TW201829671A - 包含具有二羥基之有機基的含矽阻劑下層膜形成組成物 - Google Patents
包含具有二羥基之有機基的含矽阻劑下層膜形成組成物 Download PDFInfo
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- TW201829671A TW201829671A TW106137006A TW106137006A TW201829671A TW 201829671 A TW201829671 A TW 201829671A TW 106137006 A TW106137006 A TW 106137006A TW 106137006 A TW106137006 A TW 106137006A TW 201829671 A TW201829671 A TW 201829671A
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- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
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- WVEKDHFNOMWIPR-UHFFFAOYSA-N triethoxy(2-ethoxyethyl)silane Chemical compound CCOCC[Si](OCC)(OCC)OCC WVEKDHFNOMWIPR-UHFFFAOYSA-N 0.000 description 1
- RERSXALNLHNCDC-UHFFFAOYSA-N triethoxy(3-ethoxypropyl)silane Chemical compound CCOCCC[Si](OCC)(OCC)OCC RERSXALNLHNCDC-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-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
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
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- G03F7/423—Stripping or agents therefor using liquids only containing mineral acids or salts thereof, containing mineral oxidizing substances, e.g. peroxy compounds
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- 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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- H01L21/02—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
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
- H01L21/0332—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their composition, e.g. multilayer masks, materials
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
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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
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- 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
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- H01L21/02214—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 the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—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 the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
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Abstract
本發明提供一種微影蝕刻步驟中,可作為硬遮罩使用的阻劑下層膜,其可使用藥液之濕式法、特別是可使用SPM(硫酸與過氧化氫水之混合水溶液)去除的含矽阻劑下層膜。 [解決手段] 一種阻劑下層膜形成組成物,其特徵為含有: 於含有相對於全水解性矽烷為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷,經鹼性物質水溶液而得之水解縮合物,與 於包含該水解縮合物的反應系中,再經由無機酸或陽離子交換樹脂,進行環氧基之開環反應所生成之包含具有二羥基之有機基的水解縮合物。 及,將該阻劑下層膜形成組成物塗佈於基板,經燒成後而製得之阻劑下層膜,其中,該阻劑下層膜可經含有具有1:1~4:1的H2
SO4
/H2
O2
之質量比的硫酸與過氧化氫之水溶液而去除。
Description
[0001] 本發明為有關一種於製造半導體裝置時所使用的基板與阻劑(例如,光阻劑、電子線阻劑)之間,形成下層膜的組成物。詳細而言為有關,於半導體裝置製造的微影蝕刻步驟中,可形成使用於光阻劑下層的下層膜的微影蝕刻用阻劑下層膜形成組成物。及,使用該下層膜形成組成物之阻劑圖型之形成方法。
[0002] 以往於半導體裝置之製造中,多使用光阻劑以微影蝕刻法進行微細加工。前述微細加工多於矽晶圓等的半導體基板上形成光阻劑之薄膜,並使用紫外線等活性光線介由描繪有半導體裝置圖型的遮罩圖型照射於該薄膜上,經顯影處理後,將所得之光阻劑圖型作為保護膜對基板進行蝕刻處理之方式,而於基板表面上形成對應前述圖型的微細凹凸之加工法。但,近年來,伴隨半導體裝置的高集積度化,所使用的活性光線也有由KrF準分子雷射(248nm)趨向ArF準分子雷射(193nm)之短波長化的傾向。伴隨此點,半導體基板反射活性光線所造成的影響,也形成極大的問題。 [0003] 又,半導體基板與光阻劑之間的下層膜,已知多為使用含有矽或鈦等的金屬元素之硬遮罩的膜。該情形中,阻劑與硬遮罩間,因其構成內容成份有著極大之差異,故要使用乾蝕刻將其去除之速度,則受到乾蝕刻所使用的氣體種類極大的影響。因此,適當地選擇氣體種類時,除不會造成光阻劑之膜厚被大幅削減,且也可以乾蝕刻方式去除硬遮罩。如此,於近年來的半導體裝置製造中,由抗反射效果開始,而達成各式各樣的效果之觀點,多於半導體基板與光阻劑之間配置阻劑下層膜。又,目前為止,仍對阻劑下層膜用之組成物進行各種研究,而極期待能在配合所要求的特性之多樣性等,而開發出阻劑下層膜用的新材料。 [0004] 近年來,伴隨半導體最先端裝置的植入層(implant layer)之微細化,而使用三層製程。但是,因通常的三層製程中,常會因乾蝕刻而對基板造成傷害,故極期待含矽阻劑下層膜得以濕式處理予以去除之步驟。 [0005] 已有揭示於3,4環氧環己基乙基三甲氧基矽烷與苯基三甲氧基矽烷,在鹼性觸媒存在下進行水解、縮合而得之聚矽氧烷中,加入乙酸,而製得阻劑下層膜形成組成物之記載(專利文獻1之實施例)。 [0006] 又有揭示於含有甲烷磺酸水溶液的乙醇中,混合四甲氧基矽烷、苯基三甲氧基矽烷,及2-(3,4-環氧環己基)乙基三甲氧基矽烷,經水解縮合而製造聚矽氧烷,而製得阻劑下層膜形成組成物之記載(專利文獻2之實施例)。 [先前技術文獻] [專利文獻] [0007] [專利文獻1] 特開2007-163846 [專利文獻2] 特開2012-078602
[發明所欲解決之問題] [0008] 本發明之目的為提供一種半導體裝置之製造時所使用的微影蝕刻用阻劑下層膜形成組成物。詳細而言,為提供一種於形成阻劑下層膜時,作為硬遮罩使用的微影蝕刻用阻劑下層膜形成組成物。又,提供一種可形成作為抗反射膜使用的阻劑下層膜之微影蝕刻用阻劑下層膜形成組成物。又,提供一種可形成不會與阻劑引起內部混合(inter mixing),具有較阻劑為更大的乾蝕刻速度之微影蝕刻用阻劑下層膜及形成該下層膜的阻劑下層膜形成組成物。 [0009] 本案發明,為提供一種於上層阻劑曝光並使用鹼顯影液或有機溶劑顯影之時,可形成優良的阻劑圖型形狀,且可經由隨後的乾蝕刻,而將矩形的阻劑圖型轉印於下層,而形成阻劑下層膜的阻劑下層膜形成組成物。 [0010] 於考量通常的三層製程中,因乾蝕刻而對基板造成的傷害時,多期待有一可使用濕式法去除含矽阻劑下層膜之步驟,本案發明為提供一種可使用藥液之濕式法,特別是可使用SPM(硫酸與過氧化氫水之混合水溶液)去除的含矽阻劑下層膜。 [解決問題之方法] [0011] 本案發明之第1觀點為有關,一種阻劑下層膜形成組成物,其為含有包含具有二羥基之有機基的水解縮合物之阻劑下層膜形成組成物,其特徵為, 前述包含具有二羥基之有機基的水解縮合物中之二羥基為,由包含具有環氧基之有機基的水解縮合物中之該環氧基,經由無機酸或陽離子交換樹脂進行開環反應而生成者, 前述包含具有環氧基之有機基的水解縮合物為,於含有相對於全水解性矽烷為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷,經鹼性物質水溶液而得之水解縮合物。 第2觀點為有關,如第1觀點之阻劑下層膜形成組成物,其中,上述具有環氧基之水解性矽烷,依全水解性矽烷為基準為含有10~90莫耳%之比例,該水解性矽烷為包含式(1)所示之水解性矽烷:(式(1)中,R1
為環己基環氧基、環氧丙氧烷基,或包含該些之有機基,且經Si-C鍵結而與矽原子鍵結者;R2
為烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、醯氧烷基,或具有丙烯醯基、甲基丙烯醯基、氫硫基、胺基、醯胺基、羥基、烷氧基、酯基、磺醯基,或氰基之有機基,或為該些之組合,且經Si-C鍵結而與矽原子鍵結者;R3
表示烷氧基、醯氧基,或鹵素基;a表示1之整數,b表示0~2之整數,a+b表示1~3之整數)。 第3觀點為有關,如第2觀點記載之阻劑下層膜形成組成物,其中,上述具有環氧基之水解性矽烷,依全水解性矽烷為基準為含有10~90莫耳%之比例,水解性矽烷,除式(1)之水解性矽烷以外,尚包含由式(2)及式(3)所成之群所選出之至少1種的水解性矽烷:(式(2)中,R4
為烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、醯氧烷基,或具有丙烯醯基、甲基丙烯醯基、氫硫基、胺基、醯胺基、羥基、烷氧基、酯基、磺醯基,或氰基之有機基,或為該些之組合,且經Si-C鍵結而與矽原子鍵結者,R5
表示烷氧基、醯氧基,或鹵素基,c表示0~3之整數)(式(3)中,R6
為烷基,且經Si-C鍵結而與矽原子鍵結者,R7
表示烷氧基、醯氧基,或鹵素基,Y表示伸烷基或伸芳基,d表示0或1之整數,e為0或1之整數)。 第4觀點為有關,如第2觀點或第3觀點記載之阻劑下層膜形成組成物,其中,式(1)之水解性矽烷,依全水解性矽烷為基準,為含有10~90莫耳%之比例。 第5觀點為有關,如第1觀點至第4觀點中任一項記載之阻劑下層膜形成組成物,其尚包含交聯性化合物。 第6觀點為有關,如第1觀點至第5觀點中任一項記載之阻劑下層膜形成組成物,其尚包含酸或酸產生劑。 第7觀點為有關,如第1觀點至第6觀點中任一項記載之阻劑下層膜形成組成物,其尚包含水。 第8觀點為有關,如第1觀點至第7觀點中任一項記載之阻劑下層膜形成組成物,其中,前述水解性矽烷於鹼性物質水溶液中生成水解縮合物,與前述環氧基經由無機酸或陽離子交換樹脂所進行的開環反應同時於有機溶劑中進行。 第9觀點為有關,一種阻劑下層膜,其為將第1觀點至第8觀點中任一項記載之阻劑下層膜形成組成物塗佈於基板,並經燒成後而得的阻劑下層膜,該阻劑下層膜可經由包含具有1:1~4:1的H2
SO4
/H2
O2
之質量比的硫酸與過氧化氫之水溶液而去除。 第10觀點為有關,一種如請求項1至請求項8中任一項記載之阻劑下層膜形成組成物的製造方法,其特徵為包含: 於含有相對於全水解性矽烷為基準為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷中,經鹼性物質水溶液進行水解縮合,而製得包含具有環氧基之有機基的水解縮合物之步驟,及 於包含該包含具有環氧基之有機基的水解縮合物的反應系中,經由無機酸或陽離子交換樹脂使該環氧基進行開環反應,而製得包含具有二羥基之有機基的水解縮合物之步驟。 第11觀點為有關,一種半導體裝置的製造方法,其特徵為包含: 將第1觀點至第8觀點中任一項記載之阻劑下層膜形成組成物塗佈於半導體基板上,經燒成處理,而形成阻劑下層膜之步驟、 將阻劑用組成物塗佈於前述下層膜上而形成阻劑膜之步驟、 使前述阻劑膜曝光之步驟、 於曝光後使阻劑進行顯影,而製得阻劑圖型之步驟、 依阻劑圖型而對阻劑下層膜進行蝕刻之步驟,及 使用圖型化的阻劑與阻劑下層膜對半導體基板進行加工之步驟。 第12觀點為有關,一種半導體裝置的製造方法,其特徵為包含: 於半導體基板上形成有機下層膜之步驟、 將第1觀點至第8觀點中任一項記載之阻劑下層膜形成組成物塗佈於其上,進行燒成處理而形成阻劑下層膜之步驟、 將阻劑用組成物塗佈於前述阻劑下層膜上,而形成阻劑層之步驟、 使前述阻劑膜曝光之步驟、 於曝光後使阻劑進行顯影,而製得阻劑圖型之步驟、 依阻劑圖型而對阻劑下層膜進行蝕刻之步驟、 使用圖型化之阻劑下層膜對有機下層膜進行蝕刻之步驟,及 使用圖型化之有機下層膜對半導體基板進行加工之步驟。 第13觀點為有關,如第11觀點或第12觀點記載之半導體裝置的製造方法,其尚包含使用含有硫酸與過氧化氫之水溶液去除圖型化的阻劑下層膜之步驟。 [發明之效果] [0012] 本案發明為,經環氧基之開環反應而使包含具有二羥基之有機基的水解縮合物(聚矽氧烷),含有於阻劑下層膜形成組成物中者。 二羥基雖為經環氧基的開環反應而形成,但因環氧基與有機酸進行反應時,有機酸殘基於環氧基的開環反應中會生成附加反應,而無法形成二羥基結構。又,水解性矽烷於水解過程使用酸時,會同時引起環氧基之開環反應,也會發生矽醇基與二羥基之副反應。 [0013] 本件發明為,於水解性矽烷水解時,使有機溶劑中含有鹼性物質水溶液,而可優先形成矽醇基,於形成聚矽氧烷後,再添加無機酸使環氧基變化為二羥基,而製得含有包含具有二羥基之有機基的聚矽氧烷之阻劑下層膜形成組成物。 [0014] 四乙氧基矽烷等的4官能性矽烷與具有有機基之3官能性矽烷的共同水解縮合物,主要因矽醇基相互間會形成交聯結構,故阻劑下層膜與塗佈於其頂部上的阻劑組成物不會引起內部混合(inter mixing)現象,但於隨後對下層或基板進行加工之後,於使用藥液,例如SPM(硫酸與過氧化氫水之混合水溶液)去除阻劑下層膜時,卻無法去除該類之阻劑下層膜。 但是,本發明之經由環氧基之開環反應而得之二羥基,其於二羥基相互間,或二羥基與矽醇基之間,或二羥基與有機交聯性化合物之間會形成交聯結構,故本案之阻劑下層膜與塗佈於其頂部上的阻劑組成物不會引起內部混合現象,且於隨後對下層進行加工之後,亦可使用SPM(硫酸與過氧化氫水之混合水溶液)予以去除。 [0015] 本案發明之阻劑下層膜,因具有含有具二羥基之有機基的矽氧烷之單位結構,故該單位結構所造成的交聯結構,可使用藥液以濕式法、特別是可以SPM(硫酸與過氧化氫水之混合水溶液)去除,且將阻劑下層膜由基板去除時,可降低對基板之傷害。 [實施發明之形態] [0016] 本案發明為,一種阻劑下層膜形成組成物,其為含有包含具有二羥基之有機基的水解縮合物之阻劑下層膜形成組成物,其特徵為, 前述包含具有二羥基之有機基的水解縮合物中之二羥基為,將包含具有環氧基之有機基的水解縮合物中之該環氧基,經由無機酸或陽離子交換樹脂進行開環反應而生成者, 前述包含具有環氧基之有機基的水解縮合物為,於含有相對於全水解性矽烷為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷,經鹼性物質水溶液而得之水解縮合物。 [0017] 具有環氧基之水解性矽烷,依全水解性矽烷為基準時,若未達10莫耳%之情形,對充分塗佈之阻劑組成物而言,將無法確保內部混合性。內部混合係指,於上層之組成物塗佈於下層膜上時,因下層膜產生溶解,而使下層膜與上層組成物產生層間混合狀態,而為不佳現象。 [0018] 又,具有環氧基之水解性矽烷依全水解性矽烷為基準,超過90莫耳%之情形時,也無法充份確保光學物性、耐乾蝕刻性等。 因此,本發明之阻劑下層膜形成組成物的製造方法,其特徵為包含 於含有相對於全水解性矽烷為基準為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷中,經鹼性物質水溶液進行水解縮合,而製得包含具有環氧基之有機基的水解縮合物之步驟,及 於包含該包含具有環氧基之有機基的水解縮合物的反應系中,經由無機酸或陽離子交換樹脂使該環氧基進行開環反應,而製得包含具有二羥基之有機基的水解縮合物之步驟。 [0019] 水解性矽烷經由鹼性物質水溶液而水解,與隨後的水解縮合物經由無機酸或陽離子交換樹脂進行環氧基之開環反應,可同時在有機溶劑中進行。含有水解縮合物之反應系係指,進行矽烷之水解與縮合之反應系,且可隨後進行環氧基之開環反應者。 [0020] 本發明之阻劑下層膜形成組成物,為含有上述水解縮合物,與溶劑。又,任意成份,可包含酸、水、醇、硬化觸媒、酸產生劑、其他之有機聚合物、吸光性化合物,及界面活性劑等。 [0021] 本發明之阻劑下層膜形成組成物中之固形成份,例如,含有0.1~50質量%,或0.1~30質量%、0.1~25質量%。其中,固形成份係指,由阻劑下層膜形成組成物的全成份去除溶劑成份者。 固形成份中所佔之水解性矽烷、其水解物,及其水解縮合物之比例,為20質量%以上,例如50~100質量%、60~99質量%、70~99質量%。 [0022] 又,上述水解縮合物,於製得水解性矽烷、水解物、水解縮合物之際,未完全水解之部份水解物,可再與水解縮合物混合,並使用該混合物。該縮合物為具有聚矽氧烷結構之聚合物。 [0023] 上述水解性矽烷,可使用式(1)之水解性矽烷。 式(1)中,R1
為環己基環氧基、環氧丙氧烷基,或包含該些之有機基,且經Si-C鍵結而與矽原子鍵結者;R2
為於式(1)中,R1
為環己基環氧基、環氧丙氧烷基,或包含該些之有機基,且經Si-C鍵結而與矽原子鍵結者;R2
為烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、醯氧烷基,或具有丙烯醯基、甲基丙烯醯基、氫硫基、胺基、醯胺基、羥基、烷氧基、酯基、磺醯基,或氰基之有機基,或為該些之組合,且經Si-C鍵結而與矽原子鍵結者;R3
表示烷氧基、醯氧基,或鹵素基;a表示1之整數,b表示0~2之整數,a+b表示1~3之整數。 [0024] 上述烷基為具有直鏈或分支的碳原子數1~10之烷基,例如甲基、乙基、n-丙基、i-丙基、n-丁基、i-丁基、s-丁基、t-丁基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基及1-乙基-2-甲基-n-丙基等。 [0025] 又,亦可使用環狀烷基,例如碳原子數1~10的環狀烷基,例如,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-n-丙基-環丙基、2-n-丙基-環丙基、1-i-丙基-環丙基、2-i-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-環丙基及2-乙基-3-甲基-環丙基等。亦可使用雙環基。 [0026] 烯基,可為碳數2~10之烯基,例如,乙烯基(ethenyl)、1-丙烯基、2-丙烯基、1-甲基-1-乙烯基(ethenyl)、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(ethenyl)、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-n-丙基乙烯基(ethenyl)、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-i-丙基乙烯基(ethenyl)、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-n-丁基乙烯基(ethenyl)、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-n-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-s-丁基乙烯基(ethenyl)、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-i-丁基乙烯基(ethenyl)、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-i-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-n-丙基-1-丙烯基、1-n-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-t-丁基乙烯基(ethenyl)、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-i-丙基-1-丙烯基、1-i-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-伸甲基-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-伸甲基-環戊基、1-環己烯基、2-環己烯基及3-環己烯基等。 [0027] 芳基,可為碳數6~40的芳基,例如苯基、o-甲基苯基、m-甲基苯基、p-甲基苯基、o-氯苯基、m-氯苯基、p-氯苯基、o-氟苯基、p-氫硫基苯基、o-甲氧基苯基、p-甲氧基苯基、p-胺基苯基、p-氰基苯基、α-萘基、β-萘基、o-聯苯基、m-聯苯基、p-聯苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基及9-菲基等。 [0028] 醯氧烷基,可列舉如,上述醯氧基與烷基之組合等,例如乙醯氧基甲基、乙醯氧基乙基、乙醯氧基丙基等。 [0029] 具有環氧基之有機基,例如,環氧丙氧基甲基、環氧丙氧基乙基、環氧丙氧基丙基、環氧丙氧基丁基、環氧環己基等。 [0030] 具有丙烯醯基之有機基,例如,丙烯醯基甲基、丙烯醯基乙基、丙烯醯基丙基等。 [0031] 具有甲基丙烯醯基之有機基,例如,甲基丙烯醯甲基、甲基丙烯醯乙基、甲基丙烯醯丙基等。 [0032] 具有氫硫基之有機基,例如,乙基氫硫基、丁基氫硫基、己基氫硫基、辛基氫硫基等。 [0033] 具有胺基之有機基,例如,胺基、胺基甲基、胺基乙基等。 [0034] 具有氰基之有機基,例如,氰基乙基、氰基丙基等。 [0035] 具有胺基,或醯胺基之有機基,例如,三聚氰酸衍生物等。 [0036] 具有羥基之有機基,例如,與芳基鍵結之羥基苯基等。 [0037] 具有磺醯基之有機基,例如,磺醯烷基,或磺醯基芳基等。 [0038] 烷氧烷基為被烷氧基所取代之烷基,例如甲氧基甲基、乙氧基甲基、乙氧基乙基、乙氧基甲基等。 [0039] 上述碳數1~20之烷氧基,例如,碳數1~20的具有直鏈、分支、環狀之烷基部份的烷氧基等,例如甲氧基、乙氧基、n-丙氧基、i-丙氧基、n-丁氧基、i-丁氧基、s-丁氧基、t-丁氧基、n-戊氧基、1-甲基-n-丁氧基、2-甲基-n-丁氧基、3-甲基-n-丁氧基、1,1-二甲基-n-丙氧基、1,2-二甲基-n-丙氧基、2,2-二甲基-n-丙氧基、1-乙基-n-丙氧基、n-己氧基、1-甲基-n-戊氧基、2-甲基-n-戊氧基、3-甲基-n-戊氧基、4-甲基-n-戊氧基、1,1-二甲基-n-丁氧基、1,2-二甲基-n-丁氧基、1,3-二甲基-n-丁氧基、2,2-二甲基-n-丁氧基、2,3-二甲基-n-丁氧基、3,3-二甲基-n-丁氧基、1-乙基-n-丁氧基、2-乙基-n-丁氧基、1,1,2-三甲基-n-丙氧基、1,2,2-三甲基-n-丙氧基、1-乙基-1-甲基-n-丙氧基及1-乙基-2-甲基-n-丙氧基等;又,環狀之烷氧基例如,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-n-丙基-環丙氧基、2-n-丙基-環丙氧基、1-i-丙基-環丙氧基、2-i-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-環丙氧基及2-乙基-3-甲基-環丙氧基等。 [0040] 上述碳數2~20的醯氧基,例如甲基羰氧基、乙基羰氧基、n-丙基羰氧基、i-丙基羰氧基、n-丁基羰氧基、i-丁基羰氧基、s-丁基羰氧基、t-丁基羰氧基、n-戊基羰氧基、1-甲基-n-丁基羰氧基、2-甲基-n-丁基羰氧基、3-甲基-n-丁基羰氧基、1,1-二甲基-n-丙基羰氧基、1,2-二甲基-n-丙基羰氧基、2,2-二甲基-n-丙基羰氧基、1-乙基-n-丙基羰氧基、n-己基羰氧基、1-甲基-n-戊基羰氧基、2-甲基-n-戊基羰氧基、3-甲基-n-戊基羰氧基、4-甲基-n-戊基羰氧基、1,1-二甲基-n-丁基羰氧基、1,2-二甲基-n-丁基羰氧基、1,3-二甲基-n-丁基羰氧基、2,2-二甲基-n-丁基羰氧基、2,3-二甲基-n-丁基羰氧基、3,3-二甲基-n-丁基羰氧基、1-乙基-n-丁基羰氧基、2-乙基-n-丁基羰氧基、1,1,2-三甲基-n-丙基羰氧基、1,2,2-三甲基-n-丙基羰氧基、1-乙基-1-甲基-n-丙基羰氧基、1-乙基-2-甲基-n-丙基羰氧基、苯基羰氧基,及甲苯磺醯基羰氧基等。 [0041] 上述鹵素基,例如,氟、氯、溴、碘等。 [0042] 上述式(1)所示水解性矽烷,例如以下所示內容。上述式中,T為烷基,可列舉如上述烷基之例示等,例如以甲基、乙基為佳。 本案發明中之水解性矽烷,可使用式(1)之水解性矽烷與其他水解性矽烷之組合,其他水解性矽烷可使用由式(2)及式(3)所成之群所選出之至少1種的水解性矽烷。 [0043] 將式(1)之水解性矽烷與其他水解性矽烷組合使用時,式(1)之水解性矽烷依全水解性矽烷為基準,可含有10~90莫耳%,或15~85莫耳%,或20~80莫耳%,或20~60莫耳%之範圍。 [0044] 式(2)中,R4
為烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、醯氧烷基,或具有丙烯醯基、甲基丙烯醯基、氫硫基、胺基、醯胺基、羥基、烷氧基、酯基、磺醯基,或氰基之有機基,或為該些之組合,且經Si-C鍵結而與矽原子鍵結者,R5
表示烷氧基、醯氧基,或鹵素基,c表示0~3之整數。 [0045] 式(3)中,R6
為烷基,且經Si-C鍵結而與矽原子鍵結者,R7
表示烷氧基、醯氧基,或鹵素基,Y表示伸烷基或伸芳基,d表示0或1之整數,e為0或1之整數。 [0046] 烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、醯氧烷基,或丙烯醯基、甲基丙烯醯基、氫硫基、胺基、醯胺基、羥基、烷氧基、酯基、磺醯基,或具有氰基之有機基、烷氧基、醯氧基,及鹵素基,可列舉如上述之例示。 [0047] 式(2)之具體例,可列舉如,四甲氧基矽烷、四氯矽烷、四乙醯氧基矽烷、四乙氧基矽烷、四n-丙氧基矽烷、四異丙氧基矽烷、四n-丁氧基矽烷、四乙醯氧基矽烷、甲基三甲氧基矽烷、甲基三氯矽烷、甲基三乙醯氧基矽烷、甲基三丙氧基矽烷、甲基三乙醯氧基矽烷、甲基三丁氧基矽烷、甲基三丙氧基矽烷、甲基三戊氧基矽烷、甲基三苯氧基矽烷、甲基三苄氧基矽烷、甲基三苯基乙氧基矽烷、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、乙烯基三乙醯氧基矽烷、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、t-丁氧基苯基三甲氧基矽烷、t-丁氧基苯基三乙氧基矽烷、t-丁氧基苯基三乙醯氧基矽烷、t-丁氧基苯基三氯矽烷、t-丁氧基苄基三甲氧基矽烷、t-丁氧基苄基三乙氧基矽烷、t-丁氧基苄基三乙醯氧基矽烷、t-丁氧基二苄基三氯矽烷、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-甲基丙烯酸基氧丙基三甲氧基矽烷、γ-氫硫基丙基三甲氧基矽烷、γ-氫硫基丙基三乙氧基矽烷、β-氰基乙基三乙氧基矽烷、氯甲基三甲氧基矽烷、氯甲基三乙氧基矽烷、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-甲基丙烯酸基氧丙基甲基二甲氧基矽烷、γ-甲基丙烯酸基氧丙基甲基二乙氧基矽烷、γ-氫硫基丙基甲基二甲氧基矽烷、γ-氫硫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、乙醯氧基甲基三甲氧基矽烷、乙醯氧基乙基三甲氧基矽烷、乙醯氧基丙基三甲氧基矽烷、乙醯氧基甲基三乙氧基矽烷、乙醯氧基乙基三乙氧基矽烷、乙醯氧基丙基三乙氧基矽烷等。 [0048] 式(3)之具體例,例如,伸甲基雙三甲氧基矽烷、伸甲基雙三氯矽烷、伸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。 [0049] 式(2)矽烷之例示,亦可例如以下之矽烷。 [0050] 上述式中,T為烷基,可列舉如上述烷基之例示,例如以甲基、乙基為佳。 [0051] 上述式中,R可為以下之例示。上述之中,醯氧基、嵌段羥基、烷氧基烷氧烷基,可經由無機酸之水解而生成羧酸或羥基。 [0052] 本發明所使用之水解縮合物,例如可為以下之例示。 [0053] 上述水解性矽烷之水解縮合物(聚有機矽氧烷),可為重量平均分子量1000~1000000,或1000~100000的縮合物。該些之分子量為依GPC分析之聚苯乙烯換算而得之分子量。 [0054] GPC之測定條件,例如可使用GPC裝置(商品名HLC-8220GPC、東曹股份有限公司製)、GPC管柱(商品名ShodexKF803L、KF802、KF801、昭和電工製)、管柱溫度為40℃、溶離液(溶出溶劑)為四氫呋喃、流量(流速)為1.0ml/min、標準樣品為聚苯乙烯(昭和電工股份有限公司製)進行測定。 [0055] 烷氧基矽烷基、醯氧矽烷基,或鹵化矽烷基之水解中,相對於水解性基每1莫耳,為使用0.5~100莫耳,較佳為使用1~10莫耳的水。 又,可使用相對於水解性基每1莫耳,為0.001~10莫耳,較佳為0.001~1莫耳的水解觸媒。 進行水解與縮合之際的反應溫度,通常為20~80℃。 水解,可進行完全水解,或部份水解皆可。即,水解縮合物中亦可殘留水解物或單體。 水解、縮合之際,可使用觸媒。 水解觸媒,例如,鹼性物質水溶液,鹼性物質之有機鹼、無機鹼等。 [0056] 水解觸媒之有機鹼,例如,吡啶、吡咯、哌嗪、吡咯啶、哌啶、甲吡啶、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、二氮雜雙環壬烯、二氮雜雙環十一烯、氫氧化四甲基銨、氫氧化四乙基銨、氫氧化四丙基銨、氫氧化四丁基銨、氫氧化苯基三甲基銨、氫氧化苄基三甲基銨、氫氧化苄基三乙基銨等。 [0057] 無機鹼,例如,氨、氫氧化鈉、氫氧化鉀、氫氧化鋇、氫氧化鈣等。該些可使用1種或同時使用2種以上皆可。 [0058] 水解所使用之有機溶劑,例如,n-戊烷、i-戊烷、n-己烷、i-己烷、n-庚烷、i-庚烷、2,2,4-三甲基戊烷、n-辛烷、i-辛烷、環己烷、甲基環己烷等的脂肪族烴系溶劑;苯、甲苯、二甲苯、乙基苯、三甲基苯、甲基乙基苯、n-丙基苯、i-丙基苯、二乙基苯、i-丁基苯、三乙基苯、二-i-丙基苯、n-戊基萘、三甲基苯等的芳香族烴系溶劑;甲醇、乙醇、n-丙醇、i-丙醇、n-丁醇、i-丁醇、sec-丁醇、t-丁醇、n-戊醇、i-戊醇、2-甲基丁醇、sec-戊醇、t-戊醇、3-甲氧基丁醇、n-己醇、2-甲基戊醇、sec-己醇、2-乙基丁醇、sec-庚醇、庚醇-3、n-辛醇、2-乙基己醇、sec-辛醇、n-壬醇、2,6-二甲基庚醇-4、n-癸醇、sec-十一烷醇、三甲基壬醇、sec-十四基醇、sec-庚基癸基醇、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(卡必醇)、二丙酮醇、甲酚等的單醇系溶劑;乙二醇、丙二醇、1,3-丁二醇、戊烷二醇-2,4、2-甲基戊烷二醇-2,4、己烷二醇-2,5、庚烷二醇-2,4、2-乙基己烷二醇-1,3、二乙二醇、二丙二醇、三乙二醇、三丙二醇、丙三醇等的多元醇系溶劑;丙酮、甲基乙酮、甲基-n-丙酮、甲基-n-丁酮、二乙酮、甲基-i-丁酮、甲基-n-戊酮、乙基-n-丁酮、甲基-n-己酮、二-i-丁酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊烷二酮、丙酮基丙酮、二丙酮醇、苯乙酮、葑酮等的酮系溶劑;乙醚、i-丙醚、n-丁醚、n-己醚、2-乙基己醚、環氧乙烷、1,2-環氧丙烷、二氧戊烷、4-甲基二氧戊烷、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-n-丁醚、乙二醇單-n-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-n-丁醚、二乙二醇二-n-丁醚、二乙二醇單-n-己醚、乙氧基三二醇、四乙二醇二-n-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-甲基四氫呋喃等的醚系溶劑;二乙基碳酸酯、乙酸甲酯、乙酸乙酯、γ-丁內酯、γ-己內酯、乙酸n-丙酯、乙酸i-丙酯、乙酸n-丁酯、乙酸i-丁酯、乙酸sec-丁酯、乙酸n-戊酯、乙酸sec-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n-壬酯、乙醯乙酸甲酯、乙醯乙酸乙酯、乙酸乙二醇單甲醚、乙酸乙二醇單乙醚、乙酸二乙二醇單甲醚、乙酸二乙二醇單乙醚、乙酸二乙二醇單-n-丁醚、乙酸丙二醇單甲醚、乙酸丙二醇單乙醚、乙酸丙二醇單丙醚、乙酸丙二醇單丁醚、乙酸二丙二醇單甲醚、乙酸二丙二醇單乙醚、二乙酸二醇、乙酸甲氧基三二醇、丙酸乙酯、丙酸n-丁酯、丙酸i-戊酯、草酸二乙酯、草酸二-n-丁酯、乳酸甲酯、乳酸乙酯、乳酸n-丁酯、乳酸n-戊酯、丙二酸二乙酯、苯二甲酸二甲酯、苯二甲酸二乙基等的酯系溶劑;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-甲基吡咯啶酮等的含氮系溶劑;硫化二甲酯、硫化二乙酯、噻吩、四氫噻吩、二甲基亞碸、環丁碸、1,3-丙烷磺內酯等的含硫系溶劑等。該些之溶劑可使用1種或2種以上的組合。 [0059] 特別是,丙酮、甲基乙酮、甲基-n-丙酮、甲基-n-丁酮、二乙酮、甲基-i-丁酮、甲基-n-戊酮、乙基-n-丁酮、甲基-n-己酮、二-i-丁酮、三甲基壬酮、環己酮、甲基環己酮、2,4-戊烷二酮、丙酮基丙酮、二丙酮醇、苯乙酮、葑酮等的酮系溶劑,就溶液保存安定性之觀點,而為更佳。 [0060] 上述水解縮合物可再經由無機酸或陽離子交換樹脂,使環氧基開環而生成二羥基。該無機酸,可以無機酸水溶液方式添加。無機酸水溶液之濃度,例如,可使用0.01M~10M左右的濃度。無機酸,例如為鹽酸、硝酸、硫酸、氟酸、磷酸等。 [0061] 又,陽離子交換樹脂,可列舉如,強酸性陽離子樹脂(例如磺酸型離子交換樹脂)、弱酸性陽離子樹脂(例如羧酸型離子交換樹脂)等。 [0062] 無機酸及陽離子交換樹脂之質子,於環氧基之開環反應中,具有作為觸媒之機能。本發明中,可經鹼性物質水溶液進行水解與縮合反應,於含有水解縮合物之反應系中,添加無機酸或陽離子交換樹脂時,可使無機酸或陽離子交換樹脂因中和殘存之鹼性物質而消耗。環氧基開環反應所使用之上述質子,相對於環氧基添加0.01~100莫耳%比例之質子時,雖可生成二羥基,但於考量中和鹼性物質所消耗的量時,也可添加0.01~1000莫耳%,或0.01~500莫耳%、0.01~300莫耳%、0.01~100莫耳%之比例。 [0063] 又,本發明中,於添加無機酸或陽離子交換樹脂後,可使用陰離子交換樹脂去除陰離子。陰離子交換樹脂,可添加強鹼性陰離子交換樹脂(例如四級銨型離子交換樹脂)、弱鹼性陰離子交換樹脂(例如聚胺型離子交換樹脂)等。 上述陽離子交換樹脂與陰離子交換樹脂,可經由反應系之過濾而容易取除。 [0064] 本發明中,尚包含交聯性化合物。 本發明所使用之交聯性化合物,例如,包含具有烷氧基甲基或羥基甲基之環結構的交聯性化合物,或具有嵌段異氰酸酯基的交聯性化合物等。 烷氧基甲基,較佳可使用甲氧基甲基。 [0065] 該交聯性化合物,例如,三聚氰胺系、取代脲系,或該些之聚合物系等。較佳為至少具有2個形成交聯的取代基之交聯劑,例如,甲氧基甲基化乙炔脲、丁氧基甲基化乙炔脲、甲氧基甲基化三聚氰胺、丁氧基甲基化三聚氰胺、甲氧基甲基化苯併胍胺、丁氧基甲基化苯併胍胺、甲氧基甲基化脲、丁氧基甲基化脲、甲氧基甲基化硫脲,或甲氧基甲基化硫脲等的化合物。又,亦可使用該些化合物之縮合物。四甲氧基甲基乙炔脲可使用三井科技(股)之POWERLINK 1174(PL-LI)。 [0066] 又,上述交聯劑亦可使用具有高耐熱性的交聯劑。高耐熱性的交聯劑,較佳為使用分子內含有具有芳香族環(例如,苯環、萘環)之形成交聯的取代基之化合物。 [0067] 該化合物,可列舉如,具有下述式(4)之部份結構的化合物,或具有下述式(5)之重複單位的聚合物或低聚物。[0068] 式(4)中,R11
及R12
分別表示氫原子、碳數1~10之烷基,或碳數6~20的芳基,n1為1~4之整數,n2為1~(5-n1)之整數,n1+n2表示2~5之整數。 式(5)中,R13
為氫原子或碳數1~10之烷基,R14
為碳數1~10之烷基,n3為1~4之整數,n4為0~(4-n3),n3+n4為1~4之整數。 低聚物及聚合物,可使用重複單位結構之數為2~100,或2~50的範圍者。該些之烷基或芳基,可列舉如,上述例示之內容。 [0069] 式(4)、式(5)之化合物、聚合物、低聚物,係如以下之例示。 [0070] 上述化合物可使用旭有機材工業(股)、本州化學工業(股)之製品。例如上述交聯劑之中,式(4-21)之化合物可使用旭有機材工業(股)、商品名TM-BIP-A。又,式(4-22)之化合物可使用本州化學工業(股)、商品名TMOM-BP。 [0071] 交聯性化合物的添加量,依所使用的塗佈溶劑、所使用的底層基板、所要求的溶液黏度、所要求的膜形狀等而變動,一般相對於全固形成份為0.001~80質量%,較佳為0.01~50質量%,特佳為0.05~40質量%。該些交聯劑雖可自我縮合引起交聯反應,但本發明之上述聚合物中,存在交聯性取代基時,可與該些交聯性取代基引發交聯反應。 [0072] 此外,本發明所使用的阻劑下層膜形成組成物中,可含有促進交聯反應之酸(酸性化合物)。前述酸(酸性化合物),例如,樟腦磺酸、枸椽酸、p-甲苯磺酸、吡啶鎓-p-甲苯磺酸、三氟甲烷磺酸、水楊酸、磺基水楊酸、吡啶鎓-磺基水楊酸、4-氯苯磺酸、吡啶鎓-4-氯苯磺酸、4-羥基苯磺酸、吡啶鎓-4-羥基苯磺酸、苯二磺酸、吡啶鎓-苯二磺酸、安息香酸、羥基安息香酸、1-萘磺酸,及吡啶鎓-1-萘磺酸等。該些交聯觸媒,可僅使用一種,或將二種以上組合使用。前述酸(酸性化合物),相對於縮合物(聚有機矽氧烷)100質量份,可使用0.01~10質量份,或0.05~5質量份,或0.1~3質量份,或0.3~2質量份,或0.5~1質量份。 [0073] 又,本發明之阻劑下層膜形成組成物中,可含有酸產生劑。酸產生劑,例如,熱酸產生劑或光酸產生劑等。特別是光酸產生劑,於阻劑曝光時不會產生酸。因此,可調整下層膜之酸性度。此點為調和下層膜的酸性度與上層阻劑之酸性度的方法之一。又,經由調整下層膜之酸性度,則可調整於上層形成之阻劑的圖型形狀。 [0074] 本案發明之阻劑下層膜形成組成物中,所含的光酸產生劑,例如,氯化鎓、碸醯亞胺化合物,及二磺醯基重氮甲烷化合物等。 [0075] 氯化鎓,例如,二苯基錪六氟磷酸鹽、二苯基錪三氟甲烷磺酸酯、二苯基錪九氟正丁烷磺酸酯、二苯基錪全氟正辛烷磺酸酯、二苯基錪樟腦磺酸酯、雙(4-tert-丁基苯基)錪樟腦磺酸酯及雙(4-tert-丁基苯基)錪三氟甲烷磺酸酯等的錪氯化合物,及三苯基鋶六氟鈦酸鹽、三苯基鋶九氟正丁烷磺酸酯、三苯基鋶樟腦磺酸酯及三苯基鋶三氟甲烷磺酸酯等的氯化鋶等。 [0076] 碸醯亞胺化合物,例如,N-(三氟甲烷磺醯氧基)琥珀醯亞胺、N-(九氟正丁烷磺醯氧基)琥珀醯亞胺、N-(樟腦磺醯氧基)琥珀醯亞胺及N-(三氟甲烷磺醯氧基)萘基醯亞胺等。 [0077] 二磺醯基重氮甲烷化合物,例如,雙(三氟甲基磺醯基)重氮甲烷、雙(環己基磺醯基)重氮甲烷、雙(苯基磺醯基)重氮甲烷、雙(p-甲苯磺醯基)重氮甲烷、雙(2,4-二甲基苯磺醯基)重氮甲烷,及甲基磺醯基-p-甲苯磺醯基重氮甲烷等。 [0078] 光酸產生劑可單獨使用一種,或二種以上組合使用。使用光酸產生劑時,其比例,例如,相對於縮合物(聚有機矽氧烷)100質量份,為0.01~5質量份,或0.1~3質量份,或0.5~1質量份。 [0079] 又,本發明之阻劑下層膜形成組成物中,可含有界面活性劑。界面活性劑,於將本案發明之阻劑下層膜形成組成物塗佈於基板之際,可有效地抑制沙孔(pinhole)及缺陷等的發生。 [0080] 本案發明之阻劑下層膜形成組成物中所含的界面活性劑,例如,聚氧乙烯基月桂醚、聚氧乙烯基硬脂醚、聚氧乙烯基鯨蠟醚、聚氧乙烯基油醚等的聚氧乙烯基烷醚類、聚氧乙烯基辛基酚醇醚、聚氧乙烯基壬基酚醇醚等的聚氧乙烯烷基烯丙醚類、聚氧乙烯基・聚氧丙烯基嵌段共聚物類、山梨糖醇單月桂酸酯、山梨糖醇單棕櫚酸酯、山梨糖醇單硬脂酸酯、山梨糖醇單油酸酯、山梨糖醇三油酸酯、山梨糖醇三硬脂酸酯等的山梨糖醇脂肪酸酯類、聚氧乙烯基山梨糖醇單月桂酸酯、聚氧乙烯基山梨糖醇單棕櫚酸酯、聚氧乙烯基山梨糖醇單硬脂酸酯、聚氧乙烯基山梨糖醇三油酸酯、聚氧乙烯基山梨糖醇三硬脂酸酯等的聚氧乙烯基山梨糖醇脂肪酸酯類等的非離子系界面活性劑、商品名F-TOPEF301、EF303、EF352((股)陶氏製程製)、商品名美格氟F171、F173,R-08,R-30,R-30N,R-40LM(DIC(股)製)、Fluorad FC430、FC431(住友3M(股)製)、商品名AsahiGuardAG710,SafreonS-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(股)製)等的氟系界面活性劑,及有機矽氧烷聚合物KP341(信越化學工業(股)製)等。該些界面活性劑可單獨使用亦可,或以二種以上的組合方式使用亦可。使用界面活性劑時,其比例,例如,相對於縮合物(聚有機矽氧烷)100質量份,為0.0001~5質量份,或0.001~1質量份,或0.01~0.5質量份。 [0081] 又,本案發明之阻劑下層膜形成組成物中,可添加流變調整劑及接著補助劑等。流變調整劑,對於提升下層膜形成組成物之流動性為有效者。接著補助劑,對於提升半導體基板或阻劑與下層膜之密著性為有效者。 [0082] 又,本發明之阻劑下層膜形成組成物中,可添加作為添加劑之雙酚S,或雙酚S衍生物。雙酚S,或雙酚S衍生物,相對於聚有機矽氧烷100質量份,為使用0.01~20質量份,或0.01~10質量份,或0.01~5質量份。 [0083] 較佳之雙酚S,或雙酚S衍生物,例如以下所例示之內容。 [0084] 本發明之阻劑下層膜形成組成物中所使用的溶劑,只要為可溶解前述固形成份之溶劑時,並未有特別之限制,皆可使用。該些溶劑,例如,甲基溶纖劑(cellosolve)乙酸酯、乙基溶纖劑乙酸酯、丙二醇、丙二醇單甲醚、丙二醇單乙醚、甲基異丁基甲醇(卡必醇)、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、甲基乙酮、環戊酮、環己酮、2-羥基丙酸乙基、2-羥基-2-甲基丙酸乙基、乙氧基乙酸乙基、羥基乙酸乙基、2-羥基-3-甲基丁酸甲基、3-甲氧基丙酸甲基、3-甲氧基丙酸乙基、3-乙氧基丙酸乙基、3-乙氧基丙酸甲基、丙酮酸甲基、丙酮酸乙基、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、3-甲氧基丁基乙酸酯、3-甲氧基丙基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基丙酸酯、3-甲基-3-甲氧基丁基丁酸酯、乙醯乙酸甲酯、甲苯、二甲苯、甲基乙酮、甲基丙酮、甲基丁酮、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-甲基吡咯啶酮、4-甲基-2-戊醇,及γ-丁內酯等。該些溶劑可單獨,或以二種以上的組合方式使用。 [0085] 以下,將對本發明之阻劑下層膜形成組成物之使用方法進行說明。 於製造半導體裝置所使用的基板(例如,矽晶圓基板、矽/二氧化矽被覆基板、氮化矽基板、玻璃基板、ITO基板、聚醯亞胺基板,及低介電係數材料(low-k材料)被覆基板等)上,使用旋轉塗佈機、塗佈機(Coater)等,依適當的塗佈方法塗佈本發明之阻劑下層膜形成組成物,隨後,進行燒成處理,而形成阻劑下層膜。燒成條件,例如,可於燒成溫度80℃~250℃、燒成時間0.3~60分鐘中,適當地選擇。較佳為燒成溫度150℃~250℃、燒成時間0.5~2分鐘。其中,所形成的下層膜之膜厚,例如,10~1000nm,或20~500nm,或30~300nm,或50~100nm。 [0086] 其次,於該阻劑下層膜上,例如形成光阻劑之層。光阻劑之層的形成,可周知之方法,即,將光阻劑組成物溶液塗佈於下層膜上,並經燒成處理之方式進行。光阻劑之膜厚,例如可為50~10000nm,或100~2000nm,或200~1000nm。 [0087] 本發明,可於基板上形成有機下層膜之膜後,於該膜上形成本發明之阻劑下層膜之膜,再於其上被覆光阻劑。如此,可使光阻劑之圖型寬度狹窄化,即使為防止圖型倒塌而輕薄被覆光阻劑之情形,亦可選擇適當的蝕刻氣體進行基板之加工。例如,可使用相對於光阻劑為具有極快蝕刻速度的氟系氣體作為蝕刻氣體,對本案發明之阻劑下層膜進行加工,又,可使用對本案發明之阻劑下層膜具有極快蝕刻速度的氧系氣體作為蝕刻氣體對有機下層膜進行加工,且可使用對有機下層膜具有極快蝕刻速度的氟系氣體作為蝕刻氣體對基板進行加工。 [0088] 本發明之阻劑下層膜上所形成的光阻劑,只要可感受曝光時所使用的光線時,並未有特別之限定。其可使用負型光阻劑及正型光阻劑中之任一者。例如,由酚醛清漆樹脂與1,2-萘醌二疊氮磺酸酯所形成的正型光阻劑、由具有經由酸而分解而提高鹼溶解速度之基的黏合劑與光酸產生劑所形成的化學增幅型光阻劑、由經由酸而分解而提高光阻劑的鹼溶解速度之低分子化合物與鹼可溶性黏合劑與光酸產生劑所形成的化學增幅型光阻劑,及由具有經由酸而分解而提高鹼溶解速度之基的黏合劑與經由酸而分解而提高光阻劑之鹼溶解速度的低分子化合物與光酸產生劑所形成的化學增幅型光阻劑等。例如,CHYPRE公司製商品名APEX-E、住友化學工業(股)製商品名PAR710,及信越化學工業(股)製商品名SEPR430等。又,例如,Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE, Vol.3999,357-364(2000)、或Proc.SPIE,Vol.3999,365-374 (2000)所記載之含氟原子聚合物系光阻劑等。 [0089] 其次,可經由特定的遮罩進行曝光。曝光,可使用KrF準分子雷射(波長248nm)、ArF準分子雷射(波長193nm)及F2準分子雷射(波長157nm)等。曝光後,必要時,可進行曝光後加熱(postexposure bake)。曝光後加熱,可於加熱溫度70℃~150℃、加熱時間0.3~10分鐘間,選擇適當的條件進行。 [0090] 又,本發明中,作為阻劑可使用電子線微影蝕刻用阻劑,或EUV微影蝕刻用阻劑來替代光阻劑。電子線阻劑可使用負型、正型中任一者皆可。例如,由酸產生劑與具有經由酸而分解而改變鹼溶解速度之基的黏合劑所形成的化學增幅型阻劑、由鹼可溶性黏合劑與酸產生劑與經由酸而分解而改變阻劑的鹼溶解速度之低分子化合物所形成的化學增幅型阻劑、由酸產生劑與具有經由酸而分解而改變鹼溶解速度之基的黏合劑與經由酸而分解而改變光阻劑的鹼溶解速度之低分子化合物所形成的化學增幅型阻劑、由具有經由電子線而分解而改變鹼溶解速度之基的黏合劑所形成的非化學增幅型阻劑、由具有可被電子線切斷而改變鹼溶解速度之部位的黏合劑所形成的非化學增幅型阻劑等。使用該些電子線阻劑之情形,其與使用照射源為電子線的光阻劑之情形為相同之方法形成阻劑圖型。 [0091] 其次,使用顯影液(例如鹼顯影液)進行顯影。如此,例如使用正型光阻劑之情形,曝光部份可經由光阻劑而去除、形成光阻劑之圖型。 [0092] 顯影液,例如,氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物水溶液、氫氧化四甲基銨、氫氧化四乙基銨、膽鹼等之氫氧化四級銨之水溶液、乙醇胺、丙胺、乙二胺等胺水溶液等的鹼性水溶液之例示。又,該些顯影液中,亦可加入界面活性劑等。顯影條件,例如,可於溫度5~50℃、時間10~600秒間適當地選擇。 [0093] 又,本案發明中,有機溶劑亦可作為顯影液使用。曝光後可使用顯影液(溶劑)進行顯影。如此,例如使用正型光阻劑之情形,可去除未曝光部份的光阻劑,而形成光阻劑圖型。 [0094] 顯影液,例如,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、二乙二醇單乙醚乙酸酯、2-甲氧基丁基乙酸酯、3-甲氧基丁基乙酸酯、4-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-乙基-3-甲氧基丁基乙酸酯、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、2-乙氧基丁基乙酸酯、4-乙氧基丁基乙酸酯、4-丙氧基丁基乙酸酯、2-甲氧基戊基乙酸酯、3-甲氧基戊基乙酸酯、4-甲氧基戊基乙酸酯、2-甲基-3-甲氧基戊基乙酸酯、3-甲基-3-甲氧基戊基乙酸酯、3-甲基-4-甲氧基戊基乙酸酯、4-甲基-4-甲氧基戊基乙酸酯、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、甲基-3-甲氧基丙酸酯、乙基-3-甲氧基丙酸酯、乙基-3-乙氧基丙酸酯、丙基-3-甲氧基丙酸酯等。又,該些顯影液中,亦可加入界面活性劑等。顯影條件,例如,可於溫度5~50℃、時間10~600秒間適當選擇。 [0095] 隨後,將依該方法所形成的光阻劑(上層)之圖型作為保護膜,以去除本發明之阻劑下層膜(中間層),其次,將圖型化之光阻劑及本發明之阻劑下層膜(中間層)所形成的膜作為保護膜,去除有機下層膜(下層)。最後,使用圖型化的本發明之阻劑下層膜(中間層)及有機下層膜(下層)作為保護膜,對半導體基板進行加工。 [0096] 首先,對去除光阻劑的部份之本發明之阻劑下層膜(中間層),進行乾蝕刻以去除,而露出半導體基板。本發明之阻劑下層膜的乾蝕刻處理,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、氮、六氟化硫、二氟甲烷、三氟化氮及三氟化氯、氯、三氯硼烷及二氯硼烷等的氣體。阻劑下層膜的乾蝕刻以使用鹵素系氣體為佳。使用鹵素系氣體之乾蝕刻,基本上不易去除由有機物質所形成的光阻劑。相對於此,含大量矽原子的本案發明之阻劑下層膜,可經由鹵素系氣體迅速地去除。因此,伴隨阻劑下層膜的乾蝕刻,可抑制光阻劑之膜厚的減少。因此,其結果可使光阻劑以薄膜形式被使用。阻劑下層膜的乾蝕刻以使用氟系氣體進行為佳,以氟系氣體,例如,四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷,及二氟甲烷(CH2
F2
)等。 [0097] 隨後,將圖型化的光阻劑及本發明之阻劑下層膜所形成的膜作為保護膜,以去除有機下層膜。有機下層膜(下層)以使用氧系氣體進行乾蝕刻去除為佳。主因為含大量矽原子的本發明之阻劑下層膜,使用氧系氣體以乾蝕刻方式難以去除。 隨後,對半導體基板進行加工。半導體基板之加工,以使用氟系氣體進行乾蝕刻為佳。 [0098] 最後進行阻劑下層膜之去除。阻劑下層膜之去除,多使用乾蝕刻或濕蝕刻處理,特別是阻劑下層膜(中間層)之乾蝕刻,以使用氟系氣體為佳。氟系氣體之例,例如,四氟甲烷(CF4
)、全氟環丁烷(C4
F8
)、全氟丙烷(C3
F8
)、三氟甲烷,及二氟甲烷(CH2
F2
)等。又,阻劑下層膜(中間層)之濕蝕刻所使用的藥液,可列舉如,氟化氫酸、緩衝氟酸(Buffered Hydrogen Fluoride)、硫酸/過氧化氫水、氨/過氧化氫水等之藥液。 [0099] 又,本發明之阻劑下層膜之上層,於光阻劑之形成前可形成有機系之抗反射膜。可使用的抗反射膜組成物,並未有特別之限制,其可由目前為止於微影蝕刻製程中慣用的組成物中任意地選擇使用,又,慣用之方法,例如,可使用旋轉塗佈機、塗佈機(Coater)進行塗佈及燒成,而形成抗反射膜。 [0100] 又,塗佈本發明之阻劑下層膜形成組成物的基板,其表面可具有由CVD法等所形成的有機系或無機系之抗反射膜者,或可於其上形成本發明之下層膜。 [0101] 本發明之阻劑下層膜形成組成物所形成的阻劑下層膜,於微影蝕刻製程中所使用的光線之波長之不同,而對於該光線具有吸收。因此,於該情形中,其具有防止基板產生反射光效果的抗反射膜之機能。又,本發明之下層膜,亦可作為防止基板與光阻劑產生相互作用之層、作為具有防止光阻劑所使用之材料或光阻劑於曝光時所生成的物質對基板產生不良作用的機能之層、作為具有防止加熱燒成時基板產生之物質擴散至上層光阻劑的機能之層,及作為降低因半導體基板介電體層對光阻劑層造成毒害效果之阻隔層等的用途。 [0102] 又,由阻劑下層膜形成組成物所形成的阻劑下層膜,適用於形成有雙鑲嵌(Dual Damascene)製程所得之形成通孔(viahole)之基板,其可使用作為可將孔洞無間隙填充埋入之材料。又,為使凹凸的半導體基板表面平坦化,亦可作為平坦化材料使用。 又,EUV阻劑之下層膜,亦可使用於作為硬遮罩機能以外的以下之目的。上述阻劑下層膜形成組成物不會與EUV阻劑產生內部混合(inter mixing),故可作為防止EUV曝光(波長13.5nm)時之不良曝光光線,例如上述UV或DUV(ArF光、KrF光)由基板或界面產生反射的EUV阻劑的下層抗反射膜。而使EUV阻劑的下層有效率地防止反射。作為EUV阻劑下層膜使用時,該製程可依與光阻劑用下層膜為相同之方法進行。
[實施例] [0103] (合成例1) 將35質量%濃度氫氧化四乙基銨水溶液1.81g、水2.89g、異丙醇47.59g、甲基異丁酮95.17g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將苯基三甲氧基矽烷4.27g、甲基三乙氧基矽烷11.51g、環己基環氧乙基三甲氧基矽烷31.81g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷60莫耳%。 添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,將1M硝酸107.59g加入反應溶液中,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮285.52g、水142.76g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚142.76g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-1),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2500,環氧價為0。 [0104] (合成例2) 將35質量%濃度的氫氧化四乙基銨水溶液1.61g、水2.57g、異丙醇46.45g、甲基異丁酮92.90g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯7.92g、甲基三乙氧基矽烷10.24g、環己基環氧乙基三甲氧基矽烷28.30g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷60莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中加入1M硝酸95.70g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮278.69g、水139.35g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚139.35g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-2),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2700,環氧價為0。 [0105] (合成例3) 將35質量%濃度的氫氧化四乙基銨水溶液1.48g、水2.36g、異丙醇39.50g、甲基異丁酮79.00g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯7.27g、甲基三乙氧基矽烷6.27g、環己基環氧乙基三甲氧基矽烷25.97g、乙氧基乙氧基苯基三甲氧基矽烷5.03g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷60莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸87.84g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮237.01g、水118.51g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚118.51g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-3),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2400,環氧價為0。 [0106] (合成例4) 將35質量%濃度的氫氧化四乙基銨水溶液1.52g、水2.43g、異丙醇40.55g、甲基異丁酮81.10g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯7.46g、甲基三乙氧基矽烷6.43g、環己基環氧乙基三甲氧基矽烷26.66g、甲氧基苄基三甲氧基矽烷4.37g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷60莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸90.17g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮243.29g、水121.65g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚121.65g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-4),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2600,環氧價為0。 [0107] (合成例5) 將35質量%濃度的氫氧化四乙基銨水溶液1.61g、水2.57g、異丙醇41.20g、甲基異丁酮82.39g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯7.92g、甲基三乙氧基矽烷6.83g、環己基環氧乙基三甲氧基矽烷9.43g、乙氧基乙氧基苯基三甲氧基矽烷5.48g、乙醯氧基丙基三甲氧基矽烷17.02g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸95.71g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮247.17g、水123.59g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚123.59g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-5),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2800,環氧價為0。 [0108] (合成例6) 將35質量%濃度的氫氧化四乙基銨水溶液1.68g、水2.69g、異丙醇44.19g、甲基異丁酮88.38g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯8.28g、甲基三乙氧基矽烷7.14g、環己基環氧乙基三甲氧基矽烷9.86g、乙氧基乙氧基苯基三甲氧基矽烷5.73g、乙醯氧基甲基三乙氧基矽烷18.92g滴入混合溶液中。於全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸100.06g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮265.15g、水132.58g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚132.58g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-6),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2800,環氧價為0。 [0109] (合成例7) 將35質量%濃度的氫氧化四乙基銨水溶液1.61g、水2.58g、異丙醇45.73g、甲基異丁酮91.47g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯7.93g、甲基三乙氧基矽烷3.42g、環己基環氧乙基三甲氧基矽烷9.45g、乙氧基乙氧基苯基三甲氧基矽烷5.49g、乙醯氧基甲基三乙氧基矽烷18.13g、雙(三乙氧矽烷基)乙烷6.80g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸95.90g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮274.41g、水137.20g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚137.20g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-7),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw4300,環氧價為0。 [0110] (合成例8) 將35質量%濃度的氫氧化四乙基銨水溶液1.70g、水2.72g、異丙醇45.82g、甲基異丁酮91.65g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯8.35g、四乙氧基矽烷8.42g、環己基環氧乙基三甲氧基矽烷9.95g、乙氧基乙氧基苯基三甲氧基矽烷5.79g、乙醯氧基甲基三乙氧基矽烷19.10g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸101.01g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮274.95g、水137.47g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚137.47g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-8),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw3800,環氧價為0。 [0111] (合成例9) 將35質量%濃度的氫氧化四乙基銨水溶液1.72g、水2.75g、異丙醇46.04g、甲基異丁酮92.08g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯8.47g、四乙氧基矽烷8.53g、環氧丙氧基丙基三甲氧基矽烷9.98g、乙氧基乙氧基苯基三甲氧基矽烷5.87g、乙醯氧基甲基三乙氧基矽烷19.36g滴入混合溶液中。使全水解性矽烷中含有環氧丙氧基丙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸102.39g,再於40℃下,使環氧丙氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮276.25g、水138.12g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚138.12g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-9),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2800,環氧價為0。 [0112] (合成例10) 將35質量%濃度的氫氧化四乙基銨水溶液1.77g、水2.82g、異丙醇44.88g、甲基異丁酮89.76g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將(2-甲氧基-4-(甲氧基甲基)苯氧基)甲基三乙氧基矽烷7.23g、甲基三乙氧基矽烷7.48g、環己基環氧乙基三甲氧基矽烷10.34g、乙氧基乙氧基苯基三甲氧基矽烷6.01g、乙醯氧基甲基三乙氧基矽烷19.83g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸104.89g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮274.95g、水137.47g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚137.47g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(1),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw3000,環氧價為0。 [0113] (合成例11) 35質量%濃度的氫氧化四乙基銨水溶液1.35g、水2.16、異丙醇41.39g、甲基異丁酮82.79g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯6.64g、甲基三乙氧基矽烷5.73g、環己基環氧乙基三甲氧基矽烷7.92g、乙氧基乙氧基苯基三甲氧基矽烷4.60g、5-(三乙氧矽烷基)六氫-4,7-甲氧基異苯併呋喃(methanol isobenzofuran)‐1,3-二酮21.10g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸80.32g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮248.36g、水124.18g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚124.18g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-11),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2400,環氧價為0。 [0114] (合成例12) 將35質量%濃度的氫氧化四乙基銨水溶液1.26g、水2.01g、異丙醇40.62g、甲基異丁酮81.23g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯6.19g、甲基三乙氧基矽烷5.34g、環己基環氧乙基三甲氧基矽烷7.38g、乙氧基乙氧基苯基三甲氧基矽烷4.29g、2,2,5-三甲基-5-(3-(三乙氧矽烷基)丙基)-1,3-二噁烷-4,6-二酮21.71g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸74.86g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮243.70g、水121.85g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚121.85g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-12),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2600,環氧價為0。 [0115] (合成例13) 將35質量%濃度的氫氧化四乙基銨水溶液1.37g、水2.19g、異丙醇41.52g、甲基異丁酮83.04g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將(雙環(2,2,1)庚-5-烯-基)三乙氧基矽烷4.17g、甲基三乙氧基矽烷5.79g、環己基環氧乙基三甲氧基矽烷8.01g、乙氧基乙氧基苯基三甲氧基矽烷4.65g、2,2,5-三甲基-5-(3-(三乙氧矽烷基)丙基)-1,3-二噁烷-4,6-二酮23.56g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸74.86g,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮243.70g、水121.85g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚121.85g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-13),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2800,環氧價為0。 [0116] (合成例14) 將35質量%濃度的氫氧化四乙基銨水溶液1.63g、水2.61g、異丙醇40.51g、甲基異丁酮81.01g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將苯基磺醯基丙基三乙氧基矽烷6.73g、甲基三乙氧基矽烷6.93g、環己基環氧乙基三甲氧基矽烷9.57g、乙氧基乙氧基苯基三甲氧基矽烷5.56g、乙醯氧基丙基三甲氧基矽烷17.27g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸97.13,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮243.04g、水121.52g,進行分液操作,並將移動至水層的反應副產物之水、硝酸、四乙基銨硝酸鹽餾除後,回收有機層。隨後,加入丙二醇單甲醚121.52g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-14),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2300,環氧價為0。 [0117] (合成例15) 將35質量%濃度的氫氧化四乙基銨水溶液1.70g、水2.72g、異丙醇45.82g、甲基異丁酮91.65g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將三乙氧矽烷基丙基二烯丙基異三聚氰酸酯8.35g、四乙氧基矽烷8.42g、環己基環氧乙基三甲氧基矽烷9.95g、乙氧基乙氧基苯基三甲氧基矽烷5.79g、乙醯氧基甲基三乙氧基矽烷19.10g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷20莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中加入陽離子交換樹脂30g,於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入陰離子交換樹脂60g。隨後,將陽離子交換樹脂、陰離子交換樹脂使用尼龍網孔過濾器餾除後,加入丙二醇單甲醚137.47g後,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(A-15),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw6000,環氧價為0。 [0118] (比較合成例1) 將35質量%濃度氫氧化四乙基銨水溶液1.81g、水2.89g、異丙醇47.59g、甲基異丁酮95.17g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將苯基三甲氧基矽烷4.27g、甲基三乙氧基矽烷11.51g、環己基環氧乙基三甲氧基矽烷31.81g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷60莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,加入甲基異丁酮285.52g、水142.76g,進行分液操作,餾除移動至水層的反應副產物之水、氫氧化四乙基銨後,回收有機層。隨後,加入丙二醇單甲醚142.76g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(B-1),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw2300,由環氧價得知該環氧基為殘留95%以上。[0119] (比較合成例2) 將35質量%濃度的氫氧化四乙基銨水溶液3.20g、水5.12g、異丙醇69.91g、甲基異丁酮139.81g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將苯基三甲氧基矽烷7.55g、甲基三乙氧基矽烷57.67g、環己基環氧乙基三甲氧基矽烷4.69g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷5莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M硝酸190.27,再於40℃下使環己基環氧基進行開環反應,而製得具有二羥基之水解縮合物。隨後,加入甲基異丁酮419.44g、水209.72g,進行分液操作,餾除移動至水層的反應副產物之水、氫氧化四乙基銨後,回收有機層。隨後,加入丙二醇單甲醚209.72g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(B-2),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw4000,環氧價為0。[0120] (比較合成例3) 將35質量%濃度的氫氧化四乙基銨水溶液2.96g、水4.73g、異丙醇66.01g、甲基異丁酮132.02g置入1000ml之燒瓶中,使用磁性攪拌子攪拌混合溶液的同時,將苯基三甲氧基矽烷7.35g、甲基三乙氧基矽烷49.54g、環己基環氧乙基三甲氧基矽烷9.13g滴入混合溶液中。使全水解性矽烷中含有環己基環氧乙基三甲氧基矽烷10莫耳%。添加後,將燒瓶移入調整至40℃的油浴中,進行240分鐘之反應。隨後,於反應溶液中,加入1M乙酸175.96g,再於40℃下,使環己基環氧基進行開環反應,而製得具有乙醯氧基與單羥基之水解縮合物。隨後,加入甲基異丁酮396.05g、水198.03g,進行分液操作,餾除移動至水層的反應副產物之水、氫氧化四乙基銨後,回收有機層。隨後,加入丙二醇單甲醚198.03g,將甲基異丁酮、甲醇、乙醇、水減壓餾除,製得濃縮之水解縮合物(聚合物)水 溶液。再加入丙二醇單乙醚,將其調整至丙二醇單甲醚100%的溶劑比例下,於140℃下的固形殘物換算為20質量百分比。所得聚合物相當於式(B-3),依GPC所測得之聚苯乙烯換算的重量平均分子量為Mw3800,環氧價為0。[0121] (含Si的阻劑下層膜之製作) 將上述合成例1~15,及比較合成例1~3所得之水解縮合物(Si聚合物)、酸、溶劑,依表1所示比例混合,經0.1μm的氟樹脂製過濾器過濾後,分別製得阻劑下層膜形成組成物。表1中之聚合物的添加比例並非聚合物溶液的添加量,而為聚合物本身的添加量。 [0122] 下表中,PPTS表示吡啶鎓-p-甲苯磺酸。商品名TAG-2689為King Industries公司製之熱酸產生劑(成份為三氟磺酸酯之銨鹽。交聯性化合物PL-LI為三井科技(股)製、商品名Powerlink 1174之四甲氧基甲基乙炔脲。交聯性化合物為本州化學工業(股)製之商品名TMOM-BP為式(4-22)的化合物,旭有機材工業(股)、商品名TM-BIP-A為式(4-21)之化合物。PGME為丙二醇單甲醚,PGMEA為丙二醇單甲醚乙酸酯。 [0123] (有機下層膜之製造) 於氮氣氛圍下,將咔唑(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)、對甲苯磺酸一水和物(0.76g、0.0040mol、東京化成工業(股)製)加入100mL四口燒瓶中,再加入1,4-二噁烷(6.69g、關東化學(股)製)後進行攪拌,升溫至100℃,使其溶解開始聚合。於24小時後,放冷至60℃後,加入氯仿(34g、關東化學(股)製)稀釋,使其於甲醇(168g、關東化學(股)製)再沈澱。將所得沈澱物過濾,使用減壓乾燥機,於80℃下進行24小時乾燥,得到目的聚合物(式(C-1))、以下,簡稱PCzFL)9.37g。[0124] PCzFL的1
H-NMR測定結果係如以下所示。1
H-NMR(400MHz, DMSO-d6
):δ7.03-7.55(br, 12H), δ7.61-8.10(br, 4H), δ11.18(br, 1H) PCzFL使用GPC測定之聚苯乙烯換算的重量平均分子量Mw為2800、多分散度(polydispersity)Mw/Mn為1.77。 將所得之樹脂20g,與作為交聯劑之四甲氧基甲基乙炔脲(三井科技(股)製、商品名Powerlink 1174)3.0g、作為觸媒之吡啶鎓對甲苯磺酸酯0.30g、作為界面活性劑之美格氟R-30(大日本塗料化學(股)製、商品名)0.06g混合,使其溶解於丙二醇單甲醚乙酸酯88g中,形成溶液。隨後,使用孔徑0.10μm的聚乙烯製微過濾器過濾,再使用孔徑0.05μm的聚乙烯製微過濾器過濾,而製得多層膜中之微影蝕刻製程所使用的有機下層膜形成組成物之溶液。 [0125] (溶劑耐性試驗) 將實施例1~18、比較例1~3所製得之阻劑下層膜形成組成物,使用旋轉塗佈機,塗佈於矽晶圓上。於加熱板上進行180℃、1分鐘之加熱,分別形成含Si的阻劑下層膜。隨後,將丙二醇單甲醚/丙二醇單甲醚乙酸酯=7/3的溶劑塗佈於含Si的阻劑下層膜上,經旋轉乾燥,並依圖型形狀評估溶劑塗佈前後有無膜厚變化。膜厚變化未達1%者標記為「良好」、膜厚變化為1%以上者,則標記為「未硬化」。[0126] 上述評估中,膜厚變化為1%以上,而被標記為「未硬化」時,如比較例1至比較例3之膜厚變化為1%以上,故未能進行充份的硬化,而會使上層所被覆的阻劑之溶劑產生溶解而對阻劑層造成不良影響之可能性。但,比較例1至比較例3仍進行隨後的阻劑圖型之評估。 [0127] (乾蝕刻速度之測定) 乾蝕刻速度之測定所使用的蝕刻機及蝕刻氣體,為使用以下之內容。 ES401(日本Scientific製):CF4
RIE-10NR(Sumco製):O2
將實施例1~18所製得的含Si的塗佈液,使用旋轉塗佈機塗佈於矽晶圓上。於加熱板進行180℃、1分鐘之加熱,分別形成含Si的阻劑下層膜(膜厚0.1μm(供CF4
氣體蝕刻速度測定用)、膜厚0.1μm(供O2
氣體蝕刻速度測定用))。 蝕刻氣體為使用CF4
氣體、O2
氣體,測定乾蝕刻速度。[0128] 〔ArF曝光之阻劑圖型評估〕 (阻劑圖型形成(Patterning)之評估:於鹼顯影中經由PTD步驟之評估) 將上述所得有機下層膜(A層)形成組成物塗佈於矽晶圓上,於加熱板上進行240℃、60秒鐘之燒焙,製得膜厚200nm之有機下層膜(A層)。將實施例1~18、比較例1~3所得之含Si的阻劑下層膜(B層)形成組成物分別塗佈於其上,於加熱板上進行240℃、60秒鐘之燒焙,製得含Si的阻劑下層膜(B層)。含Si的阻劑下層膜(B層)之膜厚為80nm。 將市售的ArF用阻劑溶液(JSR(股)製、商品名:AR2772JN),使用旋轉塗佈機分別塗佈於各個B層上,於加熱板上進行110℃、1分鐘之加熱,形成膜厚120nm之光阻劑膜(C層)。 使用(股)尼康製NSR-S307E掃描器(波長193nm、NA、σ:0.85、0.93/0.85),使用設定有顯影後的光阻劑之線路寬及其線路間之寬度形成為0.062μm,即0.062μm之線路與空間(L/S)=1/1之線密度(Dense line)的遮罩,對各個層合體進行曝光。隨後,於加熱板上進行100℃、60秒鐘之燒焙,冷卻後,使用2.38質量%濃度的鹼水溶液,進行60秒顯影,於阻劑下層膜(B層)上形成正型的圖型。對所得的光阻劑圖型中,未發生較大圖型剝落或底切(Undercut)、線路底部肥大(Footing)時,評估為「良好」。阻劑圖型產生倒塌時,則評估為「圖型倒塌」。[0129] 〔SPM藥液對阻劑下層膜之去除性的評估〕 將實施例1~18、比較例1所製得之阻劑下層膜形成組成物,使用旋轉塗佈機,塗佈於矽晶圓上。於加熱板上進行180℃、1分鐘之加熱,分別形成阻劑下層膜。隨後,使用Rasa工業製RS-30(硫酸・過氧化氫混合水:SPM藥液)塗佈於阻劑下層膜上之後,進行水洗滌,再進行旋轉乾燥後,評估SPM藥液塗佈前後之膜厚有無產生變化。膜厚變化為90%以上時,標記為「良好」,膜厚變化未達90%時,則評估為「無溶解」。「無溶解」,於本發明中為不良之結果。[產業上利用性] [0130] 本發明提供一種微影蝕刻步驟中,可作為硬遮罩使用的阻劑下層膜,其可使用藥液的濕式法、特別是可使用SPM(硫酸與過氧化氫水之混合水溶液)去除的含矽阻劑下層膜。
Claims (13)
- 一種阻劑下層膜形成組成物,其為含有包含具有二羥基之有機基的水解縮合物的阻劑下層膜形成組成物,其特徵為, 前述包含具有二羥基之有機基的水解縮合物中之二羥基為,由包含具有環氧基之有機基的水解縮合物中之該環氧基,經無機酸或陽離子交換樹脂進行開環反應而生成者, 前述包含具有環氧基之有機基的水解縮合物為,於含有相對於全水解性矽烷為基準為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷,經鹼性物質水溶液而得之水解縮合物。
- 如請求項1之阻劑下層膜形成組成物,其中,上述含有相對於全水解性矽烷為基準為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷為包含式(1)所示之水解性矽烷:(式(1)中,R1 為環己基環氧基、環氧丙氧烷基,或包含該些之有機基,且經Si-C鍵結而與矽原子鍵結者;R2 為烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、醯氧烷基,或具有丙烯醯基、甲基丙烯醯基、氫硫基、胺基、醯胺基、羥基、烷氧基、酯基、磺醯基,或氰基之有機基,或為該些之組合,且經Si-C鍵結而與矽原子鍵結者;R3 表示烷氧基、醯氧基,或鹵素基;a表示1之整數,b表示0~2之整數,a+b表示1~3之整數)。
- 如請求項2之阻劑下層膜形成組成物,其中,上述含有相對於全水解性矽烷為基準為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷,除式(1)之水解性矽烷以外,尚包含由式(2)及式(3)所成之群所選出之至少1種的水解性矽烷;(式(2)中,R4 為烷基、芳基、鹵化烷基、鹵化芳基、烷氧基芳基、烯基、醯氧烷基,或具有丙烯醯基、甲基丙烯醯基、氫硫基、胺基、醯胺基、羥基、烷氧基、酯基、磺醯基,或氰基之有機基,或為該些之組合,且經Si-C鍵結而與矽原子鍵結者,R5 表示烷氧基、醯氧基,或鹵素基,c表示0~3之整數)(式(3)中,R6 為烷基,且經Si-C鍵結而與矽原子鍵結者,R7 表示烷氧基、醯氧基,或鹵素基,Y表示伸烷基或伸芳基,d表示0或1之整數,e為0或1之整數)。
- 如請求項2或請求項3之阻劑下層膜形成組成物,其中,式(1)之水解性矽烷,依全水解性矽烷為基準,為含有10~90莫耳%之比例。
- 如請求項1至請求項4中任一項之阻劑下層膜形成組成物,其尚包含交聯性化合物。
- 如請求項1至請求項5中任一項之阻劑下層膜形成組成物,其尚包含酸或酸產生劑。
- 如請求項1至請求項6中任一項之阻劑下層膜形成組成物,其尚包含水。
- 如請求項1至請求項7中任一項之阻劑下層膜形成組成物,其中,前述水解性矽烷於鹼性物質水溶液中生成水解縮合物,與前述環氧基經無機酸或陽離子交換樹脂所進行的開環反應皆於有機溶劑中進行。
- 一種阻劑下層膜,其為將請求項1至請求項8中任一項之阻劑下層膜形成組成物塗佈於基板,並經燒成後而得的阻劑下層膜,其特徵為,該阻劑下層膜可經由包含具有1:1~4:1的H2 SO4 /H2 O2 之質量比的硫酸與過氧化氫之水溶液而去除。
- 一種如請求項1至請求項8中任一項之阻劑下層膜形成組成物的製造方法,其特徵為包含: 於含有相對於全水解性矽烷為基準為10~90莫耳%之比例的具有環氧基之水解性矽烷的水解性矽烷中,經鹼性物質水溶液進行水解縮合,而製得包含具有環氧基之有機基的水解縮合物之步驟,及 於包含該包含具有環氧基之有機基的水解縮合物的反應系中,再以無機酸或陽離子交換樹脂使該環氧基進行開環反應,而製得包含具有二羥基之有機基的水解縮合物之步驟。
- 一種半導體裝置的製造方法,其特徵為包含: 將請求項1至請求項8中任一項之阻劑下層膜形成組成物塗佈於半導體基板上,經燒成而形成阻劑下層膜之步驟、 將阻劑用組成物塗佈於前述下層膜上而形成阻劑膜之步驟、 使前述阻劑膜曝光之步驟、 於曝光後使阻劑進行顯影,而製得阻劑圖型之步驟、 依阻劑圖型而對阻劑下層膜進行蝕刻之步驟,及 藉由經圖型化的阻劑與阻劑下層膜對半導體基板進行加工之步驟。
- 一種半導體裝置的製造方法,其特徵為包含: 於半導體基板上形成有機下層膜之步驟、 將請求項1至請求項8中任一項之阻劑下層膜形成組成物塗佈於其上,進行燒成而形成阻劑下層膜之步驟、 將阻劑用組成物塗佈於前述阻劑下層膜上,而形成阻劑層之步驟、 使前述阻劑膜曝光之步驟、 於曝光後使阻劑進行顯影,而製得阻劑圖型之步驟、 依阻劑圖型而對阻劑下層膜進行蝕刻之步驟、 藉由經圖型化之阻劑下層膜對有機下層膜進行蝕刻之步驟,及 藉由經圖型化之有機下層膜對半導體基板進行加工之步驟。
- 如請求項11或請求項12之半導體裝置的製造方法,其尚包含使用含有硫酸與過氧化氫之水溶液去除經圖型化的阻劑下層膜之步驟。
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