TW202144513A - 膜形成用組成物 - Google Patents
膜形成用組成物 Download PDFInfo
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- TW202144513A TW202144513A TW110111933A TW110111933A TW202144513A TW 202144513 A TW202144513 A TW 202144513A TW 110111933 A TW110111933 A TW 110111933A TW 110111933 A TW110111933 A TW 110111933A TW 202144513 A TW202144513 A TW 202144513A
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 116
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- 239000002904 solvent Substances 0.000 claims abstract description 52
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 51
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 48
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000001459 lithography Methods 0.000 claims abstract description 39
- 125000000962 organic group Chemical group 0.000 claims abstract description 34
- 125000005843 halogen group Chemical group 0.000 claims abstract description 32
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 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
- XFSPFPFUBRZQFO-UHFFFAOYSA-N trifluoromethyl dihydrogen phosphate Chemical compound OP(O)(=O)OC(F)(F)F XFSPFPFUBRZQFO-UHFFFAOYSA-N 0.000 description 1
- RVEFQCRHIJJPQZ-UHFFFAOYSA-N triiodomethanesulfonic acid Chemical compound OS(=O)(=O)C(I)(I)I RVEFQCRHIJJPQZ-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-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
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- ZOWVSEMGATXETK-UHFFFAOYSA-N trimethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OC)(OC)OC)CCC2OC21 ZOWVSEMGATXETK-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
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
- RIDBNXZGOXZXEV-UHFFFAOYSA-N triphenylmethanesulfonic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S(=O)(=O)O)C1=CC=CC=C1 RIDBNXZGOXZXEV-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- SLVHCWLFRYIBQT-UHFFFAOYSA-N tris(trichloromethyl) phosphate Chemical compound ClC(Cl)(Cl)OP(=O)(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl SLVHCWLFRYIBQT-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- SJEYEFOHSMBQIX-UHFFFAOYSA-N undecane-1-sulfonic acid Chemical compound CCCCCCCCCCCS(O)(=O)=O SJEYEFOHSMBQIX-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical group CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
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- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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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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- 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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/42—Sulfonic acids; Derivatives thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/541—Silicon-containing compounds containing oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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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- G03F7/26—Processing photosensitive materials; Apparatus therefor
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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
- 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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- H01L21/0271—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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- H01L21/04—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
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- H01L21/3086—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane characterised by the process involved to create the mask, e.g. lift-off masks, sidewalls, or to modify the mask, e.g. pre-treatment, post-treatment
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Abstract
本發明係提供一種提供膜之組成物,該膜,可作為具有對形成為上層之光阻膜用組成物之溶劑的耐性、對氟系氣體之良好蝕刻特性、以及良好微影特性之光阻下層膜而良好地發揮功能。
本發明之膜形成用組成物,係含有使用二種以上酸性化合物進行水解性矽烷化合物之水解及縮合而獲得之水解縮合物、及溶劑;其特徵係
上述水解性矽烷化合物,含有下述式(1)所表示之含胺基之矽烷:
(式(1)中,R1
係與矽原子鍵結之基團,互相獨立地表示含有胺基之有機基;
R2
係與矽原子鍵結之基團,表示可經取代之烷基、可經取代之芳基、可經取代之芳烷基、可經取代之鹵化烷基、可經取代之鹵化芳基、可經取代之鹵化芳烷基、可經取代之烷氧烷基、可經取代之烷氧芳基、可經取代之烷氧芳烷基、或可經取代之烯基,或者表示含有環氧基、丙烯醯基、甲基丙烯醯基、巰基或氰基之有機基;
R3
係與矽原子鍵結之基團或原子,互相獨立地表示烷氧基、芳烷氧基、醯氧基或鹵原子;
a係1~2之整數,b係0~1之整數,並滿足a+b≦2。)。
Description
關於膜形成用組成物。
歷來在半導體裝置之製造中,進行使用光阻劑之微影之微細加工。上述微細加工係藉由在矽晶圓等半導體基板上形成光阻劑材料之薄膜,於其上經由描繪有半導體元件圖案之光罩圖案照射紫外線等活性光線,顯影,並將獲得之光阻劑膜之圖案作為保護膜對基板進行蝕刻處理,從而在基板表面形成與上述圖案對應之微細凹凸之加工法。
近年,在半導體最尖端之裝置中,光阻膜之薄膜化顯著,其中特別在由光阻膜、含矽之光阻下層膜、有機下層膜所成之三層製程中,對於為光阻下層膜之Si-HM(Silicon-Hard Mask:矽-硬光罩),除了良好之微影特性,亦要求濕蝕刻中良好的蝕刻速率,因此,需有對濕蝕刻藥液(HF等)之良好的溶解性。
根據此種要求,特別是在EUV(Extreme Ultraviolet:極紫外線)微影中,以提升微影特性為目的,已進行對大量導入於與光阻密著性高之官能基之聚合物中、及大量添加於光酸產生劑之組成物中之材料之開發,但在此種材料中,有機成分之增加造成對濕蝕刻藥液(HF等)之溶解性降低成為一大問題。
在此種情況下,已揭露一種含有具有鎓基之矽烷化合物之光阻下層膜形成用組成物、及一種含有具有陰離子基之矽烷化合物之光阻下層膜(專利文獻1及專利文獻2)。
[先前技術文獻]
[專利文獻]
[專利文獻1]國際公開第2010/021290號
[專利文獻2]國際公開第2010/071155號
[發明所欲解決之技術問題]
本發明,係鑑於上述情況所成者,目的係提供一種提供膜之組成物,該膜,可作為具有對形成為上層之光阻膜用組成物之溶劑的耐性、對氟系氣體之良好蝕刻特性、以及良好微影特性之光阻下層膜而良好地發揮功能。
[技術手段]
本發明人等,為了解決上述課題反覆深入研究之結果,發現含有使用二種以上酸性化合物將含有指定水解性矽烷之水解性矽烷化合物水解及縮合而獲得之水解縮合物、及溶劑之組成物能夠提供膜,該膜,可作為具有對形成為上層之光阻膜用組成物之溶劑的耐性、對氟系氣體之良好蝕刻特性、以及良好微影特性之光阻下層膜而良好地發揮功能,進而完成本發明。
亦即,本發明作為第1觀點,係關於一種膜形成用組成物,其係含有使用二種以上酸性化合物進行水解性矽烷化合物之水解及縮合而獲得之水解縮合物、及溶劑;其特徵係
上述水解性矽烷化合物,含有下述式(1)所表示之含胺基之矽烷:
[化1]
(式(1)中,R1
係與矽原子鍵結之基團,互相獨立地表示含有胺基之有機基;
R2
係與矽原子鍵結之基團,表示可經取代之烷基、可經取代之芳基、可經取代之芳烷基、可經取代之鹵化烷基、可經取代之鹵化芳基、可經取代之鹵化芳烷基、可經取代之烷氧烷基、可經取代之烷氧芳基、可經取代之烷氧芳烷基、或可經取代之烯基,或者表示含有環氧基、丙烯醯基、甲基丙烯醯基、巰基或氰基之有機基;
R3
係與矽原子鍵結之基團或原子,互相獨立地表示烷氧基、芳烷氧基、醯氧基或鹵原子;
a係1~2之整數,b係0~1之整數,並滿足a+b≦2)。
作為第2觀點,係關於第1觀點所記載之膜形成用組成物,其中,上述二種以上酸性化合物,含有選自鹽酸、硝酸、磷酸、硫酸、硼酸、雜多酸、側氧碳酸(oxocarbonic acid)、含磺酸基之有機酸、含磷酸基之有機酸、含羧基之有機酸及含酚性羥基之有機酸所成群中相異之二種以上。
作為第3觀點,係關於第2觀點所記載之膜形成用組成物,其中,上述二種以上酸性化合物,含有選自硝酸、硫酸、側氧碳酸、含磺酸基之有機酸及含羧基之有機酸所成群中相異之二種以上。
作為第4觀點,係關於第2觀點所記載之膜形成用組成物,其中,上述二種以上酸性化合物,含有選自硫酸及含磺酸基之有機酸所成群中至少一種、及選自鹽酸、硝酸、磷酸、硼酸、雜多酸、側氧碳酸、含磷酸基之有機酸、含羧基之有機酸及含酚性羥基之有機酸所成群中至少一種。
作為第5觀點,係關於第2觀點至第4觀點中任一者所記載之膜形成用組成物,其中,上述側氧碳酸,含有選自三角酸、方酸及玫棕酸之至少一種。
作為第6觀點,係關於第2觀點至第5觀點中任一者所記載之膜形成用組成物,其中,上述含磺酸基之有機酸,含有選自芳香族磺酸、飽和脂肪族磺酸及不飽和脂肪族磺酸之至少一種。
作為第7觀點,係關於第6觀點所記載之膜形成用組成物,其中,上述含磺酸基之有機酸,含有選自芳香族磺酸及飽和脂肪族磺酸之至少一種。
作為第8觀點,係關於第2觀點至第7觀點中任一者所記載之膜形成用組成物,其中,上述含羧基之有機酸,含有選自甲酸、草酸、芳香族羧酸、飽和脂肪族羧酸及不飽和脂肪族羧酸之至少一種。
作為第9觀點,係關於第8觀點所記載之膜形成用組成物,其中,上述含羧基之有機酸,含有不飽和脂肪族羧酸。
作為第10觀點,係關於第1觀點至第9觀點中任一者所記載之膜形成用組成物,其中,該含有胺基之有機基,係下述式(A1)所表示之基團:
[化2]
(式(A1)中,R101
及R102
互相獨立地表示氫原子或烴基,L表示可經取代之伸烷基)。
作為第11觀點,係關於第10觀點所記載之膜形成用組成物,其中,上述伸烷基,係碳原子數1至10之直鏈狀或支鏈狀伸烷基。
作為第12觀點,係關於第1觀點至第11觀點中任一者所記載之膜形成用組成物,其中,上述膜形成用組成物係使用於微影步驟之光阻下層膜形成用。
作為第13觀點,係關於一種光阻下層膜,其特徵係由第1觀點至第12觀點中任一者所記載之膜形成用組成物所獲得。
作為第14觀點,係關於一種半導體元件之製造方法,其特徵係包含:
於基板上形成有機下層膜之步驟;
於上述有機下層膜上使用第1觀點至第12觀點中任一者所記載之膜形成用組成物來形成光阻下層膜之步驟;及
於上述光阻下層膜上形成光阻膜之步驟。
[發明之效果]
藉由使用本發明之膜形成用組成物,除了能夠以旋轉塗佈法等濕製程容易地成膜,並可獲得適合作為光阻下層膜之膜,該膜,在三層製程中與光阻膜及有機下層膜同時使用之情況下可實現良好的微影特性,並進一步地顯示對形成為上層之光阻膜用組成物之溶劑的耐性及對氟系氣體之良好的蝕刻特性。
藉由使用此種膜形成用組成物,可靠性更高之半導體元件之製造為可期待的。
以下,進一步詳細地說明本發明。
再者,本發明之膜形成用組成物,含有水解性矽烷化合物之水解縮合物,但此水解縮合物中,除了完全完成縮合之縮合物之矽氧烷聚合物,亦包含未完全完成縮合之部分水解縮合物之矽氧烷聚合物。此種部分水解縮合物,亦與完全完成縮合之縮合物相同地,係藉由矽烷化合物之水解及縮合而獲得之聚合物,但由於其部分止於水解而未縮合,因此為殘留有Si-OH基者。
此外,本發明中固體成分,意指組成物中溶劑以外之成分。
式(1)中,R1
係與矽原子鍵結之基團,表示含有胺基之有機基;R2
係與矽原子鍵結之基團,表示可經取代之烷基、可經取代之芳基、可經取代之芳烷基、可經取代之鹵化烷基、可經取代之鹵化芳基、可經取代之鹵化芳烷基、可經取代之烷氧烷基、可經取代之烷氧芳基、可經取代之烷氧芳烷基、或可經取代之烯基,或者表示含有環氧基、丙烯醯基、甲基丙烯醯基、巰基或氰基之有機基;R3
係與矽原子鍵結之基團或原子,互相獨立地表示烷氧基、芳烷氧基、醯氧基或鹵原子;a係1~2之整數,b係0~1之整數,並滿足a+b≦2。
式(1)之烷基,係由烷移除一個氫原子而衍生之1價的基團,可為直鏈狀、支鏈狀、環狀之任一者;烷基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下,再進一步更佳為10以下。
作為直鏈狀或支鏈狀烷基之具體例,可列舉:甲基、乙基、正丙基、異丙基、正丁基、異丁基、二級丁基、三級丁基、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、1-乙基-2-甲基-正丙基等,但不限定於此等。
作為環狀烷基之具體例,可列舉:環丙基、環丁基、1-甲基-環丙基、2-甲基-環丙基、環戊基、1-甲基-環丁基、2-甲基-環丁基、3-甲基-環丁基、1,2-二甲基-環丙基、2,3-二甲基-環丙基、1-乙基-環丙基、2-乙基-環丙基、環己基、1-甲基-環戊基、2-甲基-環戊基、3-甲基-環戊基、1-乙基-環丁基、2-乙基-環丁基、3-乙基-環丁基、1,2-二甲基-環丁基、1,3-二甲基-環丁基、2,2-二甲基-環丁基、2,3-二甲基-環丁基、2,4-二甲基-環丁基、3,3-二甲基-環丁基、1-正丙基-環丙基、2-正丙基-環丙基、1-異丙基-環丙基、2-異丙基-環丙基、1,2,2-三甲基-環丙基、1,2,3-三甲基-環丙基、2,2,3-三甲基-環丙基、1-乙基-2-甲基-環丙基、2-乙基-1-甲基-環丙基、2-乙基-2-甲基-環丙基、2-乙基-3-甲基-環丙基等環烷基;雙環丁基、雙環戊基、雙環己基、雙環庚基、雙環辛基、雙環壬基、雙環癸基等雙環烷基等,但不限定於此等。
式(1)之芳基,可為苯基、移除縮合環芳香族烴化合物之一個氫原子而衍生之1價的基團、移除環連接芳香族烴化合物之一個氫原子而衍生之1價的基團之任一者,其碳原子數不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下。
作為其具體例,可列舉:苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基、1-稠四苯基、2-稠四苯基、5-稠四苯基、2-䓛基(2-chrysenyl group)、1-芘基、2-芘基、稠五苯基、苯并芘基、聯伸三苯基;聯苯-2-基、聯苯-3-基、聯苯-4-基、對聯三苯-4-基、間聯三苯-4-基、鄰聯三苯-4-基、1,1’-聯萘-2-基、2,2’-聯萘-1-基等,但不限定於此等。
式(1)之芳烷基,係芳基取代之烷基,作為此種芳基及烷基之具體例,可列舉與上述相同者。芳烷基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下。
作為芳烷基之具體例,可列舉:苯甲基(苄基)、2-苯基伸乙基、3-苯基-正丙基、4-苯基-正丁基、5-苯基-正戊基、6-苯基-正己基、7-苯基-正庚基、8-苯基-正辛基、9-苯基-正壬基、10-苯基-正癸基等,但不限定於此等。
式(1)之鹵化烷基,係鹵原子取代之烷基,作為此種烷基之具體例,可列舉與上述相同者。
鹵化烷基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下,進一步再更佳為10以下。
作為該鹵原子及式(1)之鹵原子,可列舉:氟原子、氯原子、溴原子、碘原子。
作為鹵化烷基之具體例,可列舉:一氟甲基、二氟甲基、三氟甲基、溴二氟甲基、2-氯乙基、2-溴乙基、1,1-二氟乙基、2,2,2-三氟乙基、1,1,2,2-四氟乙基、2-氯-1,1,2-三氟乙基、五氟乙基、3-溴丙基、2,2,3,3-四氟丙基、1,1,2,3,3,3-六氟丙基、1,1,1,3,3,3-六氟丙-2-基、3-溴-2-甲基丙基、4-溴丁基、全氟戊基等,但不限定於此等。
式(1)之鹵化芳基,係鹵原子取代之芳基,作為此種芳基及鹵原子之具體例,可列舉與上述相同者。
鹵化芳基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下。
作為鹵化芳基之具體例,可列舉:2-氟苯基、3-氟苯基、4-氟苯基、2,3-二氟苯基、2,4-二氟苯基、2,5-二氟苯基、2,6-二氟苯基、3,4-二氟苯基、3,5-二氟苯基、2,3,4-三氟苯基、2,3,5-三氟苯基、2,3,6-三氟苯基、2,4,5-三氟苯基、2,4,6-三氟苯基、3,4,5-三氟苯基、2,3,4,5-四氟苯基、2,3,4,6-四氟苯基、2,3,5,6-四氟苯基、五氟苯基、2-氟-1-萘基、3-氟-1-萘基、4-氟-1-萘基、6-氟-1-萘基、7-氟-1-萘基、8-氟-1-萘基、4,5-二氟-1-萘基、5,7-二氟-1-萘基、5,8-二氟-1-萘基、5,6,7,8-四氟-1-萘基、七氟-1-萘基、1-氟-2-萘基、5-氟-2-萘基、6-氟-2-萘基、7-氟-2-萘基、5,7-二氟-2-萘基、七氟-2-萘基等,但不限定於此等。
式(1)之鹵化芳烷基,係鹵原子取代之芳烷基,作為此種芳烷基及鹵原子之具體例,可列舉與上述相同者。
鹵化芳烷基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下。
作為鹵化芳烷基之具體例,可列舉:2-氟苄基、3-氟苄基、4-氟苄基、2,3-二氟苄基、2,4-二氟苄基、2,5-二氟苄基、2,6-二氟苄基、3,4-二氟苄基、3,5-二氟苄基、2,3,4-三氟苄基、2,3,5-三氟苄基、2,3,6-三氟苄基、2,4,5-三氟苄基、2,4,6-三氟苄基、2,3,4,5-四氟苄基、2,3,4,6-四氟苄基、2,3,5,6-四氟苄基、2,3,4,5,6-五氟苄基等,但不限定於此等。
式(1)之烷氧烷基,係烷氧基取代之烷基,烷氧烷基中烷氧基取代之烷基,可為直鏈狀、支鏈狀、環狀之任一者,作為此種烷基之具體例,可列舉與上述相同者。烷氧烷基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下,進一步再更佳為10以下。
作為烷氧烷基中在烷基上進行取代之烷氧基及式(1)中烷氧基之具體例,可列舉:甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基、三級丁氧基、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、1-乙基-2-甲基-正丙氧基等鏈狀或支鏈狀之烷氧基;環丙氧基、環丁氧基、1-甲基-環丙氧基、2-甲基-環丙氧基、環戊氧基、1-甲基-環丁氧基、2-甲基-環丁氧基、3-甲基-環丁氧基、1,2-二甲基-環丙氧基、2,3-二甲基-環丙氧基、1-乙基-環丙氧基、2-乙基-環丙氧基、環己氧基、1-甲基-環戊氧基、2-甲基-環戊氧基、3-甲基-環戊氧基、1-乙基-環丁氧基、2-乙基-環丁氧基、3-乙基-環丁氧基、1,2-二甲基-環丁氧基、1,3-二甲基-環丁氧基、2,2-二甲基-環丁氧基、2,3-二甲基-環丁氧基、2,4-二甲基-環丁氧基、3,3-二甲基-環丁氧基、1-正丙基-環丙氧基、2-正丙基-環丙氧基、1-異丙基-環丙氧基、2-異丙基-環丙氧基、1,2,2-三甲基-環丙氧基、1,2,3-三甲基-環丙氧基、2,2,3-三甲基-環丙氧基、1-乙基-2-甲基-環丙氧基、2-乙基-1-甲基-環丙氧基、2-乙基-2-甲基-環丙氧基、2-乙基-3-甲基-環丙氧基等環狀之烷氧基等,但不限定於此等。
作為烷氧烷基之具體例,可列舉:甲氧基甲基、乙氧基甲基、1-乙氧基乙基、2-乙氧基乙基等低級烷氧低級烷基等,但不限定於此等。
式(1)之烷氧芳基,係烷氧基取代之芳基,作為此種烷氧基及芳基之具體例,可列舉與上述相同者。烷氧芳基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下。
作為烷氧芳基之具體例,可列舉:2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-(1-乙氧基)苯基、3-(1-乙氧基)苯基、4-(1-乙氧基)苯基、2-(2-乙氧基)苯基、3-(2-乙氧基)苯基、4-(2-乙氧基)苯基、2-甲氧基萘-1-基、3-甲氧基萘-1-基、4-甲氧基萘-1-基、5-甲氧基萘-1-基、6-甲氧基萘-1-基、7-甲氧基萘-1-基等,但不限定於此等。
式(1)之烷氧芳烷基,係烷氧基取代之芳烷基,作為此種烷氧基及芳烷基之具體例,可列舉與上述相同者。烷氧芳烷基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下。
作為烷氧芳烷基之具體例,可列舉:3-(甲氧基苯基)苄基、4-(甲氧基苯基)苄基等,但不限定於此等。
式(1)之烯基,可為直鏈狀、支鏈狀之任一者,其碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下,進一步再更佳為10以下。
作為烯基之具體例,可列舉:乙烯基、1-丙烯基、2-丙烯基、1-甲基-1-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-正丙基乙烯基、1-甲基-1-丁烯基、1-甲基-2-丁烯基、1-甲基-3-丁烯基、2-乙基-2-丙烯基、2-甲基-1-丁烯基、2-甲基-2-丁烯基、2-甲基-3-丁烯基、3-甲基-1-丁烯基、3-甲基-2-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1-異丙基乙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-環戊烯基、2-環戊烯基、3-環戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、1-甲基-2-戊烯基、1-甲基-3-戊烯基、1-甲基-4-戊烯基、1-正丁基乙烯基、2-甲基-1-戊烯基、2-甲基-2-戊烯基、2-甲基-3-戊烯基、2-甲基-4-戊烯基、2-正丙基-2-丙烯基、3-甲基-1-戊烯基、3-甲基-2-戊烯基、3-甲基-3-戊烯基、3-甲基-4-戊烯基、3-乙基-3-丁烯基、4-甲基-1-戊烯基、4-甲基-2-戊烯基、4-甲基-3-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1-甲基-2-乙基-2-丙烯基、1-二級丁基乙烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、1-異丁基乙烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、2-異丙基-2-丙烯基、3,3-二甲基-1-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、1-正丙基-1-丙烯基、1-正丙基-2-丙烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-三級丁基乙烯基、1-甲基-1-乙基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基、1-異丙基-1-丙烯基、1-異丙基-2-丙烯基、1-甲基-2-環戊烯基、1-甲基-3-環戊烯基、2-甲基-1-環戊烯基、2-甲基-2-環戊烯基、2-甲基-3-環戊烯基、2-甲基-4-環戊烯基、2-甲基-5-環戊烯基、2-亞甲基-環戊基、3-甲基-1-環戊烯基、3-甲基-2-環戊烯基、3-甲基-3-環戊烯基、3-甲基-4-環戊烯基、3-甲基-5-環戊烯基、3-亞甲基-環戊基、1-環己烯基、2-環己烯基、3-環己烯基等,但不限定於此等。
作為式(1)之含有環氧基之有機基,可列舉:環氧丙氧甲基、環氧丙氧乙基、環氧丙氧丙基、環氧丙氧丁基、環氧環己基等,但不限定於此等。
作為式(1)之含有丙烯醯基之有機基,可列舉:丙烯醯基甲基、丙烯醯基乙基、丙烯醯基丙基等,但不限定於此等。
作為式(1)之含有甲基丙烯醯基之有機基,可列舉:甲基丙烯醯基甲基、甲基丙烯醯基乙基、甲基丙烯醯基丙基等,但不限定於此等。
作為式(1)之含有巰基之有機基,可列舉:乙基巰基、丁基巰基、己基巰基、辛基巰基等,但不限定於此等。
作為式(1)之含有氰基之有機基,可列舉氰乙基、氰丙基等,但不限定於此等。
作為式(1)之芳烷氧基,係由芳烷醇之羥基移除氫原子而衍生之基團,作為此種芳烷基之具體例,可列舉與上述相同者。
芳烷氧基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下。
作為芳烷氧基之具體例,可列舉:苯基甲基氧基(苄氧基)、2-苯基伸乙基氧基、3-苯基-正丙基氧基、4-苯基-正丁基氧基、5-苯基-正戊基氧基、6-苯基-正己基氧基、7-苯基-正庚基氧基、8-苯基-正辛基氧基、9-苯基-正壬基氧基、10-苯基-正癸基氧基等,但不限定於此等。
式(1)之醯氧基,係由羧酸化合物之羧基移除氫原子而衍生之基團,典型地,可列舉:由烷基羧酸、芳基羧酸或芳烷基羧酸之羧基移除氫原子而衍生之烷基羰氧基、芳基羰氧基或芳烷基羰氧基,但不限定於此等。作為此種烷基羧酸、芳基羧酸及芳烷基羧酸之烷基、芳基及芳烷基之具體例,可列舉與上述相同者。
作為醯氧基之具體例,可列舉:甲基羰氧基、乙基羰氧基、正丙基羰氧基、異丙基羰氧基、正丁基羰氧基、異丁基羰氧基、二級丁基羰氧基、三級丁基羰氧基、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、甲苯磺醯基羰氧基等,但不限定於此等。
式(A1)中,R101
及R102
互相獨立地表示氫原子或烴基,L互相獨立地表示可經取代之伸烷基。
作為式(A1)中之烴基,可列舉:烷基、烯基、芳基等,但不限定於此等。
作為此種烷基、烯基及芳基之具體例,可列舉與上述相同者。
由再現性佳地實現優異微影特性之觀點而言,R101
及R102
,較佳為氫原子、烷基、芳基,更佳為氫原子、碳原子數1至5之烷基、碳原子數6至10之芳基;再更佳為R101
為氫原子,R102
為氫原子、碳原子數1至5之烷基、碳原子數6至10之芳基,或者,R101
及R102
同時為碳原子數1至5之烷基或碳原子數6至10之芳基;再進一步更佳為R101
及R102
同時為氫原子。
此外,作為式(A1)中之伸烷基,可列舉與上述相同者,可為直鏈狀或支鏈狀之任一者,其碳原子數,一般為1至10,較佳為1至5。
其中,較佳為亞甲基、伸乙基、三亞甲基、四亞甲基、五亞甲基、六亞甲基、七亞甲基、八亞甲基、九亞甲基、十亞甲基等直鏈狀伸烷基。
a係1~2之整數,b係0~1之整數,並滿足a+b≦2,但從優異微影特性、對光阻膜用組成物之溶劑之耐性、較佳蝕刻速率之平衡之觀點等而言,較佳係b為0,更佳係a為1,且b為0。
上述水解性矽烷化合物中以式(1)表示之含胺基之矽烷之含量,為任意,但由再現性佳地實現優異微影特性之觀點而言,較佳為0.01莫耳%至20莫耳%,更佳為0.1莫耳%至5莫耳%,其剩餘部分使用其他水解性矽烷。
本發明之膜形成用組成物,以膜密度等膜物性之調整等為目的,上述水解性矽烷化合物,在含有式(1)所表示之含胺基之矽烷的同時,亦可含有例如選自下述式(2)所表示之水解性矽烷及下述式(3)所表示之水解性矽烷之至少一種作為其他水解性矽烷。
式(2)中,R4
係藉由Si-C鍵結而與矽原子鍵結之基團,互相獨立地表示可經取代之烷基、可經取代之芳基、可經取代之芳烷基、可經取代之鹵化烷基、可經取代之鹵化芳基、可經取代之鹵化芳烷基、可經取代之烷氧烷基、可經取代之烷氧芳基、可經取代之烷氧芳烷基、或可經取代之烯基,或者表示含有環氧基、丙烯醯基、甲基丙烯醯基、巰基、醯胺基、烷氧基或磺醯基之有機基、或其等之組合。
此外,R5
係與矽原子鍵結之基團或原子,互相獨立地表示烷氧基、芳烷氧基、醯氧基或鹵原子。
d,表示0至3之整數。
作為上述R4
之各基團及原子之具體例、以及其等較佳之碳原子數,可列舉與R2
相關之上述之基團及原子以及碳原子數。
作為上述R5
之各基團及原子之具體例、以及其等較佳之碳原子數,可列舉與R3
相關之上述之基團及原子以及碳原子數。
式(3)中,R6
係藉由Si-C鍵結而與矽原子鍵結之基團,互相獨立地表示可經取代之烷基、可經取代之芳基、可經取代之芳烷基、可經取代之鹵化烷基、可經取代之鹵化芳基、可經取代之鹵化芳烷基、可經取代之烷氧烷基、可經取代之烷氧芳基、可經取代之烷氧芳烷基、或可經取代之烯基,或者表示含有環氧基、丙烯醯基、甲基丙烯醯基、巰基、醯胺基、烷氧基或磺醯基之有機基、或其等之組合。
此外,R7
係與矽原子鍵結之基團或原子,互相獨立地表示烷氧基、芳烷氧基、醯氧基或鹵原子。
Y係藉由Si-C鍵結而與矽原子鍵結之基團,互相獨立地表示伸烷基或伸芳基。
e係表示0或1之整數,f係表示0或1之整數。
作為上述R6
及R7
之各基團及原子之具體例、以及其等較佳之碳原子數,可列舉上述之基團及原子以及碳原子數。
此外,作為上述Y之伸烷基之具體例,可列舉:亞甲基、伸乙基、三亞甲基、四亞甲基、五亞甲基、六亞甲基、七亞甲基、八亞甲基、九亞甲基、十亞甲基等直鏈狀伸烷基,1-甲基三亞甲基、2-甲基三亞甲基、1,1-二甲基伸乙基、1-甲基四亞甲基、2-甲基四亞甲基、1,1-二甲基三亞甲基、1,2-二甲基三亞甲基、2,2-二甲基三亞甲基、1-乙基三亞甲基等支鏈狀伸烷基等伸烷基;甲三基、乙-1,1,2-三基、乙-1,2,2-三基、乙-2,2,2-三基、丙-1,1,1-三基、丙-1,1,2-三基、丙-1,2,3-三基、丙-1,2,2-三基、丙-1,1,3-三基、丁-1,1,1-三基、丁-1,1,2-三基、丁-1,1,3-三基、丁-1,2,3-三基、丁-1,2,4-三基、丁-1,2,2-三基、丁-2,2,3-三基、2-甲基丙-1,1,1-三基、2-甲基丙-1,1,2-三基、2-甲基丙-1,1,3-三基等烷三基等,但不限定於此等。
作為上述Y之伸芳基之具體例,可列舉:1,2-伸苯基、1,3-伸苯基、1,4-伸苯基;1,5-萘二基、1,8-萘二基、2,6-萘二基、2,7-萘二基、1,2-蒽二基、1,3-蒽二基、1,4-蒽二基、1,5-蒽二基、1,6-蒽二基、1,7-蒽二基、1,8-蒽二基、2,3-蒽二基、2,6-蒽二基、2,7-蒽二基、2,9-蒽二基、2,10-蒽二基、9,10-蒽二基等由縮合環芳香族烴化合物之芳香環上移除二個氫原子而衍生之基團;4,4’-聯苯二基、4,4”-對聯三苯二基之由環連接芳香族烴化合物之芳香環上移除二個氫原子而衍生之基團等,但不限定於此等。
e較佳為0或1,更佳為0。f較佳為1。
作為式(2)所表示之水解性矽烷之具體例,可列舉:四甲氧基矽烷、四氯矽烷、四乙醯氧基矽烷、四乙氧基矽烷、四正丙氧基矽烷、四異丙氧基矽烷、四正丁氧基矽烷、甲基三甲氧基矽烷、甲基三氯矽烷、甲基三乙醯氧基矽烷、甲基三甲氧基矽烷、甲基三丙氧基矽烷、甲基三丁氧基矽烷、甲基三戊氧基矽烷、甲基三苯氧基矽烷、甲基三苄氧基矽烷、甲基三苯乙氧基矽烷、環氧丙氧甲基三甲氧基矽烷、環氧丙氧甲基三乙氧基矽烷、α-環氧丙氧乙基三甲氧基矽烷、α-環氧丙氧乙基三乙氧基矽烷、β-環氧丙氧乙基三甲氧基矽烷、β-環氧丙氧乙基三乙氧基矽烷、α-環氧丙氧丙基三甲氧基矽烷、α-環氧丙氧丙基三乙氧基矽烷、β-環氧丙氧丙基三甲氧基矽烷、β-環氧丙氧丙基三乙氧基矽烷、γ-環氧丙氧丙基三甲氧基矽烷、γ-環氧丙氧丙基三乙氧基矽烷、γ-環氧丙氧丙基三丙氧基矽烷、γ-環氧丙氧丙基三丁氧基矽烷、γ-環氧丙氧丙基三苯氧基矽烷、α-環氧丙氧丁基三甲氧基矽烷、α-環氧丙氧丁基三乙氧基矽烷、β-環氧丙氧丁基三乙氧基矽烷、γ-環氧丙氧丁基三甲氧基矽烷、γ-環氧丙氧丁基三乙氧基矽烷、δ-環氧丙氧丁基三甲氧基矽烷、δ-環氧丙氧丁基三乙氧基矽烷、(3,4-環氧環己基)甲基三甲氧基矽烷、(3,4-環氧環己基)甲基三乙氧基矽烷、β-(3,4-環氧環己基)乙基三甲氧基矽烷、β-(3,4-環氧環己基)乙基三乙氧基矽烷、β-(3,4-環氧環己基)乙基三丙氧基矽烷、β-(3,4-環氧環己基)乙基三丁氧基矽烷、β-(3,4-環氧環己基)乙基三苯氧基矽烷、γ-(3,4-環氧環己基)丙基三甲氧基矽烷、γ-(3,4-環氧環己基)丙基三乙氧基矽烷、δ-(3,4-環氧環己基)丁基三甲氧基矽烷、δ-(3,4-環氧環己基)丁基三乙氧基矽烷、環氧丙氧甲基甲基二甲氧基矽烷、環氧丙氧甲基甲基二乙氧基矽烷、α-環氧丙氧乙基甲基二甲氧基矽烷、α-環氧丙氧乙基甲基二乙氧基矽烷、β-環氧丙氧乙基甲基二甲氧基矽烷、β-環氧丙氧乙基乙基二甲氧基矽烷、α-環氧丙氧丙基甲基二甲氧基矽烷、α-環氧丙氧丙基甲基二乙氧基矽烷、β-環氧丙氧丙基甲基二甲氧基矽烷、β-環氧丙氧乙基二甲氧基矽烷、γ-環氧丙氧丙基甲基二甲氧基矽烷、γ-環氧丙氧丙基甲基二乙氧基矽烷、γ-環氧丙氧丙基甲基二丙氧基矽烷、γ-環氧丙氧丙基甲基二丁氧基矽烷、γ-環氧丙氧丙基甲基二苯氧基矽烷、γ-環氧丙氧丙基乙基二甲氧基矽烷、γ-環氧丙氧丙基乙基二乙氧基矽烷、γ-環氧丙氧丙基乙烯基二甲氧基矽烷、γ-環氧丙氧丙基乙烯基二乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三氯矽烷、乙烯基三乙醯氧基矽烷、乙烯基三乙氧基矽烷、甲氧基苯基三甲氧基矽烷、甲氧基苯基三乙氧基矽烷、甲氧基苯基三乙醯氧基矽烷、甲氧基苯基三氯矽烷、甲氧基苄基三甲氧基矽烷、甲氧基苄基三乙氧基矽烷、甲氧基苄基三乙醯氧基矽烷、甲氧基苄基三氯矽烷、甲氧基苯乙基三甲氧基矽烷、甲氧基苯乙基三乙氧基矽烷、甲氧基苯乙基三乙醯氧基矽烷、甲氧基苯乙基三氯矽烷、乙氧基苯基三甲氧基矽烷、乙氧基苯基三乙氧基矽烷、乙氧基苯基三乙醯氧基矽烷、乙氧基苯基三氯矽烷、乙氧基苄基三甲氧基矽烷、乙氧基苄基三乙氧基矽烷、乙氧基苄基三乙醯氧基矽烷、乙氧基苄基三氯矽烷、異丙氧基苯基三甲氧基矽烷、異丙氧基苯基三乙氧基矽烷、異丙氧基苯基三乙醯氧基矽烷、異丙氧基苯基三氯矽烷、異丙氧基苄基三甲氧基矽烷、異丙氧基苄基三乙氧基矽烷、異丙氧基苄基三乙醯氧基矽烷、異丙氧基苄基三氯矽烷、三級丁氧基苯基三甲氧基矽烷、三級丁氧基苯基三乙氧基矽烷、三級丁氧基苯基三乙醯氧基矽烷、三級丁氧基苯基三氯矽烷、三級丁氧基苄基三甲氧基矽烷、三級丁氧基苄基三乙氧基矽烷、三級丁氧基苄基三乙醯氧基矽烷、三級丁氧基苄基三氯矽烷、甲氧基萘基三甲氧基矽烷、甲氧基萘基三乙氧基矽烷、甲氧基萘基三乙醯氧基矽烷、甲氧基萘基三氯矽烷、乙氧基萘基三甲氧基矽烷、乙氧基萘基三乙氧基矽烷、乙氧基萘基三乙醯氧基矽烷、乙氧基萘基三氯矽烷、γ-氯丙基三甲氧基矽烷、γ-氯丙基三乙氧基矽烷、γ-氯丙基三乙醯氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、γ-甲基丙烯醯氧丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷、γ-巰基丙基三乙氧基矽烷、氯甲基三甲氧基矽烷、氯甲基三乙氧基矽烷、三乙氧基矽基丙基二烯丙基異氰脲酸酯(triethoxysilylpropyl diallyl isocyanurate)、雙環(2,2,1)庚烯基三乙氧基矽烷、苯磺醯基丙基三乙氧基矽烷、苯磺醯胺基丙基三乙氧基矽烷、二甲胺基丙基三甲氧基矽烷、二甲基二甲氧基矽烷、苯基甲基二甲氧基矽烷、二甲基二乙氧基矽烷、苯基甲基二乙氧基矽烷、γ-氯丙基甲基二甲氧基矽烷、γ-氯丙基甲基二乙氧基矽烷、二甲基二乙醯氧基矽烷、γ-甲基丙烯醯氧丙基甲基二甲氧基矽烷、γ-甲基丙烯醯氧丙基甲基二乙氧基矽烷、γ-巰基丙基甲基二甲氧基矽烷、γ-巰基丙基甲基二乙氧基矽烷、甲基乙烯基二甲氧基矽烷、甲基乙烯基二乙氧基矽烷、及下述式(A-1)至(A-41)所表示之矽烷等,但不限定於此等。
作為式(3)所表示之水解性矽烷之具體例,可列舉:亞甲基雙三甲氧基矽烷、亞甲基雙三氯矽烷、亞甲基雙三乙醯氧基矽烷、伸乙基雙三乙氧基矽烷、伸乙基雙三氯矽烷、伸乙基雙三乙醯氧基矽烷、伸丙基雙三乙氧基矽烷、伸丁基雙三甲氧基矽烷、伸苯基雙三甲氧基矽烷、伸苯基雙三乙氧基矽烷、伸苯基雙甲基二乙氧基矽烷、伸苯基雙甲基二甲氧基矽烷、伸萘基雙三甲氧基矽烷、雙三甲氧基二矽烷、雙三乙氧基二矽烷、雙乙基二乙氧基二矽烷、雙甲基二甲氧基二矽烷等,但不限定於此等。
本發明中,在提供水解縮合物之上述水解性矽烷化合物含有式(1)所表示之含胺基之矽烷以外之其他水解性矽烷之情況下,上述水解性矽烷化合物中其他水解性矽烷之含量,一般為80莫耳%~99.99莫耳%,較佳為95莫耳%~99.9莫耳%。
由提升從本發明之膜形成用組成物獲得之膜的交聯密度,抑制光阻膜成分往該獲得之膜之擴散等,並維持、改善該光阻膜之光阻特性之觀點等而言,上述水解性矽烷化合物,較佳為含有式(2)所表示之水解性矽烷;更佳為含有三官能性之式(2)所表示之水解性矽烷及四官能性之式(2)所表示之水解性矽烷;再更佳為含有選自烷基三烷氧基矽烷及芳基三烷氧基矽烷之至少一種、及四烷氧基矽烷;再進一步更佳為含有選自甲基三烷氧基矽烷及苯基三烷氧基矽烷之至少一種、及四烷氧基矽烷。
在此情況下,三官能性之式(2)所表示之水解性矽烷及四官能性之式(2)所表示之水解性矽烷之比,以莫耳比計,一般為10:90~90:10,較佳為70:30~20:80。
在用於獲得本發明之膜形成用組成物所含之水解縮合物的上述水解性矽烷化合物之水解及縮合中,使用二種以上酸性化合物。
作為二種以上酸性化合物,只要是在結構上相異者則不各別特別限定,可為無機酸、有機酸之任一者。
作為無機酸,可列舉:鹽酸、硝酸、磷酸、硫酸、硼酸、雜多酸等,但不限定於此等。
作為雜多酸,可列舉:磷鉬酸、矽鉬酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等。
此等中,由再現性佳地實現優異微影特性之觀點、提升水解縮合物溶液之保存穩定性之觀點等而言,較佳為硝酸、磷酸、硫酸,更佳為硝酸。
有機酸,為在分子內具有磺酸基、磷酸基、羧基、酚性羥基等酸性基者,該有機酸中酸性基可複數存在,複數之酸性基,可互相為相同,亦可相異。
本發明較佳之一態樣中,作為含磺酸基之有機酸,可列舉例如:芳香族磺酸、飽和脂肪族磺酸、不飽和脂肪族磺酸等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為芳香族磺酸、飽和脂肪族磺酸。
芳香族磺酸,係芳香族化合物之至少一個氫原子被磺酸基取代者,構成該種芳香族化合物之芳香環之碳原子數,不特別限定,一般為6~20,較佳為6~14,再更佳為6~10;該芳香環,亦可經氟等鹵原子、甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基等烷基、乙烯基等烯基、三氟甲基等鹵化烷基、全氟乙烯基等鹵化烯基等之取代基取代,一般該取代基之數量為0~3。
此外,磺酸基之數量,不特別限定,一般為1~3,較佳為1~2,再更佳為1。
作為芳香族磺酸,典型地,可列舉:無取代芳香族磺酸、烷基或烯基芳香族磺酸、鹵化烷基或鹵化烯基芳香族磺酸、鹵化芳香族磺酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代芳香族磺酸、烷基芳香族磺酸,更佳為烷基芳香族磺酸。
作為無取代芳香族磺酸之具體例,可列舉:苯磺酸、苯-1,2-二磺酸、苯-1,3-二磺酸、苯-1,4-二磺酸、苯-1,3,5-三磺酸、2-萘磺酸、蒽磺酸、菲磺酸、芘磺酸等,但不限定於此等。
作為烷基或烯基芳香族磺酸之具體例,可列舉:對甲苯磺酸、對苯乙烯磺酸、對異丙苯磺酸、對十二基苯磺酸、二己基苯磺酸、2,5-二己基苯磺酸、3,5-雙(三級丁基)苯磺酸、3,5-雙(異丙基)苯磺酸、2,4,6-三(三級丁基)苯磺酸、2,4,6-三(異丙基)苯磺酸、5,8-二丁基-2-萘磺酸、6,7-二丁基-2-萘磺酸、己基萘磺酸、4-己基-1-萘磺酸、7-己基-1-萘磺酸、6-己基-2-萘磺酸、辛基萘磺酸、2-辛基-1-萘磺酸、二壬基萘磺酸、2,7-二壬基-4-萘磺酸、二壬基萘二磺酸、十二基萘磺酸、3-十二基-2-萘磺酸等,但不限定於此等。
作為鹵化烷基或鹵化烯基芳香族磺酸之具體例,可列舉:2-三氟甲基苯磺酸、2-三氯甲基苯磺酸、2-三溴甲基苯磺酸、2-三碘甲基苯磺酸、3-三氟甲基苯磺酸、3-三氯甲基苯磺酸、3-三溴甲基苯磺酸、3-三碘甲基苯磺酸、4-三氟甲基苯磺酸、4-三氯甲基苯磺酸、4-三溴甲基苯磺酸、4-三碘甲基苯磺酸、2,6-雙(三氟甲基)苯磺酸、2,6-雙(三氯甲基)苯磺酸、2,6-雙(三溴甲基)苯磺酸、2,6-雙(三碘甲基)苯磺酸、3,5-雙(三氟甲基)苯磺酸、3,5-雙(三氯甲基)苯磺酸、3,5-雙(三溴甲基)苯磺酸、3,5-雙(三碘甲基)苯磺酸、4-全氟乙烯基苯磺酸等,但不限定於此等。
作為鹵化芳香族磺酸之具體例,可列舉:2-氟苯磺酸、3-氟苯磺酸、4-氟苯磺酸、2-氯苯磺酸、3-氯苯磺酸、4-氯苯磺酸、2-溴苯磺酸、3-溴苯磺酸、4-溴苯磺酸、2-碘苯磺酸、4-碘苯磺酸、2,4-二氟苯磺酸、2,6-二氟苯磺酸、2,4-二氯苯磺酸、2,6-二氯苯磺酸、2,4-二溴苯磺酸、2,6-二溴苯磺酸、2,4-二碘苯磺酸、2,6-二碘苯磺酸、2,4,6-三氟苯磺酸、3,4,5-三氟苯磺酸、2,4,6-三氯苯磺酸、3,4,5-三氯苯磺酸、2,4,6-三溴苯磺酸、3,4,5-三溴苯磺酸、2,4,6-三碘苯磺酸、3,4,5-三碘苯磺酸、五氟苯磺酸、五氯苯磺酸、五溴苯磺酸、五碘苯磺酸、氟萘磺酸、氯萘磺酸、溴萘磺酸、碘萘磺酸、氟蒽磺酸、氯蒽磺酸、溴蒽磺酸、碘蒽磺酸等,但不限定於此等。
由再現性佳地實現優異光阻特性之觀點而言,在芳香族磺酸之芳香環之取代基為鹵原子之情況下,較佳為氟原子;為烷基之情況下,較佳為碳原子數1~3之烷基,更佳為甲基或乙基,再更佳為甲基。
飽和脂肪族磺酸,係烷或環烷化合物之至少一個氫原子被磺酸基取代者,構成該種烷或環烷化合物之碳原子數,不特別限定,一般為1~10,較佳為1~5,再更佳為1~3;該烷化合物,亦可經氟等鹵原子、苯基等芳基等之取代基取代,一般該取代基之數量為0~3。
作為飽和脂肪族磺酸,典型地,可列舉:無取代飽和脂肪族磺酸、鹵化飽和脂肪族磺酸、芳基飽和脂肪族磺酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代飽和脂肪族磺酸、鹵化飽和脂肪族磺酸,更佳為鹵化飽和脂肪族磺酸。
作為無取代脂肪族磺酸之具體例,可列舉:甲磺酸、甲二磺酸、乙磺酸、乙二磺酸、丙磺酸、丁磺酸、戊磺酸、己磺酸、庚磺酸、辛磺酸、壬磺酸、癸磺酸、十一磺酸、十二磺酸、十三磺酸、十四磺酸、十五磺酸、十六磺酸、十七磺酸、十八磺酸、十九磺酸、二十磺酸、二十一磺酸、二十二磺酸、二十三磺酸、二十四磺酸等鏈狀或支鏈狀烷磺酸、樟腦磺酸等環烷磺酸等,但不限定於此等。
作為鹵化飽和脂肪族磺酸之具體例,可列舉:氟甲磺酸、二氟甲磺酸、三氟甲磺酸、氯甲磺酸、二氯甲磺酸、三氯甲磺酸、溴甲磺酸、二溴甲磺酸、三溴甲磺酸、碘甲磺酸、二碘甲磺酸、三碘甲磺酸、氟乙磺酸、二氟乙磺酸、三氟乙磺酸、五氟乙磺酸、氯乙磺酸、二氯乙磺酸、三氯乙磺酸、五氯乙磺酸、三溴乙磺酸、五溴乙磺酸、三碘乙磺酸、五碘乙磺酸、氟丙磺酸、三氟丙磺酸、七氟丙磺酸、氯丙磺酸、三氯丙磺酸、七氯丙磺酸、溴丙磺酸、三溴丙磺酸、七溴丙磺酸、三碘丙磺酸、七碘丙磺酸、三氟丁磺酸、九氟丁磺酸、三氯丁磺酸、九氯丁磺酸、三溴丁磺酸、九溴丁磺酸、三碘丁磺酸、九碘丁磺酸、三氟戊磺酸、全氟戊磺酸、三氯戊磺酸、全氯戊磺酸、三溴戊磺酸、全溴戊磺酸、三碘戊磺酸、全碘戊磺酸、三氟己磺酸、全氟己磺酸、三氯己磺酸、全氯己磺酸、全溴己磺酸、全碘己磺酸、三氟庚磺酸、全氟庚磺酸、三氯庚磺酸、全氯庚磺酸、全溴庚磺酸、全碘庚磺酸、三氟辛磺酸、全氟辛磺酸、三氯辛磺酸、全氯辛磺酸、全溴辛磺酸、全碘辛磺酸、三氟壬磺酸、全氟壬磺酸、三氯壬磺酸、全氯壬磺酸、全溴壬磺酸、全碘壬磺酸、三氟癸磺酸、全氟癸磺酸、三氯癸磺酸、全氯癸磺酸、全溴癸磺酸、全碘癸磺酸、三氟十一磺酸、全氟十一磺酸、三氯十一磺酸、全氯十一磺酸、全溴十一磺酸、全碘十一磺酸、三氟十二磺酸、全氟十二磺酸、三氯十二磺酸、全氯十二磺酸、全溴十二磺酸、全碘十二磺酸、三氟十三磺酸、全氟十三磺酸、三氯十三磺酸、全氯十三磺酸、全溴十三磺酸、全碘十三磺酸、三氟十四磺酸、全氟十四磺酸、三氯十四磺酸、全氯十四磺酸、全溴十四磺酸、全碘十四磺酸、三氟十五磺酸、全氟十五磺酸、三氯十五磺酸、全氯十五磺酸、全溴十五磺酸、全碘十五磺酸、全氟十六磺酸、全氯十六磺酸、全溴十六磺酸、全碘十六磺酸、全氟十七磺酸、全氯十七磺酸、全溴十七磺酸、全碘十七磺酸、全氟十八磺酸、全氯十八磺酸、全溴十八磺酸、全碘十八磺酸、全氟十九磺酸、全氯十九磺酸、全溴十九磺酸、全碘十九磺酸、全氟二十磺酸、全氯二十磺酸、全溴二十磺酸、全碘二十磺酸、全氟二十一磺酸、全氯二十一磺酸、全溴二十一磺酸、全碘二十一磺酸、全氟二十二磺酸、全氯二十二磺酸、全溴二十二磺酸、全碘二十二磺酸、全氟二十三磺酸、全氯二十三磺酸、全溴二十三磺酸、全碘二十三磺酸、全氟二十四磺酸、全氯二十四磺酸、全溴二十四磺酸、全碘二十四磺酸等,但不限定於此等。
作為芳基飽和脂肪族磺酸之具體例,可列舉:苯基甲磺酸、二苯基甲磺酸、三苯基甲磺酸、1-苯基乙磺酸、2-苯基乙磺酸等,但不限定於此等。
由再現性佳地實現優異光阻特性之觀點而言,在飽和脂肪族磺酸之烷基上進行取代之取代基為鹵原子之情況下,較佳為氟原子;為芳基之情況下,較佳為碳原子數6~10之芳基,更佳為苯基。
不飽和脂肪族磺酸,係烯或炔化合物之至少一個氫原子被磺酸基取代者,構成該種烯或炔化合物之碳原子數,不特別限定,一般為2~10,較佳為2~5,再更佳為2~3;烯或炔化合物,亦可經氟等鹵原子、苯基等芳基等之取代基取代,一般該取代基之數量為0~3。
作為不飽和脂肪族磺酸,典型地,可列舉:無取代不飽和脂肪族磺酸、鹵化不飽和脂肪族磺酸、芳基不飽和脂肪族磺酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代不飽和脂肪族磺酸。
作為無取代不飽和脂肪族磺酸之具體例,可列舉:乙烯磺酸、2-丙烯-1-磺酸、1-丁烯-1-磺酸、3-丁烯-1-磺酸等,但不限定於此等。
本發明較佳之一態樣中,作為含磷酸基之有機酸,可列舉:芳香族磷酸、飽和脂肪族磷酸、不飽和脂肪族磷酸等,但不限定於此等。
芳香族磷酸,係芳香族化合物之至少一個氫原子被磷酸基取代者,構成該種芳香族化合物之芳香環之碳原子數,不特別限定,一般為6~20,較佳為6~14,再更佳為6~10;該芳香環,亦可經氟等鹵原子、甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基等烷基、乙烯基等烯基、三氟甲基等鹵化烷基、全氟乙烯基等鹵化烯基等之取代基取代,一般該取代基之數量為0~3。
此外,磷酸基之數量,不特別限定,一般為1~3,較佳為1~2,再更佳為1。
作為芳香族磷酸,典型地,可列舉:無取代芳香族磷酸、烷基或烯基芳香族磷酸、鹵化烷基或鹵化烯基芳香族磷酸、鹵化芳香族磷酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代芳香族磷酸、烷基芳香族磷酸。
作為無取代芳香族磷酸之具體例,可列舉:苯基磷酸(phenyl phosphate)、1-萘基磷酸(1-naphthyl phosphate)、2-萘基磷酸等,但不限定於此。
作為烷基或烯基芳香族磷酸之具體例,可列舉:甲苯基磷酸(tolyl phosphate)、二甲苯基磷酸(xylyl phosphate)、2-乙基苯基磷酸(2-ethylphenyl phosphate)、3-正丙基苯基二磷酸、4-三級丁基苯基磷酸等,但不限定於此。
作為鹵化烷基或鹵化烯基芳香族磷酸之具體例,可列舉:2-三氟甲基苯基磷酸、2-三氯甲基苯基磷酸、2-三溴甲基苯基磷酸、2-三碘甲基苯基磷酸、3-三氟甲基苯基磷酸、3-三氯甲基苯基磷酸、3-三溴甲基苯基磷酸、3-三碘甲基苯基磷酸、4-三氟甲基苯基磷酸、4-三氯甲基苯基磷酸、4-三溴甲基苯基磷酸、4-三碘甲基苯基磷酸、2,6-雙(三氟甲基)苯基磷酸、2,6-雙(三氯甲基)苯基磷酸、2,6-雙(三溴甲基)苯基磷酸、2,6-雙(三碘甲基)苯基磷酸、3,5-雙(三氟甲基)苯基磷酸、3,5-雙(三氯甲基)苯基磷酸、3,5-雙(三溴甲基)苯基磷酸、3,5-雙(三碘甲基)苯基磷酸、4-全氟乙烯基苯基磷酸等,但不限定於此等。
作為鹵化芳香族磷酸之具體例,可列舉:2-氟苯基磷酸、3-氟苯基磷酸、4-氟苯基磷酸、2-氯苯基磷酸、3-氯苯基磷酸、4-氯苯基磷酸、2-溴苯基磷酸、3-溴苯基磷酸、4-溴苯基磷酸、2-碘苯基磷酸、4-碘苯基磷酸、2,4-二氟苯基磷酸、2,6-二氟苯基磷酸、2,4-二氯苯基磷酸、2,6-二氯苯基磷酸、2,4-二溴苯基磷酸、2,6-二溴苯基磷酸、2,4-二碘苯基磷酸、2,6-二碘苯基磷酸、2,4,6-三氟苯基磷酸、3,4,5-三氟苯基磷酸、2,4,6-三氯苯基磷酸、3,4,5-三氯苯基磷酸、2,4,6-三溴苯基磷酸、3,4,5-三溴苯基磷酸、2,4,6-三碘苯基磷酸、3,4,5-三碘苯基磷酸、五氟苯基磷酸、五氯苯基磷酸、五溴苯基磷酸、五碘苯基磷酸、氟萘基磷酸、氯萘基磷酸、溴萘基磷酸、碘萘基磷酸、氟蒽基磷酸、氯蒽基磷酸、溴蒽基磷酸、碘蒽基磷酸等,但不限定於此等。
飽和脂肪族磷酸,係烷或環烷化合物之至少一個氫原子被磷酸基取代者,構成該種烷或環烷化合物之碳原子數,不特別限定,一般為1~10,較佳為1~5,再更佳為1~3;該烷化合物,亦可經氟等鹵原子、苯基等芳基等之取代基取代,一般該取代基之數量為0~3。
作為飽和脂肪族磷酸,典型地,可列舉:無取代飽和脂肪族磷酸、鹵化飽和脂肪族磷酸、芳基飽和脂肪族磷酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代飽和脂肪族磷酸、鹵化飽和脂肪族磷酸。
作為無取代飽和脂肪族磷酸之具體例,可列舉:甲基磷酸、乙基磷酸等,但不限定於此等。
作為鹵化飽和脂肪族磷酸之具體例,可列舉:三氟甲基磷酸、五氟乙基磷酸等,但不限定於此等。
作為芳基飽和脂肪族磷酸之具體例,可列舉:苯甲基磷酸、二苯甲基磷酸、三苯甲基磷酸、1-苯乙基磷酸、2-苯乙基磷酸等,但不限定於此等。
不飽和脂肪族磷酸,係烯或炔化合物之至少一個氫原子被磷酸基取代者,構成該種烯或炔化合物之碳原子數,不特別限定,一般為2~10,較佳為2~5,再更佳為2~3;烯或炔化合物,亦可經氟等鹵原子、苯基等芳基等之取代基取代,一般該取代基之數量為0~3。
作為不飽和脂肪族磷酸,典型地,可列舉:無取代不飽和脂肪族磷酸、鹵化不飽和脂肪族磷酸、芳基不飽和脂肪族磷酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代不飽和脂肪族磷酸。
作為無取代不飽和脂肪族磷酸之具體例,可列舉:乙烯基磷酸、2-丙烯-1-磷酸、1-丁烯-1-磷酸、3-丁烯-1-磷酸等,但不限定於此等。
本發明較佳之一態樣中,作為含羧基之有機酸,可列舉例如:甲酸及草酸,以及芳香族羧酸、飽和脂肪族羧酸、不飽和脂肪族羧酸等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為芳香族羧酸、不飽和脂肪族羧酸。
芳香族羧酸,係芳香族化合物之至少一個氫原子被羧基取代者,構成該種芳香族化合物之芳香環之碳原子數,不特別限定,一般為6~20,較佳為6~14,再更佳為6~10;該芳香環,亦可經氟等鹵原子、甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基等烷基、乙烯基等烯基、三氟甲基等鹵化烷基、全氟乙烯基等鹵化烯基等之取代基取代,一般該取代基之數量為0~3。
此外,羧基之數量,不特別限定,一般為1~3,較佳為1~2,再更佳為1。
作為芳香族羧酸,典型地,可列舉:無取代芳香族羧酸、烷基或烯基芳香族羧酸、鹵化烷基或鹵化烯基芳香族羧酸、鹵化芳香族羧酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代芳香族羧酸、烷基芳香族羧酸。
作為無取代芳香族羧酸之具體例,可列舉:苯甲酸、苯-1,2-二甲酸、苯-1,3-二甲酸、苯-1,4-二甲酸、苯-1,3,5-三甲酸、2-萘甲酸、蒽甲酸、萘-1,4-二甲酸、萘-1,4-甲酸、菲甲酸、芘甲酸等,但不限定於此等。
作為烷基或烯基芳香族羧酸之具體例,可列舉:鄰甲苯甲酸、間甲苯甲酸、對甲苯甲酸、對乙烯苯甲酸、對異丙基苯甲酸、對十二基苯甲酸、二己基苯甲酸、2,5-二己基苯甲酸、3,5-雙(三級丁基)苯甲酸、3,5-雙(異丙基)苯甲酸、2,4,6-三(三級丁基)苯甲酸、2,4,6-三(異丙基)苯甲酸、5,8-二丁基-2-萘甲酸、6,7-二丁基-2-萘甲酸、己基萘甲酸、4-己基-1-萘甲酸、7-己基-1-萘甲酸、6-己基-2-萘甲酸、辛基萘甲酸、2-辛基-1-萘甲酸、二壬基萘甲酸、2,7-二壬基-4-萘甲酸、二壬基萘二甲酸、十二基萘甲酸、3-十二基-2-萘甲酸等,但不限定於此等。
作為鹵化烷基或鹵化烯基芳香族羧酸之具體例,可列舉:2-三氟甲基苯甲酸、2-三氯甲基苯甲酸、2-三溴甲基苯甲酸、2-三碘甲基苯甲酸、3-三氟甲基苯甲酸、3-三氯甲基苯甲酸、3-三溴甲基苯甲酸、3-三碘甲基苯甲酸、4-三氟甲基苯甲酸、4-三氯甲基苯甲酸、4-三溴甲基苯甲酸、4-三碘甲基苯甲酸、2,6-雙(三氟甲基)苯甲酸、2,6-雙(三氯甲基)苯甲酸、2,6-雙(三溴甲基)苯甲酸、2,6-雙(三碘甲基)苯甲酸、3,5-雙(三氟甲基)苯甲酸、3,5-雙(三氯甲基)苯甲酸、3,5-雙(三溴甲基)苯甲酸、3,5-雙(三碘甲基)苯甲酸、4-全氟乙烯基苯甲酸等,但不限定於此等。
作為鹵化芳香族羧酸之具體例,可列舉:2-氟苯甲酸、3-氟苯甲酸、4-氟苯甲酸、2-氯苯甲酸、3-氯苯甲酸、4-氯苯甲酸、2-溴苯甲酸、3-溴苯甲酸、4-溴苯甲酸、2-碘苯甲酸、4-碘苯甲酸、2,4-二氟苯甲酸、2,6-二氟苯甲酸、2,4-二氯苯甲酸、2,6-二氯苯甲酸、2,4-二溴苯甲酸、2,6-二溴苯甲酸、2,4-二碘苯甲酸、2,6-二碘苯甲酸、2,4,6-三氟苯甲酸、3,4,5-三氟苯甲酸、2,4,6-三氯苯甲酸、3,4,5-三氯苯甲酸、2,4,6-三溴苯甲酸、3,4,5-三溴苯甲酸、2,4,6-三碘苯甲酸、3,4,5-三碘苯甲酸、五氟苯甲酸、五氯苯甲酸、五溴苯甲酸、五碘苯甲酸、氟萘甲酸、氯萘甲酸、溴萘甲酸、碘萘甲酸、氟蒽甲酸、氯蒽甲酸、溴蒽甲酸、碘蒽甲酸等,但不限定於此等。
由再現性佳地實現優異光阻特性之觀點而言,芳香族羧酸之芳香環之取代基為鹵原子之情況下,較佳為氟原子;為烷基之情況下,較佳為碳原子數1~3之烷基,更佳為甲基或乙基,再更佳為甲基。
飽和脂肪族羧酸,係烷或環烷化合物之至少一個氫原子被羧基取代者,構成該種烷或環烷化合物之碳原子數,不特別限定,一般為1~10,較佳為1~5,再更佳為1~3;該烷化合物,亦可經氟等鹵原子、苯基等芳基等之取代基取代,一般該取代基之數量為0~3。
作為飽和脂肪族羧酸,典型地,可列舉:無取代飽和脂肪族羧酸、鹵化飽和脂肪族羧酸、羥基飽和脂肪族羧酸、芳基飽和脂肪族羧酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物容易取得性之觀點等而言,較佳為無取代飽和脂肪族羧酸、鹵化飽和脂肪族羧酸,更佳為鹵化飽和脂肪族羧酸。
作為無取代脂肪族羧酸之具體例,可列舉:甲烷甲酸、甲烷二甲酸(丙二酸)、乙烷甲酸、乙烷-1,1-二甲酸、乙烷-1,2-二甲酸(丁二酸)、丙烷甲酸、丙烷-1,1-二甲酸、丙烷-1,2-二甲酸、丙烷-2,2-二甲酸、丙烷-1,3-二甲酸(戊二酸)、丁烷甲酸、丁烷-1,1-二甲酸、丁烷-1,2-二甲酸、丁烷-1,3-二甲酸、丁烷-1,4-二甲酸(己二酸)、丁烷-2,2-二甲酸、丁烷-2,3-二甲酸、丁烷-2,4-二甲酸、戊烷甲酸、己烷甲酸、庚烷甲酸、辛烷甲酸、壬烷甲酸、癸烷甲酸、十一烷甲酸、十二烷甲酸、十三烷甲酸、十四烷甲酸、十五烷甲酸、十六烷甲酸、十七烷甲酸、十八烷甲酸、十九烷甲酸、二十烷甲酸、二十一烷甲酸、二十二烷甲酸、二十三烷甲酸、二十四烷甲酸等鏈狀或支鏈狀烷羧酸、樟腦甲酸等環烷羧酸等,但不限定於此等。
作為鹵化飽和脂肪族羧酸之具體例,可列舉:氟甲烷甲酸、二氟甲烷甲酸、三氟甲烷甲酸、氯甲烷甲酸、二氯甲烷甲酸、三氯甲烷甲酸、溴甲烷甲酸、二溴甲烷甲酸、三溴甲烷甲酸、碘甲烷甲酸、二碘甲烷甲酸、三碘甲烷甲酸、氟乙烷甲酸、二氟乙烷甲酸、三氟乙烷甲酸、五氟乙烷甲酸、氯乙烷甲酸、二氯乙烷甲酸、三氯乙烷甲酸、五氯乙烷甲酸、三溴乙烷甲酸、五溴乙烷甲酸、三碘乙烷甲酸、五碘乙烷甲酸、氟丙烷甲酸、三氟丙烷甲酸、七氟丙烷甲酸、氯丙烷甲酸、三氯丙烷甲酸、七氯丙烷甲酸、溴丙烷甲酸、三溴丙烷甲酸、七溴丙烷甲酸、三碘丙烷甲酸、七碘丙烷甲酸、三氟丁烷甲酸、九氟丁烷甲酸、三氯丁烷甲酸、九氯丁烷甲酸、三溴丁烷甲酸、九溴丁烷甲酸、三碘丁烷甲酸、九碘丁烷甲酸、三氟戊烷甲酸、全氟戊烷甲酸、三氯戊烷甲酸、全氯戊烷甲酸、三溴戊烷甲酸、全溴戊烷甲酸、三碘戊烷甲酸、全碘戊烷甲酸、三氟己烷甲酸、全氟己烷甲酸、三氯己烷甲酸、全氯己烷甲酸、全溴己烷甲酸、全碘己烷甲酸、三氟庚烷甲酸、全氟庚烷甲酸、三氯庚烷甲酸、全氯庚烷甲酸、全溴庚烷甲酸、全碘庚烷甲酸、三氟辛烷甲酸、全氟辛烷甲酸、三氯辛烷甲酸、全氯辛烷甲酸、全溴辛烷甲酸、全碘辛烷甲酸、三氟壬烷甲酸、全氟壬烷甲酸、三氯壬烷甲酸、全氯壬烷甲酸、全溴壬烷甲酸、全碘壬烷甲酸、三氟癸烷甲酸、全氟癸烷甲酸、三氯癸烷甲酸、全氯癸烷甲酸、全溴癸烷甲酸、全碘癸烷甲酸、三氟十一烷甲酸、全氟十一烷甲酸、三氯十一烷甲酸、全氯十一烷甲酸、全溴十一烷甲酸、全碘十一烷甲酸、三氟十二烷甲酸、全氟十二烷甲酸、三氯十二烷甲酸、全氯十二烷甲酸、全溴十二烷甲酸、全碘十二烷甲酸、三氟十三烷甲酸、全氟十三烷甲酸、三氯十三烷甲酸、全氯十三烷甲酸、全溴十三烷甲酸、全碘十三烷甲酸、三氟十四烷甲酸、全氟十四烷甲酸、三氯十四烷甲酸、全氯十四烷甲酸、全溴十四烷甲酸、全碘十四烷甲酸、三氟十五烷甲酸、全氟十五烷甲酸、三氯十五烷甲酸、全氯十五烷甲酸、全溴十五烷甲酸、全碘十五烷甲酸、全氟十六烷甲酸、全氯十六烷甲酸、全溴十六烷甲酸、全碘十六烷甲酸、全氟十七烷甲酸、全氯十七烷甲酸、全溴十七烷甲酸、全碘十七烷甲酸、全氟十八烷甲酸、全氯十八烷甲酸、全溴十八烷甲酸、全碘十八烷甲酸、全氟十九烷甲酸、全氯十九烷甲酸、全溴十九烷甲酸、全碘十九烷甲酸、全氟二十烷甲酸、全氯二十烷甲酸、全溴二十烷甲酸、全碘二十烷甲酸、全氟二十一烷甲酸、全氯二十一烷甲酸、全溴二十一烷甲酸、全碘二十一烷甲酸、全氟二十二烷甲酸、全氯二十二烷甲酸、全溴二十二烷甲酸、全碘二十二烷甲酸、全氟二十三烷甲酸、全氯二十三烷甲酸、全溴二十三烷甲酸、全碘二十三烷甲酸、全氟二十四烷甲酸、全氯二十四烷甲酸、全溴二十四烷甲酸、全碘二十四烷甲酸等,但不限定於此等。
作為羥基飽和脂肪族羧酸之具體例,可列舉:1,2-二羥基乙烷-1,2-二甲酸(酒石酸)、2-羥基丙烷-1,2,3-三甲酸(檸檬酸)等,但不限定於此等。
作為芳基飽和脂肪族羧酸之具體例,可列舉:苯基甲烷甲酸、二苯基甲烷甲酸、三苯基甲烷甲酸、1-苯基乙烷甲酸、2-苯基乙烷甲酸等,但不限定於此等。
由再現性佳地實現優異光阻特性之觀點而言,在飽和脂肪族羧酸之烷基上進行取代之取代基為鹵原子之情況下,較佳為氟原子;為芳基之情況下,較佳為碳原子數6~10之芳基,更佳為苯基。
不飽和脂肪族羧酸,係烯或炔化合物之至少一個氫原子被羧酸基取代者,構成該種烯或炔化合物之碳原子數,不特別限定,一般為2~10,較佳為2~5,再更佳為2~3;烯或炔化合物,亦可經氟等鹵原子、苯基等芳基等之取代基取代,一般該取代基之數量為0~3。
作為不飽和脂肪族羧酸,典型地,可列舉:無取代不飽和脂肪族羧酸、鹵化不飽和脂肪族羧酸、芳基不飽和脂肪族羧酸等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代不飽和脂肪族羧酸。
作為無取代不飽和脂肪族羧酸之具體例,可列舉:乙烯甲酸、2-丙烯-1-甲酸、1-丁烯-1-甲酸、3-丁烯-1-甲酸、反式乙烯-1,2-二甲酸(富馬酸)、順式乙烯-1,2-二甲酸(馬來酸)等,但不限定於此等。
本發明較佳之一態樣中,作為含酚性羥基之有機酸,可列舉:羥基芳香族化合物。
羥基芳香族化合物,係芳香族化合物之至少一個氫原子被羥基取代者,構成該種芳香族化合物之芳香環之碳原子數,不特別限定,一般為6~20,較佳為6~14,再更佳為6~10;該芳香環,亦可經氟等鹵原子、甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基等烷基、乙烯基等烯基、三氟甲基等鹵化烷基、全氟乙烯基等鹵化烯基等之取代基取代,一般該取代基之數量為0~3。
此外,羥基之數量,不特別限定,一般為1~3,較佳為1~2,再更佳為1。
作為羥基芳香族化合物,典型地,可列舉:無取代羥基芳香族化合物、烷基或烯基羥基芳香族化合物、鹵化烷基或鹵化烯基羥基芳香族化合物、鹵化羥基芳香族化合物等,但不限定於此等。
其中,由再現性佳地實現優異微影特性之觀點、化合物之容易取得性之觀點等而言,較佳為無取代羥基芳香族化合物。
作為無取代羥基芳香族化合物之具體例,可列舉:酚、1,2-二羥基苯、1,3-二羥基苯、1,4-二羥基苯、1,3,5-三羥基苯、2-羥基萘、羥基蒽、羥基菲、羥基芘等,但不限定於此等。
作為烷基或烯基羥基芳香族化合物之具體例,可列舉:2,5-二羥基甲苯、對羥基苯乙烯、1-異丙基-4-羥基苯、1-十二基-4-羥基苯等,但不限定於此等。
作為鹵化烷基或鹵化烯基羥基芳香族化合物之具體例,可列舉:2-三氟甲基酚、2-三氯甲基酚、2-三溴甲基酚、2-三碘甲基酚、3-三氟甲基酚、3-三氯甲基酚、3-三溴甲基酚、3-三碘甲基酚、4-三氟甲基酚、4-三氯甲基酚、4-三溴甲基酚、4-三碘甲基酚、2,6-雙(三氟甲基)酚、2,6-雙(三氯甲基)酚、2,6-雙(三溴甲基)酚、2,6-雙(三碘甲基)酚、3,5-雙(三氟甲基)酚、3,5-雙(三氯甲基)酚、3,5-雙(三溴甲基)酚、3,5-雙(三碘甲基)酚、4-全氟乙烯基酚等,但不限定於此等。
作為鹵化羥基芳香族化合物之具體例,可列舉:2-氟酚、3-氟酚、4-氟酚、2-氯酚、3-氯酚、4-氯酚、2-溴酚、3-溴酚、4-溴酚、2-碘酚、4-碘酚、2,4-二氟酚、2,6-二氟酚、2,4-二氯酚、2,6-二氯酚、2,4-二溴酚、2,6-二溴酚、2,4-二碘酚、2,6-二碘酚、2,4,6-三氟酚、3,4,5-三氟酚、2,4,6-三氯酚、3,4,5-三氯酚、2,4,6-三溴酚、3,4,5-三溴酚、2,4,6-三碘酚、3,4,5-三碘酚、五氟酚、五氯酚、五溴酚、五碘酚、氟羥基萘、氯羥基萘、溴羥基萘、羥基碘萘、氟羥基蒽、氯羥基蒽、溴羥基蒽、羥基碘蒽等,但不限定於此等。
此外,作為本發明較佳之有機酸,亦可列舉:三角酸、方酸、玫棕酸等側氧碳酸。
本發明之某一態樣中,由再現性更佳地獲得優異微影特性之觀點而言,上述二種以上酸性化合物,較佳為含有選自硝酸、硫酸、側氧碳酸、含磺酸基之有機酸及含羧基之有機酸所成群中相異之二種以上;更佳為含有各別選自硝酸、側氧碳酸、含磺酸基之有機酸及含羧基之有機酸所成群中相異之二種以上。
此外,在其他態樣中,由再現性更佳地實現優異微影特性之觀點而言,上述二種以上酸性化合物,較佳為含有選自硫酸及含磺酸基之有機酸所成群中至少一種、及選自鹽酸、硝酸、磷酸、硼酸、雜多酸、側氧碳酸、含磷酸基之有機酸、含羧基之有機酸及含酚性羥基之有機酸所成群中至少一種;更佳為含有含磺酸基之有機酸、及選自硝酸、側氧碳酸及含羧基之有機酸所成群中至少一種。
本發明之膜形成用組成物所含之水解縮合物,係藉由使用上述說明之酸性化合物將含有上述說明之式(1)所表示之含胺基之矽烷之水解性矽烷化合物進行水解及縮合而獲得者,而藉由使用該含胺基之矽烷及二種以上酸性化合物,作為水解縮合物之由該含胺基之矽烷衍生之單體單元,可實現含有二種以上胺鹽結構之單元,其結果,可實現對形成為上層之光阻膜用組成物之溶劑的耐性、對氟系氣體之良好蝕刻特性及良好微影特性。
特別地,硝酸、羧酸系化合物及酚系化合物,能夠特別地有助於微影特性之提升;硫酸、磺酸系化合物、磷酸系化合物,能夠特別地有助於對氟系氣體之蝕刻特性、濕蝕刻特性之提升。
本發明中,在製造水解縮合物時所使用之酸性化合物之數量,只要為2以上則不特別限定,但由再現性佳地實現優異微影特性之觀點而言,一般為2~5,較佳為2~4,更佳為2~3,再進一步更佳為2。
本發明之膜形成用組成物,含有溶劑。
此種溶劑,只要溶解上述及下述水解性矽烷、其水解縮合物及其他成分,則沒有限制。
作為其具體例,可列舉:乙酸甲賽璐蘇、乙酸乙賽璐蘇、丙二醇、丙二醇單甲醚、丙二醇單乙醚、甲基異丁基甲醇、丙二醇單丁醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、丙二醇單丁醚乙酸酯、甲苯、二甲苯、甲基乙基酮、環戊酮、環己酮、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-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、乙二醇單甲醚、乙二醇單乙醚、乙二醇單丙醚、乙二醇單丁醚、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二丙醚、二乙二醇二丁醚、丙二醇單甲醚、丙二醇二甲醚、丙二醇二乙醚、丙二醇二丙醚、丙二醇二丁醚、乳酸乙酯、乳酸丙酯、乳酸異丙酯、乳酸丁酯、乳酸異丁酯、甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸異丙酯、甲酸丁酯、甲酸異丁酯、甲酸戊酯、甲酸異戊酯、乙酸甲酯、乙酸乙酯、乙酸戊酯、乙酸異戊酯、乙酸己酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、丙酸丁酯、丙酸異丁酯、丁酸甲酯、丁酸乙酯、丁酸丙酯、丁酸異丙酯、丁酸丁酯、丁酸異丁酯、羥基乙酸乙酯、2-羥基-2-甲基丙酸乙酯、3-甲氧基-2-甲基丙酸甲酯、2-羥基-3-甲基丁酸甲酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸乙酯、乙酸3-甲氧基丁酯、乙酸3-甲氧基丙酯、乙酸3-甲基-3-甲氧基丁酯、丙酸3-甲基-3-甲氧基丁酯、丁酸3-甲基-3-甲氧基丁酯、乙醯乙酸甲酯、甲苯、二甲苯、甲基乙基酮、甲基丙基酮、甲基丁基酮、2-庚酮、3-庚酮、4-庚酮、環己酮、N,N-二甲基甲醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮、4-甲基-2-戊醇、γ-丁內酯等,溶劑可單獨使用一種或組合使用二種以上。
本發明之膜形成用組成物,亦可含有水作為溶劑,其含量,相對於該組成物所含之溶劑,較佳為30質量%以下,更佳為20質量%以下,再更佳為15質量%以下。
本發明中,上述水解性矽烷,亦可含有於分子內具有鎓基之水解性有機矽烷。藉由使用於分子內具有鎓基之水解性有機矽烷,從而可有效且有效率地促進水解性矽烷之交聯反應。
此種於分子內具有鎓基之水解性有機矽烷之較佳的一例,以下述式(4)表示。
R31
係與矽原子鍵結之基團,互相獨立地為鎓基或含有其之有機基;R32
係與矽原子鍵結之基團,表示可經取代之烷基、可經取代之芳基、可經取代之芳烷基、可經取代之鹵化烷基、可經取代之鹵化芳基、可經取代之鹵化芳烷基、可經取代之烷氧烷基、可經取代之烷氧芳基、可經取代之烷氧芳烷基、或可經取代之烯基,或者為含有環氧基、丙烯醯基、甲基丙烯醯基、巰基、胺基或氰基之有機基;R33
互相獨立地為與矽原子鍵結之基團或原子,為烷氧基、芳烷氧基、醯氧基、或鹵原子;j係表示1或2,k係表示0或1,並滿足1≦j+k≦2。
作為此種烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烷氧烷基、烷氧芳基、烷氧芳烷基、烯基、烷氧基、鹵原子及含有環氧基、丙烯醯基、甲基丙烯醯基、巰基、胺基或氰基之有機基,以及烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烷氧烷基、烷氧芳基、烷氧芳烷基及烯基之取代基之具體例及其等之較佳碳原子數,可列舉與上述相同者。
若進一步詳細說明,作為鎓基之具體例,可列舉環狀銨基或鏈狀銨基,較佳為三級銨基或四級銨基。
亦即,作為鎓基或含有其之有機基之較佳具體例,可列舉:環狀銨基或鏈狀銨基或含有此等之至少一者之有機基,較佳為三級銨基或四級銨基或含有此等之至少一者之有機基。
再者,鎓基為環狀銨基之情況下,構成銨基之氮原子同時為構成環之原子。此時,有構成環之氮原子與矽原子直接或經由2價連結基鍵結之情況,以及構成環之碳原子與矽原子直接或經由2價連結基鍵結之情況。
本發明較佳態樣之一例中,R31
為下述式(S1)所表示之雜芳香族環狀銨基。
A1
、A2
、A3
及A4
,互相獨立地表示下述式(J1)~(J3)之任一者所表示之基團,而A1
~A4
中至少一個為下述式(J2)所表示之基團;根據式(4)之矽原子與A1
~A4
之哪一者鍵結,來決定各個A1
~A4
、與各別鄰接於其等而共同構成環之原子之間之鍵結為單鍵或雙鍵,使構成之環顯示芳香族性。
R30
係互相獨立地表示單鍵、氫原子、烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基或烯基;作為烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基及烯基之具體例及其等之較佳碳原子數,可列舉與上述相同者。
R34
係互相獨立地表示烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基或羥基;R34
存在二個以上之情況下,二個R34
可互相鍵結形成環,二個R34
形成之環可為交聯環結構,此種情況下,環狀銨基將具有金剛烷環、降莰烯環、螺環等。
作為此種烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基及烯基之具體例及其等之較佳碳原子數,可列舉與上述相同者。
n1
為1~8之整數,m1
為0或1,m2
為0或從1到可在單環或多環上進行取代之最大數之正整數。
m1
為0之情況下,構成含有A1
~A4
之(4+n1
)元環。亦即,各別於n1
為1時構成5元環,n1
為2時構成6元環,n1
為3時構成7元環,n1
為4時構成8元環,n1
為5時構成9元環,n1
為6時構成10元環,n1
為7時構成11元環,n1
為8時構成12元環。
m1
為1之情況下,形成含有A1
~A3
之(4+n1
)元環與含有A4
之6元環縮合之縮合環。
A1
~A4
,根據其為式(J1)~(J3)哪一者,有在構成環之原子上具有氫原子之情況、及不具有氫原子之情況;A1
~A4
在構成環之原子上具有氫原子之情況下,其氫原子可取代為R34
。此外,R34
亦可在A1
~A4
中之環構成原子以外之環構成原子上進行取代。由於此種情事,如上所述,m2
為選自0或從1到可在單環或多環上進行取代之最大數之整數。
式(S1)所表示之雜芳香族環狀銨基之鍵結鍵,存在於此種單環或縮合環中存在之任意碳原子或氮原子,並與矽原子直接鍵結,或者與連結基鍵結而構成含有環狀銨之有機基,其再與矽原子鍵結。
作為此種連結基,可列舉:伸烷基、伸芳基、伸烯基等,但不限定於此等。
作為伸烷基及伸芳基之具體例及其等之較佳碳原子數,可列舉與上述相同者。
伸烯基,係將烯基進一步移除一個氫原子而衍生之2價的基團,作為此種烯基之具體例,可列舉與上述相同者。
伸烯基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下。
作為其具體例,可列舉:伸乙烯基、1-甲基伸乙烯基、伸丙烯基、1-伸丁烯基、2-伸丁烯基、1-伸戊烯基、2-伸戊烯基等,但不限定於此等。
A5
、A6
、A7
及A8
,互相獨立地表示下述式(J4)~(J6)之任一者所表示之基團,而A5
~A8
中至少一個為下述式(J5)所表示之基團;根據式(4)之矽原子與A5
~A8
之哪一者鍵結,來決定各個A5
~A8
、與各別鄰接於其等而共同構成環之原子之間之鍵結為單鍵或雙鍵,使構成之環顯示非芳香族性。
R30
係互相獨立地表示單鍵、氫原子、烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基或烯基;作為烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基及烯基之具體例及其等之較佳碳原子數,可列舉與上述相同者。
R35
係互相獨立地表示烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烯基或羥基;R35
存在二個以上之情況下,二個R35
可互相鍵結形成環,二個R35
形成之環可為交聯環結構,此種情況下,環狀銨基將具有金剛烷環、降莰烯環、螺環等。
作為此種烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基及烯基之具體例及其等之較佳碳原子數,可列舉與上述相同者。
n2
為1~8之整數,m3
為0或1,m4
為0或從1到可在單環或多環上進行取代之最大數之正整數。
m3
為0之情況下,構成含有A5
~A8
之(4+n2
)元環。亦即,各別於n2
為1時構成5元環,n2
為2時構成6元環,n2
為3時構成7元環,n2
為4時構成8元環,n2
為5時構成9元環,n2
為6時構成10元環,n2
為7時構成11元環,n2
為8時構成12元環。
m3
為1之情況下,形成含有A5
~A7
之(4+n2
)元環與含有A8
之6元環縮合之縮合環。
A5
~A8
,根據為式(J4)~(J6)哪一者,有在構成環之原子上具有氫原子之情況、及不具有氫原子之情況;A5
~A8
在構成環之原子上具有氫原子之情況下,其氫原子可取代為R35
。此外,R35
亦可在A5
~A8
中之環構成原子以外之環構成原子上進行取代。
由於此種情事,如上所述,m4
為選自0或從1到可在單環或多環上進行取代之最大數之整數。
式(S2)所表示之雜脂肪族環狀銨基之鍵結鍵,存在於此種單環或縮合環中存在之任意碳原子或氮原子,並與矽原子直接鍵結,或者與連結基鍵結而構成含有環狀銨之有機基,其再與矽原子鍵結。
作為此種連結基,可列舉伸烷基、伸芳基或伸烯基;作為伸烷基、伸芳基及伸烯基之具體例及其等之較佳碳原子數,可列舉與上述相同者。
R30
係互相獨立地表示氫原子、烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基或烯基;作為烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基及烯基之具體例及其等之較佳碳原子數,可列舉與上述相同者。
式(S3)所表示之鏈狀銨基,係與矽原子直接鍵結,或者與連結基鍵結而構成含有鏈狀銨基之有機基,其再與矽原子鍵結。
作為此種連結基,可列舉伸烷基、伸芳基或伸烯基;作為伸烷基、伸芳基及伸烯基之具體例,可列舉與上述相同者。
本發明之膜形成用組成物,亦可進一步含有具有磺基之矽烷、具有磺醯胺基之矽烷作為水解性矽烷。
以下,列舉其具體例,但不限定於此等。
本發明中,上述水解性矽烷化合物,亦可含有於分子內具有環狀尿素骨架之水解性有機矽烷,作為具體例,並非限定於此,但可列舉下述式(5-1)所表示之水解性有機矽烷。
式(5-1)中,R501
係與矽原子鍵結之基團,互相獨立地表示式(5-2)所表示之基團;R502
係與矽原子鍵結之基團,表示可經取代之烷基、可經取代之芳基、可經取代之芳烷基、可經取代之鹵化烷基、可經取代之鹵化芳基、可經取代之鹵化芳烷基、可經取代之烷氧烷基、可經取代之烷氧芳基、可經取代之烷氧芳烷基、或可經取代之烯基,或者表示含有環氧基、丙烯醯基、甲基丙烯醯基、巰基或氰基之有機基;R503
係與矽原子鍵結之基團或原子,互相獨立地表示烷氧基、芳烷氧基、醯氧基或鹵原子;x係1或2,y係0或1,並滿足x+y≦2;R502
之烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烷氧烷基、烷氧芳基、烷氧芳烷基、烯基、及含有環氧基、丙烯醯基、甲基丙烯醯基、巰基或氰基之有機基,以及R503
之烷氧基、芳烷氧基、醯氧基及鹵原子,以及其等之取代基之具體例及較佳碳原子數等,可列舉與上述關於R2
及R3
所述相同者。
式(5-2)中,R504
係互相獨立地表示氫原子、可經取代之烷基、可經取代之烯基、或者含有環氧基或磺醯基之有機基;R50 5
係互相獨立地表示伸烷基、羥基伸烷基、硫鍵(-S-)、醚鍵(-O-)或酯鍵(-CO-O-或-O-CO-)。
再者,R504
之可經取代之烷基、可經取代之烯基及含有環氧基之有機基之具體例及較佳碳原子數等,可列舉與上述關於R2
所述相同者,而此等以外,作為R504
之可經取代之烷基,較佳為末端之氫原子被乙烯基取代之烷基,作為其具體例,可列舉:烯丙基、2-乙烯基乙基、3-乙烯基丙基、4-乙烯基丁基等。
作為含有磺醯基之有機基,只要是含有磺醯基則不特別限定,可列舉:可經取代之烷基磺醯基、可經取代之芳基磺醯基、可經取代之芳烷基磺醯基、可經取代之鹵化烷基磺醯基、可經取代之鹵化芳基磺醯基、可經取代之鹵化芳烷基磺醯基、可經取代之烷氧烷基磺醯基、可經取代之烷氧芳基磺醯基、可經取代之烷氧芳烷基磺醯基、可經取代之烯基磺醯基等;此等基團之烷基、芳基、芳烷基、鹵化烷基、鹵化芳基、鹵化芳烷基、烷氧烷基、烷氧芳基、烷氧芳烷基及烯基以及其等之取代基之具體例及較佳之碳原子數等,可列舉與上述關於R2
所述相同者。
伸烷基,係將上述烷基進一步移除一個氫原子而衍生之2價之基團,可為直鏈狀、支鏈狀、環狀之任一者,作為此種伸烷基之具體例,可列舉與上述相同者。伸烷基之碳原子數,不特別限定,較佳為40以下,更佳為30以下,再更佳為20以下,再進一步更佳為10以下。
此外,R505
之伸烷基,亦可在其末端或中間,較佳為在中間,具有選自硫鍵、醚鍵及酯鍵之一種或二種以上。
作為伸烷基之具體例,可列舉:亞甲基、伸乙基、三亞甲基、甲基伸乙基、四亞甲基、五亞甲基、六亞甲基、七亞甲基、八亞甲基、九亞甲基、十亞甲基等直鏈狀伸烷基;1-甲基三亞甲基、2-甲基三亞甲基、1,1-二甲基伸乙基、1-甲基四亞甲基、2-甲基四亞甲基、1,1-二甲基三亞甲基、1,2-二甲基三亞甲基、2,2-二甲基三亞甲基、1-乙基三亞甲基等支鏈狀伸烷基;1,2-環丙二基、1,2-環丁二基、1,3-環丁二基、1,2-環己二基、1,3-環己二基等環狀伸烷基等;含有-CH2
OCH2
-、-CH2
CH2
OCH2
-、-CH2
CH2
OCH2
CH2
-、-CH2
CH2
CH2
OCH2
CH2
-、-CH2
CH2
OCH2
CH2
CH2
-、-CH2
CH2
CH2
OCH2
CH2
CH2
-、-CH2
SCH2
-、-CH2
CH2
SCH2
-、-CH2
CH2
SCH2
CH2
-、-CH2
CH2
CH2
SCH2
CH2
-、-CH2
CH2
SCH2
CH2
CH2
-、-CH2
CH2
CH2
SCH2
CH2
CH2
-、-CH2
OCH2
CH2
SCH2
-等醚基等之伸烷基,但不限定於此等。
羥基伸烷基,係將上述伸烷基之至少一個氫原子取代為羥基者,作為其具體例,可列舉:羥基亞甲基、1-羥基伸乙基、2-羥基伸乙基、1,2-二羥基伸乙基、1-羥基三亞甲基、2-羥基三亞甲基、3-羥基三亞甲基、1-羥基四亞甲基、2-羥基四亞甲基、3-羥基四亞甲基、4-羥基四亞甲基、1,2-二羥基四亞甲基、1,3-二羥基四亞甲基、1,4-二羥基四亞甲基、2,3-二羥基四亞甲基、2,4-二羥基四亞甲基、4,4-二羥基四亞甲基等,但不限定於此等。
式(5-2)中,X501
係互相獨立地表示下述式(5-3)至(5-5)所表示之基團,同時下述式(5-4)及(5-5)之酮基之碳原子,與式(5-2)中R505
所鍵結之氮原子鍵結。
式(5-3)至(5-5)中,R506
至R510
,互相獨立地表示氫原子或可經取代之烷基、可經取代之烯基、或者含有環氧基或磺醯基之有機基;可經取代之烷基、可經取代之烯基及含有環氧基或磺醯基之有機基之具體例及較佳之碳原子數等,可列舉與上述關於R504
所述相同者。
其中,由再現性佳地實現優異微影特性之觀點而言,較佳為式(5-5)所表示之基團。
由再現性佳地實現優異微影特性之觀點而言,較佳為R504
及R506
至R510
之至少一個係末端之氫原子被乙烯基取代之烷基。
上述式(5-1)所表示之水解性有機矽烷,可使用市售品,亦可以國際公開第2011/102470號等所記載之習知方法合成。
本發明之較佳一態樣中,本發明之膜形成用組成物所含之水解縮合物係含有:在使用式(1)所表示之含胺基之矽烷的同時至少使用式(2)所表示之其他矽烷而獲得之水解縮合物;本發明之其他較佳一態樣中,本發明之膜形成用組成物所含之水解縮合物係含有:在使用式(1)所表示之含胺基之矽烷的同時至少使用式(2)所表示之其他矽烷及式(5-1)所表示之水解性有機矽烷而獲得之水解縮合物。
本發明之水解縮合物之重量平均分子量,一般為500~1,000,000,但由抑制組成物中之水解縮合物析出等之觀點等而言,較佳為500,000以下,更佳為250,000以下,再更佳為100,000以下;由兼具保存穩定性及塗佈性之觀點等而言,較佳為700以上,更佳為1,000以上。
再者,重量平均分子量,係藉由凝膠滲透層析(GPC)分析以聚苯乙烯換算所獲得之分子量。GPC分析,例如可使用GPC裝置(商品名HLC-8220GPC,東曹(股)製)、GPC管柱(商品名ShodexKF803L、KF802、KF801,昭和電工(股)製),管柱溫度設為40℃,使用四氫呋喃作為溶離液(溶出溶劑),流量(流速)設為1.0mL/min,並使用聚苯乙烯(昭和電工(股)製)作為標準樣品來進行。
本發明之膜形成用組成物,為了該水解縮合物之穩定化等目的,亦可含有有機酸、水、醇等。
作為本發明之膜形成用組成物為了上述目的可含有之有機酸之具體例,可列舉:草酸、丙二酸、甲基丙二酸、丁二酸、馬來酸、蘋果酸、酒石酸、鄰苯二甲酸、檸檬酸、戊二酸、檸檬酸、乳酸、水楊酸等,但不限定於此等。此等中,較佳為草酸、馬來酸。
本發明之膜形成用組成物含有有機酸之情況下,其含量,相對於水解性矽烷、其水解物及其水解縮合物之合計質量,為0.1質量%~5.0質量%。
本發明之膜形成用組成物為了上述目的可含有之醇,較佳為容易藉由塗佈後之加熱而蒸發者。作為其具體例,可列舉:甲醇、乙醇、丙醇、異丙醇、丁醇等低級脂肪族醇。
本發明之膜形成用組成物含有醇之情況下,其含量,相對於組成物100質量份,為1質量份~20質量份。
本發明之膜形成用組成物,亦可根據需要進一步含有有機聚合物化合物、酸產生劑、界面活性劑等。
本發明之膜形成用組成物可含有之有機聚合物化合物,係根據其添加目的而從各種有機聚合物(縮合聚合聚合物及加成聚合聚合物)中適當選擇者。
作為其具體例,可列舉:聚酯、聚苯乙烯、聚醯亞胺、丙烯酸聚合物、甲基丙烯酸聚合物、聚乙烯醚、苯酚酚醛清漆、萘酚酚醛清漆、聚醚、聚醯胺、聚碳酸酯等加成聚合聚合物及縮合聚合聚合物。
本發明中,含有作為吸光部位發揮功能之苯環、萘環、蒽環、三嗪環、喹啉環、喹㗁啉環等之芳香環或雜芳香環之有機聚合物,在需要該種功能之情況下亦可較合適地使用。作為該種有機聚合物化合物之具體例,可列舉:含有丙烯酸苄酯、甲基丙烯酸苄酯、丙烯酸苯酯、丙烯酸萘酯、甲基丙烯酸蒽酯、甲基丙烯酸蒽甲酯、苯乙烯、羥基苯乙烯、苄基乙烯基醚及N-苯基馬來醯亞胺等加成聚合性單體作為其結構單元之加成聚合聚合物、以及苯酚酚醛清漆及萘酚酚醛清漆等縮合聚合聚合物,但不限定於此等。
使用加成聚合聚合物作為有機聚合物化合物之情況下,該聚合物化合物,可為均聚物、共聚物之任一者。
加成聚合聚合物之製造中使用加成聚合性單體,而作為該種加成聚合性單體之具體例,可列舉:丙烯酸、甲基丙烯酸、丙烯酸酯化合物、甲基丙烯酸酯化合物、丙烯醯胺化合物、甲基丙烯醯胺化合物、乙烯基化合物、苯乙烯化合物、馬來醯亞胺化合物、馬來酸酐、丙烯腈等,但不限定於此等。
作為丙烯酸酯化合物之具體例,可列舉:丙烯酸甲酯、丙烯酸乙酯、丙烯酸正己酯、丙烯酸異丙酯、丙烯酸環己酯、丙烯酸苄酯、丙烯酸苯酯、丙烯酸蒽甲酯、丙烯酸2-羥乙酯、丙烯酸3-氯-2-羥丙酯、丙烯酸2-羥丙酯、丙烯酸2,2,2-三氟乙酯、丙烯酸2,2,2-三氯乙酯、丙烯酸2-溴乙酯、丙烯酸4-羥丁酯、丙烯酸2-甲氧基乙酯、丙烯酸四氫糠酯、丙烯酸2-甲基-2-金剛烷酯、5-丙烯醯氧基-6-羥基降莰烯-2-甲酸-6-內酯、3-丙烯醯氧基丙基三乙氧基矽烷、丙烯酸縮水甘油酯等,但不限定於此等。
作為甲基丙烯酸酯化合物之具體例,可列舉:甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正己酯、甲基丙烯酸異丙酯、甲基丙烯酸環己酯、甲基丙烯酸苄酯、甲基丙烯酸苯酯、甲基丙烯酸蒽甲酯、甲基丙烯酸2-羥乙酯、甲基丙烯酸2-羥丙酯、甲基丙烯酸2,2,2-三氟乙酯、甲基丙烯酸2,2,2-三氯乙酯、甲基丙烯酸2-溴乙酯、甲基丙烯酸4-羥丁酯、甲基丙烯酸2-甲氧基乙酯、甲基丙烯酸四氫糠酯、甲基丙烯酸2-甲基-2-金剛烷酯、5-甲基丙烯醯氧基-6-羥基降莰烯-2-甲酸-6-內酯、3-甲基丙烯醯氧基丙基三乙氧基矽烷、甲基丙烯酸縮水甘油酯、甲基丙烯酸2-苯乙酯、甲基丙烯酸羥苯酯、甲基丙烯酸溴苯酯等,但不限定於此等。
作為丙烯醯胺化合物之具體例,可列舉:丙烯醯胺、N-甲基丙烯醯胺、N-乙基丙烯醯胺、N-苄基丙烯醯胺、N-苯基丙烯醯胺、N,N-二甲基丙烯醯胺、N-蒽基丙烯醯胺等,但不限定於此等。
作為甲基丙烯醯胺化合物之具體例,可列舉:甲基丙烯醯胺、N-甲基甲基丙烯醯胺、N-乙基甲基丙烯醯胺、N-苄基甲基丙烯醯胺、N-苯基甲基丙烯醯胺、N,N-二甲基甲基丙烯醯胺、N-蒽基甲基丙烯醯胺等,但不限定於此等。
作為乙烯基化合物之具體例,可列舉:乙烯醇、2-羥乙基乙烯基醚、甲基乙烯基醚、乙基乙烯基醚、苄基乙烯基醚、乙烯基乙酸、乙烯基三甲氧基矽烷、2-氯乙基乙烯基醚、2-甲氧基乙基乙烯基醚、乙烯基萘、乙烯基蒽等,但不限定於此等。
作為苯乙烯化合物之具體例,可列舉:苯乙烯、羥基苯乙烯、氯苯乙烯、溴苯乙烯、甲氧基苯乙烯、氰基苯乙烯、乙醯基苯乙烯等,但不限定於此等。
作為馬來醯亞胺化合物,可列舉:馬來醯亞胺、N-甲基馬來醯亞胺、N-苯基馬來醯亞胺、N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、N-羥乙基馬來醯亞胺等,但不限定於此等。
使用縮合聚合聚合物作為聚合物之情況下,作為該種聚合物,可列舉例如:二元醇化合物與二羧酸化合物之縮合聚合聚合物。作為二元醇化合物,可列舉:二乙二醇、六亞甲基二醇、丁二醇等。作為二羧酸化合物,可列舉:丁二酸、己二酸、對苯二甲酸、馬來酸酐等。此外,尚可列舉例如:聚均苯四甲酸醯亞胺、聚(對苯二甲醯對苯二胺)、聚對苯二甲酸丁二酯、聚對苯二甲酸乙二酯等聚酯、聚醯胺、聚醯亞胺,但不限定於此等。
有機聚合物化合物含有羥基之情況下,此羥基,可與水解縮合物等進行交聯反應。
本發明之膜形成用組成物可含有之有機聚合物化合物之重量平均分子量,一般為1,000~1,000,000,但由抑制組成物中之析出之觀點等而言,較佳為300,000以下,更佳為200,000以下,再更佳為100,000;由充分獲得作為聚合物之功能之效果之觀點等而言,較佳為3,000以上,更佳為5,000以上,再更佳為10,000以上。
此種有機聚合物化合物,可單獨使用一種或組合使用二種以上。
本發明之膜形成用組成物含有有機聚合物化合物之情況下,其含量,由於係考量該有機聚合物化合物之功能等而適當決定因此無法一概地規定,但一般相對於水解性矽烷之水解縮合物之質量,為1質量%~200質量%之範圍,由抑制組成物中之析出之觀點等而言,較佳為100質量%以下,更佳為50質量%以下,再更佳為30質量%以下;由充分獲得其效果之觀點等而言,較佳為5質量%以上,更佳為10質量%以上,再更佳為30質量%以上。
本發明之膜形成用組成物含有酸產生劑之情況下,作為該酸產生劑,可列舉:熱酸產生劑及光酸產生劑。
作為光酸產生劑,可列舉:鎓鹽化合物、磺醯亞胺化合物、二磺醯基重氮甲烷化合物等,但不限定於此等。
作為鎓鹽化合物之具體例,可列舉:二苯基錪鎓六氟磷酸鹽、二苯基錪鎓三氟甲磺酸鹽、二苯基錪鎓九氟正丁磺酸鹽、二苯基錪鎓全氟正辛磺酸鹽、二苯基錪鎓樟腦磺酸鹽、雙(4-三級丁基苯基)錪鎓樟腦磺酸鹽、雙(4-三級丁基苯基)錪鎓三氟甲磺酸鹽等錪鎓鹽化合物;三苯基鋶六氟銻酸鹽、三苯基鋶九氟正丁磺酸鹽、三苯基鋶樟腦磺酸鹽、三苯基鋶三氟甲磺酸鹽等鋶鹽化合物等,但不限定於此等。
作為磺醯亞胺化合物之具體例,可列舉:N-(三氟甲磺醯氧基)琥珀醯亞胺、N-(九氟正丁磺醯氧基)琥珀醯亞胺、N-(樟腦磺醯氧基)琥珀醯亞胺、N-(三氟甲磺醯氧基)萘二甲醯亞胺等,但不限定於此等。
作為二磺醯基重氮甲烷化合物之具體例,可列舉:雙(三氟甲基磺醯基)重氮甲烷、雙(環己基磺醯基)重氮甲烷、雙(苯磺醯基)重氮甲烷、雙(對甲苯磺醯基)重氮甲烷、雙(2,4-二甲苯磺醯基)重氮甲烷、甲磺醯基-對甲苯磺醯基重氮甲烷等,但不限定於此等。
酸產生劑,可單獨使用一種或組合使用二種以上。
本發明之膜形成用組成物含有酸產生劑之情況下,其含量,由於係考量酸產生劑之種類等而適當設定因此無法一概地規定,一般相對於水解性矽烷之水解縮合物之質量,為0.01質量%~5質量%之範圍,由抑制組成物中之酸產生劑析出之觀點等而言,較佳為3質量%以下,更佳為1質量%以下;由充分獲得其效果之觀點等而言,較佳為0.1質量%以上,更佳為0.5質量%以上。
界面活性劑,特別是在將本發明之膜形成用組成物作為微影用光阻下層膜形成用組成物塗佈於基板時,對抑制針孔、條紋等之產生為有效。
作為此種界面活性劑之具體例,可列舉:聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯十六基醚、聚氧乙烯油基醚等聚氧乙烯烷基醚類;聚氧乙烯辛基酚醚、聚氧乙烯壬基酚醚等聚氧乙烯烷基芳基醚類;聚氧乙烯‧聚氧丙烯嵌段共聚物類;山梨糖醇酐單月桂酸酯、山梨糖醇酐單棕櫚酸酯、山梨糖醇酐單硬脂酸酯、山梨糖醇酐單油酸酯、山梨糖醇酐三油酸酯、山梨糖醇酐三硬脂酸酯等山梨糖醇酐脂肪酸酯類;聚氧乙烯山梨糖醇酐單月桂酸酯、聚氧乙烯山梨糖醇酐單棕櫚酸酯、聚氧乙烯山梨糖醇酐單硬脂酸酯、聚氧乙烯山梨糖醇酐三油酸酯、聚氧乙烯山梨糖醇酐三硬脂酸酯等聚氧乙烯山梨糖醇酐脂肪酸酯類等非離子系界面活性劑;商品名EFtop EF301、EF303、EF352((股)TOHKEM PRODUCTS製)、商品名MEGAFACE F171、F173、R-08、R-30、R-30N、R-40LM(DIC(股)製)、Fluorad FC430、FC431(住友3M(股)製)、商品名AsahiGuard AG710、Surflon S-382、SC101、SC102、SC103、SC104、SC105、SC106(AGC(股)製)等氟系界面活性劑;有機矽氧烷聚合物KP341(信越化學工業(股)製)等,但不限定於此等。
界面活性劑,可單獨使用一種或組合使用二種以上。
本發明之膜形成用組成物含有界面活性劑之情況下,其含量相對於水解縮合物(聚有機矽氧烷)100質量份,一般為0.0001質量份~5質量份之範圍內,由抑制組成物中之析出之觀點等而言,較佳為1質量份以下;由充分獲得其效果之觀點等而言,較佳為0.001質量份以上,更佳為0.01質量份以上。
本發明之膜形成用組成物,較佳為不含有硬化觸媒作為添加劑。係為了避免當含有其作為添加劑,在光阻膜形成時及其後加熱時,有該添加劑之一部分往光阻膜中移動,造成特性劣化之情況。
進一步地,本發明之膜形成用組成物,亦可含有流變調整劑、接著輔助劑、pH調整劑等。流變調整劑,對提升膜形成用組成物之流動性為有效。接著輔助劑,對提升由本發明之膜形成用組成物所獲得之光阻下層膜,與半導體基板、有機下層膜或光阻膜之密著性為有效。
作為pH調整劑,可添加雙酚S、或雙酚S衍生物。雙酚S、或雙酚S衍生物之含量,相對於水解縮合物(聚有機矽氧烷)100質量份,為0.01質量份~20質量份,或0.01質量份~10質量份,或0.01質量份~5質量份。
本發明使用之水解縮合物,可藉由將上述水解性矽烷化合物水解及縮合而獲得。
水解,如上所述,可為完全水解,亦可為部分水解。如上所述,在本發明之膜形成用組成物所含之水解縮合物中,亦可在含有完全水解物的同時含有部分水解物。此外,在組成物中,亦可殘留為單量體(單體)之水解性矽烷。
本發明中,如上所述,在上述水解性矽烷化合物之水解及縮合中,使用二種以上酸性化合物,由再現性更佳地獲得本發明之效果之觀點而言,係以下述方式決定水解性矽烷化合物之水解性基團每1莫耳之二種以上酸性化合物之使用量:使二種以上酸性化合物之酸性基團一般為0.001莫耳~10莫耳,較佳為0.002莫耳~5莫耳,更佳為0.003莫耳~3莫耳,再更佳為0.005莫耳~2莫耳,再進一步更佳為0.007莫耳~1莫耳。
本發明使用之水解性矽烷化合物,係具有與矽原子直接鍵結之烷氧基、芳烷氧基、醯氧基或鹵原子,含有烷氧基矽基、芳烷氧基矽基、醯氧基矽基或鹵化矽基之水解性基團者,在其水解中,水解性基團每1莫耳使用之水,一般為0.5莫耳~100莫耳,較佳為1莫耳~10莫耳。
在水解及縮合時,基於促進水解及縮合之目的等,亦可使用水解觸媒。
作為其具體例,可列舉:金屬螯合化合物、有機鹼、無機鹼等,但不限定於此等。
水解觸媒,可單獨使用一種或組合使用二種以上,其水解性基團每1莫耳之使用量,一般為0.001莫耳~10莫耳,較佳為0.001莫耳~1莫耳。
作為金屬螯合化合物之具體例,可列舉:三乙氧基‧單(乙醯丙酮)鈦、三正丙氧基‧單(乙醯丙酮)鈦、三異丙氧基‧單(乙醯丙酮)鈦、三正丁氧基‧單(乙醯丙酮)鈦、三第二丁氧基‧單(乙醯丙酮)鈦、三第三丁氧基‧單(乙醯丙酮)鈦、二乙氧基‧雙(乙醯丙酮)鈦、二正丙氧基‧雙(乙醯丙酮)鈦、二異丙氧基‧雙(乙醯丙酮)鈦、二正丁氧基‧雙(乙醯丙酮)鈦、二第二丁氧基‧雙(乙醯丙酮)鈦、二第三丁氧基‧雙(乙醯丙酮)鈦、單乙氧基‧參(乙醯丙酮)鈦、單正丙氧基‧參(乙醯丙酮)鈦、單異丙氧基‧參(乙醯丙酮)鈦、單正丁氧基‧參(乙醯丙酮)鈦、單第二丁氧基‧參(乙醯丙酮)鈦、單第三丁氧基‧參(乙醯丙酮)鈦、肆(乙醯丙酮)鈦、三乙氧基‧單(乙醯乙酸乙酯)鈦、三正丙氧基‧單(乙醯乙酸乙酯)鈦、三異丙氧基‧單(乙醯乙酸乙酯)鈦、三正丁氧基‧單(乙醯乙酸乙酯)鈦、三第二丁氧基‧單(乙醯乙酸乙酯)鈦、三第三丁氧基‧單(乙醯乙酸乙酯)鈦、二乙氧基‧雙(乙醯乙酸乙酯)鈦、二正丙氧基‧雙(乙醯乙酸乙酯)鈦、二異丙氧基‧雙(乙醯乙酸乙酯)鈦、二正丁氧基‧雙(乙醯乙酸乙酯)鈦、二第二丁氧基‧雙(乙醯乙酸乙酯)鈦、二第三丁氧基‧雙(乙醯乙酸乙酯)鈦、單乙氧基‧參(乙醯乙酸乙酯)鈦、單正丙氧基‧參(乙醯乙酸乙酯)鈦、單異丙氧基‧參(乙醯乙酸乙酯)鈦、單正丁氧基‧參(乙醯乙酸乙酯)鈦、單第二丁氧基‧參(乙醯乙酸乙酯)鈦、單第三丁氧基‧參(乙醯乙酸乙酯)鈦、肆(乙醯乙酸乙酯)鈦、單(乙醯丙酮)參(乙醯乙酸乙酯)鈦、雙(乙醯丙酮)雙(乙醯乙酸乙酯)鈦、參(乙醯丙酮)單(乙醯乙酸乙酯)鈦等之鈦螯合化合物;三乙氧基‧單(乙醯丙酮)鋯、三正丙氧基‧單(乙醯丙酮)鋯、三異丙氧基‧單(乙醯丙酮)鋯、三正丁氧基‧單(乙醯丙酮)鋯、三第二丁氧基‧單(乙醯丙酮)鋯、三第三丁氧基‧單(乙醯丙酮)鋯、二乙氧基‧雙(乙醯丙酮)鋯、二正丙氧基‧雙(乙醯丙酮)鋯、二異丙氧基‧雙(乙醯丙酮)鋯、二正丁氧基‧雙(乙醯丙酮)鋯、二第二丁氧基‧雙(乙醯丙酮)鋯、二第三丁氧基‧雙(乙醯丙酮)鋯、單乙氧基‧參(乙醯丙酮)鋯、單正丙氧基‧參(乙醯丙酮)鋯、單異丙氧基‧參(乙醯丙酮)鋯、單正丁氧基‧參(乙醯丙酮)鋯、單第二丁氧基‧參(乙醯丙酮)鋯、單第三丁氧基‧參(乙醯丙酮)鋯、肆(乙醯丙酮)鋯、三乙氧基‧單(乙醯乙酸乙酯)鋯、三正丙氧基‧單(乙醯乙酸乙酯)鋯、三異丙氧基‧單(乙醯乙酸乙酯)鋯、三正丁氧基‧單(乙醯乙酸乙酯)鋯、三第二丁氧基‧單(乙醯乙酸乙酯)鋯、三第三丁氧基‧單(乙醯乙酸乙酯)鋯、二乙氧基‧雙(乙醯乙酸乙酯)鋯、二正丙氧基‧雙(乙醯乙酸乙酯)鋯、二異丙氧基‧雙(乙醯乙酸乙酯)鋯、二正丁氧基‧雙(乙醯乙酸乙酯)鋯、二第二丁氧基‧雙(乙醯乙酸乙酯)鋯、二第三丁氧基‧雙(乙醯乙酸乙酯)鋯、單乙氧基‧參(乙醯乙酸乙酯)鋯、單正丙氧基‧參(乙醯乙酸乙酯)鋯、單異丙氧基‧參(乙醯乙酸乙酯)鋯、單正丁氧基‧參(乙醯乙酸乙酯)鋯、單第二丁氧基‧參(乙醯乙酸乙酯)鋯、單第三丁氧基‧參(乙醯乙酸乙酯)鋯、肆(乙醯乙酸乙酯)鋯、單(乙醯丙酮)參(乙醯乙酸乙酯)鋯、雙(乙醯丙酮)雙(乙醯乙酸乙酯)鋯、參(乙醯丙酮)單(乙醯乙酸乙酯)鋯等之鋯螯合化合物;參(乙醯丙酮)鋁、參(乙醯乙酸乙酯)鋁等之鋁螯合化合物等,但不限定於此等。
作為有機鹼之具體例,可列舉:吡啶、吡咯、哌嗪、吡咯烷、哌啶、甲基吡啶、三甲胺、三乙胺、單乙醇胺、二乙醇胺、二甲基單乙醇胺、單甲基二乙醇胺、三乙醇胺、二氮雜雙環辛烷、二氮雜雙環壬烷、二氮雜雙環十一烯、四甲基氫氧化銨、四乙基氫氧化銨、四丙基氫氧化銨、四丁基氫氧化銨、三甲基苯基氫氧化銨、苄基三甲基氫氧化銨、苄基三乙基氫氧化銨等,但不限定於此等。
作為無機鹼之具體例,可列舉:氨、氫氧化鈉、氫氧化鉀、氫氧化鋇、氫氧化鈣等,但不限定於此等。
此等中,作為水解觸媒,較佳為金屬螯合化合物。
在進行水解及縮合時,作為溶劑亦可使用有機溶劑,作為其具體例,可列舉:正戊烷、異戊烷、正己烷、異己烷、正庚烷、異庚烷、2,2,4-三甲基戊烷、正辛烷、異辛烷、環己烷、甲基環己烷等脂肪族烴系溶劑;苯、甲苯、二甲苯、乙苯、三甲苯、甲基乙基苯、正丙苯、異丙苯、二乙苯、異丁苯、三乙苯、二異丙苯、正戊萘等芳香族烴系溶劑;甲醇、乙醇、正丙醇、異丙醇、正丁醇、異丁醇、二級丁醇、三級丁醇、正戊醇、異戊醇、2-甲基丁醇、二級戊醇、三級戊醇、3-甲氧基丁醇、正己醇、2-甲基戊醇、二級己醇、2-乙基丁醇、二級庚醇、3-庚醇、正辛醇、2-乙基己醇、二級辛醇、正壬醇、2,6-二甲基-4-庚醇、正癸醇、二級十一醇、三甲基壬醇、二級十四醇、二級十七醇、酚、環己醇、甲基環己醇、3,3,5-三甲基環己醇、苄醇、苯基甲基甲醇、二丙酮醇、甲酚等單醇系溶劑;乙二醇、丙二醇、1,3-丁二醇、2,4-戊二醇、2-甲基-2,4-戊二醇、2,5-己二醇、2,4-庚二醇、2-乙基-1,3-己二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、丙三醇等多元醇系溶劑;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-異丁基酮、甲基-正戊基酮、乙基-正丁基酮、甲基-正己基酮、二異丁基酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊二酮、丙酮基丙酮、二丙酮醇、苯乙酮、葑酮等酮系溶劑;乙醚、異丙醚、正丁醚、正己醚、2-乙基己基醚、環氧乙烷、1,2-環氧丙烷、二氧雜環戊烷、4-甲基二氧雜環戊烷、二噁烷、二甲基二噁烷、乙二醇單甲醚、乙二醇單乙醚、乙二醇二乙醚、乙二醇單正丁醚、乙二醇單正己醚、乙二醇單苯醚、乙二醇單-2-乙基丁醚、乙二醇二丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇二乙醚、二乙二醇單正丁醚、二乙二醇二正丁醚、二乙二醇單正己醚、乙氧基三乙二醇、四乙二醇二正丁醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、丙二醇單丁醚、丙二醇單甲醚乙酸酯、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇單丙醚、二丙二醇單丁醚、三丙二醇單甲醚、四氫呋喃、2-甲基四氫呋喃等醚系溶劑;碳酸二乙酯、乙酸甲酯、乙酸乙酯、γ-丁內酯、γ-戊內酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯、乙酸異丁酯、乙酸二級丁酯、乙酸正戊酯、乙酸二級戊酯、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、乙酸環己酯、乙酸甲基環己酯、乙酸正壬酯、乙醯乙酸甲酯、乙醯乙酸乙酯、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單正丁醚乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、丙二醇單丁醚乙酸酯、二丙二醇單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、乙二醇二乙酸酯、甲氧基三乙二醇乙酸酯、丙酸乙酯、丙酸正丁酯、丙酸異戊酯、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、鄰苯二甲酸二甲酯、鄰苯二甲酸二乙酯等酯系溶劑;N-甲基甲醯胺、N,N-二甲基甲醯胺、N,N-二乙基甲醯胺、乙醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基丙醯胺、N-甲基吡咯烷酮等含氮系溶劑;二甲硫醚、二乙硫醚、噻吩、四氫噻吩、二甲基亞碸、環丁碸、1,3-丙烷磺內酯等含硫系溶劑等,但不限定於此等。此等溶劑,可以單獨使用一種或組合使用二種以上。
此等中,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-異丁基酮、甲基-正戊基酮、乙基-正丁基酮、甲基-正己基酮、二異丁基酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊二酮、丙酮基丙酮、二丙酮醇、苯乙酮、葑酮等酮系溶劑,以溶液之保存穩定性此點而言較佳。
水解及縮合之反應溫度,一般為20℃~80℃。
作為水解性矽烷,在使用式(1)所表示之含胺基之矽烷以外之矽烷之情況下,式(1)所表示之含胺基之矽烷之加入量,在所有水解性矽烷中,一般為0.1莫耳%以上,但由再現性佳地獲得本發明之上述效果之觀點而言,較佳為0.5莫耳%以上,更佳為1莫耳%以上,再更佳為5莫耳%以上。
作為水解性矽烷,在使用式(2)所表示之其他矽烷或式(3)所表示之其他矽烷之情況下,此等其他矽烷之加入量,在所有水解性矽烷中,一般為0.1莫耳%以上,較佳為1莫耳%以上,更佳為5莫耳%以上,一般為99.9莫耳%以下,較佳為99莫耳%以下,更佳為95莫耳%以下。
作為水解性矽烷,在使用式(4)所表示之水解性有機矽烷之情況下,該有機矽烷之加入量,在所有水解性矽烷中,一般為0.01莫耳%以上,較佳為0.1莫耳%以上,一般為30莫耳%以下,較佳為10莫耳%以下。
作為水解性矽烷,在使用式(5-1)所表示之水解性有機矽烷之情況下,該有機矽烷之加入量,在所有水解性矽烷中,一般為0.1莫耳%以上,較佳為0.3莫耳%以上,一般為50莫耳%以下,較佳為30莫耳%以下。
可藉由在以上說明之條件下水解及縮合水解性矽烷化合物,從而製造水解縮合物。
反應結束後,可藉由將反應溶液直接或者稀釋或濃縮後,將其中和,並使用離子交換樹脂處理,從而將用於水解之酸觸媒移除。此外,亦可在此種處理之前或之後,藉由減壓蒸餾等,從反應溶液中去除副產物之醇及水、觸媒等。
若必要,可在進行此種精製後,藉由從含有水解縮合物之溶液中蒸餾去除全部或一部分溶劑,從而以固體或含有水解縮合物之溶液的形式獲得水解縮合物。
本發明之膜形成用組成物,可藉由混合上述水解性矽烷化合物之水解縮合物、溶劑、及在含有其他成分之情況下之該其他成分來製造。此時,可預先準備含有水解縮合物等之溶液,並將此溶液與溶劑及其他成分混合。
混合順序不特別限定。例如:可在含有水解縮合物等之溶液中,加入溶劑並混合,再於該混合物中加入其他成分;亦可將含有水解縮合物等之溶液、溶劑及其他成分同時混合。
若必要,亦可在最後進一步以追加方式加入溶劑,或使混合物中不含較易溶於溶劑之一部分成分而在最後才將其加入,由抑制構成成分之凝集與分離、再現性佳地調製均勻性優異之組成物之觀點而言,較佳係預先準備已良好地溶解水解縮合物等之溶液,並使用此調製組成物。再者,需留意:水解縮合物等,根據一同混合之溶劑之種類及量、其他成分之量及性質等,在此等混合時可能凝集或沉澱。此外,亦需留意:在使用已溶解水解縮合物等之溶液調製組成物之情況下,必須決定水解縮合物等之溶液之濃度及其使用量,使最終獲得之組成物中之水解縮合物等為期望之量。
在組成物之調製中,亦可在成分不分解或變質之範圍內適當加熱。
本發明中,膜形成用組成物,亦可在製造組成物之中間階段或混合所有成分後,使用亞微米級之過濾器等過濾。
本發明之膜形成用組成物之固體成分之濃度,相對於該組成物之質量,一般為0.1質量%~50質量%,由抑制固體成分之析出之觀點等而言,較佳為30質量%以下,更佳為25質量%以下。
固體成分中之水解性矽烷化合物之水解縮合物之比例,由再現性佳地獲得上述本發明之效果之觀點而言,一般為50質量%以上,較佳為60質量%以上,更佳為70質量%以上,再更佳為80質量%以上,再進一步更佳為90質量%以上。
本發明之膜形成用組成物,可較合適地用作使用於微影步驟之光阻下層膜形成用之組成物。
本發明之一態樣中,在使用於半導體裝置之製造之基板(例如:矽晶圓基板、覆蓋有矽/二氧化矽之基板、氮化矽基板、玻璃基板、ITO基板、聚醯亞胺基板、及覆蓋有低介電常數材料(low-k材料)之基板等)上,藉由旋轉器、塗佈機等適當的塗佈方法,塗佈由本發明之膜形成用組成物所成之光阻下層膜形成用組成物,其後,藉由燒成形成本發明之光阻下層膜。
燒成條件,一般從燒成溫度80℃~250℃、燒成時間0.3分鐘~60分鐘之中適當地選擇,較佳為燒成溫度150℃~250℃、燒成時間0.5分鐘~2分鐘。
本發明之光阻下層膜,亦可進一步含有金屬氧化物。
作為該種金屬氧化物,可列舉例如:錫(Sn)、鈦(Ti)、鋁(Al)、鋯(Zr)、鋅(Zn)、鈮(Nb)、鉭(Ta)及W(鎢)等金屬以及硼(B)、矽(Si)、鍺(Ge)、砷(As)、銻(Sb)、及碲(Te)等類金屬中之一種或組合二種以上之氧化物,但不限定於此等。
作為本發明之光阻下層膜之膜厚,例如為10nm~1,000nm,或為20nm~500nm,或為50nm~300nm,或為100nm~200nm。
接著,在本發明之光阻下層膜上,形成例如光阻劑膜。光阻劑膜之形成,可藉由習知方法,亦即在本發明之光阻下層膜上,塗佈光阻劑膜形成用組成物並燒成來進行。光阻劑膜之膜厚,例如為50nm~10,000nm,或為100nm~2,000nm,或為200nm~1,000nm。
本發明之其他態樣中,可在基板上形成有機下層膜後,在此之上形成本發明之光阻下層膜,並進一步在其上形成光阻劑膜。藉此,即使在為了防止光阻劑膜之圖案寬度變窄、圖案倒塌而薄薄地覆蓋光阻劑膜之情況下,亦可藉由選擇適當之蝕刻氣體來加工基板。例如,將可對光阻劑膜實現充分快速之蝕刻速度之氟系氣體用作蝕刻氣體,可加工本發明之光阻下層膜;此外,將可對本發明之光阻下層膜實現充分快速之蝕刻速度之氧系氣體用作蝕刻氣體,可加工有機下層膜;進一步地,將可對有機下層膜實現充分快速之蝕刻速度之氟系氣體用作蝕刻氣體,可加工基板。
再者,此時可使用之基板及塗佈方法,可列舉與上述相同者。
作為在本發明之光阻下層膜上形成之光阻劑膜之材料,只要係對曝光所使用之光感光者,則不特別限定。負型光阻劑及正型光阻劑材料之任一者均可使用,作為其具體例,可列舉:由酚醛清漆樹脂與1,2-萘醌二疊氮磺酸酯所成之正型光阻劑材料;由具有藉由酸分解而提升鹼溶解速度之基團之黏合劑與光酸產生劑所成之化學增幅型光阻劑材料;由藉由酸分解而提升光阻劑的鹼溶解速度之低分子化合物、鹼可溶性黏合劑與光酸產生劑所成之化學增幅型光阻劑材料;以及由具有藉由酸分解而提升鹼溶解速度之基團之黏合劑、藉由酸分解而提升光阻劑的鹼溶解速度之低分子化合物與光酸產生劑所成之化學增幅型光阻劑材料等,但不限定於此等。
可作為商品取得之具體例,可列舉:Shipley公司製之商品名APEX-E、住友化學(股)製之商品名PAR710、信越化學工業(股)製之商品名SEPR430等,但不限定於此等。
此外,亦可較合適地使用例如:如Proc. SPIE, Vol.3999, 300-334(2000)、Proc. SPIE, Vol.3999, 357-364(2000)、及Proc. SPIE, Vol.3999, 365-374(2000)所記載之含氟原子聚合物系光阻劑材料。
接著,通過指定的光罩而進行曝光。曝光,可使用KrF準分子雷射(波長248nm)、ArF準分子雷射(波長193nm)、F2準分子雷射(波長157nm)等。
曝光後,根據需要亦可進行曝光後加熱(post exposure bake)。曝光後加熱,以從加熱溫度70℃~150℃、加熱時間0.3分鐘~10分鐘中適當選擇之條件來進行。
本發明中,作為光阻材料,可使用電子束微影用光阻材料及EUV微影用光阻材料來取代光阻劑材料。
作為電子束微影用光阻材料,負型、正型均可使用,作為其具體例,可列舉:由酸產生劑與具有藉由酸分解而使鹼溶解速度變化之基團之黏合劑所成之化學增幅型光阻材料;由鹼可溶性黏合劑、酸產生劑與藉由酸分解而使光阻的鹼溶解速度變化之低分子化合物所成之化學增幅型光阻材料;由酸產生劑、具有藉由酸分解而使鹼溶解速度變化之基團之黏合劑與藉由酸分解而使光阻的鹼溶解速度變化之低分子化合物所成之化學增幅型光阻材料;由具有藉由電子束分解而使鹼溶解速度變化之基團之黏合劑所成之非化學增幅型光阻材料;由具有藉由電子束切斷而使鹼溶解速度變化之部位之黏合劑所成之非化學增幅型光阻材料等,但不限定於此等。在使用此等之電子束微影用光阻材料之情況下,與將照射源設為電子束而使用光阻劑材料之情況相同地,亦可形成光阻圖案。
作為EUV微影用光阻材料,可使用甲基丙烯酸酯樹脂系光阻材料。
接著,藉由顯影液(例如鹼顯影液)進行顯影。藉此,在例如使用正型光阻劑材料之情況下,曝光部分之光阻劑膜被去除,從而形成光阻劑膜之圖案。
作為顯影液之具體例,可列舉:氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物之水溶液;氫氧化四甲銨、氫氧化四乙銨、膽鹼等之氫氧化四級銨之水溶液;乙醇胺、丙胺、乙二胺等之胺水溶液等的鹼性水溶液等,但不限定於此等。
本發明中,作為顯影液可使用有機溶劑。亦即,曝光後藉由顯影液(有機溶劑)進行顯影。藉此,在例如使用負型光阻劑材料之情況下,未曝光部分之光阻劑膜被去除,從而形成光阻劑膜之圖案。
可作為該種顯影液使用之有機溶劑之具體例,可列舉:乙酸甲酯、乙酸丁酯、乙酸乙酯、乙酸異丙酯、乙酸戊酯、乙酸異戊酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、丙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、乙二醇單苯醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單丙醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單苯醚乙酸酯、二乙二醇單丁醚乙酸酯、乙酸2-甲氧基丁酯、乙酸3-甲氧基丁酯、乙酸4-甲氧基丁酯、乙酸3-甲基-3-甲氧基丁酯、乙酸3-乙基-3-甲氧基丁酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、乙酸2-乙氧基丁酯、乙酸4-乙氧基丁酯、乙酸4-丙氧基丁酯、乙酸2-甲氧基戊酯、乙酸3-甲氧基戊酯、乙酸4-甲氧基戊酯、乙酸2-甲基-3-甲氧基戊酯、乙酸3-甲基-3-甲氧基戊酯、乙酸3-甲基-4-甲氧基戊酯、乙酸4-甲基-4-甲氧基戊酯、丙二醇二乙酸酯、甲酸甲酯、甲酸乙酯、甲酸丁酯、甲酸丙酯、乳酸乙酯、乳酸丁酯、乳酸丙酯、碳酸乙酯、碳酸丙酯、碳酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、丙酮酸丁酯、乙醯乙酸甲酯、乙醯乙酸乙酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸異丙酯、2-羥基丙酸甲酯、2-羥基丙酸乙酯、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-甲氧基丙酸丙酯等,但不限定於此等。
根據需要,顯影液亦可含有界面活性劑等。
顯影,以從溫度5℃~50℃、時間10秒~600秒中適當選擇之條件來進行。
接著,將如此形成之光阻劑膜(上層)之圖案作為保護膜進行本發明之光阻下層膜(中間層)之去除,接著將由圖案化之光阻劑膜及本發明之光阻下層膜(中間層)所成之膜作為保護膜,進行有機下層膜(下層)之去除。最後,將圖案化之本發明之光阻下層膜(中間層)及有機下層膜(下層)作為保護膜,進行半導體基板之加工。
首先,將去除光阻劑膜部分之本發明之光阻下層膜(中間層)藉由乾蝕刻移除,使半導體基板露出。
在本發明之光阻下層膜之乾蝕刻,可使用:四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷、一氧化碳、氬氣、氧氣、氮氣、六氟化硫、二氟甲烷、三氟化氮、三氟化氯、氯氣、三氯硼烷、二氯硼烷等氣體。
在光阻下層膜之乾蝕刻,較佳係使用鹵系氣體。藉由鹵系氣體之乾蝕刻中,基本上由有機物質所成之光阻劑膜不易被去除。相對於此,含有大量矽原子之本發明之光阻下層膜會迅速地被鹵系氣體去除。因此,可抑制伴隨光阻下層膜之乾蝕刻而來之光阻劑膜之膜厚的減少。並且,其結果,可將光阻劑膜以薄膜使用。光阻下層膜之乾蝕刻較佳係藉由氟系氣體,且作為氟系氣體,可列舉例如:四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷、二氟甲烷(CH2
F2
)等,但不限定於此等。
其後,將由圖案化之光阻劑膜及本發明之光阻下層膜所成之膜作為保護膜,進行有機下層膜之去除。有機下層膜(下層)較佳係藉由氧系氣體之乾蝕刻來進行。其原因係:含有大量矽原子之本發明之光阻下層膜不易在藉由氧系氣體之乾蝕刻中被去除。
最後,進行半導體基板之加工。半導體基板之加工,較佳係藉由氟系氣體之乾蝕刻來進行。
作為氟系氣體,可列舉例如:四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷、二氟甲烷(CH2
F2
)等,但不限定於此等。
在本發明之光阻下層膜之上層,可在光阻劑膜形成前形成有機系之抗反射膜。作為此處所使用之抗反射膜組成物並無特別限制,例如可從至今為止於微影製程中慣用者之中任意地選擇使用,此外,可藉由慣用之方法,例如旋轉器、塗佈機之塗佈及燒成,來進行抗反射膜的形成。
塗佈有由本發明之膜形成用組成物所成之光阻下層膜形成用組成物之基板,可在其表面具有以CVD法等形成之有機系或無機系抗反射膜,亦可在其上形成本發明之光阻下層膜。在基板上形成有機下層膜後,在此之上形成本發明之光阻下層膜之情況下,所使用之基板,亦可為在其表面具有以CVD法等形成之有機系或無機系抗反射膜者。
此外,由本發明之光阻下層膜形成用組成物形成之光阻下層膜,根據在微影製程中使用之光之波長,對該光有吸收之情形。並且,在該種情況下,可作為具有防止來自基板的反射光之效果之抗反射膜而發揮功能。進一步地,本發明之光阻下層膜,亦可用作用於防止基板與光阻劑膜互相作用的層、具有防止光阻劑膜所使用之材料或向光阻劑膜之曝光時所生成之物質對基板的不良影響之功能的層、具有防止在加熱燒成時從基板生成之物質向光阻劑膜擴散之功能的層、及用於減少半導體基板介電質層所造成之光阻劑膜的中毒效果的阻隔層等。
由本發明之光阻下層膜形成用組成物形成之光阻下層膜,能夠應用於雙鑲嵌製程中所使用之形成有通孔之基板,並且能夠作為可將孔無間隙地填充之填充材料(嵌入材料)使用。此外,亦可作為用於將具有凹凸之半導體基板之表面平坦化的平坦化材料來使用。
作為EUV光阻之下層膜,除了作為硬光罩之功能以外亦可使用於以下目的。可為了形成不會與EUV光阻膜互相混合,並能夠防止在EUV曝光時不期望之曝光光,例如上述之深紫外(DUV)光從基板或界面之反射的EUV光阻之下層抗反射膜,而使用本發明之光阻下層膜形成用組成物。能夠作為EUV光阻膜之下層膜而有效率地防止反射。在用作EUV光阻下層膜之情況下,製程可與光阻劑用下層膜相同地進行。
以上說明之本發明之膜形成用組成物,可較合適地用於半導體元件之製造;根據本發明之半導體元件之製造方法,例如根據包含:於基板上形成有機下層膜之步驟、於上述有機下層膜上使用第1觀點至第12觀點中任一觀點所記載之膜形成用組成物來形成光阻下層膜之步驟、以及在上述光阻下層膜上形成光阻膜之步驟之半導體元件之製造方法,可靠性高之半導體元件之良好的製造為可期待的。
[實施例]
以下,列舉合成例及實施例更具體地說明本發明,但本發明不限定於下述者。
再者,重量平均分子量,係藉由GPC分析以聚苯乙烯換算所獲得之分子量。GPC分析,係使用GPC裝置(商品名HLC-8220GPC,東曹(股)製)、GPC管柱(商品名ShodexKF803L、KF802、KF801,昭和電工(股)製),管柱溫度設為40℃,使用四氫呋喃作為溶離液(溶出溶劑),流量(流速)設為1.0mL/min,並使用聚苯乙烯(昭和電工(股)製)作為標準樣品來進行。
[1]聚合物(水解縮合物)之合成
(合成例1)
將四乙氧基矽烷[東京化成工業(股)製]20.2g、甲基三乙氧基矽烷[東京化成工業(股)製]11.3g及丙二醇單乙醚47.8g放入300mL燒瓶中攪拌,在將所獲得之溶液以磁攪拌器攪拌的同時,向其滴加硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]10.2g、甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.2g及二甲胺基丙基三甲氧基矽烷[東京化成工業(股)製]0.37g之混合溶液。
滴加後,將燒瓶轉移至調整為60℃之油浴中,並回流240分鐘。其後,藉由在減壓下蒸餾去除乙醇、甲醇及水,而獲得以丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之濃縮液。再者,所獲得之濃縮液之固體成分濃度,在以140℃加熱之情況下之固體殘餘物換算中係超過20質量%。
接著,在所獲得之濃縮液中,加入丙二醇單乙醚,並將濃度調整為在以140℃加熱之情況下之固體殘餘物換算中為20質量%,而獲得將丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E1)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為1,800。
[化32]
(合成例2)
使用對甲苯磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.2g取代甲磺酸水溶液(濃度0.2mol/L)10.2g,此外以與合成例1相同之方法,來獲得水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E2)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為1,900。
[化33]
(合成例3)
使用樟腦磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.2g取代甲磺酸水溶液(濃度0.2mol/L)10.2g,此外以與合成例1相同之方法,來獲得水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E3)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為2,000。
[化34]
(合成例4)
使用三氟乙酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.2g取代硝酸水溶液(濃度0.2mol/L)10.2g,此外以與合成例1相同之方法,來獲得水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E4)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為2,200。
[化35]
(合成例5)
使用馬來酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.2g取代硝酸水溶液(濃度0.2mol/L)10.2g,此外以與合成例1相同之方法,來獲得水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E5)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為2,400。
[化36]
(合成例6)
使用方酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.2g取代硝酸水溶液(濃度0.2mol/L)10.2g,此外以與合成例1相同之方法,來獲得水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E6)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為2,400。
[化37]
(合成例7)
將四乙氧基矽烷[東京化成工業(股)製]19.9g、甲基三乙氧基矽烷[東京化成工業(股)製]9.65g、雙環[2.2.1]庚-5-烯-2-基三乙氧基矽烷[東京化成工業(股)製]2.04g及丙二醇單乙醚47.9g放入300mL燒瓶中攪拌,在將所獲得之溶液以磁攪拌器攪拌的同時,向其滴加硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]10.0g、甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.0g及二甲胺基丙基三甲氧基矽烷[東京化成工業(股)製]0.36g之混合溶液。
滴加後,將燒瓶轉移至調整為60℃之油浴中,並回流240分鐘。其後,藉由在減壓下蒸餾去除乙醇、甲醇及水,而獲得以丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之濃縮液。再者,所獲得之濃縮液之固體成分濃度,在以140℃加熱之情況下之固體殘餘物換算中係超過20質量%。
接著,在所獲得之濃縮液中,加入丙二醇單乙醚,並將濃度調整為在以140℃加熱之情況下之固體殘餘物換算中為20質量%,而獲得將丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E7)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為1,800。
[化38]
(合成例8)
將四乙氧基矽烷[東京化成工業(股)製]19.3g、甲基三乙氧基矽烷[東京化成工業(股)製]9.36g、二烯丙基異氰脲酸酯丙基三乙氧基矽烷[日產化學(股)製]3.19g及丙二醇單乙醚48.3g放入300mL燒瓶中攪拌,在將所獲得之溶液以磁攪拌器攪拌的同時,向其滴加硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]9.74g、甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]9.74g及二甲胺基丙基三甲氧基矽烷[東京化成工業(股)製]0.35g之混合溶液。
滴加後,將燒瓶轉移至調整為60℃之油浴中,並回流240分鐘。其後,藉由在減壓下蒸餾去除乙醇、甲醇及水,而獲得以丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之濃縮液。再者,所獲得之濃縮液之固體成分濃度,在以140℃加熱之情況下之固體殘餘物換算中係超過20質量%。
接著,在所獲得之濃縮液中,加入丙二醇單乙醚,並將濃度調整為在以140℃加熱之情況下之固體殘餘物換算中為20質量%,而獲得將丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E8)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為2,000。
[化39]
(合成例9)
將四乙氧基矽烷[東京化成工業(股)製]19.9g、甲基三乙氧基矽烷[東京化成工業(股)製]9.64g、氰硫基丙基三乙氧基矽烷[Gelest公司製]2.09g及丙二醇單乙醚48.0g放入300mL燒瓶中攪拌,在將所獲得之溶液以磁攪拌器攪拌的同時,向其滴加硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]10.0g、甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.0g及二甲胺基丙基三甲氧基矽烷[東京化成工業(股)製]0.36g之混合溶液。
滴加後,將燒瓶轉移至調整為60℃之油浴中,並回流240分鐘。其後,藉由在減壓下蒸餾去除乙醇、甲醇及水,而獲得以丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之濃縮液。再者,所獲得之濃縮液之固體成分濃度,在以140℃加熱之情況下之固體殘餘物換算中係超過20質量%。
接著,在所獲得之濃縮液中,加入丙二醇單乙醚,並將濃度調整為在以140℃加熱之情況下之固體殘餘物換算中為20質量%,而獲得將丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E9)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為1,900。
[化40]
(合成例10)
將四乙氧基矽烷[東京化成工業(股)製]19.6g、甲基三乙氧基矽烷[東京化成工業(股)製]9.49g、三乙氧基((2-甲氧基-4-(甲氧基甲基)苯氧基)甲基)矽烷[日產化學(股)製]2.70g及丙二醇單乙醚48.2g放入300mL燒瓶中攪拌,在將所獲得之溶液以磁攪拌器攪拌的同時,向其滴加硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]10.0g、甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.0g及二甲胺基丙基三甲氧基矽烷[東京化成工業(股)製]0.36g之混合溶液。
滴加後,將燒瓶轉移至調整為60℃之油浴中,並回流240分鐘。其後,藉由在減壓下蒸餾去除乙醇、甲醇及水,而獲得以丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之濃縮液。再者,所獲得之濃縮液之固體成分濃度,在以140℃加熱之情況下之固體殘餘物換算中係超過20質量%。
接著,在所獲得之濃縮液中,加入丙二醇單乙醚,並將濃度調整為在以140℃加熱之情況下之固體殘餘物換算中為20質量%,而獲得將丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E10)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為2,400。
[化41]
(合成例11)
將四乙氧基矽烷[東京化成工業(股)製]20.1g、甲基三乙氧基矽烷[東京化成工業(股)製]9.77g、苯基三甲氧基矽烷[東京化成工業(股)製]1.60g及丙二醇單乙醚47.8g放入300mL燒瓶中攪拌,在將所獲得之溶液以磁攪拌器攪拌的同時,向其滴加硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]10.0g、甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.0g及二甲胺基丙基三甲氧基矽烷[東京化成工業(股)製]0.37g之混合溶液。
滴加後,將燒瓶轉移至調整為60℃之油浴中,並回流240分鐘。其後,藉由在減壓下蒸餾去除乙醇、甲醇及水,而獲得以丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之濃縮液。再者,所獲得之濃縮液之固體成分濃度,在以140℃加熱之情況下之固體殘餘物換算中係超過20質量%。
接著,在所獲得之濃縮液中,加入丙二醇單乙醚,並將濃度調整為在以140℃加熱之情況下之固體殘餘物換算中為20質量%,而獲得將丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(E11)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為1,800。
[化42]
(比較合成例1)
將四乙氧基矽烷[東京化成工業(股)製]20.3g、三乙氧基甲基矽烷[東京化成工業(股)製]11.6g及丙二醇單乙醚47.7g放入300mL燒瓶中攪拌,在將所獲得之溶液以磁攪拌器攪拌的同時,向其滴加硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]20.4g。
滴加後,將燒瓶轉移至調整為60℃之油浴中,並回流240分鐘。其後,藉由在減壓下蒸餾去除乙醇、甲醇及水,而獲得以丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之濃縮液。再者,所獲得之濃縮液之固體成分濃度,在以140℃加熱之情況下之固體殘餘物換算中係超過20質量%。
接著,在所獲得之濃縮液中,加入丙二醇單乙醚,並將濃度調整為在以140℃加熱之情況下之固體殘餘物換算中為20質量%,而獲得將丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(C1)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為1,700。
[化43]
(比較合成例2)
將四乙氧基矽烷[東京化成工業(股)製]20.3g、三乙氧基甲基矽烷[東京化成工業(股)製]11.6g及丙二醇單乙醚47.7g放入300mL燒瓶中攪拌,在將所獲得之溶液以磁攪拌器攪拌的同時,向其滴加甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]20.4g。
滴加後,將燒瓶轉移至調整為60℃之油浴中,並回流240分鐘。其後,藉由在減壓下蒸餾去除乙醇、甲醇及水,而獲得以丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之濃縮液。再者,所獲得之濃縮液之固體成分濃度,在以140℃加熱之情況下之固體殘餘物換算中係超過20質量%。
接著,在所獲得之濃縮液中,加入丙二醇單乙醚,並將濃度調整為在以140℃加熱之情況下之固體殘餘物換算中為20質量%,而獲得將丙二醇單乙醚作為溶劑之水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(C2)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為1,900。
[化44]
(比較合成例3)
使用甲磺酸水溶液(濃度0.2mol/L)20.4g取代硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]10.2g及甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.2g,此外以與合成例1相同之方法,來獲得水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(C3)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為2,600。
[化45]
(比較合成例4)
使用硝酸水溶液(濃度0.2mol/L)20.4g取代硝酸水溶液(濃度0.2mol/L)[關東化學(股)製]10.2g及甲磺酸水溶液(濃度0.2mol/L)[東京化成工業(股)製]10.2g,此外以與合成例1相同之方法,來獲得水解縮合物(聚合物)之溶液(固體成分濃度20質量%)。所獲得之聚合物含有式(C4)所表示之結構,其重量平均分子量(Mw),藉由GPC以聚苯乙烯換算為2,000。
[化46]
[2]膜形成用組成物之調製
藉由將上述合成例所獲得之聚矽氧烷(聚合物)、酸(添加劑1)、光酸產生劑(添加劑2)、溶劑以表1所示之比例混合,並以0.1μm的氟樹脂製的過濾器進行過濾,各別調製膜形成用組成物。表1中的各添加量係以質量份表示。
再者,表1中的聚合物的添加比例並非表示聚合物溶液之添加量,而係表示聚合物本身的添加量。
此外,DIW係指超純水;PGEE係指丙二醇單乙醚;PGMEA係指丙二醇單甲醚乙酸酯;PGME係指丙二醇單甲醚。
進一步地,MA係指馬來酸;TPSNO3係指三苯基鋶硝酸鹽。
[表1]
聚合物 | 添加劑1 | 添加劑2 | 溶劑 | ||||
實施例1 | 合成例1 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例2 | 合成例2 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例3 | 合成例3 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例4 | 合成例4 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例5 | 合成例5 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例6 | 合成例6 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例7 | 合成例7 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例8 | 合成例8 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例9 | 合成例9 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例10 | 合成例10 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
實施例11 | 合成例11 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
比較例1 | 比較合成例1 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
比較例2 | 比較合成例1 | MA | TPSNO3 | PGEE | PGMEA | PGME | DIW |
(質量份) | 1 | 0.03 | 0.05 | 40 | 10 | 38 | 12 |
比較例3 | 比較合成例2 | MA | TPSNO3 | PGEE | PGMEA | PGME | DIW |
(質量份) | 1 | 0.03 | 0.05 | 40 | 10 | 38 | 12 |
比較例4 | 比較合成例3 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 | |
比較例5 | 比較合成例4 | MA | PGEE | PGMEA | PGME | DIW | |
(質量份) | 1 | 0.03 | 40 | 10 | 38 | 12 |
[3]有機下層膜形成用組成物之調製
氮氣下,於100ml的四口燒瓶中加入咔唑(6.69g、0.040mol,東京化成工業(股)製)、9-茀酮(7.28g、0.040mol,東京化成工業(股)製)、對甲苯磺酸一水合物(0.76g、0.0040mol,東京化成工業(股)製),並加入1,4-二噁烷(6.69g,關東化學(股)製)攪拌,升溫至100℃使其溶解並開始聚合。24小時後,放置冷卻至60℃。
於冷卻之反應混合物中加入氯仿(34g,關東化學(股)製)並稀釋,將稀釋之混合物添加至甲醇(168g,關東化學(股)製)中並使其沉澱。
將所獲得之沉澱物過濾,並以減壓乾燥機進行80℃、24小時乾燥,而得到目標之式(3-1)所表示之聚合物(以下簡稱為PCzFL)9.37g。
再者,PCzFL之1
H-NMR之測定結果如下:1
H-NMR(400MHz,DMSO-d6
):δ7.03-7.55(br,12H),δ7.61-8.10(br,4H),δ11.18(br,1H)。
此外,PCzFL之重量平均分子量Mw,藉由GPC以聚苯乙烯換算為2,800,多分散度Mw/Mn為1.77。
[化47]
將PCzFL 20g、作為交聯劑之四甲氧基甲基乙炔脲(日本Cytec Industries(股)(原三井Cytec(股))製,商品名Powderlink 1174)3.0g、作為觸媒之對甲苯磺酸吡啶鎓0.30g、及作為界面活性劑之MEGAFACE R-30(DIC(股)製,商品名)0.06g混合,並將混合物溶解於丙二醇單甲醚乙酸酯88g中。其後,使用孔徑0.10μm的聚乙烯製微過濾器進行過濾,進一步地,使用孔徑0.05μm的聚乙烯製微過濾器進行過濾,從而調製用於多層膜之微影製程之有機下層膜形成用組成物。
[4]溶劑耐性及顯影液溶解耐性試驗
將實施例1~11及比較例1及4中所調製之膜形成用組成物,使用旋轉器各別塗佈於矽晶圓上。於加熱板上以215℃加熱1分鐘,各別形成含Si之膜,並測量所獲得之含Si之膜之膜厚。
其後,在各含Si之膜上各別塗佈丙二醇單甲醚/丙二醇單甲醚乙酸酯的混合溶劑(7/3(V/V))並進行旋轉乾燥。接著,測量乾燥後之含Si之膜之膜厚,並對混合溶劑之塗佈前後膜厚變化的有無進行評價。以混合溶劑塗佈前之膜厚為基準,塗佈後的膜厚變化為未滿1%者評價為「良好」,膜厚變化為1%以上者評價為「未硬化」。
此外,以相同的方法於矽晶圓上已製作之各含Si之膜上,各別塗佈鹼顯影液(TMAH 2.38%水溶液),並進行旋轉乾燥。接著,測量乾燥後之下層膜之膜厚,並對顯影液之塗佈前後膜厚變化的有無進行評價。以顯影液塗佈前之膜厚為基準,膜厚變化為未滿1%者評價為「良好」,膜厚變化為1%以上者評價為「未硬化」。
所獲得之結果示於表2。
[表2]
膜形成用組成物 | 溶劑耐性 | 顯影液耐性 |
實施例1 | 良好 | 良好 |
實施例2 | 良好 | 良好 |
實施例3 | 良好 | 良好 |
實施例4 | 良好 | 良好 |
實施例5 | 良好 | 良好 |
實施例6 | 良好 | 良好 |
實施例7 | 良好 | 良好 |
實施例8 | 良好 | 良好 |
實施例9 | 良好 | 良好 |
實施例10 | 良好 | 良好 |
實施例11 | 良好 | 良好 |
比較例1 | 未硬化 | 未硬化 |
比較例4 | 良好 | 未硬化 |
如表2所示,由本發明之膜形成用組成物所獲得之膜,顯示對溶劑及顯影液之良好耐性。
[5]乾蝕刻速度之測定
乾蝕刻速度之測定中,使用以下的蝕刻器及蝕刻氣體。
Lam2300(科林研發(Lam Research)製):CF4
/CHF3
/N2
(氟系氣體)
RIE-10NR(Samco製):O2
(氧系氣體)
將實施例1~11中所獲得之膜形成用組成物,使用旋轉器各別塗佈於矽晶圓上,並在加熱板上以215℃加熱1分鐘,從而各別形成含Si之膜(膜厚0.02μm)。
此外,相同地將上述有機下層膜形成用組成物,使用旋轉器各別塗佈於矽晶圓上,並在加熱板上以215℃加熱1分鐘,從而形成有機下層膜(膜厚0.20μm)。
使用所獲得之各附有含Si之膜之矽晶圓,並使用CF4
/CHF3
/N2
氣體及O2
氣體作為蝕刻氣體,此外使用附有有機下層膜之矽晶圓,並使用O2
氣體作為蝕刻氣體,從而測定乾蝕刻速度。所獲得之結果示於表3。
再者,使用O2
氣體之乾蝕刻速度,係以相對於有機下層膜之乾蝕刻速度之比(耐性)表示。
[表3]
膜形成用組成物 | 氟系氣體 蝕刻速率 (nm/min) | 氧系氣體 耐性 (相對於有機下層膜 比率) |
實施例1 | 40 | 0.02 |
實施例2 | 38 | 0.02 |
實施例3 | 36 | 0.02 |
實施例4 | 40 | 0.03 |
實施例5 | 39 | 0.02 |
實施例6 | 40 | 0.02 |
實施例7 | 38 | 0.02 |
實施例8 | 45 | 0.03 |
實施例9 | 47 | 0.02 |
實施例10 | 38 | 0.02 |
實施例11 | 37 | 0.03 |
如表3所示,由本發明之膜形成用組成物所獲得之膜,在顯示對氟系氣體之高蝕刻速率的同時,與有機下層膜比較,顯示對氧系氣體之良好耐性。
[6]濕蝕刻速度之測定
將實施例1~11及比較例2及5中所獲得之膜形成用組成物,使用旋轉器各別塗佈於矽晶圓上,並在加熱板上以215℃加熱1分鐘,從而各別形成含Si之膜(膜厚0.02μm)。
使用所獲得之各附有含Si之膜之矽晶圓,並使用NH3
/HF混合水溶液作為濕蝕刻藥液,從而測定濕蝕刻速度。濕蝕刻速率,在10nm/min以上之情況評為良好,在未滿10nm/min之情況評為不良。所獲得之結果示於表4。
[表4]
膜形成用組成物 | NH3 /HF水溶液 濕蝕刻速率 |
實施例1 | 良好 |
實施例2 | 良好 |
實施例3 | 良好 |
實施例4 | 良好 |
實施例5 | 良好 |
實施例6 | 良好 |
實施例7 | 良好 |
實施例8 | 良好 |
實施例9 | 良好 |
實施例10 | 良好 |
實施例11 | 良好 |
比較例2 | 不良 |
比較例5 | 不良 |
如表4所示,由本發明之膜形成用組成物所獲得之膜,顯示對濕蝕刻藥液之良好濕蝕刻速率。
[7]藉由EUV曝光之光阻圖案之形成:負型溶劑顯影
在矽晶圓上,藉由旋轉塗佈上述有機下層膜形成用組成物,並在加熱板上以215℃加熱1分鐘,從而形成有機下層膜(A層)(膜厚90nm)。
在其上,藉由旋轉塗佈實施例1中所獲得之膜形成用組成物,並在加熱板上以215℃加熱1分鐘,從而形成光阻下層膜(B層)(膜厚20nm)。
進一步在其上,藉由旋轉塗佈EUV用光阻溶液(甲基丙烯酸酯樹脂系光阻),並在加熱板上以130℃加熱1分鐘,從而形成EUV光阻膜(C層),之後使用ASML製EUV曝光裝置(NXE3300B),在NA=0.33、σ=0.67/0.90、Dipole之條件下進行曝光。
曝光後,進行曝光後加熱(110℃ 1分鐘),於冷卻板上冷卻至室溫,並使用有機溶劑顯影液(乙酸丁酯)顯影1分鐘,接著進行沖洗處理從而形成光阻圖案。
以相同順序,使用實施例2~11及比較例3及4中所獲得之各組成物,各別形成光阻圖案。
接著,針對所獲得之各圖案,藉由確認圖案斷面觀察所得之圖案形狀,從而評價可否形成44nm節距(pitch)、22nm之線/間距。
圖案形狀之觀察中,為從基腳(footing)至底切之間的形狀,並且間距部沒有明顯殘渣之狀態評價為「良好」;光阻圖案剝離並倒塌之不佳狀態評價為「倒塌」;光阻圖案之上部或下部彼此接觸之不佳狀態評價為「橋接」。所獲得之結果示於表5。
[表5]
膜形成用組成物 | 評價結果 |
實施例1 | 良好 |
實施例2 | 良好 |
實施例3 | 良好 |
實施例4 | 良好 |
實施例5 | 良好 |
實施例6 | 良好 |
實施例7 | 良好 |
實施例8 | 良好 |
實施例9 | 良好 |
實施例10 | 良好 |
實施例11 | 良好 |
比較例3 | 倒塌 |
比較例4 | 倒塌 |
如表5所示,由本發明之膜成用組成物所獲得之膜,可作為光阻下層膜良好地發揮功能,並實現優異之微影特性。
Claims (14)
- 一種膜形成用組成物,其係含有使用二種以上酸性化合物進行水解性矽烷化合物之水解及縮合而獲得之水解縮合物、及溶劑;其特徵係 該水解性矽烷化合物,含有下述式(1)所表示之含胺基之矽烷: [化1] (式(1)中,R1 係與矽原子鍵結之基團,互相獨立地表示含有胺基之有機基; R2 係與矽原子鍵結之基團,表示可經取代之烷基、可經取代之芳基、可經取代之芳烷基、可經取代之鹵化烷基、可經取代之鹵化芳基、可經取代之鹵化芳烷基、可經取代之烷氧烷基、可經取代之烷氧芳基、可經取代之烷氧芳烷基、或可經取代之烯基,或者表示含有環氧基、丙烯醯基、甲基丙烯醯基、巰基或氰基之有機基; R3 係與矽原子鍵結之基團或原子,互相獨立地表示烷氧基、芳烷氧基、醯氧基或鹵原子; a係1~2之整數,b係0~1之整數,並滿足a+b≦2)。
- 如請求項1所述之膜形成用組成物,其中,該二種以上酸性化合物,含有選自鹽酸、硝酸、磷酸、硫酸、硼酸、雜多酸、側氧碳酸、含磺酸基之有機酸、含磷酸基之有機酸、含羧基之有機酸及含酚性羥基之有機酸所成群中相異之二種以上。
- 如請求項2所述之膜形成用組成物,其中,該二種以上酸性化合物,含有選自硝酸、硫酸、側氧碳酸、含磺酸基之有機酸及含羧基之有機酸所成群中相異之二種以上。
- 如請求項2所述之膜形成用組成物,其中,該二種以上酸性化合物,含有選自硫酸及含磺酸基之有機酸所成群中至少一種、及選自鹽酸、硝酸、磷酸、硼酸、雜多酸、側氧碳酸、含磷酸基之有機酸、含羧基之有機酸及含酚性羥基之有機酸所成群中至少一種。
- 如請求項2至4中任一項所述之膜形成用組成物,其中,該側氧碳酸,含有選自三角酸、方酸及玫棕酸之至少一種。
- 如請求項2至5中任一項所述之膜形成用組成物,其中,該含磺酸基之有機酸,含有選自芳香族磺酸、飽和脂肪族磺酸及不飽和脂肪族磺酸之至少一種。
- 如請求項6所述之膜形成用組成物,其中,該含磺酸基之有機酸,含有選自芳香族磺酸及飽和脂肪族磺酸之至少一種。
- 如請求項2至7中任一項所述之膜形成用組成物,其中,該含羧基之有機酸,含有選自甲酸、草酸、芳香族羧酸、飽和脂肪族羧酸及不飽和脂肪族羧酸之至少一種。
- 如請求項8所述之膜形成用組成物,其中,該含羧基之有機酸,含有不飽和脂肪族羧酸。
- 如請求項10所述之膜形成用組成物,其中,該伸烷基,係碳原子數1至10之直鏈狀或支鏈狀伸烷基。
- 如請求項1至11中任一項所述之膜形成用組成物,其中,該膜形成用組成物係使用於微影步驟之光阻下層膜形成用。
- 一種光阻下層膜,其特徵係由請求項1至12中任一項所述之膜形成用組成物所獲得。
- 一種半導體元件之製造方法,其特徵係包含: 於基板上形成有機下層膜之步驟; 於該有機下層膜上使用請求項1至12中任一項所述之膜形成用組成物來形成光阻下層膜之步驟;及 於該光阻下層膜上形成光阻膜之步驟。
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KR20220162160A (ko) | 2022-12-07 |
WO2021201196A1 (ja) | 2021-10-07 |
JPWO2021201196A1 (zh) | 2021-10-07 |
CN115398342A (zh) | 2022-11-25 |
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