TWI815946B - 負型感光性樹脂組成物 - Google Patents
負型感光性樹脂組成物 Download PDFInfo
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- TWI815946B TWI815946B TW108128458A TW108128458A TWI815946B TW I815946 B TWI815946 B TW I815946B TW 108128458 A TW108128458 A TW 108128458A TW 108128458 A TW108128458 A TW 108128458A TW I815946 B TWI815946 B TW I815946B
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- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- RSUCJIJELNXPQI-UHFFFAOYSA-N [4-[[4-(2-methylprop-2-enoyloxy)phenyl]methyl]phenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1CC1=CC=C(OC(=O)C(C)=C)C=C1 RSUCJIJELNXPQI-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical class CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- YENIOYBTCIZCBJ-UHFFFAOYSA-N acetic acid;1-methoxypropan-2-ol Chemical compound CC(O)=O.COCC(C)O YENIOYBTCIZCBJ-UHFFFAOYSA-N 0.000 description 1
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- 150000005215 alkyl ethers Chemical class 0.000 description 1
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- FVFZFANLRPXUIE-UHFFFAOYSA-N anthracen-1-yl 2-methylprop-2-enoate Chemical compound C1=CC=C2C=C3C(OC(=O)C(=C)C)=CC=CC3=CC2=C1 FVFZFANLRPXUIE-UHFFFAOYSA-N 0.000 description 1
- LTGVWEPMIDGXKP-UHFFFAOYSA-N anthracen-1-yl prop-2-enoate Chemical compound C1=CC=C2C=C3C(OC(=O)C=C)=CC=CC3=CC2=C1 LTGVWEPMIDGXKP-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
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- LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 1
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- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- ITXCLKMRLHBUEP-UHFFFAOYSA-N bis(2-methylbutan-2-yl) 4-[3,4-bis(2-methylbutan-2-ylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)CC)C(C(=O)OOC(C)(C)CC)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)CC)C(C(=O)OOC(C)(C)CC)=C1 ITXCLKMRLHBUEP-UHFFFAOYSA-N 0.000 description 1
- YGWAFVKXCAQAGJ-UHFFFAOYSA-N bis(2-methylpentan-2-yl) 4-[3,4-bis(2-methylpentan-2-ylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)CCC)C(C(=O)OOC(C)(C)CCC)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)CCC)C(C(=O)OOC(C)(C)CCC)=C1 YGWAFVKXCAQAGJ-UHFFFAOYSA-N 0.000 description 1
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- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
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- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
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- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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Abstract
本發明係關於提供一種新穎負型感光性樹脂組成物。
本發明的解決手段為:
一種負型感光性樹脂組成物,其為含有下述(A)成分、(B)成分、(C)成分,及溶劑者;對於該(A)成分100質量%而言為80質量%至90質量%的下述(B)成分,對於該(B)成分之總量100質量%而言為3質量%至20質量%的下述(C)成分;
(A):鹼可溶性聚合物
(B):於1分子中具有2個以上選自由丙烯醯基氧基、甲基丙烯醯基氧基、烯丙基及乙烯基所成群的聚合性基之至少2種的交聯性化合物
(C):至少1種的光聚合起始劑。
Description
本發明係關於一種含有鹼可溶性聚合物、至少2種交聯性化合物、至少1種光聚合起始劑及溶劑的負型感光性樹脂組成物者。特別為有關使用於微鏡形成的負型感光性樹脂組成物者。
自過去,對於CCD/CMOS圖像傳感器等電子裝置上欲提高集光效率而設有微鏡。作為CCD/CMOS圖像傳感器用微鏡的製作方法之1,已知有回蝕(Etch back)方法(專利文獻1及專利文獻2)。即,在於彩色過濾器上所形成的微鏡用樹脂層上形成阻劑圖型,藉由熱處理,將該阻劑圖型進行回流後形成透鏡圖型。將該阻劑圖型進行回流所形成的透鏡圖型作為蝕刻光罩,將下層的微鏡用樹脂層進行回蝕,藉由將透鏡圖型形狀於微鏡用樹脂層進行轉印而製作出微鏡。如此微鏡的耐藥品性、高透明性等各種特性被要求著。
又,僅在CCD/CMOS圖像傳感器、液晶顯示及有機EL顯示等電子裝置元件上的任意處使膜進行圖型形成時,要求其光刻性。對於如此感光性材料,要求以低曝光量形成圖型(感度特性),及可抑制鹼顯像後的殘渣產生。
然而,已有含有馬來醯亞胺系共聚物的微鏡形成用感光性樹脂組成物(專利文獻3)、含有三嗪骨架的正型阻劑組成物(專利文獻4)被提案。但這些專利文獻因為了要滿足上述諸特性,特別滿足耐溶劑性,必須要在超過100℃,例如在140℃至260℃的高溫下加熱,在100℃以下的低溫加熱下未能滿足前述特性。
[先前技術文獻]
[專利文獻]
[專利文獻1] 日本特開平1-10666號公報
[專利文獻2] 日本特開平6-112459號公報
[專利文獻3] 日本專利第5867735號公報
[專利文獻4] 日本專利第5673963號公報
[發明所解決的問題]
本發明係以前述情事為基礎者,該所要解決的課題為提供一種在100℃的烘烤溫度下所得的膜可顯著改善高透明性、耐溶劑性、感度特性及未曝光部的殘渣之負型感光性樹脂組成物。
[解決課題的手段]
本發明者們,欲解決前述課題而進行詳細檢討結果而完成本發明。即,本發明為一種含有下述(A)成分,對於該(A)成分100質量%而言為80質量%至90質量%的下述(B)成分、對於該(B)成分的總量100質量%而言為3質量%至20質量%的下述(C)成分,及溶劑之負型感光性樹脂組成物。
(A):鹼可溶性聚合物
(B):於1分子中具有2個以上選自由丙烯醯基氧基、甲基丙烯醯基氧基、烯丙基及乙烯基所成群的聚合性基之至少2種的交聯性化合物
(C):至少1種的光聚合起始劑
前述至少2種的交聯性化合物,例如含有:作為前述聚合性基,於1分子中具有2個丙烯醯基氧基或甲基丙烯醯基氧基的交聯性化合物,及作為前述聚合性基,於1分子中具有3個以上的丙烯醯基氧基或甲基丙烯醯基氧基的交聯性化合物。
前述鹼可溶性聚合物,例如具有選自由下述式(1a)、式(1b)、式(1c)、式(1d)及式(1e)所成群的結構單位。
(式中,R1
表示氫原子或甲基,A表示-O-基或-NH-基,X表示單鍵、碳原子數1至3的伸烷基,或含有碳原子數1至3的伸烷氧基之二價的連結基,Z1
表示羥基苯基或羧基苯基,Z2
表示羥基苯基、羧基苯基或羧基,Z3
表示氫原子、羥基苯基或羧基苯基)。
前述二價的連結基,例表示前述碳原子數1至3的伸烷氧基,或2個以上的該碳原子數1至3的伸烷氧基經鍵結的基。
前述鹼可溶性聚合物,例如為進一步具有與前述結構單位相異的選自由下述式(2a)、式(2b)及式(2c)所成群的結構單位之共聚物。
(式中,R1
表示氫原子或甲基,A表示-O-基或-NH-基,X表示單鍵、碳原子數1至3的伸烷基,或含有碳原子數1至3的伸烷氧基之二價的連結基,Z4
表示碳原子數1至3的直鏈狀之有機基,或碳原子數3至14的分支鏈狀或者環狀之有機基)。
前述二價的連結基,例如表示由前述碳原子數1至3的伸烷氧基,或該碳原子數1至3的伸烷氧基以2個以上進行鍵結的基。前述有機基可具有至少1個之氮原子、氧原子等雜原子,亦可於2個碳原子之間或於碳原子與雜原子之間具有雙鍵或參鍵。作為前述環狀的有機基,例如可舉出芳香族烴基、脂環式烴基、交聯環烴基、雜環基。
本發明之負型感光性樹脂組成物,例如使用於微鏡形成上。
本發明又為一種微鏡的製造方法,其為具有:將前述負型感光性樹脂組成物塗布於基板上,並經預烘烤後形成樹脂膜之步驟、通過光罩而使前述樹脂膜進行曝光的步驟、將前述曝光後的樹脂膜使用鹼性顯像液使其顯像的步驟,及使前述顯像後的樹脂膜之全面進行曝光的步驟。
於將前述顯像後的樹脂膜之全面進行曝光的步驟之後或該步驟之前,可進一步具有使該樹脂膜進行後烘烤的步驟。
[發明之效果]
本發明之負型感光性樹脂組成物為,藉由使鹼可溶性聚合物、至少2種交聯性化合物,及至少1種光聚合起始劑之添加量最適化,可得使用該組成物在100℃的烘烤溫度下所得之膜具有高透明,且高感度下未曝光部的殘渣為少,對於溶劑耐性亦優良者。因此,本發明之負型感光性樹脂組成物可作為形成微鏡的材料而適用。
[實施發明的型態]
本發明的負型感光性樹脂組成物為含有(A)成分、對於該(A)成分100質量%而言為80質量%至90質量%的(B)成分、對於該(B)成分的總量100質量%而言為3質量%至20質量%的(C)成分,及溶劑。以下詳細說明本發明之各成分。由本發明之負型感光性樹脂組成物中除去溶劑的固體成分,通常為1質量%至50質量%。對於本說明書,將除去溶劑的本發明之負型感光性樹脂組成物之成分定義為固體成分。
<(A)成分>
於本發明之負型感光性樹脂組成物中之(A)成分為鹼可溶性聚合物。該聚合物為含有以下原料單體的聚合物,該原料單體為含有具有鹼可溶性基之單體及任意的其他單體者。(A)成分的鹼可溶性聚合物僅具有鹼可溶性基即可,對於構成該聚合物的高分子之主鏈的骨架及側鏈之種類等並無特別限定。前述鹼可溶性聚合物之重量平均分子量,例如為1000至50000,較佳為3000至40000。且,重量平均分子量藉由凝膠滲透層析法(GPC),使用作為標準試料的聚苯乙烯而得到的值。
作為前述具有鹼可溶性基的單體,例如可舉出具有羧基的單體、具有酚性羥基的單體、具有酸酐基的單體、具有馬來醯亞胺基的單體。
作為具有前述羧基的單體,例如可舉出丙烯酸、甲基丙烯酸、巴豆酸、單-(2-(丙烯醯氧基)乙基)鄰苯二甲酸酯、單-(2-(甲基丙烯醯氧)乙基)鄰苯二甲酸酯、N-(羧基苯基)馬來醯亞胺、N-(羧基苯基)甲基丙烯醯胺、N-(羧基苯基)丙烯醯胺、4-乙烯基安息香酸。
作為前述具有酚性羥基的單體,例如可舉出羥基苯乙烯、N-(羥基苯基)丙烯醯胺、N-(羥基苯基)甲基丙烯醯胺、N-(羥基苯基)馬來醯亞胺。
作為前述具有酸酐基的單體,例如可舉出馬來酸酐、衣康酸酐。
作為前述具有馬來醯亞胺基的單體,例如可舉出前述N-(羧基苯基)馬來醯亞胺及N-(羥基苯基)馬來醯亞胺、馬來醯亞胺。
前述具有鹼可溶性基的單體之中,亦以含有選自由丙烯酸、甲基丙烯酸、馬來酸酐及馬來醯亞胺所成群的至少1種之單體的聚合物為佳。
又,(A)成分的鹼可溶性聚合物可為前述具有鹼可溶性基的單體與其他單體之共聚物。該共聚物並未限定於由2種單體所得之共聚物,亦可由3種單體所得的三元共聚物(Terpolymer)。作為前述其他單體之具體例子,例如可舉出丙烯酸酯化合物、甲基丙烯酸酯化合物、N-取代馬來醯亞胺化合物、丙烯腈化合物、丙烯醯胺化合物、甲基丙烯醯胺化合物、苯乙烯化合物及乙烯基化合物。以下可舉出前述其他單體之具體例子,但並未限定於此等。
作為前述丙烯酸酯化合物,例如可舉出甲基丙烯酸酯、乙基丙烯酸酯、異丙基丙烯酸酯、苯甲基丙烯酸酯、萘丙烯酸酯、蒽基丙烯酸酯、蒽基甲基丙烯酸酯、苯基丙烯酸酯、苯氧基乙基丙烯酸酯、2,2,2-三氟乙基丙烯酸酯、tert-丁基丙烯酸酯、環己基丙烯酸酯、異冰片基丙烯酸酯、2-甲氧基乙基丙烯酸酯、甲氧基三乙二醇丙烯酸酯、2-乙氧基乙基丙烯酸酯、四氫糠基丙烯酸酯、3-甲氧基丁基丙烯酸酯、2-甲基-2-金剛烷基丙烯酸酯、2-丙基-2-金剛烷基丙烯酸酯、8-甲基-8-三環癸基丙烯酸酯、2-羥基乙基丙烯酸酯、2-羥基丙基丙烯酸酯、4-羥基丁基丙烯酸酯、2,3-二羥基丙基丙烯酸酯、二乙二醇單丙烯酸酯、己內酯2-(丙烯醯氧基)乙基酯、聚(乙二醇)乙基醚丙烯酸酯、5-丙烯醯氧基-6-羥基降冰片烯-2-羧酸-6-內酯、丙烯醯氧基乙基異氰酸酯、8-乙基-8-三環癸基丙烯酸酯、縮水甘油基丙烯酸酯。
作為前述甲基丙烯酸酯化合物,例如可舉出甲基丙烯酸甲酯、乙基甲基丙烯酸酯、異丙基甲基丙烯酸酯、苯甲基丙烯酸甲酯、萘甲基丙烯酸酯、蒽基甲基丙烯酸酯、蒽基甲基丙烯酸甲酯、苯基甲基丙烯酸酯、苯氧基乙基甲基丙烯酸酯、2,2,2-三氟乙基甲基丙烯酸酯、tert-丁基甲基丙烯酸酯、環己基甲基丙烯酸酯、異冰片基甲基丙烯酸酯、2-甲氧基乙基甲基丙烯酸酯、甲氧基三乙二醇甲基丙烯酸酯、2-乙氧基乙基甲基丙烯酸酯、四氫糠基甲基丙烯酸酯、3-甲氧基丁基甲基丙烯酸酯、2-甲基-2-金剛烷基甲基丙烯酸酯、γ-丁內酯甲基丙烯酸酯、2-丙基-2-金剛烷基甲基丙烯酸酯、8-甲基-8-三環癸基甲基丙烯酸酯、2-羥基乙基甲基丙烯酸酯、2-羥基丙基甲基丙烯酸酯、4-羥基丁基甲基丙烯酸酯、2,3-二羥基丙基甲基丙烯酸酯、二乙二醇單甲基丙烯酸酯、己內酯2-(甲基丙烯醯氧)乙基酯、聚(乙二醇)乙基醚甲基丙烯酸酯、5-甲基丙烯醯氧-6-羥基降冰片烯-2-羧酸-6-內酯、甲基丙烯醯氧乙基異氰酸酯、8-乙基-8-三環癸基甲基丙烯酸酯、縮水甘油基甲基丙烯酸酯。
作為前述乙烯基化合物,例如可舉出甲基乙烯基醚、苯甲基乙烯基醚、乙烯基萘、乙烯基蒽、乙烯基聯苯基、乙烯基咔唑、2-羥基乙基乙烯基醚、苯基乙烯基醚、丙基乙烯基醚。
作為前述苯乙烯化合物,例如可舉出苯乙烯、甲基苯乙烯、氯苯乙烯、溴苯乙烯。
作為前述N-取代馬來醯亞胺化合物,例如可舉出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。
作為前述丙烯腈化合物,例如可舉出丙烯腈。
且,作為具有鹼可溶性基的單體與其他單體之裝入比,以具有鹼可溶性基的單體/其他單體=5至50質量%/50至95質量%者為佳。對於其他單體的具有鹼可溶性基的單體之裝入比若過少時,未曝光部會不溶解於顯像液中而容易成為殘膜或殘渣之原因。又,對於其他單體的具有鹼可溶性基的單體之裝入比若過多時,曝光部之硬化性會不足,而有無法形成圖型之可能性。
得到(A)成分的鹼可溶性聚合物之方法並無特別限定,但一般為藉由將含有上述具有鹼可溶性基的單體之原料單體,在聚合溶劑中,通常50℃至110℃之溫度下使其進行聚合反應而得。
藉由前述方法所得的鹼可溶性聚合物具有選自由前述式(1a)、式(1b)、式(1c)、式(1d)及式(1e)所成群的結構單位。該鹼可溶性聚合物可進一步具有與前述結構單位相異的選自由前述式(2a)、式(2b)及式(2c)所成群的結構單位。
於本發明之負型感光性樹脂組成物中之(A)成分的含有量,依據該組成物之固體成分中的含有量,通常為48質量%至55質量%。
<(B)成分>
於本發明之負型感光性樹脂組成物中之(B)成分為,於1分子中具有2個以上選自由丙烯醯基氧基、甲基丙烯醯基氧基、烯丙基及乙烯基所成群的聚合性基之至少2種的交聯性化合物。作為(B)成分,以於1分子中具有2個該聚合性基之交聯性化合物,與於1分子中具有3個以上的該聚合性基之交聯性化合物的組合者為佳。該聚合性基存在於交聯性化合物之分子末端。
(B)成分之交聯性化合物,由與本發明之負型感光性樹脂組成物的其他成分之相溶性良好,且對於顯影性未有影響的觀點來看,以重量平均分子量200至1,000之化合物為佳。
作為前述交聯性化合物,例如可舉出二季戊四醇六丙烯酸酯、二季戊四醇六甲基丙烯酸酯、二季戊四醇五丙烯酸酯、二季戊四醇五甲基丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇四甲基丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇三甲基丙烯酸酯、季戊四醇二丙烯酸酯、季戊四醇二甲基丙烯酸酯、四羥甲基丙烷四丙烯酸酯、四羥甲基丙烷四甲基丙烯酸酯、四羥甲基甲烷四丙烯酸酯、四羥甲基甲烷四甲基丙烯酸酯、三羥甲基丙烷三丙烯酸酯、三羥甲基丙烷三甲基丙烯酸酯、1,3,5-三丙烯醯基六氫-S-三嗪、1,3,5-三甲基丙烯醯基六氫-S-三嗪、參(羥基乙基丙烯醯基)異氰脲酸酯、參(羥基乙基甲基丙烯醯基)異氰脲酸酯、三丙烯醯基甲醛、三甲基丙烯醯基甲醛、1,6-己二醇丙烯酸酯、1,6-己二醇甲基丙烯酸酯、新戊二醇二丙烯酸酯、新戊二醇二甲基丙烯酸酯、乙烷二醇二丙烯酸酯、乙烷二醇二甲基丙烯酸酯、2-羥基丙烷二醇二丙烯酸酯、2-羥基丙烷二醇二甲基丙烯酸酯、二乙二醇二丙烯酸酯、二乙二醇二甲基丙烯酸酯、異丙二醇二丙烯酸酯、異丙二醇二甲基丙烯酸酯、三乙二醇二丙烯酸酯、三乙二醇二甲基丙烯酸酯、N,N’-雙(丙烯醯基)半胱胺酸、N,N’-雙(甲基丙烯醯基)半胱胺酸、硫代二甘醇二丙烯酸酯、硫代二甘醇二甲基丙烯酸酯、雙酚A二丙烯酸酯、雙酚A二甲基丙烯酸酯、雙酚F二丙烯酸酯、雙酚F二甲基丙烯酸酯、雙酚S二丙烯酸酯、雙酚S二甲基丙烯酸酯、雙苯氧基乙醇芴二丙烯酸酯、雙苯氧基乙醇芴二甲基丙烯酸酯、二烯丙基醚雙酚A、o,o’-二烯丙基雙酚A、馬來酸二烯丙基、三烯丙基偏苯三酸酯。
前述交聯性化合物,可作為販售品而容易入手,例如可舉出KAYARAD(註冊商標)T-1420、同DPHA、同DPHA-2C、同D-310、同D-330、同DPCA-20、同DPCA-30、同DPCA-60、同DPCA-120、同DN-0075、同DN-2475、同R-526、同NPGDA、同PEG400DA、同MANDA、同R-167、同HX-220、同HX620、同R-551、同R-712、同R-604、同R-684、同GPO-303、同TMPTA、同THE-330、同TPA-320、同TPA-330、同PET-30、同RP-1040(以上為日本化藥(股)製);Aronix(註冊商標)M-210、同M-208、同M-211B、同M-215、同M-220、同M-225、同M-270、同M-240、同M-6100、同M-6250、同M-6500、同M-6200、同M-309、同M-310、同M-321、同M-350、同M-360、同M-313、同M-315、同M-306、同M-303、同M-452、同M-408、同M-403、同M-400、同M-402、同M-405、同M-406、同M-450、同M-460、同M-510、同M-520、同M-1100、同M-1200、同M-6100、同M-6200、同M-6250、同M-6500、同M-7100、同M8030、同M8060、同M8100、同M8530、同M-8560、同M9050(以上為東亞合成(股)製);Biscote295、同300、同360、同GPT、同3PA、同400、同260、同312、同335HP、同700(以上為大阪有機化學工業(股)製);A-200、A-400、A-600、A-1000、AB1206PE、ABE-300、A-BPE-10、A-BPE-20、A-BPE-30、A-BPE-4、A-BPEF、A-BPP-3、A-DCP、A-DOD-N、A-HD-N、A-NOD-N、APG-100、APG-200、APG-400、APG-700、A-PTMG-65、A-9300、A-9300-1CL、A-GLY-9E、A-GLY-20E、A-TMM-3、A-TMM-3L、A-TMM-3LM-N、A-TMPT、AD-TMP、ATM-35E、A-TMMT、A-9550、A-DPH、TMPT、9PG、701A、1206PE、NPG、NOD-N、HD-N、DOD-N、DCP、BPE-1300N、BPE-900、BPE-200、BPE-100、BPE-80N、23G、14G、9G、4G、3G、2G、1G(以上為新中村化學工業(股)製);Light esterEG、同2EG、同3EG、同4EG、同9EG、同14EG、同1.4BG、同NP、同1.6HX、同1.9ND、同G-101P、同G-201P、同DCP-M、同BP-2EMK、同BP-4EM、同BP-6EM、同TMP、light丙烯酸酯3EG-A、同4EG-A、同9EG-A、同14EG-A、同PTMGA-250、同NP-A、同MPD-A、同1.6HX-A、同1.9ND-A、同MOD-A、同DCP-A、同BP-4PA、同BA-134、同BP-10EA、同HPP-A、同G-201P、同TMP-A、同TMP-3EO-A、同TMP-6EO-3A、同PE-3A、同PE-4A、同DPE-6A、環氧酯40EM、同70PA、同200PA、同80MFA、同3002M、同3002A、同3000MK、同3000A、同EX-0205、AH-600、AT-600、UA-306H、UA-306T、UA-306I、UA-510H、UF-8001G、DAUA-167(共榮公司化學(股)製);EBECRYL(註冊商標)TPGDA、同145、同150、同PEG400DA、同11、同HPNDA、同PETIA、同PETRA、同TMPTA、同TMPEOTA、同OTA480、同DPHA、同180、同40、同140、同204、同205、同210、同215、同220、同6202、同230、同244、同245、同264、同265、同270、同280/15IB、同284、同285、同294/25HD、同1259、同KRM8200、同4820、同4858、同5129、同8210、同8301、同8307、同8402、同8405、同8411、同8804、同8807、同9260、同9270、同KRM7735、同KRM8296、同KRM8452、同8311、同8701、同9227EA、同80、同436、同438、同446、同450、同505、同524、同525、同770、同800、同810、同811、同812、同1830、同846、同851、同852、同853、同1870、同884、同885、同600、同605、同645、同648、同860、同1606、同3500、同3608、同3700、同3701、同3702、同3703、同3708、同6040(大賽璐・Ornex(股)製);SR212、SR213、SR230、SR238F、SR259、SR268、SR272、SR306H、SR344、SR349、SR508、CD560、CD561、CD564、SR601、SR602、SR610、SR833S、SR9003、CD9043、SR9045、SR9209、SR205、SR206、SR209、SR210、SR214、SR231、SR239、SR248、SR252、SR297、SR348、SR480、CD540、CD541、CD542、SR603、SR644、SR9036、SR351S、SR368、SR415、SR444、SR454、SR492、SR499、CD501、SR502、SR9020、CD9021、SR9035、SR350、SR295、SR355、SR399、SR494、SR9041(Sartomer公司製)。
(B)成分之交聯性化合物可組合2種以上而使用。作為2種以上之組合,以於1分子中具有2個聚合性基之交聯性化合物及於1分子中具有3個以上聚合性基之交聯性化合物者為佳。作為該於1分子中具有3個以上聚合性基之交聯性化合物,亦可為聚合性基之數為相異的2種以上的交聯性化合物之組合。又,作為該聚合性基,以丙烯醯基氧基或甲基丙烯醯基氧基為佳。
本發明之負型感光性樹脂組成物中之(B)成分的含有量,對於(A)成分100質量%而言為80質量%至90質量%。
<(C)成分>
於本發明之負型感光性樹脂組成物中之(C)成分為至少1種的光聚合起始劑。(C)成分之光聚合起始劑若為於使用於光硬化時的光源上具有吸收者即可,並無特別限定。
作為前述光聚合起始劑,例如可舉出tert-丁基過氧基-iso-丁酸酯、2,5-二甲基-2,5-雙(苯甲醯基二氧基)己烷、1,4-雙[α-(tert-丁基二氧基)-iso-丙氧基]苯、二-tert-丁基過氧化物、2,5-二甲基-2,5-雙(tert-丁基二氧基)己烯過氧化氫、α-(iso-丙基苯基)-iso-丙基過氧化氫、tert-丁基過氧化氫、1,1-雙(tert-丁基二氧基)-3,3,5-三甲基環己烷、丁基-4,4-雙(tert-丁基二氧基)戊酸酯、環己酮過氧化物、2,2’,5,5’-四(tert-丁基過氧羰基)二苯甲酮、3,3’,4,4’-四(tert-丁基過氧羰基)二苯甲酮、3,3’,4,4’-四(tert-戊基過氧羰基)二苯甲酮、3,3’,4,4’-四(tert-己基過氧羰基)二苯甲酮、3,3’-雙(tert-丁基過氧羰基)-4,4’-二羧基二苯甲酮、tert-丁基過氧基苯甲酸酯、二-tert-丁基二過氧基間苯二甲酸酯等的有機過氧化物;9,10-蒽醌、1-氯蒽醌、2-氯蒽醌、八甲基蒽醌、1,2-苯並蒽醌等的醌類;安息香甲基、安息香乙基醚、α-甲基安息香、α-苯基安息香等的安息香衍生物;2,2-二甲氧基-1,2-二苯基乙烷-1-酮、1-羥基環己基苯基酮、2-羥基-2-甲基-1-苯基-丙烷-1-酮、1-[4-(2-羥基乙氧基)-苯基]-2-羥基-2-甲基-1-丙烷-1-酮、2-羥基-1-[4-{4-(2-羥基-2-甲基-丙醯基)苯甲基}-苯基]-2-甲基-丙烷-1-酮、苯基乙醛酸甲基酯、2-甲基-1-[4-(甲基硫基)苯基]-2-嗎啉代丙烷-1-酮、2-苯甲基-2-二甲基胺基-1-(4-嗎啉代苯基)-1-丁酮、2-二甲基胺基-2-(4-甲基-苯甲基)-1-(4-嗎啉-4-基-苯基)-丁烷-1-酮等的烷基苯乙酮系化合物;雙(2,4,6-三甲基苯甲醯基)-苯基膦氧化物、2,4,6-三甲基苯甲醯基-二苯基-膦氧化物等的醯膦氧化物系化合物;2-(O-苯甲醯肟)-1-[4-(苯基硫基)苯基]-1,2-辛烷二酮、1-(O-乙醯肟)-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]乙酮等的肟酯系化合物。
前述光聚合起始劑可作為販售品而入手,例如可舉出OMNIRAD(註冊商標)651、同184、同500、同2959、同127、同754、同907、同369、同379、同379EG、同819、同819DW、同1700、同1870、同784、同1173、同MBF、同4265、同TPO(以上為IGM Resins公司製)[舊IRGACURE(註冊商標)651、同184、同500、同2959、同127、同754、同907、同369、同379、同379EG、同819、同819DW、同1700、同1870、同784、同1173、同MBF、同4265、同TPO(以上為BASFJapan(股)製)]、IRGACURE(註冊商標)1800、同OXE01、同OXE02 (以上為BASFJapan(股)製)、KAYACURE(註冊商標) DETX、同MBP、同DMBI、同EPA、同OA(以上為日本化藥(股)製)、VICURE-10、同55(以上為STAUFFER Co.LTD製)、ESACURE(註冊商標)KIP150、同TZT、同1001、同KTO46、同KB1、同KL200、同KS300、同EB3、三嗪-PMS、三嗪A、三嗪B(以上為DKSHJapan(股)製)、ADEKA OPTOMERN-1717、同N-1414、同N-1606((股)ADEKA製)。
(C)成分的光聚合起始劑可單獨使用1種或組合2種以上而使用。
本發明之負型感光性樹脂組成物中之(C)成分的含有量,對於(B)成分之總量100質量%而言為3質量%至20質量%。
<溶劑>
本發明之負型感光性樹脂組成物為含有溶劑。作為該溶劑,僅可溶解前述(A)成分、(B)成分及(C)成分者即可,並無特別限定。
作為前述溶劑,例如可舉出乙二醇單甲基醚、乙二醇單乙基醚、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、二乙二醇單甲基醚、二乙二醇單乙基醚、丙二醇、丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、丙二醇丙基醚乙酸酯、丙二醇單丁基醚、丙二醇單丁基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、環戊酮、環己酮、2-羥基丙酸乙基、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-甲基丁烷酸甲酯、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、乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯、2-庚酮、γ-丁內酯。
前述溶劑之中,亦由塗膜之塗平性的提高之觀點來看,以丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、2-庚酮、乳酸乙酯、乳酸丁酯及環己酮為佳。
前述溶劑可單獨使用1種或組合2種以上而使用。
<界面活性劑>
本發明之負型感光性樹脂組成物以提高塗布性作為目的,可含有界面活性劑。作為該界面活性劑,例如可舉出聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯十六烷基醚、聚氧乙烯油基醚等的聚氧乙烯烷基醚類、聚氧乙烯辛基苯基醚、聚氧乙烯壬基苯基醚等的聚氧乙烯烷基芳基醚類、聚氧乙烯・聚氧伸丙基嵌段共聚物類、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、聚氧乙烯山梨糖醇單月桂酸酯、聚氧乙烯山梨糖醇單棕櫚酸酯、聚氧乙烯山梨糖醇單硬脂酸酯、聚氧乙烯山梨糖醇三油酸酯、聚氧乙烯山梨糖醇三硬脂酸酯等的聚氧乙烯山梨糖醇脂肪酸酯類等的非離子系界面活性劑、EFTOP(註冊商標)EF301、同EF303、同EF352(以上為MITSUBISHI MATERIAL電子化成(股)製)、Megafac(註冊商標)F-171、同F-173、同R-30、同R-40、同R-40-LM(以上為DIC(股)製)、FLUORADFC430、同FC431(以上為3MJapan(股)製)、Asahi Guard(註冊商標)AG710、Surflon(註冊商標)S-382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106 (AGC(股)製)、FTX-206D、FTX-212D、FTX-218、FTX-220D、FTX-230D、FTX-240D、FTX-212P、FTX-220P、FTX-228P、FTX-240G等Footagent系列((股)Neos製)等的氟系界面活性劑、有機矽氧烷聚合物KP341(信越化學工業(股)製)。
前述界面活性劑可單獨使用1種或組合2種以上而使用。又,前述界面活性劑被使用時,於本發明之負型感光性樹脂組成物中之該含有量為依據該組成物之固體成分中的含有量時為3質量%以下,例如為0.0001質量%至3質量%,以0.001質量%至1質量%為佳,較佳為0.01質量%至0.5質量%。
<其他添加劑>
本發明之負型感光性樹脂組成物在不損害本發明之效果下,視必要可將硬化助劑、紫外線吸收劑、增感劑、可塑劑、抗氧化劑、密著助劑或多價酚、多元羧酸等溶解促進劑作為其他添加劑而含有。
<組成物之調製方法>
本發明之負型感光性樹脂組成物的調製方法並無特別限定,例如可舉出將(A)成分的鹼可溶性聚合物溶解於前述溶劑中,於所得之溶液中,將(B)成分之交聯性化合物及(C)成分之光聚合起始劑以所定比例進行混合,成為均勻溶液之方法。進一步可舉出於該調製方法之適當階段,視必要進一步添加前述其他添加劑而進行混合之方法。
<負型感光性樹脂組成物之使用>
於基板[例如以氧化矽膜包覆的矽等半導體基板、以氮化矽膜或氧化氮化矽膜包覆的矽等半導體基板、氮化矽基板、石英基板、玻璃基板(含有無鹼玻璃、低鹼玻璃、結晶化玻璃)、以銦錫氧化物(ITO)膜所形成的玻璃基板]上,藉由旋塗器、塗佈機等適當塗布方法,塗布本發明之負型感光性樹脂組成物,其後,使用加熱板等加熱手段藉由預烘烤而形成塗膜。
作為前述預烘烤條件,適宜地選自烘烤溫度80℃至150℃、烘烤時間0.3至60分鐘之中,以烘烤溫度80℃至100℃,烘烤時間0.5至5分鐘為佳。
又,作為由本發明之負型感光性樹脂組成物所形成的膜之膜厚,例如為0.005μm至20μm,較佳為0.01μm至15μm。
其次於所得之前述膜上,欲形成所定圖型而通過光罩(Reticle)進行曝光。曝光為,例如可使用g線、i線、KrF準分子激光。曝光後,視必要進行曝光後加熱(Post Exposure Bake)。作為曝光後加熱之條件,可適宜地選自加熱溫度80℃至100℃、加熱時間0.3至60分鐘之中。然後以鹼性顯像液進行顯像。
作為前述鹼性顯像液,例如可舉出氫氧化鉀、氫氧化鈉等的鹼金屬氫氧化物之水溶液、氫氧化四甲基銨、氫氧化四乙基銨、科林等的氫氧化四級銨之水溶液、乙醇胺、丙基胺、乙二胺等的胺水溶液等的鹼性水溶液。這些顯像液中可進一步添加界面活性劑。
作為顯像之條件,可適宜地選自顯像溫度5℃至50℃、顯像時間10秒至300秒。由本發明之負型感光性樹脂組成物所形成的膜為,使用氫氧化四甲基銨水溶液,在室溫下可容易地進行顯像。顯像後,使用作為輕洗(rinse)液,例如超純水進行適宜的輕洗。
其後,例如使用g線、i線或KrF準分子激光,將顯像後的膜進行全面曝光。進一步於全面曝光之前或後,可使用對顯像後之膜的加熱板等加熱手段進行後烘烤。作為後烘烤條件,例如可適宜地選自烘烤溫度80℃至100℃、烘烤時間0.5分至60分鐘之中。
[實施例]
以下舉出合成例及實施例而更詳細說明本發明,但本發明並未限定於下述實施例。
[重量平均分子量之測定]
裝置:日本分光(股)製GPC系統
管柱:Shodex[註冊商標]GPC KF-804L及GPC KF-803L
管柱烤箱:40℃
流量:1ml/分
溶離液:四氫呋喃
標準資料:聚苯乙烯
[合成例1]
將甲基丙烯酸60g、甲基丙烯酸甲基240g,及2,2’-偶氮二異丁腈7.6g溶解於丙二醇單甲基醚132g後,將該溶液經3小時滴入於保持在70℃的放有丙二醇單甲基醚440g之燒瓶中。滴入終了後,藉由進行18小時反應後,得到具有下述式(1b-1)所示結構單位及下述式(2a-1)所示結構單位之鹼可溶性聚合物(共聚物)的溶液(固體成分濃度35質量%)。所得之共聚物的重量平均分子量Mw為35,000(聚苯乙烯換算)。
[合成例2]
將甲基丙烯酸61g、甲基丙烯酸甲基122g、苯乙烯122g及2,2’-偶氮二異丁腈7.6g溶解於丙二醇單甲基醚134g後,將該溶液經3小時滴入於保持在70℃之放有丙二醇單甲基醚446g之燒瓶中。滴入終了後,藉由進行18小時反應,得到具有下述式(1b-1)所示結構單位、下述式(2a-1)所示結構單位及下述式(2b-1)所示結構單位之鹼可溶性聚合物(三元共聚物)之溶液(固體成分濃度35質量%)。所得之共聚物的重量平均分子量Mw為35,000(聚苯乙烯換算)。
[實施例1]
將在合成例1所得之(A)成分的鹼可溶性聚合物之溶液(固體成分濃度35質量%)19.7g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)3.4g及ABE-300(新中村化學工業(股)製)2.1g、作為(C)成分之光聚合起始劑的IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.21g及OMNIRAD(註冊商標)184(IGM Resins公司製)[舊
IRGACURE(註冊商標)184(BASFJapan(股)製)]0.62g以及作為界面活性劑的DFX-18(Neos(股)製)0.0040g,溶解於丙二醇單甲基醚5.6g及丙二醇單甲基醚乙酸酯18.4g作成溶液。此後,使用孔徑1μm之聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。
[實施例2]
將在合成例1所得之(A)成分的鹼可溶性聚合物的溶液(固體成分濃度35質量%)19.6g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)4.1g及ABE-300(新中村化學工業(股)製)2.1g、作為(C)成分的光聚合起始劑之
IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.21g,以及作為界面活性劑的DFX-18(Neos(股)製)0.0040g,溶解於丙二醇單甲基醚5.6g及丙二醇單甲基醚乙酸酯18.4g中成為溶液。其後,使用孔徑1μm之聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。
[實施例3]
將在合成例1所得的(A)成分之鹼可溶性聚合物的溶液(固體成分濃度35質量%)18.8g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)3.9g及ABE-300(新中村化學工業(股)製)2.0g、作為(C)成分的光聚合起始劑之IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.20g及OMNIRAD(註冊商標)184(IGM Resins公司製)[舊
IRGACURE(註冊商標)184(BASFJapan(股)製)]0.59g,以及作為界面活性劑的DFX-18(Neos(股)製)0.0040g,溶解於丙二醇單甲基醚6.2g及丙二醇單甲基醚乙酸酯18.4g而作成溶液。其後,使用孔徑1μm之聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。
[實施例4]
將在合成例2所得之(A)成分的鹼可溶性聚合物之溶液(固體成分濃度35質量%)23.7g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)5.0g及ABE-300(新中村化學工業(股)製)2.5g、作為(C)成分的光聚合起始劑之IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.25g及OMNIRAD(註冊商標)184(IGM Resins公司製)[舊
IRGACURE(註冊商標)184(BASFJapan(股)製)]0.75g,以及作為界面活性劑的DFX-18(Neos(股)製)0.0050g,溶解於丙二醇單甲基醚1.2g及丙二醇單甲基醚乙酸酯16.6g而作成溶液。其後,使用孔徑1μm的聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。
[比較例1]
將在合成例1所得的(A)成分之鹼可溶性聚合物的溶液(固體成分濃度35質量%)20.8g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)2.9g及ABE-300(新中村化學工業(股)製)2.2g、作為(C)成分的光聚合起始劑之IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.22g及OMNIRAD(註冊商標)184(IGM Resins公司製)[舊
IRGACURE(註冊商標)184(BASFJapan(股)製)]0.65g,以及作為界面活性劑的DFX-18(Neos(股)製)0.0040g,溶解於丙二醇單甲基醚4.9g及丙二醇單甲基醚乙酸酯18.4g而作成溶液。其後,使用孔徑1μm的聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。本比較例之負型感光性樹脂組成物中(B)成分的含有量在本發明之範圍外。
[比較例2]
將在合成例1所得的(A)成分之鹼可溶性聚合物的溶液(固體成分濃度35質量%)15.6g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)3.3g及ABE-300(新中村化學工業(股)製)3.3g、作為(C)成分的光聚合起始劑之
IRGACURE(註冊商標)OXE01(BASFJapan(股)製)1.3g,以及作為界面活性劑的DFX-18(Neos(股)製)0.0040g,溶解於丙二醇單甲基醚8.3g及丙二醇單甲基醚乙酸酯18.5g而作成溶液。其後,使用孔徑1μm的聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。本比較例的負型感光性樹脂組成物中(B)成分的含有量在本發明之範圍外。
[比較例3]
將在合成例1所得之(A)成分的鹼可溶性聚合物之溶液(固體成分濃度35質量%)24.5g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)4.3g、作為(C)成分的光聚合起始劑之IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.13g,及作為界面活性劑的DFX-18(Neos(股)製) 0.0039g,溶解於丙二醇單甲基醚2.6g及丙二醇單甲基醚乙酸酯18.5g後作成溶液。其後,使用孔徑1μm的聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。本比較例的負型感光性樹脂組成物中(B)成分的含有量為本發明之範圍外,且該(B)成分未含有於1分子中具有2個聚合性基之交聯性化合物。
[比較例4]
將在合成例1所得之(A)成分的鹼可溶性聚合物之溶液(固體成分濃度35質量%)23.2g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)4.1g、作為(C)成分的光聚合起始劑之IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.8g,及作為界面活性劑的DFX-18(Neos(股)製) 0.0039g,溶解於丙二醇單甲基醚3.4g及丙二醇單甲基醚乙酸酯18.5g而作成溶液。其後,使用孔徑1μm的聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。本比較例的負型感光性樹脂組成物中(B)成分的含有量為本發明之範圍外,且該(B)成分未含有於1分子中具有2個聚合性基之交聯性化合物。
[比較例5]
將在合成例1所得之(A)成分的鹼可溶性聚合物之溶液(固體成分濃度35質量%)19.5g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)4.1g及ABE-300(新中村化學工業(股)製)2.0g、作為(C)成分的光聚合起始劑之IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.061g,以及作為界面活性劑的DFX-18(Neos(股)製)0.0039g,溶解於丙二醇單甲基醚5.9g及丙二醇單甲基醚乙酸酯18.5g而作成溶液。其後,使用孔徑1μm的聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。本比較例的負型感光性樹脂組成物為,(C)成分的含有量在本發明之範圍外。
[比較例6]
將在合成例1所得之(A)成分的鹼可溶性聚合物之溶液(固體成分濃度35質量%)17.1g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)3.6g及ABE-300(新中村化學工業(股)製)1.8g、作為(C)成分的光聚合起始劑之
IRGACURE(註冊商標)OXE01(BASFJapan(股)製)1.6g,以及作為界面活性劑的DFX-18(Neos(股)製)0.0039g,溶解於丙二醇單甲基醚7.4g及丙二醇單甲基醚乙酸酯18.5g而作成溶液。其後,使用孔徑1μm的聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。本比較例的負型感光性樹脂組成物為,(C)成分的含有量在本發明之範圍外。
[比較例7]
將在合成例2所得之(A)成分的鹼可溶性聚合物之溶液(固體成分濃度35質量%)24.9g、作為(B)成分的交聯性化合物之PET-30(日本化藥(股)製)5.3g、作為(C)成分的光聚合起始劑之IRGACURE(註冊商標)OXE01(BASFJapan(股)製)0.26g及OMNIRAD(註冊商標)184(IGM Resins公司製) [舊IRGACURE(註冊商標)184(BASFJapan(股)製)]0.78g,以及作為界面活性劑的DFX-18(Neos(股)製)0.0045g,溶解於丙二醇單甲基醚1.3g及丙二醇單甲基醚乙酸酯17.5g而作成溶液。其後,使用孔徑1μm的聚乙烯製微濾器進行過濾後調製出負型感光性樹脂組成物。本比較例的負型感光性樹脂組成物中(B)成分的含有量為本發明之範圍外,且該(B)成分未含有於1分子中具有2個聚合性基之交聯性化合物。
[透過率測定]
將在實施例1至實施例4及比較例1至比較例7所調製的各負型感光性樹脂組成物,於石英基板上使用旋轉塗布機進行塗布,對於加熱板上以100℃進行90秒的預烘烤後,形成如表1所示膜厚的樹脂膜。其次,藉由紫外線照射裝置PLA-501(F)(Canon(股)製),將於365nm中之照射量為1000mJ/cm2
的紫外線對前述樹脂膜全面進行照射。此後,將前述樹脂膜對於加熱板上以100℃進行5分鐘後烘烤。進一步藉由分批式UV照射裝置(高壓水銀燈2kW×1燈)(Eye graphics(股)製),將在365nm中之曝光量為1000mJ/cm2
的紫外線對前述樹脂膜全面進行照射後,於前述石英基板上形成硬化膜。前述預烘烤及後烘烤皆於大氣中實施。對於此等硬化膜,使用紫外線可視分光光度計UV-2550((股)島津製作所製),在波長400nm至800nm的範圍下以2nm之間隔單位變化波長而測定透過率。在波長400nm至800nm之範圍所測定的最低透過率之值如表2所示。該數值越接近100%時,表示越可得到透明的膜。
[耐溶劑性試驗]
將在實施例1至實施例4及比較例1至比較例7所調製的各負型感光性樹脂組成物,於矽晶圓上使用旋轉塗布機進行塗布,對於加熱板上以100℃進行90秒預烘烤後,形成如表1所示膜厚的樹脂膜。其次,藉由紫外線照射裝置PLA-501(F)(Canon(股)製),將於365nm中之照射量為1000mJ/cm2
的紫外線對前述樹脂膜全面進行照射。其後,將前述樹脂膜,作為鹼性顯像液使用表1所示濃度的氫氧化四甲基銨(TMAH)水溶液進行60秒顯像,以超純水進行20秒輕洗(rinse)並乾燥。其結果,在比較例3及比較例5所調製的負型感光性樹脂組成物所形成的樹脂膜,由前述矽晶圓上除去。且,將殘留的樹脂膜對於加熱板上以100℃進行5分鐘後烘烤。最後,藉由分批式UV照射裝置(高壓水銀燈2kW×1燈)(Eye graphics(股)製),將在365nm中之曝光量為1000mJ/cm2
的紫外線對前述樹脂膜全面進行照射後,於前述矽晶圓上形成硬化膜。前述預烘烤及後烘烤皆在大氣中實施。對於此等硬化膜,對各丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、乳酸乙酯、3-甲氧基丙酸甲酯,及2.38質量%濃度之氫氧化四甲基銨(TMAH)水溶液,在23℃之溫度條件下進行含浸2分鐘之試驗。對於浸漬前後測定前述硬化膜之膜厚變化。使用於浸漬試驗的上述溶劑中即使任一種對於浸漬前之該硬化膜的膜厚,若顯示10%以上的膜厚增減時評估為“×”,若為未達10%且5%以上之膜厚增減時評估為“△”,對於所有溶劑的膜厚增減皆未達5%者則評估為“○”,無法測定者則以“-”表示,藉此評估耐溶劑性。評估結果如表2所示。
[殘膜率、感度及殘渣評估]
將在實施例1至實施例4及比較例1至比較例7所調製的各負型感光性樹脂組成物,於矽晶圓上使用旋轉塗布機進行塗布,對於加熱板上以100℃進行90秒預烘烤後,形成如表1所示的膜厚之樹脂膜。前述預烘烤於大氣中實施。使用光干涉式膜厚測定裝置Lambda AceVM-2110(
SCREENSemiconductor Solutions(股)製),測定此等樹脂膜之膜厚。其此,藉由i線StepperNSR-2205i12D(NA=0.63) ((股)Nikon製),隔著二元光罩將前述樹脂膜進行曝光。其後,將前述樹脂膜,使用作為鹼性顯像液之如表1所示的濃度之氫氧化四甲基銨(TMAH)水溶液進行60秒顯像,以超純水進行20秒輕洗(rinse)並乾燥。其結果自由在實施例1至實施例4、比較例1、比較例2、比較例4、比較例6及比較例7所調製的負型感光性樹脂組成物而形成的樹脂膜,7mm×7mm之矩形圖型形成於前述矽晶圓上。另一方面,自由在比較例3及比較例5所調製的負型感光性樹脂組成物所形成的樹脂膜,未形成前述矩形圖型。對於前述矽晶圓上之形成物,以與前述樹脂膜之膜厚測定的同樣方法測定膜厚。比較預烘烤直後之樹脂膜的膜厚,評估殘膜率(%)。其結果如表2所示。殘膜率係由式(顯像後膜厚/預烘烤後膜厚)×100而計算出,該數值越接近100%,表示前述樹脂膜之曝光部越不容易溶解於顯像液故較佳。
且,評估殘膜率成為最大時的最低曝光量。其結果如表2所示。即使曝光量為800mJ/cm2
以上,殘膜率並未能成為最大時,或無法形成7mm×7mm之矩形圖型時,記載為測定不能之“-”。最低曝光量越小,表示前述樹脂膜顯示越高感度。
且使用光干涉式膜厚測定裝置Lambda
AceVM-2110((股)SCREENSemiconductor Solutions製),測定前述樹脂膜之未曝光部的膜厚。前述膜厚越薄,表示殘渣越少。該膜厚若為10nm以上時則評估為“×”,若未達10nm且5nm以上時評估為“△”,未達5nm時評估為“○”,對殘渣進行評估。評估結果如表2所示。
Claims (3)
- 一種負型感光性樹脂組成物,其係使用於微鏡形成者,其特徵為含有下述(A)成分、(B)成分、(C)成分,及溶劑者;對於該(A)成分100質量%而言為80質量%至90質量%的下述(B)成分,對於該(B)成分之總量100質量%而言為3質量%至20質量%的下述(C)成分;(A):具有選自由下述式(1a)、式(1b)、式(1c)、式(1d)及式(1e)所成群的結構單位,或進一步具有與前述結構單位相異的選自由下述式(2a)、式(2b)及式(2c)所成群的結構單位之共聚物的鹼可溶性聚合物(B):聚合性基的數相異的2種交聯性化合物之組合,前述交聯性化合物為,於1分子中具有3個以上作為聚合性基的丙烯醯基氧基或甲基丙烯醯基氧基者(C):至少1種的光聚合起始劑,
- 一種微鏡之製作方法,其特徵為具有:將如請求項1之負型感光性樹脂組成物塗布於基板上,經預烘烤後形成樹脂膜的步驟、通過光罩使前述樹脂膜進行曝光的步驟、將前述曝光後的樹脂膜使用鹼性顯像液進行顯像的步驟,及使前述顯像後的樹脂膜之全面進行曝光的步驟。
- 如請求項2之製作方法,於將前述顯像後的樹脂膜之全面進行曝光的步驟之後或該步驟之前,進一步具有使該樹脂膜進行後烘烤的步驟。
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