CN109725492B - 与光致抗蚀剂一起使用的下层涂料组合物 - Google Patents
与光致抗蚀剂一起使用的下层涂料组合物 Download PDFInfo
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- CN109725492B CN109725492B CN201811178032.5A CN201811178032A CN109725492B CN 109725492 B CN109725492 B CN 109725492B CN 201811178032 A CN201811178032 A CN 201811178032A CN 109725492 B CN109725492 B CN 109725492B
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Abstract
提供了包括能够显示出标准等离子体蚀刻剂增强的蚀刻速率的抗反射组合物的新的组合物和方法。相对于现有组合物,本发明优选的抗反射涂料组合物具有降低的碳含量。
Description
技术领域
本发明涉及包括能够显示出标准等离子体蚀刻剂增强的蚀刻速率的抗反射组合物的新的组合物和方法。相对于现有组合物,本发明优选的抗反射涂料组合物具有降低的碳含量。
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,通过图案化的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,这些区域界定了需要转移到下层衬底的图像。通过使抗蚀剂涂层中的潜像图案显影来提供浮雕图像。
已知的光致抗蚀剂能够提供分辨率和尺寸足够用于许多现有的商业应用的特征。然而,对于许多其它应用来说,需要能够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会对光致抗蚀剂层中图案化的图像的分辨率造成限制。辐射从衬底/光致抗蚀剂界面的反射会使光致抗蚀剂中的辐射强度产生空间变化,导致显影时不均一的光致抗蚀剂线宽。辐射还会从衬底/光致抗蚀剂界面散射到光致抗蚀剂的非预期暴露区中,这又会导致线宽变化。散射和反射的量通常在不同区域之间变化,这导致进一步的线宽不均一性。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入在衬底表面与光致抗蚀剂涂层之间的辐射吸收层。这类层也被称为抗反射层或抗反射组合物。参见US9541834;US20150212414;US6767689B2;US6887648B2;和US8623589。又参见美国专利8501383;8507192;和7183037。
虽然已经发现现有的下层抗反射涂料组合物可能对许多抗反射应用来说是有效的,但那些现有组合物也可能造成一些潜在的性能限制。
具体来说,下层抗反射涂料组合物的蚀刻速率可能是有问题的。在下层抗反射涂料组合物层进行等离子体蚀刻从而裸露衬底(例如微电子晶片)表面期间,等离子体蚀刻也将去除上覆的显影的光致抗蚀剂掩模。在ARC完成后,必须保留抗蚀剂掩模的有效厚度,以在裸露的衬底表面加工期间起作用。然而,随着去除ARC层所需的时间增加,光致抗蚀剂掩模的劣化程度也在增加。这是很不期望发生的。
应尽可能地最小化光致抗蚀剂的劣化,以涂覆薄的光致抗蚀剂层。通常需要较薄的抗蚀剂层以提供图案化图像的最大分辨率。如果在下层抗反射涂料组合物蚀刻期间不希望的膜厚度损失(UFTL)显著,那么必须涂覆较厚的抗蚀剂层,以便在蚀刻过程结束时保留有效厚度的抗蚀剂掩模。
因此将期望具有与外涂的光致抗蚀剂一起使用的新的抗反射涂料组合物。特别期望具有通过更快的蚀刻速率使光致抗蚀剂降解最小化的新的抗反射涂料组合物。
发明内容
我们现在发现了新的方法、涂布的衬底和特别适合用作193nm有机底部抗反射涂料(BARC)的抗反射涂料组合物。将光致抗蚀剂涂覆在本发明抗反射涂料组合物的涂层上。
特别优选的下层涂料组合物能够显示出等离子体蚀刻剂如F2/O2等离子体蚀刻剂增强的蚀刻速率。
在优选的方面,提供了包含树脂的下层涂料组合物,所述树脂包含含有下式(I)的结构的重复单元:
其中R1、R2和R3各自独立地是氢或非氢取代基,其中R1、R2和R3中的至少一个是-(CXY)(C=O)O-R,其中R是键联到另一聚合物单元的键,并且X和Y各自独立地是氢或非氢取代基,例如卤素或任选取代的烷基或任选取代的烷氧基;以及b)在涂料组合物层上涂覆一层光致抗蚀剂组合物。通常优选的是X和Y中的一个或两个是氢,即其中R1、R2和R3中的至少一个是-CH2(C=O)O-R。
在一个优选的方面,在式(I)中,R1、R2和R3中的每一个都不是氢。在一个特别优选的方面,R1、R2和R3中的至少两个是-(CXY)(C=O)O-R,其中R是键联到另一聚合物单元的键,并且X和Y各自独立地是氢或非氢取代基,例如卤素或任选取代的烷基或任选取代的烷氧基。优选地,R1、R2和R3中的至少一个:1)不是-(CXY)(C=O)O-R;并且2)包含一个或多个氧原子。
在优选的方面,优选的树脂可以包含能够由下式(II)的单体的反应得到的聚合基团:
其中在式(II)中,P是氢或非氢取代基并且可以适当地是例如任选取代的烷氧基、任选取代的烷基或任选取代的羧基(例如-(C=O)OH)。
树脂可以进一步包括共价交联剂单元,即例如在涂覆的涂层进行热能加热(例如150℃,60秒)时反应的树脂单元,以形成树脂之间的共价键或以其它方式硬化所涂覆的组合物层。
树脂可以适当地具有7或更大的Ohnishi参数值,例如7.2、7.3、7.4、7.5、7.6、7.7、7.8、7.9、8.0或8.45或更大。如本文所提及的,Ohnishi参数值被计算为树脂的原子总数(不包括氢)除以树脂的碳原子总数减去树脂的氧和氮原子总数的值。
在某些方面,下层涂料组合物可以适当地包含不同于树脂的交联剂组分。
优选地,可以用活化辐射使外涂的光致抗蚀剂组合物成像,并且使成像的光致抗蚀剂组合物层显影以提供光致抗蚀剂浮雕图像。如所讨论的,涂料组合物层可以在涂覆光致抗蚀剂组合物层之前适当地进行热处理。
本文进一步提供了一种涂布的衬底,其包含:衬底,上面具有:a)涂料组合物,所述涂料组合物包含:1)包含重复单元的树脂,所述重复单元包含下式(I)的结构:
其中R1、R2和R3各自独立地是氢或非氢取代基,其中R1、R2和R3中的至少一个是-(CXY)(C=O)O-R,其中R是键联到另一聚合物单元的键,并且X和Y各自独立地是氢或非氢取代基,例如卤素或任选取代的烷基或任选取代的烷氧基;和b)涂料组合物层上的光致抗蚀剂组合物层。
本文还提供了用于形成光致抗蚀剂浮雕图像的方法,所述方法包含:a)在例如半导体衬底的衬底上涂覆下层涂料组合物,和b)在上面涂覆光致抗蚀剂组合物层。
本发明的其它方面论述于下文中。
具体实施方式
在优选的方面,本文提供了形成光致抗蚀剂浮雕图像的方法。在一个方面,所述方法可以包括在衬底上涂覆一层涂料组合物,并在涂料组合物层上涂覆一层光致抗蚀剂组合物。在另一个优选的方面,本文提供了涂布的衬底,其包括衬底、涂料组合物和涂料组合物层上的光致抗蚀剂组合物层。在进一步优选的方面,本文提供了抗反射涂料组合物,其包括与外涂光致抗蚀剂组合物一起使用的树脂。
涂料组合物层
在一个优选的方面,涂料组合物或涂料组合物层可以形成193nm有机底部抗反射涂层(BARC),已知其是用于在光刻技术中控制反射率和增强光致抗蚀剂膜与衬底之间的界面粘合的重要底层之一。最近,随着用于微尺度图案化的光致抗蚀剂(PR)的临界尺寸减小,PR厚度减小以改善由较差的PR纵横比所造成的物理图案坍塌,因此,作为硬掩模的有机BARC需要更快的蚀刻速率(E/R)性能以通过减小PR厚度来改善蚀刻选择性,并最小化缓慢E/R所引起的蚀刻偏差。
在一个方面,涂料组合物可以包括包含重复单元的树脂,所述重复单元包含下式(I)的结构:
其中R1、R2和R3各自独立地是氢或非氢取代基,其中R1、R2和R3中的至少一个是-CH2C(=O)O-R,其中R是键联到另一树脂单元的键;以及在涂料组合物层上涂覆一层光致抗蚀剂组合物。
在某些优选的方面,R1、R2和R3中的每一个都不是氢。在一个优选的方面,R1、R2和R3中的至少两个是-CH2C(=O)O-R,其中R是键联到另一聚合物单元的键。在一个优选的方面,R1、R2和R3中的至少一个:1)不是-CH2C(=O)O-R;并且2)包含一个或多个氧原子。
优选地,聚合物可以在193nm浸没式光刻中提供降低的反射率。
如上所述,优选的树脂可以包含能够由下式(II)的单体反应得到的聚合基团:
其中在式(II)中,P是氢或非氢取代基,并且可以适当地是例如任选取代的烷氧基、任选取代的烷基或任选取代的羧基(例如-(C=O)OH)。
在一个示例性实施例中,下层涂料组合物的优选树脂可以包含如下式(III)的括号内所示的结构。
其中式(III)的R4是可以特别在热处理(如150℃,60秒)时交联或形成树脂之间的共价键的基团;并且R5适当地是氢或非氢取代基,例如任选取代的烷基、任选取代的烷氧基或任选取代的碳环烷基,其中一个、两个或三个羟基是这类烷基、烷氧基或碳环芳基的优选取代基。优选的R4基团包括含氮部分,例如甘脲。
在以上式(I)、(II)和(III)中,合适的非氢取代基可以是例如任选取代的C1-20烷基、任选取代的C1-20烷氧基,如任选取代的烷基(例如任选取代的C1-10烷基);任选取代的优选地具有2到约20个碳原子的烯基或炔基,如烯丙基;任选取代的优选地具有1到约20个碳原子的酮;任选取代的优选地具有1到约20个碳原子的烷基硫基;任选取代的优选地具有1到约20个碳原子的烷基亚磺酰基;任选取代的优选地具有1到约20个碳原子的烷基磺酰基;任选取代的优选地具有1到约20个碳原子的羧基(其包括如-COOR′的基团,其中R′是H或C1-8烷基,包括与光酸基本上不反应的酯)等等。
如本文,包括关于上述式(I)、(II)和(III)还讨论的,各种取代基可以适当地被任选取代。“被取代的”取代基可以在一个或多个可供使用的位置、通常1、2或3个位置处被一个或多个合适的基团取代,所述合适的基团如卤素(确切地说F、Cl或Br);氰基;硝基;C1-8烷基;C1-8烷氧基;C1-8烷基硫基;C1-8烷基磺酰基;C2-8烯基;C2-8炔基;羟基;硝基;烷酰基,例如C1-6烷酰基,例如酰基;卤烷基,确切地说C1-8卤烷基,例如CF3;-CONHR、-CONRR’,其中R和R’是任选取代的C1-8烷基;-COOH、COC、>C=O;等等。
在优选的实施例中,本发明的下层涂料组合物的树脂可以包括一个或多个重复单元,所述重复单元包括在下列式(A)至(R)中的任一个的括号内描绘的结构:
其中那些上述结构(A)至(R)中的“X-连接子”表示在热处理过程中(例如170℃,60秒)可以与其它树脂单元反应的部分,如甘脲等。
在特定的实施例中,本发明的下层涂料组合物的树脂可以包括一个或多个重复单元,所述重复单元包括在下列式(PA)至(PR)中的任一个的括号内描绘的结构:
在优选的实施例中,包括如本文所述的重复单元的树脂可以为包含树脂的下层涂料组合物提供增加的蚀刻速率(E/R)。
本发明的下层涂料组合物的尤其优选的树脂可以包含聚酯键。聚酯树脂容易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)化合物进行反应来制备。合适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、环丁二醇、环戊二醇、环己二醇、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。
如所讨论的,本发明的下层涂料组合物的优选树脂可以包含氰尿酸酯(包括异氰尿酸酯)单元。包含聚酯键和氰尿酸酯单元的树脂是特别优选的。
优选地,本发明的下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。
在许多优选实施例中,树脂组分将为下层涂料组合物的主要固体组分。举例来说,一或树脂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。
容易制备用于本发明下层抗反射组合物中的合适和优选的树脂。参见例如以下实例1,其详述了异氰尿酸酯试剂反应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以包含交联剂。举例来说,涂料组合物可以包括基于胺的交联剂,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;和苯并二氨基三嗪(benzoquanamine)和基于脲的物质,其包括树脂,如以名称Cymel 1123和1125购自氰特工业的苯并二氨基三嗪树脂和以名称Powderlink 1174和1196购自氰特工业的脲树脂。除可商购以外,这类基于胺的树脂可以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合适单体共聚来制备。
尤其用于反射控制应用的本发明的涂料组合物还可以含有吸收用于曝光外涂的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流平剂,例如可以凭商品名Silwet 7604购得的流平剂,或购自3M公司的表面活性剂FC 171或FC 431。
本发明的下层涂料组合物还可以含有其它物质,如光酸产生剂,其包括如所论述的与外涂的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。
为了制造液体下层涂料组合物,将涂料组合物的组分溶解于合适溶剂中,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等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。溶剂中的干组分的浓度将取决于若干因素,如涂覆方法。一般来说,下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
与下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,或在光刻加工后可以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能够用碱性水溶液显影的量用于抗蚀剂组合物中。
酸产生剂也适宜与包含含有如包括酚的任选取代的苯基、任选取代的萘基和任选取代的蒽等芳香族基的重复单元的聚合物一起使用。含有任选取代的苯基(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,在含有任选取代的苯基或其它芳香族基的聚合物的情况下,聚合物可以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。这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。
用于形成这类聚合物的优选单体包括:具有下式(IV)的酸不稳定单体、含内酯单体(V)和下式(VI)的极性控制单体,或包含前述单体中的至少一种的组合:
其中每个R1独立地为H、F、-CN、C1-6烷基或C1-6氟烷基。在式(IV)的能够酸脱除保护的单体中,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与相邻的R2键结形成环状结构。在式(V)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(IV)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(IV)单元的合适单体包括例如以下:
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(V)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(V)的单元的合适单体包括例如以下:
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(VI)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(VI)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)。
树脂可以包括一种或多种不同于第一单元的另外的通式(IV)、(V)和/或(VI)的单元。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(IV)单元和/或含内酯的式(V)单元。
除了上述聚合单元之外,树脂还可以包括一种或多种另外的不具有通式(IV)、(V)或(VI)的单元。例如,特别合适的含内酯基的单元具有以下通式(VII):
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另外的通式(VII)的内酯单元:
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化学放大型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以适当地大幅变化。合适的聚合物包括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。
优选的本发明负性组合物包含在暴露于酸后将固化、交联或硬化的物质与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。这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。优选的交联剂包括基于胺的物质,包括三聚氰胺、甘脲、基于苯并胍胺的物质和基于脲的物质。三聚氰胺-甲醛聚合物通常尤其合适。这类交联剂可购得,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以用于浸没式光刻应用中。关于优选的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公司(Rohm and HaasElectronic Materials)的U.S.7968268。
本发明的光致抗蚀剂还可以包含单一酸产生剂或不同酸产生剂的混合物,通常2种或3种不同酸产生剂的混合物,更通常由总共2种不同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,酸产生剂将适宜以按光致抗蚀剂组合物的总固体计,1到20重量%的量存在。
合适的酸产生剂为化学放大型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,酸产生剂可以在曝光于活化辐射,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以称为光酸产生剂化合物。
本发明的光致抗蚀剂还可以含有其它物质。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、增塑剂、速度促进剂和敏化剂。这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,其它添加剂可以包括淬灭剂,其为光无法破坏的碱,如基于氢氧化物、羧酸盐、胺、亚胺和酰胺的那些碱。优选地,这类淬灭剂包括C1-30有机胺、亚胺或酰胺,或可以为强碱(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,如四丁基氢氧化铵(TBAH)或四丁基乳酸铵。
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,如可以从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含氟表面活性剂。
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。
光刻加工
在使用中,本发明的涂料组合物通过如旋涂等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,衬底可以为硅、二氧化硅或铝-氧化铝微电子晶片。也可以采用砷化镓、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、氧化铟锡涂布的衬底等。还可以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下层涂料组合物上之前固化。固化条件将随着下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。
在这类固化之后,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一般,外涂的光致抗蚀剂可以通过任何标准方法,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来干燥以去除溶剂,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的光致抗蚀剂层的互混。
接着抗蚀剂层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的抗蚀剂和抗蚀剂加工。曝光的抗蚀剂层可以在必要时经受曝光后烘烤以在涂层的曝光区与未曝光区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,并且许多化学放大型正性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。
光致抗蚀剂层还可以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被浸没流体,如水或与一种或多种添加剂(如可以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,例如水可以进行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所述曝光是在这类流体层(例如水或具有添加剂的水)插入在曝光工具与涂布的光致抗蚀剂组合物层之间的情况下进行。
接着将曝光的光致抗蚀剂层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合适显影剂处理。在负型显影(NTD)工艺中,光致抗蚀剂层的未曝光区可以通过用合适的非极性溶剂处理而选择性地去除。关于负型显影的合适程序,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以与有机溶剂显影剂形成负像或与如四烷基氢氧化铵溶液等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性(能够脱除保护)基团的聚合物,所述基团在脱除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以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中能够交联,即为负型)的合适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时形成羧酸基的酸敏性(能够脱除保护)基团的聚合物,并且显影剂优选地为不含金属离子的四烷基氢氧化铵溶液,如0.26N四甲基氢氧化铵水溶液。图案通过显影而形成。
接着显影的衬底可以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加工。合适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,可以适当地采用湿法蚀刻工艺。湿法蚀刻可以适当地通过用湿法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。示例性的湿法蚀刻组合物包括氢氧化铵和如过氧化氢等过氧化物的水性混合物,或如硫酸等酸和如过氧化氢等过氧化物的混合物。示例性组合物参见US 2006/0226122。下面的实例还提供了示例性湿法蚀刻工艺条件。如本文所提及,“湿法蚀刻工艺”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,与过氧化物剂组合,但无论如何都与等离子体干法蚀刻不同。
以下非限制性实例是对本发明的说明。
实例1-4:聚合物合成
实例1:聚合物合成
将100ml的3颈圆底烧瓶配备热电偶、迪安-斯塔克装置(Dean-stark)、冷凝器和加热油浴。将三(2-羟乙基)异氰尿酸酯(17.83g,68.2mmol)、2,2',2”-(2,4,6-三氧代基-1,3,5-三嗪烷-1,3,5-三基)三乙酸三叔丁酯(32.17g,68.2mmol)、正丁醇(40.0g,540.0mmol)、对甲苯磺酸(0.39g,2.0mmol)和34g苯甲醚称入烧瓶中。将其加热至设定温度(105℃)并搅拌5小时,将其再加热至设定温度(150℃)并搅拌6.5小时。然后将溶液冷却到室温。将粗反应混合物用THF(70g)稀释以进行分离。用MTBE(700g)沉淀反应混合物,然后过滤并在40℃下真空干燥24小时。将100ml的3颈圆底烧瓶配备热电偶、冷凝器和加热油浴。将预聚物(20g)、对甲苯磺酸(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)称入烧瓶中。将其加热至设定温度(50℃)并搅拌4小时。用三乙胺(TEA)(0.5mL)淬灭溶液。然后将溶液冷却至室温。用异丙醇(IPA)(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:聚合物合成
将100ml的3颈圆底烧瓶配备热电偶、迪安-斯塔克装置、冷凝器和加热油浴。将三(2-羟乙基)异氰尿酸酯(25.91g,99.2mmol)、2,2',2”-(2,4,6-三氧代基-1,3,5-三嗪烷-1,3,5-三基)三乙酸三叔丁酯(24.09g,51.1mmol)、正丁醇(40.0g,540.0mmol)、对甲苯磺酸(0.43g,2.2mmol)和34g苯甲醚称入烧瓶中。将其加热至设定温度(105℃)并搅拌5小时,将其再加热至设定温度(150℃)并搅拌10小时。然后将溶液冷却至室温。将粗物质用THF(70g)稀释以进行分离。用甲基叔丁基酯(MTBE)(700g)沉淀反应混合物,然后过滤并在40℃下真空干燥24小时。将100ml的3颈圆底烧瓶配备热电偶、冷凝器和加热油浴。将预聚物(20g)、对甲苯磺酸(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 HBM称入烧瓶中。将其加热至设定温度(50℃)并搅拌4小时。用TEA(0.5mL)淬灭溶液。然后将溶液冷却至室温。用IPA(1000g)沉淀反应混合物,过滤,然后在40℃下真空干燥24小时。
实例3:聚合物合成
将100ml的3颈圆底烧瓶配备热电偶、迪安-斯塔克装置、冷凝器和加热油浴。将三(2-羟乙基)异氰尿酸酯(14.76g,56.5mmol)、2,2',2”-(2,4,6-三氧代基-1,3,5-三嗪烷-1,3,5-三基)三乙酸三叔丁酯(26.64g,56.5mmol)、1,2-丙二醇(8.60g,113.0mmol)、对甲苯磺酸(0.43g,2.2mmol)和34g苯甲醚称入烧瓶中。将其加热至设定温度(150℃)并搅拌1小时。然后将溶液冷却至室温。将粗物质用THF(80g)稀释以进行分离。用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100ml的3颈圆底烧瓶配备热电偶、冷凝器和加热油浴。将预聚物(20g)、对甲苯磺酸(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 HBM称入烧瓶中。将其加热至设定温度(50℃)并搅拌4小时。用TEA(0.5mL)淬灭溶液。然后将溶液冷却至室温。用IPA(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4:聚合物合成
将100ml的3颈圆底烧瓶配备热电偶、迪安-斯塔克装置、冷凝器和加热油浴。将三(2-羟乙基)异氰尿酸酯(30.43g,116.5mmol)、三(2-羧基乙基)异氰尿酸酯(20.11g,58.2mmol)、正丁醇(20.0g,270.0mmol)、对甲苯磺酸(0.54g,2.8mmol)和34g苯甲醚称入烧瓶中。将其加热至设定温度(150℃)并搅拌3小时。然后将溶液冷却到室温。用HBM(160g)稀释粗物质。将100ml的3颈圆底烧瓶配备热电偶、冷凝器和加热油浴。将预聚物溶液(40g)、对甲苯磺酸(0.08g,0.42mmol)和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(5.0g,10.3mmol)称入烧瓶中。将其加热至设定温度(50℃)并搅拌4小时。用TEA(0.5mL)淬灭溶液。然后将溶液冷却至室温。用IPA(300g)和庚烷(200g)沉淀反应混合物,然后过滤并在40℃下真空干燥24小时。
实例5-8:涂料组合物的配制
实例5
将0.947g上述实例1中制备的聚合物和0.013g对甲苯磺酸2,4,6-三甲基吡啶鎓盐溶于99.0g 2-羟基异丁酸甲酯(HBM)溶剂中,得到涂料组合物。
实例6
将0.947g实例2中制备的聚合物和0.013g对甲苯磺酸2,4,6-三甲基吡啶鎓盐溶于99.0g HBM溶剂中,得到涂料组合物。
实例7
将0.947g实例3中制备的聚合物和0.013g对甲苯磺酸2,4,6-三甲基吡啶鎓盐溶于99.0g HBM溶剂中,得到涂料组合物。
实例8(比较实例)
将0.947g实例4中制备的聚合物和0.013g对甲苯磺酸2,4,6-三甲基吡啶鎓盐溶于99.0g HBM溶剂中,得到组合物。
实例9:抗反射组合物的评估条件
下表1是用于评估本发明抗反射组合物的示例性工艺条件。
表1
实例10-11:光刻工艺和性能评估
实例10:光刻测试条件
下表2列出了光刻评估的示例性工艺和照射条件。
表2
*抗蚀剂是193nm化学放大型正性配制物与甲基丙烯酸酯树脂。
实例11:蚀刻速率和光刻性能
如上所公开,将实例5-8的组合物旋涂到半导体晶片上。
实例5-7的组合物和聚合物显示出更快的E/R性能,与Ohnishi参数值协调,并且特别地,通过n/k与实例8(比较实例)类似,实例7显示出最快的E/R,和相当的EL/图案坍塌宽容度(PCM)和DoF宽容度。下表3显示CF4/Ar气体的蚀刻速率结果,并且表4显示上述实例5-8的组合物的光刻性能总结。
表3
表4
Claims (10)
2.根据权利要求1所述的方法,其中所述树脂还包含交联剂单元。
4.根据权利要求3所述的方法,其中X-连接子是能够交联的部分。
5.根据权利要求1所述的方法,其中所述树脂具有7或更大的Ohnishi参数值。
6.根据权利要求1所述的方法,其中所述涂料组合物还包含不同于所述树脂的交联剂组分。
7.根据权利要求1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。
8.根据权利要求1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进行热处理。
9.一种涂布的衬底,其包含:
衬底,上面具有:
a)包含以下的涂料组合物:
1)包含重复单元的树脂,所述重复单元包含下式(III)的结构:
其中式(III)的R4是可以交联或形成树脂之间的共价键的基团;并且R5是氢、任选取代的C1-20烷基、任选取代的C1-20烷氧基、任选取代的具有2到20个碳原子的烯基或炔基、任选取代的具有1到20个碳原子的酮、任选取代的具有1到约20个碳原子的烷基硫基、任选取代的具有1到20个碳原子的烷基亚磺酰基、任选取代的具有1到20个碳原子的烷基磺酰基;任选取代的具有1到20个碳原子的羧基;和
2)取代的异氰尿酸酯化合物;和
b)所述涂料组合物层上的一层光致抗蚀剂组合物。
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TWI709587B (zh) | 2020-11-11 |
CN109725492A (zh) | 2019-05-07 |
US11500291B2 (en) | 2022-11-15 |
JP6766116B2 (ja) | 2020-10-07 |
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