CN103827752B - 形成含有硅的euv抗蚀剂下层膜的组合物 - Google Patents
形成含有硅的euv抗蚀剂下层膜的组合物 Download PDFInfo
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- CN103827752B CN103827752B CN201280045182.3A CN201280045182A CN103827752B CN 103827752 B CN103827752 B CN 103827752B CN 201280045182 A CN201280045182 A CN 201280045182A CN 103827752 B CN103827752 B CN 103827752B
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- Prior art keywords
- lower membrane
- resist
- resist lower
- acid
- composition
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- 239000012528 membrane Substances 0.000 title claims abstract description 117
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- 239000010703 silicon Substances 0.000 title description 10
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- 230000015572 biosynthetic process Effects 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 40
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000001900 extreme ultraviolet lithography Methods 0.000 claims abstract description 20
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 19
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- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
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- 150000002367 halogens Chemical class 0.000 claims abstract description 10
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- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical group CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 24
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- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 11
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- 239000003054 catalyst Substances 0.000 description 9
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- 239000005011 phenolic resin Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
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- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
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- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 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
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- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- ADEHDBLQPSQEQU-UHFFFAOYSA-N trimethoxy-[4-(methoxymethoxy)phenyl]silane Chemical compound COCOC1=CC=C([Si](OC)(OC)OC)C=C1 ADEHDBLQPSQEQU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
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- 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
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
- B05D3/0254—After-treatment
- B05D3/0272—After-treatment with ovens
-
- 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
-
- 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
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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- G—PHYSICS
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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
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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- G—PHYSICS
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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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
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- G—PHYSICS
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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- 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
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
-
- 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
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
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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
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
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- 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
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
- H01L21/02137—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC the material comprising alkyl silsesquioxane, e.g. MSQ
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Abstract
本发明的课题是提供一种EUV抗蚀剂的曝光灵敏度提高,用EUV光曝光时释气发生少的光刻用抗蚀剂下层膜和用于形成该下层膜的形成抗蚀剂下层膜的组合物。作为解决本发明课题的方法涉及一种形成EUV光刻用抗蚀剂下层膜的组合物,其包含作为硅烷的水解性硅烷、其水解物、其水解缩合物、或它们的混合物,该水解性硅烷包含四甲氧基硅烷与烷基三甲氧基硅烷与芳基三烷氧基硅烷的组合,该芳基三烷氧基硅烷由下述式(1)表示:(式(1)中,R1表示由苯环或萘环构成的芳香族环、或者包含异氰脲酸结构的环,R2为芳香族环的氢原子的取代基,为卤原子或碳原子数1~10的烷氧基,X为碳原子数1~10的烷氧基、碳原子数2~10的酰氧基或卤基。)(R2)n2‑R1‑(CH2)n1‑si(X)3 (1)。
Description
技术领域
本发明涉及用于在半导体装置的制造中所使用的基板与抗蚀剂(例如,EUV抗蚀剂)之间形成下层膜的组合物。详细地说,涉及用于在半导体装置制造的光刻工序中形成在抗蚀剂的下层使用的下层膜的形成光刻用抗蚀剂下层膜的组合物。此外,涉及使用了该形成下层膜的组合物的抗蚀剂图案的形成方法。
背景技术
一直以来,在半导体装置的制造中,通过使用了光致抗蚀剂的光刻进行微细加工。上述微细加工为在硅片等半导体基板上形成光致抗蚀剂的薄膜,在其上介由描绘有半导体器件图案的掩模图案来照射紫外线等活性光线,进行显影,将所得的光致抗蚀剂图案作为保护膜对基板进行蚀刻处理,从而在基板表面形成与上述图案对应的微细凹凸的加工法。然而,近年来,半导体器件的高集成度化进展,所使用的活性光线也有从KrF准分子激光(248nm)向ArF准分子激光(193nm)、EUV光(13.5nm)短波长化的倾向。
需要这种程度以上地控制图形(抗蚀剂形状)、提高与基板的密合性。
此外,作为半导体基板与光致抗蚀剂之间的下层膜,使用了作为包含硅等金属元素的硬掩模而已知的膜。在该情况下,对于抗蚀剂和硬掩模,由于其构成成分有大的差异,因此它们的通过干蚀刻而被除去的速度很大程度依赖于干蚀刻中使用的气体种类。而且,通过适当地选择气体种类,不会导致光致抗蚀剂的膜厚的大幅减少,能够通过干蚀刻除去硬掩模。这样,在近年来的半导体装置的制造中,为了实现各种效果,渐渐在半导体基板与光致抗蚀剂之间配置抗蚀剂下层膜(参照专利文献1、2)。
而且,迄今为止也进行了抗蚀剂下层膜用组合物的研究,但从其要求特性的多样性等出发,期望开发出抗蚀剂下层膜用的新材料。
现有技术文献
专利文献
专利文献1:日本特开2008-076889
专利文献2:日本特开2010-237667
发明内容
发明所要解决的课题
本发明的目的是提供能够利用矩形抗蚀剂图案进行微细的基板加工,可以用于制造半导体装置的形成EUV光刻用抗蚀剂下层膜的组合物。本发明的目的,详细地说,是提供用于形成可作为硬掩模使用的抗蚀剂下层膜的形成光刻用抗蚀剂下层膜的组合物。此外,本发明的目的是提供EUV抗蚀剂的曝光灵敏度提高,不发生与抗蚀剂的混合,与抗蚀剂相比具有大的干蚀刻速度,用EUV光曝光时释气发生少的光刻用抗蚀剂下层膜和用于形成该下层膜的形成抗蚀剂下层膜的组合物。
用于解决课题的方法
本发明中,作为第1观点,是一种形成EUV光刻用抗蚀剂下层膜的组合物,其包含作为硅烷的水解性硅烷、其水解物、其水解缩合物、或它们的混合物,该水解性硅烷包含四甲氧基硅烷与烷基三甲氧基硅烷与芳基三烷氧基硅烷的组合,该芳基三烷氧基硅烷由下述式(1)表示,
(R2)n2-R1-(CH2)n1-Si(X)3 式(1)
(式(1)中,R1表示由苯环或萘环构成的芳香族环、或者包含异氰脲酸结构的环,R2为芳香族环内的氢原子的取代基,为卤原子或碳原子数1~10的烷氧基,X为碳原子数1~10的烷氧基、碳原子数2~10的酰氧基或卤基。n1为0或1的整数,在苯环的情况下,n2为1~5的整数,在萘环的情况下,n2为1~9的整数。),
作为第2观点,是第1观点所述的形成抗蚀剂下层膜的组合物,式(1)的R1为苯环,
作为第3观点,是第1观点或第2观点所述的形成抗蚀剂下层膜的组合物,式(1)的R2为甲氧基、甲氧基甲氧基、氟原子、氯原子或溴原子,
作为第4观点,是第1观点~第3观点的任一项所述的形成抗蚀剂下层膜的组合物,式(1)的X为甲氧基,
作为第5观点,是第1观点~第4观点的任一项所述的形成抗蚀剂下层膜的组合物,式(1)的n1为0,
作为第6观点,是第1观点~第5观点的任一项所述的形成抗蚀剂下层膜的组合物,烷基三甲氧基硅烷为甲基三甲氧基硅烷,
作为第7观点,是第1观点~第6观点的任一项所述的形成抗蚀剂下层膜的组合物,水解性硅烷以相对于四甲氧基硅烷70摩尔为10~35摩尔的比例包含烷基三甲氧基硅烷、为2~25摩尔的比例包含芳基三烷氧基硅烷,
作为第8观点,是权利要求1~7的任一项所述的形成抗蚀剂下层膜的组合物,上述硅烷,在全部硅烷中以甲氧基:乙氧基=100:0~80:20的比例(摩尔比)含有甲氧基和乙氧基作为水解性基团,
作为第9观点,是第1观点~第8观点的任一项所述的形成抗蚀剂下层膜的组合物,其还包含酸,
作为第10观点,是第1观点~第9观点的任一项所述的形成抗蚀剂下层膜的组合物,其还包含水,
作为第11观点,是第1观点~第10观点的任一项所述的形成抗蚀剂下层膜的组合物,其还包含铵化合物、环状铵化合物、环状胺化合物或化合物,
作为第12观点,是一种抗蚀剂下层膜,其为通过将第1观点~第11观点的任一项所述的形成抗蚀剂下层膜的组合物涂布在半导体基板上,进行烘烤而获得的,
作为第13观点,是一种半导体装置的制造方法,其包括下述工序:将第1观点~第11观点的任一项所述的形成抗蚀剂下层膜的组合物涂布在半导体基板上,进行烘烤,形成抗蚀剂下层膜的工序;在上述抗蚀剂下层膜上涂布抗蚀剂用组合物,形成抗蚀剂膜的工序;将上述抗蚀剂膜进行曝光的工序;在曝光后将上述抗蚀剂膜进行显影,获得抗蚀剂图案的工序;按照上述抗蚀剂图案对上述抗蚀剂下层膜进行蚀刻的工序;和按照被图案化了的上述抗蚀剂膜和上述抗蚀剂下层膜对上述半导体基板进行加工的工序,和
作为第14观点,是一种半导体装置的制造方法,其包括下述工序:在半导体基板上形成有机下层膜的工序;在该有机下层膜上涂布第1观点~第11观点的任一项所述的形成抗蚀剂下层膜的组合物,进行烘烤,形成抗蚀剂下层膜的工序;在上述抗蚀剂下层膜上涂布抗蚀剂用组合物,形成抗蚀剂膜的工序;将上述抗蚀剂膜进行曝光的工序;在曝光后将上述抗蚀剂膜进行显影,获得抗蚀剂图案的工序;按照上述抗蚀剂图案对上述抗蚀剂下层膜进行蚀刻的工序;按照被图案化了的上述抗蚀剂下层膜对上述有机下层膜进行蚀刻的工序;和按照被图案化了的上述有机下层膜对上述半导体基板进行加工的工序。
发明的效果
根据本发明,由该组合物通过EUV光刻形成的抗蚀剂下层膜可以作为对氧系干蚀刻气体具有耐干蚀刻性的硬掩模使用,使基板的微细加工容易。
此外,根据本发明,由该组合物形成的抗蚀剂下层膜可以使该下层膜上所设置的EUV抗蚀剂的曝光灵敏度提高。
此外,根据本发明,可以形成用EUV光曝光时释气发生少,不发生与抗蚀剂的混合,与抗蚀剂相比具有大的干蚀刻速度的光刻用抗蚀剂下层膜。
此外,根据本发明,通过适用该组合物,能够制造使用了具有这样良好的性能的抗蚀剂下层膜的半导体装置。
具体实施方式
在本发明中,通过涂布法在基板上形成抗蚀剂下层膜,或者介由基板上的有机下层膜通过涂布法在其上形成抗蚀剂下层膜,在该抗蚀剂下层膜上形成抗蚀剂膜(例如,EUV抗蚀剂)。然后,通过曝光和显影来形成抗蚀剂图案,使用该抗蚀剂图案对抗蚀剂下层膜进行干蚀刻来进行图案的转印,按照该图案对基板进行加工,或者通过对有机下层膜进行蚀刻进行图案转印,按照该有机下层膜进行基板加工。
在形成微细图案方面,为了防止图案倒塌而倾向于使抗蚀剂膜厚变薄。由于抗蚀剂的薄膜化,因而如果用于向存在于其下层的膜上转印图案的干蚀刻的蚀刻速度不高于上层的膜,则无法进行图案转印。在本发明中,在基板上,介由有机下层膜或不介由有机下层膜,在其上被覆本申请抗蚀剂下层膜(含有无机系硅系化合物),在其上依次被覆抗蚀剂膜(有机抗蚀剂膜)。通过选择蚀刻气体而使有机系成分的膜与无机系成分的膜的干蚀刻速度大不相同,有机系成分的膜在氧系气体下干蚀刻速度高,无机系成分的膜在含卤气体下干蚀刻速度高。
例如形成抗蚀剂图案,用含卤气体对存在于其下层的本申请抗蚀剂下层膜进行干蚀刻,从而在抗蚀剂下层膜上转印图案,使用含卤气体按照该被转印到抗蚀剂下层膜的图案来进行基板加工。或者,使用被图案转印了的抗蚀剂下层膜,利用氧系气体对其下层的有机下层膜进行干蚀刻,从而对有机下层膜进行图案转印,使用含卤气体按照该被图案转印了的有机下层膜进行基板加工。
在本发明中,该抗蚀剂下层膜作为硬掩模起作用,结构中的烷氧基、酰氧基、卤基等水解性基团水解或部分水解,然后通过硅烷醇基的缩合反应而形成聚硅氧烷结构的聚合物。该聚有机硅氧烷结构具有作为硬掩模的充分的功能。
而且,聚有机硅氧烷结构(中间膜)在其下所存在的有机下层膜的蚀刻、基板的加工(蚀刻)中作为硬掩模是有效的。即,对基板加工时、有机下层膜的氧系干蚀刻气体具有充分的耐干蚀刻性。
本发明中使用的硅烷化合物中的芳基三烷氧基硅烷的烷氧基芳基、卤代芳基能够在用EUV光使上层所存在的EUV抗蚀剂曝光时降低照射EUV的曝光量,即能够以低曝光量进行图案形成。
此外,本发明中使用的硅烷化合物中的水解性基团优选使用甲氧基。硅烷化合物水解,将其水解缩合物(聚硅氧烷)用于形成抗蚀剂下层膜的组合物,但有时不会完全水解,部分以硅烷醇基、烷氧基的状态存在。
该下层膜中的烷氧基有时在随后的处理工序中残留于膜中。在EUV曝光时有时该残留烷氧基、或其成分成为释气并附着于曝光机的镜等而成为曝光机的污染、故障的原因。本发明中,通过作为水解性基团使用以甲氧基作为主体的基团,而不是使用以乙氧基作为主体的基团,从而可以解决这些问题。
本发明涉及一种形成EUV光刻用抗蚀剂下层膜的组合物,其包含作为硅烷的水解性硅烷、其水解物、其水解缩合物、或它们的混合物,该水解性硅烷包含四甲氧基硅烷与烷基三甲氧基硅烷与芳基三烷氧基硅烷的组合,该芳基三烷氧基硅烷由上述式(1)表示。
本发明的形成抗蚀剂下层膜的组合物包含上述水解性硅烷、其水解物、其水解缩合物、或它们的混合物,还包含溶剂。而且作为任意成分,可以包含酸、水、醇、固化催化剂、产酸剂、其它有机聚合物、吸光性化合物和表面活性剂等。
本发明的形成抗蚀剂下层膜的组合物中的固体成分为例如0.1~50质量%,或0.1~30质量%,0.1~25质量%。这里所谓固体成分,为从形成抗蚀剂下层膜的组合物的全部成分中除去了溶剂成分后的成分。
水解性硅烷、其水解物和其水解缩合物在固体成分中所占的比例为20质量%以上,为例如50~100质量%,或60~100质量%,或70~99.5质量%。
式(1)中,R1表示由苯环或萘环构成的芳香族环、或者包含异氰脲酸结构的环,R2为芳香族环的氢原子的取代基,为卤原子或碳原子数1~10的烷氧基,X为碳原子数1~10的烷氧基、碳原子数2~10的酰氧基或卤基。n1为0或1的整数,n2为1~5的整数。n1为1的情况为将硅原子与芳香族环以亚甲基连接的情况,n1为0的情况为硅原子与芳香族环直接结合的情况。
式(1)的R2的卤原子为氟原子、氯原子、溴原子和碘原子。
式(1)的R2的烷氧基可举出碳原子数1~10的具有直链、支链、环状的烷基部分的烷氧基,可举出例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、1-甲基-正丁氧基、2-甲基-正丁氧基、3-甲基-正丁氧基、1,1-二甲基-正丙氧基、1,2-二甲基-正丙氧基、2,2-二甲基-正丙氧基、1-乙基-正丙氧基、正己氧基、1-甲基-正戊氧基、2-甲基-正戊氧基、3-甲基-正戊氧基、4-甲基-正戊氧基、1,1-二甲基-正丁氧基、1,2-二甲基-正丁氧基、1,3-二甲基-正丁氧基、2,2-二甲基-正丁氧基、2,3-二甲基-正丁氧基、3,3-二甲基-正丁氧基、1-乙基-正丁氧基、2-乙基-正丁氧基、1,1,2-三甲基-正丙氧基、1,2,2-三甲基-正丙氧基、1-乙基-1-甲基-正丙氧基和1-乙基-2-甲基-正丙氧基等,此外作为环状的烷氧基,可举出环丙氧基、环丁氧基、1-甲基-环丙氧基、2-甲基-环丙氧基、环戊氧基、1-甲基-环丁氧基、2-甲基-环丁氧基、3-甲基-环丁氧基、1,2-二甲基-环丙氧基、2,3-二甲基-环丙氧基、1-乙基-环丙氧基、2-乙基-环丙氧基、环己氧基、1-甲基-环戊氧基、2-甲基-环戊氧基、3-甲基-环戊氧基、1-乙基-环丁氧基、2-乙基-环丁氧基、3-乙基-环丁氧基、1,2-二甲基-环丁氧基、1,3-二甲基-环丁氧基、2,2-二甲基-环丁氧基、2,3-二甲基-环丁氧基、2,4-二甲基-环丁氧基、3,3-二甲基-环丁氧基、1-正丙基-环丙氧基、2-正丙基-环丙氧基、1-异丙基-环丙氧基、2-异丙基-环丙氧基、1,2,2-三甲基-环丙氧基、1,2,3-三甲基-环丙氧基、2,2,3-三甲基-环丙氧基、1-乙基-2-甲基-环丙氧基、2-乙基-1-甲基-环丙氧基、2-乙基-2-甲基-环丙氧基和2-乙基-3-甲基-环丙氧基等。
此外,式(1)的R2的烷氧基还包含烷氧基烷氧基。可举出例如甲氧基甲氧基、乙氧基乙氧基、甲氧基乙氧基、乙氧基甲氧基等。
式(1)的R2的烷氧基中,可以优选使用甲氧基、甲氧基甲氧基。
作为式(1)的X的碳原子数1~10的烷氧基,可举出碳原子数1~10的具有直链、支链、环状的烷基部分的烷氧基,可举出例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、1-甲基-正丁氧基、2-甲基-正丁氧基、3-甲基-正丁氧基、1,1-二甲基-正丙氧基、1,2-二甲基-正丙氧基、2,2-二甲基-正丙氧基、1-乙基-正丙氧基、正己氧基、1-甲基-正戊氧基、2-甲基-正戊氧基、3-甲基-正戊氧基、4-甲基-正戊氧基、1,1-二甲基-正丁氧基、1,2-二甲基-正丁氧基、1,3-二甲基-正丁氧基、2,2-二甲基-正丁氧基、2,3-二甲基-正丁氧基、3,3-二甲基-正丁氧基、1-乙基-正丁氧基、2-乙基-正丁氧基、1,1,2-三甲基-正丙氧基、1,2,2-三甲基-正丙氧基、1-乙基-1-甲基-正丙氧基和1-乙基-2-甲基-正丙氧基等,此外作为环状的烷氧基,可举出环丙氧基、环丁氧基、1-甲基-环丙氧基、2-甲基-环丙氧基、环戊氧基、1-甲基-环丁氧基、2-甲基-环丁氧基、3-甲基-环丁氧基、1,2-二甲基-环丙氧基、2,3-二甲基-环丙氧基、1-乙基-环丙氧基、2-乙基-环丙氧基、环己氧基、1-甲基-环戊氧基、2-甲基-环戊氧基、3-甲基-环戊氧基、1-乙基-环丁氧基、2-乙基-环丁氧基、3-乙基-环丁氧基、1,2-二甲基-环丁氧基、1,3-二甲基-环丁氧基、2,2-二甲基-环丁氧基、2,3-二甲基-环丁氧基、2,4-二甲基-环丁氧基、3,3-二甲基-环丁氧基、1-正丙基-环丙氧基、2-正丙基-环丙氧基、1-异丙基-环丙氧基、2-异丙基-环丙氧基、1,2,2-三甲基-环丙氧基、1,2,3-三甲基-环丙氧基、2,2,3-三甲基-环丙氧基、1-乙基-2-甲基-环丙氧基、2-乙基-1-甲基-环丙氧基、2-乙基-2-甲基-环丙氧基和2-乙基-3-甲基-环丙氧基等。
式(1)的X的碳原子数2~10的酰氧基可举出例如甲基羰氧基、乙基羰氧基、正丙基羰氧基、异丙基羰氧基、正丁基羰氧基、异丁基羰氧基、仲丁基羰氧基、叔丁基羰氧基、正戊基羰氧基、1-甲基-正丁基羰氧基、2-甲基-正丁基羰氧基、3-甲基-正丁基羰氧基、1,1-二甲基-正丙基羰氧基、1,2-二甲基-正丙基羰氧基、2,2-二甲基-正丙基羰氧基、1-乙基-正丙基羰氧基、正己基羰氧基、1-甲基-正戊基羰氧基、2-甲基-正戊基羰氧基、3-甲基-正戊基羰氧基、4-甲基-正戊基羰氧基、1,1-二甲基-正丁基羰氧基、1,2-二甲基-正丁基羰氧基、1,3-二甲基-正丁基羰氧基、2,2-二甲基-正丁基羰氧基、2,3-二甲基-正丁基羰氧基、3,3-二甲基-正丁基羰氧基、1-乙基-正丁基羰氧基、2-乙基-正丁基羰氧基、1,1,2-三甲基-正丙基羰氧基、1,2,2-三甲基-正丙基羰氧基、1-乙基-1-甲基-正丙基羰氧基、1-乙基-2-甲基-正丙基羰氧基、苯基羰氧基和甲苯磺酰基羰氧基等。
作为式(1)的X的卤基,可举出氟、氯、溴、碘等。
可以优选使用式(1)中R1为苯环的情况,R2为甲氧基、甲氧基甲氧基、氟原子、氯原子或溴原子的情况,X为甲氧基的情况,n1的整数为0的情况。
式(1)的水解性硅烷可以例如以下所例示。
上述烷基三甲氧基硅烷的烷基为具有直链或分支的碳原子数1~10的烷基,可举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、1-甲基-正丁基、2-甲基-正丁基、3-甲基-正丁基、1,1-二甲基-正丙基、1,2-二甲基-正丙基、2,2-二甲基-正丙基、1-乙基-正丙基、正己基、1-甲基-正戊基、2-甲基-正戊基、3-甲基-正戊基、4-甲基-正戊基、1,1-二甲基-正丁基、1,2-二甲基-正丁基、1,3-二甲基-正丁基、2,2-二甲基-正丁基、2,3-二甲基-正丁基、3,3-二甲基-正丁基、1-乙基-正丁基、2-乙基-正丁基、1,1,2-三甲基-正丙基、1,2,2-三甲基-正丙基、1-乙基-1-甲基-正丙基和1-乙基-2-甲基-正丙基等。此外还可以使用环状烷基,作为例如碳原子数1~10的环状烷基,可举出环丙基、环丁基、1-甲基-环丙基、2-甲基-环丙基、环戊基、1-甲基-环丁基、2-甲基-环丁基、3-甲基-环丁基、1,2-二甲基-环丙基、2,3-二甲基-环丙基、1-乙基-环丙基、2-乙基-环丙基、环己基、1-甲基-环戊基、2-甲基-环戊基、3-甲基-环戊基、1-乙基-环丁基、2-乙基-环丁基、3-乙基-环丁基、1,2-二甲基-环丁基、1,3-二甲基-环丁基、2,2-二甲基-环丁基、2,3-二甲基-环丁基、2,4-二甲基-环丁基、3,3-二甲基-环丁基、1-正丙基-环丙基、2-正丙基-环丙基、1-异丙基-环丙基、2-异丙基-环丙基、1,2,2-三甲基-环丙基、1,2,3-三甲基-环丙基、2,2,3-三甲基-环丙基、1-乙基-2-甲基-环丙基、2-乙基-1-甲基-环丙基、2-乙基-2-甲基-环丙基和2-乙基-3-甲基-环丙基等。
特别优选使用甲基,优选烷基三甲氧基硅烷为甲基三甲氧基硅烷的情况。
可以优选使用上述水解性硅烷以相对于四甲氧基硅烷70摩尔为10~35摩尔的比例包含烷基三甲氧基硅烷、为2~25摩尔的比例包含芳基三烷氧基硅烷的情况。
水解性硅烷的水解缩合物(聚有机硅烷)的具体例可以在以下进行例示。
水解性硅烷的水解缩合物(聚有机硅氧烷)可以获得重均分子量1000~1000000,或1000~100000的缩合物。它们的分子量为通过GPC分析,以聚苯乙烯换算得到的分子量。
GPC的测定条件例如可以如下进行:GPC装置(商品名HLC-8220GPC,东ソ一株式会社制),GPC柱(商品名ShodexKF803L,KF802,KF801,昭和电工制),柱温度使用40℃,洗脱液(洗脱溶剂)使用四氢呋喃,流量(流速)使用1.0ml/分钟,标准试样使用聚苯乙烯(昭和电工株式会社制)。
烷氧基甲硅烷基、酰氧基甲硅烷基或卤代甲硅烷基为水解性基团,该水解性基团水解时,使用每1摩尔水解性基团为0.5~100摩尔,优选为1~10摩尔的水。
此外,可以使用每1摩尔水解性基团为0.001~10摩尔,优选为0.001~1摩尔的水解催化剂。
进行水解和缩合时的反应温度通常为20~90℃。
水解可以进行完全水解,也可以进行部分水解。即,在水解缩合物中可以残存水解物、单体。
可以在水解缩合时使用催化剂。
作为水解催化剂,可举出金属螯合物、有机酸、无机酸、有机碱、无机碱。
作为水解催化剂的金属螯合物,可以举出例如三乙氧基·单(乙酰丙酮根)合钛、三-正丙氧基·单(乙酰丙酮根)合钛、三-异丙氧基·单(乙酰丙酮根)合钛、三-正丁氧基·单(乙酰丙酮根)合钛、三-仲丁氧基·单(乙酰丙酮根)合钛、三-叔丁氧基·单(乙酰丙酮根)合钛、二乙氧基·双(乙酰丙酮根)合钛、二-正丙氧基·双(乙酰丙酮根)合钛、二-异丙氧基·双(乙酰丙酮根)合钛、二-正丁氧基·双(乙酰丙酮根)合钛、二-仲丁氧基·双(乙酰丙酮根)合钛、二-叔丁氧基·双(乙酰丙酮根)合钛、单乙氧基·三(乙酰丙酮根)合钛、单正丙氧基·三(乙酰丙酮根)合钛、单异丙氧基·三(乙酰丙酮根)合钛、单正丁氧基·三(乙酰丙酮根)合钛、单仲丁氧基·三(乙酰丙酮根)合钛、单叔丁氧基·三(乙酰丙酮根)合钛、四(乙酰丙酮根)合钛、三乙氧基·单(乙酰乙酸乙酯)钛、三-正丙氧基·单(乙酰乙酸乙酯)钛、三-异丙氧基·单(乙酰乙酸乙酯)钛、三-正丁氧基·单(乙酰乙酸乙酯)钛、三-仲丁氧基·单(乙酰乙酸乙酯)钛、三-叔丁氧基·单(乙酰乙酸乙酯)钛、二乙氧基·双(乙酰乙酸乙酯)钛、二-正丙氧基·双(乙酰乙酸乙酯)钛、二-异丙氧基·双(乙酰乙酸乙酯)钛、二-正丁氧基·双(乙酰乙酸乙酯)钛、二-仲丁氧基·双(乙酰乙酸乙酯)钛、二-叔丁氧基·双(乙酰乙酸乙酯)钛、单乙氧基·三(乙酰乙酸乙酯)钛、单正丙氧基·三(乙酰乙酸乙酯)钛、单异丙氧基·三(乙酰乙酸乙酯)钛、单正丁氧基·三(乙酰乙酸乙酯)钛、单仲丁氧基·三(乙酰乙酸乙酯)钛、单叔丁氧基·三(乙酰乙酸乙酯)钛、四(乙酰乙酸乙酯)钛、单(乙酰丙酮根)三(乙酰乙酸乙酯)钛、双(乙酰丙酮根)双(乙酰乙酸乙酯)钛、三(乙酰丙酮根)单(乙酰乙酸乙酯)钛等钛螯合化合物;三乙氧基·单(乙酰丙酮根)合锆、三-正丙氧基·单(乙酰丙酮根)合锆、三-异丙氧基·单(乙酰丙酮根)合锆、三-正丁氧基·单(乙酰丙酮根)合锆、三-仲丁氧基·单(乙酰丙酮根)合锆、三-叔丁氧基·单(乙酰丙酮根)合锆、二乙氧基·双(乙酰丙酮根)合锆、二-正丙氧基·双(乙酰丙酮根)合锆、二-异丙氧基·双(乙酰丙酮根)合锆、二-正丁氧基·双(乙酰丙酮根)合锆、二-仲丁氧基·双(乙酰丙酮根)合锆、二-叔丁氧基·双(乙酰丙酮根)合锆、单乙氧基·三(乙酰丙酮根)合锆、单正丙氧基·三(乙酰丙酮根)合锆、单异丙氧基·三(乙酰丙酮根)合锆、单正丁氧基·三(乙酰丙酮根)合锆、单仲丁氧基·三(乙酰丙酮根)合锆、单叔丁氧基·三(乙酰丙酮根)合锆、四(乙酰丙酮根)合锆、三乙氧基·单(乙酰乙酸乙酯)锆、三-正丙氧基·单(乙酰乙酸乙酯)锆、三-异丙氧基·单(乙酰乙酸乙酯)锆、三-正丁氧基·单(乙酰乙酸乙酯)锆、三-仲丁氧基·单(乙酰乙酸乙酯)锆、三-叔丁氧基·单(乙酰乙酸乙酯)锆、二乙氧基·双(乙酰乙酸乙酯)锆、二-正丙氧基·双(乙酰乙酸乙酯)锆、二-异丙氧基·双(乙酰乙酸乙酯)锆、二-正丁氧基·双(乙酰乙酸乙酯)锆、二-仲丁氧基·双(乙酰乙酸乙酯)锆、二-叔丁氧基·双(乙酰乙酸乙酯)锆、单乙氧基·三(乙酰乙酸乙酯)锆、单正丙氧基·三(乙酰乙酸乙酯)锆、单异丙氧基·三(乙酰乙酸乙酯)锆、单正丁氧基·三(乙酰乙酸乙酯)锆、单仲丁氧基·三(乙酰乙酸乙酯)锆、单叔丁氧基·三(乙酰乙酸乙酯)锆、四(乙酰乙酸乙酯)锆、单(乙酰丙酮根)三(乙酰乙酸乙酯)锆、双(乙酰丙酮根)双(乙酰乙酸乙酯)锆、三(乙酰丙酮根)单(乙酰乙酸乙酯)锆等锆螯合化合物;三(乙酰丙酮根)合铝、三(乙酰乙酸乙酯)铝等铝螯合化合物;等。
作为水解催化剂的有机酸,可以举出例如乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、草酸、马来酸、甲基丙二酸、己二酸、癸二酸、没食子酸、丁酸、苯六甲酸、花生四烯酸、莽草酸、2-乙基己酸、油酸、硬脂酸、亚油酸、亚麻酸、水杨酸、苯甲酸、对氨基苯甲酸、对甲苯磺酸、苯磺酸、单氯乙酸、二氯乙酸、三氯乙酸、三氟乙酸、甲酸、丙二酸、磺酸、邻苯二甲酸、富马酸、柠檬酸、酒石酸等。
作为水解催化剂的无机酸,可以举出例如盐酸、硝酸、硫酸、氢氟酸、磷酸等。
作为水解催化剂的有机碱,可以举出例如吡啶、吡咯、哌嗪、吡咯烷、哌啶、皮考啉、三甲胺、三乙胺、单乙醇胺、二乙醇胺、二甲基单乙醇胺、单甲基二乙醇胺、三乙醇胺、二氮杂二环辛烷、二氮杂二环壬烷、二氮杂二环十一碳烯、四甲基氢氧化铵等。作为无机碱,可以举出例如氨、氢氧化钠、氢氧化钾、氢氧化钡、氢氧化钙等。这些催化剂中,优选为金属螯合物、有机酸、无机酸,它们可以同时使用1种或者2种以上。
作为水解中使用的有机溶剂,可以举出例如正戊烷、异戊烷、正己烷、异己烷、正庚烷、异庚烷、2,2,4-三甲基戊烷、正辛烷、异辛烷、环己烷、甲基环己烷等脂肪族烃系溶剂;苯、甲苯、二甲苯、乙苯、三甲基苯、甲基乙基苯、正丙基苯、异丙基苯、二乙基苯、异丁基苯、三乙基苯、二异丙基苯、正戊基萘等芳香族烃系溶剂;甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、正戊醇、异戊醇、2-甲基丁醇、仲戊醇、叔戊醇、3-甲氧基丁醇、正己醇、2-甲基戊醇、仲己醇、2-乙基丁醇、仲庚醇、庚醇-3、正辛醇、2-乙基己醇、仲辛醇、正壬醇、2,6-二甲基庚醇-4、正癸醇、仲十一烷醇、三甲基壬醇、仲十四烷醇、仲十七烷醇、苯酚、环己醇、甲基环己醇、3,3,5-三甲基环己醇、苄基醇、苯基甲基甲醇、双丙酮醇、甲酚等一元醇系溶剂;乙二醇、丙二醇、1,3-丁二醇、戊二醇-2,4、2-甲基戊二醇-2,4、己二醇-2,5、庚二醇-2,4、2-乙基己二醇-1,3、二甘醇、双丙甘醇、三甘醇、三丙二醇、甘油等多元醇系溶剂;丙酮、甲基乙基酮、甲基-正丙基酮、甲基-正丁基酮、二乙基酮、甲基异丁基酮、甲基-正戊基酮、乙基-正丁基酮、甲基-正己基酮、二异丁基酮、三甲基壬酮、环己酮、甲基环己酮、2,4-戊烷二酮、丙酮基丙酮、双丙酮醇、苯乙酮、葑酮等酮系溶剂;乙醚、异丙基醚、正丁基醚、正己基醚、2-乙基己基醚、环氧乙烷、1,2-环氧丙烷、二氧戊环、4-甲基二氧戊环、二烷、二甲基二烷、乙二醇单甲基醚、乙二醇单乙基醚、乙二醇二乙基醚、乙二醇单正丁基醚、乙二醇单正己基醚、乙二醇单苯基醚、乙二醇单-2-乙基丁基醚、乙二醇二丁基醚、二甘醇单甲基醚、二甘醇单乙基醚、二甘醇二乙基醚、二甘醇单正丁基醚、二甘醇二-正丁基醚、二甘醇单正己基醚、乙氧基三甘醇、四甘醇二-正丁基醚、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单丙基醚、丙二醇单丁基醚、双丙甘醇单甲基醚、双丙甘醇单乙基醚、双丙甘醇单丙基醚、双丙甘醇单丁基醚、三丙二醇单甲基醚、四氢呋喃、2-甲基四氢呋喃等醚系溶剂;碳酸二乙酯、乙酸甲酯、乙酸乙酯、γ-丁内酯、γ-戊内酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯、乙酸异丁酯、乙酸仲丁酯、乙酸正戊酯、乙酸仲戊酯、乙酸3-甲氧基丁酯、乙酸甲基戊酯、乙酸2-乙基丁酯、乙酸2-乙基己酯、乙酸苄酯、乙酸环己酯、乙酸甲基环己酯、乙酸正壬酯、乙酰乙酸甲酯、乙酰乙酸乙酯、乙酸乙二醇单甲基醚、乙酸乙二醇单乙基醚、乙酸二甘醇单甲基醚、乙酸二甘醇单乙基醚、乙酸二甘醇单正丁基醚、乙酸丙二醇单甲基醚、乙酸丙二醇单乙基醚、乙酸丙二醇单丙基醚、乙酸丙二醇单丁基醚、乙酸双丙甘醇单甲基醚、乙酸双丙甘醇单乙基醚、二乙酸乙二醇酯、乙酸甲氧基三甘醇酯、丙酸乙酯、丙酸正丁酯、丙酸异戊酯、草酸二乙酯、草酸二-正丁酯、乳酸甲酯、乳酸乙酯、乳酸正丁酯、乳酸正戊酯、丙二酸二乙酯、邻苯二甲酸二甲酯、邻苯二甲酸二乙酯等酯系溶剂;N-甲基甲酰胺、N,N-二甲基甲酰胺、N,N-二乙基甲酰胺、乙酰胺、N-甲基乙酰胺、N,N-二甲基乙酰胺、N-甲基丙酰胺、N-甲基吡咯烷酮等含氮系溶剂;甲硫醚、乙硫醚、噻吩、四氢噻吩、二甲亚砜、环丁砜、1,3-丙烷磺内酯等含硫系溶剂等。这些溶剂可以使用1种或2种以上的组合。
从溶液的保存稳定性方面考虑,特别优选为丙酮、甲基乙基酮、甲基-正丙基酮、甲基-正丁基酮、二乙基酮、甲基-异丁基酮、甲基-正戊基酮、乙基-正丁基酮、甲基-正己基酮、二-异丁基酮、三甲基壬酮、环己酮、甲基环己酮、2,4-戊烷二酮、丙酮基丙酮、双丙酮醇、苯乙酮、葑酮(1,1,3-三甲基-2-降冰片烯)等酮系溶剂。
在溶剂中使用催化剂将水解性有机硅烷进行水解缩合,所得的水解缩合物(聚合物)可以通过减压蒸馏等同时除去副生成物的醇、所使用的水解催化剂、水。另外,水解中使用的酸、碱催化剂可以通过中和、离子交换而除去。而且对于本发明的形成光刻用抗蚀剂下层膜的组合物,含有其水解缩合物的形成抗蚀剂下层膜的组合物为了稳定化可以添加酸(例如有机酸)、水、醇、或它们的组合。
作为上述有机酸,可以举出例如草酸、丙二酸、甲基丙二酸、琥珀酸、马来酸、苹果酸、酒石酸、邻苯二甲酸、柠檬酸、戊二酸、柠檬酸、乳酸、水杨酸等。其中,优选为草酸、马来酸等。加入的有机酸相对于缩合物(聚有机硅氧烷)100质量份为0.5~5.0质量份。另外,加入的水可以使用纯水、超纯水、离子交换水等,其添加量相对于形成抗蚀剂下层膜的组合物100质量份可以为1~20质量份。
另外,作为加入的醇,优选为通过涂布后的加热容易飞散的醇,可以举出例如甲醇、乙醇、丙醇、异丙醇、丁醇等。加入的醇相对于形成抗蚀剂下层膜的组合物100质量份可以为1~20质量份。
在本发明中,可以含有交联性化合物。作为这些交联剂,优选使用具有至少二个交联形成取代基的交联性化合物。可举出例如,具有羟甲基、甲氧基甲基这样的交联形成取代基的三聚氰胺系化合物、取代脲系化合物。具体而言,为甲氧基甲基化甘脲或甲氧基甲基化三聚氰胺等化合物,例如为四甲氧基甲基甘脲、四丁氧基甲基甘脲或六甲氧基甲基三聚氰胺。此外,还可举出四甲氧基甲基脲、四丁氧基甲基脲等化合物。在包含这些交联剂的情况下,在固体成分中例如为50质量%以下,为0.01~50质量%,或为10~40质量%。
本发明的形成抗蚀剂下层膜的组合物可以包含酸化合物。作为酸化合物,可举出例如,对甲苯磺酸、三氟甲磺酸和吡啶-对-甲苯磺酸盐等磺酸化合物、水杨酸、磺基水杨酸、柠檬酸、苯甲酸和羟基苯甲酸等羧酸化合物。此外,作为酸化合物,可举出例如,2,4,4,6-四溴环己二烯酮、苯偶姻甲苯磺酸酯、2-硝基苄基甲苯磺酸酯、对-三氟甲基苯磺酸-2,4-二硝基苄基酯、苯基-双(三氯甲基)-均-三嗪和N-羟基琥珀酰亚胺三氟甲烷磺酸酯等通过热或光而产生酸的产酸剂。作为酸化合物,此外,可举出二苯基碘六氟磷酸盐、二苯基碘三氟甲烷磺酸盐和双(4-叔丁基苯基)碘三氟甲烷磺酸盐等碘盐系产酸剂、和三苯基锍六氟锑酸盐、和三苯基锍三氟甲烷磺酸盐等锍盐系产酸剂。作为酸化合物,优选使用磺酸化合物、碘盐系产酸剂、锍盐系产酸剂。酸化合物可以仅使用一种,此外可以二种以上组合使用。酸化合物的含量在固体成分中例如为0.1~10质量%,或为0.1~5质量%。
本发明的形成抗蚀剂下层膜的组合物可以含有固化催化剂。固化催化剂在将含有由水解缩合物形成的聚有机硅氧烷的涂布膜进行加热使其固化时发挥固化催化剂的作用。
还可以使用铵化合物、环状铵化合物、环状胺化合物或化合物。
作为上述化合物,为盐,可以使用例如锍盐。作为锍盐,可举出例如
所示的锍离子与
所示的阴离子的盐。
固化催化剂相对于聚有机硅氧烷100质量份为0.01~10质量份、或0.01~5质量份、或0.01~3质量份。此外,包含烃基的磺酸根离子、氯离子、硝酸根离子、马来酸根离子与离子的盐相对于聚有机硅氧烷100质量份为0.1~10质量%,或为0.1~5质量%、或0.1~3质量%。
作为流变调节剂,可举出例如,邻苯二甲酸二甲酯、邻苯二甲酸二乙酯、邻苯二甲酸二异丁酯、邻苯二甲酸二己酯、丁基异癸基邻苯二甲酸酯等邻苯二甲酸化合物、己二酸二正丁酯、己二酸二异丁酯、己二酸二异辛酯、辛基癸基己二酸酯等己二酸化合物、马来酸二正丁酯、马来酸二乙酯、马来酸二壬酯等马来酸化合物、油酸甲酯、油酸丁酯、油酸四氢糠酯等油酸化合物、和硬脂酸正丁酯、硬脂酸甘油酯等硬脂酸化合物。在使用流变调节剂的情况下,作为其使用量,在固体成分中例如为0.001~10质量%。
作为表面活性剂,可举出例如,聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯鲸蜡基醚、聚氧乙烯油基醚等聚氧乙烯烷基醚类、聚氧乙烯辛基苯酚醚、聚氧乙烯壬基苯酚醚等聚氧乙烯烷基芳基醚类、聚氧乙烯-聚氧丙烯嵌段共聚物类、失水山梨糖醇单月桂酸酯、失水山梨糖醇单棕榈酸酯、失水山梨糖醇单硬脂酸酯、失水山梨糖醇单油酸酯、失水山梨糖醇三油酸酯、失水山梨糖醇三硬脂酸酯等失水山梨糖醇脂肪酸酯类、聚氧乙烯失水山梨糖醇单月桂酸酯、聚氧乙烯失水山梨糖醇单棕榈酸酯、聚氧乙烯失水山梨糖醇单硬脂酸酯、聚氧乙烯失水山梨糖醇三油酸酯、聚氧乙烯失水山梨糖醇三硬脂酸酯等聚氧乙烯失水山梨糖醇脂肪酸酯类等非离子系表面活性剂、商品名エフトップEF301、EF303、EF352((株)トーケムプロダクツ制)、商品名メガファックF171、F173、R-08、R-30(大日本インキ化学工业(株)制)、フロラードFC430、FC431(住友スリーエム(株)制)、商品名アサヒガードAG710、サーフロンS-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(株)制)等氟系表面活性剂、和有机硅氧烷聚合物KP341(信越化学工业(株)制)等。这些表面活性剂可以单独使用,此外也可以2种以上组合使用。在使用表面活性剂的情况下,作为其使用量,在固体成分中例如为0.0001~5质量%。
作为本发明的形成抗蚀剂下层膜的组合物中使用的溶剂,只要为可以溶解上述固体成分的溶剂,就可以没有特别限制地使用。作为这样的溶剂,可举出例如,乙二醇单甲基醚、乙二醇单乙基醚、甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯、二甘醇单甲基醚、二甘醇单乙基醚、丙二醇、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单甲基醚乙酸酯、丙二醇丙基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、环戊酮、环己酮、2-羟基丙酸乙酯、2-羟基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羟基乙酸乙酯、2-羟基-3-甲基丁酸甲酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯、丙酮酸甲酯、丙酮酸乙酯、乙酸乙酯、乙酸丁酯、乳酸乙酯和乳酸丁酯等。这些溶剂可以单独使用,或二种以上组合使用。此外,可以将丙二醇单丁基醚、丙二醇单丁基醚乙酸酯等高沸点溶剂混合来使用。
在半导体基板(例如,硅/二氧化硅被覆基板、氮化硅基板、玻璃基板和ITO基板等)上,通过旋涂器、涂布机等适当的涂布方法涂布本发明的形成抗蚀剂下层膜的组合物,然后,进行烘烤,从而形成抗蚀剂下层膜。
作为进行烘烤的条件,从烘烤温度80℃~250℃,烘烤时间0.3~60分钟中进行适宜选择。优选为烘烤温度130℃~250℃,烘烤时间0.5~5分钟。这里,作为所形成的抗蚀剂下层膜的膜厚,例如为0.01~3.0μm,优选为例如0.01~1.0μm,或为0.01~0.5μm,或为0.01~0.05μm。
接着,在抗蚀剂下层膜上,形成EUV抗蚀剂等高能量射线抗蚀剂的层。高能量射线抗蚀剂的层的形成可以通过周知的方法,即,通过高能量射线抗蚀剂组合物溶液在下层膜上的涂布和烘烤来进行。
作为EUV抗蚀剂,可以采用例如使用了PMMA(聚甲基丙烯酸甲酯)、聚羟基苯乙烯、酚树脂等树脂的抗蚀剂组合物。
接下来,通过规定的掩模来进行曝光。曝光时,可以使用EUV光(13.5nm)、电子射线、X射线等。曝光后,还可以根据需要进行曝光后加热(PEB:Post Exposure Bake)。曝光后加热从加热温度70℃~150℃,加热时间0.3~10分钟进行适宜选择。
接着,通过显影液进行显影。作为显影液,作为例子可举出氢氧化钾、氢氧化钠等碱金属氢氧化物的水溶液、氢氧化四甲铵、氢氧化四乙铵、胆碱等氢氧化季铵的水溶液、乙醇胺、丙基胺、乙二胺等胺水溶液等碱性水溶液。此外,还可以在这些显影液中添加表面活性剂等。作为显影的条件,从温度5~50℃,时间10~300秒进行适宜选择。
而且,将这样所形成的光致抗蚀剂的图案作为保护膜,进行抗蚀剂下层膜的除去和半导体基板的加工。抗蚀剂下层膜的除去使用四氟甲烷、全氟环丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷、一氧化碳、氩气、氧气、氮气、六氟化硫、二氟甲烷、三氟化氮和三氟化氯等气体来进行。
还可以在半导体基板上形成本发明的抗蚀剂下层膜之前,形成平坦化膜、间隙填充材层、有机下层膜。在使用具有大的阶梯差、孔穴的半导体基板的情况下,优选形成了平坦化膜、间隙填充材层。
实施例
合成例1
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、(4-甲氧基苯基)三甲氧基硅烷1.62g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-1),聚硅氧烷中来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于(4-甲氧基苯基)三甲氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
合成例2
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、(4-甲氧基苄基)三甲氧基硅烷1.97g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-2),聚硅氧烷中来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于(4-甲氧基苄基)三甲氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
合成例3
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、[4-(甲氧基甲氧基)苯基]三甲氧基硅烷1.82g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-3),聚硅氧烷中来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于[4-(甲氧基甲氧基)苯基]三甲氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
合成例4
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、{2-[6-(甲氧基甲氧基)萘基]}三甲氧基硅烷2.19g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-4),聚硅氧烷中来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于{2-[6-(甲氧基甲氧基)萘基]}三甲氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
合成例5
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、五氟苯基三乙氧基硅烷2.03g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、乙醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-5),聚硅氧烷中来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于五氟苯基三乙氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
合成例6
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、(4-氯苯基)三乙氧基硅烷1.62g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、乙醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-6),聚硅氧烷中来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于(4-氯苯基)三乙氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
合成例7
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、(4-溴苯基)三甲氧基硅烷1.75g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-7),聚硅氧烷中来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于(4-溴苯基)三甲氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
合成例8
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、(4-甲氧基苯基)三甲氧基硅烷3.24g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-1),聚硅氧烷中的来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于(4-甲氧基苯基)三甲氧基硅烷的单元结构的摩尔比为70:25:15。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
合成例9
将四甲氧基硅烷7.5g、甲基三甲氧基硅烷1.5g、(4-甲氧基苯基)三甲氧基硅烷2.5g、丙酮19.5g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸2.7g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯26g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-1),聚硅氧烷中的来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于(4-甲氧基苯基)三甲氧基硅烷的单元结构的摩尔比为70:20:10。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为1500。
合成例10
将四甲氧基硅烷7.5g、甲基三甲氧基硅烷1.5g、五氟苯基三乙氧基硅烷2.5g、丙酮19.5g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸2.7g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯26g,将作为反应副产物的甲醇、乙醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(2-5),聚硅氧烷中来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于五氟苯基三乙氧基硅烷的单元结构的摩尔比为70:20:10。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为1500。
比较合成例1
将四甲氧基硅烷18.60g、甲基三甲氧基硅烷3.48g、苯基三甲氧基硅烷1.41g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(3-1),聚硅氧烷中的来源于四甲氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于苯基三甲氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为2000。
比较合成例2
将四乙氧基硅烷7.5g、甲基三甲氧基硅烷1.5g、苯基三甲氧基硅烷1.2g、丙酮35.55g加入至300ml的烧瓶中,一边利用电磁搅拌器搅拌混合溶液,一边将0.01mol/l的盐酸5.21g滴加至混合溶液中。添加后,将烧瓶移至调整为85℃的油浴中,在加温回流下反应240分钟。然后,将反应溶液冷却至室温,在反应溶液中添加丙二醇单甲基醚乙酸酯48.00g,将作为反应副产物的甲醇、丙酮、水、盐酸减压蒸馏除去,进行浓缩而获得水解缩合物(聚合物)丙二醇单甲基醚乙酸酯溶液。添加丙二醇单乙基醚,进行调整以使丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率为以140℃时的固体残留物换算计为20质量%。获得的聚合物相当于式(3-1),聚硅氧烷中的来源于四乙氧基硅烷的单元结构、来源于甲基三甲氧基硅烷的单元结构、来源于苯基三甲氧基硅烷的单元结构的摩尔比为70:25:5。通过GPC得到的重均分子量以聚苯乙烯换算计Mw为1500。
(有机下层膜(A层))
使用丸善石油化学株式会社制的CNp-PM(成分中,摩尔比为乙烯基萘60%:聚羟基苯乙烯40%,重均分子量:6000)作为有机下层膜(A层)。
以下,将通过本发明的薄膜形成组合物得到的薄膜作为抗蚀剂下层膜使用的情况下的评价结果示于以下。
将由合成例1~10、比较合成例1~2调制的聚合物溶液调整至固体成分20质量%,分别制成实施例1~10和比较例1~2的形成抗蚀剂下层膜的组合物。
(抗蚀剂下层膜的调整)
将由上述合成例1~10和比较合成例1~2获得的含有硅的聚合物、酸、固化催化剂、添加剂、溶剂、水以成为表1所示的比例的方式进行混合,用0.1μm的氟树脂制的过滤器进行过滤,从而分别调制出抗蚀剂下层膜形成用组合物的溶液。表1中的聚合物的添加比例不是表示聚合物溶液的添加量,而是表示聚合物本身的添加量。
在表1中,马来酸缩写为MA,苄基三乙基氯化铵缩写为BTAC,N-(3-三乙氧基甲硅烷基丙基)-4,5-二氢咪唑缩写为IMIDTEOS,双(4-羟基苯基)砜缩写为BPS,丙二醇单甲基醚乙酸酯缩写为PGMEA,丙二醇单乙基醚缩写为PGEE,丙二醇单甲基醚缩写为PGME,乳酸乙酯缩写为EL。水使用超纯水。各添加量以质量份表示。
[表1]
表1
将所调制的抗蚀剂下层膜形成用组合物的溶液用于光学常数的测定,将稀释至以固体成分计为1质量%的稀释液用于通过EUV曝光进行的抗蚀剂图案的形成、释气测定。
(光学常数测定)
使用旋涂器在硅片上分别涂布上述形成抗蚀剂下层膜的组合物。在电热板上在215℃加热1分钟,形成抗蚀剂下层膜(膜厚0.05μm)。然后,对于这些抗蚀剂下层膜,使用光谱椭偏仪(J.A.Woollam社制,VUV-VASEVU-302),测定在波长193、248nm的折射率(n值)和光学吸光系数(k值,也被称为衰减系数)。
[表2]
表2
〔通过EUV曝光进行的抗蚀剂图案的形成〕
将上述形成有机下层膜(A层)的组合物涂布在硅片上,在电热板上在215℃烘烤60秒,获得膜厚90nm的有机下层膜(A层)。在其上旋转涂布由本发明的实施例1~8、比较例1调制的形成抗蚀剂下层膜的组合物溶液,在215℃加热1分钟,从而形成抗蚀剂下层膜(B)层(25nm)。在该(B)层上,将EUV用抗蚀剂溶液(甲基丙烯酸酯树脂系抗蚀剂)进行旋转涂布,进行加热,形成EUV抗蚀剂层(C)层,使用EUV曝光装置(Micro Exposure Tool,简称MET),在NA=0.30,σ=0.36/0.68,Quadropole的条件下进行曝光。曝光后,进行PEB(曝光后加热,90℃),在冷却板上冷却至室温,进行显影和冲洗处理,形成抗蚀剂图案。评价是评价通过26nm的线与间隙的形成可否、由图案截面观察得到的图案形状。
[表3]
表3
〔释气产生量试验〕
使用旋涂器将由实施例9和10、比较例2调整的形成抗蚀剂下层膜的组合物溶液涂布在硅片上。在电热板上在205℃加热1分钟,形成抗蚀剂下层膜(膜厚0.03μm)。
使用这些抗蚀剂下层膜,采用Resist Outgassing Exposure(ROX)系统进行释气测定。利用Quadropole MS测定在腔室内压力为1.0~8.0×10-8的范围以曝光量6.0mJ/cm2进行EUV曝光而产生的释气量。释气为在分子量44除外的35~200的范围进行测定。
将释气产生量的结果记载于表4中。
单位为(分子数/cm2/s)。
[表4]
表4
采用使用作为水解性基团仅包含甲氧基的硅烷化合物而得的合成例9和10的实施例9和10,与采用使用大量包含乙氧基作为水解性基团的四乙氧基硅烷的硅烷化合物而得的比较合成例2的比较例2相比,释气的产生量少。
在实施例9中,在全部硅烷中,硅烷的水解性基团是甲氧基:乙氧基的摩尔比为100:0。
在实施例10中,在全部硅烷中,硅烷的水解性基团是甲氧基:乙氧基的摩尔比为34:3。
在比较例2中,在全部硅烷中,硅烷的水解性基团是甲氧基:乙氧基的摩尔比为28:9。
在本发明中可知,在全部硅烷中,硅烷的水解性基团在以甲氧基:乙氧基的摩尔比计为100:0~80:20的范围进行使用,从而释气的发生少。
产业可利用性
根据本发明,可以提供能够利用矩形的抗蚀剂图案进行微细的基板加工,可以用于制造半导体装置的形成EUV光刻用抗蚀剂下层膜的组合物。能够提供EUV抗蚀剂的曝光灵敏度提高,不发生与抗蚀剂的混合,与抗蚀剂相比具有大的干蚀刻速度,用EUV光曝光时释气发生少的光刻用抗蚀剂下层膜。
Claims (14)
1.一种形成EUV光刻用抗蚀剂下层膜的组合物,其包含作为硅烷的水解性硅烷、其水解物、其水解缩合物、或它们的混合物,该水解性硅烷包含四甲氧基硅烷与烷基三甲氧基硅烷与芳基三烷氧基硅烷的组合,该芳基三烷氧基硅烷由下述式(1)表示,
(R2)n2-R1-(CH2)n1-Si(X)3 式(1)
式(1)中,R1表示由苯环或萘环构成的芳香族环、或者包含异氰脲酸结构的环,在R1为由苯环或萘环构成的芳香族环的情况下,R2为芳香族环内的氢原子的取代基,为卤原子或碳原子数1~10的烷氧基,在R1为包含异氰脲酸结构的环的情况下,R2为烯丙基;X为碳原子数1~10的烷氧基、碳原子数2~10的酰氧基或卤基,n1为0或1的整数,在苯环的情况下,n2为1~5的整数,在萘环的情况下,n2为1~9的整数,
所述硅烷,在全部硅烷中以摩尔比计为甲氧基:乙氧基=100:0~80:20的比例含有甲氧基和乙氧基作为水解性基团。
2.根据权利要求1所述的形成EUV光刻用抗蚀剂下层膜的组合物,式(1)的R1为苯环。
3.根据权利要求1或2所述的形成EUV光刻用抗蚀剂下层膜的组合物,式(1)的R2为甲氧基、甲氧基甲氧基、氟原子、氯原子或溴原子。
4.根据权利要求1或2所述的形成EUV光刻用抗蚀剂下层膜的组合物,式(1)的X为甲氧基。
5.根据权利要求1或2所述的形成EUV光刻用抗蚀剂下层膜的组合物,式(1)的n1为0。
6.根据权利要求1或2所述的形成EUV光刻用抗蚀剂下层膜的组合物,烷基三甲氧基硅烷为甲基三甲氧基硅烷。
7.根据权利要求1或2所述的形成EUV光刻用抗蚀剂下层膜的组合物,水解性硅烷以相对于四甲氧基硅烷70摩尔为10~35摩尔的比例包含烷基三甲氧基硅烷、为2~25摩尔的比例包含芳基三烷氧基硅烷。
8.根据权利要求1或2所述的形成EUV光刻用抗蚀剂下层膜的组合物,其还包含酸。
9.根据权利要求1或2所述的形成EUV光刻用抗蚀剂下层膜的组合物,其还包含水。
10.根据权利要求1或2所述的形成EUV光刻用抗蚀剂下层膜的组合物,其还包含铵化合物、环状胺化合物或化合物。
11.根据权利要求10所述的形成EUV光刻用抗蚀剂下层膜的组合物,所述铵化合物为环状铵化合物。
12.一种抗蚀剂下层膜,其为通过将权利要求1~11的任一项所述的形成EUV光刻用抗蚀剂下层膜的组合物涂布在半导体基板上,进行烘烤而获得的。
13.一种半导体装置的制造方法,其包括下述工序:将权利要求1~11的任一项所述的形成EUV光刻用抗蚀剂下层膜的组合物涂布在半导体基板上,进行烘烤,形成抗蚀剂下层膜的工序;在所述抗蚀剂下层膜上涂布抗蚀剂用组合物,形成抗蚀剂膜的工序;将所述抗蚀剂膜进行曝光的工序;在曝光后将所述抗蚀剂膜进行显影,获得抗蚀剂图案的工序;按照所述抗蚀剂图案对所述抗蚀剂下层膜进行蚀刻的工序;和按照被图案化了的所述抗蚀剂膜和所述抗蚀剂下层膜对所述半导体基板进行加工的工序。
14.一种半导体装置的制造方法,其包括下述工序:在半导体基板上形成有机下层膜的工序;在该有机下层膜上涂布权利要求1~11的任一项所述的形成EUV光刻用抗蚀剂下层膜的组合物,进行烘烤,形成抗蚀剂下层膜的工序;在所述抗蚀剂下层膜上涂布抗蚀剂用组合物,形成抗蚀剂膜的工序;将所述抗蚀剂膜进行曝光的工序;在曝光后将所述抗蚀剂膜进行显影,获得抗蚀剂图案的工序;按照所述抗蚀剂图案对所述抗蚀剂下层膜进行蚀刻的工序;按照被图案化了的所述抗蚀剂下层膜对所述有机下层膜进行蚀刻的工序;和按照被图案化了的所述有机下层膜对所述半导体基板进行加工的工序。
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