited to, those described below.
[ solution 36]
In the formula, R1Represents a hydrogen atom or a methyl group.
[ solution 37]
In the formula, R1Represents a hydrogen atom or a methyl group.
[ solution 38]
In the formula, R1Represents a hydrogen atom or a methyl group.
[ solution 39]
In the formula, R1Represents a hydrogen atom or a methyl group.
Specific examples of the repeating unit represented by the general formula (a4) include, but are not limited to, those described below.
[ solution 40]
In the resist composition of the present invention, monomers having a carbon-carbon double bond other than those described above may be used, for example: substituted acrylates such as methyl methacrylate, methyl crotonate, dimethyl maleate, dimethyl itaconate and the like; unsaturated carboxylic acids such as maleic acid, fumaric acid, and itaconic acid; norborene, norborene derivatives, tetracyclic [ 4.4.0.1%2,5.177,10]Cyclic olefins such as dodecene derivatives; unsaturated acid anhydrides such as itaconic anhydride, alpha-methylene-gamma-butyrolactone, alpha-methyl styrene and other monomers.
The weight average molecular weight (Mw) of the resin A (the base resin of component (A)) is preferably 1,000 to 500,000, more preferably 3,000 to 100,000. If the amount is within the above range, there is no fear that the etching resistance is lowered or the contrast before and after exposure cannot be secured and the resolution is lowered. In the present invention, Mw is a polystyrene-equivalent measured value by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) or Dimethylacetamide (DMF) as a solvent.
In addition, in the case where the molecular weight distribution (Mw/Mn) of the resin a is wide, since both low-molecular-weight and high-molecular-weight polymers are present, foreign substances may be observed on the pattern after exposure, or the pattern shape may be deteriorated. Therefore, since the influence of the molecular weight and the molecular weight distribution tends to be large as the pattern rule becomes finer, the molecular weight distribution of the resin a is preferably 1.0 to 2.0, and a narrow dispersion of 1.0 to 1.5 is particularly preferable in order to obtain a resist composition suitable for a fine pattern size.
Examples of the method for synthesizing the resin a include a method in which a monomer having an unsaturated bond for obtaining the repeating unit represented by the formula (a1) and, if necessary, the repeating unit represented by the formulae (a2) to (a4) or another repeating unit is added to an organic solvent and a radical initiator is added to the organic solvent to carry out thermal polymerization. Examples of the organic solvent used in the polymerization include: toluene, benzene, THF, diethyl ether, dioxane, methyl ethyl ketone, γ -butyrolactone, Propylene Glycol Monomethyl Ether Acetate (PGMEA), and the like. Examples of the polymerization initiator include: 2,2 '-Azobisisobutyronitrile (AIBN), 2' -azobis (2, 4-dimethylvaleronitrile), dimethyl 2, 2-azobis (2-methylpropionate), benzoyl peroxide, lauroyl peroxide and the like. The reaction temperature is preferably 50 to 150 ℃, more preferably 60 to 100 ℃. The reaction time is preferably 2 to 24 hours. The acid-labile group may be introduced into the monomer as it is, or may be protected or partially protected after polymerization. In order to adjust the molecular weight, the polymerization may be carried out using a known chain transfer agent such as dodecyl mercaptan or 2-mercaptoethanol. In this case, the amount of the chain transfer agent to be added is preferably 0.01 to 10 in terms of a molar ratio relative to the total monomers to be polymerized.
In the resin a, the ideal content ratio of each repeating unit derived from each monomer can be set to, for example, the range shown below, but is not limited thereto.
(I) The content of the repeating unit represented by the formula (a1) is preferably 1 to 99 mol%, more preferably 20 to 95 mol%, still more preferably 30 to 90 mol%, and if necessary,
(II) the repeating unit represented by the formula (A-1) is preferably contained in an amount of 1 to 70 mol%, more preferably 5 to 60 mol%, still more preferably 10 to 60 mol%,
(III) at least 1 selected from the repeating units represented by the formulae (A-2) to (A-4) is preferably contained in an amount of 1 to 40 mol%, more preferably 3 to 35 mol%, still more preferably 5 to 30 mol%,
(IV) at least 1 kind selected from the repeating units represented by the formulae (a2) to (a4) is preferably contained in an amount of 0 to 99 mol%, more preferably 0 to 90 mol%, even more preferably 0 to 70 mol%,
the other repeating units (V) are preferably contained in an amount of 0 to 99 mol%, more preferably 0 to 70 mol%, and still more preferably 0 to 50 mol%.
The base resin of component (a) may contain 2 or more resins having different composition ratios, molecular weights, or molecular weight distributions, and may further contain a resin not containing the repeating unit represented by formula (a1) in addition to the resin having the repeating unit having an acid-labile group, as needed.
[ (B) photoacid generators ]
The resist composition of the present invention contains a photoacid generator represented by the following formula (B-1) as a component (B).
[ solution 41]
In the formula, W1Represents a C4-12 hetero atom-containing cyclic 2-valent hydrocarbon group. W2Represents a C4-C14 cyclic 1-valent hydrocarbon group containing no hetero atom. Rf is a 2-valent organic group represented by the general formula1、A2Each independently represents a hydrogen atom or a trifluoromethyl group, B1、B2Each independently represents a hydrogen atom, a fluorine atom or a trifluoromethyl group, and represents an atomic bond to a carbonyloxy group. m represents 0 to 4, and n represents an integer of 0 to 1. M+Represents an onium cation.
W1Specific examples of the heteroatom-containing cyclic 2-valent hydrocarbon group having 4 to 12 carbon atoms include those described below.
[ solution 42]
Represents an atomic bond to an oxycarbonyl group.
Then W1Particularly preferred examples of the cyclic 2-valent hydrocarbon group include a lactone ring structure-containing cyclic 2-valent hydrocarbon group having 6 to 12 carbon atoms. When an acid is generated after exposure, the lactone ring is arranged at a position near the sulfonic acid group, whereby the acid diffusion can be further suppressed.
W2Specific examples of the cyclic 1-valent hydrocarbon group having 4 to 14 carbon atoms and no hetero atom include the following.
[ solution 43]
Broken lines indicate atomic bonds.
W2Preferably a C7-14 hetero atom-free polycyclic 1-valent hydrocarbon group. Then W2Particularly preferred is an adamantyl group. The terminal of the polymer is provided with a highly condensed hydrocarbon group, thereby imparting appropriate solubility.
Rf is a 2-valent organic group represented by the above general formula. Here, A is1、A2Each independently represents a hydrogen atom or a trifluoromethyl group, B1、B2Each independently represents a hydrogen atom, a fluorine atom or a trifluoromethyl group, and represents an atomic bond to a carbonyloxy group. m represents 0 to 4, and n represents an integer of 0 to 1. Preferably m + n>0。
The Rf group is particularly preferably a group selected from the group consisting of the groups represented by the following formulae (Rf-1) to (Rf-6).
[ solution 44]
Represents an atomic bond to a carbonyloxy group.
The photoacid generator represented by the formula (B-1) preferably has such Rf because the solubility is improved by the effect of fluorine atoms and the sulfonic acid generated after exposure has an appropriate acid strength.
Specific examples of the structure of the anion portion of the photoacid generator represented by the formula (B-1) are shown below, but not limited thereto.
[ solution 45]
[ solution 46]
[ solution 47]
In the formula (B-1), M+The onium cation represented by the formula (b1) is preferably at least 1 cation selected from the group consisting of cations represented by the following formulae (b 2).
[ solution 48]
In the formulae (b1) and (b2), R41～R45Each independently is a C1-20 hydrocarbon group which may be straight, branched or cyclic and may contain a hetero atom. And R is41、R42And R43Any 2 of them may also be bonded to each other and form a ring together with the sulfur atom in the formula.
R41～R45The 1-valent hydrocarbon group represented by (a): alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, 4-methylcyclohexyl, cyclohexylmethyl, norbornyl and adamantyl; vinyl, allyl, propenyl, butenyl, hexenyl, cyclohexenylAn alkenyl group; aryl groups such as phenyl, naphthyl, and thienyl; aralkyl groups such as benzyl, 1-phenylethyl and 2-phenylethyl. Among them, aryl is preferable. Further, hydrogen atoms of a part of the 1-valent hydrocarbon group may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, a nitrogen atom, or a halogen atom, and carbon atoms of a part of these groups may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, or a nitrogen atom, and as a result, a hydroxyl group, a cyano group, a carbonyl group, an ether group, an ester group, a sulfonate group, a carbonate group, a lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group, or the like may be contained.
The sulfonium cation represented by the formula (b1) is not limited to the following.
[ solution 49]
[ solution 50]
[ solution 51]
[ solution 52]
[ Hua 53]
[ solution 54]
[ solution 55]
[ solution 56]
Examples of the iodonium cation represented by formula (b2) include the following, but are not limited to this.
[ solution 57]
The resist composition of the present invention may further contain a photoacid generator other than the photoacid generator described above for fine adjustment of the lithographic performance. The other photoacid generator may be any compound that generates an acid upon irradiation with a high-energy ray, and may be any one of those known to be used for known resist compositions, particularly chemically amplified resist compositions. Preferable examples of the other photoacid generator include a sulfonium salt, an iodonium salt, a sulfonyldiazomethane, an N-sulfonyloxyimide, and an oxime-O-sulfonate type acid generator, and 1 kind or more of them may be used alone or in combination. As the acid generated from the other photoacid generator, a strong acid such as sulfonic acid, (bis-perfluoroalkanesulfonyl) imide, (cf. perfluoromethanesulfonyl) methide, or a weak acid such as carboxylic acid is preferable.
Specific examples of other photoacid generators include: the following formulae (B-2), (B-3) and (B-4).
[ solution 58]
In the formula (B-2), A1Is a hydrogen atom or a trifluoromethyl group. R21Can also be used forA linear, branched or cyclic 1-valent hydrocarbon group having 1 to 35 carbon atoms and containing an oxygen atom, a nitrogen-containing heterocyclic group or a group represented by the following formula (i). M+Is an onium cation.
[ chemical 59]
In the formula (i), R31And R32Each independently represents a hydrogen atom, or a straight or branched or cyclic 1-valent hydrocarbon group having 1 to 20 carbon atoms which may contain a hetero atom. R31And R32Or may be bonded to each other and form a ring together with the nitrogen atom to which they are bonded. R33Is a linear, branched or cyclic 2-valent hydrocarbon group having 1 to 20 carbon atoms, which may contain a hetero atom.
R21The 1-valent hydrocarbon group which may contain an oxygen atom is represented by: an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopropylmethyl group, a 4-methylcyclohexyl group, a cyclohexylmethyl group, a norbornyl group, a 1-adamantyl group, or a 1-adamantylmethyl group; a steroid structure-containing group; 2-oxocyclopentyl group, 2-oxocyclohexyl group, 4-oxocyclohexyl group, 2-oxopropyl group, 2-oxoethyl group, 2-cyclopentyl-2-oxoethyl group, 2-cyclohexyl-2-oxoethyl group, 2- (4-methylcyclohexyl) -2-oxoethyl group, 4-oxa-tricyclo [4.2.1.03,7]Oxoalkyl groups such as nonan-5-on-9-yl and 4-oxo-1-adamantyl; phenyl, 1-naphthyl, 2-naphthyl, anthryl, thienyl, 4-hydroxyphenyl, 4-methoxyphenyl, 3-methoxyphenyl, 2-methoxyphenyl, 4-ethoxyphenyl, 4-tert-butoxyphenyl, 3-tert-butoxyphenyl and other alkoxyphenyl groups, 2-methylphenyl, 3-methylphenyl, 4-ethylphenyl, 4-tert-butylphenyl, 4-n-butylphenyl, 2, 4-dimethylphenyl and other alkylphenyl groups, methylnaphthyl, ethylnaphthyl and other alkylnaphthyl groups, methoxynaphthyl, ethoxynaphthyl and other alkoxynaphthyl groups, dimethylnaphthyl, diethylnaphthyl and other dialkylnaphthyl groups, dimethoxynaphthyl, diethoxynaphthyl and other dialkoxynaphthyl groupsAnd the like aryl groups; aralkyl groups such as benzyl, 1-phenylethyl and 2-phenylethyl; and an aryloxyalkyl group such as a 2-aryl-2-oxoethyl group, e.g., a 2-phenyl-2-oxoethyl group, a 2- (1-naphthyl) -2-oxoethyl group, or a 2- (2-naphthyl) -2-oxoethyl group. Other examples include: vinyl, isopropenyl, and the like.
R21The nitrogen-containing heterocyclic group represented by (a) includes: aziridine, pyrrolidine, piperidine, morpholine, pyrrole, pyridine, azetidine (azetine), oxazole, isoxazole, thiazole, isothiazole, imidazole, pyrazole, pyridazine, pyrimidine, pyrazine, pyrroline, 2-imidazoline, imidazolidine, 3-pyrazoline, pyrazolidine, piperazine, triazine, oxadiazine, dithiazine, indole, isoindole, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, 1, 8-naphthyridine, purine, pteridine, indolizine, carbazole, acridine, phenazine, phenanthridine, 1, 10-phenanthroline, phenoxazine, indoline, isoindoline, quinuclidine, benzo [ e]Indole, benzo [ cd ]]Indole.
As R21Particularly preferred examples include: tert-butyl, cyclohexyl, 1-adamantyl, 1-adamantylmethyl, 4-oxa-tricyclo [4.2.1.03,7]Nonan-5-on-9-yl, 4-oxo-1-adamantyl, alkyl groups containing a steroid structure, and the like.
In the formula (i), R31And R32The 1-valent hydrocarbon group represented by (a): an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopropylmethyl group, a 4-methylcyclohexyl group, a cyclohexylmethyl group, a norbornyl group, or an adamantyl group; alkenyl groups such as vinyl, allyl, propenyl, butenyl, hexenyl, and cyclohexenyl; aryl groups such as phenyl, naphthyl, and thienyl; aralkyl groups such as benzyl, 1-phenylethyl and 2-phenylethyl. In addition, in the above-mentioned hydrocarbon group, a part of hydrogen atoms may be substituted with the above-mentioned 1-valent hydrocarbon group, or a group containing a heteroatom such as an oxygen atom, a sulfur atom, a nitrogen atom, a halogen atom, or a part of carbon atoms of these groups may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, a nitrogen atom, and the like, and as a result, a hydroxyl group, a cyano group, a carbonyl group, an ether group, an ester group, a sulfonate group, a carbonate ester group, or the like may be containedA lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group, and the like.
R31And R32When they are bonded to each other and form a ring together with the nitrogen atom to which they are bonded, specific ring types include: aziridine, pyrrolidine, piperidine, morpholine, pyrrole, pyridine, azetidine, oxazole, isoxazole, thiazole, isothiazole, imidazole, pyrazole, pyridazine, pyrimidine, pyrazine, pyrroline, 2-imidazoline, imidazolidine, 3-pyrazoline, pyrazolidine, piperazine, triazine, oxadiazine, dithiazine, indole, isoindole, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, 1, 8-naphthyridine, purine, pteridine, indolizine, carbazole, acridine, phenazine, phenanthridine, 1, 10-phenanthroline, phenoxazine, indoline, isoindoline, quinuclidine, benzo [ e ] e]Indole, benzo [ cd ]]Indole, and the like. Further, hydrogen atoms of a part of these rings may be substituted with the above-mentioned hydrocarbon group or a group containing a heteroatom such as an oxygen atom, a sulfur atom, a nitrogen atom, a halogen atom, or carbon atoms of a part of these rings may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, a nitrogen atom, or the like, and as a result, a hydroxyl group, a cyano group, a carbonyl group, an ether group, an ester group, a sulfonate group, a carbonate group, a lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group, or the like may be contained.
In the formula (i), R33The 2-valent hydrocarbon group represented by (a): linear alkanediyl groups such as methylene, ethylene, propane-1, 3-diyl, butane-1, 4-diyl, pentane-1, 5-diyl, hexane-1, 6-diyl, heptane-1, 7-diyl, octane-1, 8-diyl, nonane-1, 9-diyl, decane-1, 10-diyl, undecane-1, 11-diyl, dodecane-1, 12-diyl, tridecane-1, 13-diyl, tetradecane-1, 14-diyl, pentadecane-1, 15-diyl, hexadecane-1, 16-diyl and heptadecane-1, 17-diyl; a branched alkanediyl group in which a side chain such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, or a tert-butyl group is added to the linear alkanediyl group; saturated cyclic hydrocarbon groups such as cyclopentanediyl, cyclohexanediyl, norbornanediyl and adamantanediyl groups; unsaturated cyclic 2-valent hydrocarbon groups such as phenylene and naphthylene. Further, some of the hydrogen atoms of these groups may be substituted with a group containing an oxygen atom, a sulfur atom, a nitrogen atom, a halogenA group containing a heteroatom such as an atom, or a group containing a heteroatom such as an oxygen atom, a sulfur atom, or a nitrogen atom inserted into a carbon atom of a part of these groups, and as a result, may contain a hydroxyl group, a cyano group, a carbonyl group, an ether group, an ester group, a sulfonate group, a carbonate group, a lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group, or the like.
Specific examples of the structure of the anion portion of the photoacid generator represented by the formula (B-2) are shown below, but not limited thereto. In the following formula, A1As before.
[ solution 60]
[ solution 61]
In the formula (B-2), M+The onium cation represented by the formula (b1) is preferably at least 1 cation selected from the group consisting of cations represented by the formula (b 2).
In the formula (B-3), A2Is a hydrogen atom or a trifluoromethyl group. R22、R23And R24Each independently represents a hydrogen atom, or a straight or branched or cyclic 1-valent hydrocarbon group having 1 to 20 carbon atoms which may contain a hetero atom. p and q are each independently an integer of 0 to 5. r is an integer of 0 to 4. L is a single bond, an ether group, or a straight chain, branched or cyclic 2-valent hydrocarbon group having 1 to 20 carbon atoms which may contain a hetero atom.
R22、R23And R24The 1-valent hydrocarbon group represented by (a): methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-pentyl, n-hexyl, n-octyl, n-nonyl, n-decyl, cyclopentyl, cyclohexyl, 2-ethylhexyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylbutyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylbutyl, norbornyl, oxanorbornyl, tricyclo [5.2.1.02,6]Alkyl groups such as decyl and adamantyl.Further, some of the hydrogen atoms of these groups may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, a nitrogen atom, or a halogen atom, or some of the carbon atoms of these groups may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, or a nitrogen atom, and as a result, a hydroxyl group, a cyano group, a carbonyl group, an ether group, an ester group, a sulfonate group, a carbonate group, a lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group, or the like may be contained. R22、R23And R24Methyl, methoxy, t-butyl, t-butoxy and the like are preferable.
In the formula (B-3), the 2-valent hydrocarbon group represented by L is exemplified and exemplified as R33Similarly, a combination of 2 or more of these groups may be used. Further, some of the hydrogen atoms of these groups may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, a nitrogen atom, or a halogen atom, or some of the carbon atoms of these groups may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, or a nitrogen atom, and as a result, a hydroxyl group, a cyano group, a carbonyl group, an ether group, an ester group, a sulfonate group, a carbonate group, a lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group, or the like may be contained.
The photoacid generator represented by the formula (B-3) includes, but is not limited to, those described below. In the following formula, A2As before.
[ solution 62]
[ solution 63]
(B) The photoacid generator may further contain a compound represented by the above formula (B-4). In the formula (B-4), A3And A4Are each independently a hydrogen atom or a trifluoromethyl group, and are not both hydrogen atoms. R25Is a straight chain or branched or cyclic ring which may also contain an oxygen atomA C1-C35 1-valent hydrocarbon group, a nitrogen-containing heterocyclic group, or a group represented by the formula (i). M+As with the onium cations described above.
Specific examples of the structure of the anion portion of the photoacid generator represented by the formula (B-4) are shown below, but not limited thereto.
[ solution 64]
[ solution 65]
Among the other photoacid generators, compounds having a fluorine atom-containing structure represented by a trifluoromethyl group as an anion structure have high hydrophobicity and are less likely to elute into the wetting water. Further, since the composition has a structure containing a fluorine atom, the solubility in a solvent is high, and the residue after development can be reduced in the case of organic solvent development. This can reduce defects after development, and is suitable as a resist composition for ArF immersion exposure.
Specific examples of the photoacid generator other than the photoacid generator include, for example: particularly preferred examples of the compounds described in paragraphs [0122] to [0142] of Japanese patent laid-open No. 2008-111103 include: the compounds described in paragraphs [0088] to [0092] of Japanese patent application laid-open No. 2014-001259, the compounds described in paragraphs [0015] to [0017] of Japanese patent application laid-open No. 2012-41320, the compounds described in paragraphs [0015] to [0029] of Japanese patent application laid-open No. 2012-106986, and the like. The partially fluorinated sulfonic acid-generating photoacid generator described in the above publication is preferably used, particularly in ArF lithography, because the intensity and diffusion distance of the generated acid are appropriate.
(B) The content of the photoacid generator of component (A) is preferably 0.1 to 50 parts by mass, more preferably 0.2 to 40 parts by mass, and still more preferably 0.3 to 35 parts by mass, based on 100 parts by mass of the base resin of component (A). If the amount is within the above range, the resolution is not deteriorated, and there is no fear that foreign matter is generated after development and when peeling of the resist film. The amount of the compound represented by the formula (B-4) to be added is preferably 0 to 50% by mass of the photoacid generator of the component (B).
[ (C) solvent ]
The resist composition of the present invention contains a solvent as the component (C). The aforementioned solvents include: ketones such as cyclohexanone and methyl-2-n-amyl ketone described in paragraphs [0144] to [0145] of Japanese patent laid-open No. 2008-111103; alcohols such as 3-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, and 1-ethoxy-2-propanol; ethers such as propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, and diethylene glycol dimethyl ether; esters such as PGMEA, propylene glycol monoethyl ether acetate, ethyl lactate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, t-butyl acetate, t-butyl propionate, and propylene glycol mono-t-butyl ether acetate; lactones such as γ -butyrolactone and ketone alcohols such as diacetone alcohol; a mixed solvent thereof. When an acetal acid-labile group is used, an alcohol solvent having a high boiling point may be added to accelerate the deprotection reaction of acetal, specifically, diethylene glycol, propylene glycol, glycerin, 1, 4-butane diol, 1, 3-butane diol, or the like may be added.
(C) The content of the solvent of component (A) is preferably 100 to 10,000 parts by mass, more preferably 300 to 8,000 parts by mass, based on 100 parts by mass of the base resin of component (A).
[ (D) fluorine-containing resin ]
The resist composition of the present invention may contain a resin different from the resin A and at least 1 kind of fluorine-containing resin selected from the group consisting of repeating units represented by the following formulae (D-1), (D-2) and (D-3).
[ solution 66]
In the formula, RAIs a hydrogen atom or a methyl group. R51And R52Each independently being a hydrogen atom, or linear, branched or cyclicA C1-valent hydrocarbon group having 1 to 10 carbon atoms. R53Is a single bond, or a straight or branched 2-valent hydrocarbon group having 1 to 5 carbon atoms. R54、R55And R56Each independently represents a hydrogen atom, or a linear, branched or cyclic 1-valent hydrocarbon group having 1 to 15 carbon atoms, a fluorinated 1-valent hydrocarbon group, an acyl group or an acid-labile group. R54、R55And R56In the case of a 1-valent hydrocarbon group or a fluorinated 1-valent hydrocarbon group, a part of carbon atoms thereof may be substituted with ether groups or carbonyl groups. R57Is a linear, branched or cyclic (v +1) -valent hydrocarbon group or fluorinated hydrocarbon group having 1 to 20 carbon atoms. v is an integer of 1 to 3.
R51And R52The 1-valent hydrocarbon group having 1 to 10 carbon atoms includes: and alkyl groups such as methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, adamantyl, and norbornyl. Among them, a C1-6 linear, branched or cyclic 1-valent hydrocarbon group is preferable.
R53Specific examples of the C1-5 2-valent hydrocarbon group include: methylene, ethylene, trimethylene, propylene, tetramethylene, pentamethylene, and the like.
R54、R55And R56The 1-valent hydrocarbon group having 1 to 15 carbon atoms includes: alkyl, alkenyl, alkynyl and the like, preferably alkyl. The alkyl group includes, in addition to the above, n-undecyl, n-dodecyl, tridecyl, tetradecyl, pentadecyl, and the like. Examples of the fluorinated 1-valent hydrocarbon group having 1 to 15 carbon atoms include groups in which some or all of the hydrogen atoms bonded to the carbon atoms of the 1-valent hydrocarbon group are substituted with fluorine atoms. As described above, a part of the carbon atoms may be substituted with an ether group or a carbonyl group.
R54、R55And R56In the case of an acid-labile group, specific examples thereof include: groups represented by the above formulae (L1) to (L9), tertiary alkyl groups having 4 to 20 carbon atoms, preferably 4 to 15 carbon atoms, trialkylsilyl groups wherein each alkyl group is an alkyl group having 1 to 6 carbon atoms, oxoalkyl groups having 4 to 20 carbon atoms, and the like.
R57Examples of the (v +1) -valent hydrocarbon group or fluorinated hydrocarbon group having 1 to 20 carbon atoms include groups obtained by removing a necessary number of hydrogen atoms from the 1-valent hydrocarbon group or fluorinated 1-valent hydrocarbon group.
The repeating unit represented by the formula (D-1) may be, but is not limited to, the following. In the following formula, RAAs before.
[ solution 67]
The repeating unit represented by the formula (D-2) may be, but is not limited to, the following. In the following formula, RAAs before.
[ solution 68]
The repeating unit represented by the formula (D-3) may be, but is not limited to, the following. In the following formula, RAAs before.
[ solution 69]
(D) The Mw of the fluorine-containing resin of component (B) is preferably 1,000 to 100,000, more preferably 3,000 to 15,000. The Mw/Mn is preferably 1.0 to 2.0, more preferably 1.0 to 1.6.
In the case of synthesizing the fluorine-containing resin of the component (D), 1 method may be a method of adding a radical initiator to an organic solvent to carry out thermal polymerization of a monomer having an unsaturated bond for obtaining the repeating units represented by the formulae (D-1) to (D-3) and, if necessary, other repeating units. Examples of the organic solvent used in the polymerization include: toluene, benzene, THF, diethyl ether, dioxane, methyl ethyl ketone, propylene glycol monomethyl ether acetate, and the like. Examples of the polymerization initiator include: AIBN, 2' -azobis (2, 4-dimethylvaleronitrile), dimethyl 2, 2-azobis (2-methylpropionate), benzoyl peroxide, lauroyl peroxide and the like. The reaction temperature is preferably 50 to 100 ℃. The reaction time is preferably 4 to 24 hours. The acid-labile group may be introduced into the monomer as it is, or may be protected or partially protected after polymerization. In order to adjust the molecular weight, the polymerization may be carried out using a known chain transfer agent such as dodecyl mercaptan or 2-mercaptoethanol. In this case, the amount of the chain transfer agent to be added is preferably 0.01 to 10 in terms of a molar ratio relative to the total monomers to be polymerized.
When the resist composition of the present invention contains the fluorine-containing resin of component (D), the content thereof is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 10 parts by mass, based on 100 parts by mass of the base resin of component (A). When the content is in the above range, the contact angle between the surface of the resist film and water can be sufficiently improved, and defects due to the residual wetting water, or elution of the acid generator or the quencher can be suppressed. In addition, the solubility of the surface of the resist film can be adjusted, and good dimensional uniformity can be achieved.
[ other ingredients ]
The resist composition of the present invention may also contain an amine compound, a sulfonate salt, or a carboxylate salt as a quencher, as required. In the present specification, the quencher means a compound which can suppress the diffusion rate when an acid generated from the photoacid generator diffuses in the resist film.
Among such quenchers, examples of amine compounds include primary, secondary or tertiary amine compounds described in paragraphs [0146] to [0164] of Japanese patent application laid-open No. 2008-111103, and particularly preferred examples thereof include amine compounds having any of a hydroxyl group, an ether group, an ester group, a lactone ring, a cyano group, a sulfonate group, and the like. Further, there may be mentioned compounds in which a primary or secondary amine is protected as a carbamate group, as in the compound described in Japanese patent No. 3790649. Such a protected amine compound is effective when there is a component unstable to alkali in the resist composition.
The sulfonate is exemplified by a compound represented by the following formula (Z1). The carboxylate may be a compound represented by the following formula (Z2).
[ solution 70]
R101A hydrogen atom or a hydrocarbon group of 1 to 40 carbon atoms which may contain a hetero atom, wherein the hydrogen atom excluding the carbon atom bonded to the alpha-position of the sulfo group is substituted with a fluorine atom or a fluoroalkyl group. M+Each independently is an onium cation, and the same as those exemplified above can be exemplified.
The hydrocarbon group may be saturated or unsaturated, and may be linear, branched or cyclic. Specific examples thereof include: an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-pentyl group, a n-hexyl group, a n-octyl group, a 2-ethylhexyl group, a n-nonyl group, or a n-decyl group; cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylbutyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylbutyl, norbornyl, tricyclo [5.2.1.02,6]Cyclic saturated hydrocarbon groups such as decyl, adamantyl, and adamantylmethyl groups; examples of the alkenyl group include alkenyl groups such as vinyl, allyl, propenyl, butenyl and hexenyl; unsaturated alicyclic hydrocarbon groups such as cyclohexenyl groups; aryl groups such as phenyl, naphthyl, alkylphenyl (e.g., 2-methylphenyl, 3-methylphenyl, 4-ethylphenyl, 4-tert-butylphenyl and 4-n-butylphenyl), dialkylphenyl (e.g., 2, 4-dimethylphenyl and 2,4, 6-triisopropylphenyl), alkylnaphthyl (e.g., methylnaphthyl and ethylnaphthyl), and dialkylnaphthyl (e.g., dimethylnaphthyl and diethylnaphthyl); heteroaryl groups such as thienyl; aralkyl groups such as benzyl, 1-phenylethyl and 2-phenylethyl.
Further, some of the hydrogen atoms of these groups may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, a nitrogen atom, or a halogen atom, and some of the carbon atoms of these groups may be substituted with a group containing a heteroatom such as an oxygen atom, a sulfur atom, or a nitrogen atom, and as a result, a hydroxyl group, a cyano group, a carbonyl group, an ether bond, an ester bond, a sulfonate bond, a carbonate bond, a lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group, or the like may be contained. Examples of the hydrocarbon group containing a hetero atom include: an alkoxyphenyl group such as a 4-hydroxyphenyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 4-tert-butoxyphenyl group, or 3-tert-butoxyphenyl group; alkoxynaphthyl such as methoxynaphthyl, ethoxynaphthyl, n-propoxytenyl and n-butoxynaphthyl; dialkoxynaphthyl groups such as dimethoxynaphthyl and diethoxynaphthyl; and an aryl-side oxyalkyl group such as a 2-aryl-2-oxoethyl group, e.g., a 2-phenyl-2-oxoethyl group, a 2- (1-naphthyl) -2-oxoethyl group, and a 2- (2-naphthyl) -2-oxoethyl group.
R102The hydrocarbon group may contain a hetero atom and has 1 to 40 carbon atoms. R102The hydrocarbyl group represented is exemplified and exemplified by R101The same applies to the hydrocarbon group. Further, other specific examples include: fluorine-containing alkyl groups such as trifluoromethyl, trifluoroethyl, 2,2, 2-trifluoro-1-methyl-1-hydroxyethyl, and 2,2, 2-trifluoro-1- (trifluoromethyl) -1-hydroxyethyl; and a fluorine-containing aryl group such as a pentafluorophenyl group or a 4-trifluoromethylphenyl group.
The sulfonate salt represented by the formula (Z1) includes, but is not limited to, those shown below.
[ solution 71]
[ chemical formula 72]
The carboxylate represented by the formula (Z2) includes, but is not limited to, those shown below.
[ solution 73]
When the resist composition of the present invention contains the above-mentioned quencher, the content thereof is preferably 0.001 to 12 parts by mass, more preferably 0.01 to 8 parts by mass, based on 100 parts by mass of the base resin of the component (A). The incorporation of the quencher facilitates the adjustment of the sensitivity of the resist, and also suppresses the diffusion rate of acid in the resist film to improve the resolution, suppresses the change in sensitivity after exposure, or reduces the dependence on the substrate or the environment to improve the exposure latitude, the pattern profile, and the like. Further, by adding these quenchers, the substrate adhesion can be improved. The aforementioned quenching agents may be used singly in 1 kind or in combination in 2 or more kinds.
[ surfactant ]
The resist composition of the present invention may contain a surfactant which is insoluble or hardly soluble in water and soluble in an alkali developer and/or a surfactant component which is insoluble or hardly soluble in water and an alkali developer. The surfactant can be defined as the component (S) described in Japanese patent application laid-open Nos. 2010-215608 and 2011-16746.
As the surfactant which is insoluble or hardly soluble in water and an alkali developing solution, among the surfactants described in the above-mentioned publications, FC-4430 (manufactured by 3M Co., Ltd.), SURLON (registered trademark) S-381 (manufactured by AGC SEIMI CHEMICAL Co., Ltd.), SURFYNOL (registered trademark) E1004 (manufactured by AIR PRODUCTS Co., Ltd.), KH-20, KH-30 (manufactured by Asahi glass (Strand Co., Ltd.), and an oxetane ring-opening polymer represented by the following structural formula (surf-1) are preferable. These can be used alone in 1 or a combination of 2 or more.
[ chemical formula 74]
However, Rf, R, M, A, B, C and N in the above formula are applicable only to this formula.
In the formula (surf-1), R is an aliphatic group having 2 to 4 valences and 2 to 5 carbon atoms, and specifically, the aliphatic group having 2 valences includes: ethylene, tetramethylene, propylene, 2-dimethyl-1, 3-propanediyl, pentamethylene and the like, and those having a valence of 3 or 4 include those shown below.
[ solution 75]
In the formula, broken lines represent atomic bonds and are partial structures derived from glycerin, trimethylolethane, trimethylolpropane, and neopentyltetraol, respectively.
Among them, tetramethylene group or 2, 2-dimethyl-1, 3-propanediyl group is preferably used. Rf is trifluoromethyl or pentafluoroethyl, preferably trifluoromethyl. M is an integer of 0 to 3, N is an integer of 1 to 4, and the sum of M and N represents the valence of R and is an integer of 2 to 4. A is 1, B is an integer of 2 to 25, and C is an integer of 0 to 10. B is preferably an integer of 4 to 20, and C is preferably 0 or 1. The arrangement of the constituent units of the above structure is not limited, and the blocks may be randomly bonded. The surfactant of partially fluorinated oxetane ring-opening polymer system can be produced, for example, as described in U.S. Pat. No. 5650483.
[ Pattern Forming method ]
The present invention further provides a pattern forming method using the resist composition. When the resist composition of the present invention is used to form a pattern, a known photolithography technique can be used. Specifically, the resist composition of the present invention is applied to a substrate (Si, SiO) for integrated circuit production by a method such as spin coating2SiN, SiON, TiN, WSi, BPSG, SOG, organic anti-reflection film, etc.), or a substrate for manufacturing a mask circuit (Cr, CrO, CrON, MoSi)2、SiO2Etc.) to a film thickness of 0.05 to 2 μm, and then prebaking it on a hot plate preferably at 60 to 150 ℃ for 1 to 10 minutes, more preferably at 80 to 140 ℃ for 1 to 5 minutes to form a resist film.
Then, a mask for forming a desired pattern is masked on the resist film, and irradiated with high-energy rays such as KrF excimer laser, ArF excimer laser, EUV and EB with a wavelength of 3 to 15nm, preferably at an exposure of 1 to 200mJ/cm2Is 10 to 100mJ/cm2More preferably, it is 0.1 to 100. mu.C/cm2Is 0.5 to 50 μ C/cm2More preferably. The exposure may be performed by a normal exposure method, or by interposing a liquid having a refractive index of 1.0 or more between the resist film and the projection lensThe immersion method of (4). A water-insoluble protective film may also be used at this time. Then, a post-exposure bake (PEB) is performed on the hot plate at 60 to 150 ℃ for 1 to 5 minutes, preferably 80 to 140 ℃ for 1 to 3 minutes. Then, a developing solution of an aqueous alkali solution such as tetramethylammonium hydroxide (TMAH) is used in an amount of preferably 0.1 to 5% by mass, more preferably 2 to 3% by mass, or a developing solution of an organic solvent such as butyl acetate is used to perform development for preferably 0.1 to 3 minutes, more preferably 0.5 to 2 minutes by a common method such as a dip (dip) method, a dip (paddle) method, or a spray (spray) method, thereby forming a desired pattern on the substrate.
The water-insoluble protective films are used for preventing the elution from the resist film and for improving the water-repellency of the film surface, and are roughly classified into 2 types. One is an organic solvent peeling type requiring peeling with an organic solvent that does not dissolve the resist film before alkali development, and the other is an alkali-soluble type that is soluble in an alkali developing solution and removes the protective film together when removing the resist film-soluble portion. The latter is particularly preferred to be a material obtained by dissolving a polymer compound having a1, 1,1,3,3, 3-hexafluoro-2-propanol residue, which is insoluble in water and soluble in an alkali developer, in an alcohol solvent having 4 or more carbon atoms, an ether solvent having 8 to 12 carbon atoms, or a mixed solvent thereof. The surfactant insoluble in water and soluble in an alkali developer may be dissolved in an alcohol solvent having 4 or more carbon atoms, an ether solvent having 8 to 12 carbon atoms, or a mixed solvent thereof.
In the pattern forming method, the extraction of an acid generator or the like from the film surface or the flow washing of fine particles may be performed by performing a pure water rinse (postsoak) after the formation of the photoresist film, or a rinse (postsoak) for removing water remaining on the film after exposure may be performed.
In addition, as described above, the developing solution for the pattern forming method of the present invention may be an alkaline aqueous solution such as TMAH, preferably in an amount of 0.1 to 5% by mass, more preferably 2 to 3% by mass, but an organic solvent may be used. At this time, negative tone development for developing/dissolving the unexposed portion may be performed.
In the organic solvent development, a compound selected from the group consisting of 2-octanone, 2-nonanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-hexanone, 3-hexanone, diisobutyl ketone, methylcyclohexanone, acetophenone, methylacetophenone, propyl acetate, butyl acetate, isobutyl acetate, amyl acetate, butenyl acetate, isoamyl acetate, phenyl acetate, propyl formate, butyl formate, isobutyl formate, amyl formate, isoamyl formate, methyl valerate, methyl pentenoate, methyl crotonate, ethyl crotonate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, isobutyl lactate, amyl lactate, isoamyl lactate, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate, methyl benzoate, ethyl benzoate, benzyl acetate, methyl phenylacetate, methyl lactate, And 1 or more of benzyl formate, phenylethyl formate, methyl 3-phenylpropionate, benzyl propionate, ethyl phenylacetate, and 2-phenylethyl acetate as developer.
Examples
The present invention will be specifically described below by way of examples and comparative examples, but the present invention is not limited to the following examples.
[1] Synthesis of photoacid generators (PAGs)
[ example 1-1]
[ 76]
100g of ammonium salt 1, 68.7g of cationic intermediate 1, 100g of pure water and 400g of methylene chloride were mixed and then aged for 1 hour with stirring. After the organic layer was separated and extracted, the mixture was washed 2 times with a mixed solution of 5.7g of the cationic intermediate 1 and 100g of pure water, further washed 5 times with 100g of pure water, and further washed 2 times with 100g of a 20 wt% methanol aqueous solution. The resulting organic layer was concentrated, PGMEA was added and concentrated again to make a 20 wt% PGMEA solution. The resulting PGMEA solution was stirred at room temperature overnight to precipitate a solid, and then 500g of hexane was added thereto and stirred for 2 hours. The obtained solid was subjected to filtration, washed with 200g of hexane, and finally dried under reduced pressure by heating at 50 ℃ to obtain 104.8g of the objective PAG1 (yield 88%). Of the resulting PAG11The HNMR is shown in figure 1,19FNMR is shown in FIG. 2.
IR(D-ATR)：ν＝3087,3002,2906,2852,1785,1727,1477,1448,1344,1240,1180,1103,1076,1035,1010,997,943,750,684,642,551,522,501cm-1
[ examples 1-2]
[ solution 77]
417g of ammonium salt 2, 268g of cationic intermediate 2, 1400g of pure water and 2000g of methylene chloride were mixed, and then stirred and aged for 1 hour. After separating and extracting the organic layer, the organic layer was washed 6 times with 600g of pure water and then 6 times with 600g of 20 wt% aqueous methanol solution. To the resulting organic layer was added 25g of activated carbon, and the mixture was stirred at room temperature overnight. After removing the activated carbon by filtration, the organic layer was washed 1 time with 600g of 1% hydrochloric acid, 2 times with 600g of pure water, 1 time with 600g of 1% hydrochloric acid, and 3 times with 600g of pure water. Further, the plate was washed 1 time with 600g of 0.04eq. ammonia water, then 3 times with 600g of pure water, then 1 time with 600g of 0.5% hydrochloric acid, and then 3 times with 600g of pure water. The organic layer was concentrated, PGMEA was added and concentrated again to make a 50 wt% PGMEA solution. The concentrated solution was added dropwise to 3.5L of diisopropyl ether to precipitate crystals. After stirring for 1 hour, it was filtered off and rinsed with diisopropyl ether and finally dried under reduced pressure by heating at 50 ℃ to obtain 535g of the desired PAG2 (yield 86%). Of the resulting PAG21The HNMR is shown in figure 3,19FNMR is shown in FIG. 4.
IR(D-ATR)：ν＝3089,2907,2853,1785,1729,1476,1449,1344,1237,1180,1104,1076,1035,1010,947,761,707,681,642,585,551,525cm-1
[ examples 1-3 to 1-9] Synthesis of other PAGs (PAG-3 to PAG-9)
PAG-3 to PAG-9 were synthesized by a known organic synthesis method using the corresponding starting materials.
[ solution 78]
[2] Synthesis of polymers
The polymer used in the resist composition of the present invention was synthesized by the following method. The Mw of the obtained polymer is a polystyrene equivalent value measured by GPC using THF or DMF as a solvent.
Synthesis example 1 Synthesis of resist Polymer 1
[ solution 79]
P-hydroxystyrene (27.8g), 1-methylcyclopentyl methacrylate (72.2g) and dimethyl 2,2' -azobisisobutyrate (6.08g) were dissolved in PGMEA (155g) under a nitrogen atmosphere to prepare a solution. The solution was added dropwise to PGMEA (78g) stirred at 80 ℃ under nitrogen atmosphere over 6 hours. After completion of the dropwise addition, the mixture was stirred for 2 hours while maintaining a temperature of 80 ℃ and cooled to room temperature, and then the reaction solution was dropwise added to n-hexane (3000 g). The precipitated solid was separated by filtration, and dried under vacuum at 50 ℃ for 20 hours to obtain a resist polymer 1 as a white powdery solid. The yield was 85g, 85%.
Synthesis examples 2 to 7 Synthesis of resist polymers 2 to 7
Resist polymers 2 to 7 shown below were produced in the same manner as in Synthesis example 1 except that the kinds and blending ratios of the monomers were changed.
[ solution 80]
[3] Preparation of resist composition
Examples 2-1 to 2-40 and comparative examples 1-1 to 1-38
Onium salts (PAG-1 to PAG-9) of the present invention, comparative photoacid generators PAG-A to PAG-H, resist polymers 1 to 7, other photoacid generators PAG-X to PAG-Z, quenchers Q-1 to Q-4, and alkali-soluble surfactant SF-1 were dissolved in a solvent containing 0.01 mass% of surfactant A (manufactured by OMNOVA) to prepare a solution having the composition shown in tables 1 and 2, and the solution was filtered through a 0.2 μm Teflon (registered trademark) filter to prepare a resist composition.
[ Table 1]
[ Table 2]
In tables 1 and 2, the solvents, the comparative photoacid generators PAG-A to PAG-H, the other photoacid generators PAG-X to PAG-Z, the quenchers Q-1 to Q-4, and the alkali-soluble surfactant (fluoropolymer) SF-1 are as follows.
·PAG-A～PAG-H：
[ solution 81]
·PAG-X～PAG-Z：
[ solution 82]
·SF-1：
[ solution 83]
·Q-1～Q-4：
[ solution 84]
Solvent:
s-1: PGMEA (propylene glycol monomethyl ether acetate)
S-2: GBL (gamma-butyrolactone)
Surfactant a:
3-methyl-3- (2,2, 2-trifluoroethoxymethyl) oxetane-tetrahydrofuran-2, 2-dimethyl-1, 3-propanediol copolymer (OMNOVA Co., Ltd.)
[ solution 85]
a: (b + b'): (c + c') is 1: 4-7: 0.01 to 1 (molar ratio)
Mw＝1,500
[4] Evaluation of resist composition: evaluation of EUV Exposure patterning (evaluation of hole Pattern)
Examples 3-1 to 3-40 and comparative examples 2-1 to 2-38
The resist compositions (R-1 to R-40) of the present invention and the comparative resist compositions (R-41 to R-78) were applied to a substrate of an organic anti-reflective coating AL-412 made by BRUWER SCIENCE having a film thickness of 20nm using CLEAN TRACK Lithius ProZ made by Tokyo Wikipedia, and baked on a hot plate at 105 ℃ for 60 seconds to form a 50nm resist film. An EUV exposure machine NXE3300 manufactured by ASML corporation was used to expose a lattice pattern of 27.5nm at a pitch of 46nm in size on a mask, after exposure, PEB temperature suitable for each resist composition was applied, 2.38% tetramethylammonium aqueous solution was sprayed while the wafer was rotated, development was performed for 30 seconds in total, the aqueous solution was washed off with water, and the wafer was rotated at a high speed to remove water.
[ evaluation of sensitivity ]
The resist pattern was observed with CD-SEM CG-5000 manufactured by Hitachi advanced technology, and the exposure dose at which the hole diameter became 23nm at a pitch of 46nm was used as the optimum exposure dose Eop (mJ/cm)2)。
[ MEF evaluation ]
When the dimension on the mask was 46nm in pitch and the lattice pattern was 27.5nm and the hole diameter around 23nm was observed by CD-SEM, the CD of the hole pattern was measured at 46nm in pitch and at 26.0nm, 26.5nm, 27.0nm, 27.5nm, 28.0nm, 28.5nm and 29.0nm in lattice pattern on the mask. The size on the mask and the slope of this observed CD are taken as mef (mask Error Enhancement factor). MEF is defined as good below about 3.0.
[ evaluation of dimensional uniformity (CDU) ]
In the hole pattern observed by CD-SEM CG-5000 manufactured by hitachi front-end technology, the hole diameter was measured at 32 points for 1 hole per 1 sample, 49 holes were measured from 1 SEM image, and the value (3 σ) of 3 times the standard deviation (σ) calculated from the result was obtained to obtain 30 SEM images, and the average value of the standard deviation was defined as CDU. The smaller the value of CDU means the more excellent the dimensional uniformity. About 3.2 or less is defined as CDU good.
[ Table 3]
[ Table 4]
From the results shown in table 3, it is understood that the resist composition of the present invention (examples) is excellent in sensitivity and MEF and CDU. On the other hand, as shown in Table 4, the resist compositions (comparative examples) using PAG-A to PAG-E (see patent documents 1 to 4) which are known types of photoacid generators and PAG-F, PAG-H, W2 which contains no heteroatom and PAG-G, PAG-H which contains heteroatom W1 were insufficient in MEF and CDU. As described above, the resist composition of the present invention is particularly suitable as a material for EUV lithography.
The present invention is not limited to the above embodiment. The above-described embodiments are illustrative, and have substantially the same configuration as the technical idea described in the claims of the present invention, and all of the embodiments that exhibit the same effects are intended to be included in the technical scope of the present invention.
Claims (12)
1. A resist composition characterized by comprising:
(A) a resin containing a repeating unit having an acid-labile group and further containing at least 1 repeating unit having an aromatic substituent,
(B) a photoacid generator represented by the general formula (B-1), and
(C) a solvent;
in the formula, W1A C4-C12 hetero atom-containing cyclic 2-valent hydrocarbon group; w2Represents a C4-14 hetero-atom-free cyclic 1-valent hydrocarbon group; rf is a 2-valent organic group represented by the general formula1、A2Each independently represents a hydrogen atom or a trifluoromethyl group, B1、B2Each independently represents a hydrogen atom, a fluorine atom or a trifluoromethyl group, represents an atomic bond with a carbonyloxy group; m represents 0 to 4, n represents an integer of 0 to 1; m+Represents an onium cation.
2. Resist composition according to claim 1, whichW in the general formula (B-1)1Is a C6-12 cyclic 2-valent hydrocarbon group containing a lactone ring structure.
3. The resist composition according to claim 1 or 2, wherein W in the general formula (B-1)2Is a C7-C14 polycyclic C1-valent hydrocarbon group containing no hetero atom.
4. The resist composition according to claim 1 or 2, wherein the Rf group in the general formula (B-1) is selected from the group represented by the following formulae (Rf-1) to (Rf-6);
represents an atomic bond to a carbonyloxy group.
5. The resist composition according to claim 1 or 2, wherein in the resin of component (a), 1 of the repeating units having an aromatic substituent is a repeating unit represented by the following formula (a-1);
in the formula, RARepresents a hydrogen atom or a methyl group; r61Represents a hydrogen atom, or a straight chain, branched or cyclic hydrocarbon group having 1 to 10 carbon atoms and into which a hetero atom may be inserted; r62Represents a C1-C8 linear, branched or cyclic hydrocarbon group which may have a heteroatom inserted therein; t is an integer of 1-3, and u is an integer satisfying u being less than or equal to 5+2 s-t; s is 0 or 1; l is1Represents a single bond or any of-C (═ O) O-, -C (═ O) NH-.
6. The resist composition according to claim 1 or 2, wherein in the resin of component (a), 1 of the repeating units having an aromatic substituent is a repeating unit represented by the following general formulae (a-2) to (a-4);
in the formula, RAEach independently is a hydrogen atom or a methyl group, R201Is a single bond, phenylene, -O-R210-, or-C (═ O) -Z2-R210-；Z2Is oxygen atom or NH, R210Is a linear, branched or cyclic alkylene, alkenylene or phenylene group having 1 to 6 carbon atoms, and may contain a carbonyl group (-CO-), an ester group (-COO-), an ether group (-O-) or a hydroxyl group; l is2Represents a single bond, or-Z3-C(＝O)-O-，Z3Represents a C1-20 linear, branched or cyclic 2-valent hydrocarbon group which may be substituted with a hetero atom; z1Is a single bond, methylene, ethylene, phenylene, fluorinated phenylene, -O-R211-, or-C (═ O) -Z4-R211-；Z4Is oxygen atom or NH, R211Is a linear, branched or cyclic alkylene, alkenylene or phenylene group having 1 to 6 carbon atoms, and may contain a carbonyl group, an ester group, an ether group or a hydroxyl group; m-Represents a non-nucleophilic counter ion; r202、R203、R204、R205、R206、R207、R208、R209Independently represents a C1-20 straight chain or branched or cyclic C3-20 hydrocarbon group which may be substituted with a hetero atom or may be interrupted by a hetero atom; and R is202And R203Or may be bonded to each other and form a ring together with the sulfur atom in the formula, or R204、R205And R206Or R is 2 or more of207、R208And R209Any 2 or more of them may be bonded to each other and form a ring together with the sulfur atom in the formula; however, the repeating units represented by the general formulae (A-2) to (A-4) have 1 or more aromatic substituents.
7. The resist composition according to claim 1 or 2, further comprising a component (D), which is a resin different from the resin of the component (A), and which is a fluorine-containing resin having at least 1 kind selected from the group consisting of repeating units represented by the following formulae (D-1), (D-2) and (D-3);
in the formula, RAEach independently is a hydrogen atom or a methyl group; r51And R52Each independently represents a hydrogen atom, or a linear, branched or cyclic 1-valent hydrocarbon group having 1 to 10 carbon atoms; r53A single bond, or a straight or branched 2-valent hydrocarbon group having 1 to 5 carbon atoms; r54、R55And R56Independently represents a hydrogen atom, or a linear, branched or cyclic 1-valent hydrocarbon group having 1 to 15 carbon atoms, a fluorinated 1-valent hydrocarbon group, an acyl group or an acid-labile group; r54、R55And R56In the case of 1-valent hydrocarbon group or fluorinated 1-valent hydrocarbon group, a part of carbon atoms thereof may be substituted with ether groups or carbonyl groups; r57A (v +1) -valent hydrocarbon group or fluorinated hydrocarbon group having 1 to 20 carbon atoms, which is straight-chain, branched or cyclic; v is an integer of 1 to 3.
8. A pattern forming method, characterized by comprising the steps of:
applying the resist composition according to any one of claims 1 to 7 onto a substrate and performing heat treatment to form a resist film,
exposing the resist film to high-energy rays, and
the exposed resist film is developed using a developer.
9. The pattern forming method according to claim 8, wherein the high-energy radiation is ArF excimer laser having a wavelength of 193nm or KrF excimer laser having a wavelength of 248 nm.
10. The pattern forming method according to claim 8 or 9, wherein the exposure is immersion exposure performed by interposing a liquid having a refractive index of 1.0 or more between the resist film and the projection lens.
11. The method of claim 10, further comprising forming a protective film over the resist film, and performing immersion exposure by inserting the liquid between the protective film and a projection lens.
12. The method of claim 8, wherein the high-energy radiation is an electron beam or extreme ultraviolet radiation having a wavelength of 3 to 15 nm.
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| JP6673105B2 (en) * | 2016-08-31 | 2020-03-25 | 信越化学工業株式会社 | Sulfonium compound, resist composition and pattern forming method |
| JP7044011B2 (en) * | 2017-09-13 | 2022-03-30 | 信越化学工業株式会社 | Polymerizable monomers, polymers, resist materials, and pattern forming methods |
| JP7010260B2 (en) * | 2018-04-18 | 2022-01-26 | 信越化学工業株式会社 | Photoacid generator, chemically amplified resist material and pattern forming method |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008111103A (en) * | 2006-10-04 | 2008-05-15 | Shin Etsu Chem Co Ltd | Polymer compound, resist material, and pattern-forming method |
| US20080241736A1 (en) * | 2007-03-29 | 2008-10-02 | Tomohiro Kobayashi | Resist composition and patterning process |
| US20160259242A1 (en) * | 2014-08-21 | 2016-09-08 | Shin-Etsu Chemical Co., Ltd. | Novel onium salt compound, resist composition, and pattern forming process |
| US20180004087A1 (en) * | 2016-06-29 | 2018-01-04 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
| US20180024435A1 (en) * | 2016-07-22 | 2018-01-25 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process using the same |
| CN107870519A (en) * | 2016-09-27 | 2018-04-03 | 信越化学工业株式会社 | Sulfonium salt, anti-corrosion agent composition and patterning method |
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| JP2023075122A (en) | 2023-05-30 |
| KR20210055629A (en) | 2021-05-17 |
| JP2021076663A (en) | 2021-05-20 |
| JP7411838B2 (en) | 2024-01-11 |
| JP7256730B2 (en) | 2023-04-12 |
| KR102506110B1 (en) | 2023-03-03 |
| TW202122380A (en) | 2021-06-16 |
| TWI749848B (en) | 2021-12-11 |
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