JP5833492B2 - ケイ素化合物、ポリシロキサン化合物、これを含むレジスト下層膜形成用組成物及びパターン形成方法 - Google Patents
ケイ素化合物、ポリシロキサン化合物、これを含むレジスト下層膜形成用組成物及びパターン形成方法 Download PDFInfo
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- JP5833492B2 JP5833492B2 JP2012097507A JP2012097507A JP5833492B2 JP 5833492 B2 JP5833492 B2 JP 5833492B2 JP 2012097507 A JP2012097507 A JP 2012097507A JP 2012097507 A JP2012097507 A JP 2012097507A JP 5833492 B2 JP5833492 B2 JP 5833492B2
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- MQVCTPXBBSKLFS-UHFFFAOYSA-N tri(propan-2-yloxy)-propylsilane Chemical compound CCC[Si](OC(C)C)(OC(C)C)OC(C)C MQVCTPXBBSKLFS-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- USLHPQORLCHMOC-UHFFFAOYSA-N triethoxygallane Chemical compound CCO[Ga](OCC)OCC USLHPQORLCHMOC-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- QFCVQKSWGFVMTB-UHFFFAOYSA-N trihexoxyalumane Chemical compound [Al+3].CCCCCC[O-].CCCCCC[O-].CCCCCC[O-] QFCVQKSWGFVMTB-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- XIYWAPJTMIWONS-UHFFFAOYSA-N trimethoxygallane Chemical compound [Ga+3].[O-]C.[O-]C.[O-]C XIYWAPJTMIWONS-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 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
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- YWIUPWSLDVUCDT-UHFFFAOYSA-N tris(1-methoxyethoxy)alumane Chemical compound [Al+3].COC(C)[O-].COC(C)[O-].COC(C)[O-] YWIUPWSLDVUCDT-UHFFFAOYSA-N 0.000 description 1
- IYGPXXORQKFXCZ-UHFFFAOYSA-N tris(2-methoxyethyl) borate Chemical compound COCCOB(OCCOC)OCCOC IYGPXXORQKFXCZ-UHFFFAOYSA-N 0.000 description 1
- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- HODZVVUWYZMUHG-UHFFFAOYSA-K yttrium(3+) triphenoxide Chemical compound [Y+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 HODZVVUWYZMUHG-UHFFFAOYSA-K 0.000 description 1
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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
- G03F7/004—Photosensitive materials
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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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
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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
- G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
- G03F7/0043—Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
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- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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Description
従来、ポジ型フォトレジストでは、露光前のフォトレジスト膜の膜質と露光後のアルカリ現像で形成されたパターン(以後、ポジ型パターンと呼ぶ)の膜質は同じ膜質である。そこで、ポジ型パターンとレジスト下層膜との密着性を向上させるために、フォトレジストとレジスト下層膜の純水に対する接触角(以後、接触角と呼ぶ)を近似させることで、ポジ型パターンとレジスト下層膜との密着性向上やラフネスの低減に効果があった。
原料のフェノール化合物に酸不安定基を導入する。
酸不安定基としては、3級アルキル基やアルコキシアルキル基(アセタール基)が好ましい。
また、原料のフェノール化合物としては、以下のものを挙げることができる。
典型的な方法としては、前記の方法で得られたフェノール化合物をもとに有機金属試薬を調製し、該有機金属試薬とアルコキシシランの置換反応で製造できる。有機金属試薬とアルコキシシランの量比を変えることで、k=1のケイ素化合物かk=2のケイ素化合物を選択的に製造することが可能である。
U(OR7)m7(OR8)m8 (1)
(式中、R7、R8は炭素数1〜30の有機基であり、m7+m8はUの種類により決まる価数と同数であり、m7、m8は0以上の整数、Uは周期律表のIII族、IV族、又はV族の元素で炭素及びケイ素を除くものである。)
(合成方法1:酸触媒)
本発明のケイ素含有化合物は、本発明のケイ素化合物と上記加水分解性モノマーまたは加水分解性金属化合物を酸触媒の存在下、加水分解縮合を行うことで得ることができる。
また、ケイ素含有化合物は、モノマーをアルカリ触媒の存在下、加水分解縮合を行うことで得ることができる。このとき使用されるアルカリ触媒は、メチルアミン、エチルアミン、プロピルアミン、ブチルアミン、エチレンジアミン、ヘキサメチレンジアミン、ジメチルアミン、ジエチルアミン、エチルメチルアミン、トリメチルアミン、トリエチルアミン、トリプロピルアミン、トリブチルアミン、シクロヘキシルアミン、ジシクロヘキシルアミン、モノエタノールアミン、ジエタノールアミン、ジメチルモノエタノールアミン、モノメチルジエタノールアミン、トリエタノールアミン、ジアザビシクロオクタン、ジアザビシクロシクロノネン、ジアザビシクロウンデセン、ヘキサメチレンテトラミン、アニリン、N,N−ジメチルアニリン、ピリジン、N,N−ジメチルアミノピリジン、ピロール、ピペラジン、ピロリジン、ピペリジン、ピコリン、テトラメチルアンモニウムハイドロオキサイド、コリンハイドロオキサイド、テトラプロピルアンモニウムハイドロオキサイド、テトラブチルアンモニウムハイドロオキサイド、アンモニア、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化バリウム、水酸化カルシウム等を挙げることができる。触媒の使用量は、ケイ素モノマー1モルに対して1×10−6モル〜10モル、好ましくは1×10−5モル〜5モル、より好ましくは1×10−4モル〜1モルである。
本発明においては、熱架橋促進剤をケイ素含有レジスト下層膜形成用組成物に配合してもよい。配合可能な熱架橋促進剤として、下記一般式(2)又は(3)で示される化合物を挙げることができる。具体的には、特許文献6に記載されている材料を添加することができる。
LaHbX (2)
(式中、Lはリチウム、ナトリウム、カリウム、ルビジウム又はセシウム、Xは水酸基、
又は炭素数1〜30の1価又は2価以上の有機酸基であり、aは1以上の整数、bは0又
は1以上の整数で、a+bは水酸基又は有機酸基の価数である。)
MY (3)
(式中、Mはスルホニウム、ヨードニウム又はアンモニウムであり、Yは非求核性対向イ
オンである。)
本発明のケイ素含有レジスト下層膜形成用組成物の安定性を向上させるため、炭素数が1〜30の1価又は2価以上の有機酸を添加することが好ましい。このとき添加する酸としては、ギ酸、酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、オレイン酸、ステアリン酸、リノール酸、リノレン酸、安息香酸、フタル酸、イソフタル酸、テレフタル酸、サリチル酸、トリフルオロ酢酸、モノクロロ酢酸、ジクロロ酢酸、トリクロロ酢酸、シュウ酸、マロン酸、メチルマロン酸、エチルマロン酸、プロピルマロン酸、ブチルマロン酸、ジメチルマロン酸、ジエチルマロン酸、コハク酸、メチルコハク酸、グルタル酸、アジピン酸、イタコン酸、マレイン酸、フマル酸、シトラコン酸、クエン酸等を例示することができる。特にシュウ酸、マレイン酸、ギ酸、酢酸、プロピオン酸、クエン酸等が好ましい。また、安定性を保つため、2種以上の酸を混合して使用してもよい。添加量は組成物に含まれるケイ素100質量部に対して0.001〜25質量部、好ましくは0.01〜15質量部、より好ましくは0.1〜5質量部である。
本発明では組成物に水を添加してもよい。水を添加すると、組成物中のポリシロキサン化合物が水和されるため、リソグラフィー性能が向上する。水を添加する場合、組成物の溶剤成分における水の含有率は0質量%を超え50質量%未満であり、より好ましくは0.3〜30質量%、更に好ましくは0.5〜20質量%である。それぞれの成分は、添加量が多すぎると、ケイ素含有レジスト下層膜の均一性が悪くなり、最悪の場合はじきが発生してしまう恐れがある。一方、添加量が少ないとリソグラフィー性能が低下する恐れがある。
本発明では組成物に光酸発生剤を添加してもよい。本発明で使用される光酸発生剤として、具体的には、特開2009−126940号公報(0160)〜(0179)段落に記載されている材料を添加することができる。
更に、本発明では組成物に安定剤を添加することができる。安定剤として環状エーテルを置換基として有する1価又は2価以上のアルコールを添加することができる。特に特開2009−126940号公報(0181)〜(0182)段落に記載されている安定剤を添加するとケイ素含有レジスト下層膜形成用組成物の安定性を向上させることができる。
更に、本発明では必要に応じて組成物に界面活性剤を配合することが可能である。このようなものとして、具体的には、特開2009−126940号公報(0185)段落に記載されている材料を添加することができる。
更に、本発明では必要に応じて組成物に沸点が180度以上の高沸点溶剤を添加する事も可能である。この高沸点溶剤としては、1−オクタノール、2−エチルヘキサノール、1−ノナノール、1−デカノール、1−ウンデカール、エチレングリコール、1,2−プロピレングリコール、1,3−ブチレングリコール、2,4−ペンタンジオール、2−メチル−2,4−ペンタンジオール、2,5−ヘキサンジオール、2,4−ヘプタンジオール、2−エチル−1,3−ヘキサンジオール、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコール、グリセリン、酢酸n−ノニル、酢酸エチレングリコールモノエチルエーテル、1,2−ジアセトキシエタン、1−アセトキシ−2−メトキシエタン、1,2−ジアセトキシプロパン、酢酸ジエチレングリコールモノメチルエーテル、酢酸ジエチレングリコールモノエチルエーテル、酢酸ジエチレングリコールモノ−n−ブチルエーテル、酢酸プロピレングリコールモノメチルエーテル、酢酸プロピレングリコールモノプロピルエーテル、酢酸プロピレングリコールモノブチルエーテル、酢酸ジプロピレングリコールモノメチルエーテル、酢酸ジプロピレングリコールモノエチルエーテルなどを挙げることができる。
(ネガ型パターン形成方法1)
本発明では、被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に前記ケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、有機溶剤の現像液を用いて前記フォトレジスト膜の未露光部を溶解させることによりネガ型パターンを形成し、該ネガ型パターンが形成されたフォトレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機下層膜にドライエッチングでパターン転写し、さらに該パターンが転写された有機下層膜をマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法を提供する(所謂「多層レジスト法」)。
また、本発明では、被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に前記ケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、有機溶剤の現像液を用いて前記フォトレジスト膜の未露光部を溶解させることによりネガ型パターンを形成し、該ネガ型パターンが形成されたフォトレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機ハードマスクにドライエッチングでパターン転写し、さらに該パターンが転写された前記有機ハードマスクをマスクにして被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法を提供する。
以上のような3層レジスト法による本発明のネガ型パターン形成方法は次の通りである(図1参照)。このプロセスにおいては、まず被加工体1上に有機下層膜2をスピンコートで作製する(図1(I−A))。この有機下層膜2は、被加工体1をエッチングするときのマスクとして作用するので、エッチング耐性が高いことが望ましく、上層のケイ素含有レジスト下層膜とミキシングしないことが求められるため、スピンコートで形成した後に熱あるいは酸によって架橋することが望ましい。
(ポジ型パターン形成方法1)
また、本発明では、被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に前記ケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、アルカリ現像液を用いて前記フォトレジスト膜の露光部を溶解させることによりポジ型パターンを形成し、該ポジ型パターンが形成されたフォトレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写された前記ケイ素含有レジスト下層膜をマスクにして前記有機下層膜にドライエッチングでパターン転写し、さらに該パターンが転写された有機下層膜をマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法を提供する。
また、本発明では、被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に上記ケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、アルカリ現像液を用いて前記フォトレジスト膜の露光部を溶解させることによりポジ型パターンを形成し、該ポジ型パターンが形成されたフォトレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機ハードマスクにドライエッチングでパターン転写し、さらに該パターンが転写された有機ハードマスクをマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法を提供する。
3層レジスト法による本発明のポジ型パターン形成方法は次の通りである(図1参照)。このプロセスにおいては、まず被加工体1上に有機下層膜2をスピンコートで作製する(図1(II−A))。この有機下層膜2は、被加工体1をエッチングするときのマスクとして作用するので、エッチング耐性が高いことが望ましく、上層のケイ素含有レジスト下層膜とミキシングしないことが求められるため、スピンコートで形成した後に熱あるいは酸によって架橋することが望ましい。
[合成例1−1]ケイ素化合物1の合成
1H−NMR(600MHz in DMSO−d6):δ=1.25(9H、s)、1.31(9H、s)、6.86(1H、dd、J=8.7、2.8Hz)、7.02(1H、d、J=2.8Hz)、7.08(1H、d、J=8.7Hz)ppm。
IR(D−ATR):ν=2978、2934、1595、1558、1484、1391、1366、1260、1206、1159、1047、940、925、898、883、850、799、683、648、611、581cm−1。
1H−NMR(600MHz in DMSO−d6):δ=1.22(9H、s)、1.38(9H、s)、3.50(9H、s)、6.95(1H、dd、J=9.0、2.9Hz)、7.01(1H、d、J=2.9Hz)、7.02(1H、d、J=9.0Hz)ppm。
IR(D−ATR):ν=2976、2942、2840、1566、1471、1389、1365、1262、1214、1163、1088、929、900、852、814、748、724、662cm−1。
1H−NMR(600MHz in CDCl3):δ=1.273(18H、s)、6.471(1H、dd、J=1.8Hz)、6.671(2H,d、J=1.8Hz)ppm。
13C−NMR(150MHz、in CDCl3):δ=28.81、79.40、118.34、119.51、133.36、156.34ppm。
IR(D−ATR)2973、2932、2903、2871、1589、1574、1471、1458、1428、1390、1363、1282、1261、1242、175、1129、1084、1037、1010、929、907、893、872、860、832、736、701、607cm−1。
1H−NMR(600MHz in CDCl3):δ=1.015(18H、s)、3.275(9H、s)、6.421(1H、dd、J=1.8Hz)、6.682(2H、d、1.8Hz)ppm。
13C−NMR(150MHz、in CDCl3):δ= 28.83、50.80、78.64、122.71、125.43、129.74、155.56ppm。
IR(D−ATR)2977、2942、2840、1572、1475、1402、1391、1366、1284、1259、1237、1182、1133、1086、1035、1007、939、899、837、813、750、717、691cm−1。
[製造例1−1]
メタノール200g、メタンスルホン酸0.1g及び脱イオン水60gの混合物に[モノマー1]30.6g、[モノマー2]38.1g及び[モノマー20]9.6gの混合物を添加し、12時間、40℃に保持し、加水分解縮合させた。反応終了後、プロピレングリコールエチルエーテル(PGEE)200gを加え、副生アルコールを減圧で留去した。そこに、酢酸エチル1000ml及びPGEE300gを加え、水層を分液した。残った有機層に、イオン交換水100mlを加えて撹拌、静置、分液した。これを3回繰り返した。残った有機層を減圧で濃縮してケイ素含有化合物1−1のPGEE溶液350g(化合物濃度10%)を得た。このもののポリスチレン換算分子量を測定したところMw=2,300であった。
メタノール120g、70%硝酸0.1g及び脱イオン水60gの混合物に[モノマー0]5.0g、[モノマー1]3.4g、及び[モノマー2]68.5gの混合物を添加し、12時間、40℃に保持し、加水分解縮合させた。反応終了後、PGEE300gを加え、副生アルコール及び過剰の水を減圧で留去して、ポリシロキサン化合物1−19のPGEE溶液310g(ポリマー濃度10%)を得た。このもののポリスチレン換算分子量を測定したところMw=3,400であった。
上記製造例で得られたケイ素含有化合物(1−1)〜(1−26)、酸、熱架橋促進剤、溶剤、添加剤を表2,3に示す割合で混合し、0.1μmのフッ素樹脂製のフィルターで濾過することによって、ケイ素含有レジスト下層膜形成用組成物溶液をそれぞれ調製し、それぞれSol.1〜38とした。
TPSHCO3 :炭酸モノ(トリフェニルスルホニウム)
TPSOx :シュウ酸モノ(トリフェニルスルホニウム)
TPSTFA :トリフルオロ酢酸トリフェニルスルホニウム
TPSOCOPh :安息香酸トリフェニルスルホニウム
TPSH2PO4 :リン酸モノ(トリフェニルスルホニウム)
TPSMA :マレイン酸モノ(トリフェニルスルホニウム)
TPSNf :ノナフルオロブタンスルホン酸トリフェニルスルホニウム
QMAMA :マレイン酸モノ(テトラメチルアンモニウム)
QMATFA :トリフルオロ酢酸テトラメチルアンモニウム
QBANO3 :硝酸テトラブチルアンモニウム
Ph2ICl :塩化ジフェニルヨードニウム
PGEE :プロピレングリコールエチルエーテル
GBL :ガンマブチルラクトン
シリコンウエハー上に、ケイ素含有レジスト下層膜形成用組成物Sol.1〜38を塗布して240℃で60秒間加熱して、膜厚35nmのケイ素含有膜Film1〜38を作製した。更にその上に表8記載のArFレジスト溶液(PR−1)を塗布し、100℃で60秒間ベークして膜厚100nmのフォトレジスト層を形成した。次いで、レジスト膜を全てプロピレングリコールモノメチルエーテル(PGME)でリンス除去し、ケイ素含有膜の未露光部と同等の膜を得た。これらについて、純水との接触角(CA1)を測定した(表4)。
シリコンウエハー上に、ケイ素含有レジスト下層膜形成用組成物Sol.1〜38を塗布して240℃で60秒間加熱して、膜厚35nmのケイ素含有膜Film1〜38を作製した。その上に表11記載のネガ現像用ArFレジスト溶液(PR−2)を塗布し、100℃で60秒間ベークして膜厚100nmのフォトレジスト層を形成した。更にフォトレジスト膜上に表9記載の液浸保護膜(TC−1)を塗布し90℃で60秒間ベークし膜厚50nmの保護膜を形成した。次いで、ArF液浸露光装置((株)ニコン製;NSR−S610Cで全面露光し、100℃で60秒間ベーク(PEB)し、30rpmで回転させながら現像ノズルから現像液として酢酸ブチルを3秒間吐出し、その後回転を止めてパドル現像を27秒間行い、ジイソアミルエーテルでリンス後スピンドライし、100℃で20秒間ベークしてリンス溶剤を蒸発させた。残ったレジスト膜を全てPGMEでリンス除去した後、ケイ素含有膜の露光部の膜を得た。これらについて、純水との接触角(CA2)を測定した(表5)。
シリコンウエハー上に表8記載のArFレジスト溶液(PR−1)を塗布し、100℃で60秒間ベークして膜厚100nmのフォトレジスト膜を形成し、純水との接触角を測定した(表6)。
シリコンウエハー上に表11記載のネガ現像用ArFレジスト溶液(PR−2)を塗布し、100℃で60秒間ベークして膜厚100nmのフォトレジスト膜を作製し、純水との接触角を測定した。次いで、同じレジスト膜をArF液浸露光装置((株)ニコン製;NSR−S610C)で全面露光し、100℃で60秒間ベーク(PEB)して、ジイソアミルエーテルでリンス後スピンドライし、100℃で20秒間ベークしてリンス溶剤を蒸発させて、酸脱離基が外れたネガ現像時のパターン部分に相当するArFレジスト膜を作製し、純水との接触角を測定した(表7)。
更に表5に示されている露光後のケイ素含有膜の接触角(CA2)は、ベンゼン環上の水酸基が一つしかないFilm38と比べると非常に低くなったことが分かった。
ポジ型現像によるパターニング試験
次いで、これをArF液浸露光装置((株)ニコン製;NSR−S610C,NA1.30、σ0.98/0.65、35度ダイポール偏光照明、6%ハーフトーン位相シフトマスク、45nm 1:1ラインアンドスペースパターン)で露光量を変化させて露光し、100℃で60秒間ベーク(PEB)し、2.38質量%テトラメチルアンモニウムヒドロキシド(TMAH)水溶液で30秒間現像した。得られたパターンから、パターン倒れが発生しない最大露光量におけるパターン寸法を(株)日立ハイテクノロジーズ製電子顕微鏡(CG4000)で測定し、断面形状を(株)日立製作所製電子顕微鏡(S−9380)で測定した(表10)。
分子量(Mw)=7,800
分散度(Mw/Mn)=1.78
分子量(Mw)=8,800
分散度(Mw/Mn)=1.69
シリコンウエハー上に、信越化学工業(株)製スピンオンカーボン膜ODL−50(カーボン含有量80質量%)を膜厚200nmで形成した。その上にケイ素含有レジスト下層膜形成用組成物Sol.11〜38を塗布して240℃で60秒間加熱して、膜厚35nmのケイ素含有膜Film11〜38を作製した。
Claims (9)
- 請求項2に記載のポリシロキサン化合物及び溶剤を含むものであることを特徴とするケイ素含有レジスト下層膜形成用組成物。
- 被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に請求項3に記載のケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、アルカリ現像液を用いて前記フォトレジスト膜の露光部を溶解させることによりポジ型パターンを形成し、該パターンが形成されたフォトレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機下層膜にドライエッチングでパターン転写し、さらに該パターンが転写された有機下層膜をマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法。
- 被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に請求項3に記載のケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、アルカリ現像液を用いて前記フォトレジスト膜の露光部を溶解させることによりポジ型パターンを形成し、該パターンが形成されたフォトレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機ハードマスクにドライエッチングでパターン転写し、さらに該パターンが転写された有機ハードマスクをマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法。
- 被加工体上に塗布型有機下層膜材料を用いて有機下層膜を形成し、該有機下層膜の上に請求項3に記載のケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、有機溶剤の現像液を用いて前記フォトレジスト膜の未露光部を溶解させることによりネガ型パターンを形成し、該パターンが形成されたフォトレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機下層膜にドライエッチングでパターン転写し、さらに該パターンが転写された有機下層膜をマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法。
- 被加工体上に炭素を主成分とする有機ハードマスクをCVD法で形成し、該有機ハードマスクの上に請求項3に記載のケイ素含有レジスト下層膜形成用組成物を用いてケイ素含有レジスト下層膜を形成し、該ケイ素含有レジスト下層膜上に化学増幅型レジスト組成物を用いてフォトレジスト膜を形成し、加熱処理後に高エネルギー線で前記フォトレジスト膜を露光し、有機溶剤の現像液を用いて前記フォトレジスト膜の未露光部を溶解させることによりネガ型パターンを形成し、該パターンが形成されたフォトレジスト膜をマスクにして前記ケイ素含有レジスト下層膜にドライエッチングでパターン転写し、該パターンが転写されたケイ素含有レジスト下層膜をマスクにして前記有機ハードマスクにドライエッチングでパターン転写し、さらに該パターンが転写された有機ハードマスクをマスクにして前記被加工体にドライエッチングでパターンを転写することを特徴とするパターン形成方法。
- 前記被加工体として、半導体装置基板又は半導体装置基板に金属膜、合金膜、金属炭化膜、金属酸化膜、金属窒化膜、金属酸化炭化膜、及び金属酸化窒化膜のいずれかが成膜されたものを使用することを特徴とする請求項4〜7に記載のパターン形成方法。
- 前記被加工体を構成する金属として、ケイ素、ガリウム、チタン、タングステン、ハフニウム、ジルコニウム、クロム、ゲルマニウム、銅、アルミニウム、及び鉄のいずれか、あるいはこれらの合金を使用することを特徴とする請求項8に記載のパターン形成方法。
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