JPWO2019181873A1 - 保護されたフェノール基と硝酸を含むシリコン含有レジスト下層膜形成組成物 - Google Patents
保護されたフェノール基と硝酸を含むシリコン含有レジスト下層膜形成組成物 Download PDFInfo
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- JPWO2019181873A1 JPWO2019181873A1 JP2020507800A JP2020507800A JPWO2019181873A1 JP WO2019181873 A1 JPWO2019181873 A1 JP WO2019181873A1 JP 2020507800 A JP2020507800 A JP 2020507800A JP 2020507800 A JP2020507800 A JP 2020507800A JP WO2019181873 A1 JPWO2019181873 A1 JP WO2019181873A1
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- underlayer film
- resist
- resist underlayer
- hydrolyzable silane
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- 239000000203 mixture Substances 0.000 title claims abstract description 112
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 28
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title description 20
- 239000010703 silicon Substances 0.000 title description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 title description 9
- 229910017604 nitric acid Inorganic materials 0.000 title description 9
- 229910000077 silane Inorganic materials 0.000 claims abstract description 101
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- 239000004065 semiconductor Substances 0.000 claims abstract description 36
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 125000000962 organic group Chemical group 0.000 claims abstract description 16
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- 239000003513 alkali Substances 0.000 description 10
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- 229940006460 bromide ion Drugs 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
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- 238000000576 coating method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 238000010894 electron beam technology Methods 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
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- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 6
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- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 5
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- UXEMKWTVMQUHEH-UHFFFAOYSA-N dimethoxy-(methoxymethoxy)-phenylsilane Chemical compound COCO[Si](OC)(OC)C1=CC=CC=C1 UXEMKWTVMQUHEH-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
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- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 3
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- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- FFJVMNHOSKMOSA-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCCC([Si](OC)(OC)OC)OCC1CO1 FFJVMNHOSKMOSA-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- FNBIAJGPJUOAPB-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)C(CC)OCC1CO1 FNBIAJGPJUOAPB-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- GUKYSRVOOIKHHB-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCOCC1CO1 GUKYSRVOOIKHHB-UHFFFAOYSA-N 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- NBNZEBUNZGWIRJ-UHFFFAOYSA-N triphenylsulfanium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NBNZEBUNZGWIRJ-UHFFFAOYSA-N 0.000 description 1
- CGRJOQDFNTYSGH-UHFFFAOYSA-N tritylphosphane Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(P)C1=CC=CC=C1 CGRJOQDFNTYSGH-UHFFFAOYSA-N 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
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- G—PHYSICS
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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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- 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
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Abstract
Description
また、フィルターを経由する異物のろ過工程を経た後でも安定なポリシロキサンを含むレジスト下層膜形成組成物を提供することを目的とする。
第2観点として、加水分解性シラン(a)及び/又はその加水分解物(b)を更に含む第1観点に記載のレジスト下層膜形成組成物に関する。
第3観点として、硝酸イオンをレジスト下層膜形成組成物中に1ppm乃至1000ppmの範囲で含有する第1観点又は第2観点に記載のレジスト下層膜形成組成物に関する。
第4観点として、加水分解縮合物(c)は、式(1)の加水分解性シラン中の式(2)の官能基が(水素原子)/(水素原子+R5基)のモル比として1%乃至100%である第1観点乃至第3観点のいずれか一に記載のレジスト下層膜形成組成物に関する。
第5観点として、該加水分解性シラン(a)が、前記式(1)の加水分解性シランとその他の加水分解性シランの組み合わせであり、その他の加水分解性シランが式(3):
第6観点として、第1観点の前記式(1)の加水分解性シランと第5観点の前記式(3)の加水分解性シランの組み合わせからなる加水分解性シランの加水分解縮合物をポリマーとして含む第5観点に記載のレジスト下層膜形成組成物に関する。
第7観点として、更に水、酸、光酸発生剤、界面活性剤、金属酸化物、又はそれらの組み合わせをからなる添加剤を更に含む第1観点乃至第6観点のいずれか一に記載のレジスト下層膜形成組成物に関する。
第8観点として、加水分解性シランの加水分解縮合物(c)、又は加水分解性シランの加水分解縮合物(c)と加水分解性シラン(a)及び/又はその加水分解物(b)と、硝酸イオンと溶媒とを含むポリマー溶液を、極性基含有フィルターを含むフィルターで濾過する工程(A)を含む第1観点乃至第7観点のいずれか一に記載のレジスト下層膜形成組成物の製造方法に関する。
第9観点として、極性基含有フィルターがナイロン製フィルターである第8観点に記載のレジスト下層膜形成組成物の製造方法に関する。
第10観点として、ポリマー溶液に第7観点に記載の添加剤を加えた溶液をフィルターで濾過する工程(B)を更に加える第8観点又は第9観点に記載のレジスト下層膜形成組成物の製造方法に関する。
第11観点として、第1観点乃至第7観点のいずれか一に記載のレジスト下層膜形成組成物を半導体基板上に塗布し、焼成しレジスト下層膜を形成する工程、前記下層膜の上にレジスト用組成物を塗布しレジスト層を形成する工程、前記レジスト層を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、レジストパターンによりレジスト下層膜をエッチングする工程、及びパターン化されたレジスト層とレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法に関する。
第12観点として、半導体基板上に有機下層膜を形成する工程、その上に第1観点乃至第7観点のいずれか一に記載のレジスト下層膜形成組成物を塗布し焼成しレジスト下層膜を形成する工程、前記レジスト下層膜の上にレジスト用組成物を塗布しレジスト層を形成する工程、前記レジスト層を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、レジストパターンによりレジスト下層膜をエッチングする工程、パターン化されたレジスト下層膜により有機下層膜をエッチングする工程、及びパターン化された有機下層膜により半導体基板を加工する工程を含む半導体装置の製造方法に関する。
式(D−2):
式(D−3):
式(D−4):
式(D−5):
式(D−6):
酸発生剤としては、熱酸発生剤や光酸発生剤が挙げられる。
光酸発生剤は、レジストの露光時に酸を生ずる。そのため、下層膜の酸性度の調整ができる。これは、下層膜の酸性度を上層のレジストとの酸性度に合わせるための一方法である。また、下層膜の酸性度の調整によって、上層に形成されるレジストのパターン形状の調整ができる。
光酸発生剤が使用される場合、その割合としては、上記の加水分解性シランの加水分解縮合物(ポリオルガノシロキサン)(c)100質量部に対して、0.01質量部乃至5質量部、または0.1質量部乃至3質量部、または0.5質量部乃至1質量部である。
加える金属酸化物は上記の加水分解性シランの加水分解縮合物(ポリオルガノシロキサン)(c)100質量部に対して0.001質量部乃至100質量部とすることができる。
ここで半導体装置の製造に使用される基板(例えば、シリコンウエハー基板、シリコン/二酸化シリコン被覆基板、シリコンナイトライド基板、ガラス基板、ITO基板、ポリイミド基板、及び低誘電率材料(low−k材料)被覆基板等)の上に、スピナー、コーター等の適当な塗布方法により本発明のレジスト下層膜形成組成物が塗布され、その後、焼成することによりレジスト下層膜が形成される。焼成する条件としては、焼成温度80℃乃至250℃、焼成時間0.3分間乃至60分間の中から適宜、選択される。好ましくは、焼成温度150℃乃至250℃、焼成時間0.5分間乃至2分間である。ここで、形成される下層膜の膜厚としては、例えば、10nm乃至1000nmであり、または20nm乃至500nmであり、または50nm乃至300nmであり、または100nm乃至200nmである。
テトラエトキシシラン25.2g(全加水分解性シラン中で70モル%)、メチルトリエトキシシラン7.71g(全加水分解性シラン中で25モル%)、エトキシエトキシフェニルトリメトキシシラン2.48g(全加水分解性シラン中で5モル%)、アセトン53.1gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M硝酸水溶液11.5gを滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、プロピレングリコールモノメチルエーテルアセテート100%の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−1)に相当し、その後に式(3−1)と式(4−1)に相当するポリマーの混合物になった。GPCによる重量平均分子量(Mw)はポリスチレン換算で3000であった。
テトラエトキシシラン22.6g(全加水分解性シラン中で70モル%)、エトキシエトキシフェニルトリメトキシシラン13.3g(全加水分解性シラン中で30モル%)、アセトン53.8gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M硝酸水溶液10.3gを滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、プロピレングリコールモノメチルエーテルアセテート100%の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−2)に相当し、その後に式(3−2)と式(4−2)に相当するポリマーの混合物になった。GPCによる重量平均分子量(Mw)はポリスチレン換算で2700であった。
テトラエトキシシラン25.5g(全加水分解性シラン中で70モル%)、メチルトリエトキシシラン7.80g(全加水分解性シラン中で25モル%)、メトキシフェニルトリメトキシシラン2.00g(全加水分解性シラン中で5モル%)、アセトン53.0gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.1M硝酸水溶液11.7gを滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、プロピレングリコールモノメチルエーテルアセテート100%の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−3)に相当し、その後に式(3−3)と式(4−1)に相当するポリマーの混合物になった。GPCによる重量平均分子量(Mw)はポリスチレン換算で2800であった。
テトラエトキシシラン24.2g(全加水分解性シラン中で70モル%)、メトキシフェニルトリメトキシシラン11.37g(全加水分解性シラン中で30モル%)、アセトン53.4gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M硝酸水溶液11.1gを滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、プロピレングリコールモノメチルエーテルアセテート100%の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−4)に相当し、その後に式(3−4)と式(4−2)に相当するポリマーの混合物になった。GPCによる重量平均分子量(Mw)はポリスチレン換算で2200であった。
テトラエトキシシラン25.5g(全加水分解性シラン中で70モル%)、メチルトリエトキシシラン7.78g(全加水分解性シラン中で25モル%)、メトキシベンジルトリメトキシシラン2.11g(全加水分解性シラン中で5モル%)、アセトン53.0gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M硝酸水溶液11.6gを滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、プロピレングリコールモノメチルエーテルアセテート100%の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−5)に相当し、その後に式(3−5)と式(4−3)に相当するポリマーの混合物になった。GPCによる重量平均分子量(Mw)はポリスチレン換算で2400であった。
テトラエトキシシラン23.8g(全加水分解性シラン中で70モル%)、メトキシベンジルトリメトキシシラン11.9g(全加水分解性シラン中で30モル%)、アセトン53.5gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら1M硝酸水溶液10.8gを滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、プロピレングリコールモノメチルエーテルアセテート100%の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−6)に相当し、その後に式(3−6)と式(4−4)に相当するポリマーの混合物になった。GPCによる重量平均分子量(Mw)はポリスチレン換算で3500であった。
テトラエトキシシラン24.9g(全加水分解性シラン中で70モル%)、メチルトリエトキシシラン7.61g(全加水分解性シラン中で25モル%)、トリエトキシ((2−メトキシ−4−(メトキシメチル)フェノキシ)メチル)シラン2.94g(全加水分解性シラン中で5モル%)、アセトン53.2gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M硝酸水溶液11.4gを滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、プロピレングリコールモノメチルエーテルアセテート100%の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−7)に相当し、その後に式(3−7)、式(4−5)、式(4−7)に相当するポリマーの混合物になった。GPCによる重量平均分子量(Mw)はポリスチレン換算で2800であった。
テトラエトキシシラン21.1g(全加水分解性シラン中で70モル%)、トリエトキシ((2−メトキシ−4−(メトキシメチル)フェノキシ)メチル)シラン14.99g(全加水分解性シラン中で30モル%)、アセトン54.2gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M硝酸水溶液9.67gを滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、プロピレングリコールモノメチルエーテルアセテート100%の溶媒比率として140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(3−8)に相当し、その後に式(3−8)、式(4−6)、式(4−8)に相当するポリマーの混合物になった。GPCによる重量平均分子量(Mw)はポリスチレン換算で2500であった。
テトラエトキシシラン25.8g、トリエトキシメチルシラン9.5g、アセトン52.9gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら0.01M塩酸水溶液11.8gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、240分間、還流させた。その後、プロピレングリコールモノメチルエーテルアセテート70gを加え、アセトン、メタノール、エタノール、水を減圧留去し、濃縮して加水分解縮合物(ポリマー)水溶液を得た。さらにプロピレングリコールモノメチルエーテルアセテートを加え、140℃における固形残物換算で20重量パーセントとなるように調整した。得られたポリマーは式(5−1)に相当し、GPCによる重量平均分子量(Mw)はポリスチレン換算で1800であった。
テトラエトキシシラン25.8g、トリエトキシメチルシラン9.5g、アセトン52.9gを300mlのフラスコに入れ、混合溶液をマグネチックスターラーにて撹拌しながら11M硝酸水溶液11.8gを混合溶液に滴下した。添加後、85℃に調整されたオイルバスにフラスコを移し、その後アセトンを加え濃度調整を行い240分間、還流させた。その後、白色沈殿物が発生し、目的のポリマーが得られなかった。
ポリマー溶液中には10000ppmの硝酸イオンを含んでいた。
上記合成例で得られたポリシロキサン(ポリマー)を、孔径10nmのナイロン製のフィルターで濾過し、濾過前後での分子量変化をGPCスペクトル変化を用いて評価した。その結果、分子量変化が10%以下のものを良好、10%以上変化したものを不良とした。結果を表1に示す。
上記合成例で得られたポリシロキサン(ポリマー)、酸、溶媒を表1に示す割合で混合し、0.1μmのポリエチレン製のフィルターで濾過することによって、レジストパターンに塗布される組成物をそれぞれ調製した。表1中のポリマーの添加割合はポリマー溶液の添加量ではなく、ポリマー自体の添加量を示した。
表中で水は超純水を用いた。各添加量は質量部で示した。MAとはマレイン酸のことを指し、TPSNO3とはトリフェニルスルホニウムナイトレートのことを指し、TPSTFAはトリフェニルスルホニウムトリフルオロ酢酸塩のことを指し、TPSMLはトリフェニルスルホニウムマレイン酸塩のことを指し、TPSClとはトリフェニルスルホニウムクロライドのことを指し、BTEACとはベンジルトリエチルアンモニウムクロライドのことを指し、TMANO3とはテトラメチルアンモニウム硝酸塩の事を指し、TPSCSとはトリフェニルスルホニウムカンファ―スルホン酸塩のことを指し、TPSAdTfとはトリフェニルスルホニウムアダマンタンカルボン酸ブチルトリフルオロメタンスルホン酸塩の事を指し、PGEEはプロピレングリコールモノエチルエーテルを指し、PGMEAはプロピレングリコールモノメチルエーテルアセテートを指し、PGMEはプロピレングリコールモノメチルエーテルを指す。
窒素下、100mlの四口フラスコにカルバゾール(6.69g、0.040mol、東京化成工業(株)製)、9−フルオレノン(7.28g、0.040mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.76g、0.0040mol、東京化成工業(株)製)を加え、1,4−ジオキサン(6.69g、関東化学(株)製)を仕込み撹拌し、100℃まで昇温し溶解させ重合を開始した。24時間後60℃まで放冷後、クロロホルム(34g、関東化学(株)製)を加え希釈し、メタノール(168g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥し、目的とするポリマー(式(3−1)、以下PCzFLと略す)9.37gを得た。
1H−NMR(400MHz,DMSO−d6):δ7.03−7.55(br,12H),δ7.61−8.10(br,4H),δ11.18(br,1H)
PCzFLのGPCによるポリスチレン換算で測定される重量平均分子量(Mw)は2800、多分散度:Mw(重量平均分子量)/Mn(数平均分子量)は1.77であった。
得られた樹脂20gに、架橋剤としてテトラメトキシメチルグリコールウリル(三井サイテック(株)製、商品名パウダーリンク1174)3.0g、触媒としてピリジニウムパラトルエンスルホネート0.30g、界面活性剤としてメガファックR−30(DIC(株)製、商品名)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いる有機下層膜(A層)形成組成物の溶液を調製した。
実施例1乃至実施例8、比較例1乃至比較例2で調製したレジスト下層膜形成組成物をスピナーを用い、シリコンウェハー上に塗布した。ホットプレート上、215℃で1分間加熱し、レジスト下層膜をそれぞれ形成した。その後、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メチルエーテルアセテート=7/3(質量比)の溶剤をレジスト下層膜上に塗布、スピン乾燥し、溶剤塗布前後での膜厚の変化の有無を評価した。膜厚変化が1%以下のものを「良好」、膜厚変化が1%以上のものを「硬化せず」とした。結果を表4に示す。
実施例1乃至実施例8、比較例1乃至比較例2で調製したレジスト下層膜形成組成物をスピナーを用い、シリコンウェハー上に塗布した。ホットプレート上、215℃で1分間加熱し、レジスト下層膜をそれぞれ形成した。その後、アルカリ現像液(TMAH2.38%水溶液(TMAHとは水酸化テトラメチルアンモニウムのことを指す))をレジスト下層膜上に塗布、スピン乾燥し、溶剤塗布前後での膜厚の変化の有無を評価した。膜厚変化が1%以下のものを「良好」、膜厚変化が1%以上のものを「硬化せず」とした。結果を表4に併せて示す。
上記有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上、215℃で60秒間ベークし、膜厚90nmの有機下層膜(A層)を得た。その上に、実施例1乃至実施例8、比較例2で調製されたレジスト下層膜形成組成物溶液をスピンコートし、215℃で1分間加熱することにより、レジスト下層膜(B)層(20nm)が形成される。そのレジスト下層膜(ハードマスク)上に、EUV用レジスト溶液(メタクリレート樹脂系レジスト)をスピンコートし加熱を行い、EUVレジスト層(C)層を形成し、ASML製EUV露光装置(NXE3300B)を用い、NA=0.33、σ=0.67/0.90、cQuadの条件で露光する。露光後、PEBを行い、クーリングプレート上で室温まで冷却し、アルカリ現像液(2.38%TMAH水溶液)を用いて60秒現像し、リンス処理をし、レジストパターンを形成した。評価は、ピッチ40nmにて20nmのホールの形成可否、パターン断面観察によるパターン形状を評価した。結果を表5に示す。
表5で良好とはフッティングからアンダーカットの間の形状であり、かつスペース部に著しい残渣がないという状態を示し、倒れとはレジストパターンが剥がれ倒壊しているという好ましくない状態を示し、ブリッジとはレジストパターンの上部もしくは下部同士が接触しているという好ましくない状態を示す。
上記有機下層膜(A層)形成組成物をシリコンウエハー上に塗布し、ホットプレート上、215℃で60秒間ベークし、膜厚90nmの有機下層膜(A層)を得た。その上に、実施例1乃至実施例8、比較例2で調製されたレジスト下層膜形成組成物溶液をスピンコートし、215℃で1分間加熱することにより、レジスト下層膜(B)層(20nm)が形成される。そのレジスト下層膜(ハードマスク)上に、EUV用レジスト溶液(メタクリレート樹脂系レジスト)をスピンコートし加熱を行い、EUVレジスト層(C)層を形成し、ASML製EUV露光装置(NXE3300B)を用い、NA=0.33、σ=0.67/0.90、Dipoleの条件で露光する。露光後、PEBを行い、クーリングプレート上で室温まで冷却し、有機溶剤現像液(酢酸ブチル)を用いて60秒現像し、リンス処理をし、レジストパターンを形成した。評価は、20nmのラインアンドスペースの形成可否、パターン断面観察によるパターン形状を評価した。結果を表6に示す。
Claims (12)
- シランとして加水分解性シラン(a)の加水分解縮合物(c)と、硝酸イオンと溶媒とを含み、該加水分解性シラン(a)が式(1):
- 加水分解性シラン(a)及び/又はその加水分解物(b)を更に含む請求項1に記載のレジスト下層膜形成組成物。
- 硝酸イオンをレジスト下層膜形成組成物中に1ppm乃至1000ppmの範囲で含有する請求項1又は請求項2に記載のレジスト下層膜形成組成物。
- 加水分解縮合物(c)は、式(1)の加水分解性シラン中の式(2)の官能基が(水素原子)/(水素原子+R5基)のモル比として1%乃至100%である請求項1乃至請求項3のいずれか1項に記載のレジスト下層膜形成組成物。
- 該加水分解性シラン(a)が、前記式(1)の加水分解性シランとその他の加水分解性シランの組み合わせであり、その他の加水分解性シランが式(3):
- 請求項1の前記式(1)の加水分解性シランと請求項5の前記式(3)の加水分解性シランの組み合わせからなる加水分解性シランの加水分解縮合物をポリマーとして含む請求項5に記載のレジスト下層膜形成組成物。
- 水、酸、光酸発生剤、界面活性剤、金属酸化物、又はそれらの組み合わせをからなる添加剤を更に含む請求項1乃至請求項6のいずれか1項に記載のレジスト下層膜形成組成物。
- 加水分解性シランの加水分解縮合物(c)、又は加水分解性シランの加水分解縮合物(c)と加水分解性シラン(a)及び/又はその加水分解物(b)と、硝酸イオンと溶媒とを含むポリマー溶液を、極性基含有フィルターを含むフィルターで濾過する工程(A)を含む請求項1乃至請求項7のいずれか1項に記載のレジスト下層膜形成組成物の製造方法。
- 極性基含有フィルターがナイロン製フィルターである請求項8に記載のレジスト下層膜形成組成物の製造方法。
- ポリマー溶液に請求項7に記載の添加剤を加えた溶液をフィルターで濾過する工程(B)を更に加える請求項8又は請求項9に記載のレジスト下層膜形成組成物の製造方法。
- 請求項1乃至請求項7のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し、焼成しレジスト下層膜を形成する工程、前記下層膜の上にレジスト用組成物を塗布しレジスト層を形成する工程、前記レジスト層を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、レジストパターンによりレジスト下層膜をエッチングする工程、及びパターン化されたレジスト層とレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- 半導体基板上に有機下層膜を形成する工程、その上に請求項1乃至請求項7のいずれか1項に記載のレジスト下層膜形成組成物を塗布し焼成しレジスト下層膜を形成する工程、前記レジスト下層膜の上にレジスト用組成物を塗布しレジスト層を形成する工程、前記レジスト層を露光する工程、露光後にレジストを現像しレジストパターンを得る工程、レジストパターンによりレジスト下層膜をエッチングする工程、パターン化されたレジスト下層膜により有機下層膜をエッチングする工程、及びパターン化された有機下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
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