CN115058175A - 与外涂布光致抗蚀剂一起使用的涂料组合物 - Google Patents
与外涂布光致抗蚀剂一起使用的涂料组合物 Download PDFInfo
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- CN115058175A CN115058175A CN202210808132.1A CN202210808132A CN115058175A CN 115058175 A CN115058175 A CN 115058175A CN 202210808132 A CN202210808132 A CN 202210808132A CN 115058175 A CN115058175 A CN 115058175A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/006—Anti-reflective coatings
-
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Abstract
与外涂布光致抗蚀剂一起使用的涂料组合物。本发明提供一种形成光致抗蚀剂浮雕图像的方法,其包含:a)在衬底上涂覆包含以下的涂料组合物层:1)包含一或多个氰尿酸酯基和聚酯键的树脂;和2)包含式(I)结构的交联剂;和b)在所述涂料组合物层上涂覆光致抗蚀剂组合物层。
Description
本发明专利申请是申请号为201610742216.4,申请日为2016年8月26日,名称为“与外涂布光致抗蚀剂一起使用的涂料组合物”的发明专利申请的分案申请。
技术领域
本发明涉及用于包含式(I)交联剂的本发明的微电子应用组合物的组合物,且确切地说,抗反射涂料组合物。本发明的优选组合物与外涂布光致抗蚀剂组合物一起使用且可称为底部抗反射组合物或“BARC”。
背景技术
光致抗蚀剂是用于将图像转移到衬底的感光膜。在衬底上形成光致抗蚀剂涂层并且随后经由光掩模使光致抗蚀剂层曝光于活化辐射源。在曝光之后,光致抗蚀剂被显影,得到允许选择性处理衬底的浮雕图像。
用于曝光光致抗蚀剂的活化辐射的反射通常对光致抗蚀剂层中图案化的图像的分辨率造成限制。来自衬底/光致抗蚀剂界面的辐射的反射可产生光致抗蚀剂中的辐射强度的空间变化,导致显影时的非均一光致抗蚀剂线宽。辐射还可从衬底/光致抗蚀剂界面散射到光致抗蚀剂的不预期曝光的区域中,再次导致线宽变化。
用于减少反射辐射问题的一种方法为使用***在衬底表面与光致抗蚀剂涂层之间的辐射吸收层。参见美国公布申请2007026458;2010029556;和2010009289;美国专利8334338;8142988;7691556;7638262;和7416821;以及WO2014185335。
对于许多高性能光刻应用,利用特定抗反射组合物以提供所需性能特性,如最优吸收特性和涂布特征。参见例如上文所提到的专利文献。尽管如此,电子装置制造商不断地寻求抗反射涂层上方图案化的光致抗蚀剂图像的增加的分辨率且转而需要抗反射组合物的不断增加的性能。
因此将期望具有与外涂布光致抗蚀剂一起使用的新颖抗反射组合物。将尤其期望具有展现增强的性能且可提供图案化到外涂布光致抗蚀剂中的图像的增加的分辨率的新颖抗反射组合物。
发明内容
我们现在提供可与外涂布光致抗蚀剂组合物一起使用的新颖涂料组合物。在优选方面中,本发明的涂料组合物可充当外涂布抗蚀剂层的有效抗反射层。
在优选方面中,提供有机涂料组合物,确切地说与外涂布光致抗蚀剂一起使用的抗反射组合物,其包含对如在组合物的涂层的热处理期间可能出现的从涂层的升华具抗性的交联剂组分。
更确切地说,提供涂料组合物,其包含:1)树脂;和2)在与树脂反应之前包含式(I)结构的交联剂:
其中在式(I)中:
每个R独立地选自氢、任选经取代的烷基、任选经取代的杂烷基、任选经取代的碳环芳基或任选经取代的杂芳基,
其中至少一个R基团不为氢;
R'和R”各自独立地选自氢、任选经取代的烷基或任选经取代的杂烷基、任选经取代的碳环芳基或任选经取代的杂芳基。
在优选方面中,R基团中的至少两个为相同或不同非氢基团,包括其中R基团中的三个或四个为相同或不同非氢基团。
如本文中所提及,“在与树脂反应之前的”交联剂意指在如光刻处理期间涂料组合物的交联剂和树脂组分的热诱导硬化或其它反应之前,在所述光刻处理中,含有树脂和式(I)交联剂的组合物的涂层将在超过100℃下加热30秒或更久。
在优选方面中,以上式(I)交联剂具有至少300、400、500、600、700、800、900或1000道尔顿的分子量。在某些方面中,交联剂具有小于1500道尔顿的分子量。在某些方面中,交联剂具有400或500道尔顿与1500道尔顿之间的分子量。
在其它优选方面中,式(I)交联剂为热稳定或耐热的,例如优选的交联剂具有大于250℃的降解温度。如本文中所提及,交联剂材料的降解温度如通过下文实例11中定义的以下方案测定而定义。
在尤其优选的方面中,此类热稳定交联剂(例如具有大于250℃的降解温度)也有效地起交联抗反射组合物涂层的作用,即包含交联剂的如本文中所公开的组合物的涂层将硬化以防止在175℃下加热抗反射组合物层60秒之后与随后涂覆的流体光致抗蚀剂组合物的不合需要的互混。
关于抗反射应用,本发明的底层组合物还优选地含有包含发色团的组分,所述发色团可吸收用于曝光外涂布抗蚀剂层的不合需要的辐射,免于反射回抗蚀剂层中。树脂或交联剂可包含此类发色团,或涂料组合物可包含另一包含适合发色团的组分。
在与外涂布光致抗蚀剂一起使用中,涂料组合物可涂覆于衬底上,如上面可具有一或多个有机或无机涂层的半导体晶片。涂覆的涂层可任选地在用光致抗蚀剂层外涂布之前经热处理。此类热处理可引起涂料组合物层的硬化,包括交联。此类交联可包括一或多种组合物组分之间的硬化和/或共价键形成反应且可调节涂料组合物层的水接触角。
此后,光致抗蚀剂组合物可涂覆于涂料组合物层上方,接着通过图案化活化辐射对涂覆的光致抗蚀剂组合物层成像且成像的光致抗蚀剂组合物层经显影,得到光致抗蚀剂浮雕图像。
多种光致抗蚀剂可与本发明的涂料组合物组合使用(即外涂布)。与本发明的底层涂料组合物一起使用的优选光致抗蚀剂为化学放大抗蚀剂,尤其为负型光致抗蚀剂,其含有一或多种光敏化合物和含有在存在光生酸的情况下经历解块或裂解反应的单元的树脂组分。
在优选方面中,光致抗蚀剂组合物被设计用于负型抗蚀剂,其中曝光区域在显影过程之后保留,但正型显影还可用于去除光致抗蚀剂层的曝光部分。
本发明进一步提供形成光致抗蚀剂浮雕图像和包含涂布有单独或与光致抗蚀剂组合物组合的本发明的涂料组合物的衬底(如微电子晶片衬底)的新颖制品的方法。还提供式(I)的交联剂材料。
本发明的其它方面公开于下文中。
具体实施方式
如上文所论述,提供有机涂料组合物,确切地说与外涂布光致抗蚀剂一起使用的抗反射组合物,其包含对如在组合物的涂层的热处理期间可能出现的从涂层的升华具抗性的交联剂组分。
不受任何理论限制,相信底层涂料组合物的一或多种组分可在光刻处理期间迁移出涂覆的涂层。确切地说,相信在热处理涂覆的涂料组合物以交联或以其它方式硬化涂层期间,一或多种组合物组分可从涂层升华或以其它方式迁移。此类升华材料可以多种方式损害光刻性能,包括通过在随后涂覆的光致抗蚀剂涂层上沉积。
如上文所论述,我们提供包含以下的涂料组合物:
1)树脂;和
2)在与树脂反应之前包含式(I)结构的交联剂:
其中在式(I)中:
每个R独立地选自氢、任选经取代的烷基、任选经取代的杂烷基、任选经取代的碳环芳基或任选经取代的杂芳基,
其中至少一个R不为氢;
R'和R”各自独立地选自氢、任选经取代的烷基或任选经取代的杂烷基、任选经取代的碳环芳基或任选经取代的杂芳基。
在式(I)交联剂中,优选的R基团包括具有1到20个碳原子,更通常1到12个或15个碳原子的任选经取代的烷基;具有一或多个N、O或S原子和1到20个碳原子,更通常1到12个或15个碳原子的任选经取代的杂烷基,任选经取代的碳环芳基,如任选经取代的苯基、萘基或蒽基,或任选经取代的杂芳族基。
尤其优选的R基团将含有总共至少4、5或6个碳原子或杂(N、O和/或S)原子。举例来说,尤其优选的R基团包括包含任选经取代的碳脂环族,如任选经取代的环己基的那些。
一般也优选的是式(I)交联剂含有至少两个为相同或不同非氢取代基的R基团。同样优选的是含有三个或四个为相同或不同非氢取代基的R基团的式(I)交联剂。
优选地,如果式(I)交联剂含有单一R基团,那么含有此类交联剂的涂料组合物还优选地将含有酸或酸源,如热酸产生剂化合物以促进涂料组合物的反应。
如本文中所提及,适合的杂烷基包括任选经取代的C1-20烷氧基、优选地具有1到约20个碳原子的任选经取代的烷硫基;优选地具有1到约20个碳原子的任选经取代的烷基亚磺酰基;优选地具有1到约20个碳原子的任选经取代的烷基磺酰基;和优选地具有1到约20个碳原子的任选经取代的烷基胺。
如本文中所提及,术语“碳脂环基”意味着非芳族基的每一环成员都是碳。碳脂环基可具有一或多个内环碳-碳双键,其限制条件是所述环不是芳族环。术语任选经取代的“环烷基”意味着非芳族基的每一环成员都是碳,并且碳环不具有任何内环碳-碳双键。举例来说,环己基、环戊基和金刚烷基是环烷基以及碳脂环基。碳脂环基和环烷基可包含一个环或多个(例如2、3、4个或更多个)桥联、稠合或以其它方式共价连接的环。
如本文中所提及,“杂芳基”包括具有1-3个杂原子(如果为单环)、1-6个杂原子(如果为双环)或1-9个杂原子(如果为三环)的芳族5-8元单环、8-12元双环或11-14元三环环***,所述杂原子选自O、N或S(例如个碳原子和1-3、1-6或1-9个N、O或S杂原子,分别为如果为单环、双环或三环),其中每一环的0、1、2、3或4个原子可经取代基取代。杂芳基的实例包括吡啶基、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、噻唑基等。
“任选经取代的”各种材料和取代基(包括上文式(I)的基团A、B、X和Y)可在一或多个可用位置适当地经例如以下者取代:卤素(F、Cl、Br、I);硝基;羟基;氨基;烷基,如C1-8烷基;烯基,如C2-8烯基;烷基氨基,如C1-8烷基氨基;碳环芳基,如苯基、萘基、蒽基等;等等。
在一般优选的方面中,热处理之前的涂料组合物的树脂和交联剂组分为相异且分离的材料,即树脂组分和交联剂组分不共价连接。在某些其它实施例中,交联剂组分可连接到树脂组分,例如以侧基形式共价系栓。
多种树脂可充当底层涂料组合物的树脂组分。
本发明的涂料组合物的尤其优选的树脂可包含聚酯键。聚酯树脂可通过一或多种多元醇试剂与一或多种含羧基(如羧酸、酯、酸酐等)化合物的反应容易地制备。适合的多元醇试剂包括二醇、甘油和三醇,如二醇,如二醇为乙二醇、1,2-丙二醇、1,3-丙二醇、丁二醇、戊二醇、环丁基二醇、环戊基二醇、环己基二醇、二羟甲基环己烷,和三醇,如甘油、三羟甲基乙烷、三羟甲基丙烷等。
用于本发明的抗反射组合物的优选聚酯树脂公开于U.S.8,501,383;U.S.2011/0033801;和U.S.7,163,751中。如那些专利文献中所公开,含有酯重复单元(聚酯)的树脂可通过含羧基化合物(如羧酸、酯、酸酐等)与含羟基化合物的聚合适当地提供,所述含羟基化合物优选地为具有多个羟基的化合物,如二醇,例如乙二醇或丙二醇,或甘油,或其它二醇、三醇、四醇等。在某些方面中,优选地,酯官能团以聚合物主链的组分或聚合物主链内的组分形式,而非以侧接或侧链单元形式存在。酯部分还可以侧基形式存在,但优选地,聚合物还含有沿聚合物主链的酯官能团。还优选的是酯重复单元包含芳族取代,如任选经取代的碳环芳基,例如任选经取代的苯基、萘基或蒽基取代,其呈侧链形式或更优选地沿聚合物主链。
本发明的涂料组合物的树脂可包含多种额外基团,如氰尿酸酯基,如美国专利6852421和8501383中所公开。
本发明的涂料组合物的尤其优选的基质树脂可包含一或多个氰尿酸酯基和聚酯键。
如所论述,对于抗反射应用,适当地,经反应以形成树脂的化合物中的一或多者包含可充当发色团以吸收用于曝光外涂布光致抗蚀剂涂层的辐射的部分。举例来说,邻苯二甲酸酯化合物(例如邻苯二甲酸或邻苯二甲酸二烷酯(即二酯,如每一酯具有1-6个碳原子,优选地邻苯二甲酸二甲基酯或邻苯二甲酸二乙酯))可与芳族或非芳族多元醇和任选地其它反应性化合物聚合,得到在用于在低于200nm波长,如193nm下成像的光致抗蚀剂的涂料组合物中尤其适用的聚酯。异氰尿酸酯化合物还可与一或多种多元醇聚合,得到适用于本发明底层涂料组合物的树脂。树脂用于具有在低于300nm波长或低于200nm波长,如248nm或193nm下成像的外涂布光致抗蚀剂的组合物,萘基化合物可经聚合,如含有一个或两个或更多个羧基取代基的萘基化合物,例如萘二甲酸二烷酯,尤其为萘二甲酸二-C1-6烷酯。反应性蒽化合物也为优选的,例如具有一或多个羧基或酯基,如一或多个甲酯或乙酯基的蒽化合物。
含有发色团单元的化合物还可含有一个或优选地两个或更多个羟基且与含羧基化合物反应。举例来说,具有一个、两个或更多个羟基的苯基化合物或蒽化合物可与含羧基化合物反应。
另外,用于抗反射目的的底层涂料组合物可含有一种含有与提供水接触角调变的树脂组分(例如含有光酸不稳定基团和/或碱反应性基团的树脂分离的发色团单元的材料)。举例来说,涂料组合物可包含含有苯基、蒽、萘基等单元的聚合或非聚合化合物。然而,通常优选的是提供水接触角调变的一或多种树脂还含有发色团部分。
优选地,本发明的底层涂料组合物的树脂将具有约1,000到约10,000,000道尔顿,更通常约2,000到约100,000道尔顿的重量平均分子量(Mw)和约500到约1,000,000道尔顿的数目平均分子量(Mn)。本发明组合物的树脂的分子量(Mw或Mn)通过凝胶渗透色谱法适当地测定。
树脂组分将为许多优选实施例中的底层涂料组合物的主要固体组分。举例来说,树脂适当地可以按涂料组合物的总固体含量计的50到99.9重量%,更通常按涂料组合物的总固体含量计的80到95重量%存在。如本文中所提及,涂料组合物的固体是指除了溶剂载体以外的涂料组合物的所有材料。
在某些实施例中,本发明的涂料组合物可包含除式(I)交联剂以外的交联剂。举例来说,涂料组合物可包括基于胺的交联剂,如三聚氰胺材料,包括三聚氰胺树脂,如由CytecIndustries制造且以商品名Cymel 300、301、303、350、370、380、1116和1130销售;甘脲,包括购自Cytec Industries的那些甘脲;和基于苯并三聚氰胺和脲的材料,包括树脂,如以名称Cymel 1123和1125购自Cytec Industries的苯并三聚氰胺树脂,和以名称Powderlink1174和1196购自Cytec Industries的脲树脂。除可商购以外,此类基于胺的树脂可例如通过丙烯酰胺或甲基丙烯酰胺共聚物与甲醛在含醇溶液中的反应,或者通过N-烷氧基甲基丙烯酰胺或甲基丙烯酰胺与其它适合单体的共聚制备。
本发明的涂料组合物的交联剂组分一般以涂料组合物的总固体(除了溶剂载体的所有组分)的约5与50重量%之间的量,更通常以约5到25重量%总固体的量存在。
尤其优选的本发明的涂料组合物还可含有热酸产生剂化合物。通过热酸产生剂的活化的涂料组合物的热诱导交联一般为优选的。
用于涂料组合物的适合的热酸产生剂化合物包括离子或大体上中性的热酸产生剂,例如芳烃磺酸铵盐(例如甲苯磺酸铵盐),用于在抗反射组合物涂层的固化期间催化或促进交联。通常,一或多种热酸产生剂以组合物的总干式组分(除了溶剂载体的所有组分)的约0.1到10重量百分比,更优选地总干式组分的约0.5到2重量百分比的浓度存在于涂料组合物中。
本发明的涂料组合物(尤其用于反射控制应用)还可含有吸收用于曝光外涂布光致抗蚀剂层的辐射的额外染料化合物。其它任选的添加剂包括表面调平剂,例如可以商品名Silwet 7604获得的调平剂,或购自3M Company的表面活性剂FC 171或FC 431。
本发明的底层涂料组合物还可含有其它材料,如光酸产生剂,包括与外涂布光致抗蚀剂组合物一起使用的如所论述的光酸产生剂。关于光酸产生剂在抗反射组合物中的此类用途的论述,参见美国专利6261743。
为了制造本发明的液体涂料组合物,涂料组合物的组分溶解于适合溶剂中,如一或多种氧基异丁酸酯,尤其为2-羟基异丁酸甲酯、乳酸乙酯或如2-甲氧基***(二乙二醇二甲醚)、乙二醇单甲醚和丙二醇单甲醚的二醇醚中的一或多者;具有醚和羟基部分两者的溶剂,如甲氧基丁醇、乙氧基丁醇、甲氧基丙醇和乙氧基丙醇;2-羟基异丁酸甲酯;酯,如溶纤剂乙酸甲酯、溶纤剂乙酸乙酯、丙二醇单甲醚乙酸酯、二丙二醇单甲醚乙酸酯和其它溶剂,如二元酯,碳酸亚丙酯和γ-丁内酯。溶剂中的干式组分的浓度将取决于若干因素,如涂覆方法。一般来说,底层涂料组合物的固体含量在涂料组合物的总重量的约0.5到20重量%范围内变化,优选地,固体含量在涂料组合物的约0.5到10重量范围内变化。
例示性光致抗蚀剂***
与底层涂料组合物一起使用的光致抗蚀剂通常包含聚合物和一或多种酸产生剂。一般优选的是正型抗蚀剂和抗蚀剂聚合物具有赋予抗蚀剂组合物碱性水溶性的官能团。举例来说,优选的是包含极性官能团(如羟基或羧酸酯基)或在光刻处理后可释放此类极性部分的酸不稳定基团的聚合物。优选地,聚合物以足以使得抗蚀剂可用碱性水溶液显影的量用于抗蚀剂组合物中。
酸产生剂还适当地与包含含有芳族基(如包括苯酚的任选经取代的苯基、任选经取代的萘基和任选经取代的蒽)的重复单元的聚合物一起使用。含有任选经取代的苯基(包括苯酚)的聚合物尤其适合于许多抗蚀剂***,包括用EUV和电子束辐射成像的那些抗蚀剂***。对于正性作用抗蚀剂,聚合物优选地也含有一或多个包含酸不稳定基团的重复单元。举例来说,在含有任选经取代的苯基或其它芳族基的聚合物的情况下,聚合物可包含含有一或多个酸不稳定部分的重复单元,如通过使丙烯酸酯或甲基丙烯酸酯化合物的单体与酸不稳定酯(例如丙烯酸叔丁酯或甲基丙烯酸叔丁酯)聚合而形成的聚合物。此类单体可与一或多种包含芳族基(如,任选地苯基)的其它单体(例如苯乙烯或乙烯基苯酚单体)共聚。
用于形成此类聚合物的优选单体包括:具有下式(V)的酸不稳定单体、下式(VI)的含内酯单体、用于调节碱性显影剂中的溶解速率的下式(VII)的碱可溶单体和下式(VIII)的酸产生单体,或包含前述单体中的至少一者的组合:
其中每一Ra独立地为H、F、-CN、C1-10烷基或C1-10氟烷基。在式(V)的酸可脱保护单体中,Rb独立地为C1-20烷基、C3-20环烷基、C6-20芳基或C7-20芳烷基,并且每一Rb为独立的或至少一个Rb键结到相邻Rb以形成环状结构。在式(VI)的含内酯单体中,L为单环、多环或稠合多环C4-20含内酯基团。在式(VII)的碱可溶单体中,W为卤代或非卤代、芳族或非芳族C2-50含羟基有机基团,其pKa小于或等于12。在式(VIII)的酸产生单体中,Q为含酯或非含酯的且为氟化或非氟化的,且为C1-20烷基、C3-20环烷基、C6-20芳基或C7-20芳烷基;A为含酯或非含酯的且为氟化或非氟化的,且为C1-20烷基、C3-20环烷基、C6-20芳基或C7-20芳烷基基团;Z-为阴离子部分,包含羧酸根、磺酸根、磺酰胺阴离子或磺酰亚胺阴离子;并且G+为锍或錪阳离子。
例示性酸可脱保护单体包括(但不限于):
或包含至少一种前述单体的组合,其中Ra为H、F、-CN、C1-6烷基或C1-6氟烷基。
适合的内酯单体可为下式(IX)的单体:
其中Ra为H、F、-CN、C1-6烷基或C1-6氟烷基,R为C1-10烷基、环烷基或杂环烷基,并且w为0到5的整数。在式(IX)中,R直接连接到内酯环上或通常连接到内酯环和/或一或多个R基团上,并且酯部分直接连接或经由R间接连接到内酯环上。
例示性含内酯单体包括:
或包含至少一种前述单体的组合,其中Ra为H、F、-CN、C1-10烷基或C1-10氟烷基。
适合的碱可溶单体可为下式(X)的单体:
其中每一Ra独立地为H、F、-CN、C1-10烷基或C1-10氟烷基,A为含羟基或非含羟基、含酯或非含酯、氟化或非氟化的C1-20亚烷基、C3-20亚环烷基、C6-20亚芳基或C7-20亚芳烷基,并且x为0到4的整数,其中当x为0时,A为含羟基的C6-20亚芳基。
例示性碱可溶单体包括具有以下结构的那些单体:
或包含至少一种前述单体的组合,其中Ra为H、F、-CN、C1-6烷基或C1-6氟烷基。
优选的酸产生单体包括式(XI)或(XII)的那些单体:
其中每一Ra独立地为H、F、-CN、C1-6烷基或C1-6氟烷基,A为经氟取代的C1-30亚烷基、经氟取代的C3-30亚环烷基、经氟取代的C6-30亚芳基或经氟取代的C7-30亚烷基亚芳基,并且G+是硫鎓或錪阳离子。
优选地,在式(XI)和式(XII)中,A为-[(C(R1)2)xC(=O)O]b-C((R2)2)y(CF2)z-基团或邻位、间位或对位取代的-C6F4-基团,其中每一R1和R2各自独立地为H、F、-CN、C1-6烷基或C1-6氟烷基,b为0或1,x为1到10的整数,y和z独立地为0到10的整数,并且y+z的总和为至少1。
例示性优选的酸产生单体包括:
或包含至少一种前述单体的组合,其中每一Ra独立地为H、F、-CN、C1-6烷基或C1-6氟烷基,k适当地为0到5的整数;并且G+为锍或錪阳离子。如在本文各种式中所提及的G+可为如本文中所公开的酸产生剂且包含氧代-二氧杂环戊烷部分和/或氧代-二噁烷部分。
优选的酸产生单体可包括锍或錪阳离子。优选地,在式(IV)中,G+具有式(XIII):
其中X为S或I;每一R0为卤代或非卤代的并且独立地为C1-30烷基、多环或单环C3-30环烷基、多环或单环C4-30芳基或包含至少一种前述基团的组合,其中当X为S时,R0基团中的一个任选地通过单键连接到一个相邻R0基团,并且a为2或3,其中当X为I时,a为2,或当X为S时,a为3。
例示性酸产生单体包括具有下式的那些单体:
特别适用于本发明正性作用化学放大光致抗蚀剂中的具有酸不稳定解块基团的聚合物已经公开于欧洲专利申请0829766A2(具有缩醛的聚合物和缩酮聚合物)和欧洲专利申请EP0783136A2(包括1)苯乙烯;2)羟基苯乙烯;和3)酸不稳定基团,确切地说丙烯酸烷酯酸不稳定基团)单元的三元共聚物和其它共聚物中。
用于在低于200nm,如193nm下成像的光致抗蚀剂的其它优选树脂包含以下通式(I)、(II)和(III)的单元:
用于在低于200nm,如193nm下成像的光致抗蚀剂的优选树脂包含以下通式(I)、(II)和(III)的单元:
其中:R1为(C1-C3)烷基;R2为(C1-C3)亚烷基;L1为内酯基;且n为1或2。
用于本发明光致抗蚀剂中的聚合物的分子量和多分散性可适当地大幅变化。适合的聚合物包括Mw为约1,000到约50,000、更通常约2,000到约30,000并且分子量分布为约3或更小、更通常分子量分布为约2或更小的那些聚合物。
优选的本发明负性作用组合物包含在暴露于酸后将固化、交联或硬化的材料和两种或更多种如本文中所公开的酸产生剂的混合物。优选的负性作用组合物包含聚合物粘合剂(如酚系或非芳族聚合物)、交联剂组分和本发明的光敏组分。此类组合物和其用途已公开于欧洲专利申请0164248和美国专利第5,128,232号(Thackeray等人)中。用作聚合物粘合剂组分的优选的酚系聚合物包括酚醛清漆和聚(乙烯基苯酚),如上文所述的那些。优选的交联剂包括基于胺的材料(包括三聚氰胺)、甘脲、基于苯并胍胺的材料以及基于脲的材料。三聚氰胺-甲醛聚合物通常尤其适合。此类交联剂是可商购的,例如三聚氰胺聚合物、甘脲聚合物、基于脲的聚合物和苯并胍胺聚合物,如由Cytec以商品名称Cymel 301、303、1170、1171、1172、1123和1125以及Beetle 60、65和80销售的那些交联剂。
尤其优选的本发明的光致抗蚀剂可用于浸没式光刻应用中。关于优选浸没式光刻光致抗蚀剂和方法的论述,参见例如Rohm and Haas Electronic Materials的U.S.7968268。
本发明的光致抗蚀剂还可包含单一酸产生剂或相异酸产生剂的混合物,通常2或3种不同酸产生剂的混合物,更通常由总共2种相异酸产生剂组成的混合物。光致抗蚀剂组合物包含以在曝光于活化辐射后足以在组合物的涂层中产生潜像的量采用的酸产生剂。举例来说,酸产生剂将适当地以按光致抗蚀剂组合物的总固体计1到20重量%的量存在。
适合的酸产生剂为化学放大光致抗蚀剂领域中已知的并且包括例如:鎓盐,例如三氟甲烷磺酸三苯基锍、三氟甲烷磺酸(对叔丁氧基苯基)二苯基锍、三氟甲烷磺酸三(对叔丁氧基苯基)锍、对甲苯磺酸三苯基锍;硝基苯甲基衍生物,例如2-硝基苯甲基-对甲苯磺酸盐、2,6-二硝基苯甲基-对甲苯磺酸盐以及2,4-二硝基苯甲基-对甲苯磺酸盐;磺酸酯,例如1,2,3-三(甲烷磺酰基氧基)苯、1,2,3-三(三氟甲烷磺酰基氧基)苯以及1,2,3-三(对甲苯磺酰基氧基)苯;重氮甲烷衍生物,例如双(苯磺酰基)重氮甲烷、双(对甲苯磺酰基)重氮甲烷;乙二肟衍生物,例如双-O-(对甲苯磺酰基)-α-二甲基乙二肟和双-O-(正丁烷磺酰基)-α-二甲基乙二肟;N-羟基酰亚胺化合物的磺酸酯衍生物,例如N-羟基丁二酰亚胺甲磺酸酯、N-羟基丁二酰亚胺三氟甲磺酸酯;以及含卤素的三嗪化合物,例如2-(4-甲氧基苯基)-4,6-双(三氯甲基)-1,3,5-三嗪以及2-(4-甲氧基萘基)-4,6-双(三氯甲基)-1,3,5-三嗪。
如本文中所提及,酸产生剂可在曝光于活化辐射,如EUV辐射、电子束辐射、193nm波长辐射或其它辐射源后产生酸。如本文中所提及的酸产生剂化合物也可被称为光酸产生剂化合物。
本发明的光致抗蚀剂也可含有其它材料。举例来说,其它任选的添加剂包括光化和造影染料、抗条纹剂、塑化剂、速度增强剂和敏化剂。此类任选的添加剂通常将以较小浓度存在于光致抗蚀剂组合物中。
或者或另外,其它添加剂可包括淬灭剂,其为非光可破坏碱,如基于氢氧化物、羧酸盐、胺、亚胺和酰胺的那些碱。优选地,此类淬灭剂包括C1-30有机胺、亚胺或酰胺,或可为强碱(例如氢氧化物或醇盐)或弱碱(例如羧酸盐)的C1-30季铵盐。例示性淬灭剂包括胺,如三丙胺、十二烷胺、三(2-羟丙基)胺、四(2-羟丙基)乙二胺;芳基胺,如二苯胺、三苯胺、氨基苯酚和2-(4-氨基苯基)-2-(4-羟基苯基)丙烷,受阻胺,如二氮杂双环十一烯(DBU)或二氮杂二环壬烯(DBN),或离子淬灭剂,包括季烷基铵盐,如氢氧化四丁铵(TBAH)或乳酸四丁铵。
表面活性剂包括氟化和非氟化的表面活性剂,并且优选地为非离子的。例示性氟化非离子表面活性剂包括全氟C4表面活性剂,如可自3M Corporation购得的FC-4430和FC-4432表面活性剂;和氟二醇,如来自Omnova的POLYFOX PF-636、PF-6320、PF-656和PF-6520氟表面活性剂。
光致抗蚀剂进一步包括一般适合于溶解、分配和涂布光致抗蚀剂中所用组分的溶剂。例示性溶剂包括苯甲醚;醇,包括乳酸乙酯、1-甲氧基-2-丙醇和1-乙氧基-2丙醇;酯,包括乙酸正丁酯、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,包括环己酮和2-庚酮;以及包含至少一种前述溶剂的组合。
光刻加工
在使用中,本发明的涂料组合物通过如旋涂的多种方法中的任一种以涂层形式涂覆到衬底。涂料组合物一般以约0.02与0.5μm之间的干燥层厚度,优选地约0.04与0.20μm之间的干燥层厚度涂覆于衬底上。衬底适当地为任何用于涉及光致抗蚀剂的方法中的衬底。举例来说,衬底可为硅、二氧化硅或铝-氧化铝微电子晶片。也可采用砷化镓、碳化硅、陶瓷、石英或铜衬底。还适当地采用用于液晶显示器或其它平板显示器应用的衬底,例如玻璃衬底、氧化铟锡涂布衬底等。还可采用用于光学和光电装置(例如波导)的衬底。
优选地,涂覆的涂层在光致抗蚀剂组合物涂覆于底层涂料组合物上方之前固化。固化条件将随着底层涂料组合物的组分而变化。确切地说,固化温度将取决于涂料组合物中采用的特定酸或酸(热)产生剂。典型固化条件为约80℃到225℃下持续约0.5到5分钟。固化条件优选地使得涂料组合物涂层基本上不溶于使用的光致抗蚀剂溶剂以及显影剂溶液。
在此类固化之后,光致抗蚀剂涂覆于涂覆的涂料组合物的表面上。如同底部涂料组合物层的涂覆,外涂布光致抗蚀剂可通过任何标准方法,如通过旋涂、浸涂、弯月面涂布或滚涂来涂覆。在涂覆后,光致抗蚀剂涂层通常通过加热干燥以去除溶剂,优选地直到抗蚀剂层无粘性。最优地,应基本上不出现底部组合物层与外涂布光致抗蚀剂层的互混。
抗蚀剂层接着用活化辐射,如以常规方式穿过遮罩的248nm、193nm或EUV辐射成像。曝光能量足以有效地活化抗蚀剂***的光敏组分以在抗蚀剂涂层中产生图案化图像。通常,曝光能量的范围介于约3到300mJ/cm2且部分取决于采用的曝光工具和特定抗蚀剂和抗蚀剂处理。曝光的抗蚀剂层可在必要时经受曝光后烘烤以在涂层的曝光于未曝光区域之间产生或增强溶解性差异。举例来说,负型酸硬化光致抗蚀剂通常需要曝光后加热以诱导酸促进的交联反应,且许多化学放大正性作用抗蚀剂需要曝光后加热以诱导酸促进的脱除保护基反应。通常,曝光后烘烤条件包括约50℃或更高的温度,更确切地说约50℃到约160℃范围内的温度。
光致抗蚀剂层还可曝光于浸没式光刻***中,即其中曝光工具(尤其投影透镜)与光致抗蚀剂涂布衬底之间的空间通过浸没流体,如水或与一或多种添加剂(如可提供增强的折射率的流体的硫酸铯)混合的水占据。优选地,浸没流体(例如水)已经处理以避免气泡,例如水可经脱气以避免纳米气泡。
本文中提及“浸没曝光”或其它类似术语指示曝光在此类流体层(例如水或具有添加剂的水)***在曝光工具与经涂布的光致抗蚀剂组合物层之间的情况下进行。
曝光的光致抗蚀剂层接着用能够选择性地去除膜的一部分以形成光致抗蚀剂图案的适合显影剂处理。在负型显影方法中,光致抗蚀剂层的未曝光区域可通过用适合非极性溶剂处理选择性地去除。关于负型显影的适合程序,参见U.S.2011/0294069。用于负型显影的典型非极性溶剂为有机显影剂,如选自酮、酯、烃和其混合物的溶剂,例如丙酮、2-己酮、2-庚酮、乙酸甲酯、乙酸丁酯和四氢呋喃。用于NTD方法中的光致抗蚀剂材料优选地形成可与有机溶剂显影剂形成负像或与如四烷基氢氧化铵溶液的水性碱显影剂形成正像的光致抗蚀剂层。优选地,NTD光致抗蚀剂是基于具有酸敏(可脱保护)基团的聚合物,所述基团在脱除保护基时形成羧酸基和/或羟基。
或者,曝光的光致抗蚀剂层的显影可通过用能够选择性地去除膜的曝光部分(其中光致抗蚀剂是正型)或去除膜的未曝光部分(其中光致抗蚀剂在曝光区域中可交联,即为负型)的适合显影剂处理曝光层来实现。优选地,光致抗蚀剂为正型的,其基于具有在脱除保护基时形成羧酸基的酸敏(可脱保护)基团的聚合物,且显影剂优选地为金属离子自由四烷基氢氧化铵溶液,如0.26N四甲基氢氧化铵水溶液。图案通过显影形成。
显影的衬底可接着根据所属领域中众所周知的程序在缺乏光致抗蚀剂的那些衬底区域,例如缺乏光致抗蚀剂的化学蚀刻或镀敷区域上选择性地处理。适合的蚀刻剂包括氢氟酸蚀刻溶液和等离子气体蚀刻剂,如氧等离子体蚀刻剂。等离子气体蚀刻去除底层涂层。
以下非限制性实例说明本发明。
实例1:制备四(环己氧基甲基)-3a-丁基-6a-甲基甘脲
标题化合物四(环己氧基甲基)-3a-丁基-6a-甲基甘脲如紧邻的上文流程中所示且如下制备:
(a)向配备有磁力搅拌棒的100mL圆底烧瓶中溶解含2,3-庚二酮(3.915g,30.5mmol)的水(57mL)。向此溶液中馈入磷酸酐(4.86g,17.1mmol)且使此溶液搅拌10分钟。向此所得透明、无色溶液中馈入尿素(5.393g,89.8mmol)且使整个反应混合物在环境温度下搅拌20分钟。所得非均质溶液冷却到环境温度且通过过滤收集固体。用冷水洗涤固体,随后在高真空下干燥,得到呈2.74g(42%产率)白色粉末形式的3a-丁基-6a-甲基-甘脲。1HNMR(d6-DMSO)δ=7.14(2H,s),7.06(2H,s),1.59(2H,m),1.35(7H,m),0.87(3H,t,J=7.5Hz)ppm。13C NMR(d6-DMSO)δ=160.22,160.12,77.83,76.02,35.48,25.19,22.95,21.97,14.34ppm。
(b)向配备有磁力搅拌棒的25mL闪烁瓶中馈入3a-丁基-6a-甲基-甘脲(1.71g,8.1mmol)和8mL水。向此混合物中馈入三聚甲醛(1.91g,63.7mmol)和1mL 5%NaOH(16%)。此混合物加热到50℃且使其搅拌过夜。透明、均质溶液在热搅拌时过滤且所得溶液蒸发到干燥,得到粘滞油,其不经任何进一步纯化即用于下一步骤中。
(c)向配备有磁力搅拌棒的100mL圆底烧瓶中馈入前述粘滞油、环己醇(20g,199.7mmol)和浓硝酸(4.2mL,65.4mmol)。此混合物在搅拌时加热到60℃且保持于所述温度下过夜。所得混合物接着用5%氢氧化钠(溶液)中和,随后用二氯甲烷(2×)萃取。经合并的有机洗脱份用盐水洗涤,经无水硫酸镁干燥,接着通过旋转蒸发来浓缩,获得粗产物混合物,所述混合物在2℃下静置过夜后产生呈无色针状的四(环己氧基甲基)-3a-丁基-6a-甲基甘脲(0.38g,7.1%,经两个步骤),其通过真空过滤收集。通过第二结晶收集额外产物,得到总产量为至多1.1克(20.7%,经两个步骤)的标题化合物四(环己氧基甲基)-3a-丁基-6a-甲基甘脲。1H NMR(d6-DMSO)δ=5.22(1H,d,J=10Hz),5.20(1H,d,J=10Hz),5.01(1H,d,J=10Hz),4.95(1H,d,J=10Hz),3.38(4H,m)2.28(2H,dd,J=7.5,7.5Hz),1.84(3H,s),1.73(6H,m),1.64(6H,m),1.46(4H,m),1.39(4H,m),1.22-1.11(20H,m),0.91(3H,dd,J=5.0,5.0Hz)ppm。13C NMR(d6-DMSO)158.04,75.79,74.04,70.82,70.57,68.68,39.72,35.83,28.65,26.37,25.82,24.26,22.53,17.10,14.28ppm。ESI-MS m/z=683[M+Na]+。
实例2:用环己醇缩合四(羟甲基)甘脲
向悬浮于环己醇(20.0当量)中的四(羟甲基)甘脲(1.0当量)中添加浓硝酸(4.4当量)。此混合物经加热以溶解甘脲,接着在高温下搅拌直到反应完成。最终反应混合物冷却到环境温度,用稀苛性碱中和,经硫酸镁干燥,接着通过旋转蒸发来浓缩。最终产物通过从粗反应混合物结晶或通过经由柱色谱(EtOAc:Hex)纯化而分离,得到白色结晶固体状的目标化合物。
实例3:用甘脲偶合氯甲基环己醚
向溶解于四氢呋喃中的甘脲(1.0当量)中添加氯甲基环己醚(4.4当量)和稀氢氧化钠(8.8当量)。在高温下搅拌此溶液直到完成。所得溶液用二氯甲烷萃取,经硫酸镁干燥,且通过旋转蒸发来浓缩。最终产物通过结晶或柱色谱(EtOAc:Hex)分离,得到白色结晶固体状的目标化合物。
实例4:用四(氯甲基)甘脲偶合环己醇
溶解于四氢呋喃中的四(氯甲基)甘脲(1.0当量)缓慢添加到保持于0C下的环己醇(4.4当量)和氢化钠(8.8当量)于四氢呋喃中的溶液中。所得反应混合物加热到60C且使其搅拌过夜。所得溶液冷却到0C且通过小心地添加水淬灭。所得混合物用二氯甲烷萃取,经硫酸镁干燥,且通过旋转蒸发来浓缩。最终产物通过结晶或柱色谱(EtOAc:Hex)分离,得到白色结晶固体状的目标化合物。
实例5:用四(乙酰氧基甲基)甘脲偶合环己醇
溶解于四氢呋喃中的四(乙酰氧基甲基)甘脲(1.0当量)缓慢添加到保持于0℃下的环己醇(4.4当量)和氢化钠(8.8当量)于四氢呋喃中的溶液中。所得反应混合物加热到60℃且使其搅拌过夜。所得溶液冷却到0℃且通过小心地添加水淬灭。所得混合物用二氯甲烷萃取,经硫酸镁干燥,且通过旋转蒸发来浓缩。最终产物通过结晶或柱色谱(EtOAc:Hex)分离,得到白色结晶固体状的目标化合物。
实例6:合成四(正己基)甘脲
含1,3,4,6-四(羟甲基)四氢咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(1g,3.8mmol)的2ml DMSO经溶解。接着,0.15ml硝酸(65%)和正己醇(9.5ml,76.3mmol)添加至溶液且混合物在60℃下加热16小时。在反应结束之后,反应液体经冷却且添加约pH 7下的1N NaOH。约100ml乙酸乙酯用于萃取混合物且有机相通过饱和NaCl(水性)溶液洗涤2次。在经Na2SO4干燥之后,去除溶剂。粗化合物通过快速色谱(庚烷/EtOAc)纯化。获得产量(%)为0.15g的无色粘滞油产物,1H NMR(600MHz,DMSO-d6):δppm)5.50(s,2H),4.73(m,8H),3.36(m,8H),1.46(m,8H),1.24(m,26H),0.85(t,12H)。
实例7:合成四(正丁基)甘脲
含1,3,4,6-四(羟甲基)四氢咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(1.88g,7.2mmol)的1.5ml DMSO经溶解。接着,0.15ml硝酸(65%)和n-BuOH(13.12ml,143mmol)添加至溶液且混合物在60℃下加热16小时。在反应结束之后,反应液体经冷却且添加约pH 7下的1N NaOH。约100ml乙酸乙酯用于萃取混合物且有机相通过饱和NaCl(水性)溶液洗涤2次。在经Na2SO4干燥之后,去除溶剂。粗化合物通过快速色谱(庚烷/EtOAc)纯化。获得产量(11%)为0.38g的无色粘滞油产物,1H NMR(600MHz,DMSO-d6):δ(ppm)5.52(s,2H),4.73(m,8H),3.35(m,8H),1.46(m,8H),1.29(m,8H),0.85(t,12H)。
实例8:合成四(四氢-4-吡喃醇)甘脲
含1,3,4,6-四(羟甲基)四氢咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(3g,11.4mmol)的四氢-4-吡喃醇(11ml,114mmol)经溶解。接着,0.15ml硝酸(65%)添加到溶液中且混合物在60℃下加热16小时。在反应结束之后,反应液体经冷却且添加约pH 7下的1NNaOH。约100ml乙酸乙酯用于萃取混合物且有机相通过饱和NaCl(水性)溶液洗涤2次。在经Na2SO4干燥之后,去除溶剂。粗化合物通过快速色谱(MC/丙酮)纯化。获得无色粘滞油产物。1H NMR(600MHz,DMSO-d6):δ(ppm)5.57(s,2H),4.84(m,8H),3.78(m,8H),3.57(m,4H),3.29(m,8H),1.82(m,8H),1.40(m,8H)。
实例9:合成四(4-乙基环己醇)甘脲
含1,3,4,6-四(羟甲基)四氢咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(1.99g,7.6mmol)的1.5ml DMSO经溶解。接着,0.3ml硝酸(65%)和4-乙基环己醇(10.5ml,75.9mmol)添加至溶液且混合物在60℃下加热16小时。在反应结束之后,反应液体经冷却且添加约pH 7下的1N NaOH。约100ml乙酸乙酯用于萃取混合物且有机相通过饱和NaCl(水性)溶液洗涤2次。在经Na2SO4干燥之后,去除溶剂。
实例10:合成四(4-甲基环己醇)甘脲
含1,3,4,6-四(羟甲基)四氢咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(1.25g,4.8mmol)的3ml DMSO经溶解。接着,0.3ml硝酸(65%)和4-甲基环己醇(5.9ml,47.7mmol)添加至溶液中且混合物在60C下加热16小时。在反应结束之后,反应液体经冷却且添加约pH 7下的1N NaOH。约100ml乙酸乙酯用于萃取混合物且有机相通过饱和NaCl(水性)溶液洗涤2次。在经Na2SO4干燥之后,去除溶剂。
实例11:通过TGA热降解交联剂
此实例显示本发明交联剂分子的增加的热降解特性(如对应于其热解重量分析(TGA)分解概况)。
如本文中所提及,样品材料(确切地说交联剂化合物)的热解重量分析(TGA)分解温度通过以下方案测定。热解重量分析(TGA)分解温度通过在温度不断升高时用质谱测量测试样品的质量变化而测定。随着温度增加,测量样品的重量变化。记录到50%质量损失的温度测定为材料的分解温度。可商购的(如PerkinElmer)热解重量分析设备可用于所述测定。
测量表1中示出的以下交联剂的TGA分解温度。如表1中所示,四(环己氧基甲基)甘脲(TcyGU)具有最高分解温度且接着分别为四(正己氧基)-(TnhyGU)、四(正丁氧基甲基)-(TnbGU)、四(苯氧基甲基)-(TPhmGU)、四(异丙氧基甲基)-(TisoproGU)和四(甲氧基甲基)-(TMGU)衍生物。这些交联剂化合物的结构如下:
TMGU | TisoproGU | TPhmGU | TnbuGU | TnhGU | TcyGU | |
温度(℃) | 231.08 | 213.85 | 224.74 | 257.08 | 304.44 | 332.84 |
表1
实例12.缓慢热酸产生剂调配物的剥离/膨胀结果
此实例显示重链交联剂(TcyGU)在热烘烤期间形成BARC中的有效性。已知对照化合物四(甲氧基甲基)甘脲(TMGU)在高热烘烤温度(例如205℃)期间汽化并且因此给出高剥离/膨胀值,其指示在后续处理步骤中在水性条件下产生具有高溶解性的不佳膜。本发明重链交联剂TcyGU在这些温度下不汽化且作为交联剂极活跃,因此所得BARC膜不在后续水性处理步骤下溶解且给出低剥离/膨胀值。作为比较,评估交联剂MiPGU和MP-TMGU且不充当这些方法条件下的有效交联剂且提供极差剥离/膨胀值。
制备抗反射组合物
0.23g TMGU(下表2中的实例F1)或TcyGU(下表2中的实例F2)或MiPGU(下表2中的实例F3)或MP-TMGU(下表2中的实例F4)、0.006g p-TSA苄基铵盐、0.001g来自OMNOVAsolutions Inc.的氟化物表面活性剂Polyfox 656、0.53g基于异氰尿酸酯的聚酯COP-BTTB(韩国Chemoptics,Mw=3K,PDI=1.4)和19.2g 2-羟基异丁酸甲酯(HBM)经混合,获得按组合物的总重量计的3.8重量%溶液。溶液经由具有0.45微米孔径的PTFE微过滤器过滤,获得BARC组合物。通过将0.23g TMGU、0.006g p-TSA铵盐、0.001g来自OMNOVA solutions Inc.的氟化物表面活性剂Polyfox 656、0.53g基于异氰尿酸酯的聚酯树脂COP-BTTB(韩国Chemoptics,Mw=3K,PDI=1.4)和19.2g 2-羟基异丁酸甲酯(HBM)(实例C1)混合制备一种比较调配物。
测量耐溶剂性(膨胀/剥离)的程序
测试耐溶剂性的各样品溶液旋涂到Si晶片上且在205C下烘烤60秒。使用椭圆对称法测量Si晶片上的膜厚度(下表的涂布列的THK)。通常用于光致抗蚀剂领域中的PGME/PGMEA=70:30重量%混合溶液接着倾倒于BARC膜的表面上且使其静置90秒。晶片接着以4000rpm旋干60秒。再次测量厚度(下表的剥离列的THK)且在110C下额外烘烤60秒之后再一次测量最终厚度(下表的烘烤列的THK)。最终烘烤与旋干之间的差异报导为膨胀值且与初始厚度的差异报导为剥离值。
表2
实例13:含有各种x-连接剂的BARC薄膜的升华结果
此实例显示205℃的QCM烘烤温度下的来自实例12的三种性能最佳化合物的所展现脱气厚度。对照化合物TMGU具有高脱气厚度,其为导致上文实例12中的不佳性能的原因。本发明化合物TcyGU给出极低脱气厚度,其为导致实例12中的优良性能的原因。性能最佳比较化合物MP-TMGU给出工作脱气厚度值且贡献于上文实例12中的不佳结果。
制备用于升华测试的抗反射组合物
将0.23g TMGU(下表3中的实例F5)或TcyGU(下表3中的实例F6)或MP-TMGU(下表3中的实例F7)、0.001g来自OMNOVA solutions Inc.的氟化物表面活性剂Polyfox 656、0.53g基于异氰尿酸酯的聚酯COP-BTTB(韩国Chemoptics,Mw=3K,PDI=1.4)和19.2g 2-羟基异丁酸甲酯(HBM)混合,获得按组合物的总重量计的3.8重量%溶液。溶液经由具有0.45微米孔径的PTFE微过滤器过滤,获得无热酸产生剂的BARC组合物以避免对升华结果的交联效应。
测量升华的一般程序
石英晶体微天平(QCM)用于测定升华含量。
测试升华的每一样品溶液旋涂到Si晶片上且在使晶片与石英晶体样品固持器几乎直接接触的特殊热板上在205C下烘烤。通过频率计数器测量b/a频率且转化成QCM板中升华的材料的厚度测定。
表3
实例14.光刻
此实例显示当光致抗蚀剂置于含有交联剂且在低温下处理的所得BARC材料顶部上时,本发明重链交联剂TcyGU产生与参考化合物TMGU相当的结果。此证实重链交联剂对于这些和其它应用的效用。
实例F1和C1的BARC组合物各自以1500rpm旋涂于150mm硅晶片上,接着使用TELMark 8晶片涂层轨道机在205℃下烘烤60秒。烘烤之后的BARC涂层厚度为 陶氏(Dow)UVTM1610DUV光致抗蚀剂旋涂于BARC涂层的顶部上且在100℃下烘烤60秒,得到240nm厚光致抗蚀剂层。随后使用248nm KrF晶片步进机在0.65NA下通过目标掩模对光致抗蚀剂进行曝光。接下来,在120℃下对光致抗蚀剂层进行60秒的曝光后烘烤,然后使用陶氏MFTMCD-26TMAH显影剂以标准60秒单搅炼工艺进行显影。通过扫描电子显微术进行图案的临界尺寸的检验以检查每一BARC上的光致抗蚀剂的图案崩溃容限。
Claims (10)
2.根据权利要求1所述的方法,其中所述交联剂组分具有至少400道尔顿的分子量。
3.根据权利要求1或2所述的方法,其中所述交联剂组分具有小于1500道尔顿的分子量。
4.根据权利要求1到3中任一项所述的方法,其中所述交联剂组分具有大于250℃的降解温度。
5.根据权利要求1到4中任一项所述的方法,其中一或多个R基团包含任选经取代的碳脂环族部分。
6.根据权利要求1到5中任一项所述的方法,其中所述光致抗蚀剂组合物用活化辐射成像且所述成像的光致抗蚀剂组合物层经显影,得到光致抗蚀剂浮雕图像。
7.根据权利要求1到6中任一项所述的方法,其中所述涂料组合物层在涂覆所述光致抗蚀剂组合物层之前经热处理。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101017326A (zh) * | 2006-01-29 | 2007-08-15 | 罗门哈斯电子材料有限公司 | 与外涂的光致抗蚀剂一起使用的涂料组合物 |
CN102575127A (zh) * | 2009-10-30 | 2012-07-11 | Az电子材料美国公司 | 抗反射光致抗蚀剂组合物 |
CN103370653A (zh) * | 2011-02-08 | 2013-10-23 | Az电子材料美国公司 | 底层涂料组合物及制造微电子器件的方法 |
Family Cites Families (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1089145A (en) * | 1976-02-02 | 1980-11-04 | Girish G. Parekh | Organic metal finishes |
EP1172695A1 (en) * | 2000-07-14 | 2002-01-16 | Shipley Company LLC | Barrier layer |
DE60330798D1 (de) * | 2002-10-09 | 2010-02-11 | Nissan Chemical Ind Ltd | Zusammensetzung zur bildung einer antireflexschicht für die lithographie |
JP4244315B2 (ja) * | 2002-12-02 | 2009-03-25 | 東京応化工業株式会社 | レジストパターン形成用材料 |
US7030201B2 (en) * | 2003-11-26 | 2006-04-18 | Az Electronic Materials Usa Corp. | Bottom antireflective coatings |
JP4612672B2 (ja) | 2004-03-12 | 2011-01-12 | フジフィルム・エレクトロニック・マテリアルズ・ユーエスエイ・インコーポレイテッド | リソグラフィ用途のための熱硬化性アンダーコート |
US7691556B2 (en) | 2004-09-15 | 2010-04-06 | Az Electronic Materials Usa Corp. | Antireflective compositions for photoresists |
US20070026458A1 (en) | 2004-12-17 | 2007-02-01 | Entelos, Inc. | Assessing insulin resistance using biomarkers |
JP4478589B2 (ja) * | 2005-02-02 | 2010-06-09 | 富士フイルム株式会社 | ネガ型レジスト組成物及びそれを用いたパターン形成方法 |
EP1705519B1 (en) | 2005-03-20 | 2016-07-06 | Rohm and Haas Electronic Materials, L.L.C. | Method of treating a microelectronic substrate |
JP4815307B2 (ja) * | 2005-08-29 | 2011-11-16 | 富士フイルム株式会社 | 光学フィルム、反射防止フィルム、その製造方法、並びにそれを用いた偏光板、およびディスプレイ装置 |
JP5014822B2 (ja) * | 2006-02-13 | 2012-08-29 | Hoya株式会社 | マスクブランク用レジスト下層膜形成組成物、マスクブランク及びマスク |
HUE038015T2 (hu) * | 2006-03-30 | 2018-09-28 | Fmc Corp | Acetilén karbamid származék-polikarbamid polimerek, és ezek mikrokapszulái és kiszerelései szabályozott kibocsátáshoz |
US7638262B2 (en) | 2006-08-10 | 2009-12-29 | Az Electronic Materials Usa Corp. | Antireflective composition for photoresists |
KR20170067906A (ko) | 2006-10-03 | 2017-06-16 | 라디우스 헬쓰, 인코포레이티드 | 골 아나볼릭 단백질을 위한 약물 전달 방법 |
US7824844B2 (en) | 2007-01-19 | 2010-11-02 | Az Electronic Materials Usa Corp. | Solvent mixtures for antireflective coating compositions for photoresists |
US7727705B2 (en) * | 2007-02-23 | 2010-06-01 | Fujifilm Electronic Materials, U.S.A., Inc. | High etch resistant underlayer compositions for multilayer lithographic processes |
CN101641390B (zh) * | 2007-04-02 | 2013-05-01 | 第一毛织株式会社 | 具有抗反射性能的硬掩模组合物及用其图案化材料的方法 |
US20080286689A1 (en) * | 2007-05-14 | 2008-11-20 | Hong Zhuang | Antireflective Coating Compositions |
US8334338B2 (en) | 2007-05-23 | 2012-12-18 | Jsr Corporation | Composition for forming resist lower layer film |
US7709370B2 (en) * | 2007-09-20 | 2010-05-04 | International Business Machines Corporation | Spin-on antireflective coating for integration of patternable dielectric materials and interconnect structures |
CN101821677B (zh) * | 2007-10-31 | 2012-07-04 | 日产化学工业株式会社 | 形成抗蚀剂下层膜的组合物和采用该形成抗蚀剂下层膜的组合物形成抗蚀剂图案的方法 |
JP5077026B2 (ja) * | 2008-04-02 | 2012-11-21 | Jsr株式会社 | レジスト下層膜形成用組成物及びそれを用いたデュアルダマシン構造の形成方法 |
US8158338B2 (en) | 2008-07-08 | 2012-04-17 | Massachusetts Institute Of Technology | Resist sensitizer |
US20100092894A1 (en) | 2008-10-14 | 2010-04-15 | Weihong Liu | Bottom Antireflective Coating Compositions |
JP5335375B2 (ja) * | 2008-10-31 | 2013-11-06 | キヤノン株式会社 | 画像表示装置 |
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 |
KR101311942B1 (ko) * | 2009-12-31 | 2013-09-26 | 제일모직주식회사 | 레지스트 하층막용 방향족 고리 함유 화합물 및 이를 포함하는 레지스트 하층막용 조성물 |
KR101344794B1 (ko) * | 2009-12-31 | 2014-01-16 | 제일모직주식회사 | 레지스트 하층막용 방향족 고리 함유 중합체 및 이를 포함하는 레지스트 하층막 조성물 |
JP2012133289A (ja) * | 2010-12-24 | 2012-07-12 | Sumitomo Chemical Co Ltd | レジストパターンの製造方法 |
SG11201401430RA (en) * | 2011-10-10 | 2014-09-26 | Brewer Science Inc | Spin-on carbon compositions for lithographic processing |
US8932796B2 (en) * | 2011-11-10 | 2015-01-13 | International Business Machines Corporation | Hybrid photoresist composition and pattern forming method using thereof |
US9041116B2 (en) | 2012-05-23 | 2015-05-26 | International Business Machines Corporation | Structure and method to modulate threshold voltage for high-K metal gate field effect transistors (FETs) |
JP5894106B2 (ja) * | 2012-06-18 | 2016-03-23 | 信越化学工業株式会社 | レジスト下層膜形成用化合物、これを用いたレジスト下層膜材料、レジスト下層膜形成方法、パターン形成方法 |
US10017664B2 (en) | 2013-05-13 | 2018-07-10 | Nissan Chemical Industries, Ltd. | Novolac resin-containing resist underlayer film-forming composition using bisphenol aldehyde |
JP6255906B2 (ja) * | 2013-10-31 | 2018-01-10 | Jsr株式会社 | 感放射線性樹脂組成物及びネガ型レジストパターン形成方法 |
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CN102575127A (zh) * | 2009-10-30 | 2012-07-11 | Az电子材料美国公司 | 抗反射光致抗蚀剂组合物 |
CN103370653A (zh) * | 2011-02-08 | 2013-10-23 | Az电子材料美国公司 | 底层涂料组合物及制造微电子器件的方法 |
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TWI659991B (zh) | 2019-05-21 |
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KR102414899B1 (ko) | 2022-06-30 |
JP6525376B2 (ja) | 2019-06-05 |
US10788751B2 (en) | 2020-09-29 |
US20170059991A1 (en) | 2017-03-02 |
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