JP5267126B2 - 感放射線性組成物及びそれに用いられる低分子量化合物の製造方法 - Google Patents
感放射線性組成物及びそれに用いられる低分子量化合物の製造方法 Download PDFInfo
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- JP5267126B2 JP5267126B2 JP2008533111A JP2008533111A JP5267126B2 JP 5267126 B2 JP5267126 B2 JP 5267126B2 JP 2008533111 A JP2008533111 A JP 2008533111A JP 2008533111 A JP2008533111 A JP 2008533111A JP 5267126 B2 JP5267126 B2 JP 5267126B2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
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- DBAVIPITSXUODT-UHFFFAOYSA-N bis[4-(trifluoromethyl)phenyl]iodanium Chemical compound C1=CC(C(F)(F)F)=CC=C1[I+]C1=CC=C(C(F)(F)F)C=C1 DBAVIPITSXUODT-UHFFFAOYSA-N 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
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- ZMJZYXKPJWGDGR-UHFFFAOYSA-N aminosulfamic acid Chemical class NNS(O)(=O)=O ZMJZYXKPJWGDGR-UHFFFAOYSA-N 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- QRMFGEKERJAYSQ-UHFFFAOYSA-N bis(4-chlorophenyl)iodanium Chemical compound C1=CC(Cl)=CC=C1[I+]C1=CC=C(Cl)C=C1 QRMFGEKERJAYSQ-UHFFFAOYSA-N 0.000 description 2
- BMOAHCCGSGYJFA-UHFFFAOYSA-M bis[4-(trifluoromethyl)phenyl]iodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC(C(F)(F)F)=CC=C1[I+]C1=CC=C(C(F)(F)F)C=C1 BMOAHCCGSGYJFA-UHFFFAOYSA-M 0.000 description 2
- IPNMEMKDCWTRGK-UHFFFAOYSA-M bis[4-(trifluoromethyl)phenyl]iodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C(F)(F)F)=CC=C1[I+]C1=CC=C(C(F)(F)F)C=C1 IPNMEMKDCWTRGK-UHFFFAOYSA-M 0.000 description 2
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
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- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
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- 125000004344 phenylpropyl group Chemical group 0.000 description 1
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- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- CENQGEGPYPBQSG-UHFFFAOYSA-N propane-1-sulfonohydrazide Chemical compound CCCS(=O)(=O)NN CENQGEGPYPBQSG-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005651 substituted 1,4-phenylene group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000002128 sulfonyl halide group Chemical group 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- BFFLLBPMZCIGRM-MRVPVSSYSA-N tert-butyl (2r)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1CO BFFLLBPMZCIGRM-MRVPVSSYSA-N 0.000 description 1
- BFFLLBPMZCIGRM-QMMMGPOBSA-N tert-butyl (2s)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1CO BFFLLBPMZCIGRM-QMMMGPOBSA-N 0.000 description 1
- NZNVBGIQMWGYRR-UHFFFAOYSA-N tert-butyl 2-phenylbenzimidazole-1-carboxylate Chemical compound N=1C2=CC=CC=C2N(C(=O)OC(C)(C)C)C=1C1=CC=CC=C1 NZNVBGIQMWGYRR-UHFFFAOYSA-N 0.000 description 1
- CROWJIMGVQLMPG-UHFFFAOYSA-N tert-butyl benzimidazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=NC2=C1 CROWJIMGVQLMPG-UHFFFAOYSA-N 0.000 description 1
- MTBKGWHHOBJMHJ-UHFFFAOYSA-N tert-butyl imidazole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CN=C1 MTBKGWHHOBJMHJ-UHFFFAOYSA-N 0.000 description 1
- KMUNFRBJXIEULW-UHFFFAOYSA-N tert-butyl n,n-bis(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)N(CCO)CCO KMUNFRBJXIEULW-UHFFFAOYSA-N 0.000 description 1
- WIURVMHVEPTKHB-UHFFFAOYSA-N tert-butyl n,n-dicyclohexylcarbamate Chemical compound C1CCCCC1N(C(=O)OC(C)(C)C)C1CCCCC1 WIURVMHVEPTKHB-UHFFFAOYSA-N 0.000 description 1
- UQEXYHWLLMPVRB-UHFFFAOYSA-N tert-butyl n,n-dioctylcarbamate Chemical compound CCCCCCCCN(C(=O)OC(C)(C)C)CCCCCCCC UQEXYHWLLMPVRB-UHFFFAOYSA-N 0.000 description 1
- QJONCGVUGJUWJQ-UHFFFAOYSA-N tert-butyl n,n-diphenylcarbamate Chemical compound C=1C=CC=CC=1N(C(=O)OC(C)(C)C)C1=CC=CC=C1 QJONCGVUGJUWJQ-UHFFFAOYSA-N 0.000 description 1
- VKUZRUNYENZANE-UHFFFAOYSA-N tert-butyl n-(1-adamantyl)-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound C1C(C2)CC3CC2CC1(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C3 VKUZRUNYENZANE-UHFFFAOYSA-N 0.000 description 1
- WFLZPBIWJSIELX-UHFFFAOYSA-N tert-butyl n-[10-[(2-methylpropan-2-yl)oxycarbonylamino]decyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCCNC(=O)OC(C)(C)C WFLZPBIWJSIELX-UHFFFAOYSA-N 0.000 description 1
- HXINNZFJKZMJJJ-UHFFFAOYSA-N tert-butyl n-[12-[(2-methylpropan-2-yl)oxycarbonylamino]dodecyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCCCCNC(=O)OC(C)(C)C HXINNZFJKZMJJJ-UHFFFAOYSA-N 0.000 description 1
- NMEQKHOJGXGOIL-UHFFFAOYSA-N tert-butyl n-[7-[(2-methylpropan-2-yl)oxycarbonylamino]heptyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCNC(=O)OC(C)(C)C NMEQKHOJGXGOIL-UHFFFAOYSA-N 0.000 description 1
- YLKUQZHLQVRJEV-UHFFFAOYSA-N tert-butyl n-[8-[(2-methylpropan-2-yl)oxycarbonylamino]octyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCNC(=O)OC(C)(C)C YLKUQZHLQVRJEV-UHFFFAOYSA-N 0.000 description 1
- XSIWKTQGPJNJBV-UHFFFAOYSA-N tert-butyl n-[9-[(2-methylpropan-2-yl)oxycarbonylamino]nonyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCNC(=O)OC(C)(C)C XSIWKTQGPJNJBV-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- IZBIRHQNPWSIET-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-fluorophenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(F)=CC=C1[S+](C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 IZBIRHQNPWSIET-UHFFFAOYSA-M 0.000 description 1
- PNHHQYMSCWPFFW-UHFFFAOYSA-N trifluoromethanesulfonohydrazide Chemical compound NNS(=O)(=O)C(F)(F)F PNHHQYMSCWPFFW-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- MAOCPIDAEMTJLK-UHFFFAOYSA-N tris(4-fluorophenyl)sulfanium Chemical compound C1=CC(F)=CC=C1[S+](C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 MAOCPIDAEMTJLK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/12—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing esterified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- 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
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Description
本発明の感放射線性組成物の一実施形態は、(A)酸の作用により分解してアルカリ現像液への溶解性を促進させる酸解離性基、及び活性光線又は放射線の照射により酸を発生する感放射線性酸発生基を、一分子中にそれぞれ一以上有する、ゲルパーミエーションクロマトグラフィ(GPC)によるポリスチレン換算数平均分子量(Mn)が500〜4000である低分子量化合物と、(B)溶剤とを含有するものである。以下、その詳細について説明する。
本発明の感放射線性組成物に含有される(A)低分子量化合物は、酸の作用により分解する酸解離性基を、一分子中に一以上有するものである。この酸解離性基は酸で解離(分解)することによって、この低分子量化合物を用いた感放射線性組成物のアルカリ現像液に対する溶解性を促進させる作用を示す。なお、この酸解離性基の具体例については後述する。
本発明の感放射線性組成物に含有される(A)低分子量化合物は、以下に示す(1)の方法に従って製造されるものである。
本発明の感放射線性組成物に含有される(B)溶剤の具体例としては、エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノ−n−プロピルエーテルアセテート、エチレングリコールモノ−n−ブチルエーテルアセテート等のエチレングリコールモノアルキルエーテルアセテート類;プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノ−n−プロピルエーテル、プロピレングリコールモノ−n−ブチルエーテル等のプロピレングリコールモノアルキルエーテル類;プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、プロピレングリコールジ−n−プロピルエーテル、プロピレングリコールジ−n−ブチルエーテル等のプロピレングリコールジアルキルエーテル類;プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノ−n−プロピルエーテルアセテート、プロピレングリコールモノ−n−ブチルエーテルアセテート等のプロピレングリコールモノアルキルエーテルアセテート類;乳酸メチル、乳酸エチル、乳酸n−プロピル、乳酸i−プロピル等の乳酸エステル類;ぎ酸n−アミル、ぎ酸i−アミル、酢酸エチル、酢酸n−プロピル、酢酸i−プロピル、酢酸n−ブチル、酢酸i−ブチル、酢酸n−アミル、酢酸i−アミル、プロピオン酸i−プロピル、プロピオン酸n−ブチル、プロピオン酸i−ブチル等の脂肪族カルボン酸エステル類;ヒドロキシ酢酸エチル、2−ヒドロキシ−2−メチルプロピオン酸エチル、2−ヒドロキシ−3−メチル酪酸メチル、メトキシ酢酸エチル、エトキシ酢酸エチル、3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−エトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、3−メトキシブチルアセテート、3−メチル−3−メトキシブチルアセテート、3−メチル−3−メトキシブチルプロピオネート、3−メチル−3−メトキシブチルブチレート、アセト酢酸メチル、アセト酢酸エチル、ピルビン酸メチル、ピルビン酸エチル等の他のエステル類;トルエン、キシレン等の芳香族炭化水素類;メチルエチルケトン、メチルプロピルケトン、メチルブチルケトン、2−ヘプタノン、3−ヘプタノン、4−ヘプタノン、シクロヘキサノン等のケトン類;N−メチルホルムアミド、N,N−ジメチルホルムアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルピロリドン等のアミド類;γ−ブチロラクン等のラクトン類等を挙げることができる。これらの(B)溶剤は、一種単独で又は二種以上を組み合わせて用いることができる。
本発明の感放射線性組成物に含有される、(A)低分子量化合物の割合は、感放射線性組成物に含有される固形分全体を100質量%とした場合に、80質量%以上であり、90質量%以上であることが更に好ましい。(A)低分子量化合物の含有割合が80質量%未満であると、本発明の効果が十分に得られず、ラインエッジラフネスが劣化する。なお、(A)低分子量化合物の含有割合の上限値については特に限定されないが、100質量%以下であればよい。
本発明の感放射線性組成物には、必要に応じて、(A)低分子量化合物及び(B)溶剤以外のその他の成分を配合することができる。配合することのできる「その他の成分」としては、感放射線性酸発生剤、アルカリ溶解制御剤、酸拡散制御剤、酸解離性アルカリ可溶性樹脂、界面活性剤、増感剤等を挙げることができる。
アルカリ溶解制御剤としては、例えば、フェノール性水酸基、カルボキシル基等の酸性官能基の水素原子を、酸解離性基やt−ブトキシカルボニルメチル基で置換した化合物等を挙げることができる。前記酸解離性基としては、例えば、置換メチル基、1−置換エチル基、1−置換−n−プロピル基、1−分岐アルキル基、シリル基、ゲルミル基、アルコキシカルボニル基、アシル基、環式酸解離性基等を挙げることができる。
本発明の感放射線性組成物には、EB、X線、又はEUV照射により生じた酸のレジスト被膜中における拡散現象を制御し、非照射領域での好ましくない化学反応を抑制する作用を有する酸拡散制御剤を配合することが好ましい。このような酸拡散制御剤を配合することにより、感放射線性組成物の貯蔵安定性が向上する。また、レジストとして解像度が向上するとともに、照射から照射後の加熱処理までの引き置き時間(PED)の変動によるレジストパターンの線幅変化を抑えることができ、プロセス安定性を極めて良好にすることができる。
界面活性剤を配合すると、感放射線性組成物の塗布性やストリエーション、レジストとしての現像性等を改良することができるために好ましい。界面活性剤としては、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンn−オクチルフェノールエーテル、ポリオキシエチレンn−ノニルフェノールエーテル、ポリエチレングリコールジラウレート、ポリエチレングリコールジステアレート等を挙げることができる。
好ましい増感剤としては、例えば、カルバゾール類、ベンゾフェノン類、ローズベンガル類、アントラセン類等を挙げることができる。これらの増感剤は、一種単独で又は二種以上を組み合わせて用いることができる。なお、増感剤の配合量は、(A)低分子量化合物100質量部に対して、10質量部以下とすることが好ましい。
本発明の感放射線性組成物は、例えば、(A)低分子量化合物及び(B)溶剤、並びに必要に応じて配合されるその他の成分を、定法に従って混合・溶解することにより調製することができる。調製に際しては、得られる感放射線性組成物の全固形分濃度が、通常、0.1〜50質量%、好ましくは1〜30質量%となるようにそれぞれの成分を配合する。なお、固形分を(B)溶剤に溶解させた後は、例えば、孔径200nm程度のフィルタ等でろ過することが好ましい。
次に、本発明の感放射線性組成物を用いたレジストパターンの形成方法にいて説明する。先ず、前述のように調製された感放射線性組成物を基板上に塗布してレジスト被膜を形成する。基板としては、例えば、シリコンウェハ、アルミニウムで被覆されたウェハ等を用いることができる。また、感放射線性組成物を基板上に塗布する手段としては、例えば、回転塗布、流延塗布、ロール塗布等の塗布手段を挙げることができる。なお、レジスト被膜の形成に際しては、場合により、予め70℃〜160℃程度の温度で加熱処理(PB)を行なってもよい。
1,3,5−トリス(4−ヒドロキシフェニル)ベンゼン18gをテトラヒドロフラン500mlに溶解した。カリウム−t−ブトキシド6gを加え、室温で5分撹拌した。ブロモ酢酸−t−ブチル10gを滴下した後、60℃に加熱しながら6時間撹拌した。テトラヒドロフランを減圧留去した後、ジクロロメタン300mlで抽出し、シリカゲルカラムで精製した。乾燥後、1−(t−ブトキシカルボニルメトキシフェニル)−3,5−ジ(4−ヒドロキシフェニル)ベンゼンを4.6g得た。
1,3,5−トリス(4−ヒドロキシフェニル)ベンゼンを、下記化合物(a−4)に変更したこと以外は、前述の「実施例1」と同様の操作により、下記化合物(A−2)(実施例2)を0.1g得た。
化合物(a−1)4g、及び1,1,2,2−テトラフルオロ−5−ヒドロキシペンタン−1−スルホン酸トリフェニルスルホニウム5gを塩化メチレン100mlに溶解させた後、N,N’−ジシクロヘキシルカルボジイミド20gを加え、24時間室温にて撹拌した。水100mlを加えた後、得られた沈殿物をろ過により除去し、ろ液を塩化メチレン100mlにより抽出した。シリカゲルカラムで精製し、乾燥することにより、下記化合物(a−5)を1.1g得た。
1,3,5−トリス(4−ヒドロキシフェニル)ベンゼン3.5gをテトラヒドロフラン200mlに溶解させ、更に、トリエチルアミン1.0g、4−ジメチルアミノピリジン1.2g加えて撹拌した。そこに、テトラヒドロフラン20mlに溶解させたジ−t−ブチル−ジ−カーボネート2.2gをゆっくり滴下し、室温で6時間撹拌した。テトラヒドロフランを減圧留去した後、ジクロロメタン200mlで抽出した。シリカゲルカラムで精製することにより、下記化合物(A−4)(比較例1)を0.7g得た。
化合物(a−4)3.8gをテトラヒドロフラン200mlに溶解させ、更に、トリエチルアミン1.0g、4−ジメチルアミノピリジン1.2g加えて撹拌した。そこに、テトラヒドロフラン20mlに溶解させたジ−t−ブチル−ジ−カーボネート2.2gをゆっくり滴下し、室温で6時間撹拌した。テトラヒドロフランを減圧留去した後、ジクロロメタン200mlで抽出した。シリカゲルカラムで精製することにより、下記化合物(A−5)(比較例2)を0.2g得た。
化合物(A−1)100部、溶剤(B−1)1200部、溶剤(B−2)600部、及び酸拡散制御剤(D−1)0.3部を混合して均一溶液とした後、孔径200nmのメンブランフィルタでろ過することにより、感放射線性組成物(実施例4)を調製した。
表1に示す配合処方としたこと以外は、実施例4の場合と同様にして、感放射線性組成物(実施例5〜7、比較例3、4)を調製した。なお、使用した各成分(表1)の詳細を以下に示す。
(B−1):乳酸エチル
(B−2):プロピレングリコールモノメチルエーテルアセテート
(C−1):トリフェニルスルホニウムトリフルオロメタンスルホネート
(D−1):トリ−n−オクチルアミン
実施例4〜7、及び比較例3、4の感放射線性組成物について、以下に示す各種評価を行った。評価結果を表2に示す。また。評価方法は以下に示すとおりである。
Claims (3)
- (A)酸の作用により分解してアルカリ現像液への溶解性を促進させる酸解離性基、及び活性光線又は放射線の照射により酸を発生する感放射線性酸発生基を、一分子中にそれぞれ一以上有する、ゲルパーミエーションクロマトグラフィ(GPC)によるポリスチレン換算数平均分子量(Mn)が500〜4000である低分子量化合物と、
(B)溶剤と、
を含有し、
前記(A)低分子量化合物が、
フェノール性水酸基及びカルボキシル基の少なくとも一種を有する化合物を、
酸、塩基、及び脱水剤からなる群より選択される少なくとも一種の存在下、エーテル化又はエステル化反応によりオニウム塩と縮合させることで得られる下記一般式(1)で表されるものであり、且つ、不飽和結合を持った単量体を、開始剤を使用しつつその不飽和結合を開裂させ、連鎖的に結合を成長させることによって得られる重合体ではなく、
前記(A)低分子量化合物の含有割合が、全固形分100質量%に対して80質量%以上である感放射線性組成物。
- 酸拡散制御剤を更に含有する請求項1に記載の感放射線性組成物。
- フェノール性水酸基及びカルボキシル基の少なくとも一種を有する化合物を、酸、塩基、及び脱水剤からなる群より選択される少なくとも一種の存在下、エーテル化又はエステル化反応によりオニウム塩と縮合させることにより、
酸の作用により分解してアルカリ現像液への溶解性を促進させる酸解離性基、及び活性光線又は放射線の照射により酸を発生する感放射線性酸発生基、を一分子中にそれぞれ一以上有する、ゲルパーミエーションクロマトグラフィ(GPC)によるポリスチレン換算数平均分子量(Mn)が500〜4000であり、請求項1または2に記載の感放射線性樹脂組成物に含有される前記(A)低分子量化合物を得る低分子量化合物の製造方法。
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- 2007-08-28 EP EP07793084A patent/EP2060949A4/en not_active Withdrawn
- 2007-08-28 KR KR1020097006698A patent/KR101442860B1/ko active IP Right Grant
- 2007-08-28 WO PCT/JP2007/066644 patent/WO2008029673A1/ja active Application Filing
- 2007-08-28 JP JP2008533111A patent/JP5267126B2/ja active Active
- 2007-08-28 US US12/439,860 patent/US8361691B2/en active Active
- 2007-09-04 TW TW096132895A patent/TW200815923A/zh unknown
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2012
- 2012-12-19 US US13/719,264 patent/US8771923B2/en active Active
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2013
- 2013-02-18 JP JP2013029533A patent/JP2013145384A/ja active Pending
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Also Published As
Publication number | Publication date |
---|---|
JP2013145384A (ja) | 2013-07-25 |
TW200815923A (en) | 2008-04-01 |
KR101442860B1 (ko) | 2014-09-22 |
JPWO2008029673A1 (ja) | 2010-01-21 |
US20130108962A1 (en) | 2013-05-02 |
EP2060949A1 (en) | 2009-05-20 |
US8361691B2 (en) | 2013-01-29 |
WO2008029673A1 (fr) | 2008-03-13 |
KR20090064413A (ko) | 2009-06-18 |
US8771923B2 (en) | 2014-07-08 |
US20090280433A1 (en) | 2009-11-12 |
EP2060949A4 (en) | 2011-05-04 |
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