CN109541886B - 抗反射组合物及其使用方法和经涂布衬底 - Google Patents

抗反射组合物及其使用方法和经涂布衬底 Download PDF

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CN109541886B
CN109541886B CN201811018471.XA CN201811018471A CN109541886B CN 109541886 B CN109541886 B CN 109541886B CN 201811018471 A CN201811018471 A CN 201811018471A CN 109541886 B CN109541886 B CN 109541886B
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photoresist
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CN109541886A (zh
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李晶真
林载峰
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Rohm and Haas Electronic Materials Korea Ltd
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Abstract

提供新型方法和衬底，其包括含有一种或多种热酸产生剂的抗反射组合物。

Description

抗反射组合物及其使用方法和经涂布衬底
技术领域
本发明涉及新型方法和衬底，其包括含有一种或多种热酸产生剂的抗反射组合物。
背景技术
光致抗蚀剂是用于将图像转移到衬底上的感光膜。其形成负像或正像。在将光致抗蚀剂涂布在衬底上之后，经由图案化光掩模使涂层曝光于活化能来源(如紫外光)，以在光致抗蚀剂涂层中形成潜像。光掩模具有对活化辐射不透明和透明的区域，其界定需要转移到底层衬底的图像。通过使抗蚀剂涂层中的潜像图案显影来提供浮雕图像。
已知光致抗蚀剂可以提供分辨率和尺寸足以用于许多现有商业应用的特征。然而，对于许多其它应用，需要可以提供亚微米级尺寸的高分辨率图像的新型光致抗蚀剂和相关材料以及工艺。
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使光致抗蚀剂中的辐射强度产生空间变化，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非所意图曝光的区域中，再次导致线宽变化。散射和反射的量通常在不同区域之间变化，导致进一步的线宽非均一性。衬底形貌的变化也会引起分辨率受限问题。
用于减少反射辐射问题的一种方法为使用插在衬底表面与光致抗蚀剂涂层之间的辐射吸收层。此类层也被称为抗反射层或抗反射组合物。参见US 9541834；US20150212414；US6767689B2；US6887648B2；和US8623589。
将期望具有与外涂光致抗蚀剂组合物一起使用的新型抗反射涂料组合物。
发明内容
现已发现新型方法，其包括使用包含树脂组分和一种或多种热酸产生剂化合物的抗反射组合物。将光致抗蚀剂涂覆在本发明抗反射组合物的涂层上。
还提供新型抗反射涂料组合物，其用于外涂光致抗蚀剂组合物层。
特别提供的底层抗反射组合物可以表现出增强的涂层特性。优选的抗反射组合物也可在相对较低的温度下硬化或交联。例如，参见下面的比较结果。
已经发现，使用相对亲水的聚合物，如聚酯树脂，或包含异氰尿酸酯单元的树脂，或含有异氰尿酸酯取代的聚酯树脂，可以在外涂的光致抗蚀剂层的光刻处理中减少缺陷。然而，还发现，使用这种亲水性聚合物会损害抗反射组合物在底层衬底，如微电子晶片上的涂层覆盖，包括由于亲水性聚合物的非所期望的聚集，因为抗反射组合物层经热处理而在涂覆外涂光致抗蚀剂层之前交联或以其它方式硬化组合物层。
现已发现，本发明的抗反射组合物可以在相对较低的温度下进行交联或其它硬化(例如55℃、60℃、65℃或70℃，持续30或60秒)。由于这种降低的硬化温度(起始温度)，已发现硬化的抗反射组合物层的涂层质量得到改善，包括包含亲水性树脂组分的抗反射组合物。在不受任何理论束缚的情况下，改善的涂层质量可能是由热处理过程中组合物树脂组分的聚集减少引起。
更具体地说，在一个优选方面，提供一种包含以下的方法：
a)在衬底上涂覆一层涂料组合物，所述涂料组合物包含：1)树脂；和2)包含式(I)结构的热酸产生剂：
Figure GDA0003435279300000021
其中Y具有式(II)结构：
Figure GDA0003435279300000022
每个R1独立地为CN、NO2、F、Cl、Br、I或CF3；n是1到5的整数；并且X是有机或无机阴离子组分；和
b)在所述涂料组合物层上涂覆一层光致抗蚀剂组合物。
可以采用各种阴离子X组分，其包括有机和无机组分，通常优选有机组分，如甲苯磺酸酯。在某些方面，优选的R1基团包括CN、NO2、Cl、Br、I和CF3。在另外的方面，优选的R1基团可以是CN、NO2和CF3。
本发明优选的涂料组合物还可以包含单独的交联剂组分。这种交联剂可以与树脂组分反应，如在组合物的涂层热处理过程中，在其上涂覆光致抗蚀剂层之前。
各种树脂可用于本发明的底层涂料组合物中。在某些实施例中，亲水性树脂是优选的，如聚酯树脂，包含氰尿酸酯取代的树脂，包括包含氰尿酸酯取代的聚酯树脂。优选地，在这样的组合物中，一种或多种亲水性树脂占涂料组合物的总树脂含量的至少50重量％，更优选一种或多种亲水性树脂占涂料组合物的总树脂含量的至少60、70、80、90、95或甚至100重量％。
在与外涂光致抗蚀剂一起使用时，涂料组合物可涂覆于衬底上，如上面可具有一个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之前经热处理。如所提及，此类热处理可引起涂料组合物层硬化，包括交联。此类交联可包括硬化和/或一种或多种组合物组分之间的共价键形成反应并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使涂覆的光致抗蚀剂组合物层成像，并且使成像的光致抗蚀剂组合物层显影，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)。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，其含有一种或多种光敏化合物和含有在存在光生酸的情况下经历去封闭或裂解反应的单元的树脂组分。
本发明进一步提供涂布有单独或与光致抗蚀剂组合物组合的本发明涂料组合物的衬底(如微电子晶片衬底)。
进一步提供与外涂光致抗蚀剂层一起使用的新型抗反射涂料组合物。优选的抗反射组合物包含1)树脂；和2)包含式(IA)结构的热酸产生剂：
Figure GDA0003435279300000031
其中Y具有式(IIA)结构：
Figure GDA0003435279300000032
每个R1独立地为C1-C6卤烷基，如CF3、-CN、-NO2、-COR2、-COOR2、-CONR2或-SO2R2；
R2独立地为氢、C1-C6烷基、C3-C6环烷基或苯基，其可任选地被取代；n是1到5的整数；并且X是有机或无机阴离子组分。优选的式IIA的R1基团包括-CF3、-CN和-NO2、乙酰基和酯。优选的酯R1基团在光刻处理期间(例如在外涂光致抗蚀剂层的成像的热处理期间)将不具有反应性(例如将不经历或将显著地经历键断裂反应)。优选的X基团是有机组分，如甲苯磺酸酯等。
本发明的其它方面论述于下文中。
具体实施方式
在一个优选的方面，提供与外涂光致抗蚀剂组合物一起使用的抗反射组合物，其中所述抗反射组合物包含1)树脂；和2)包含式(I)结构的热酸产生剂：
Figure GDA0003435279300000041
其中Y具有式(IIB)结构：
Figure GDA0003435279300000042
每个R1独立地为卤素、C1-C6卤烷基、-CN、-NO2、-COR2、-COOR2、-CONR2或-SO2R2；
R2独立地为氢、C1-C6烷基、C3-C6环烷基或苯基，其可任选地被取代；
n是0到5的整数；并且
X是有机或无机阴离子组分。
在某些优选的方面，R1是氟烷基，如-CF3。在优选的实施例中，如上文所论述，每个R1独立地为CN、NO2、F、Cl、Br、I或CF3，或每个R1独立地为CN、NO2、Cl、Br、I或CF3。各种阴离子X组分适用于有机组分，如通常优选的甲苯磺酸酯。
在某些实施例中，热酸产生剂的阳离子组分不含氟作为环取代基。在某些实施例中，热酸产生剂的阳离子组分不含任何氟含量。在某些实施例中，热酸产生剂的阳离子组分不含任何卤素含量。
用于本发明抗反射组合物的优选热酸产生剂化合物可具有下式(A)，(B)或(C)结构：
Figure GDA0003435279300000043
Figure GDA0003435279300000051
其中在那些式(A)、(B)或(C)中的每一个中，R1是卤素、C1-C6卤烷基、-CN、-NO2、-COR2、-COOR2、-CONR2或-SO2R2；并且在式(A)、(B)或(C)的某些优选实施例中，R1为CN、NO2、F、Cl、Br、I或CF3，并且在式(A)、(B)或(C)的更进一步优选的实施例中，R1为CN、NO2、Cl、Br、I或CF3，或R1为CN、NO2或CF3。
用于本发明抗反射组合物的特别优选的热酸产生剂包括以下物质。还优选的是以下热酸产生剂，其含有下面描述的经取代的吡啶基阳离子组分，但与除所示的甲苯磺酸酯之外的阴离子组分络合：
Figure GDA0003435279300000052
Figure GDA0003435279300000061
用于本发明抗反射组合物的尤其优选的热酸产生剂包括以下物质。还优选的是以下热酸产生剂，其含有下面描述的经取代的吡啶基阳离子组分，但与除所示的甲苯磺酸酯之外的阴离子组分络合。
Figure GDA0003435279300000071
Figure GDA0003435279300000081
有利地，在某些实施例中，所述热酸产生剂具有不超过约100℃、或不超过约90℃、或不超过约80℃、或不超过约70℃、或不超过约60℃的起始温度(即热产生酸时所处的温度)。
如本文所提及，热酸产生剂的起始温度通过在选定温度下对含有热酸产生剂的旋涂组合物膜层进行热处理持续60秒来确定，其中厚度测量值由以下得到：(i)初始旋涂的组合物膜层，其在选定的温度下进行热处理，和(i i)经有机溶剂(例如50:50v/v 2-羟基异丁酸甲酯(HBM):丙二醇甲醚乙酸酯(PGMEA)的有机溶剂)剥离后的组合物膜层。起始温度是交联膜的最低温度，并且与最终膜厚度相比，热处理后评估的含有热酸产生剂的组合物膜层的厚度减少至少10％。参见实例9的示例性方案。
优选的TAG具有相对较低的分子量，例如分子量小于或等于3000，更优选≤2500、≤2000、≤1500、≤1000、≤800或甚至更优选≤500。
通常，一种或多种热酸产生剂以组合物的总干燥组分(除了溶剂载剂外的所有组分)的约0.1到10重量％，更优选地，总干燥组分的约0.5到2重量％的浓度存在于涂料组合物中。
本发明的热酸产生剂可容易制备。例如，经取代的吡啶基化合物可以与阴离子组分混合(例如对于甲苯磺酰基阴离子组分，4-甲基苯磺酸水合物可以与经取代的吡啶基化合物混合)。参见例如以下实例2-4。
本发明的涂料组合物的尤其优选的树脂可包含聚酯键。聚酯树脂可以通过一种或多种多元醇试剂与一种或多种含羧基(如羧酸、酯、酐等)化合物进行反应而容易制备。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。
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10,000道尔顿的重均分子量(Mw)和约500到约1,000,000道尔顿的数均分子量(Mn)。本发明组合物的树脂的分子量(Mw或Mn)宜通过凝胶渗透色谱法测定。
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，一或树脂可宜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或85到95、98或99+(或甚至100)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物质。
用于本发明底层涂料组合物的特别优选的树脂包括含有下列重复单元的那些树脂：
Figure GDA0003435279300000101
可以容易制备用于本发明底层抗反射组合物的合适和优选的树脂。参见，例如以下实例1，其中详述了异氰尿酸酯试剂与二醇化合物反应以提供聚酯氰尿酸酯树脂。
如上所论述，在某些实施例中，本发明的涂料组合物除树脂之外或作为树脂的组分可包含交联剂。举例来说，涂料组合物可包括胺基交联剂，如三聚氰胺物质，其包括三聚氰胺树脂，如由氰特工业(Cytec Industries)制造且以商品名Cymel 300、301、303、350、370、380、1116和1130销售的树脂；甘脲，其包括购自氰特工业的那些甘脲；和基于苯并三聚氰胺(benzoquanamine)和脲的物质，其包括树脂，如以名称Cymel 1123和1125购自氰特工业的苯并三聚氰胺树脂和以名称Powderlink 1174和1196购自氰特工业的脲树脂。除可商购以外，此类胺基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共聚来制备。
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光致抗蚀剂层的辐射的另外染料化合物。其它任选的添加剂包括表面调平剂，例如可以商品名Silwet 7604购得的调平剂，或购自3M公司的表面活性剂FC 171或FC 431。
本发明的底层涂料组合物还可含有其它物质，如光酸产生剂，其包括如所论述的与外涂光致抗蚀剂组合物一起使用的光酸产生剂。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。
为了制造液态底层涂料组合物，将涂料组合物的组分溶解于适合溶剂中，如一种或多种氧基异丁酸酯，尤其为甲基-2-羟基异丁酸酯、乳酸乙酯或如2-甲氧基乙醚(二乙二醇二甲醚(diglyme))、乙二醇单甲醚和丙二醇单甲醚的二醇醚中的一种或多种；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。
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种或多种酸产生剂。一般优选的是正型抗蚀剂并且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香族基(如包括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(包括酚)的聚合物尤其适用于多种抗蚀剂系统，包括用EUV和电子束辐射成像的那些抗蚀剂系统。对于正性作用抗蚀剂，聚合物还优选地含有一个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香族基的聚合物的情况下，聚合物可包含含有一个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。此类单体可以与一种或多种包含芳香族基(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(I)的酸不稳定单体，含内酯单体(II)和下式(III)的极性控制单体，或包含前述单体中的至少一种的组合：
Figure GDA0003435279300000121
其中每个R1独立地为H、F、-CN、C1-6烷基或C1-6氟烷基。在式(I)的可酸脱保护的单体中，R2独立地为C1-20烷基、C3-20环烷基或C6-20芳基，并且每个R2是分开的或至少一个R2键合到相邻的R2而形成环状结构。在式(II)的含内酯单体中，L1为单环、多环或稠合多环C4-20含内酯基团。
通式(I)的单元包括酸不稳定基团，其在暴露于活化辐射和热处理时经历光致酸促进的脱保护反应。这允许改变基质聚合物的极性，导致聚合物和光致抗蚀剂组合物在有机显影剂中的溶解度发生变化。用于形成式(I)单元的合适单体包括例如以下：
Figure GDA0003435279300000131
或包含前述单体中的至少一种的组合，其中R1为H、F、-CN、C1-6烷基或C1-6氟烷基。
通式(II)的单元包括有效控制基质聚合物和光致抗蚀剂组合物的溶解速率的内酯部分。用于形成通式(II)单元的合适单体包括例如以下：
Figure GDA0003435279300000132
或包含前述单体中的至少一种的组合，其中R1为H、F、-CN、C1-6烷基或C1-6氟烷基。
式(III)单元提供极性基团，其增强树脂和光致抗蚀剂组合物的抗蚀刻性，并提供控制树脂和光致抗蚀剂组合物的溶解速率的另外手段。用于形成式(III)单元的单体包括甲基丙烯酸3-羟基-1-金刚烷酯(HAMA)，优选丙烯酸3-羟基-1-金刚烷酯(HADA)。
树脂可包括一种或多种不同于第一单元的通式(I)、(II)和/或(III)的另外单元。当树脂中存在另外的此类单元时，其优选包括另外的含离去基团的式(I)单元和/或含内酯的式(II)单元。
除了上述聚合单元之外，树脂还可包括一种或多种不具有通式(I)、(II)或(III)的另外单元。例如，特别合适的含内酯基的单元具有以下通式(IV)：
Figure GDA0003435279300000141
其中：R1为H、F、-CN、C1-6烷基或C1-6氟烷基、杂环烷基，R3为(C1-C3)亚烷基，并且L2为内酯基。以下示例性单体适用于形成通式(IV)的另外的内酯单元：
Figure GDA0003435279300000142
或包含前述单体中的至少一种的组合，其中R1为H、F、-CN、C1-6烷基或C1-6氟烷基。
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的去封闭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，特别是丙烯酸烷酯酸不稳定基团的单元的三元共聚物和其它共聚物)中。
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、交联或硬化的物质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(如酚系或非芳香族聚合物)、交联剂组分和本发明的光敏组分。此类组合物和其用途已经公开于Thackeray等人的欧洲专利申请0164248和美国专利第5,128,232号中。用作聚合物粘合剂组分的优选酚系聚合物包括酚醛清漆和聚(乙烯基苯酚)，如上文所论述的那些组分。优选的交联剂包括胺基物质，包括三聚氰胺、甘脲、苯并胍胺基物质和脲基物质。三聚氰胺-甲醛聚合物通常尤其合适。此类交联剂为可商购的，例如三聚氰胺聚合物、甘脲聚合物、脲基聚合物和苯并胍胺聚合物，如由氰特以商品名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，参见例如罗门哈斯电子材料(Rohm and Haas ElectronicMaterials)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-对甲苯磺酸盐和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)苯和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)-1,3,5-三嗪和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物质。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、速度促进剂和敏化剂。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。示例性淬灭剂包括胺，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，并且优选是非离子的。示例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公司购得的FC-4430和FC-4432表面活性剂；和氟二醇，如来自欧诺法(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用于溶解、施配和涂布光致抗蚀剂中所用组分的溶剂。示例性溶剂包括苯甲醚；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；以及包含前述溶剂中的至少一种的组合。
光刻处理
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。衬底宜为任何用于涉及光致抗蚀剂的工艺中的衬底。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。还宜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之前固化。固化条件将随着底层涂料组合物的组分而有所变化。确切地说，固化温度将取决于涂料组合物中所用的特定酸或酸(热)产生剂。典型固化条件为约60℃到225℃下持续约0.5到5分钟。已经发现，如本文中所公开的优选抗反射组合物的涂层可以有效地经受在相对较低的温度，例如55℃或60℃-75℃下硬化。固化条件优选地使得涂料组合物涂层基本上不溶于所用的光致抗蚀剂溶剂以及显影剂溶液。
在此类固化之后，将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为止。最优地，应基本上不出现底部组合物层与外涂光致抗蚀剂层的互混。
抗蚀剂层接着以常规方式通过掩模用活化辐射，如248nm、193nm或EUV辐射成像。曝光能量足以有效地活化抗蚀剂系统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并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与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，并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保护反应。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系统中，即其中曝光工具(尤其投影透镜)与光致抗蚀剂涂布的衬底之间的空间由浸没流体，如水或与一种或多种添加剂(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)已被加以处理以避免气泡，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)插入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(NTD)工艺中，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而选择性地去除。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工艺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氢氧化四烷基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，所述基团在脱保护时形成羧酸基和/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，其基于具有在脱保护时形成羧酸基的酸敏(可脱保护)基团的聚合物，并且显影剂优选地为不含金属离子的氢氧化四烷基铵溶液，如0.26N氢氧化四甲基铵水溶液。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衬底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体气体蚀刻，如氧等离子体蚀刻。等离子体气体蚀刻去除底层涂层。
如所论述，在某些方面，可以适当方式采用湿蚀刻工艺。湿蚀刻可适当地通过用湿蚀刻组合物暴露待蚀刻的表面(例如金属氮化物，或涂布有一个或多个有机层和/或无机层的金属氮化物)一定时间和温度以有效蚀刻表面(例如金属氮化物表面和/或其上的涂层)来进行。示例性的湿蚀刻组合物包括氢氧化铵和过氧化物，如过氧化氢的水性混合物，或酸，如硫酸和过氧化物，如过氧化氢的混合物。示例性组合物参见US2006/0226122。下面的实例还提供了示例性湿蚀刻工艺条件。如本文所提及，“湿蚀刻工艺”意指用流体组合物处理由邻接的光致抗蚀剂限定的衬底区域(在光致抗蚀剂图像的显影之后)，所述流体组合物通常为酸性或碱性的，与过氧化物试剂组合，但在任何情况下与等离子体干式蚀刻不同。
以下非限制性实例是对本发明的说明。
实例1：聚合物合成
Figure GDA0003435279300000181
如上述方案中所述制备具有结构1重复单元的树脂，如下所述。将250ml的3颈圆底烧瓶配备热电偶、迪安-斯塔克(Dean-stark)装置、冷凝器和加热油浴。将三(2-羟乙基)异氰尿酸酯(34.44g，131.8mmol)、三(2-羧乙基)异氰尿酸酯(45.50g，131.8mmol)、1,2-丙二醇(20.06g，263.7mmol)、对甲苯磺酸(p-TSA)(1.00g，5.3mmol)和34g苯甲醚称重到烧瓶中。其被加热到设定温度(150℃)并搅拌40分钟。然后将溶液冷却到室温。将冷却溶液用三乙胺(0.53g，5.3mmol)淬灭，并用HBM(80g)稀释以进行分离。用甲基叔丁基醚(MTBE)(800g)沉淀反应混合物，然后过滤并在40℃下真空干燥24小时。将3颈100ml圆底烧瓶配备热电偶、冷凝器和加热油浴。将预聚物(20g)、p-TSA(0.15g，0.79mmol)、1,3,4,6-四(丁氧基甲基)四氢咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮(11.4g，23.4mmol)和80g 2-羟基异丁酸甲酯(HBM)称重到烧瓶中并加热到设定温度(50℃)并搅拌4小时。用三乙胺(0.5mL)淬灭溶液。然后将溶液冷却到室温。用异丙醇(1000g)沉淀反应混合物，然后过滤并在40℃下真空干燥24小时。
实例2-4：热酸产生剂的合成
实例2：4-甲基苯磺酸3-氟吡啶-1-鎓的合成
将4-甲基苯磺酸水合物(75.0g，1.0当量)溶解于四氢呋喃(1500mL)中，并逐滴添加3-氟吡啶(40.2g，1.05当量)，同时在10～20℃下剧烈搅拌0.5小时。添加后，将反应混合物在室温下搅拌16小时。将其过滤并使用四氢呋喃(750mL)洗涤。将白色固体真空干燥。
实例3：4-甲基苯磺酸4-氟吡啶-1-鎓的合成
将4-甲基苯磺酸水合物(25.0g，1.0当量)溶解于四氢呋喃(500mL)中，并逐滴添加4-氟吡啶(13.4g，1.05当量)，同时在10～20℃下剧烈搅拌0.5小时。添加后，将反应混合物在室温下搅拌16小时。将其过滤并使用二乙醚(250mL)洗涤。将白色固体真空干燥。
实例4：4-甲基苯磺酸4-(三氟甲基)吡啶-1-鎓的合成.
将4-甲基苯磺酸水合物(6.0g，1.0当量)溶解于四氢呋喃(120mL)中，并逐滴添加4-(三氟甲基)吡啶(4.9g，1.05当量)，同时在10～20℃下剧烈搅拌0.5小时。添加后，将反应混合物在室温下搅拌16小时。将其过滤并使用二乙醚(60mL)洗涤。将白色固体真空干燥。
实例5-8：抗反射组合物的制备
实例5：
将0.863g聚合物(实例1)、0.027g作为交联剂的四甲氧基甲基甘脲和0.010g作为TAG的4-甲基苯磺酸3-氟吡啶-1-鎓盐(实例2)溶解于99.0g HBM溶剂中。
实例6：
将0.863g聚合物(实例1)、0.027g作为交联剂的四甲氧基甲基甘脲和0.010g作为TAG的4-甲基苯磺酸4-氟吡啶-1-鎓盐(实例3)溶解于99.0g HBM溶剂中。
实例7：
将0.860g聚合物(实例1)、0.027g作为交联剂的四甲氧基甲基甘脲和0.013g作为TAG的4-甲基苯磺酸4-(三氟甲基)吡啶-1-鎓盐(实例4)溶解于99.0g HBM溶剂中。
实例8：(比较)
将0.866g聚合物(实例1)、0.027g作为交联剂的四甲氧基甲基甘脲和0.007g作为TAG的4-甲基苯磺酸铵盐溶解于99.0g HBM溶剂中。
实例9：抗反射组合物的评估
评估抗反射组合物的与光刻用途相关的以下特性：1)涂膜层的厚度，2)首先可能发生组合物膜层硬化的起始温度，3)组合物膜层覆盖，4)光学参数，5)组合物的膜层的接触角，和6)组合物膜层的升华测试。使用下表1中列出的方案来评估这些特性：
表1：
Figure GDA0003435279300000201
结果
第1部分：光学和功能测试性能.
将实例5、6、7和8中的每一个的抗反射组合物的膜层旋涂到硅晶片上，并如上表1中所述评估伴随193nm辐射的光学参数、接触角和相对升华度。结果列于下表2中。
表2：193nm下的n/k值、接触角和升华度结果
Figure GDA0003435279300000211
第2部分：起始温度和膜覆盖结果.
将实例5、6、7和8中的每一个的抗反射组合物的膜层旋涂到硅晶片上，并如上表1中所述评估起始温度和膜覆盖。结果列于下表3中。如表3中所论述，实例5、6和7的抗反射组合物表现出较低的起始温度(90℃→60℃)。实例5、6和7的抗反射组合物还提供了与实例8(对比)相比，大大改善的膜覆盖特性。
表3：利用起始温度的膜覆盖结果。
Figure GDA0003435279300000212

Claims (9)

1.一种形成光致抗蚀剂浮雕图像的方法，所述方法包含：
a)在衬底上涂覆一层涂料组合物，所述涂料组合物包含：1)树脂；和2)包含式(I)结构的热酸产生剂：
Figure FDA0003435279290000011
其中Y具有式(II)结构：
Figure FDA0003435279290000012
每个R1独立地为CN、NO2、F、Cl、Br、I或CF3；n是1到5的整数；并且X是阴离子组分；和
b)在所述涂料组合物层上涂覆一层光致抗蚀剂组合物，
所述树脂选自包含异氰尿酸酯单元的聚酯树脂或含有异氰尿酸酯取代的聚酯树脂。
2.根据权利要求1所述的方法，其中至少一个R1是F和/或至少一个R1是CF3和/或X是甲苯磺酸酯。
3.根据权利要求1所述的方法，其中所述热酸产生剂化合物具有下式(A)、(B)或(C)结构：
Figure FDA0003435279290000013
Figure FDA0003435279290000021
4.根据权利要求1所述的方法，其中式(I)的YH是以下结构中的一个：
Figure FDA0003435279290000022
5.一种形成光致抗蚀剂浮雕图像的方法，所述方法包含：
a)在衬底上涂覆一层涂料组合物，所述涂料组合物包含：1)树脂；和2)包含式(I)结构的热酸产生剂：
Figure FDA0003435279290000023
其中Y具有式(II)结构：
Figure FDA0003435279290000024
每个R1独立地为卤素、C1-C6卤烷基、-CN、-NO2、-COR2、-COOR2、-CONR2或-SO2R2；
R2独立地为氢、C1-C6烷基、C3-C6环烷基或苯基，其能够任选地被取代；
n是1到5的整数；并且
X是阴离子组分；和
b)在所述涂料组合物层上涂覆一层光致抗蚀剂组合物，
所述树脂选自包含异氰尿酸酯单元的聚酯树脂或含有异氰尿酸酯取代的聚酯树脂。
6.一种经涂布衬底，其包含：
衬底，所述衬底包含
a)涂料组合物，所述涂料组合物包含：1)树脂；和2)包含式(I)结构的热酸产生剂：
Figure FDA0003435279290000031
其中Y具有式(II)结构：
Figure FDA0003435279290000032
每个R1独立地为卤素、C1-C6卤烷基、-CN、-NO2、-COR2、-COOR2、-CONR2或-SO2R2；
R2独立地为氢、C1-C6烷基、C3-C6环烷基或苯基，其能够任选地被取代；
n是1到5的整数；并且
X是阴离子组分；和
b)所述涂料组合物层上的一层光致抗蚀剂组合物，
所述树脂选自包含异氰尿酸酯单元的聚酯树脂或含有异氰尿酸酯取代的聚酯树脂。
7.根据权利要求6所述的衬底，其中式(I)的YH是以下结构中的一个：
Figure FDA0003435279290000033
Figure FDA0003435279290000041
8.一种与外涂光致抗蚀剂组合物一起使用的抗反射组合物，所述抗反射组合物包含：
1)树脂；和
2)包含式(IA)结构的热酸产生剂：
Figure FDA0003435279290000042
其中Y具有式(IIA)结构：
Figure FDA0003435279290000043
每个R1独立地为C1-C6卤烷基、-CN、-NO2、-COR2、-COOR2、-CONR2或-SO2R2；
R2独立地为氢、任选经取代的C1-C6烷基、任选经取代的C3-C6环烷基或任选经取代的苯基；n是1到5的整数；并且X是阴离子组分，
所述树脂选自包含异氰尿酸酯单元的聚酯树脂或含有异氰尿酸酯取代的聚酯树脂。
9.根据权利要求8所述的抗反射组合物，其中式(IA)的YH为以下结构中的一个：
Figure FDA0003435279290000044
Figure FDA0003435279290000051
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