TW202232239A - 含矽之阻劑下層膜形成用組成物以及圖案形成方法 - Google Patents
含矽之阻劑下層膜形成用組成物以及圖案形成方法 Download PDFInfo
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- YUVZWFKROIQRKD-UHFFFAOYSA-N silane triethoxysilane Chemical compound [SiH4].CCO[SiH](OCC)OCC YUVZWFKROIQRKD-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical class C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- MQVCTPXBBSKLFS-UHFFFAOYSA-N tri(propan-2-yloxy)-propylsilane Chemical compound CCC[Si](OC(C)C)(OC(C)C)OC(C)C MQVCTPXBBSKLFS-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-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
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
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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
- G03F7/20—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
- G03F7/2006—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 using coherent light; using polarised light
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/322—Aqueous alkaline compositions
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- G03F7/38—Treatment before imagewise removal, e.g. prebaking
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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
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02115—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 being carbon, e.g. alpha-C, diamond or hydrogen doped carbon
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- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
- H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
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- 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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- H01L21/027—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
- H01L21/0331—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers for lift-off processes
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- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
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- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
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- 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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Abstract
Description
本發明關於含矽之阻劑下層膜形成用組成物、及使用該組成物的圖案形成方法。
伴隨大型積體電路(LSI)的高積體化與高速化,圖案尺寸的微細化正急速進展。微影技術,伴隨該微細化,藉由光源之短波長化及適當選擇與其對應的阻劑組成物,已達成微細圖案的形成。成為其中心的是以單層使用之正型光阻劑組成物。該單層正型光阻劑組成物,係藉由使阻劑樹脂中具有對於利用氯系或氟系氣體電漿所為之乾蝕刻具蝕刻耐性之骨架,且具有曝光部會溶解之類的開關(switching)機制,而使曝光部溶解來形成圖案,並將殘存的阻劑圖案作為蝕刻遮罩對被加工基板進行乾蝕刻加工。
然而,於維持所使用之光阻劑膜之膜厚的狀態進行微細化,亦即將圖案寬進一步縮小時,光阻劑膜之解析性能降低,又,欲利用顯影液對光阻劑膜進行圖案顯影的話,會發生所謂縱橫比變得過大,結果造成圖案崩壞的問題。因此,伴隨圖案的微細化,光阻劑膜也逐漸薄膜化。
另一方面,被加工基板的加工,通常使用將形成有圖案之光阻劑膜作為蝕刻遮罩,並利用乾蝕刻對基板進行加工的方法,但現實中並不存在能於光阻劑膜與被加工基板之間取得完全的蝕刻選擇性的乾蝕刻方法。因此,會有在基板的加工中,阻劑膜也受到損傷而崩壞,且阻劑圖案變得無法正確地轉印至被加工基板的問題。因此,伴隨圖案的微細化,光阻劑組成物亦逐漸尋求更高的乾蝕刻耐性。但是,另一方面,為了提高解析度,光阻劑組成物所使用之樹脂已逐漸尋求在曝光波長的光吸收小的樹脂。因此,隨著曝光光短波長化為i射線、KrF、ArF,光阻劑組成物所使用的樹脂也逐漸變化成酚醛清漆樹脂、具有多羥基苯乙烯、脂肪族多環狀骨架之樹脂,但現實中基板加工時的乾蝕刻條件下之蝕刻速度逐漸變快,解析度高之最近的光阻劑組成物反而會有蝕刻耐性變弱的傾向。
考量此情形,變得必須以較薄且蝕刻耐性較弱的光阻劑膜對被加工基板進行乾蝕刻加工,確保該加工步驟中的材料及處理已成為當務之急。
作為解決如此之問題的方法之一,有多層阻劑法。該方法係將蝕刻選擇性與光阻劑膜(亦即,阻劑上層膜)不同的下層膜插入在阻劑上層膜與被加工基板之間,在阻劑上層膜獲得圖案後,將阻劑上層膜圖案作為乾蝕刻遮罩,利用乾蝕刻將圖案轉印至下層膜,進一步,將下層膜作為乾蝕刻遮罩,利用乾蝕刻將圖案轉印至被加工基板的方法。
作為多層阻劑法之一,有可使用單層阻劑法中所使用之一般的阻劑組成物來實施的3層阻劑法。該3層阻劑法中,例如係於被加工基板上將酚醛清漆樹脂等構成之有機膜予以成膜,於其上將含矽之阻劑下層膜予以成膜,再於上形成通常的有機系光阻劑膜作為阻劑上層膜。實施利用氟系氣體電漿所為之乾蝕刻時,有機系阻劑上層膜相對於含矽之阻劑下層膜可取得良好的蝕刻選擇比,故阻劑上層膜圖案可利用氟系氣體電漿所為之乾蝕刻而轉印至含矽之阻劑下層膜。根據該方法,即使使用難以形成具有用以直接對被加工基板進行加工所需之充分膜厚之圖案的阻劑組成物、不具有基板的加工所需之充分乾蝕刻耐性的阻劑組成物,亦可將圖案轉印至含矽膜(阻劑下層膜),然後利用氧系或氫系氣體電漿所為之乾蝕刻實施圖案轉印,則可獲得具有基板之加工所需之充分乾蝕刻耐性之酚醛清漆樹脂等構成的有機膜的圖案。形成有機膜圖案後所殘留的含矽之阻劑下層膜,通常利用氟系氣體電漿所為之乾蝕刻、或鹼系、氟系等蝕刻液所為之濕式蝕刻,以不成為造成缺陷的原因之殘渣的方式予以去除。蝕刻速度不足時,發生來自含矽之阻劑下層膜的殘渣殘留而成為缺陷、或需要進行長時間的蝕刻處理而對被加工基板造成損傷等問題的可能性提高。如此,為了正確的圖案化、及順利的去除,含矽之阻劑下層膜需要適當的蝕刻速度。
另一方面,近年由於ArF浸潤式微影、EUV微影等的出現,逐漸可形成更微細的圖案,但另一方面,超微細圖案由於接地面積小,故極易崩塌,圖案形狀的改善與圖案崩塌的抑制係非常大的課題。因此,抑制圖案崩塌的效果高的含矽之阻劑下層膜的開發成為當務之急。
為了改善圖案崩塌,有人提出於矽氧烷結構之側鏈結構導入了具有密接性、熱硬化觸媒功能等效果之取代基的ArF或EUV微影用含矽之阻劑下層膜形成用組成物(專利文獻1、2)。藉由該等的導入而抑制圖案崩塌的效果得到改善,但在使用了EUV微影等之更進一步微細化之最先進的用途中,圖案崩塌依然係重大的課題。
[先前技術文獻]
[專利文獻]
[專利文獻1]WO2020/085508號
[專利文獻2]WO2020/196563號
[發明所欲解決之課題]
本發明旨在提供於多層阻劑法中,抑制超微細圖案崩塌的效果高,可形成圖案形狀良好之阻劑圖案的含矽之阻劑下層膜。
[解決課題之手段]
為了解決上述課題,本發明提供一種含矽之阻劑下層膜形成用組成物,含有下列通式(A-1)表示之化合物及熱交聯性聚矽氧烷。
[化1]
R
1表示甲基、乙基、丙基、烯丙基、炔丙基,R
2表示氫原子、乙醯基、丙烯醯基、甲基丙烯醯基、苯甲醯基、萘甲醯基、蒽甲醯基,R
3表示甲基、乙基、丙基、烯丙基、炔丙基、或下列通式(A-2)表示之基。
[化2]
虛線表示原子鍵,R
1、R
2與前述相同。
在半導體裝置製程中使用之使用了ArF或EUV等紫外線雷射的微影步驟中,藉由使用由含有具有通式(A-1)表示之異氰尿酸結構之化合物的本發明之組成物形成的含矽之阻劑下層膜,可對形成於其上之光阻劑圖案賦予良好的密接性。
前述熱交聯性聚矽氧烷宜含有下列通式(Sx-1)表示之重複單元、下列通式(Sx-2)表示之重複單元、及下列通式(Sx-3)表示之次結構中之任一者以上。
[化3]
[化4]
[化5]
式中,R
4、R
5、R
6可各自相同亦可不同地為碳數1~30之1價有機基。
上述熱交聯性聚矽氧烷(Sx)含有上述特定結構時,會更充分地發揮本發明之效果。
宜更含有酸產生劑。
藉由視需要添加酸產生劑,可對圖案形狀、曝光感度等進行微調整。
前述酸產生劑宜為係鋶鹽且會因高能量射線之作用而產生酸的光酸產生劑較佳。
此時,可將其他性能的降低壓抑為最小限度,同時可適度調整阻劑上層膜之圖案形狀、曝光感度等,且有時於減少來自阻劑上層膜之殘渣亦係有效。
又,本發明提供一種圖案形成方法,係於被加工體形成圖案的方法,包含下列步驟:
於被加工體上使用塗布型有機膜材料來形成有機膜;
於前述有機膜上使用上述含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜;
於前述含矽之阻劑下層膜上使用由光阻劑組成物構成之阻劑上層膜用組成物來形成阻劑上層膜;
於前述阻劑上層膜形成電路圖案;
將形成有前述電路圖案之前述阻劑上層膜作為遮罩,利用蝕刻將圖案轉印至前述含矽之阻劑下層膜;
將轉印有前述圖案之前述含矽之阻劑下層膜作為遮罩,利用蝕刻對前述有機膜進行圖案轉印;及
將轉印有前述圖案之前述有機膜作為遮罩,利用蝕刻將圖案轉印至前述被加工體。
又,本發明提供一種圖案形成方法,係於被加工體形成圖案的方法,包含下列步驟:
於被加工體上利用CVD法形成以碳作為主成分之硬遮罩;
於前述硬遮罩上使用上述含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜;
於前述含矽之阻劑下層膜上使用由光阻劑組成物構成之阻劑上層膜用組成物來形成阻劑上層膜;
於前述阻劑上層膜形成電路圖案;
將前述形成有電路圖案之阻劑上層膜作為遮罩,利用蝕刻將圖案轉印至前述含矽之阻劑下層膜;
將轉印有前述圖案之前述含矽之阻劑下層膜作為遮罩,利用乾蝕刻對前述硬遮罩進行圖案轉印;及
將轉印有前述圖案之前述硬遮罩作為遮罩,利用乾蝕刻將圖案轉印至前述被加工體。
上述圖案形成方法可抑制阻劑上層膜之圖案崩塌,且可提供良好的阻劑圖案。又,利用乾蝕刻所為之朝含矽之阻劑下層膜之圖案轉印優異,且圖案化結束後所殘存的含矽之阻劑下層膜之去除容易,不易產生因殘渣所致之缺陷,故尤其於微細圖案之形成係實用的圖案形成方法。
於前述阻劑上層膜形成電路圖案的步驟中之圖案形成,宜利用波長為10nm以上300nm以下之光微影、電子束所為之直接描繪、奈米壓印或它們的組合來形成圖案較佳。
上述阻劑上層膜之圖案形成方法為上述特定的圖案形成方法時,會更充分地發揮本發明之效果。
前述被加工體宜為半導體裝置基板、金屬膜、金屬碳化膜、金屬氧化膜、金屬氮化膜、金屬氧化碳化膜或金屬氧化氮化膜。
被加工體為上述特定者時,會更充分地發揮本發明之效果。
另外,構成前述被加工體之金屬宜為矽、鎵、鈦、鎢、鉿、鋯、鉻、鍺、銅、銀、金、銦、砷、鈀、鉭、銥、鋁、鐵、鉬、鈷或它們的合金。
構成被加工體之金屬為上述特定的金屬時,會更充分地發揮本發明之效果。
[發明之效果]
使用了含有具有多個異氰尿酸結構之化合物的本發明之含矽之阻劑下層膜形成用組成物的含矽之阻劑下層膜,可無崩塌地形成超微細的上層阻劑圖案,不僅如此,還可形成良好的圖案形狀。又,阻劑上層膜與有機膜或與硬遮罩之乾蝕刻選擇性優異,故能以良好產能於基板形成半導體裝置用圖案。另外,使用了本發明之含矽之阻劑下層膜形成用組成物的含矽之阻劑下層膜,可在與有機材料之間獲得高蝕刻選擇性,故可將形成的光阻劑圖案利用乾蝕刻處理依序轉印至含矽之阻劑下層膜、有機膜或硬遮罩。又,本發明中,形成的含矽之阻劑下層膜具有充分的蝕刻速度,故圖案化結束後所殘存的含矽之阻劑下層膜之去除容易,不易產生因殘渣所致之缺陷,因而於微細圖案的形成係尤其有用。
本發明係關於用以形成半導體元件等之製造步驟中之微影所使用之塗布型含矽膜的組成物及使用了該組成物之圖案形成方法。
如前述,尋求能提供於多層阻劑法中,抑制超微細圖案崩塌的效果高,且可形成良好之阻劑圖案,具有適當蝕刻速度之含矽之阻劑下層膜的含矽之阻劑下層膜形成用組成物、及使用了該組成物之超微細圖案形成方法。
本案發明人等為了達成前述目的而進行努力研究的結果,發現藉由將具有特定結構之異氰尿酸結構的化合物摻合至含矽之阻劑下層膜形成用組成物中,能提供於多層阻劑法中可抑制超微細圖案的崩塌,且可形成良好的阻劑圖案,而且具有適合加工之蝕刻速度的含矽之阻劑下層膜,而完成了本發明。
亦即,本發明係一種含矽之阻劑下層膜形成用組成物,含有下列通式(A-1)表示之化合物及熱交聯性聚矽氧烷。
[化6]
R
1表示甲基、乙基、丙基、烯丙基、炔丙基,R
2表示氫原子、乙醯基、丙烯醯基、甲基丙烯醯基、苯甲醯基、萘甲醯基、蒽甲醯基,R
3表示甲基、乙基、丙基、烯丙基、炔丙基、或下列通式(A-2)表示之基。
[化7]
虛線表示原子鍵,R
1、R
2與前述相同。
以下,針對本發明詳細地說明,但本發明不限定於該等。
<含矽之阻劑下層膜形成用組成物>
本發明之含矽之阻劑下層膜形成用組成物,其特徵為含有:下列通式(A-1)表示之化合物及熱交聯性聚矽氧烷。
[化8]
R
1表示甲基、乙基、丙基、烯丙基、炔丙基,R
2表示氫原子、乙醯基、丙烯醯基、甲基丙烯醯基、苯甲醯基、萘甲醯基、蒽甲醯基,R
3表示甲基、乙基、丙基、烯丙基、炔丙基、或下列通式(A-2)表示之基。
[化9]
虛線表示原子鍵,R
1、R
2與前述相同。
[通式(A-1)表示之化合物]
上述通式(A-1)表示之化合物可例示下列等。R
3與前述相同。
上述通式(A-2)表示之結構可例示下列等。
上述通式(A-1)表示之化合物之較佳例可例示下列等,具體而言,R
1為烯丙基或炔丙基,R
2為氫原子、乙醯基、丙烯酸基,R
3為烯丙基或上述通式(A-2)表示之基較佳,R
1為烯丙基或炔丙基,R
2為氫原子、乙醯基,R
3為烯丙基尤佳。
[通式(A-1)表示之化合物之合成方法]
作為獲得本發明中使用之通式(A-1)表示之化合物的手段,並無特別限定,可利用如下列反應式表示之環氧化合物與異氰尿酸衍生物的加成反應(STEP1-1)獲得,R
2不為氫原子時,可後續利用醯化反應(STEP1-2)獲得。惟,R
3為(A-2)時,可藉由使用三官能之環氧化合物作為環氧化合物並進行同樣之反應(STEP2-1、STEP2-2)來獲得。下式中之R
1、R
2、R
3與前述相同。
上述STEP1-1、或STEP2-1表示之環氧化合物與異氰尿酸衍生物的反應,令環氧化合物中之環氧量之莫耳量為1莫耳時,異氰尿酸衍生物的進料量宜為0.3~2.0莫耳,更佳0.5~1.5莫耳,尤佳為0 .75~1.25莫耳。
異氰尿酸衍生物的進料量相對於環氧單元只要沒有不足,則不會有未反應的環氧基殘存,且不會影響保存穩定性。異氰尿酸衍生物的進料量相對於環氧單元只要不過剩,則不會有未反應的異氰尿酸衍生物殘存,且不會產生散逸氣體。
由如上述之原料合成的化合物,通常可藉由在溶劑中或溶劑中且反應觸媒存在下,於室溫或視需要冷卻或加熱下使環氧化合物與異氰尿酸衍生物反應而獲得。
所使用之溶劑可例示:甲醇、乙醇、異丙醇、丁醇、乙二醇、丙二醇、二乙二醇、甘油、甲基賽珞蘇、乙基賽珞蘇、丁基賽珞蘇、丙二醇單甲醚等醇類;二乙醚、二丁醚、二乙二醇二乙醚、二乙二醇二甲醚、四氫呋喃、1,4-二㗁烷等醚類;二氯甲烷、氯仿、二氯乙烷、三氯乙烯等氯系溶劑類;己烷、庚烷、苯、甲苯、二甲苯、異丙苯等烴類;乙腈等腈類;丙酮、甲乙酮、異丁基甲基酮等酮類;乙酸乙酯、乙酸正丁酯、丙二醇甲醚乙酸酯等酯類;γ-丁內酯等內酯類;二甲基亞碸、N,N-二甲基甲醯胺、六甲基磷醯三胺等非質子性極性溶劑類,該等可單獨使用或將2種以上混合使用。該等溶劑能以相對於反應原料100質量份為0~ 2000質量份之範圍使用。
反應觸媒可列舉:苄基三乙基氯化銨、苄基三乙基溴化銨、苄基三甲基氯化銨、四甲基氯化銨、四甲基溴化銨、四甲基碘化銨、四甲基氫氧化銨、四乙基溴化銨、四丁基氯化銨、四丁基溴化銨、四丁基碘化銨、四丁基硫酸氫銨、三辛基甲基氯化銨、三丁基苄基氯化銨、三甲基苄基氯化銨、三甲基苄基氫氧化銨、N-月桂基氯化吡啶、N-月桂基氯化4-甲吡啶、N-月桂基氯化甲吡啶、三甲基苯基溴化銨、N-苄基氯化甲吡啶等4級銨鹽類;四丁基氯化鏻、四丁基溴化鏻、四苯基氯化鏻等4級鏻鹽;參[2-(2-甲氧基乙氧基)乙基]胺、參(3,6-二氧雜庚基)胺、參(3,6-二氧雜辛基)胺等3級胺類。使用量相對於原料為0.001~100重量% ,宜為0.005~50重量%之範圍。
反應溫度宜為-50℃至溶劑之沸點左右,為室溫至150℃ 更佳。反應時間係從0.1~100小時適當選擇。
就反應方法而言,有如下方法:將環氧化合物、異氰尿酸衍生物、觸媒一次性地加入;使環氧化合物與異氰尿酸衍生物分散或溶解後,將觸媒一次性地添加或以溶劑稀釋並滴加;或使觸媒分散或溶解後,將環氧化合物與異氰尿酸衍生物一次性地添加或以溶劑稀釋並滴加。反應結束後,可不進行精製等而直接使用,亦可為了去除存在於系內之未反應的原料、觸媒等而以有機溶劑稀釋後,進行分液洗淨並回收。
此時所使用之有機溶劑,只要是可溶解反應產物且與水混合則會分離成2層者,則無特別限制,可列舉:己烷、庚烷、苯、甲苯、二甲苯等烴類;乙酸乙酯、乙酸正丁酯、丙二醇甲醚乙酸酯等酯類;甲乙酮、甲基戊基酮、環己酮、甲基異丁基酮等酮類;二乙醚、二異丙醚、甲基-第三丁醚、乙基環戊基甲醚等醚類;二氯甲烷、氯仿、二氯乙烷、三氯乙烯等氯系溶劑類;及它們的混合物等。此時使用的洗淨水,使用通常被稱為去離子水、超純水者即可。洗淨次數為1次以上即可,即使洗淨10次以上,也不一定會獲得相應的洗淨效果,故宜為約1~5次。
分液洗淨時為了去除未反應的異氰尿酸或酸性成分,亦可利用鹼性水溶液進行洗淨。鹼可列舉:鹼金屬之氫氧化物、鹼金屬之碳酸鹽、鹼土金屬之氫氧化物、鹼土金屬之碳酸鹽、氨、及有機銨等。
另外,為了去除分液洗淨時系內之金屬雜質或鹼成分,亦可利用酸性水溶液進行洗淨。酸可列舉:鹽酸、氫溴酸、硫酸、硝酸、磷酸、雜多酸等無機酸類;草酸、三氟乙酸、甲磺酸、苯磺酸、對甲苯磺酸、三氟甲磺酸等有機酸類等。
利用鹼性水溶液、酸性水溶液所為之分液水洗可僅進行其中一者,亦可組合進行,考量去除金屬雜質的觀點,分液水洗宜以鹼性水溶液、酸性水溶液的順序進行。
上述利用鹼性水溶液、酸性水溶液所為之分液水洗後,亦可接續利用中性水進行洗淨。洗淨次數只要進行1次以上即可,宜為約1~5次。中性水可使用上述去離子水、超純水等。洗淨次數為1次以上即可,但次數少的話,會有無法去除鹼成分、酸性成分的情況。即使洗淨10次以上,也不一定會獲得相應的洗淨效果,故宜為約1~5次。
另外,分液操作後之反應產物,亦可於減壓或常壓將溶劑進行濃縮乾固或晶析操作,而以粉體形式回收,為了改善製備含矽之阻劑下層膜形成用組成物時之操作性,也可預先製成適度濃度的溶液狀態。此時濃度只要不過濃,則黏度不會過高且不會損及操作性。只要不過稀,則溶劑的量不會過大而係經濟。此時的濃度宜為0.1~50質量%,更佳為0.5~30重量%。
此時的溶劑只要是可溶解獲得之化合物者,則無特別限制,舉具體例的話,可列舉:環己酮、甲基-2-戊基酮等酮類;3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇、1-乙氧基-2-丙醇等醇類;丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇二甲醚、二乙二醇二甲醚等醚類;丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、乳酸乙酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯等酯類,該等可單獨使用或將2種以上混合使用。
STEP1-2或STEP2-2表示之反應可利用習知的方法輕易地進行,醯化劑宜為與乙酸、丙烯酸、甲基丙烯酸、苯甲酸、1-萘甲酸、2-萘甲酸、2-蒽甲酸、9-蒽甲酸等對應的醯氯或酸酐較佳。使用醯氯時,可於無溶劑或二氯甲烷、乙腈、甲苯、己烷等溶劑中,依序或同時加入STEP1-1或STEP2-1中獲得之化合物與醯氯與三乙胺、吡啶、4-二甲基胺基吡啶等鹼,視需要進行冷卻或加熱等而實施。又,使用酸酐時,可於甲苯等溶劑中,依序或同時加入STEP1-1或STEP2-1中獲得之化合物與三乙胺、吡啶、4-二甲基胺基吡啶等鹼,視需要進行冷卻或加熱等而實施。獲得之反應產物可施以水洗等精製操作,並以粉體或溶液的形式回收。以溶液的形式回收時的溶劑,可例示就將STEP1-1、STEP2-1中獲得之化合物以溶液的形式回收時所使用的溶劑所列舉者,此時的濃度宜為0.1~50質量%,更佳為0.5~30重量%。
此外,本發明中使用之通式(A-1)表示之化合物可單獨使用1種或將2種以上組合使用。該等化合物的添加量,相對於基礎聚合物(利用後述方法獲得之熱交聯性聚矽氧烷)100質量份,宜為0.01~40質量份,更佳為0.1~30質量份,尤佳為1~20質量份。
藉由將如此之化合物使用於例如含矽之阻劑下層膜,對於形成於其上的光阻劑圖案展現良好的密接性,又,相對於形成於上部之阻劑圖案與形成於下部之例如有機膜之兩者展現高蝕刻選擇性,故將形成的光阻劑圖案利用乾蝕刻處理依序進行圖案轉印至含矽之阻劑下層膜、有機下層膜時,能以良好的圖案形狀進行圖案轉印。藉此,最終可將以上層阻劑形成之圖案以高精度轉印至基板。
[熱交聯性聚矽氧烷]
本發明之含矽之阻劑下層膜形成用組成物,含有上述通式(A-1)表示之化合物中之1種或2種以上,且含有熱交聯性聚矽氧烷(Sx)。
本發明中使用之熱交聯性聚矽氧烷(Sx),宜含有下列通式(Sx-1)表示之重複單元、下列通式(Sx-2)表示之重複單元、及下列通式(Sx-3)表示之次結構中之任一者以上。
[化23]
[化24]
[化25]
式中,R
4、R
5、R
6可各自相同亦可不同地為碳數1~30之1價有機基。
上述熱交聯性聚矽氧烷(Sx),可藉由將下列水解性單體(Sm)進行水解縮合而製造。
作為水解性單體(Sm),具體而言,可例示:四甲氧基矽烷、四乙氧基矽烷、四丙氧基矽烷、四異丙氧基矽烷、三甲氧基矽烷、三乙氧基矽烷、三丙氧基矽烷、三異丙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、甲基三丙氧基矽烷、甲基三異丙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙基三丙氧基矽烷、乙基三異丙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三丙氧基矽烷、乙烯基三異丙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、丙基三丙氧基矽烷、丙基三異丙氧基矽烷、異丙基三甲氧基矽烷、異丙基三乙氧基矽烷、異丙基三丙氧基矽烷、異丙基三異丙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、丁基三丙氧基矽烷、丁基三異丙氧基矽烷、第二丁基三甲氧基矽烷、第二丁基三乙氧基矽烷、第二丁基三丙氧基矽烷、第二丁基三異丙氧基矽烷、第三丁基三甲氧基矽烷、第三丁基三乙氧基矽烷、第三丁基三丙氧基矽烷、第三丁基三異丙氧基矽烷、環丙基三甲氧基矽烷、環丙基三乙氧基矽烷、環丙基三丙氧基矽烷、環丙基三異丙氧基矽烷、環丁基三甲氧基矽烷、環丁基三乙氧基矽烷、環丁基三丙氧基矽烷、環丁基三異丙氧基矽烷、環戊基三甲氧基矽烷、環戊基三乙氧基矽烷、環戊基三丙氧基矽烷、環戊基三異丙氧基矽烷、環己基三甲氧基矽烷、環己基三乙氧基矽烷、環己基三丙氧基矽烷、環己基三異丙氧基矽烷、環己烯基三甲氧基矽烷、環己烯基三乙氧基矽烷、環己烯基三丙氧基矽烷、環己烯基三異丙氧基矽烷、環己烯基乙基三甲氧基矽烷、環己烯基乙基三乙氧基矽烷、環己烯基乙基三丙氧基矽烷、環己烯基乙基三異丙氧基矽烷、環辛基三甲氧基矽烷、環辛基三乙氧基矽烷、環辛基三丙氧基矽烷、環辛基三異丙氧基矽烷、環戊二烯基丙基三甲氧基矽烷、環戊二烯基丙基三乙氧基矽烷、環戊二烯基丙基三丙氧基矽烷、環戊二烯基丙基三異丙氧基矽烷、雙環庚烯基三甲氧基矽烷、雙環庚烯基三乙氧基矽烷、雙環庚烯基三丙氧基矽烷、雙環庚烯基三異丙氧基矽烷、雙環庚基三甲氧基矽烷、雙環庚基三乙氧基矽烷、雙環庚基三丙氧基矽烷、雙環庚基三異丙氧基矽烷、金剛烷基三甲氧基矽烷、金剛烷基三乙氧基矽烷、金剛烷基三丙氧基矽烷、金剛烷基三異丙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、苯基三丙氧基矽烷、苯基三異丙氧基矽烷、苄基三甲氧基矽烷、苄基三乙氧基矽烷、苄基三丙氧基矽烷、苄基三異丙氧基矽烷、甲氧基苄基三甲氧基矽烷、甲氧基苄基三乙氧基矽烷、甲氧基苄基三丙氧基矽烷、甲氧基苄基三異丙氧基矽烷、甲苯基三甲氧基矽烷、甲苯基三乙氧基矽烷、甲苯基三丙氧基矽烷、甲苯基三異丙氧基矽烷、苯乙基三甲氧基矽烷、苯乙基三乙氧基矽烷、苯乙基三丙氧基矽烷、苯乙基三異丙氧基矽烷、萘基三甲氧基矽烷、萘基三乙氧基矽烷、萘基三丙氧基矽烷、萘基三異丙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、二甲基二丙氧基矽烷、二甲基二異丙氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、二乙基二丙氧基矽烷、二乙基二異丙氧基矽烷、二丙基二甲氧基矽烷、二丙基二乙氧基矽烷、二丙基二丙氧基矽烷、二丙基二異丙氧基矽烷、二異丙基二甲氧基矽烷、二異丙基二乙氧基矽烷、二異丙基二丙氧基矽烷、二異丙基二異丙氧基矽烷、二丁基二甲氧基矽烷、二丁基二乙氧基矽烷、二丁基二丙氧基矽烷、二丁基二異丙氧基矽烷、二第二丁基二甲氧基矽烷、二第二丁基二乙氧基矽烷、二第二丁基二丙氧基矽烷、二第二丁基二異丙氧基矽烷、二第三丁基二甲氧基矽烷、二第三丁基二乙氧基矽烷、二第三丁基二丙氧基矽烷、二第三丁基二異丙氧基矽烷、二環丙基二甲氧基矽烷、二環丙基二乙氧基矽烷、二環丙基二丙氧基矽烷、二環丙基二異丙氧基矽烷、二環丁基二甲氧基矽烷、二環丁基二乙氧基矽烷、二環丁基二丙氧基矽烷、二環丁基二異丙氧基矽烷、二環戊基二甲氧基矽烷、二環戊基二乙氧基矽烷、二環戊基二丙氧基矽烷、二環戊基二異丙氧基矽烷、二環己基二甲氧基矽烷、二環己基二乙氧基矽烷、二環己基二丙氧基矽烷、二環己基二異丙氧基矽烷、二環己烯基二甲氧基矽烷、二環己烯基二乙氧基矽烷、二環己烯基二丙氧基矽烷、二環己烯基二異丙氧基矽烷、二環己烯基乙基二甲氧基矽烷、二環己烯基乙基二乙氧基矽烷、二環己烯基乙基二丙氧基矽烷、二環己烯基乙基二異丙氧基矽烷、二環辛基二甲氧基矽烷、二環辛基二乙氧基矽烷、二環辛基二丙氧基矽烷、二環辛基二異丙氧基矽烷、二環戊二烯基丙基二甲氧基矽烷、二環戊二烯基丙基二乙氧基矽烷、二環戊二烯基丙基二丙氧基矽烷、二環戊二烯基丙基二異丙氧基矽烷、雙(雙環庚烯基)二甲氧基矽烷、雙(雙環庚烯基)二乙氧基矽烷、雙(雙環庚烯基)二丙氧基矽烷、雙(雙環庚烯基)二異丙氧基矽烷、雙(雙環庚基)二甲氧基矽烷、雙(雙環庚基)二乙氧基矽烷、雙(雙環庚基)二丙氧基矽烷、雙(雙環庚基)二異丙氧基矽烷、二金剛烷基二甲氧基矽烷、二金剛烷基二乙氧基矽烷、二金剛烷基二丙氧基矽烷、二金剛烷基二異丙氧基矽烷、二苯基二甲氧基矽烷、二苯基二乙氧基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、二苯基二丙氧基矽烷、二苯基二異丙氧基矽烷、三甲基甲氧基矽烷、三甲基乙氧基矽烷、二甲基乙基甲氧基矽烷、二甲基乙基乙氧基矽烷、二甲基苯基甲氧基矽烷、二甲基苯基乙氧基矽烷、二甲基苄基甲氧基矽烷、二甲基苄基乙氧基矽烷、二甲基苯乙基甲氧基矽烷、二甲基苯乙基乙氧基矽烷等。
上述化合物較佳可例示:四甲氧基矽烷、四乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、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、乙烯基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、異丙基三甲氧基矽烷、異丙基三乙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、異丁基三甲氧基矽烷、異丁基三乙氧基矽烷、烯丙基三甲氧基矽烷、烯丙基三乙氧基矽烷、環戊基三甲氧基矽烷、環戊基三乙氧基矽烷、環己基三甲氧基矽烷、環己基三乙氧基矽烷、環己烯基三甲氧基矽烷、環己烯基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、苄基三甲氧基矽烷、苄基三乙氧基矽烷、苯乙基三甲氧基矽烷、苯乙基三乙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、甲基乙基二甲氧基矽烷、甲基乙基二乙氧基矽烷、二丙基二甲氧基矽烷、二丁基二甲氧基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、三甲基甲氧基矽烷、二甲基乙基甲氧基矽烷、二甲基苯基甲氧基矽烷、二甲基苄基甲氧基矽烷、二甲基苯乙基甲氧基矽烷等。
作為水解性單體(Sm),與以上例示之化合物對應的上述R
4、R
5、R
6表示之有機基之另一例,可列舉具有1個以上之碳-氧單鍵或碳-氧雙鍵之有機基。具體而言,為具有選自由醚鍵、酯鍵、烷氧基、羥基等構成之群組中之1個以上之基的有機基。其示例可列舉下列通式(Sm-R)表示者。
(P-Q
1-(S
1)
v1-Q
2-)
u-(T)
v2-Q
3-(S
2)
v3-Q
4-
(Sm-R)
通式(Sm-R)中,P為氫原子、環狀醚基、羥基、碳數1~4之烷氧基、碳數1~6之烷基羰基氧基、或碳數1~6之烷基羰基,Q
1、Q
2、Q
3、及Q
4各自獨立地為-C
qH
(2q-p)P
p-(式中,P與上述同樣,p為0~3之整數,q為0~10之整數(惟,q=0表示為單鍵。)。),u為0~3之整數,S
1與S
2各自獨立地表示-O-、-CO-、-OCO-、-COO-或-OCOO-。v1、v2、及v3各自獨立地表示0或1。T為碳以外之2價原子、脂環、芳香環或雜環構成之2價基。就T而言,亦可含有氧原子等雜原子之脂環、芳香環或雜環之示例如下所示。T中與Q
2和與Q
3鍵結的位置並無特別限定,可考量立體性因素所致之反應性、反應所使用的市售試劑的取得性等而適當選擇。
通式(Sm-R)中之具有1個以上之碳-氧單鍵或碳-氧雙鍵之有機基的較佳例,可列舉如下。此外,下式中,(Si)係用以表示與Si之鍵結位置而記載。
又,作為R
4、R
5、R
6之有機基之示例,亦可使用具有會因酸分解之保護基的有機基。具體而言,可列舉日本特開2013-167669號公報之[0043]段落至[0048]段落所列舉之有機基、由日本特開2013-224279號公報之[0056]段落所示之矽化合物獲得之有機基。
另外,作為R
4、R
5、R
6之有機基之示例,也可使用具有氟原子的有機基。具體而言,可列舉由日本特開2012-53253號公報之[0059]段落至[0065]段落所示之矽化合物獲得的有機基。
就上述水解性單體(Sm)而言,於上述次結構中(Si)表示之矽上鍵結有1個、2個或3個氯、溴、碘、乙醯氧基、甲氧基、乙氧基、丙氧基或丁氧基等作為水解性基。
[熱交聯性聚矽氧烷(Sx)之合成方法]
(合成方法1:酸觸媒)
本發明中使用之熱交聯性聚矽氧烷(Sx),可藉由將1種水解性單體(Sm)或2種以上之混合物,在酸觸媒的存在下進行水解縮合而製造。
此時使用之酸觸媒可列舉:甲酸、乙酸、草酸、馬來酸、甲磺酸、苯磺酸、甲苯磺酸等有機酸;氫氟酸、鹽酸、氫溴酸、硫酸、硝酸、過氯酸、磷酸等無機酸。觸媒的使用量相對於單體1莫耳,為1×10
-6~10莫耳,宜為1×10
-5~5莫耳,更佳為1×10
-4~1莫耳。
由該等單體利用水解縮合獲得熱交聯性聚矽氧烷(Sx)時的水的量,就鍵結於單體之水解性取代基每1莫耳而言,宜添加0.01~100莫耳,更佳為0.05~50莫耳,又更佳為0.1~30莫耳。若為100莫耳以下,反應所使用之裝置變小,係經濟。
就操作方法而言,係在觸媒水溶液中添加單體並使水解縮合反應開始。此時,可在觸媒水溶液中添加有機溶劑,亦可將單體利用有機溶劑進行稀釋,也可實施兩種。反應溫度為0~100℃,宜為5~80℃。宜為於單體滴加時將溫度保持在5~80℃,之後在20~80℃使其熟成的方法較佳。
可添加至觸媒水溶液中的有機溶劑、或可稀釋單體的有機溶劑宜為:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、乙腈、四氫呋喃、甲苯、己烷、乙酸乙酯、甲乙酮、甲基異丁基酮、環己酮、甲基戊基酮、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯、γ-丁內酯及它們的混合物等。
該等溶劑中,宜為水溶性者。例如可列舉:甲醇、乙醇、1-丙醇、2-丙醇等醇類;乙二醇、丙二醇等多元醇;丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚等多元醇縮合物衍生物;丙酮、乙腈、四氫呋喃等。其中尤其宜為沸點為100℃以下者。
此外,有機溶劑的使用量相對於單體1莫耳,宜為0~1,000ml,尤其宜為0~500ml。有機溶劑的使用量少的話,反應容器變小,係經濟。
之後,視需要進行觸媒的中和反應,得到反應混合物水溶液。此時,可使用於中和的鹼性物質的量,相對於觸媒所使用的酸宜為0.1~2當量。該鹼性物質只要是在水中呈現鹼性者,則可為任意物質。
然後,宜利用減壓去除等從反應混合物去除水解縮合反應所生成的醇等副產物。此時將反應混合物進行加熱的溫度取決於所添加之有機溶劑與反應產生之醇等的種類,宜為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時的減壓度取決於欲去除的有機溶劑及醇等的種類、排氣裝置、冷凝濃縮裝置及加熱溫度而有所不同,宜為大氣壓以下,更佳為以絕對壓力計80kPa以下,又更佳為以絕對壓力計50kPa以下。雖難以正確得知此時去除的醇量,但去除約80質量%以上所生成的醇等較為理想。
然後,亦可從反應混合物將水解縮合所使用的酸觸媒去除。作為去除酸觸媒的方法,係將水與熱交聯性聚矽氧烷溶液混合,並利用有機溶劑萃取熱交聯性聚矽氧烷。此時所使用之有機溶劑,宜為可溶解熱交聯性聚矽氧烷,且與水混合則會分離成2層者。例如可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基戊基酮、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯、γ-丁內酯、甲基異丁基酮、環戊基甲醚及它們的混合物等。
另外,亦可使用水溶性有機溶劑與水難溶性有機溶劑之混合物。例如宜為:甲醇-乙酸乙酯混合物、乙醇-乙酸乙酯混合物、1-丙醇-乙酸乙酯混合物、2-丙醇-乙酸乙酯混合物、丁二醇單甲醚-乙酸乙酯混合物、丙二醇單甲醚-乙酸乙酯混合物、乙二醇單甲醚-乙酸乙酯混合物、丁二醇單乙醚-乙酸乙酯混合物、丙二醇單乙醚-乙酸乙酯混合物、乙二醇單乙醚-乙酸乙酯混合物、丁二醇單丙醚-乙酸乙酯混合物、丙二醇單丙醚-乙酸乙酯混合物、乙二醇單丙醚-乙酸乙酯混合物、甲醇-甲基異丁基酮混合物、乙醇-甲基異丁基酮混合物、1-丙醇-甲基異丁基酮混合物、2-丙醇-甲基異丁基酮混合物、丙二醇單甲醚-甲基異丁基酮混合物、乙二醇單甲醚-甲基異丁基酮混合物、丙二醇單乙醚-甲基異丁基酮混合物、乙二醇單乙醚-甲基異丁基酮混合物、丙二醇單丙醚-甲基異丁基酮混合物、乙二醇單丙醚-甲基異丁基酮混合物、甲醇-環戊基甲醚混合物、乙醇-環戊基甲醚混合物、1-丙醇-環戊基甲醚混合物、2-丙醇-環戊基甲醚混合物、丙二醇單甲醚-環戊基甲醚混合物、乙二醇單甲醚-環戊基甲醚混合物、丙二醇單乙醚-環戊基甲醚混合物、乙二醇單乙醚-環戊基甲醚混合物、丙二醇單丙醚-環戊基甲醚混合物、乙二醇單丙醚-環戊基甲醚混合物、甲醇-丙二醇甲醚乙酸酯混合物、乙醇-丙二醇甲醚乙酸酯混合物、1-丙醇-丙二醇甲醚乙酸酯混合物、2-丙醇-丙二醇甲醚乙酸酯混合物、丙二醇單甲醚-丙二醇甲醚乙酸酯混合物、乙二醇單甲醚-丙二醇甲醚乙酸酯混合物、丙二醇單乙醚-丙二醇甲醚乙酸酯混合物、乙二醇單乙醚-丙二醇甲醚乙酸酯混合物、丙二醇單丙醚-丙二醇甲醚乙酸酯混合物、乙二醇單丙醚-丙二醇甲醚乙酸酯混合物等,但組合不限於該等。
此外,水溶性有機溶劑與水難溶性有機溶劑之混合比例可適當選擇,相對於水難溶性有機溶劑100質量份,水溶性有機溶劑為0.1~1,000質量份,宜為1~500質量份,又更佳為2~100質量份。
然後,亦可利用中性水進行洗淨。該水使用通常被稱為去離子水、超純水的水即可。該水的量相對於熱交聯性聚矽氧烷溶液1L,宜為0.01~100L,更佳為0.05~50L,又更佳為0.1~5L。就該洗淨方法而言,將兩種溶液放入相同容器並攪拌,然後靜置將水層分離即可。洗淨次數為1次以上即可,即使洗淨10次以上,也不一定會獲得相應的洗淨效果,故宜為約1~5次。
作為其他將酸觸媒去除的方法,可列舉利用離子交換樹脂的方法、以環氧乙烷、環氧丙烷等環氧化合物中和後予以去除的方法。該等方法可配合反應所使用之酸觸媒而適當選擇。
利用此時的水洗操作,熱交聯性聚矽氧烷的一部分會逃往水層,有時會獲得實質上與分級操作同等的效果,故水洗次數、洗淨水的量視觸媒去除效果與分級效果而適當選擇即可。
殘留有酸觸媒的熱交聯性聚矽氧烷溶液及去除了酸觸媒的熱交聯性聚矽氧烷溶液,均可藉由添加最終的溶劑並於減壓下進行溶劑交換,來獲得期望之熱交聯性聚矽氧烷溶液。此時溶劑交換的溫度取決於欲去除的反應溶劑、萃取溶劑的種類,宜為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時的減壓度取決於欲去除的萃取溶劑的種類、排氣裝置、冷凝濃縮裝置及加熱溫度而有所不同,宜為大氣壓以下,更佳為以絕對壓力計80kPa以下,又更佳為以絕對壓力計50kPa以下。
此時,會有因溶劑變化而導致熱交聯性聚矽氧烷變得不穩定的情況。其係取決於最終的溶劑與熱交聯性聚矽氧烷的相容性(compatibility)而會發生,為了防止此情況,亦可加入日本特開2009-126940號公報[0181]~[0182]段落記載之具有環狀醚作為取代基的1元或2元以上的醇作為穩定劑。添加量相對於溶劑交換前之溶液中之熱交聯性聚矽氧烷100質量份,為0~25質量份,宜為0~15質量份,更佳為0~5質量份,但有添加時宜為0.5質量份以上。溶劑交換前之溶液中若有必要,也可添加具有環狀醚作為取代基之1元或2元以上之醇後再實施溶劑交換操作。
熱交聯性聚矽氧烷濃縮到一定濃度以上的話,會有縮合反應進一步進行,變化成無法再溶解於有機溶劑的狀態之虞,故宜預先製成適當濃度的溶液狀態。又,過稀的話,溶劑的量變得過多,故預先製成適當濃度的溶液狀態係經濟且較佳。此時的濃度宜為0.1~20質量%。
添加至熱交聯性聚矽氧烷溶液中的最終的溶劑宜為醇系溶劑,尤其宜為乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇、丁二醇等之單烷醚衍生物。具體而言,宜為丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚、二丙酮醇等。
該等溶劑若為主成分,則也可添加非醇系溶劑作為輔助溶劑。該輔助溶劑可例示:丙酮、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基戊基酮、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯、γ-丁內酯、甲基異丁基酮、環戊基甲醚等。
又,作為使用了酸觸媒的另一反應操作,係於單體或單體之有機溶液中添加水或含水有機溶劑,使水解反應開始。此時觸媒可添加在單體或單體之有機溶液中,也可添加在水或含水有機溶劑中。反應溫度為0~100℃,宜為10~80℃。宜為於水滴加時加熱至10~50℃,之後升溫至20~80℃使其熟成的方法較佳。
使用有機溶劑時,宜為水溶性者,可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、四氫呋喃、乙腈、丁二醇單甲醚、丙二醇單甲醚、乙二醇單甲醚、丁二醇單乙醚、丙二醇單乙醚、乙二醇單乙醚、丁二醇單丙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚等多元醇縮合物衍生物及它們的混合物等。
有機溶劑的使用量相對於單體1莫耳,宜為0~1,000ml,尤其宜為0~500ml。有機溶劑的使用量少則反應容器變小,係經濟。獲得之反應混合物的後處理可和前述方法同樣地進行後處理,並獲得熱交聯性聚矽氧烷。
(合成方法2:鹼觸媒)
又,熱交聯性聚矽氧烷(Sx),可藉由將1種水解性單體(Sm)或2種以上之混合物,在鹼觸媒的存在下進行水解縮合而製造。
此時使用之鹼觸媒可列舉:甲胺、乙胺、丙胺、丁胺、乙二胺、六亞甲基二胺、二甲胺、二乙胺、乙基甲胺、三甲胺、三乙胺、三丙胺、三丁胺、環己胺、二環己胺、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、二氮雜雙環環壬烯、二氮雜雙環十一烯、六亞甲基四胺、苯胺、N,N-二甲基苯胺、吡啶、N,N-二甲基胺基吡啶、吡咯、哌𠯤、吡咯啶、哌啶、甲基吡啶、四甲基氫氧化銨、氫氧化膽鹼、四丙基氫氧化銨、四丁基氫氧化銨、氨、氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化鋇、氫氧化鈣等。觸媒的使用量相對於矽單體1莫耳,為1×10
-6莫耳~10莫耳,宜為1×10
-5莫耳~5莫耳,更佳為1×10
-4莫耳~1莫耳。
由上述單體利用水解縮合獲得熱交聯性聚矽氧烷時的水的量,就鍵結於單體之水解性取代基每1莫耳而言,宜添加0.1~50莫耳。為50莫耳以下的話,反應所使用的裝置變小,係經濟。
就操作方法而言,係在觸媒水溶液中添加單體並使水解縮合反應開始。此時,可在觸媒水溶液中添加有機溶劑,亦可將單體利用有機溶劑進行稀釋,也可實施兩種。反應溫度為0~100℃,宜為5~80℃。宜為於單體滴加時將溫度保持在5~80℃,之後在20~80℃使其熟成的方法較佳。
可添加至鹼觸媒水溶液中的有機溶劑、或可稀釋單體的有機溶劑,宜使用與就可添加至酸觸媒水溶液中者所例示的有機溶劑同樣者。此外,為了經濟地實施反應,有機溶劑的使用量相對於單體1莫耳宜為0~1,000ml。
之後,視需要進行觸媒的中和反應,得到反應混合物水溶液。此時,可使用於中和的酸性物質的量,相對於觸媒所使用的鹼性物質宜為0.1~2當量。該酸性物質只要是在水中呈現酸性者,則可為任意物質。
然後,宜利用減壓去除等從反應混合物去除水解縮合反應所生成的醇等副產物。此時將反應混合物進行加熱的溫度取決於所添加之有機溶劑與反應產生之醇等的種類,宜為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時的減壓度取決於欲去除的有機溶劑及醇的種類、排氣裝置、冷凝濃縮裝置及加熱溫度而有所不同,宜為大氣壓以下,更佳為以絕對壓力計80kPa以下,又更佳為以絕對壓力計50kPa以下。雖難以正確得知此時去除的醇量,但去除約80質量%以上所生成的醇較為理想。
然後,為了去除水解縮合所使用之鹼觸媒,利用有機溶劑萃取熱交聯性聚矽氧烷。此時所使用之有機溶劑,宜為可溶解熱交聯性聚矽氧烷,且與水混合則會分離成2層者。例如可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、四氫呋喃、甲苯、己烷、乙酸乙酯、環己酮、甲基戊基酮、丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸第三丁酯、丙酸第三丁酯、丙二醇單第三丁醚乙酸酯、γ-丁內酯、甲基異丁基酮、環戊基甲醚、及它們的混合物等。
另外,亦可使用水溶性有機溶劑與水難溶性有機溶劑之混合物。
去除鹼觸媒時使用的有機溶劑之具體例,可使用與就去除酸觸媒時所使用者具體例示的上述有機溶劑、水溶性有機溶劑與水難性有機溶劑之混合物同樣者。
此外,水溶性有機溶劑與水難溶性有機溶劑之混合比例可適當選擇,相對於難溶性有機溶劑100質量份,水溶性有機溶劑為0.1~1,000質量份,宜為1~500質量份,又更佳為2~100質量份。
然後,利用中性水洗淨。該水使用通常被稱為去離子水、超純水的水即可。該水的量相對於熱交聯性聚矽氧烷溶液1L,為0.01~100L,宜為0.05~50L,更佳為0.1~5L。就該洗淨方法而言,將兩種溶液放入相同容器並攪拌,然後靜置將水層分離即可。洗淨次數為1次以上即可,即使洗淨10次以上,也不一定會獲得相應的洗淨效果,故宜為約1~5次。
藉由在洗淨完畢的熱交聯性聚矽氧烷溶液中,添加最終的溶劑,於減壓下進行溶劑交換,而獲得期望之熱交聯性聚矽氧烷溶液。此時溶劑交換的溫度取決於欲去除的萃取溶劑的種類,宜為0~100℃,更佳為10~90℃,又更佳為15~80℃。又,此時的減壓度取決於欲去除的萃取溶劑的種類、排氣裝置、冷凝濃縮裝置及加熱溫度而有所不同,宜為大氣壓以下,更佳為以絕對壓力計80kPa以下,又更佳為以絕對壓力計50kPa以下。
添加至熱交聯性聚矽氧烷溶液中的最終的溶劑宜為醇系溶劑,尤其宜為乙二醇、二乙二醇、三乙二醇等之單烷醚、丙二醇、二丙二醇等之單烷醚。具體而言,宜為丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇單丙醚、乙二醇單丙醚、二丙酮醇等。
又,作為使用了鹼觸媒之另一反應操作,係於單體或單體之有機溶液中添加水或含水有機溶劑,使水解反應開始。此時觸媒可添加在單體或單體之有機溶液中,也可添加在水或含水有機溶劑中。反應溫度為0~100℃,宜為10~80℃。宜為於水滴加時加熱至10~50℃,之後升溫至20~80℃使其熟成的方法較佳。
可作為單體之有機溶液或含水有機溶劑使用的有機溶劑,宜為水溶性者,可列舉:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、丙酮、四氫呋喃、乙腈、丙二醇單甲醚、乙二醇單甲醚、丙二醇單乙醚、乙二醇單乙醚、丙二醇單丙醚、乙二醇單丙醚、丙二醇二甲醚、二乙二醇二甲醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚等多元醇縮合物衍生物及它們的混合物等。
利用上述合成方法1或2獲得之熱交聯性聚矽氧烷的分子量,不僅可藉由單體的選擇來調整,還可藉由控制聚合時的反應條件來調整,宜使用重量平均分子量為100,000以下,更佳為200~50,000,又更佳為300~30,000者。重量平均分子量為100,000以下的話,不會有產生異物、發生塗布不均的情況。此外,關於上述重量平均分子量的數據,係利用使用RI作為檢測器,並使用四氫呋喃作為溶離溶劑的凝膠滲透層析法(GPC),並使用聚苯乙烯作為標準物質,以聚苯乙烯換算來表示分子量。
本發明中使用之熱交聯性聚矽氧烷的物性,取決於水解縮合時使用之酸或鹼觸媒的種類、反應條件而有所不同。因此,可配合作為目的之阻劑下層膜之性能而適當選擇。
另外,可使用將1種或2種以上之水解性單體(Sm)與下列通式(Mm)表示之水解性金屬化合物之混合物以利用了前述酸或鹼觸媒之條件製得的聚矽氧烷衍生物作為阻劑下層膜形成用組成物的成分。
[化30]
式中,R
7、R
8為碳數1~30之有機基,m7+m8為依U的種類而決定的和價數相同的數,m7、m8為0以上之整數,U為週期表的III族、IV族、或V族的元素,且排除碳及矽。
作為上述通式(Mm)表示之水解性金屬化合物,可例示硼、鋁、鎵、釔、鍺、鈦、鉿等的金屬醇鹽,具體而言可使用日本特開2020-118960號公報之[0107]~[0123]記載者。
(酸產生劑)
本發明之含矽之阻劑下層膜形成用組成物中,可更摻合1種或2種以上之酸產生劑。酸產生劑只要是熱酸產生劑、光酸產生劑、酸增殖劑等作為酸前驅體發揮作用之物質,則皆可使用,本發明中摻合之酸產生劑為係鋶鹽且會因高能量射線之作用而產生酸的光酸產生劑更佳。具體而言,可添加日本特開2007-199653號公報中之[0061]~[0085]段落記載之材料,但不限定於該等。
上述酸產生劑可單獨使用1種或將2種以上組合使用。添加酸產生劑時的添加量,相對於熱交聯性聚矽氧烷100份宜為0.05~50份,更佳為0.1~10份。
[其他成分]
(交聯觸媒)
本發明中,亦可將交聯觸媒(Xc)摻合至含矽之阻劑下層膜形成用組成物中。能摻合的交聯觸媒,可列舉下列通式(Xc0)表示之化合物。
L
aH
bA (Xc0)
式中,L為鋰、鈉、鉀、銣、銫、鋶、錪、鏻或銨。A為非親核性相對離子。a為1以上之整數,b為0或1以上之整數,且a+b為非親核性相對離子的價數。
就作為具體的(Xc0)的本發明中使用之交聯觸媒而言,可列舉下列通式(Xc-1)之鋶鹽、下列通式(Xc-2)之錪鹽、下列通式(Xc-3)之鏻鹽、下列通式(Xc-4)之銨鹽、鹼金屬鹽等、具有銨鹽、鋶鹽、鏻鹽、錪鹽作為結構之一部分的聚矽氧烷(Xc-10),具體而言,可添加日本特開2020-118960號公報中之[0124]~[0163]段落記載之材料等。
[化31]
[化32]
式中,R
204、R
205、R
206、R
207各自表示碳數1~12之直鏈狀、分支狀或環狀之烷基、烯基、側氧基烷基或側氧基烯基、碳數6~20之取代或非取代之芳基、或碳數7~12之芳烷基或芳基側氧基烷基,該等基之氫原子之一部分或全部亦可被烷氧基取代等。又,R
205與R
206亦可形成環,形成環時,R
205、R
206各自表示碳數1~6之伸烷基。A
-表示非親核性相對離子。R
208、R
209、R
210、R
211,係與R
204、R
205、R
206、R
207同樣,但亦可為氫原子。R
208與R
209、R
208與R
209與R
210亦可形成環,形成環時,R
208與R
209及R
208與R
209與R
210表示碳數3~10之伸烷基。
上述交聯觸媒(Xc-1)、(Xc-2)、(Xc-3)、(Xc-4)、(Xc-10)可單獨使用1種或將2種以上組合使用。交聯觸媒的添加量,相對於基礎聚合物(例如,利用上述方法獲得之熱交聯性聚矽氧烷(Sx))100質量份,宜為0.01~50質量份,更佳為0.1~40質量份。
本發明之含矽之阻劑下層膜形成用組成物中,亦可更摻合下列原料。
(有機酸)
為了改善本發明之含矽之阻劑下層膜形成用組成物的穩定性,宜添加碳數為1~30之1元或2元以上之有機酸。此時添加的酸可例示:甲酸、乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、油酸、硬脂酸、亞麻油酸、次亞麻油酸、苯甲酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、水楊酸、三氟乙酸、單氯乙酸、二氯乙酸、三氯乙酸、草酸、丙二酸、甲基丙二酸、乙基丙二酸、丙基丙二酸、丁基丙二酸、二甲基丙二酸、二乙基丙二酸、琥珀酸、甲基琥珀酸、戊二酸、己二酸、伊康酸、馬來酸、富馬酸、檸康酸、檸檬酸等。尤其宜為草酸、馬來酸、甲酸、乙酸、丙酸、檸檬酸等。又,為了保持穩定性,亦可將2種以上之酸混合使用。
有機酸的添加量,相對於本發明之含矽之阻劑下層膜形成用組成物中含有的熱交聯性聚矽氧烷100質量份為0.001~25質量份,宜為0.01~15質量份,更佳為0.1~5質量份。
或也可摻合上述有機酸以使換算成本發明之含矽之阻劑下層膜形成用組成物之pH較佳成為0≦pH≦7,更佳成為0.3≦pH≦6.5,又更佳成為0.5≦pH≦6。
(水)
本發明中,亦可於組成物中添加水。添加水的話,本發明之含矽之阻劑下層膜形成用組成物中之聚矽氧烷化合物進行水合,故微影性能改善。本發明之含矽之阻劑下層膜形成用組成物之溶劑成分中之水的含有率為超過0質量%且未達50質量%,尤其宜為0.3~30質量%,又更佳為0.5~20質量%。水的添加量為上述範圍內的話,含矽之阻劑下層膜之均勻性良好,不會有產生眼孔(eye hole),或微影性能降低之虞。
包含水之全部溶劑的使用量,相對於係基礎聚合物之熱交聯性聚矽氧烷(Sx)100質量份,宜為100~100,000質量份,尤其宜為200~50,000質量份。
(穩定劑)
另外,本發明中,可於組成物中添加穩定劑。穩定劑可添加具有環狀醚作為取代基之1元或2元以上之醇。尤其添加日本特開2009-126940號公報[0181]~[0182]段落記載之穩定劑的話,可改善含矽之阻劑下層膜形成用組成物的穩定性。
(界面活性劑)
另外,本發明中,可視需要於組成物中摻合界面活性劑。如此之界面活性劑,具體而言,可添加日本特開2009-126940號公報[0185]段落記載之材料。
(高沸點溶劑)
另外,本發明中,亦可視需要於組成物中添加沸點為180度以上之高沸點溶劑。該高沸點溶劑可例示:1-辛醇、2-乙基己醇、1-壬醇、1-癸醇、1-十一醇、乙二醇、1,2-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、甘油、γ-丁內酯、三丙二醇單甲醚、二丙酮醇、乙酸正壬酯、乙酸乙二醇單乙醚、1,2-二乙醯氧基乙烷、1-乙醯氧基-2-甲氧基乙烷、1,2-二乙醯氧基丙烷、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-正丁醚、乙酸丙二醇單甲醚、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等。
[圖案形成方法]
(圖案形成方法1)
本發明之圖案形成方法之一係包含下列步驟之圖案形成方法(所謂「多層阻劑法」):於被加工體上使用塗布型有機膜材料來形成有機膜;於前述有機膜上使用本發明之含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜;於上述含矽之阻劑下層膜上使用由光阻劑組成物構成之阻劑上層膜用組成物來形成阻劑上層膜;於上述阻劑上層膜形成電路圖案;將形成有上述電路圖案之上述阻劑上層膜作為遮罩,利用蝕刻將圖案轉印至上述含矽之阻劑下層膜;將轉印有上述圖案之上述含矽之阻劑下層膜作為遮罩,利用蝕刻對上述有機膜進行圖案轉印;及將轉印有上述圖案之上述有機膜作為遮罩,利用蝕刻將圖案轉印至上述被加工體。
(圖案形成方法2)
又,本發明之圖案形成方法係包含下列步驟之圖案形成方法(所謂「多層阻劑法」):於被加工體上利用CVD法形成以碳作為主成分之有機硬遮罩;於前述硬遮罩上使用本發明之含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜;於上述含矽之阻劑下層膜上使用由光阻劑組成物構成之阻劑上層膜用組成物來形成阻劑上層膜;於上述阻劑上層膜形成電路圖案;將形成有上述電路圖案之上述阻劑上層膜作為遮罩,利用蝕刻將圖案轉印至上述含矽之阻劑下層膜;將轉印有上述圖案之上述含矽之阻劑下層膜作為遮罩,利用蝕刻對上述硬遮罩進行圖案轉印;及將轉印有上述圖案之上述硬遮罩作為遮罩,利用蝕刻將圖案轉印至上述被加工體。
於被加工體上(含矽之阻劑下層膜之下)形成塗布型有機膜時,塗布型有機膜材料宜使用含有含芳香環之化合物者。使用如此之材料作為塗布型有機膜材料的話,可進一步抑制圖案崩塌的發生。
另一方面,於被加工體上(含矽之阻劑下層膜之下)形成CVD硬遮罩時,可利用CVD法形成以碳作為主成分之硬遮罩,也可利用習知的方法進行。
使用本發明之含矽之阻劑下層膜形成用組成物形成阻劑圖案的話,如上述,藉由使硬遮罩、有機膜之組合最適化,可抑制圖案崩塌且以良好的形狀在基板上形成以光阻劑形成之超微細圖案。又,圖案形成後所殘存的含矽之阻劑下層膜容易利用蝕刻等去除,故可抑制成為缺陷之原因的殘渣,又,亦可防止因過剩的蝕刻條件所致之基板損傷。
形成含矽之阻劑下層膜時,可藉由利用旋塗法等將本發明之含矽之阻劑下層膜形成用組成物塗布於被加工體上來進行。旋塗後,為了使溶劑蒸發,防止與由光阻劑組成物構成之阻劑上層膜、由塗布型有機膜材料構成之有機膜的混合,並為了促進交聯反應,而進行烘烤(熱處理)。烘烤宜於50℃以上500℃以下、10~600秒之範圍內進行,更佳為於100℃以上400℃以下、10~300秒之範圍內進行。
又,含矽之阻劑下層膜之形成,亦可藉由利用上述同樣之旋塗法等將本發明之含矽之阻劑下層膜形成用組成物塗覆在被加工基板上,於氧濃度0.1%以上21%以下之環境中進行煅燒並使其硬化,而形成含矽之阻劑下層膜。
藉由將本發明之含矽之阻劑下層膜在如此之氧環境中進行煅燒,可獲得充分硬化的膜。烘烤中之環境可為空氣中,但為了使氧減少,預先封入N
2、Ar、He等鈍性氣體,可防止係有機膜之阻劑下層膜氧化。為了防止氧化,須控制氧濃度,宜為1000ppm以下,更佳為100ppm以下。
使用本發明之組成物所形成的含矽之阻劑下層膜之厚度可適當選擇,宜為1~300nm,更佳為1~200nm,尤佳為1~100nm。
本發明之圖案形成方法中,阻劑上層膜用組成物只要是由化學增幅型光阻劑組成物構成者,則無特別限定。此外,本發明中,使用了鹼顯影液之正顯影、使用了有機溶劑之顯影液之負顯影均可採用,故配合顯影方法適當選擇正型阻劑上層膜材料、負型阻劑上層膜材料即可。
此外,正型圖案形成方法中,在阻劑上層膜形成、加熱處理後,進行曝光,通常使用鹼顯影液來進行鹼顯影,獲得正型阻劑圖案。又,曝光後宜進行曝光後烘烤(PEB)。
該鹼顯影液可使用四甲基氫氧化銨(TMAH)水溶液等。
又,負型圖案形成方法中,在阻劑上層膜形成、加熱處理後,進行曝光,通常使用有機溶劑來進行有機溶劑顯影,獲得負型阻劑圖案。又,曝光後宜進行PEB。
該有機溶劑之顯影液,可使用含有選自4-甲基-2-戊醇、2-辛酮、2-壬酮、2-庚酮、3-庚酮、4-庚酮、2-己酮、3-己酮、二異丁基酮、甲基環己酮、苯乙酮、甲基苯乙酮、乙酸丙酯、乙酸丁酯、乙酸異丁酯、乙酸戊酯、乙酸丁烯酯、乙酸異戊酯、乙酸苯酯、甲酸丙酯、甲酸丁酯、甲酸異丁酯、甲酸戊酯、甲酸異戊酯、戊酸甲酯、戊烯酸甲酯、巴豆酸甲酯、巴豆酸乙酯、乳酸甲酯、乳酸乙酯、乳酸丙酯、乳酸丁酯、乳酸異丁酯、乳酸戊酯、乳酸異戊酯、2-羥基異丁酸甲酯、2-羥基異丁酸乙酯、苯甲酸甲酯、苯甲酸乙酯、乙酸苯酯、乙酸苄酯、苯基乙酸甲酯、甲酸苄酯、甲酸苯基乙酯、3-苯基丙酸甲酯、丙酸苄酯、苯基乙酸乙酯、乙酸-2-苯基乙酯中之1種以上作為成分的顯影液等。
本發明之圖案形成方法,阻劑上層膜之圖案崩塌受到抑制,且可形成良好的圖案形狀。又,利用乾蝕刻所為之朝含矽之阻劑下層膜之圖案轉印優異,且圖案化結束後所殘存的含矽之阻劑下層膜之去除容易,不易產生因殘渣所致之缺陷,故尤其於微細圖案之形成係實用的圖案形成方法。
於上述阻劑上層膜形成電路圖案的步驟中之圖案形成,宜利用波長為10nm以上300nm以下之光微影、電子束所為之直接描繪、奈米壓印或它們的組合來形成圖案較佳。
上述被加工體宜為半導體裝置基板、金屬膜、金屬碳化膜、金屬氧化膜、金屬氮化膜、金屬氧化碳化膜或金屬氧化氮化膜。
上述被加工體為如此者時,會更充分地發揮本發明之效果。
構成上述被加工體之金屬,宜為矽、鎵、鈦、鎢、鉿、鋯、鉻、鍺、銅、銀、金、銦、砷、鈀、鉭、銥、鋁、鐵、鉬、鈷或它們的合金。
構成上述被加工體之金屬為上述特定金屬時,會更充分地發揮本發明之效果。
[實施例]
以下,舉合成例及實施例與比較例具體地說明本發明,但本發明不受該等記載限定。此外,下列示例中%表示質量%,分子量Mw係利用GPC測定獲得之聚苯乙烯換算之重量平均分子量。
(合成例1)
化合物(A1)之合成
[化34]
於氮氣環境下,在安裝有溫度計、回流管之三口燒瓶中,加入(B1)20.0g、(B4)32.8g、BHT(二丁基羥基甲苯)0.05g、PGME(1-甲氧基丙醇)150g。升溫至內溫80℃並製成均勻溶液後,加入苄基三乙基氯化銨1.00g,於110℃反應7小時。反應停止後,以MIBK(甲基異丁基酮)400ml稀釋後,移至分液漏斗,依序以1%氨水溶液100g洗淨2次,以3%硝酸水溶液100g洗淨2次,以超純水100ml洗淨5次。回收有機相並進行濃縮乾固,藉此得到化合物(A1)51.0g。
(合成例2)
化合物(A2)之合成
[化35]
於氮氣環境下,在安裝有溫度計、回流管之三口燒瓶中,加入(B2)20.0g、(B4)29.8g、BHT0.05g、PGME150g。升溫至內溫80℃並製成均勻溶液後,加入苄基三乙基氯化銨1.00g(0.4mmol),於110℃反應7小時。反應停止後,以MIBK400ml稀釋後,移至分液漏斗,依序以1%氨水溶液100g洗淨2次,以3%硝酸水溶液100g洗淨2次,以超純水100ml洗淨5次。回收有機相並進行濃縮乾固,藉此得到化合物(A2)48.3g。
(合成例3)
化合物(A3)之合成
[化36]
於氮氣環境下,在安裝有溫度計、回流管之三口燒瓶中,加入(B2)20.0g、(B5)29.2g、PGME150g。升溫至內溫80℃並製成均勻溶液後,加入苄基三乙基氯化銨1.0g,於110℃反應7小時。反應停止後,以MIBK400ml稀釋後,移至分液漏斗,依序以1%氨水溶液100g洗淨2次,以3%硝酸水溶液100g洗淨2次,以超純水100ml洗淨5次。回收有機相並進行濃縮乾固,藉此得到化合物(A3)46.7g。
(合成例4)
化合物(A4)之合成
[化37]
於氮氣環境下,在安裝有溫度計、回流管之三口燒瓶中,加入(B3)20.0g、(B4)42.2g、BHT0.05g、PGME200g。升溫至內溫80℃並製成均勻溶液後,加入苄基三乙基氯化銨1.0g,於110℃反應7小時。反應停止後,以MIBK500ml稀釋後,移至分液漏斗,依序以1%氨水溶液125g洗淨2次,以3%硝酸水溶液125g洗淨2次,以超純水125ml洗淨5次。回收有機相並進行濃縮乾固,藉此得到化合物(A4)59.7g。
(合成例5)
化合物(A5)之合成
[化38]
於氮氣環境下,在安裝有溫度計、回流管之三口燒瓶中,加入(B3)20.0g、(B5)41.4g、PGME200g。升溫至內溫80℃並製成均勻溶液後,加入苄基三乙基氯化銨1.0g,於110℃反應7小時。反應停止後,以MIBK500ml稀釋後,移至分液漏斗,依序以1%氨水溶液125g洗淨2次,以3%硝酸水溶液125g洗淨2次,以超純水125ml洗淨5次。回收有機相並進行濃縮乾固,藉此得到化合物(A5)60.2g。
(合成例6)
化合物(A6)之合成
[化39]
加入化合物(A2)20.0g、吡啶11.3g、N-甲基吡咯烷酮80g,於氮氣環境下、室溫製成均勻溶液,緩慢滴加乙酸酐11.7g後,於40℃反應3小時。反應結束後,加入MIBK200ml後,邊於冰浴中冷卻邊緩慢加入超純水100g,使反應淬滅。淬滅後,移至分液漏斗並去除水層,將有機層以2%NaHCO
3水溶液100g洗淨2次,以3%硝酸水溶液60g洗淨2次,以純水60g洗淨6次後,將有機層進行減壓乾固。於殘渣中加入THF60g,製成均勻溶液後,以己烷200g進行晶析。將沉降的結晶利用過濾分取,以己烷200g洗淨2次並回收。將回收的結晶於40℃進行真空乾燥,藉此得到(A6)18.5g。
(合成例7)
化合物(A7)之合成
[化40]
加入化合物(A5)20.0g、三乙胺11.1g、ANTAGE W-400 0.05g、N-甲基吡咯烷酮80g,於氮氣環境下、冰浴中製成均勻溶液,緩慢滴加丙烯醯氯7.9g後,於室溫反應3小時。反應結束後,加入MIBK200ml後,邊在冰浴中冷卻邊緩慢加入5%鹽酸水溶液100g,使反應淬滅。淬滅後,移至分液漏斗並去除水層,將有機層以3%硝酸水溶液60g、純水60g洗淨6次後,將有機層進行減壓乾固。於殘渣中加入THF60g製成均勻溶液後,以己烷300g進行晶析。將沉降的結晶利用過濾分取,以己烷200g洗淨2次並回收。將回收的結晶於40℃進行真空乾燥,藉此得到(A7)20.5g。
[合成例]熱交聯性聚矽氧烷(C1)~(C3)之合成
(合成例8)
聚矽氧烷(C1)之合成
[化41]
加入甲醇120g、10%硝酸0.1g及超純水60g,於氮氣環境下、40℃製成均勻溶液後,緩慢滴加四甲氧基矽烷49.4g、甲基三甲氧基矽烷20.4g及苯基三甲氧基矽烷5.0g之混合物。滴加後,於40℃進行12小時的水解縮合反應。反應結束後,加入PGEE(丙二醇乙醚)600g,將水分及副產物醇餾去,以聚矽氧烷化合物(C1)之PGEE溶液400g(化合物濃度10%)的形式回收。測定聚矽氧烷化合物(C1)之聚苯乙烯換算分子量,結果Mw=2600。
(合成例9)
聚矽氧烷(C2)之合成
[化42]
加入甲醇120g、10%硝酸0.1g及超純水60g,於氮氣環境下、40℃製成均勻溶液後,緩慢滴加四甲氧基矽烷38.1g、甲基三甲氧基矽烷30.6g及3-環氧丙氧基丙基三甲氧基矽烷5.9g之混合物。滴加後,於40℃進行12小時的水解縮合反應。反應結束後,加入PGEE(丙二醇乙醚)600g,將水分及副產物醇餾去,以聚矽氧烷化合物(C2)之PGEE溶液440g(化合物濃度10%)的形式回收。測定聚矽氧烷化合物(C2)之聚苯乙烯換算分子量,結果Mw=2900。
(合成例10)
聚矽氧烷(C3)之合成
[化43]
加入乙醇1400g、超純水700g及25%四甲基氫氧化銨50g,於氮氣環境下、40℃製成均勻溶液。緩慢滴加2-(3,4-環氧環己基)乙基三甲氧基矽烷138.6g與苯基三甲氧基矽烷37.2g之混合物後,於40℃反應2小時。反應結束後,加入乙酸35g使反應停止,並於減壓將乙醇餾去。於餾去後之溶液中加入乙酸乙酯2000ml並分取水層,將有機層以超純水400ml洗淨2次後,加入PGMEA(丙二醇單甲醚乙酸酯)1000g,將水分及低沸點溶劑餾去,藉此以聚矽氧烷化合物(C3)之PGMEA溶液600g(化合物濃度20%)的形式回收。測定聚矽氧烷化合物(C3)之聚苯乙烯換算分子量,結果Mw=2800。
[實施例、比較例]
將上述合成例中獲得之化合物(A1)~(A7)、聚矽氧烷化合物(C1)~(C3)、交聯觸媒、光酸產生劑(表3記載之PAG1~3)
、酸(馬來酸)、溶劑、水,以表1~3所示之比例混合,利用0.1μm之氟樹脂製的過濾器進行過濾,藉此分別製備含矽之阻劑下層膜形成用組成物溶液,並分別定義為Sol.1~Sol.41。
[表1]
No. | 聚矽氧烷 | 化合物 | 交聯觸媒 | 光酸產生劑 | 酸 | 溶劑 | 水 |
(質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | |
Sol.1 | C1 | A1 | TPSNO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.2 | C1 | A2 | QBANO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.3 | C1 | A3 | QBANO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.4 | C1 | A4 | TPSNO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.5 | C1 | A5 | QBANO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.6 | C1 | A6 | TPSNO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.7 | C1 | A7 | QBANO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.8 | C2 | A1 | TPSNO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.9 | C2 | A2 | QBANO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.10 | C2 | A3 | TPSNO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.11 | C2 | A4 | QBANO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.12 | C2 | A5 | TPSNO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.13 | C2 | A6 | TPSNO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 90 | 10 | |
Sol.14 | C2 | A7 | QBANO3 | 馬來酸 | PGEE | 水 | |
1.0 | 0.1 | 0.03 | 無 | 0.01 | 100 | 10 |
[表2]
No. | 聚矽氧烷 | 化合物 | 交聯觸媒 | 光酸產生劑 | 酸 | 溶劑 | 水 |
(質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | |
Sol.15 | C3 | A1 | TEAHNf | PGMEA | |||
1.0 | 0.1 | 0.03 | 無 | 無 | 100 | 無 | |
Sol.16 | C3 | A2 | TEAHNf | PGMEA | |||
1.0 | 0.1 | 0.03 | 無 | 無 | 100 | 無 | |
Sol.17 | C3 | A3 | TEAHNf | PGMEA | |||
1.0 | 0.1 | 0.03 | 無 | 無 | 100 | 無 | |
Sol.18 | C3 | A4 | TEAHNf | PGMEA | |||
1.0 | 0.1 | 0.03 | 無 | 無 | 100 | 無 | |
Sol.19 | C3 | A5 | TEAHNf | PGMEA | |||
1.0 | 0.1 | 0.03 | 無 | 無 | 100 | 無 | |
Sol.20 | C3 | A6 | TEAHNf | PGMEA | |||
1.0 | 0.1 | 0.03 | 無 | 無 | 100 | 無 | |
Sol.21 | C3 | A7 | TEAHNf | PGMEA | |||
1.0 | 0.1 | 0.03 | 無 | 無 | 100 | 無 | |
Sol.22 | C1 | A2 | QBANO3 | PAG1 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.23 | C1 | A3 | QBANO3 | PAG2 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.24 | C1 | A6 | TPSNO3 | PAG3 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.25 | C2 | A2 | QBANO3 | PAG1 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.26 | C2 | A2 | QBANO3 | PAG2 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.27 | C2 | A2 | QBANO3 | PAG3 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.28 | C2 | A3 | TPSNO3 | PAG1 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 |
[表3]
No. | 聚矽氧烷 | 化合物 | 交聯觸媒 | 光酸產生劑 | 酸 | 溶劑 | 水 |
(質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | (質量份) | |
Sol.29 | C2 | A3 | TPSNO3 | PAG2 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.30 | C2 | A3 | TPSNO3 | PAG3 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.31 | C2 | A6 | TPSNO3 | PAG1 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.32 | C2 | A6 | TPSNO3 | PAG2 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.33 | C2 | A6 | TPSNO3 | PAG3 | 馬來酸 | PGEE | 水 |
1.0 | 0.1 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.34 | C3 | A2 | TEAHNf | PAG1 | PGMEA | ||
1.0 | 0.1 | 0.03 | 0.01 | 無 | 100 | 無 | |
Sol.35 | C3 | A3 | TEAHNf | PAG2 | PGMEA | ||
1.0 | 0.1 | 0.03 | 0.01 | 無 | 100 | 無 | |
Sol.36 | C3 | A6 | TEAHNf | PAG3 | PGMEA | ||
1.0 | 0.1 | 0.03 | 0.01 | 無 | 100 | 無 | |
Sol.37 | C1 | TPSNO3 | 馬來酸 | PGEE | 水 | ||
1.0 | 無 | 0.01 | 無 | 0.01 | 90 | 10 | |
Sol.38 | C2 | QBANO3 | 馬來酸 | PGEE | 水 | ||
1.0 | 無 | 0.01 | 無 | 0.01 | 90 | 10 | |
Sol.39 | C3 | TEAHNf | PGMEA | ||||
1.0 | 無 | 0.01 | 無 | 無 | 100 | 無 | |
Sol.40 | C1 | TPSNO3 | PAG3 | 馬來酸 | PGEE | 水 | |
1.0 | 無 | 0.03 | 0.01 | 0.01 | 90 | 10 | |
Sol.41 | C2 | QBANO3 | PAG1 | 馬來酸 | PGEE | 水 | |
1.0 | 無 | 0.01 | 0.01 | 0.01 | 90 | 10 |
所使用之交聯觸媒如下。
TPSNO
3・・・硝酸三苯基鋶
QBANO
3・・・硝酸四丁基銨
TEAHNf・・・全氟丁磺酸三乙基銨
所使用之溶劑如下。
PGEE・・・丙二醇乙醚
PGMEA・・・丙二醇甲醚乙酸酯
[實施例1-1~1-36、比較例1-1~1-5]
(EUV圖案化試驗)
在矽晶圓(Si基板)上旋塗含矽之阻劑下層膜形成用組成物Sol.1~41,於220℃加熱60秒,製作膜厚25nm之含矽之阻劑下層膜Film1~41(聚矽氧烷阻劑下層膜)。
然後,將以表5之比例溶解有下列成分之阻劑材料旋塗在Film1~41上,使用加熱板於105℃預烘60秒,製作膜厚35nm之阻劑膜。將其使用ASML公司製EUV掃描曝光機NXE3300(NA0.33、σ0.9/0.6、四極照明、晶圓上尺寸為節距36nm之L/S圖案)進行曝光,在加熱板上於100℃進行60秒PEB,以2.38質量%TMAH水溶液顯影30秒,得到尺寸18nm之線。
使用日立先端科技(股)製的測長SEM(CG5000)測定該線尺寸,於線寬15nm未觀察到圖案崩塌時評價為良好,觀察到圖案崩塌時評價為不良。又,利用日立先端科技(股)製電子顯微鏡(S-4800)觀測剖面形狀(圖案形狀),未觀察到拖尾形狀時評價為良好,觀察到明顯的拖尾形狀時評價為不良。關於圖案粗糙度,利用日立先端科技(股)製電子顯微鏡(CG4000)進行觀測。
阻劑材料所使用之聚合物、淬滅劑、增感劑、界面活性劑及有機溶劑如下。
界面活性劑:3M公司製FC-4430
PGMEA:丙二醇單甲醚乙酸酯
CyHO:環己酮
PGME:丙二醇單甲醚
[表5]
成分 | 聚合物 | 淬滅劑 | 增感劑 | 界面活性劑 | 有機溶劑 |
組成 (質量份) | (100) | (4.0) | (2.1) | (0.25) | PGMEA(400) CyHO(2000) PGME(100) |
上述試驗之結果示於表6~7。
[表6]
含矽之阻劑下層膜形成用組成物 | 含矽之阻劑下層膜 | ||||
圖案崩塌 | 圖案形狀 | 圖案粗糙度 | |||
實施例1-1 | Sol.1 | Film.1 | 良好 | 良好 | 2.7 |
實施例1-2 | Sol.2 | Film.2 | 良好 | 良好 | 2.6 |
實施例1-3 | Sol.3 | Film.3 | 良好 | 良好 | 2.8 |
實施例1-4 | Sol.4 | Film.4 | 良好 | 良好 | 2.6 |
實施例1-5 | Sol.5 | Film.5 | 良好 | 良好 | 2.4 |
實施例1-6 | Sol.6 | Film.6 | 良好 | 良好 | 2.7 |
實施例1-7 | Sol.7 | Film.7 | 良好 | 良好 | 2.5 |
實施例1-8 | Sol.8 | Film.8 | 良好 | 良好 | 2.8 |
實施例1-9 | Sol.9 | Film.9 | 良好 | 良好 | 2.5 |
實施例1-10 | Sol.10 | Film.10 | 良好 | 良好 | 2.4 |
實施例1-11 | Sol.11 | Film.11 | 良好 | 良好 | 2.6 |
實施例1-12 | Sol.12 | Film.12 | 良好 | 良好 | 2.7 |
實施例1-13 | Sol.13 | Film.13 | 良好 | 良好 | 2.8 |
實施例1-14 | Sol.14 | Film.14 | 良好 | 良好 | 2.5 |
實施例1-15 | Sol.15 | Film.15 | 良好 | 良好 | 2.6 |
實施例1-16 | Sol.16 | Film.16 | 良好 | 良好 | 2.8 |
實施例1-17 | Sol.17 | Film.17 | 良好 | 良好 | 2.5 |
實施例1-18 | Sol.18 | Film.18 | 良好 | 良好 | 2.7 |
實施例1-19 | Sol.19 | Film.19 | 良好 | 良好 | 2.6 |
實施例1-20 | Sol.20 | Film.20 | 良好 | 良好 | 2.4 |
實施例1-21 | Sol.21 | Film.21 | 良好 | 良好 | 2.8 |
[表7]
含矽之阻劑下層膜形成用組成物 | 含矽之阻劑下層膜 | ||||
圖案崩塌 | 圖案形狀 | 圖案粗糙度 | |||
實施例1-22 | Sol.22 | Film.22 | 良好 | 良好 | 2.3 |
實施例1-23 | Sol.23 | Film.23 | 良好 | 良好 | 2.4 |
實施例1-24 | Sol.24 | Film.24 | 良好 | 良好 | 2.3 |
實施例1-25 | Sol.25 | Film.25 | 良好 | 良好 | 2.6 |
實施例1-26 | Sol.26 | Film.26 | 良好 | 良好 | 2.5 |
實施例1-27 | Sol.27 | Film.27 | 良好 | 良好 | 2.5 |
實施例1-28 | Sol.28 | Film.28 | 良好 | 良好 | 2.6 |
實施例1-29 | Sol.29 | Film.29 | 良好 | 良好 | 2.4 |
實施例1-30 | Sol.30 | Film.30 | 良好 | 良好 | 2.7 |
實施例1-31 | Sol.31 | Film.31 | 良好 | 良好 | 2.5 |
實施例1-32 | Sol.32 | Film.32 | 良好 | 良好 | 2.6 |
實施例1-33 | Sol.33 | Film.33 | 良好 | 良好 | 2.3 |
實施例1-34 | Sol.34 | Film.34 | 良好 | 良好 | 2.5 |
實施例1-35 | Sol.35 | Film.35 | 良好 | 良好 | 2.8 |
實施例1-36 | Sol.36 | Film.36 | 良好 | 良好 | 2.5 |
比較例1-1 | Sol.37 | Film.37 | 不良 | 不良 | 3.4 |
比較例1-2 | Sol.38 | Film.38 | 不良 | 不良 | 3.5 |
比較例1-3 | Sol.39 | Film.39 | 不良 | 不良 | 3.3 |
比較例1-4 | Sol.40 | Film.40 | 不良 | 良好 | 4.0 |
比較例1-5 | Sol.41 | Film.41 | 不良 | 良好 | 3.9 |
如表6~7所示,確認到添加了本發明之含矽之阻劑下層膜形成用組成物所必需之化合物(A1)~(A7)的實施例1-1~1-36中,觀察到抑制圖案崩塌的效果及良好的圖案形狀,且圖案粗糙度亦良好。
另一方面,比較例1-1~1-3中,由於不含本發明中使用之通式(A-1)表示之化合物,故發生了圖案崩塌,又,圖案形狀及圖案粗糙度差。另外,比較例1-4、1-5中,藉由添加PAG,觀察到圖案形狀的改善,但由於未添加通式(A-1)表示之化合物,故觀察到圖案崩塌及圖案粗糙度的劣化。由此可知,藉由添加本發明中使用之化合物(A1)~(A7),可改善線寬15nm以上之微細圖案的崩塌,不僅如此,於改善圖案的形狀及改善圖案粗糙度亦係有效。
此外,本發明不限定於上述實施形態。上述實施形態係例示,具有與本發明之專利申請範圍記載之技術思想實質相同的構成,且發揮同樣的作用效果者,均包含在本發明之技術範圍內。
Claims (9)
- 如請求項1或2之含矽之阻劑下層膜形成用組成物,更含有酸產生劑。
- 如請求項3之含矽之阻劑下層膜形成用組成物,其中,該酸產生劑為係鋶鹽且會因高能量射線之作用而產生酸的光酸產生劑。
- 一種圖案形成方法,係於被加工體形成圖案的方法, 其特徵為包含下列步驟: 於被加工體上使用塗布型有機膜材料來形成有機膜; 於該有機膜上使用如請求項1至4中任一項之含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜; 於該含矽之阻劑下層膜上使用由光阻劑組成物構成之阻劑上層膜用組成物來形成阻劑上層膜; 於該阻劑上層膜形成電路圖案; 將形成有該電路圖案之該阻劑上層膜作為遮罩,利用蝕刻將圖案轉印至該含矽之阻劑下層膜; 將轉印有該圖案之該含矽之阻劑下層膜作為遮罩,利用蝕刻對該有機膜進行圖案轉印;及 將轉印有該圖案之該有機膜作為遮罩,利用蝕刻將圖案轉印至該被加工體。
- 一種圖案形成方法,係於被加工體形成圖案的方法, 其特徵為包含下列步驟: 於被加工體上利用CVD法形成以碳作為主成分之硬遮罩; 於該硬遮罩上使用如請求項1至4中任一項之含矽之阻劑下層膜形成用組成物來形成含矽之阻劑下層膜; 於該含矽之阻劑下層膜上使用由光阻劑組成物構成之阻劑上層膜用組成物來形成阻劑上層膜; 於該阻劑上層膜形成電路圖案; 將該形成有電路圖案之阻劑上層膜作為遮罩,利用蝕刻將圖案轉印至該含矽之阻劑下層膜; 將轉印有該圖案之該含矽之阻劑下層膜作為遮罩,利用乾蝕刻對該硬遮罩進行圖案轉印;及 將轉印有該圖案之該硬遮罩作為遮罩,利用乾蝕刻將圖案轉印至該被加工體。
- 如請求項5或6之圖案形成方法,其中,於該阻劑上層膜形成電路圖案的步驟中之圖案形成,係利用波長為10nm以上300nm以下之光微影、電子束所為之直接描繪、奈米壓印或它們的組合來形成圖案。
- 如請求項5或6之圖案形成方法,其中,該被加工體為半導體裝置基板、金屬膜、金屬碳化膜、金屬氧化膜、金屬氮化膜、金屬氧化碳化膜或金屬氧化氮化膜。
- 如請求項5或6之圖案形成方法,其中,構成該被加工體之金屬為矽、鎵、鈦、鎢、鉿、鋯、鉻、鍺、銅、銀、金、銦、砷、鈀、鉭、銥、鋁、鐵、鉬、鈷或它們的合金。
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