JP5822358B2 - 縮合芳香環を含む反射防止コーティング組成物 - Google Patents
縮合芳香環を含む反射防止コーティング組成物 Download PDFInfo
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- JP5822358B2 JP5822358B2 JP2012545468A JP2012545468A JP5822358B2 JP 5822358 B2 JP5822358 B2 JP 5822358B2 JP 2012545468 A JP2012545468 A JP 2012545468A JP 2012545468 A JP2012545468 A JP 2012545468A JP 5822358 B2 JP5822358 B2 JP 5822358B2
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- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- XCCCHWWMLSAIOH-UHFFFAOYSA-N anthracen-1-ylmethanol Chemical compound C1=CC=C2C=C3C(CO)=CC=CC3=CC2=C1 XCCCHWWMLSAIOH-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- JOYKCMAPFCSKNO-UHFFFAOYSA-N chloro benzenesulfonate Chemical compound ClOS(=O)(=O)C1=CC=CC=C1 JOYKCMAPFCSKNO-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical class C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
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- 238000000609 electron-beam lithography Methods 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical group 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
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
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- 238000005194 fractionation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
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- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005525 methide group Chemical group 0.000 description 1
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- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- IVECIWLVOYDMRU-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O.COC(C)=O IVECIWLVOYDMRU-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000001127 nanoimprint lithography Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 150000002848 norbornenes Chemical group 0.000 description 1
- NYGSPCGCXLLSCZ-UHFFFAOYSA-N oct-1-ene-1,3-dione Chemical class CCCCCC(=O)C=C=O NYGSPCGCXLLSCZ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- SNGARVZXPNQWEY-UHFFFAOYSA-N phenylmethanediol Chemical compound OC(O)C1=CC=CC=C1 SNGARVZXPNQWEY-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
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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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- 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
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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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
- H01L21/04—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
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
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Description
9−アントラセンメタノール(52.06g/0.25モル)、ジビニルベンゼン(16.3g/0.125モル)を、攪拌器、凝縮器、サーモウォッチ、および窒素スイープを備えた2Lの四つ口丸底フラスコに導入した。窒素雰囲気下で213gのジ(エチレングリコール)ジメチルエーテル(ジグリム)および60gのシクロペンチルメチルエーテル(CPME)を添加し、10分間混合した。2.05gのトリフルオロメタンスルホン酸を添加して、10分間混合した。フラスコを140℃に加熱し、3時間還流させた。反応後、フラスコを冷却し、500mlのCPMEを添加した。反応混合物を、底出口弁を有する5Lのフラスコに移した。300mLの脱イオン(DI)水を添加し、混合し、水分離層が形成されるように静置した。ポリマー溶液を5Lのヘキサンと混合した。沈殿物を濾過し、ヘキサンで洗浄し、減圧下で乾燥させた。粗製ポリマー(46.0g)をテトラヒドロフラン(THF)400mlに溶解した。溶液に4Lのヘキサンを添加し、沈殿を形成させた。ポリマーの沈殿物を濾過し、ヘキサンで洗浄し、減圧下で乾燥させ収率54%、GPCのMwが1898、多分散性(Pd)が1.77のポリマーが得られた。得られたポリマーの元素分析は、質量%で炭素−92.29%、水素−5.91%、酸素−1.8%であった。
例1からの7.0gのポリマー、0.70gのテトラメトキシメチル−ビスフェノール(TMOM−BP)、シクロヘキサノン/PGMEA(70/30)中の10%の塩としてトリエチルアミンとともに2.80gのドデシルベンゼンスルホン酸、および89.5gのシクロヘキサノン/PGMEA(70/30)を混合した。完全な混合の後、配合物を0.04μmフィルターで濾過した。
例2の濾過した溶液を8”(インチ)のシリコン・ウェハ上に1500rpmでスピンコートした。コートされたウェハを、ホットプレート上で230℃、60秒間ベーク処理した。ウェハ表面からブレードにより薄くコートされた材料を掻き出し、そして元素分析を行った。その結果を表1に示す。例2の濾過した溶液を別のシリコン・ウェハ上に1500rpmでスピンコートし、そして、コートされたウェハを400℃、120秒間ベーク処理した。ウェハ表面からブレードによりベーク処理された材料を掻き出し、そして元素分析を行った。その結果を表1に示す。
ジビニルベンゼンに代えて、ジヒドロキシメチルベンゼンを使用して例2を繰り返した。得られたポリマーは、収率60%、GPCのMwが1374、Pdが1.79、元素分析は、質量%で:炭素−90.60%、水素−5.15%、酸素−2.53%であった。
比較例1のポリマーを使用して例2を繰り返した。
比較例2の材料を使用して例2を繰り返し、そして得られた結果を下の表2に示す。
ジビニルベンゼンに代えて、ジメトキシメチルベンゼンを使用して例1を繰り返した。得られたポリマーはMw1374、Pd1.79であった。元素分析から、ポリマーは炭素−90.60%、水素−5.15%および酸素−4.25%(質量%)有している。
比較例4のポリマーを使用して比較例2を繰り返した。
比較例5の材料を使用して比較例3を繰り返し、そして得られた結果を下の表3に示す。
nおよびk測定:例2からの配合物をシクロヘキサノンで固形分1.25%に調節し、全ての物質が溶解するまで、混合物を混合した。均一な溶液を0.2μm膜フィルターで濾過した。この濾過された溶液を、4インチのシリコン・ウェハに2000rpmでスピン・コーティングした。コーティングされたウェハをホットプレート上、230℃で60秒間ベーク処理した。次いで、nおよびk値をJ.A. Woollam Co.Inc.製のVASE Ellipsometerで測定した。193nm放射線での被膜の光学定数nおよびkは、n=1.47、k=0.56であった。
例2の均質な溶液を0.2μm膜フィルターで濾過した。この濾過された溶液を、6インチのシリコン・ウェハに1500rpmでスピン・コーティングした。コーティングされたウェハをホットプレート上、230℃で60秒間ベーク処理した。ベーク処理の後、ウェハを室温に冷却し、PGME中に30秒間部分的に浸漬した。コーティングに損傷はなかった。ウェハの浸漬した部分と浸漬してない部分の被膜厚の変化を測定した。ベーク処理された膜の効果的な架橋のため、浸漬した部分に膜の損傷は見られなかった。
Perkin Elmer TGA 7を使用して、例1のポリマーの等温熱重量分析TGAを400℃、120分間で測定したところ、その結果はポリマーの質量損失は2.27%であり、したがって、新規なポリマーが非常に最小限の質量損失であることを示している。
表4に示した酸化的(酸素リッチ)エッチング条件およびフルオロカーボンリッチエッチング条件の両方を使用して、NE−5000N(ULVAC)上で反射防止コーティングのブランケットエッチング速度を測定した。例2および比較例2の配合物の反射防止コーティング膜を約250nmの被膜厚で、別々に、8インチのシリコン・ウェハにコーティングし、そして230℃で1分間ベーク処理した。膜のVASE分析によるCauchyの材料依存の定数および5点検討を使用したNanospec 8000の個々の被膜厚測定プログラムを20秒エッチングの前後で行った。ここで、エッチング速度はエッチング時間で分割された被膜厚の差をとることにより計算した。エッチング速度のマスキング能は、表5および6のエッチング速度データ中に示した。より低いエッチング速度が望まれるなか、比較例2は例2より高いエッチング速度を示した。
例2の組成物を1500rpmで8インチのシリコン・ウェハにコーティングし、200nmの被膜厚を得て、350℃、120秒でベーク処理した。シリコン含有底反射防止コーティングAZ(登録商標) EXP ArF S24H(AZ(登録商標)Electronic Materials USA Corps,Somerville,NJより利用可能なシリコン反射防止コーティング)をその頂部にコーティングし、31nmの被膜厚を得て、230℃、60秒でベーク処理した。その後、AZ(登録商標)ArF2110P フォトレジスト(AZ(登録商標)Electronic Materials USA Corps,Somerville,NJ)から利用可能な193nmフォトレジスト)を反射防止コーティングの頂部にコーティングし、125nmの被膜厚を得て、100℃、60秒でベーク処理した。193nmの露光ツール(Nikon NSR−306D:NA=0.85,Dipole0.82/0.43)により、フォトレジストを像様露光し、110℃、60秒でベーク処理し、その後、0.26N水性水酸化テトラメチルアンモニウム(TMAH)溶液中で現像した。次に、ラインとスペースパターンを走査型電子顕微鏡(SEM)により観察し、50nmの限界寸法で1:2のピッチでパターンを分析した。フォトレジストは48.0mJ/cm2の感光性を有していた。フォトレジスト・パターンは、フォトレジスト・パターンの底にフーチング(footing)や屑がない良好なパターンプロファイルを示した。フォトレジスト・パターンは、基板からパターンへ最少の反射を示す定常波を有さない。フォトレジスト・パターンは、前記のエッチング条件、または他の任意の条件により基板に転写する。パターンサンプルはCF4ガスを使用してエッチングし、続いてO2ガスを使用して、全ての残留有機物を除去する。続いて、基板をCF4ガスによりエッチングする。パターンの断面を、走査型電子顕微鏡(SEM)を使用して観察する。
9−アントラセンメタノール(166.6g/0.80モル)、ジビニルベンゼン(16.3g/0.125モル)を、攪拌器、凝縮器、サーモウォッチ、および窒素スイープを備えた2Lの四つ口丸底フラスコに導入した。窒素雰囲気下で500gのジ(エチレングリコール)ジメチルエーテル(ジグリム)ジ(エチレングリコール)ジメチルエーテル(ジグリム)および150gのシクロペンチルメチルエーテルを添加し、10分間混合した。6.5gのトリフルオロメタンスルホン酸を添加して、10分間混合した。フラスコを140℃に加熱し、3時間還流させた。反応後、フラスコを冷却し、500mlのCPMEを添加した。400mLの脱イオン(DI)水を添加し、混合し、水分離層が形成されるように静置した。水層を除去した。ポリマー溶液を8Lのヘキサンと混合した。沈殿物を濾過し、ヘキサンで洗浄し、減圧下で乾燥させた。粗製ポリマー(154g)をテトラヒドロフラン(1386g)に溶解した。この溶液に824gのヘキサンを攪拌しながらゆっくり添加し、沈殿を形成させた。沈殿物を濾過し、ヘキサンで洗浄し、減圧下で乾燥させ収率38%の分画されたポリマーが得られた;GPCのMwが2162、多分散性(Pd)が1.83。
例13のポリマーを使用して例2を繰り返した。
例14の材料を使用して例3を繰り返し、そして得られた結果を下の表8に示す。
9−アントラセンメタノール(26g/0.125モル)、ジビニルベンゼン(16.25g/0.125モル)および1−ナフトール(18g/0.125モル)を、攪拌器、凝縮器、サーモウォッチ、および窒素スイープを備えた2Lの四つ口丸底フラスコに導入した。窒素雰囲気下で210gのジグリムおよび60gのシクロペンチルメチルエーテルを添加し、10分間混合した。1.81gのトリフルオロメタンスルホン酸を添加して、10分間混合した。フラスコを140℃に加熱し、3時間還流させた。反応後、フラスコを約80℃に冷却し、500mlのCPMEを添加し、1.3gのトリエチルアミンを添加した。反応混合物を、底出口弁を有する5Lのフラスコに移した。300mLのDI水を添加し、混合し、静置し、水分離層を形成させた。ポリマー溶液を3Lのヘキサンと混合した。沈殿物を濾過し、ヘキサンで洗浄し、減圧下で乾燥させた。ポリマー(70.0g)をTHF(200ml)に溶解した。溶液に3Lのt−ブチルメチルエーテルを添加し、沈殿を形成させた。沈殿物を濾過し、ヘキサンで洗浄し、減圧下で乾燥させた。ポリマーの収率は33%、GPCのMwが5561、Pdが2.04であった。元素分析:炭素−87.11%、水素−5.95%、酸素−6.95%
例13の7.35gの分画されたポリマーをボトルに添加し、1.84gの例16のポリマーを添加し、0.37gのTMOM−BPを添加し、シクロヘキサノン/PGMEA(70/30)中の2.94gのDBSAの10%溶液を添加し、70/30シクロヘキサノン/PGMEA中の1%の0.50gのFC−4430(3MCompany,MNより利用可能)および86.9gのシクロヘキサノン/PGMEA(70/30)を添加した。混合後、配合物を0.04μmのフィルターで濾過した。このろ液を1500rpmで8インチのシリコン・ウェハにスピン・コーティングした。コーティングされたウェハをホットプレート上で230℃、60分ベーク処理し、欠陥を検査した。コーティングには全く欠陥がなかった。
例17のポリマーを使用せずに、例17を繰り返し、検査の後、コーティングからはコーティングの欠陥が見られた。
Claims (15)
- 架橋剤および架橋剤で架橋することができる架橋可能なポリマーを含む反射防止コーティング組成物であって、架橋可能なポリマーが以下の構造(1)で示される単位を含み:
Bは構造(2)を有し、
上記組成物。 - 組成物中のポリマーが脂肪族多環式部分を含まない、請求項1に記載の組成物。
- R1がメチルであり、R2がメチルである、請求項1または2に記載の組成物。
- 組成物がさらに熱酸発生剤を含む、請求項1〜3のいずれか一つに記載の組成物。
- ポリマーが1200〜10000の重量平均分子量を有する、請求項1〜4のいずれか一つに記載の組成物。
- さらに界面活性剤を含む、請求項1〜5のいずれか一つに記載の組成物。
- さらに第二のポリマーを含み、第二のポリマーがヒドロキシ芳香族部分を含み、そして脂肪族多環を含まない、請求項1〜6のいずれか一つに記載の組成物。
- 固体含分で80%より大きい炭素含分を有する、請求項1〜7のいずれか一つに記載の組成物。
- マイクロ電子デバイスを製造する方法であって、
a)請求項1〜9のいずれか一つに記載の反射防止コーティング組成物の第一層を有する基板を提供し;
b)任意に、第一の反射防止コーティング組成物層の上に少なくとも第二の反射防止コーティング層を提供し;
b)反射防止コーティング層の上にフォトレジスト層をコーティングし;
c)フォトレジスト層を像様露光し;
d)水性アルカリ現像液でフォトレジスト層を現像する、ことを含む方法。 - 第一の反射防止コーティング層が0.05〜1.0の範囲のk値を有し、かつ/または、第二の反射防止コーティング層が0.05〜0.5の範囲のk値を有する、請求項10に記載の方法。
- 第二の反射防止コーティング層がシリコンを含む、請求項10または11に記載の方法。
- フォトレジストが240nm〜12nmの放射線でイメージング可能である、請求項10〜12のいずれか一つに記載の方法。
- 現像液が水酸基塩基を含む水性溶液である、請求項10〜13のいずれか一つに記載の方法。
- マイクロ電子デバイスを製造する方法であって、
a)架橋剤および架橋剤で架橋することができる架橋可能なポリマーを含む反射防止コーティング組成物の第一層を有する基板を提供し;
ここで、架橋可能なポリマーが以下の構造(1)で示される単位を含み:
Bは構造(2)を有し、
b)任意に、第一の反射防止コーティング組成物層の上に少なくとも第二の反射防止コーティング層を提供し;
b)反射防止コーティング層の上にフォトレジスト層をコーティングし;
c)フォトレジスト層を像様露光し;
d)水性アルカリ現像液でフォトレジスト層を現像する、ことを含む方法。
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KR101833075B1 (ko) | 2018-02-27 |
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