JP6176426B2 - 含フッ素化合物、リビング重合開始剤、含フッ素重合体、含フッ素重合体の製造方法及びレジスト組成物 - Google Patents
含フッ素化合物、リビング重合開始剤、含フッ素重合体、含フッ素重合体の製造方法及びレジスト組成物 Download PDFInfo
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- JP6176426B2 JP6176426B2 JP2017516187A JP2017516187A JP6176426B2 JP 6176426 B2 JP6176426 B2 JP 6176426B2 JP 2017516187 A JP2017516187 A JP 2017516187A JP 2017516187 A JP2017516187 A JP 2017516187A JP 6176426 B2 JP6176426 B2 JP 6176426B2
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- 150000001875 compounds Chemical class 0.000 title claims description 157
- 239000000203 mixture Substances 0.000 title claims description 113
- 229910052731 fluorine Inorganic materials 0.000 title claims description 104
- 239000011737 fluorine Substances 0.000 title claims description 79
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 78
- 229920000642 polymer Polymers 0.000 title claims description 70
- 239000003505 polymerization initiator Substances 0.000 title description 15
- 238000004519 manufacturing process Methods 0.000 title description 14
- 238000010550 living polymerization reaction Methods 0.000 title description 2
- -1 1-bromopropyl group Chemical group 0.000 claims description 331
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- 239000011347 resin Substances 0.000 claims description 244
- 239000002253 acid Substances 0.000 claims description 162
- 125000004432 carbon atom Chemical group C* 0.000 claims description 139
- 239000000178 monomer Substances 0.000 claims description 124
- 125000000217 alkyl group Chemical group 0.000 claims description 120
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 75
- 229920002313 fluoropolymer Polymers 0.000 claims description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 239000004811 fluoropolymer Substances 0.000 claims description 64
- 230000009471 action Effects 0.000 claims description 52
- 238000010526 radical polymerization reaction Methods 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 230000002829 reductive effect Effects 0.000 claims description 20
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
- 125000001033 ether group Chemical group 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
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- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 271
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 81
- 238000000576 coating method Methods 0.000 description 70
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- 238000000034 method Methods 0.000 description 64
- 125000000753 cycloalkyl group Chemical group 0.000 description 62
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 54
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- 125000001424 substituent group Chemical group 0.000 description 42
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 39
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 31
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- 229910052757 nitrogen Inorganic materials 0.000 description 27
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 26
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- 125000004093 cyano group Chemical group *C#N 0.000 description 24
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 22
- 239000000758 substrate Substances 0.000 description 22
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- PHCKFVVLVZFFLU-UHFFFAOYSA-N dodec-4-ene Chemical compound CCCCCCCC=CCCC PHCKFVVLVZFFLU-UHFFFAOYSA-N 0.000 description 20
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- SJLFPIVMVNNGAR-UHFFFAOYSA-N 2-propyldec-6-enoic acid Chemical compound CCCC=CCCCC(CCC)C(=O)O SJLFPIVMVNNGAR-UHFFFAOYSA-N 0.000 description 19
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000000962 organic group Chemical group 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
- 229910052801 chlorine Inorganic materials 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 17
- 239000000463 material Substances 0.000 description 17
- 238000005406 washing Methods 0.000 description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 16
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 16
- 239000012860 organic pigment Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000004593 Epoxy Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 15
- 125000001309 chloro group Chemical group Cl* 0.000 description 15
- 238000005259 measurement Methods 0.000 description 15
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 14
- 239000011342 resin composition Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000002202 Polyethylene glycol Substances 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 13
- 238000011161 development Methods 0.000 description 13
- 125000005647 linker group Chemical group 0.000 description 13
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 12
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 12
- 238000001459 lithography Methods 0.000 description 12
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 12
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- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 11
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/18—Esters containing halogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
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- 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
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Description
で表されることを特徴とする含フッ素化合物を提供するものである。
で表されることを特徴とする。
で表されるアルコール化合物(α)と、下記(β−1)〜(β−4)等の化合物(β)とを反応(エステル化反応)させることにより得られる。
2)2級炭素原子または3級炭素原子を有し、該2級炭素原子または3級炭素原子に直接結合した臭素原子または塩素原子を有する酸無水物(β−2)。
3)2級炭素原子または3級炭素原子を有し、該2級炭素原子または3級炭素原子に直接結合した臭素原子または塩素原子を有する酸アルキルエステル化物(β−3)。
4)2級炭素原子または3級炭素原子を有し、該2級炭素原子または3級炭素原子に直接結合した臭素原子または塩素原子を有するカルボン酸化合物(β−4)。
ポリプロピレングリコールモノ(メタ)アクリレート、ポリエチレングリコールモノ(メタ)アクリレート、ポリテトラメチレングリコール(メタ)アクリレート、ポリ(エチレングリコール・プロピレングリコール)モノ(メタ)アクリレート、ポリエチレングリコール・ポリプロピレングリコールモノ(メタ)アクリレート、ポリ(エチレングリコール・テトラメチレングリコール)モノ(メタ)アクリレート、ポリエチレングリコール・ポリテトラメチレングリコールモノ(メタ)アクリレート、ポリ(プロピレングリコール・テトラメチレングリコール)モノ(メタ)アクリレート、ポリプロピレングリコール・ポリテトラメチレングリコールモノ(メタ)アクリレート、ポリ(プロピレングリコール・ブチレングリコール)モノ(メタ)アクリレート、ポリプロピレングリコール・ポリブチレングリコールモノ(メタ)アクリレート、ポリ(エチレングリコール・ブチレングリコール)モノ(メタ)アクリレート、ポリエチレングリコール・ポリブチレングリコールモノ(メタ)アクリレート、ポリ(テトラエチレングリコール・ブチレングリコール)モノ(メタ)アクリレート、ポリテトラエチレングリコール・ポリブチレングリコールモノ(メタ)アクリレート、ポリブチレングリコールモノ(メタ)アクリレート、ポリ(エチレングリコール・トリメチレングリコール)モノ(メタ)アクリレート、ポリエチレングリコール・ポリトリメチレングリコールモノ(メタ)アクリレート、ポリ(プロピレングリコール・トリメチレングリコール)モノ(メタ)アクリレート、ポリプロピレングリコール・ポリトリメチレングリコールモノ(メタ)アクリレート、ポリ(トリメチレングリコール・テトラメチレングリコール)モノ(メタ)アクリレート、ポリトリメチレングリコール・ポリテトラメチレングリコールモノ(メタ)アクリレート、ポリ(ブチレングリコール・トリメチレングリコール)モノ(メタ)アクリレート、ポリブチレングリコール・ポリトリメチレングリコールモノ(メタ)アクリレート等が挙げられる。
測定装置:東ソー株式会社製「HLC−8220 GPC」
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテックジャパン株式会社製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
・酸性基を有する(メタ)アクリル系重合性単量体を必須の成分として重合させて得られるアルカリ可溶性樹脂(C1)
・反応性基を持つ(メタ)アクリル系重合性単量体を必須の成分として重合させて得られる酸性基を有さない重合体と、該反応性基に対して反応性を有する反応性基と酸基とを有する化合物とを反応させて得られるアルカリ可溶性樹脂(C2)
・エポキシ基含有(メタ)アクリレートと、他の重合性単量体との共重合体に対し、該共重合体が有するエポキシ基の少なくとも一部に不飽和モノカルボン酸を付加させ、さらに不飽和モノカルボン酸の付加反応により生じた水酸基の少なくとも一部にポリカルボン酸の酸無水物を付加反応させて得られるアルカリ可溶性樹脂(C3)
・カルボキシル基と重合性不飽和基を有するエポキシ(メタ)アクリレート樹脂(C4)
・カルボキシル基と重合性不飽和基を有するカルド型樹脂(C5)
以下に、上記(C1)〜(C5)について詳細に説明する。
・2−ヒドロキシエチル(メタ)アクリレートのような水酸基を有する重合性単量体を必須の成分として重合体を得た後、コハク酸無水物、テトラヒドロフタル酸無水物、マレイン酸無水物等の酸無水物を付加させて得られるアルカリ可溶性樹脂。
R5は、−OH、−SO3−、−SO3H、−SO3 −M+、−CO2H、−CO2 −M+、−CO2R8、−SO3R8又は−SO2NR9R10であり、mは0〜5の整数を表し(但し、mが2以上の整数である場合、複数のR5は同一であっても、異なっていてもよい。)、
R6及びR7は、それぞれ独立に、炭素数1〜6のアルキル基である。
Xは、ハロゲン原子であり、a1は、0又は1の整数であり、
R25は、−SO3−、−SO3 −Ma+、−SO3H又はSO2NHR26であり、m1は、0〜5の整数(但し、m1が2以上の整数である場合、複数のR25は同一であっても異なっていてもよい)である。
)
で表される繰り返し単位等を挙げることができる。
で表される繰り返し単位等を挙げることができる。
で表される繰り返し単位等を挙げることができる。
フルオロイソプロパノール基)、スルホン酸基が挙げられる。
られる。
ル基、n−ブチル基、イソブチル基、t−ブチル基などの炭素原子数1〜4のものが好ましい。
カニル基、アダマンチル基などの多環のシクロアルキル基が好ましい。
合して上述のシクロアルキル基を形成している態様が挙げられる。
ル基、エチル基がより好ましく、メチル基が特に好ましい。R2としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基が好ましく、メチル基、エチル基がより好ましく、メチル基が特に好ましい。R3としては、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、tert−ブチル基が好ましく、メチル基、エチル基、イソプロピル基、イソブチル基がより好ましく、メチル基、エチル基、イソプロピル基が特に好ましい。
炭素原子数1〜4のアルキル基、炭素原子数3〜8のシクロアルキル基、ハロゲン原子、炭素原子数1〜4のアルコキシ基、カルボキシル基、炭素原子数2〜6のアルコキシカルボニル基などが挙げられ、炭素原子数8以下が好ましい。なかでも、酸分解前後での有機溶剤を含有する現像液に対する溶解コントラストをより向上させる観点から、酸素原子、窒素原子、硫黄原子などのヘテロ原子を有さない置換基であることがより好ましく水素原子及び炭素原子のみからなる基であることが更に好ましく、直鎖アルキル基、分岐アルキル基、シクロアルキル基であることが特に好ましい。
ビシクロオクタン環基、トリシクロ[5、2、1、02,6]デカン環基などが挙げられる。より好ましい架橋環式炭化水素環基としてノルボナン環基、アダマンタン環基が挙げられる。
シ基、−COR、−COOR、−CON(R)2、−SO2R、−SO3R、
−SO2N(R)2は、更に置換基を有していてもよく、そのような置換基としては、ハロゲン原子(好ましくは、フッ素原子)が挙げられる。
置換されたアルキル基におけるアルキル基部分の炭素原子数は、1〜25であることが好ましい。1つ以上のシリル基により置換されたアルキル基におけるアルキル基部分の炭素原子数は、1〜30であることが好ましい。また、R4のシクロアルキル基が置換基を有していない場合、その炭素原子数は、3〜20であることが好ましい。
好ましい置換基(Rb2)としては、炭素原子数1〜8のアルキル基、炭素原子数4〜7のシクロアルキル基、炭素原子数1〜8のアルコキシ基、炭素原子数2〜8のアルコキシカルボニル基、カルボキシル基、ハロゲン原子、水酸基、シアノ基、酸分解性基などが挙げられる。より好ましくは炭素原子数1〜4のアルキル基、シアノ基、酸分解性基である。n2は、0〜4の整数を表す。n2が2以上の時、複数存在する置換基(Rb2)は、同一でも異なっていてもよい。また、複数存在する置換基(Rb2)同士が結合して環を形成してもよい。
し単位が好ましい。
せて用いてもよい。
記一般式(VI)で表される繰り返し単位とは異なることが好ましい。
R1cは、水素原子、メチル基、トリフロロメチル基又はヒドロキシメチル基を表す。R2c〜R4cは、一般式(VIIa)〜(VIIc)に於ける、R2c〜R4cと同義である。
を以下に挙げる。式中、Raは、H、CH3、CH2OH又はCF3を表す。
装置:株式会社島津製作所製「FTIR−8400S」
測定方法:KBr法
装置:日本電子株式会社製「JNM−AL400」
溶媒:クロロホルム−d6
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテックジャパン株式会社製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、下記構造式(X−1)で表される両末端水酸基含有パーフルオロポリエーテル化合物(X−1)200g、溶媒としてジイソプロピルエーテル110g、中和剤としてトリエチルアミン29.1gを仕込み、窒素気流下にて攪拌を開始し、フラスコ内を5℃以下に保ちながら2−ブロモイソ酪酸ブロミド58.1gを30分かけて滴下した。滴下終了後、室温にて2時間攪拌した後、40℃に昇温して3時間攪拌することにより反応を行い、ガスクロマトグラフィー測定にて2−ブロモイソ酪酸ブロミドの消失を確認した。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、下記構造式(X−2)で表される片末端水酸基含有パーフルオロポリエーテル化合物(X−2)200g、溶媒としてジイソプロピルエーテル250g、中和剤としてトリエチルアミン24gを仕込み、窒素気流下にて攪拌を開始し、フラスコ内を5℃以下に保ちながら2−ブロモイソ酪酸ブロミド38gを30分かけて滴下した。滴下終了後、室温にて2時間攪拌した後、40℃に昇温して5時間攪拌することにより反応を行い、ガスクロマトグラフィー測定にて2−ブロモイソ酪酸ブロミドの消失を確認した。
窒素置換したフラスコに、溶剤としてメチルエチルケトン81.5gと、t−ブチルメタクリレート40.9gを仕込み、窒素気流下にて攪拌しながら50℃に昇温した。次いで、2,2’−ビピリジル1.7g、塩化第一銅0.7gを仕込み、フラスコ内を50℃に保ちながら30分撹拌した。その後、実施例1で合成した含フッ素化合物(1)3.3g加え、窒素気流下、50℃で21時間反応させ、反応物を得た。
・溶液の調製
含フッ素重合体(1)を20%含むプロピレングリコールモノメチルエーテルアセテート(PGMEA)溶液5部、酸発生剤(トリ−p−トリルスルホニウムトリフルオロメタンスルホナート)10部、クエンチャー(トリエチルアミン)1部及びArFレジスト樹脂溶液(2−メチル−2−アダマンチルメタクリレート/γ−ブチロラクトンメタクリレート/3−ヒドロキシ−1−アダマンチルメタクリレートの共重合物をPGMEAに10%の濃度で溶解させたもの)1000部を混合した溶液(ポジ型レジスト組成物)を調製した。
該溶液3mLを6インチのシリコンウェハの中央部分に滴下し、回転数3,000rpm、回転時間30秒でスピンコ−ティングした後、110℃で1分間加熱乾燥させて塗膜を作製した。
得られた塗膜を目視で観察し、下記基準に従って評価した。
○:3cm角の塗膜中に異物が一つも確認されない。
△:3cm角の塗膜中に異物が1〜10個確認される。
×:3cm角の塗膜中に異物が10個より多く確認される。
前記<塗膜中の異物の有無の評価>において得た塗膜の表面について、接触角測定装置(協和界面科学株式会社製「MODEL CA−W150」)を用いて、水の接触角を測定した。
・現像方法
前記<塗膜中の異物の有無の評価>において得た塗膜に対して、マスクパターンを用いずに、ArFエキシマーランプを照射した(中心波長193nm、照射量30mJ/cm2)。照射後、110℃で60秒間の加熱処理(PEB処理)を行い、さらに2.38%のテトラメチルアンモニウムヒドロキシド(TMAH)水溶液で60秒間現像処理を行った。その後30秒間、純水を用いて水リンスし、エアスプレーにて乾燥を行った。現像前後の膜厚測定から、残膜率を算出することで、現像性を評価した。残膜率が低い程、現像性に優れる塗膜である。
◎:残膜率が0%である(残膜なし)。
○:残膜率が0%を超えて10%以下である。
△:残膜率が10%を超えて50%以下である。
×:残膜率が50%を超える。
窒素置換したフラスコに、溶剤としてメチルエチルケトン81.5gと、2−メチル−2−アダマンチルメタクリレート40.9gを仕込み、窒素気流下にて攪拌しながら50℃に昇温した。次いで、2,2’−ビピリジル1.7g、塩化第一銅0.7gを仕込み、フラスコ内を50℃に保ちながら30分撹拌した。その後、実施例1で合成した含フッ素化合物(1)3.3g加え、窒素気流下、50℃で30時間反応させ、反応物を得た。
窒素置換したフラスコに、溶剤としてメチルエチルケトン81.5gと、1-イソブトキシエチルメタクリレート40.9gを仕込み、窒素気流下にて攪拌しながら50℃に昇温した。次いで、2,2’−ビピリジル1.7g、塩化第一銅0.7gを仕込み、フラスコ内を50℃に保ちながら30分撹拌した。その後、実施例1で合成した含フッ素化合物(1)3.3g加え、窒素気流下、50℃で24時間反応させ、反応物を得た。
窒素置換したフラスコに、溶剤としてメチルエチルケトン81.5gと、t−ブチルメタクリレート40.9gを仕込み、窒素気流下にて攪拌しながら50℃に昇温した。次いで、2,2’−ビピリジル1.7g、塩化第一銅0.7gを仕込み、フラスコ内を50℃に保ちながら30分撹拌した。その後、実施例2で合成した含フッ素化合物(2)3.3g加え、窒素気流下、50℃で21時間反応させ、反応物を得た。
窒素置換したフラスコに、溶剤としてメチルエチルケトン81.5gと、ポリプロピレンオキシメタクリレート(プロピレンオキシ基の繰り返し数5)40.9gを仕込み、窒素気流下にて攪拌しながら60℃に昇温した。次いで、2,2’−ビピリジル1.7g、塩化第一銅0.7gを仕込み、フラスコ内を60℃に保ちながら30分撹拌した。その後、実施例1で合成した含フッ素化合物(1)3.3g加え、窒素気流下、60℃で30時間反応させ、反応物を得た。
・溶液の調製
含フッ素重合体(5)を20%含むプロピレングリコールモノメチルエーテルアセテート(PGMEA)溶液5部、酸発生剤(トリ−p−トリルスルホニウムトリフルオロメタンスルホナート)10部、クエンチャー(トリエチルアミン)1部及び2−メチル−2−アダマンチルメタクリレート/γ−ブチロラクトンメタクリレート/3−ヒドロキシ−1−アダマンチルメタクリレートの共重合物(酸の作用により極性が増大し、その結果、有機溶剤に対する溶解性が減少する樹脂)をPGMEAに10%の濃度で溶解させた溶液1000部を混合した溶液(ネガ型レジスト組成物)を調製した。
実施例3と同様の方法にて塗膜を作製した。
得られた塗膜の膜厚を大塚電子株式会社製FE−3000を用いて塗膜中央部分を2mm間隔で200点測定し、その標準偏差を測定した。標準偏差の数値が大きい程、塗膜中の異物が少なくレベリング性に優れる。
FASTOGENグリーンA110(DIC株式会社製)10gをポリビンに入れ、PGMEA 60g、DISPERBYK LPN21116(ビックケミー株式会社製)12g、0.3−0.4mmΦセプルビーズを加え、ペイントコンディショナー(東洋精機株式会社製)で2時間分散し、緑色顔料分散液を得た。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、前記両末端水酸基含有パーフルオロポリエーテル化合物(X−1)20g、溶媒としてジイソプロピルエーテル10g、重合禁止剤としてp−メトキシフェノール0.006g及び中和剤としてトリエチルアミン3.3gを仕込み、空気気流下にて攪拌を開始し、フラスコ内を10℃に保ちながらメタクリル酸クロライド3.1gを2時間かけて滴下した。滴下終了後、10℃で1時間攪拌し、昇温して30℃で1時間攪拌した後、50℃に昇温して10時間攪拌することにより反応を行い、ガスクロマトグラフィー測定にてメタクリル酸クロライドの消失を確認した。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、溶媒としてメチルイソブチルケトン260gを仕込み、窒素気流下にて攪拌しながら105℃に昇温した。次いで、単量体(a´)20g、2−メチル−2−アダマンチルメタクリレート80gと溶媒としてメチルイソブチルケトン80gを混合した単量体溶液、ラジカル重合開始剤としてt−ブチルペルオキシ−2−エチルヘキサノエート15gと溶媒としてメチルイソブチルケトン60gを混合した開始剤溶液の3種類の滴下液をそれぞれ別々の滴下装置にセットし、フラスコ内を105℃に保ちながら同時に2時間かけて滴下した。滴下終了2時間後と4時間後に、t−ブチルペルオキシ−2−エチルヘキサノエートを各2gずつ追加した。その後、105℃で10時間攪拌して、比較対照用の含フッ素重合体(2´)の溶液を得た。反応終了後、減圧下で溶媒を留去し、PGMEAを加えて希釈することにより、含フッ素重合体(2´)を20%含有するPGMEA溶液を得た。含フッ素重合体(2´)は、数平均分子量が600、重量平均分子量が1,100であった。また、フッ素含有率は11%であった。含フッ素重合体(2´)を用いた以外は実施例3と同様にして塗膜を作製し、塗膜中の異物の有無を確認すると共に、撥液性と現像性の評価を行った。その評価方法を下記に示す。また、各評価の結果を第1表に示す。
比較例1で得た含フッ素重合体(1´)を用いた以外は実施例7と同様にして塗膜中の異物の有無(レベリング性)を確認すると共に、撥液性の評価を行った。評価結果を第2表に示す。
比較例2で得た含フッ素重合体(2´)を用いた以外は実施例7と同様にして塗膜中の異物の有無(レベリング性)を確認すると共に、撥液性の評価を行った。評価結果を第2表に示す。
比較例1で得た含フッ素重合体(1´)を用いた以外は実施例8と同様にして塗膜中の異物の有無(レベリング性)を確認すると共に、撥液性の評価を行った。評価結果を第3表に示す。
Claims (16)
- 下記一般式(1)
で表される含フッ素化合物由来の構造と、
ポリオキシアルキレン基を有するラジカル重合性不飽和単量体(A1)由来の構造又は
酸の作用により分解してアルカリ可溶性基を生じる基を有するラジカル重合性不飽和単量体(A2)由来の構造と、を有することを特徴とする含フッ素重合体。 - 前記ラジカル重合性不飽和単量体(A2)中の酸の作用により分解してアルカリ可溶性基を生じる基が、アルカリ可溶性基が有する水素原子をターシャリーブチル基、2−アルキル−2−アダマンチル基または1−アルコキシエチル基で保護したものである請求項1記載の含フッ素重合体。
- 前記X1が、1−ブロモ−1−メチルエチル基、1−ブロモ−1−メチルプロピル基、1−ブロモ−1−メチルブチル基、1−ブロモ−1,2−ジメチルプロピル基、1−クロロ−1−メチルエチル基、1−クロロ−1−メチルプロピル基、1−クロロ−1−メチルブチル基、又は1−クロロ−1,2−ジメチルプロピル基である請求項1〜2の何れか1項記載の含フッ素重合体。
- 前記X1がそれぞれ1−ブロモ−1−メチルエチル基である請求項1〜3の何れか1項記載の含フッ素重合体。
- 前記R1、R2がそれぞれメチレン基またはエチレン基である請求項1〜4の何れか1項記載の含フッ素重合体。
- 前記ラジカル重合性不飽和単量体(A1)中のポリオキシアルキレン基が炭素原子数2〜4のオキシアルキレン基を繰り返し単位とするものである請求項1,3〜6の何れか1項記載の含フッ素重合体。
- 下記一般式(1)
で表されることを特徴とするリビングラジカル重合開始剤。 - 請求項1〜8のいずれか1項記載の含フッ素重合体を含有することを特徴とするレジスト組成物。
- 請求項1〜8のいずれか1項に記載の含フッ素重合体と、アルカリ可溶性樹脂(C)と、アルカリ可溶性樹脂(C)以外の重合性化合物(D)と、着色剤(E)とを含む請求項10記載のレジスト組成物。
- 前記アルカリ可溶性樹脂(C)100質量部に対して請求項1〜8のいずれか1項に記載の含フッ素重合体を0.01〜10質量部含有する請求項11記載のレジスト組成物。
- 請求項1〜8のいずれか1項記載の含フッ素重合体と、酸の作用によりアルカリ性の溶液に対する溶解性が増大する樹脂(F)と、露光により酸を発生する酸発生成分(G)とを含む請求項10記載のレジスト組成物。
- 前記酸の作用によりアルカリ性の溶液に対する溶解性が増大する樹脂(F)100質量部に対して請求項1〜8のいずれか1項記載の含フッ素重合体を0.01〜10質量部含有する請求項13記載のレジスト組成物。
- 請求項1〜8のいずれか1項に記載の含フッ素重合体と、酸の作用により有機溶剤に対する溶解性が減少する樹脂(H)と、露光により酸を発生する酸発生成分(G)とを含む請求項10記載のレジスト組成物。
- 前記酸の作用により有機溶剤に対する溶解性が減少する樹脂(H)100質量部に対して請求項1〜8のいずれか1項に記載の含フッ素重合体を0.01〜10質量部含有する請求項15記載のレジスト組成物。
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