TWI662370B - 與外塗佈光致抗蝕劑一起使用之塗料組合物 - Google Patents
與外塗佈光致抗蝕劑一起使用之塗料組合物 Download PDFInfo
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- TWI662370B TWI662370B TW105136436A TW105136436A TWI662370B TW I662370 B TWI662370 B TW I662370B TW 105136436 A TW105136436 A TW 105136436A TW 105136436 A TW105136436 A TW 105136436A TW I662370 B TWI662370 B TW I662370B
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 102
- 239000008199 coating composition Substances 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 125000003118 aryl group Chemical group 0.000 claims abstract description 61
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 27
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 150000001412 amines Chemical group 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 20
- 150000003573 thiols Chemical class 0.000 claims abstract 4
- 229920005989 resin Polymers 0.000 claims description 65
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- 230000005855 radiation Effects 0.000 claims description 21
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- 239000002253 acid Substances 0.000 description 40
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- 125000000217 alkyl group Chemical group 0.000 description 28
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- -1 monocyclic aromatic hydrocarbons Chemical class 0.000 description 22
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- 230000000052 comparative effect Effects 0.000 description 4
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- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
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- 230000000379 polymerizing effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/201—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 an oblique exposure; characterised by the use of plural sources; characterised by the rotation of the optical device; characterised by a relative movement of the optical device, the light source, the sensitive system or the mask
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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
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
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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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
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Abstract
在一個較佳態樣中,提供有機塗料組合物,尤其與外塗佈光致抗蝕劑一起使用之抗反射塗料組合物,所述組合物包括1)一或多個縮水甘油基;及2)一或多個芳族基,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基。亦提供含兒茶酚聚合物及其製備方法。
Description
本發明係關於組合物,且具體而言係關於用於微電子應用之抗反射塗料組合物。在一個較佳之態樣中,本發明之組合物包括1)一或多個縮水甘油基;及2)一或多個芳族基,芳族基各自包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基。本發明之較佳組合物與外塗佈光致抗蝕劑組合物一起使用且可稱為底部抗反射組合物或「BARC」。
光致抗蝕劑為用於將影像轉印至基板之感光膜。在基板上形成光致抗蝕劑塗層且隨後經由光罩使光致抗蝕劑層曝光於活化輻射源。在曝光之後,光致抗蝕劑經顯影,以提供允許選擇性處理基板之浮雕影像。
用於曝光光致抗蝕劑之活化輻射之反射通常對光致抗蝕劑層中圖案化之影像之解析度造成限制。來自基板/光致抗蝕劑界面之輻射之反射可產生光致抗蝕劑中之輻射強度之空間變化,導致顯影時之非均一光致抗蝕劑線寬。輻射亦可自基板/光致抗蝕劑界面散射至光致抗蝕劑之不預期曝光之區域中,再次導致線寬變化。
用於減少反射輻射問題之一種方法已為使用在
基板表面及光致抗蝕劑塗層之間插入之輻射吸收層(抗反射組合物層)。參見美國專利8338078;69270152;5677112;8481247;8012670;6818381;及7846638;WO067329A1以及EP2000852。
SiO2、TiN及其他金屬為在其上塗佈有光致抗蝕劑及抗反射組合物之常見基板。氮氧化矽(SiON)層及其他無機物如Si3N4塗層已用於半導體器件製造,例如作為蝕刻終止層及無機抗反射層。參見美國專利6,124,217;6,153,504以及6,245,682。
具有光致抗蝕劑浮雕影像之圖案轉印經常較佳乾式蝕刻。然而,在乾式蝕刻方法中使用之電漿可對薄氧化物層及氮化物層(如可用於快閃記憶體製造)引起損傷。因此,由於濕式蝕刻方法之相對更溫和條件,濕式蝕刻通常用於此類更易碎基板之圖案轉印。
已使用氫氧化銨及過氧化氫之水性混合物或酸如硫酸及過氧化物如過氧化氫之混合物進行對金屬氮化物(如氮化鈦(TiN)之濕式蝕刻。參見例如US 2006/0226122。
此類使用習知濕式蝕刻劑之問題為其缺乏選擇性。此等些濕式蝕刻劑通常侵蝕周圍結構,導致蝕刻或特定言之在一些光致抗蝕劑之情況下溶脹及/或喪失對光致抗蝕劑塗覆至其上之基板之黏附。隨著臨界尺寸持續減小,此類缺乏選擇性變得越來越無法接受。
因此,將期望具有與外塗佈光致抗蝕劑一起使用之新穎抗反射組合物。將特別期望具有展現增強之效能且可提供圖案化至外塗佈光致抗蝕劑中之影像之增加解析度之新
穎抗反射組合物。亦將期望具有用於塗覆至金屬基板表面上且將提供包含經由濕式蝕刻方法之良好解析度及金屬基板黏附性之新穎抗反射組合物。
現在提供可與外塗佈光致抗蝕劑組合物一起使用之新穎塗料組合物。在較佳態樣中,本發明之塗料組合物可充當外塗佈抗蝕劑層之有效抗反射層。
在較佳之實施例中,提供有機塗料組合物,尤其與外塗佈光致抗蝕劑一起使用之抗反射組合物,其可展現出對底層金屬基板表面(如包括SiO2或TiN之基板表面)之增強黏附性。在較佳態樣中,此類增強之黏附性可經由對底層金屬層如SiO2或TiN之濕式蝕刻處理或對覆蓋金屬層(如金屬層包括氧化物或氮化物,例如SiO2或TiN)之塗層之濕式蝕刻而展現。
已發現本發明之底層塗料組合物可提供出人意料地良好微影效能,包含在濕式蝕刻過程期間。此外,本發明之底層塗料組合物可包含在整個顯影後濕式蝕刻過程中提供對金屬基板(如SiO2或TiN基板表面)之良好黏附。參見,例如在之後之實例中闡述之結果。
在較佳態樣中,提供包括一或多種材料之底層塗料組合物,所述一或多種材料包括1)一或多個縮水甘油基;及2)一或多個芳族基,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基。
在某些態樣中,塗料組合物可包括1)包括一或多個縮水甘油基之第一樹脂及2)包括一或多個芳族基之第二
樹脂,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基。
在其他態樣中,塗料組合物可包括樹脂,所述樹脂包括1)一或多個縮水甘油基及2)一或多個芳族基兩者,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基。
在尤其較佳之態樣中,塗料組合物包括包括芳族基(其包括兒茶酚部分)之材料,例如包括兒茶酚基團如側接基團或樹脂主鏈之重複單元之樹脂。
關於抗反射應用,本發明之底層組合物亦較佳地含有包括發色團之組分,所述發色團可吸收用於曝光外塗佈抗蝕劑層之不期望之輻射,免於反射回抗蝕劑層中。樹脂或其他材料可包括此類發色團基團,如單環芳香烴或稠環芳香烴,例如視情況經取代之苯基、萘基或蒽基。
在另一實施例中,提供新穎含兒茶酚之聚合物。在較佳之態樣中,兒茶酚試劑與預形成之樹脂反應以提供具有側接兒茶酚部分之樹脂。
在與外塗佈光致抗蝕劑一起使用中,塗料組合物可塗覆於基板上,如上面可具有一或多個有機或無機塗層之半導體晶圓。
如所論述,本發明之塗料組合物可特別用於塗覆於氧化物或氮化物基板表面(如SiO2或TiN)上方。
塗覆之塗層可視情況在用光致抗蝕劑層外塗佈之前經熱處理。此類熱處理可引起塗料組合物層之硬化,包含交聯。此類交聯可包含在一或多種組合物組分之間之硬化
及/或共價鍵形成反應,且可調節塗料組合物層之水接觸角。
此後,光致抗蝕劑組合物可塗覆於塗料組合物層上方,接著藉由圖案化活化輻射對塗覆之光致抗蝕劑組合物層成像,且成像之光致抗蝕劑組合物層經顯影以提供光致抗蝕劑浮雕影像。
然後,具有抗蝕劑浮雕影像之基板可經濕式蝕刻,例如用鹼性濕式蝕刻劑如氫氧化銨及過氧化氫之水性混合物處理或用酸性濕式蝕刻劑如硫酸及過氧化氫之水性混合物處理。
多種光致抗蝕劑可與本發明之塗料組合物組合使用(即外塗佈)。與本發明之底層塗料組合物一起使用之較佳光致抗蝕劑為化學增強之抗蝕劑,包含含有一或多種光敏化合物及含有在光生酸存在下經受去封端或斷裂反應之單元之樹脂組分的光致抗蝕劑。
在較佳態樣中,光致抗蝕劑組合物經設計用於負型抗蝕劑,其中曝光區域在顯影過程之後保留,但正型顯影亦可用於移除光致抗蝕劑層之曝光部分。
本發明進一步提供形成光致抗蝕劑浮雕影像之方法及包括塗佈有單獨或與光致抗蝕劑組合物組合之本發明之塗料組合物的基板(如微電子晶圓基板)之新穎製品。
本發明亦包含包括對藉由外塗佈光致抗蝕劑浮雕影像裸露之基板區域濕式蝕刻之方法。
本發明之其他態樣揭示於下文中。
塗料組合物
如上文所論述,在較佳態樣中,提供有機塗料組合物,尤其與外塗佈光致抗蝕劑一起使用之抗反射組合物,所述組合物包括一或多種材料,所述一或多種材料包括1)一或多個縮水甘油基;及2)一或多個芳族基,各芳族基包括兩個或更多個包括羥基(-OH)、硫醇(S<)及/或胺(-N<)部分之取代基。應理解,此類羥基、硫基或胺基可具有直接鍵聯至芳環原子(例如芳環之碳原子)之O、S或N原子,或者一或多個除O、S或N之外之原子可插入在各別之羥基、硫基或胺部分及芳環之O、S或N原子之間。
較佳之芳族基取代基包含具有一或多個O、S及/或N原子之部分,尤其包括羥基、胺或硫基部分之部分。在某些態樣中,較佳為其中雜(O、S或N)原子直接鍵聯至芳環之部分,例如選自-OH、-SR及-NRR之芳環取代基,其中各R獨立地為氫或非氫取代基(如視情況經取代之C1-20烷基)。在額外態樣中,較佳為其中雜(O、S或N)原子與芳環間隔開之部分,例如藉由一或多個視情況經取代之碳原子,包含視情況經取代之C1-20烷基(包含C1-20伸烷基)、視情況經取代之C1-20雜烷基(包含C1-20雜伸烷基)及雜脂環基(包含C1-20烷氧基)、視情況經取代之C1-20烷硫基以及視情況經取代之C1-20烷基胺。
兩個或更多個含雜取代基可在芳族基上存在於多個位置中之任一處。在某些態樣中,芳族基將具有兩個存在於相鄰環位置處(例如,在苯環中之鄰位關係)之含雜取
代基。在其他態樣中,兩個含雜取代基可藉由在兩個含雜環位置之間插入之最小1、2、3或更多個芳環位置分開。
一般而言,包括縮水甘油基及/或雜-取代之芳族基之較佳材料為樹脂。舉例而言,如上文所論述,較佳之塗料組合物可包括1)包括一或多個縮水甘油基之第一樹脂及2)包括一或多個芳族基之第二樹脂,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基。另外較佳之塗料組合物可包括樹脂,所述樹脂包括1)一或多個縮水甘油基及2)一或多個芳族基兩者,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基。
合適之縮水甘油基可例如藉由使單體聚合而提供,所述單體包括縮水甘油基部分,如由以下例示之丙烯酸酯化合物:
其中在上面結構中,n為1至20之合適正整數,更通常為1至8,且R為氫或非氫取代基,如視情況經取代之C1-20烷基。
包括多個含雜(N、O、S)取代基之合適芳族基亦可例如藉由使單體聚合而提供,所述單體包括合適之雜(N、O、S)-取代之芳族基(例如苯基),如以下例示之丙烯酸酯化合物:
其中在上面結構中,n為正整數,如1至20,更通常為1至8。
合適之發色團可例如藉由使單聚合體而提供於樹脂中,所述單體包括合適之發色團部分,如單環或或稠環芳族,尤其視情況經取代之苯基、萘基或蒽基,如以下例示之丙烯酸酯化合物:
其中在上面結構中,n為1至20合適之正整數,更通常為1至8。
用於本發明之塗料組合物之樹脂合適地可包括除含縮水甘油基單元及雜-取代之芳族單元以外之另外的單元,如藉由使以下化合物中任一項聚合而提供之單元:
其中在上面結構中,R2合適地為氫或非氫取代基,如視情況經取代之C1-20烷基,包含甲基,且X為碳或雜(O、S或N)原子。
用於本發明之塗料組合物之具體較佳的樹脂包含如下:
1)樹脂,其包括1)縮水甘油基,2)具有多個含雜取代基如羥基之芳族基以及3)如蒽基之發色團,如由以下樹脂例示,其中值x、y及z表示在樹脂中各重複單元之各別莫耳量,且各自可合適獨立地在10莫耳%至80莫耳%範圍內變化。
2)樹脂,其包括1)縮水甘油基,2)如蒽基之發色團以及3)不同於具有多個含雜環取代基之芳族基之視情況選用的第三單元,如由以下樹脂例示,其中在第一樹脂中,單獨樹脂主鏈之值x、y及z表示在樹脂中各重複單元之各別之莫耳量,且x及z可各自合適獨立地在5莫耳%至95莫耳%範圍內變化且x可在0至80莫耳%範圍內變化。在下面即將示出之第一樹脂中,在中間單元及來自主鏈之側基中示出之基團X可為多種基團,包含視情況經取代之C1-20烷基,視情況經取代之碳環芳基以及視情況經取代之雜芳基。
3)樹脂,其包括1)縮水甘油基,2)具有多個含雜環取代基之芳族基以及3)視情況選用之第三單元,如由以下樹脂例示,其中在第一樹脂中,單獨樹脂主鏈之值x、y及z表示在樹脂中各重複單元之各別莫耳量,且x及z可各自合適獨立地在5莫耳%至95莫耳%範圍內變化,且x可在0至80莫耳%範圍內變化。在下面即將示出之第一樹脂中,在中間單元及來自主鏈之側基中示出之基團X可為多種基團,包含視情況經取代之C1-20烷基,視情況經取代之碳環芳基以及視情況經取代之雜芳基。
在上面剛剛之三種樹脂結構中,各合適n可合適地為1至20之正整數,更通常為1至8之整數,且R為氫或非氫取代基,如視情況經取代之C1-20烷基。
4)樹脂(包含均聚物或共聚物),其包括具有除具有多個含雜環取代基之芳族基外之單元,如以下示例性1)兒茶酚化之酚醛清漆;及2)基於丙烯酸酯之樹脂:
5)包括縮水甘油基之樹脂(包含均聚物或共聚物),如以下基於丙烯酸酯之樹脂:
如上文所論述,在又一實施例中,提供新穎含兒茶酚聚合物。在較佳之態樣中,兒茶酚試劑與預形成之樹脂
反應以提供具有側接兒茶酚部分之樹脂。舉例而言,兒茶酚試劑,如具有如酸或胺基之另外反應性取代基之二羥苯化合物可與具有反應性基團如環氧基之聚合物反應。
因此,舉例而言,如以下方案1中所例示,具有反應性基團之聚合物如具有縮水甘油基部分之所描繪之丙烯酸酯樹脂與包括一或多個可與聚合物反應之部分之兒茶酚試劑反應,以提供具有側接兒茶酚基團之聚合物反應產物。
如一般在以下方案2中例示之具體較佳之系統包含兒茶酚試劑與反應性聚合物如包括環氧基之樹脂之反應以提供聚合物反應產物,所述聚合物反應產物包括1)側接兒茶酚部分及2)反應性部分,如可參與含有聚合物反應產物之塗層之交聯之羥基、視情況經取代之胺或羧基。
如本文中所提及,合適之雜烷基包含視情況經取代之C1-20烷氧基、較佳地具有1至約20個碳原子之視情況
經取代之烷硫基;較佳地1至約20個碳原子之視情況經取代之烷基伸磺醯基;較佳地具有1至約20個碳原子之視情況經取代之烷基磺醯基;及較佳地具有1至約20個碳原子之視情況經取代之烷基胺。
亦應理解,除非另外指明,否則術語「雜烷基」均包含「雜脂環」基。雜脂環基為具有一或多個雜(例如N、O或S)環原子之非芳環基團。較佳之雜脂環基具有5至20個環原子以及1、2或3個N、O或S環原子。
術語「烷基」係指飽和脂族基之基團,包含直鏈烷基基團、支鏈烷基基團、環烷基(脂環族)基團、烷基取代之環烷基基團及環烷基取代之烷基基團。在較佳態樣中,直鏈或支鏈烷基在其主鏈中具有30個或更少之碳原子(例如對非環狀C1-C30,對支鏈C3-C30),較佳26個或更少,且更佳20個或更少以及更佳4個或更少。
亦應理解,除非另外指明,否則術語「烷基」均包含「碳脂環」基。
如本文中所提及,術語「碳脂環基」意指非芳族基之各環成員均為碳。碳脂環基可具有一或多個內環碳-碳雙鍵,其限制條件為所述環不為芳族環。術語視情況經取代之「環烷基」意指非芳族基之各環成員均為碳,且碳環不具有任何內環碳-碳雙鍵。舉例而言,環己基、環戊基及金剛烷基均為環烷基以及碳脂環基。碳脂環基及環烷基可包括一個環或多個(例如2、3、4個或更多個)橋聯、稠合或以其他方式共價鍵聯之環。
如本文中所提及,「雜芳基」基團包含芳族5員
至8員單環、8員至12員雙環或11員至14員三環環系統,若為單環,則所述環系統具有1至3個雜原子,若為雙環則具有1至6個雜原子或者若為三環則具有1至9個雜原子,所述雜原子選自O、N或S(例如,碳原子及若為單環、雙環或三環則分別為1至3個、1至6個或1至9個N、O或S之雜原子),其中各環之0、1、2、3或4個原子可經取代基取代。雜芳基之實例包含吡啶基、呋喃基(furyl/furanyl)、咪唑基、苯并咪唑基、嘧啶基、苯硫基或噻吩基、喹啉基、吲哚基、噻唑基及其類似基團。
為「視情況經取代之」各種材料及取代基(包含以上式(I)及式(II)之基團R、R1及R2)可在一或多個可用位置處由例如鹵素(F、Cl、Br、I);硝基;羥基;胺基;烷基如C1-8烷基;烯基如C2-8烯基;烷基胺基如C1-8烷基胺基;碳環芳基如苯基、萘基、蒽基;雜芳基及其類似基團經合適地取代。
多種樹脂可用作底層塗料組合物之樹脂組分。
本發明之塗料組合物之特別較佳之樹脂可包括聚酯鍵。聚酯樹脂可藉由一或多種多元醇試劑與一或多種含羧基(如羧酸、酯、酸酐等)化合物之反應容易地製備。合適之多元醇試劑包含二醇、甘油及三醇,如二醇,如二醇為乙二醇、1,2-丙二醇、1,3-丙二醇、丁二醇、戊二醇、環丁基二醇、環戊基二醇、環己基二醇、二羥甲基環己烷,及三醇如甘油、三羥甲基乙烷、三羥甲基丙烷及其類似物質。
用於本發明之抗反射組合物之較佳聚酯樹脂亦揭示於U.S.8,501,383;U.S.2011/0033801以及U.S.7,163,751
中。如彼等專利文獻中所揭示,含有酯重複單元(聚酯)之樹脂可合適地藉由含羧基化合物(如羧酸、酯、酸酐等)與含羥基化合物,較佳地具有多個羥基之化合物,如二醇,例如乙二醇或丙二醇,或甘油,或其他二醇、三醇、四醇及其類似物質之聚合來提供。在某些態樣中,較佳地,酯官能基以聚合物主鏈之組分或聚合物主鏈內之組分形式,而非以側接或側鏈單元形式存在。酯部分亦可以側基形式存在,但較佳地,聚合物亦含有沿聚合物主鏈之酯官能基。亦較佳地,其中酯重複單元包括芳族取代基,如視情況經取代之碳環芳基,例如視情況經取代之苯基、萘基或蒽基取代基,作為側鏈或更佳地沿著聚合物主鏈。
基於丙烯酸酯(包含基於甲基丙烯酸酯)之樹脂亦為較佳的。
本發明之塗料組合物之樹脂可包括多種額外基團,如氰尿酸酯基,如美國專利6852421及8501383中所揭示。
如所論述,對於抗反射應用,合適地經反應以形成樹脂之化合物中之一或多者包括可充當發色團以吸收用於曝光外塗佈光致抗蝕劑塗層之輻射之部分。
另外,用於抗反射目的之底層塗料組合物可含有含有與提供水接觸角調變之樹脂組分(例如含有光酸不穩定基團及/或鹼反應性基團之樹脂)分離之發色團單元之材料。舉例而言,塗料組合物可包括含有苯基、蒽、萘基等單元之聚合或非聚合化合物。
可容易地製備包括一或多個縮水甘油基部分及/
或具有多個含雜取代基之芳族基之樹脂。舉例而言,可聚合含有所期望基團之單體。較佳之合成闡述於以下實例中。
較佳地,本發明之底層塗料組合物之樹脂將具有約1,000至約10,000,000道爾頓,更通常約2,000至約10,000道爾頓之重量平均分子量(Mw)及約500至約1,000,000道爾頓之數量平均分子量(Mn)。本發明組合物之樹脂之分子量(Mw或Mn)藉由凝膠滲透層析法合適地測定。
樹脂組分將為許多較佳實施例中之底層塗料組合物之主要固體組分。舉例而言,一或多種樹脂可合適地以按塗料組合物之總固體含量計之50重量%至99.9重量%,更通常地以按塗料組合物之總固體含量計之80重量%或85重量%至95重量%、98重量%或99+(或甚至100)重量%存在。如本文中所提及,塗料組合物之固體係指除溶劑載體以外之塗料組合物之所有材料。
在某些實施例中,除樹脂或具有縮水甘油基之其他材料以外,本發明之塗料組合物可包括交聯劑。舉例而言,塗料組合物可包含基於胺之交聯劑,如三聚氰胺材料,包含三聚氰胺樹脂,如由氰特工業(Cytec Industries)製造且以Cymel 300、301、303、350、370、380、1116及1130之商品名市售;甘脲,包含購自氰特工業(Cytec Industries)之彼等甘脲;及基於苯并三聚氰胺及脲之材料,包含樹脂,如以名稱Cymel 1123及1125購自氰特工業(Cytec Industries)之苯并三聚氰胺樹脂及以Powderlink 1174及1196之名稱購自氰特工業(Cytec Industries)之脲樹脂。除可商購以外,此類基於胺之樹脂可例如藉由丙烯醯胺或甲基丙烯醯胺共聚物與甲
醛在含醇溶液中之反應,或者藉由N-烷氧基甲基丙烯醯胺或甲基丙烯醯胺與其他適合單體之共聚來製備。
含有本發明之塗料組合物之縮水甘油基及/或具有多個含雜取代基之芳族基之樹脂一般以塗料組合物之總固體(除溶劑載體之外之所有組分)之約5重量%與100重量%之間,更通常以塗料組合物之總固體(除溶劑載體之外之所有組分)之至少約20重量%、30重量%、40重量%、50重量%、60重量%、70重量%、80重量%、90重量%或100重量%之量存在。
若塗料組合物含有1)包括縮水甘油基之第一聚合物及2)包括具有多個羥基、硫醇基及/或胺基之芳族基之第二聚合物(不同於第一聚合物),則各此類聚合物合適地以塗料組合物之總固體(除溶劑載體之外之所有組分)之約5重量%與95重量%之間,更通常以塗料組合物之總固體(除溶劑載體之外之所有組分)之至少約10重量%、20重量%、30重量%、40重量%、50重量%、60重量%、70重量%、80重量%或90重量%之量存在。
較佳之本發明之塗料組合物亦可含有熱酸產生劑化合物。藉由熱酸產生劑之活化之塗料組合物的熱誘導交聯一般為較佳的。
用於塗料組合物之合適之熱酸產生劑化合物包含離子或大體上中性之熱酸產生劑,例如芳烴磺酸銨鹽(例如甲苯磺酸銨鹽),用於在抗反射組合物塗層之固化期間催化或促進交聯。通常,一或多種熱酸產生劑以組合物之總乾燥組分(除溶劑載體之外之所有組分)之約0.1重量%至10重
量%,更佳地以總乾燥組分之約0.5重量%至2重量%之濃度存在於塗料組合物中。
本發明之塗料組合物(特定言之用於反射控制應用)亦可含有吸收用於曝光外塗佈光致抗蝕劑層之輻射之額外染料化合物。其他視情況選用之添加劑包含表面調平劑,例如可以商品名Silwet 7604商購之調平劑,或購自3M公司(3M Company)之界面活性劑FC 171或FC 431。
本發明之底層塗料組合物亦可含有其他材料,如光酸產生劑,包含與外塗佈光致抗蝕劑組合物一起使用之如所論述之光酸產生劑。關於光酸產生劑在抗反射組合物中之此類用途之論述,參見美國專利6261743。
為製備本發明之液體塗料組合物,塗料組合物之組分溶解於合適溶劑中,例如,一或多種氧基異丁酸酯,尤其2-羥基異丁酸甲酯、乳酸乙酯或如2-甲氧基乙醚(二乙二醇二甲醚)、乙二醇單甲醚及丙二醇單甲醚之二醇醚中之一或多者;具有醚及羥基部分兩者之溶劑,如甲氧基丁醇、乙氧基丁醇、甲氧基丙醇及乙氧基丙醇;2-羥基異丁酸甲酯;酯,如溶纖劑乙酸甲酯、溶纖劑乙酸乙酯、丙二醇單甲醚乙酸酯、二丙二醇單甲醚乙酸酯及其他溶劑,如二元酯、碳酸伸丙酯及γ-丁內酯。溶劑中之乾式組分之濃度將視若干因素如塗覆方法而定。一般而言,底層塗料組合物之固體含量在塗料組合物之總重量之約0.5重量%至20重量%範圍內變化,較佳地,固體含量在塗料組合物之約0.5重量%至10重量%範圍內變化。
例示性光致抗蝕劑系統
與底層塗料組合物一起使用之光致抗蝕劑通常包括聚合物及一或多種酸產生劑。一般較佳為正型抗蝕劑且抗蝕劑聚合物具有賦予抗蝕劑組合物鹼性水溶性之官能基。舉例而言,較佳為包括極性官能基(如羥基或羧酸酯基)或在微影處理後可釋放此類極性部分之酸不穩定基團之聚合物。較佳地,聚合物以足以使得抗蝕劑可用鹼性水溶液顯影之量用於抗蝕劑組合物中。
酸產生劑亦合適地與包括含有芳族基(如包含酚之視情況經取代之苯基、視情況經取代之萘基及視情況經取代之蒽)之重複單元之聚合物一起使用。含有視情況經取代之苯基(包含苯酚)之聚合物特別合適於許多抗蝕劑系統,包含用EUV及電子束輻射成像之彼等抗蝕劑系統。對於正性作用抗蝕劑,聚合物較佳地亦含有一或多個包括酸不穩定基團之重複單元。舉例而言,在含有視情況經取代之苯基或其他芳族基之聚合物之情況下,聚合物可包括含有一或多個酸不穩定部分之重複單元,如藉由使丙烯酸酯或甲基丙烯酸酯化合物之單體與酸不穩定酯(例如丙烯酸第三丁酯或甲基丙烯酸第三丁酯)聚合而形成之聚合物。此類單體可與一或多種包括(一或多個)芳族基(如,視情況苯基)之其他單體(例如苯乙烯或乙烯基苯酚單體)共聚。
用於形成此類聚合物之較佳單體包含:具有下式(V)之酸不穩定單體、下式(VI)之含內酯單體、用於調節鹼性顯影劑中之溶解速率的下式(VII)之鹼可溶單體及下式(VIII)之生酸單體,或包括前述單體中之至少一者之組合:
其中各Ra獨立地為H、F、-CN、C1-10烷基或C1-10氟烷基。在式(V)之酸可脫保護單體中,Rb獨立地為C1-20烷基、C3-20環烷基、C6-20芳基或C7-20芳烷基,且各Rb為獨立的或至少一個Rb鍵結至相鄰Rb以形成環狀結構。在式(VI)之含內酯單體中,L為單環、多環或稠合多環C4-20含內酯基團。在式(VII)之鹼可溶單體中,W為鹵代或非鹵代、芳族或非芳族C2-50含羥基有機基團,其pKa小於或等於12。在式(VIII)之酸產生單體中,Q為含酯或非含酯的且為氟化或非氟化的,且為C1-20烷基、C3-20環烷基、C6-20芳基或C7-20芳烷基;A為含酯或非含酯的且為氟化或非氟化的,且為C1-20烷基、C3-20環烷基、C6-20芳基或C7-20芳烷基;Z-為陰離子部分,包括羧酸根、磺酸根、磺醯胺陰離子或磺醯亞胺陰離子,且G+為鋶或碘陽離子。
例示性酸可脫保護單體包含但不限於:
或包括至少一種前述單體之組合,其中Ra為H、F、-CN、C1-6烷基或C1-6氟烷基。
合適之內酯單體可為下式(IX)之單體:
其中Ra為H、F、-CN、C1-6烷基或C1-6氟烷基,R為C1-10烷基、環烷基或雜環烷基,且w為0至5之整數。在式(IX)中,R直接連接至內酯環上或通常連接至內酯環及/或一或多個R基團上,且酯部分直接連接或經由R間接連接至內酯環上。
例示性含內酯單體包含:
或包括至少一種前述單體之組合,其中Ra為H、F、-CN、C1-10烷基或C1-10氟烷基。
合適之鹼可溶性單體可為下式(X)之單體:
其中各Ra獨立地為H、F、-CN、C1-10烷基或C1-10氟烷基,A為含羥基或非含羥基、含酯或非含酯、氟化或非氟化之C1-20伸烷基、C3-20伸環烷基、C6-20伸芳基或C7-20伸芳烷基,且x為0至4之整數,其中當x為0時,A為含羥基之C6-20伸芳基。
例示性鹼可溶單體包含具有以下結構之彼等單體:
或包括至少一種前述單體之組合,其中Ra為H、F、-CN、C1-6烷基或C1-6氟烷基。
較佳之酸產生單體包含式(XI)或式(XII)之彼等單體:
其中各Ra獨立地為H、F、-CN、C1-6烷基或C1-6氟烷基,A為經氟取代之C1-30伸烷基、經氟取代之C3-30伸環烷基、經氟取代之C6-30伸芳基或經氟取代之C7-30伸烷基伸芳基,且G+為鋶或碘陽離子。
較佳地,在式(XI)及式(XII)中,A為-[(C(R1)2)xC(=O)O]b-C((R2)2)y(CF2)z-基團或鄰位、間位或對位取代之-C6F4-基團,其中各R1及R2各自獨立地為H、F、-CN、C1-6氟烷基或C1-6烷基,b為0或1,x為1至10之整數,y及z獨立地為0至10之整數,且y+z之總和為至少1。
例示性較佳之酸產生單體包含:
或包括至少一種前述單體之組合,其中各Ra獨立地為H、F、-CN、C1-6烷基或C1-6氟烷基,k合適地為0至5之整數;且G+為鋶或碘陽離子。如在本文各式中所提及之G+可為如本文中所揭示之酸產生劑且包括側氧基-二氧二氧戊環部分及/或側氧基-二噁烷部分。
較佳之酸產生單體可包含鋶或碘陽離子。較佳地,在式(IV)中,G+為式(XIII):
其中X為S或I;各R0為鹵代或非鹵代的且獨立地為C1-30
烷基;多環或單環C3-30環烷基;多環或單環C4-30芳基或包括至少一種前述基團之組合,其中當X為S時,R0基團中之一者視情況藉由單鍵連接至一個相鄰R0基團,且a為2或3,其中當X為I時,a為2,或當X為S時,a為3。
例示性酸產生單體包含具有下式之彼等單體:
尤其適用於本發明之正性作用化學增強光致抗蝕劑中之具有酸不穩定去封端基團之聚合物已揭示於歐洲專利申請案0829766A2(具有縮醛之聚合物及縮酮聚合物)及歐洲專利申請案EP0783136A2(包含1)苯乙烯;2)羥基苯乙烯;以及3)酸不穩定基團(尤其丙烯酸烷酯酸不穩定基團)之單元之三元共聚物及其他共聚物)。
用於在低於200nm,如193nm下成像之光致抗蝕劑中之額外較佳樹脂包括以下通式(I)、(II)及(III)之單元:用於在低於200nm,如193nm下成像之光致抗
蝕劑中之較佳樹脂包括以下通式(I)、(II)及(III)之單元:
其中:R1為(C1-C3)烷基;R2為(C1-C3)伸烷基;L1為內酯基;且n為1或2。
用於本發明光致抗蝕劑中之聚合物之分子量及多分散性可合適地在很寬範圍內變化。合適之聚合物包含Mw為約1,000至約50,000、更通常約2,000至約30,000且分子量分佈為約3或更小、更通常分子量分佈為約2或更小之彼等聚合物。
較佳之本發明負性作用組合物包括在曝光於酸後將固化、交聯或硬化之材料及如本文中所揭示之兩種或更多種酸產生劑之混合物。較佳之負性作用組合物包括聚合物黏合劑(如酚系或非芳族聚合物)、交聯劑組分及本發明之光敏組分。此類組合物及其用途已揭示於Thackeray等人之歐洲專利申請案0164248及美國專利第5,128,232號中。用作聚合物黏合劑組分之較佳酚系聚合物包含酚醛清漆及聚(乙烯基苯酚),如上文所論述之彼等組分。較佳之交聯劑包含基於胺之材料(包含三聚氰胺)、甘脲、基於苯并胍胺之材料以及基於脲之材料。三聚氰胺-甲醛聚合物通常為特別合適的。此類交聯劑為可商購的,例如三聚氰胺聚合物、甘脲聚合物、基於脲之聚合物及苯并胍胺聚合物,如由氰特(Cytec)以商品名稱Cymel 301、303、1170、1171、1172、1123及1125以及
Beetle 60、65及80市售之彼等交聯劑。
特別較佳之本發明之光致抗蝕劑可用於浸沒式微影應用中。關於較佳浸沒式微影光致抗蝕劑及方法之論述,參見例如羅門哈斯電子材料(Rohm and Haas Electronic Materials)之U.S.7968268。
本發明之光致抗蝕劑亦可包括單一酸產生劑或相異酸產生劑之混合物,通常2或3種不同酸產生劑之混合物,更通常由總共2種相異酸產生劑組成之混合物。光致抗蝕劑組合物包括以在曝光於活化輻射後足以在組合物之塗層中產生潛像之量採用之酸產生劑。舉例而言,酸產生劑將合適地以按光致抗蝕劑組合物之總固體計1wt%至20wt%之量存在。
合適之酸產生劑在化學增強光致抗蝕劑領域中已知且包含例如:鎓鹽,例如三氟甲烷磺酸三苯基鋶、三氟甲烷磺酸(對第三丁氧基苯基)二苯基鋶、三氟甲烷磺酸參(對第三丁氧基苯基)鋶、對甲苯磺酸三苯基鋶;硝基苯甲基衍生物,例如2-硝基苯甲基-對甲苯磺酸鹽、2,6-二硝基苯甲基-對甲苯磺酸鹽以及2,4-二硝基苯甲基-對甲苯磺酸鹽;磺酸酯,例如1,2,3-參(甲烷磺醯基氧基)苯、1,2,3-參(三氟甲烷磺醯基氧基)苯以及1,2,3-參(對甲苯磺醯基氧基)苯;重氮甲烷衍生物,例如雙(苯磺醯基)重氮甲烷、雙(對甲苯磺醯基)重氮甲烷;乙二肟衍生物,例如雙-O-(對甲苯磺醯基)-α-二甲基乙二肟及雙-O-(正丁烷磺醯基)-α-二甲基乙二肟;N-羥基醯亞胺化合物之磺酸酯衍生物,例如N-羥基丁二醯亞胺甲磺酸酯、N-羥基丁二醯亞胺三氟甲磺酸酯;以及含鹵素之三嗪化合物,
例如2-(4-甲氧基苯基)-4,6-雙(三氯甲基)-1,3,5-三嗪以及2-(4-甲氧基萘基)-4,6-雙(三氯甲基)-1,3,5-三嗪。
如本文中所提及,酸產生劑可在曝光於活化輻射,如EUV輻射、電子束輻射、193nm波長輻射或其他輻射源時產生酸。如本文中所提及之酸產生劑化合物亦可稱為光酸產生劑化合物。
本發明之光致抗蝕劑亦可含有其他材料。舉例而言,其他視情況選用之添加劑包含光化及造影染料、抗條紋劑、塑化劑、速度促進劑及敏化劑。此類視情況選用之添加劑通常將以較小濃度存在於光致抗蝕劑組合物中。
替代性地或另外,其他添加劑可以包含淬滅劑,其為非光可破壞鹼,如基於氫氧化物、羧酸鹽、胺、亞胺及醯胺之彼等鹼。較佳地,此類淬滅劑包含C1-30有機胺、亞胺或醯胺,或者可為強鹼(例如氫氧化物或醇鹽)或弱鹼(例如羧酸鹽)之C1-30四級銨鹽。例示性淬滅劑包含胺,如三丙胺、十二烷胺、參(2-羥丙基)胺、醇肆(2-羥丙基)乙二胺(oltetrakis(2-hydroxypropyl)ethylenediamine);芳基胺,如二苯胺、三苯胺、胺基苯酚及2-(4-胺基苯基)-2-(4-羥基苯基)丙烷,受阻胺,如二氮雜雙環十一烯(DBU)或二氮雜二環壬烯(DBN),或離子淬滅劑,包含四級烷基銨鹽,如氫氧化四丁銨(TBAH)或乳酸四丁銨。
界面活性劑包含氟化及非氟化之界面活性劑,且較佳地為非離子的。例示性氟化非離子界面活性劑包含全氟C4界面活性劑,如可購自3M公司之FC-4430及FC-4432界面活性劑;及氟二醇,如來自Omnova之POLYFOX PF-636、
PF-6320、PF-656及PF-6520氟界面活性劑。
光致抗蝕劑進一步包含一般適合於溶解、分配及塗佈光致抗蝕劑中所用組分之溶劑。例示性溶劑包含苯甲醚;醇,包含乳酸乙酯、1-甲氧基-2-丙醇及1-乙氧基-2丙醇;酯,包含乙酸正丁酯、乙酸1-甲氧基-2-丙酯、甲氧基乙氧基丙酸酯、乙氧基乙氧基丙酸酯;酮,包含環己酮及2-庚酮;以及包括至少一種前述溶劑之組合。
微影加工
在使用中,本發明之塗料組合物藉由如旋塗之多種方法中之任一者以塗層形式塗覆至基板。塗料組合物一般以約0.02μm與0.5mm之間之乾燥層厚度,較佳地約0.04μm與0.20μm之間之乾燥層厚度塗覆於基板上。基板合適地為用於涉及光致抗蝕劑之方法中之任何基板。舉例而言,基板可為矽、二氧化矽或鋁-氧化鋁微電子晶圓。亦可採用砷化鎵、碳化矽、陶瓷、石英或銅基板。亦合適地採用用於液晶顯示器或其他平板顯示器應用之基板,例如玻璃基板、氧化銦錫塗佈基板及其類似基板。亦可採用用於光學及光電裝置(例如波導)之基板。
較佳地,塗覆之塗層在光致抗蝕劑組合物塗覆於底層塗料組合物上方之前固化。固化條件將隨著底層塗料組合物之組分而變化。特別地,固化溫度將視塗料組合物中採用之特定酸或酸(熱)產生劑而定。典型固化條件為約80℃至225℃下持續約0.5至5分鐘。固化條件較佳地使得塗料組合物塗層基本上不溶於使用之光致抗蝕劑溶劑以及顯影劑溶液。
在此類固化之後,光致抗蝕劑塗覆於塗覆之塗料組合物之表面上。如同底部塗料組合物層之塗覆,外塗佈光致抗蝕劑可藉由任何標準方法,如藉由旋塗、浸塗、彎月面塗佈或輥塗來塗覆。在塗佈後,光致抗蝕劑塗層通常藉由加熱乾燥以移除溶劑,較佳地直至抗蝕劑層無黏性。最優地,應基本上不出現底部組合物層與外塗佈光致抗蝕劑層之互混。
然後抗蝕劑層用活化輻射,如以習知方式穿過遮罩之248nm、193nm或EUV輻射成像。曝光能量足以有效地活化抗蝕劑系統之光敏組分以在抗蝕劑塗層中產生圖案化影像。通常,曝光能量之範圍介於約3mJ/cm2至300mJ/cm2且部分地視採用之曝光工具及特定抗蝕劑及抗蝕劑處理而定。曝光之抗蝕劑層可在必要時經受曝光後烘烤以在塗層之曝光及未曝光區域之間產生或增強溶解性差異。舉例而言,負型酸硬化光致抗蝕劑通常需要曝光後加熱以誘導酸促進之交聯反應,且許多化學增強正性作用抗蝕劑需要曝光後加熱以誘導酸促進之脫除保護反應。通常,曝光後烘烤條件包含約50℃或更高之溫度,更具體地約50℃至約160℃範圍內之溫度。
光致抗蝕劑層亦可曝露於浸沒式微影系統中,即其中在曝光工具(特定言之投影透鏡)及光致抗蝕劑塗佈之基板之間的空間經浸沒流體佔據,如水或與一或多種添加劑如硫酸銫(其可提供折射率增強之流體)混合之水。較佳地,浸沒流體(例如水)已經處理以避免氣泡,例如水可經脫氣以避免奈米氣泡。
本文中提及「浸沒曝露」或其他類似術語指示用插入在曝光工具與經塗佈之光致抗蝕劑組合物層之間之此類流體層(例如水或具有添加劑之水)進行曝光。
然後,曝光之光致抗蝕劑層用能夠選擇性地移除膜之一部分以形成光致抗蝕劑圖案之合適顯影劑處理。在負型顯影方法中,光致抗蝕劑層之未曝光區域可藉由用合適之非極性溶劑處理來選擇性地移除。關於負型顯影之適合程序,參見U.S.2011/0294069。用於負型顯影之典型非極性溶劑為有機顯影劑,如選自酮、酯、烴及其混合物之溶劑,例如丙酮、2-己酮、2-庚酮、乙酸甲酯、乙酸丁酯及四氫呋喃。用於NTD方法中之光致抗蝕劑材料較佳地形成可與有機溶劑顯影劑形成負像或與如四烷基氫氧化銨溶液之水性鹼顯影劑形成正像之光致抗蝕劑層。較佳地,NTD光致抗蝕劑基於具有酸敏(可脫保護)基團之聚合物,所述基團在脫除保護基時形成羧酸基及/或羥基。
可替代地,曝光之光致抗蝕劑層之顯影可藉由用能夠選擇性地移除膜之曝光部分(其中光致抗蝕劑為正型)或移除膜之未曝光部分(其中光致抗蝕劑在曝光區域中可交聯,即為負型)之合適顯影劑處理曝光層來實現。較佳地,光致抗蝕劑為正型的,其基於具有在脫除保護基時形成羧酸基之酸敏(可脫保護)基團之聚合物,且顯影劑較佳地為金屬離子自由四烷基氫氧化銨溶液,例如0.26N四甲基氫氧化銨水溶液。圖案藉由顯影形成。
然後,顯影之基板可根據本領域中眾所周知之程序在缺乏光致抗蝕劑之彼等基板區域,例如缺乏光致抗蝕劑
之化學蝕刻或鍍敷區域上選擇性地處理。合適之蝕刻劑包含氫氟酸蝕刻溶液及電漿氣體蝕刻劑,如氧電漿蝕刻劑。電漿氣體蝕刻劑移除底層塗層。
如所論述,在某些態樣中,可合適地採用濕式蝕刻製程。藉由將用濕式蝕刻組合物蝕刻之表面(例如金屬氮化物或塗覆有一或多種有機及/或無機層之金屬氮化物)曝光一段時間及在有效蝕刻表面(例如金屬氮化物表面及/或在其上之塗層)之溫度下可合適地進行濕式蝕刻。例示性濕式蝕刻組合物包含氫氧化銨及過氧化物如過氧化氫之水性混合物,或酸如硫酸及過氧化物如過氧化氫之混合物。關於例示性組合物,參見US 2006/0226122。以下實例亦提供例示性濕式蝕刻製程條件。如本文中所提及,「濕式蝕刻製程」意指用流體組合物,通常為酸或鹼與過氧化劑組合來處理由鄰接光致抗蝕劑(在顯影光致抗蝕劑影像之後)限定之基板區域,但是在任何情況下區別於電漿乾式蝕刻。
以下非限制性實例說明本發明。
一般說明
以下聚合物P1至聚合物P9描述以下實例中。聚合物P3購自日本尼索(Nisso),MW=5.3K,PDI=1.1。聚合物P4、P5、P6及P7由韓國美源化學(Miwon Chemical)提供。
實例1-4:聚合物合成
實例1:合成THEIC-TCEIC共聚物P1
將THEIC(參(2-羥乙基)異氰尿酸酯)(30.43g,116.5mmol)、TCEIC(參(2-羧基乙基)異氰尿酸酯)(20.11g,58.2mmol)、正丁醇(20.11g,271.5mmol)、p-TSA(對甲苯磺酸酸)(0.53g,2.8mmol)溶解於34g苯甲醚中。使混合物加熱至150℃且在此溫度下維持3小時。使反應混合物冷卻至120℃且藉由添加78g HBM(2-羥基異丁酸甲酯)來稀釋。殘留單體藉由用過量異丙醇沈澱而移除,得到為白色粉末之所描繪共聚物1。[MW 7k,PDI=1.4;THEIC:TCEIC=66:34mol%,藉由13C-NMR測定]。
實例2:合成聚(ANTMA-共-HEMA-共-MMA)P2
藉由在裝備有機械攪拌棒、熱控制器、熱探針、加熱套及氮氣淨化進口(吹掃)之250ml三頸圓底燒瓶中,組合20.5g甲基丙烯酸甲基蒽酯單體、15.5g甲基丙烯酸2-羥乙酯單體、14.0g甲基丙烯酸甲酯及50g丙二醇單甲基醚乙酸酯(PGMEA)來製備聚合物進料溶液。加熱反應混合物,直至反應混合物之溫度達至80℃。接下來,將16.15g含有10wt%之Vazo 67偶氮引發劑(白色粉末,杜邦公司(Dupont))之PGMEA溶液添加至燒瓶中。在攪拌下,加熱燒瓶,直至反應混合物之溫度達至90℃,並維持6小時。停止加熱並使反應器冷卻至40℃。在真空條件下除去未反應之單體並用PGMEA將所得聚合物溶液稀釋至17wt%(+/-5wt%)。所得聚合物2溶液顯示[Mn 2776;Mw=8160;PDI 2.9 PDI;ANTMA:HEMA:MMA=20:35:45mol%,藉由13C-NMR測定]。
實例3:合成聚(ANTMA-共-GMA)P8
使250ml圓底3-頸燒瓶(反應器)裝入75g PGMEA(溶劑),並然後將燒瓶連接至冷凝器,熱電偶以達至溶劑,用於在整個聚合中量測並控制溶劑之溫度。將在反應器
內部之溶劑溫度設定在80℃±1℃。藉由在250mL玻璃瓶中組合22.72g甲基丙烯酸甲基蒽酯單體、27.28g甲基丙烯酸縮水甘油酯單體、1.26g V-601引發劑(2mol%)及75g丙二醇單甲基醚乙酸酯(PGMEA)來製備進料溶液,並然後振搖其以完全溶解單體及引發劑。然後將所述瓶放回至冰浴中。一旦反應器達至設定溫度(80℃),就將3.16g V-601引發劑(5mol%)傾倒於燒瓶中並攪拌約10分鐘。溫度達至80℃±1℃,將進料溶液進料至反應器燒瓶中,維持120分鐘。在進料之後,反應器在80℃下維持額外1小時,然後移去加熱且在攪拌下使反應器冷卻至室溫。所得聚合物溶液用甲醇(相對於反應混合物10×過量)沈澱,過濾並真空乾燥,以提供所得聚合物3,其顯示[Mw 8.5K;PDI 1.6;ANTMA:GMA=27:73mol%,藉由13C-NMR測定]。
實例4:由改性後聚合物P9合成兒茶酚化聚合物
向配備有磁性攪拌棒之250mL圓底燒瓶裝入聚(甲基丙烯酸縮水甘油酯)(10.00g,0.069mol)、3,4-二羥基苯甲酸(10.71g,0.035mol)以及乾燥CH3CN(210mL)。在攪拌情況下,向此溶液中添加1mol%之四丁基溴化銨(0.35mmol)且將所得混合物加熱至75℃並使其攪拌10小時。使所得透明溶液冷卻至環境溫度並藉由旋轉蒸發來濃縮以得到
10.24g黏性透明液體。將所得粗聚合物溶解於THF中,自冷IPA中沈澱且在真空中乾燥48小時。兒茶酚官能化聚合物P9(MW 6.5k)經分離為乾燥白色粉末,40%收率。
實例5-15及比較實例1-2
藉由組合表1中所示之量之組分來製備BARC組合物。通過具有0.45微米孔徑之PTFE過濾器過濾溶液,以提供BARC組合物。在表1中,在一般說明下指定之聚合物P1至聚合物P9具有如上文所闡述之te結構;PGMEA=丙二醇單甲基醚乙酸酯;HBM=甲基-2-羥基異丁酸酯;T1=對甲苯磺酸銨鹽;C-1=四甲氧基甲基甘脲以及F-1=來自OMNOVA溶液有限公司之含氟化合物界面活性劑Polyfox 656。
實例16:在組合物實例之TiN基板上測試濕式抗蝕刻性
BARC組合物各自以1500rpm旋塗在4cm×4cm TiN試片晶圓上,並然後使用小型塗佈機在215℃下烘烤一分鐘。烘烤之後BARC塗層厚度為1000Å。旋塗BARC膜置放在晶圓固持器上,用於浸漬至對於已知為SC-1混合物之TiN濕式蝕刻化學品中。此測試中使用之SC-1混合物具有NH4OH:H2O2:H2O=1:4:20之重量比。在將BARC膜浸漬於SC-1混合物中之後,將SC-1加熱至50℃。濕式抗蝕刻性樣品在此等些條件下顯示出較長之耐受時間而無BARC膜之任何剝
離,而較差黏附性之BARC在短時內剝離。藉由監測在SC-1混合物中膜剝落之耐受時間用作評估效能。
比較實例1及比較實例2表示廣泛用於ArF及KrF中之可商購BARC組合物。其在此濕式抗蝕刻性評估下顯示不充分之耐受時間。藉由使用含有兒茶酚或縮水甘油基之聚合物(實例14及實例15與比較實例1及比較實例2),顯著提高了在TiN基板上之濕式蝕刻耐受時間。藉由組合兒茶酚及縮水甘油基均聚物(實例8、9、10以及11)而非包含其中之一者之BARC組合物(實例14、15)來實現最佳效能。
實例17:量測BARC組合物之光學特性及耐溶劑性
將測試光學特性及耐溶劑性之各樣品溶液旋塗至Si晶圓上且在215℃下烘烤60秒。使用橢圓偏振測量法量測在Si晶圓上膜之n/k值及厚度。然後,將通常用於光致抗蝕劑領域中之PGME/PGMEA=70:30wt%混合溶液傾倒於BARC膜之表面上且使其靜置90秒。晶圓然後以4000rpm旋乾60秒。在110℃下額外烘烤60秒之後,用於移除溶劑。將
最終厚度及初始厚度之間之差值報告為溶劑剝除值。
實例18-微影處理
實例8及實例10之BARC組合物各自以1500rpm旋塗於150mm矽晶圓上,並然後使用TEL ACT 8晶圓塗佈軌跡機在215℃下烘烤一分鐘。在烘烤之後BARC塗層厚度為1000Å。將陶氏(DOW)EPIC2150光致抗蝕劑旋塗於BARC塗層之頂部上,並在125℃下烘烤60秒,以得到170nm厚之光致抗蝕劑層。接下來,使用尼康(Nikon)306C 193nm ArF掃描儀在0.78 NA下通過目標遮罩對光致抗蝕劑進行曝光。接下來,在105℃下對光致抗蝕劑層進行60秒之曝光後烘烤,並然後使用陶氏MFTM CD-26 TMAH顯影劑以標準60秒單攪煉製程進行顯影。在150k放大倍數下進行掃描電子顯微法以檢查光致抗蝕劑圖案輪廓之品質。
在與用於KrF微影之實例8及實例10之BARC組合物的相同條件下,製備使用實例12及實例13之BARC組合物之BARC塗層。將可商購之陶氏UVTM1610 DUV光致
抗蝕劑旋塗於BARC塗層之頂部上且在100℃下烘烤60秒,以得到280nm厚之光致抗蝕劑層。接下來,使用248nm KrF晶圓步進機在0.65 NA下通過目標遮罩對光致抗蝕劑進行曝光。接下來,在120℃下對光致抗蝕劑層進行60秒之曝光後烘烤,然後使用陶氏MFTM CD-26 TMAH顯影劑以標準60秒單攪煉製程進行顯影。在80k放大倍數下進行掃描電子顯微法,以檢查光致抗蝕劑圖案輪廓之品質。實例8及實例10、實例12以及實例13之BARC組合物對具有涉及材料之ArF及KrF兩者均顯示出良好的微影效能。
Claims (6)
- 一種形成光致抗蝕劑浮雕影像之方法,其包括:a)在基板上塗覆塗料組合物層,所述塗料組合物包括一或多種樹脂,所述一或多種樹脂包括:1)一或多個縮水甘油基;及2)一或多個芳族基,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基;以及b)將光致抗蝕劑組合物層塗覆在所述塗料組合物層上。
- 如請求項1之方法,其中所述一或多個芳族基包括兒茶酚部分。
- 如請求項1之方法,其中所述光致抗蝕劑組合物用活化輻射成像,且所述成像之光致抗蝕劑組合物層經顯影以提供光致抗蝕劑浮雕影像。
- 如請求項1之方法,其中光致抗蝕劑浮雕影像藉由濕式蝕刻製程轉印至基板。
- 一種經塗佈基板,其包括:基板,其上具有:a)包括一或多種樹脂之塗料組合物,所述一或多種樹脂包括:1)一或多個縮水甘油基;及2)一或多個芳族基,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基;以及b)在所述塗料組合物層上之光致抗蝕劑組合物層。
- 一種與外塗佈之光致抗蝕劑組合物一起使用之塗料組合物,所述塗料組合物包括:一或多種樹脂,其包括:(a)一或多個縮水甘油基;及(b)一或多個芳族基,各芳族基包括兩個或更多個包括羥基、硫醇及/或胺部分之取代基。
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KR102409417B1 (ko) * | 2016-05-02 | 2022-06-15 | 닛산 가가쿠 가부시키가이샤 | 특정 가교제를 포함하는 보호막 형성 조성물 및 이것을 이용한 패턴 형성 방법 |
KR102482878B1 (ko) * | 2017-09-26 | 2022-12-29 | 삼성전자 주식회사 | 집적회로 소자의 제조 방법 |
WO2019124475A1 (ja) | 2017-12-22 | 2019-06-27 | 日産化学株式会社 | アセタール構造を有する保護膜形成組成物 |
KR20200092952A (ko) | 2017-12-22 | 2020-08-04 | 닛산 가가쿠 가부시키가이샤 | 디올구조를 갖는 보호막형성 조성물 |
KR20210040357A (ko) * | 2018-07-31 | 2021-04-13 | 닛산 가가쿠 가부시키가이샤 | 레지스트 하층막 형성 조성물 |
KR102288386B1 (ko) | 2018-09-06 | 2021-08-10 | 삼성에스디아이 주식회사 | 레지스트 하층막용 조성물 및 이를 이용한 패턴 형성 방법 |
JP7110090B2 (ja) * | 2018-12-28 | 2022-08-01 | 東京エレクトロン株式会社 | 基板処理方法および基板処理システム |
JP7447813B2 (ja) | 2019-01-21 | 2024-03-12 | 日産化学株式会社 | アセタール構造及びアミド構造を有する保護膜形成組成物 |
US11651961B2 (en) * | 2019-08-02 | 2023-05-16 | Taiwan Semiconductor Manufacturing Co., Ltd. | Patterning process of a semiconductor structure with enhanced adhesion |
US11567408B2 (en) * | 2019-10-15 | 2023-01-31 | Rohm And Haas Electronic Materials Korea Ltd. | Coating composition for use with an overcoated photoresist |
JP7267968B2 (ja) * | 2020-03-27 | 2023-05-02 | 積水化成品工業株式会社 | 少なくとも一組の隣接水酸基により置換されたベンゼン環を側鎖に有するポリマーの製造方法 |
JPWO2023008355A1 (zh) * | 2021-07-30 | 2023-02-02 | ||
CN114085331B (zh) * | 2021-12-01 | 2024-05-28 | 长兴化学工业(中国)有限公司 | 一种贻贝仿生改性的丙烯酸杂化醇酸树脂及其制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003226982A (ja) * | 2001-11-29 | 2003-08-15 | Kansai Paint Co Ltd | 金属材料用表面処理組成物 |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3204465B2 (ja) * | 1992-07-17 | 2001-09-04 | 東京応化工業株式会社 | 半導体素子製造用レジストパターン形成材料及びそれを用いたパターン形成方法 |
US5576359A (en) | 1993-07-20 | 1996-11-19 | Wako Pure Chemical Industries, Ltd. | Deep ultraviolet absorbent composition |
JP3852889B2 (ja) * | 1998-09-24 | 2006-12-06 | 富士写真フイルム株式会社 | フォトレジスト用反射防止膜材料組成物 |
KR100465864B1 (ko) * | 1999-03-15 | 2005-01-24 | 주식회사 하이닉스반도체 | 유기 난반사방지 중합체 및 그의 제조방법 |
KR100310252B1 (ko) * | 1999-06-22 | 2001-11-14 | 박종섭 | 유기 반사방지 중합체 및 그의 제조방법 |
KR100492796B1 (ko) * | 1999-07-30 | 2005-06-07 | 주식회사 하이닉스반도체 | 초미세 패턴의 형성 공정에서 사용되는 반사방지용 수지 |
JP4210407B2 (ja) * | 2000-02-04 | 2009-01-21 | 富士フイルム株式会社 | レジスト積層物 |
US6444408B1 (en) | 2000-02-28 | 2002-09-03 | International Business Machines Corporation | High silicon content monomers and polymers suitable for 193 nm bilayer resists |
KR100721182B1 (ko) * | 2000-06-30 | 2007-05-23 | 주식회사 하이닉스반도체 | 유기반사방지막 조성물 및 그의 제조방법 |
US6846612B2 (en) | 2002-02-01 | 2005-01-25 | Brewer Science Inc. | Organic anti-reflective coating compositions for advanced microlithography |
ATE466310T1 (de) | 2002-02-11 | 2010-05-15 | Brewer Science Inc | Halogenierte antireflexbeschichtungen |
JP4150557B2 (ja) * | 2002-09-02 | 2008-09-17 | 富士フイルム株式会社 | 多層レジストプロセス用中間層材料組成物及びそれを用いたパターン形成方法 |
US7657838B2 (en) | 2002-10-08 | 2010-02-02 | At&T Intellectual Property I, L.P. | Preventing execution of programs that are embedded in email messages |
DE60330798D1 (de) | 2002-10-09 | 2010-02-11 | Nissan Chemical Ind Ltd | Zusammensetzung zur bildung einer antireflexschicht für die lithographie |
CN101560323B (zh) * | 2003-04-02 | 2012-07-04 | 日产化学工业株式会社 | 含有环氧化合物和羧酸化合物的光刻用形成下层膜的组合物 |
EP1850180A4 (en) | 2005-01-21 | 2009-12-30 | Nissan Chemical Ind Ltd | COMPOSITION FOR FORMING A LAYERING LINEOGRAPHY FILM CONTAINING A CARBOXYL PROTECTED COMPOSITION |
JP5557373B2 (ja) * | 2006-11-21 | 2014-07-23 | アボット ラボラトリーズ | 薬剤溶出性コーティングにおけるテトラフルオロエチレン、ヘキサフルオロプロピレン、及びフッ化ビニリデンのターポリマーの使用 |
JP5032362B2 (ja) * | 2007-03-12 | 2012-09-26 | ローム アンド ハース カンパニー | ヒドロキシフェニルアクリレート系モノマーおよびポリマー |
US20090035704A1 (en) | 2007-08-03 | 2009-02-05 | Hong Zhuang | Underlayer Coating Composition Based on a Crosslinkable Polymer |
JP4993139B2 (ja) | 2007-09-28 | 2012-08-08 | 信越化学工業株式会社 | 反射防止膜形成材料、反射防止膜及びこれを用いたパターン形成方法 |
WO2009119201A1 (ja) * | 2008-03-28 | 2009-10-01 | Jsr株式会社 | レジスト下層膜及びレジスト下層膜形成用組成物並びにレジスト下層膜形成方法 |
JP5125825B2 (ja) * | 2008-07-07 | 2013-01-23 | Jsr株式会社 | 多層レジストプロセス用下層膜形成組成物 |
TWI400575B (zh) | 2008-10-28 | 2013-07-01 | Shinetsu Chemical Co | 光阻劑下層膜形成材料及圖案形成方法 |
JP5177418B2 (ja) * | 2008-12-12 | 2013-04-03 | 信越化学工業株式会社 | 反射防止膜形成材料、反射防止膜及びこれを用いたパターン形成方法 |
JP5407941B2 (ja) * | 2009-03-09 | 2014-02-05 | 信越化学工業株式会社 | ポジ型レジスト材料並びにこれを用いたパターン形成方法 |
TWI490199B (zh) * | 2009-03-11 | 2015-07-01 | Sumitomo Chemical Co | 化合物及化學放大型正光阻組成物 |
US8722307B2 (en) * | 2011-05-27 | 2014-05-13 | International Business Machines Corporation | Near-infrared absorptive layer-forming composition and multilayer film comprising near-infrared absorptive layer |
JP5859420B2 (ja) | 2012-01-04 | 2016-02-10 | 信越化学工業株式会社 | レジスト下層膜材料、レジスト下層膜材料の製造方法、及び前記レジスト下層膜材料を用いたパターン形成方法 |
EP2805347B1 (en) | 2012-01-19 | 2018-03-07 | Brewer Science, Inc. | Nonpolymeric antireflection compositions containing adamantyl groups |
JP6449145B2 (ja) * | 2012-04-23 | 2019-01-09 | ブルーワー サイエンス アイ エヌ シー. | 感光性、現像液可溶性の底面反射防止膜材料 |
US11592747B2 (en) | 2012-12-14 | 2023-02-28 | Nissan Chemical Industries, Ltd. | Resist underlayer film-forming composition comprising carbonyl-containing polyhydroxy aromatic ring novolac resin |
WO2014097993A1 (ja) | 2012-12-18 | 2014-06-26 | 日産化学工業株式会社 | 多環芳香族ビニル化合物を含む自己組織化膜の下層膜形成組成物 |
JP6135600B2 (ja) * | 2013-06-11 | 2017-05-31 | 信越化学工業株式会社 | 下層膜材料及びパターン形成方法 |
CN105492973B (zh) * | 2013-08-28 | 2019-06-11 | 日产化学工业株式会社 | 应用了抗蚀剂下层膜的图案形成方法 |
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2016
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- 2016-11-18 CN CN201611015528.1A patent/CN106814543B/zh active Active
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003226982A (ja) * | 2001-11-29 | 2003-08-15 | Kansai Paint Co Ltd | 金属材料用表面処理組成物 |
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