CN116157447A - 包含乙内酰脲化合物的反应产物的抗蚀剂下层膜形成用组合物 - Google Patents
包含乙内酰脲化合物的反应产物的抗蚀剂下层膜形成用组合物 Download PDFInfo
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- CN116157447A CN116157447A CN202180060511.0A CN202180060511A CN116157447A CN 116157447 A CN116157447 A CN 116157447A CN 202180060511 A CN202180060511 A CN 202180060511A CN 116157447 A CN116157447 A CN 116157447A
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- Materials For Photolithography (AREA)
Abstract
本发明提供能够形成所期望的抗蚀剂图案的抗蚀剂下层膜形成用组合物、以及使用了该抗蚀剂下层膜形成用组合物的抗蚀剂图案制造方法、半导体装置的制造方法。该抗蚀剂下层膜形成用组合物包含反应产物、及有机溶剂,所述反应产物是(A)具有2个环氧基的含乙内酰脲的化合物和(B)与(A)不同的含乙内酰脲的化合物的反应产物。优选上述反应产物是(B)含乙内酰脲的化合物所具有的仲氨基与(A)含乙内酰脲的化合物所具有的环氧基的反应产物。
Description
技术领域
本发明涉及用于半导体制造中的光刻工艺中,特别是最先进(ArF、EUV、EB等)的光刻工艺中的组合物。另外,还涉及带有应用了上述抗蚀剂下层膜的抗蚀剂图案的基板的制造方法、及半导体装置的制造方法。
背景技术
一直以来,在半导体装置的制造中,通过使用了抗蚀剂组合物的光刻进行微细加工。上述微细加工是在硅晶片等半导体基板上形成光致抗蚀剂组合物的薄膜,在其上隔着描绘有器件图案的掩模图案照射紫外线等活性光线,进行显影,将得到的光致抗蚀剂图案作为保护膜对基板进行蚀刻处理,从而在基板表面上形成与上述图案对应的微细凹凸的加工方法。近年来,半导体器件趋向高集成度化,所使用的活性光线除了以往使用的i射线(波长365nm)、KrF准分子激光(波长248nm)、ArF准分子激光(波长193nm)以外,也在最先进的微细加工中正在研究EUV光(极紫外线,波长13.5nm)或EB(电子束)的实用化。与此相伴,半导体基板对抗蚀剂的影响已成为大的问题。
因此,为了解决该问题,广泛研究了抗蚀剂与半导体基板之间设置抗蚀剂下层膜的方法。
专利文献1中公开了包含具有乙内酰脲环的化合物的抗蚀剂下层膜形成用组合物。专利文献2中公开了一种EUV光刻用抗蚀剂下层膜形成用组合物,其包含使含异氰脲酸的化合物与巴比妥缩合而成的聚合物。专利文献3中公开了一种光刻用抗蚀剂下层膜形成用组合物,其在聚合物链末端具有包含磺酰基的结构。
现有技术文献
专利文献
专利文献1:国际公开2018/012253号公报
专利文献2:国际公开2013/018802号公报
专利文献3:国际公开2015/163195号公报
发明内容
发明所要解决的问题
作为抗蚀剂下层膜所要求的特性,可以列举例如,不发生与形成于上层的抗蚀剂膜的混合(不溶于抗蚀剂溶剂)、与抗蚀剂膜相比干蚀刻速度快。
在伴随EUV曝光的光刻的情况下,所形成的抗蚀剂图案的线宽达到32nm以下,EUV曝光用的抗蚀剂下层膜与以往相比使用时形成更薄的膜厚。在形成这样的薄膜时,由于基板表面、所使用的聚合物等的影响,容易产生针孔、凝聚等,难以形成没有缺陷的均匀膜。
另一方面,在抗蚀剂图案形成时,有时采用在显影工序中,使用可溶解抗蚀剂膜的溶剂,通常为有机溶剂将前述抗蚀剂膜的未曝光部分除去,将该抗蚀剂膜的曝光部分作为抗蚀剂图案残留的方法。在这样的负型显影工艺中,抗蚀剂图案的密合性改善成为大的问题。
另外,需要抑制抗蚀剂图案形成时的LWR(Line Width Roughness,线宽粗糙度,线宽的波动(粗糙度))的恶化,形成具有良好的矩形形状的抗蚀剂图案,以及抗蚀剂灵敏度的提高。
本发明的目的在于提供解决了上述问题的、可以形成所期望的抗蚀剂图案的抗蚀剂下层膜形成用组合物、以及使用该抗蚀剂下层膜形成用组合物的抗蚀剂图案形成方法。
解决问题的手段
本发明包含以下内容。
[1]一种抗蚀剂下层膜形成用组合物,其包含反应产物、及有机溶剂,所述反应产物是(A)具有2个环氧基的含乙内酰脲的化合物和(B)与(A)不同的含乙内酰脲的化合物的反应产物。
[2]根据[1]所述的抗蚀剂下层膜形成用组合物,所述反应产物是(B)含乙内酰脲的化合物所具有的仲氨基与(A)含乙内酰脲的化合物所具有的环氧基的反应产物。
[3]根据[1]所述的抗蚀剂下层膜形成用组合物,其中所述(A)化合物由式(A-1)表示,所述(B)化合物由式(B-1)表示:
式(A-1)及式(B-1)中,T1、T2、T3和T4各自独立地表示氢原子、可以被氧原子或硫原子中断且可以被羟基取代的碳原子数为1~10的烷基、可以被羟基取代的碳原子数为6~40的芳基或碳原子数为3~6的烯基。
[4]根据[1]~[3]中任一项所述的抗蚀剂下层膜形成用组合物,所述反应产物的末端被具有官能团的化合物封端。
[5]根据[4]所述的抗蚀剂下层膜形成用组合物,所述官能团选自羧基、羟基、氨基、亚氨基及硫醇基。
[6]根据[4]所述的抗蚀剂下层膜形成用组合物,所述具有官能团的化合物包含碳-碳键可以被杂原子中断且可以被取代基取代的脂肪族环。
[7]根据[4]或[5]所述的抗蚀剂下层膜形成用组合物,所述被具有官能团的化合物封端的结构由下述式(1)和式(2)表示:
式(1)和式(2)中,R1表示可以具有取代基的碳原子数为1~6的烷基、苯基、吡啶基、卤素基或羟基,R2表示氢原子、碳原子数为1~6的烷基、羟基、卤素基或-C(=O)O-X表示的酯基,X表示可以具有取代基的碳原子数为1~6的烷基,R3表示氢原子、碳原子数为1~6的烷基、羟基或卤素基,R4表示直接键合、或碳原子数为1~8的二价有机基团,R5表示碳原子数为1~8的二价有机基团,A表示芳香族环或芳香族杂环,t表示0或1,u表示1或2。
[8]根据[1]~[7]中任一项所述的抗蚀剂下层膜形成用组合物,其中还包含产酸剂。
[9]根据[1]~[8]中任一项所述的抗蚀剂下层膜形成用组合物,其中还包含交联剂。
[10]根据[1]~[9]中任一项所述的下层膜形成用组合物,是电子束或EUV抗蚀剂下层膜形成用组合物。
[11]一种抗蚀剂下层膜,其特征在于,是由[1]~[10]中任一项所述的抗蚀剂下层膜形成用组合物形成的涂布膜的烧成物。
[12]一种图案化基板的制造方法,其包含在半导体基板上涂布[1]~[10]中任一项所述的抗蚀剂下层膜形成用组合物并进行烘烤而形成抗蚀剂下层膜的工序、在所述抗蚀剂下层膜上涂布抗蚀剂并进行烘烤而形成抗蚀剂膜的工序、对被上述抗蚀剂下层膜和上述抗蚀剂被覆的半导体基板进行曝光的工序、对曝光后的上述抗蚀剂膜进行显影、图案化的工序。
[13]一种半导体装置的制造方法,其特征在于,包含:
在半导体基板上形成由[1]~[10]中任一项所述的抗蚀剂下层膜形成用组合物形成的抗蚀剂下层膜的工序、
在上述抗蚀剂下层膜上形成抗蚀剂膜的工序、
通过对抗蚀剂膜进行光或电子束的照射和之后的显影而形成抗蚀剂图案的工序、
隔着形成的上述抗蚀剂图案对上述抗蚀剂下层膜进行蚀刻,从而形成图案化的抗蚀剂下层膜的工序、和
利用图案化的上述抗蚀剂下层膜对半导体基板进行加工的工序。
发明效果
在使用包含上述的(A)具有2个环氧基的含乙内酰脲的化合物和(B)与(A)不同的含乙内酰脲的化合物的反应产物的抗蚀剂下层膜形成用组合物形成抗蚀剂图案的情况下,极限分辨率尺寸与以往的抗蚀剂下层膜相比变得更小,所述极限分辨率尺寸是观察不到显影后的抗蚀剂图案倒塌的分辨率尺寸,可以形成更微细的抗蚀剂图案。另外,还可起到如下效果,即显示良好图案的抗蚀图案尺寸的范围与现有技术相比增大。
具体实施方式
本申请的抗蚀剂下层膜形成用组合物包含反应产物、及有机溶剂,所述反应产物是(A)具有2个环氧基的含乙内酰脲化合物和(B)与(A)不同的含乙内酰脲的化合物的反应产物。所述反应产物优选为(B)含乙内酰脲的化合物所具有的仲氨基与(A)含乙内酰脲的化合物所具有的环氧基的反应产物。该反应可以通过公知的方法进行。
上述(A)化合物由式(A-1)表示,上述(B)化合物由式(B-1)表示:
式(A-1)及式(B-1)中,T1、T2、T3和T4各自独立地表示氢原子、可以被氧原子或硫原子中断且可以被羟基取代的碳原子数为1~10的烷基、可以被羟基取代的碳原子数为6~40的芳基或碳原子数为3~6的烯基。T1、T2、T3和T4可以全部相同,也可以全部不同,还可以一部分相同。
其中,T1、T2、T3和T4优选为碳原子数为1~10的烷基或碳原子数为6~40的芳基。
作为上述碳原子数为1~10的烷基,可以列举甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、1-甲基环丙基、2-甲基环丙基、正戊基、1-甲基正丁基、2-甲基正丁基、3-甲基正丁基、1,1-二甲基正丙基、1,2-二甲基正丙基、2,2-二甲基正丙基、1-乙基正丙基、环戊基、1-甲基环丁基,2-甲基环丁基、3-甲基环丁基,1,2-二甲基环丙基、2,3-二甲基环丙基、1-乙基环丙基、2-乙基环丙基、正己基、1-甲基正戊基、2-甲基正戊基、3-甲基正戊基、4-甲基正戊基、1,1-二甲基正丁基、1,2-二甲基正丁基、1,3-二甲基正丁基、2,2-二甲基正丁基、2,3-二甲基正丁基、3,3-二甲基正丁基、1-乙基正丁基、2-乙基正丁基、1,1,2-三甲基正丙基、1,2,2-三甲基正丙基、1-乙基-1-甲基正丙基、1-乙基-2-甲基正丙基、环己基、1-甲基环戊基、2-甲基环戊基、3-甲基环戊基、1-乙基环丁基、2-乙基环丁基、3-乙基环丁基、1,2-二甲基环丁基、1,3-二甲基环丁基、2,2-二甲基环丁基、2,3-二甲基环丁基、2,4-二甲基环丁基、3,3-二甲基环丁基、1-正丙基环丙基、2-正丙基环丙基、1-异丙基环丙基、2-异丙基环丙基、1,2,2-三甲基环丙基、1,2,3-三甲基环丙基、2,2,3-三甲基环丙基、1-乙基-2-甲基环丙基、2-乙基-1-甲基环丙基、2-乙基-2-甲基环丙基、2-乙基-3-甲基环丙基、癸基。
作为上述碳原子数为6~40的芳基,可以列举苯基、邻甲基苯基、间甲基苯基、对甲基苯基、邻氯苯基、间氯苯基、对氯苯基、邻氟苯基、对氟苯基、邻甲氧基苯基、对甲氧基苯基、对硝基苯基、对氰基苯基、α-萘基、β-萘基、邻联苯基、间联苯基、对联苯基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基和9-菲基。
作为上述碳原子数为3~6的烯基,可以列举1-丙烯基、2-丙烯基、1-甲基-1-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-正丙基乙烯基、1-甲基-1-丁烯基、1-甲基-2-丁烯基、1-甲基-3-丁烯基、2-乙基-2-丙烯基、2-甲基-1-丁烯基、2-甲基-2-丁烯基、2-甲基-3-丁烯基、3-甲基-1-丁烯基、3-甲基-2-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1-异丙基乙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-环戊烯基、2-环戊烯基、3-环戊烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、1-甲基-2-戊烯基、1-甲基-3-戊烯基、1-甲基-4-戊烯基、1-正丁基乙烯基、2-甲基-1-戊烯基、2-甲基-2-戊烯基、2-甲基-3-戊烯基、2-甲基-4-戊烯基、2-正丙基-2-丙烯基、3-甲基-1-戊烯基、3-甲基-2-戊烯基、3-甲基-3-戊烯基、3-甲基-4-戊烯基、3-乙基-3-丁烯基、4-甲基-1-戊烯基、4-甲基-2-戊烯基、4-甲基-3-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1-甲基-2-乙基-2-丙烯基、1-仲丁基乙烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、1-异丁基乙烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、2-异丙基-2-丙烯基、3,3-二甲基-1-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、1-正丙基-1-丙烯基、1-正丙基-2-丙烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-叔丁基乙烯基、1-甲基-1-乙基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基、1-异丙基-1-丙烯基、1-异丙基-2-丙烯基、1-甲基-2-环戊烯基、1-甲基-3-环戊烯基、2-甲基-1-环戊烯基、2-甲基-2-环戊烯基、2-甲基-3-环戊烯基、2-甲基-4-环戊烯基、2-甲基-5-环戊烯基、2-亚甲基环戊基、3-甲基-1-环戊烯基、3-甲基-2-环戊烯基、3-甲基-3-环戊烯基、3-甲基-4-环戊烯基、3-甲基-5-环戊烯基、3-亚甲基环戊基、1-环己烯基、2-环己烯基及3-环己烯基等。
作为上述(A)化合物的优选具体例子,可以列举以下的化合物。
作为上述(B)化合物的优选具体例子,可以列举以下的化合物。
作为本发明的抗蚀剂下层膜形成用组合物中包含的有机溶剂,可以列举例如,乙二醇单甲醚、乙二醇单乙醚、甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯、二甘醇单甲醚、二甘醇单乙醚、丙二醇、丙二醇单甲基醚、丙二醇单乙醚、丙二醇单甲醚乙酸酯、丙二醇丙醚乙酸酯、甲苯、二甲苯、甲乙酮、甲基异丁基酮、环戊酮、环己酮、环庚酮、4-甲基-2-戊醇、2-羟基异丁酸甲酯、2-羟基异丁酸乙酯、乙氧基乙酸乙酯、乙酸2-羟基乙酯、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、丙酮酸乙酯、乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯、2-庚酮、甲氧基环戊烷、苯甲醚、γ-丁内酯、N-甲基吡咯烷酮、N,N-二甲基甲酰胺及N,N-二甲基乙酰胺。这些溶剂可以单独使用或组合使用2种以上。
在这些溶剂中,优选丙二醇单甲基醚、丙二醇单甲基醚乙酸酯、乳酸乙酯、乳酸丁酯及环己酮等。特别优选丙二醇单甲基醚、丙二醇单甲基醚乙酸酯。
上述反应产物的重均分子量优选为500~50,000,更优选为1000~30,000。上述重均分子量例如可以通过实施例中记载的凝胶渗透色谱法来测定。
上述反应产物的末端优选被具有官能团的化合物封端。
优选上述官能团选自羧基、羟基、氨基、亚氨基和硫醇基。
上述具有官能团的化合物优选包含碳-碳键可以被杂原子中断且可以被取代基取代的脂肪族环。
上述脂肪族环优选为碳原子数为3~10的单环式或多环式脂肪族环。
上述多环式脂肪族环优选为双环或三环。
上述脂肪族环优选具有至少1个不饱和键。
上述包含碳-碳键可以被杂原子中断且可以被取代基取代的脂肪族环的含羧基化合物的说明依据PCT/JP2020/018436中记载的内容。
上述(A)化合物和(B)化合物的反应产物的末端被碳-碳键可以被杂原子中断且可以被取代基取代的脂肪族环封端的结构,可以通过上述(A)化合物和(B)化合物的反应产物与下述记载的含有碳-碳键可以被杂原子中断且可以被取代基取代的脂肪族环的含羧基化合物的反应来制造。
作为包含碳-碳键可以被杂原子中断且可以被取代基取代的脂肪族环的含羧基化合物的具体例子,可以列举以下记载的化合物。下述具体例子的羧基被羟基、氨基及硫醇基取代的化合物也可以作为具体例子进行列举。
用上述具有官能团的化合物封端的结构优选由下述式(1)或式(2)表示:
式(1)和式(2)中,R1表示可具有取代基的碳原子数为1~6的烷基、苯基、吡啶基、卤素基或羟基,R2表示氢原子、碳原子数为1~6的烷基、羟基、卤素基或-C(=O)O-X表示的酯基,X表示可具有取代基的碳原子数为1~6的烷基,R3表示氢原子、碳原子数为1~6的烷基、羟基或卤素基,R4表示直接键合、或碳原子数为1~8的二价有机基团,R5表示碳原子数为1~8的二价有机基团,A表示芳香族环或芳香族杂环,t表示0或1,u表示1或2。
关于上述式(1)及式(2)中记载的用语的说明,依照WO2015/163195中记载的内容。
由上述式(1)和式(2)表示的、上述(A)化合物和(B)化合物的反应产物的末端结构,可以通过上述(A)化合物和(B)化合物的反应产物与下述式(1a)表示的化合物和/或下述式(2a)表示的化合物的反应来制造。
上述式(1a)和式(2a)的符号的含义如上述式(1)和式(2)中说明的那样。
作为上述式(1a)表示的化合物,可以列举例如下述式表示的化合物。下述具体例子的羧基或羟基被氨基或硫醇基取代的化合物也可以作为具体例子进行列举。
作为上述式(2a)表示的化合物,可以列举例如下述式表示的化合物。下述具体例子的羧基被羟基、氨基或硫醇基取代的化合物也可以作为具体例子进行列举。
另外,作为上述含有亚氨基的化合物,可以列举出下述的化合物。
<产酸剂>
作为本发明的抗蚀剂下层膜形成用组合物中作为任选成分而包含的产酸剂,可以使用热产酸剂、光产酸剂均可,优选使用热产酸剂。作为热产酸剂,可以列举例如,对甲苯磺酸、三氟甲磺酸、吡啶鎓对甲苯磺酸盐(吡啶鎓-对甲苯磺酸)、吡啶鎓-对羟基苯磺酸(对苯酚磺酸吡啶鎓盐)、吡啶鎓-三氟甲磺酸、水杨酸、樟脑磺酸、5-磺基水杨酸、4-氯苯磺酸、4-羟基苯磺酸、苯二磺酸、1-萘磺酸、柠檬酸、苯甲酸、羟基苯甲酸等磺酸化合物和羧酸化合物。
作为上述光产酸剂,可以列举鎓盐化合物、磺酰亚胺化合物、及二磺酰基重氮甲烷化合物等。
作为鎓盐化合物,可以列举二苯基碘鎓六氟磷酸盐、二苯基碘鎓三氟甲磺酸盐、二苯基碘鎓九氟正丁烷磺酸盐、二苯基碘鎓全氟正辛烷磺酸盐、二苯基碘鎓樟脑磺酸盐、双(4-叔丁基苯基)碘鎓樟脑磺酸盐及双(4-叔丁基苯基)碘鎓三氟甲磺酸盐等碘鎓盐化合物、及三苯基锍六氟锑酸盐、三苯基锍九氟正丁烷磺酸盐、三苯基锍樟脑磺酸盐及三苯基锍三氟甲磺酸盐等锍盐化合物等。
作为磺酰亚胺化合物,可以列举例如,N-(三氟甲磺酰氧基)琥珀酰亚胺、N-(九氟正丁磺酰氧基)琥珀酰亚胺、N-(樟脑磺酰氧基)琥珀酰亚胺和N-(三氟甲磺酰氧基)萘二甲酰亚胺等。
作为二磺酰基重氮甲烷化合物,可以列举例如,双(三氟甲基磺酰基)重氮甲烷、双(环己基磺酰基)重氮甲烷、双(苯基磺酰基)重氮甲烷、双(对甲苯磺酰基)重氮甲烷、双(2,4-二甲基苯磺酰基)重氮甲烷、及甲基磺酰基-对甲苯磺酰基重氮甲烷等。
上述产酸剂可以仅使用一种,或者可以组合使用两种以上。
在使用上述产酸剂的情况下,该产酸剂的含有比例相对于下述交联剂例如为0.1质量%~50质量%,优选为1质量%~30质量%。
<交联剂>
作为本发明的抗蚀剂下层膜形成用组合物中作为任选成分包含的交联剂,可以列举例如,六甲氧基甲基三聚氰胺、四甲氧基甲基苯并胍胺、1,3,4,6-四(甲氧基甲基)甘脲(四甲氧基甲基甘脲)(POWDERLINK(注册商标)1174)、1,3,4,6-四(丁氧基甲基)甘脲、1,3,4,6-四(羟基甲基)甘脲、1,3-双(羟基甲基)脲、1,1,3,3-四(丁氧基甲基)脲、1,1,3,3-四(甲氧基甲基)脲及2,4,6-三[双(甲氧基甲基)氨基]-1,3,5-三嗪((商品名)Cymel(注册商标)-303,Nicalack(注册商标)MW-390)。
另外,本申请的交联剂也可以是WO2017/187969号公报中记载的、每分子中具有2~6个与氮原子键合的下述式(1X)表示的取代基的含氮化合物。
式(1X)中,R1表示甲基或乙基。
每分子中具有2~6个上述式(1X)表示的取代基的含氮化合物可以是下述式(1A)表示的甘脲衍生物。
式(1A)中,4个R1各自独立地表示甲基或乙基,R2和R3各自独立地表示氢原子、碳原子数为1~4的烷基、或苯基。
作为上述式(1A)表示的甘脲衍生物,可以列举例如下式(1A-1)至(1A-6)表示的化合物。
上述式(1A)表示的化合物可通过使每分子中具有2~6个与氮原子键合的下述式(2X)表示的取代基的含氮化合物与下述式(3)表示的至少1种化合物进行反应,制造每分子中具有2~6个上述式(1X)表示的取代基的含氮化合物而得到。
式(2X)和式(3)中,R1表示甲基或乙基,R4表示碳原子数为1~4的烷基。
上述式(1A)表示的甘脲衍生物可通过使下述式(2A)表示的甘脲衍生物与上述式(3)表示的至少1种化合物进行反应而得到。
每分子中具有2~6个上述式(2X)表示的取代基的含氮化合物例如为下述式(2A)表示的甘脲衍生物。
式(2A)中,R2和R3各自独立地表示氢原子、碳原子数为1~4的烷基、或苯基,R4各自独立地表示碳原子数为1~4的烷基。
作为式(2A)表示的甘脲衍生物,可以列举例如下式(2A-1)至(2A-4)表示的化合物。进而,作为上述式(3)表示的化合物,可以列举例如下述式(3-1)和式(3-2)表示的化合物。
关于上述每分子中具有2~6个与氮原子键合的下述式(1X)表示的取代基的含氮化合物的内容,依据WO2017/187969号公报中记载的内容。
在使用上述交联剂的情况下,该交联剂的含有比例相对于上述反应产物例如为1质量%~50质量%,优选为5质量%~30质量%。
<其他成分>
在本发明的抗蚀剂下层膜形成用组合物中,为了不产生针孔、条纹等,进一步提高对于表面不均的涂布性,可以进一步添加表面活性剂。作为表面活性剂,可以列举例如,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、聚氧乙烯油基醚等聚氧乙烯烷基醚类、聚氧乙烯辛基苯酚醚、聚氧乙烯壬基酚醚等聚氧乙烯烷基芳基醚类、聚氧乙烯-聚氧丙烯嵌段共聚物类、山梨糖醇酐单月桂酸酯、山梨糖醇酐单棕榈酸酯、山梨糖醇酐单硬脂酸酯、山梨糖醇酐单油酸酯、山梨糖醇酐三油酸酯、山梨糖醇酐三硬脂酸酯等山梨糖醇酐脂肪酸酯类、聚氧乙烯山梨糖醇酐单月桂酸酯、聚氧乙烯山梨糖醇酐单棕榈酸酯、聚氧乙烯山梨糖醇酐单硬脂酸酯、聚氧乙烯山梨糖醇酐三油酸酯、聚氧乙烯山梨糖醇酐三硬脂酸酯等聚氧乙烯山梨糖醇酐脂肪酸酯类等非离子类表面活性剂、エフトップEF301、EF303、EF352((株)トーケムプロダクツ制,商品名)、メガファックF171、F173、R-30(大日本インキ(株)制,商品名)、フロラードFC430、FC431(住友スリーエム(株)制,商品名)、アサヒガードAG710、サーフロンS-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(株)制,商品名)等氟类表面活性剂、有机硅氧烷聚合物KP341(信越化学工业(株)制)等。这些表面活性剂的配合量相对于本发明的抗蚀剂下层膜形成用组合物的全部固形物通常为2.0质量%以下,优选为1.0质量%以下。这些表面活性剂可以单独添加,另外也可以以2种以上的组合添加。
本申请的抗蚀剂下层膜形成用组合物优选为在电子束(EB)描绘工序及EUV曝光工序中使用的电子束抗蚀剂下层膜形成用组合物或EUV抗蚀剂下层膜形成用组合物,优选为EUV抗蚀剂下层膜形成用组合物。
<抗蚀剂下层膜>
本发明涉及的抗蚀剂下层膜可以通过将上述的抗蚀剂下层膜形成用组合物涂布在半导体基板上并进行烧成来制造。
本发明涉及的抗蚀剂下层膜优选为电子束抗蚀剂下层膜或EUV抗蚀剂下层膜。
作为本发明的抗蚀剂下层膜形成用组合物所涂布的半导体基板,可以列举例如,硅晶片、锗晶片、及砷化镓、磷化铟、氮化镓、氮化铟、氮化铝等化合物半导体晶片。
在使用表面形成了无机膜的半导体基板的情况下,该无机膜例如通过ALD(原子层沉积)法、CVD(化学气相沉积)法、反应性溅射法、离子镀法、真空蒸镀法、旋涂法(旋涂玻璃:SOG)形成。作为上述无机膜,可以列举例如,多晶硅膜、氧化硅膜、氮化硅膜、BPSG(Boro-Phospho Silicate Glass)膜、氮化钛膜、氮氧化钛膜、钨膜、氮化镓膜和砷化镓膜。
在这样的半导体基板上,通过旋涂器、涂布机等适当的涂布方法涂布本发明的抗蚀剂下层膜形成用组合物。然后,使用加热板等加热手段进行烘烤,由此形成抗蚀剂下层膜。作为烘烤条件,从烘烤温度100℃~400℃,烘烤时间0.3分钟~60分钟中适当选择。优选为烘烤温度120℃~350℃,烘烤时间0.5分钟~30分钟,更优选为烘烤温度150℃~300℃,烘烤时间0.8分钟~10分钟。烘烤时的温度低于上述范围时,交联变得不充分。另一方面,烘烤时的温度高于上述范围时,抗蚀剂下层膜有时会热分解。
作为形成的抗蚀剂下层膜的膜厚,例如为0.001μm(1nm)~10μm、0.002μm(2nm)~1μm、0.005μm(5nm)~0.5μm(500nm)、0.001μm(1nm)~0.05μm(50nm)、0.002μm(2nm)~0.05μm(50nm)、0.003μm(1nm)~0.05μm(50nm)、0.004μm(4nm)~0.05μm(50nm)、0.005μm(5nm)~0.05μm(50nm)、0.003μm(3nm)~0.03μm(30nm)、0.003μm(3nm)~0.02μm(20nm)、0.005μm(5nm)~0.02μm(20nm)。
<图案化基板的制造方法、半导体装置的制造方法>
图案化基板的制造方法经过以下的工序。通常,可以在抗蚀剂下层膜上形成光致抗蚀剂层而制造。作为在抗蚀剂下层膜上通过本身公知的方法进行涂布、烧成而形成的光致抗蚀剂,只要是对曝光所使用的光感光的光致抗蚀剂就没有特别限制。负型光致抗蚀剂和正型光致抗蚀剂均可以使用。有包含酚醛清漆树脂和1,2-萘醌重氮磺酸酯的正型光致抗蚀剂、包含具有通过酸分解而使碱溶解速度上升的基团的粘合剂和光产酸剂的化学放大型光致抗蚀剂、包含通过酸分解而使光致抗蚀剂的碱溶解速度上升的低分子化合物、碱可溶性粘合剂和光产酸剂的化学放大型光致抗蚀剂、以及包含具有通过酸分解而使碱溶解速度上升的基团的粘合剂、通过酸分解而使光致抗蚀剂的碱溶解速度上升的低分子化合物和光产酸剂的化学放大型光致抗蚀剂、含有金属元素的抗蚀剂等。例如,可以列举JSR(株)制商品名V146G、シプレー社制商品名APEX-E、住友化学工业(株)制商品名PAR710、及信越化学工业(株)制商品名AR2772、SEPR430等。另外,可以列举例如像Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)、Proc.SPIE,Vol.3999,365-374(2000)中记载那样的含氟原子聚合物类光致抗蚀剂。
曝光通过用于形成规定图案的掩模(中间掩模)来进行,使用例如i线、KrF准分子激光、ArF准分子激光、EUV(极紫外线)或EB(电子束),但本申请的抗蚀剂下层膜形成用组合物优选应用于EUV(极紫外线)或EB(电子束)曝光用,特别优选应用于EUV(极紫外线)曝光用。显影中使用碱显影液,从显影温度5℃~50℃,显影时间10秒~300秒中适当选择。作为碱显影液,可以使用例如,氢氧化钠、氢氧化钾、碳酸钠、硅酸钠、偏硅酸钠、氨水等无机碱类、乙胺、正丙胺等伯胺类、二乙胺、二正丁胺等仲胺类、三乙胺、甲基二乙胺等叔胺类、二甲基乙醇胺、三乙醇胺等醇胺类、四甲基氢氧化铵、四乙基氢氧化铵、胆碱等季铵盐、吡咯、哌啶等环状胺类等碱类的水溶液。进而,也可以在上述碱类的水溶液中添加适当量的异丙醇等醇类、非离子类等表面活性剂来使用。其中,优选的显影液为季铵盐,进一步优选为四甲基氢氧化铵和胆碱。进而,也可以在这些显影液中加入表面活性剂等。也可以采用以下方法,即用乙酸丁酯等有机溶剂代替碱显影液进行显影,对光致抗蚀剂的碱溶解速度未提高的部分进行显影。经过上述工序,可以制造上述抗蚀剂被图案化的基板。
接着,将已形成的抗蚀剂图案作为掩模,对上述抗蚀剂下层膜进行干蚀刻。此时,在所使用的半导体基板的表面形成了上述无机膜的情况下,使该无机膜的表面露出,在所使用的半导体基板的表面未形成上述无机膜的情况下,使该半导体基板的表面露出。然后,针对基板通过本身公知的方法(干蚀刻法等)来加工基板,经过该工序可以制造半导体装置。
实施例
以下,列举实施例和比较例,对本发明进行更具体地说明,但本发明并不受下述实施例的限制。
下述合成例所示的聚合物(A)的重均分子量(Mw)是基于凝胶渗透色谱(GelPermeation Chromatography,GPC)法的测定结果。测定中使用東ソー株式会社制GPC装置,测定条件如下所述。
测定装置:HLC-8020GPC(商品名)(東ソー株式会社制)
GPC柱:TSKgel G2000HXL:2根,G3000HXL:1根,G4000HXL:1根(商品名)(全部为東ソー株式会社制)
柱温:40℃
溶剂:四氢呋喃(THF)
流量:1.0ml/分钟
标准试样:聚苯乙烯(東ソー株式会社制)
[合成例1]反应产物1的合成
将N,N-二缩水甘油基-5,5-二甲基乙内酰脲4.91g、5,5-二甲基乙内酰脲2.83g、四丁基溴化鏻0.27g加入到丙二醇单甲醚12.00g中并使其溶解。对反应容器进行氮气置换后,在回流加热下使其反应24小时,得到反应产物1溶液。进行GPC分析,结果所得到的溶液中的反应产物1以标准聚苯乙烯换算为重均分子量1400。
反应产物1包含下述结构作为重复单元结构。
[合成例2]反应产物2的合成
将N,N-二缩水甘油基-5,5-二甲基乙内酰脲4.00g、5-苯基乙内酰脲3.71g、四丁基溴化鏻0.30g加入到丙二醇单甲醚12.00g中并使其溶解。对反应容器进行氮气置换后,在回流加热下使其反应24小时,得到反应产物2溶液。进行GPC分析,结果所得到的溶液中的反应产物2以标准聚苯乙烯换算为重均分子量3500。
反应产物2包含下述结构作为重复单元结构。
[合成例3]反应产物3的合成
将N,N-二缩水甘油基-5,5-二甲基乙内酰脲3.66g、5,5-二苯基乙内酰脲4.15g、四丁基溴化鏻0.20g加入到丙二醇单甲醚12.00g中并使其溶解。对反应容器进行氮气置换后,在回流加热下使其反应24小时,得到反应产物3溶液。进行GPC分析,结果所得到的溶液中的反应产物3以标准聚苯乙烯换算为重均分子量3100。
反应产物3包含下述结构作为重复单元结构。
[合成例4]反应产物4的合成
将N,N-二缩水甘油基-5,5-二甲基乙内酰脲4.52g、5-苯基乙内酰脲2.97g、3-羟基-1-金刚烷羧酸1.17g、四丁基溴化鏻0.34g加入到丙二醇单甲醚11.00g中并使其溶解。对反应容器进行氮气置换后,在回流加热下使其反应24小时,得到反应产物4溶液。进行GPC分析,结果所得到的溶液中的反应产物4以标准聚苯乙烯换算为重均分子量2400。
反应产物4包含下述结构作为重复单元结构。
[合成例5]反应产物5的合成
将N,N-二缩水甘油基-5,5-二甲基乙内酰脲4.01g、5-苯基乙内酰脲2.64g、4-(甲基磺酰基)苯甲酸1.06g、四丁基溴化鏻0.30g加入到丙二醇单甲醚12.00g中并使其溶解。对反应容器进行氮气置换后,在回流加热下使其反应24小时,得到反应产物5溶液。进行GPC分析,结果所得到的溶液中的反应产物5以标准聚苯乙烯换算为重均分子量1900。
反应产物5包含下述结构作为重复单元结构。
[合成例6]反应产物6的合成
将N,N-二缩水甘油基-5,5-二甲基乙内酰脲4.62g、5-苯基乙内酰脲3.04g、5-降冰片烯-2,3-二羧酸酐1.06g、四丁基溴化鏻0.34g加入到丙二醇单甲醚11.00g中并使其溶解。对反应容器进行氮气置换后,在回流加热下使其反应24小时,得到反应产物6溶液。进行GPC分析,结果所得到的溶液中的反应产物6以标准聚苯乙烯换算为重均分子量2100。
反应产物6包含下述结构作为重复单元结构。
<比较合成例1>
将单烯丙基二缩水甘油基异氰脲酸8.00g、巴比妥5.45g、四丁基溴化鏻0.48g加入到丙二醇单甲醚56.00g中并使其溶解。对反应容器进行氮气置换后,在回流加热下使其反应10小时,得到反应产物7溶液。进行GPC分析,结果所得到的溶液中的反应产物7以标准聚苯乙烯换算为重均分子量10000。
反应产物7包含下述结构作为重复单元结构。
<比较合成例2>
将N,N-二缩水甘油基-5,5-二甲基乙内酰脲3.66g、巴比妥5.45g、四丁基溴化鏻0.48g加入到丙二醇单甲醚56.00g中并使其溶解。对反应容器进行氮气置换后,在回流加热下使其反应10小时,得到反应产物8溶液。进行GPC分析,结果所得到的溶液中的反应产物8以标准聚苯乙烯换算为重均分子量4000。
反应产物8包含下述结构作为重复单元结构。
[实施例1]
在上述合成例1中获得的包含0.047g的反应产物1的溶液3.12g中,混合四甲氧基甲基甘脲0.11g和对苯酚磺酸吡啶鎓盐0.012g,加入丙二醇单甲醚263.41g和丙二醇单甲醚乙酸酯29.89g并使其溶解。然后使用孔径0.05μm的聚乙烯制微过滤器进行过滤,制成抗蚀剂下层膜形成用组合物。
[实施例2~6]
使用反应产物2~6代替反应产物1,除此以外,通过与实施例1同样的方法,制成抗蚀剂下层膜形成用组合物。
[比较例1~2]
使用反应产物7~8代替反应产物1,除此以外,通过与实施例1同样的方法,制成抗蚀剂下层膜形成用组合物。
(抗蚀剂图案化评价)
利用电子束描绘装置的抗蚀剂图案形成试验
使用旋涂器将抗蚀剂下层膜形成用组合物分别涂布在硅晶片上。将该硅晶片在电热板上以205℃烘烤60秒,得到膜厚5nm的抗蚀剂下层膜。在该抗蚀剂下层膜上旋涂EUV用负型抗蚀剂溶液(含有甲基丙烯酸类聚合物),在100℃下加热60秒,形成EUV抗蚀剂膜。对于该抗蚀剂膜,使用电子束描绘装置(ELS-G130),在规定的条件下进行曝光。曝光后,在100℃下进行60秒烘烤(PEB),在冷却板上冷却至室温,用乙酸丁酯显影后,形成立柱尺寸为17nm~28nm的抗蚀剂图案。抗蚀剂图案的测量使用扫描型电子显微镜(日立ハイテクノロジーズ制,CG4100)。
对于这样得到的光致抗蚀剂图案,从图案上部进行观察,确认了在抗蚀剂图案的取景内看不到倒塌(塌缩)的最小CD尺寸和看不到与相邻图案连接(桥接)的最大CD尺寸,确认了图案进行良好解像的范围。该范围越大,表示能够形成良好图案的图案范围越宽,实施例1~6的结果显示了与比较例1、2相比能够形成良好图案的尺寸范围更宽。
将上述实施例1~6和比较例1、2中确认的抗蚀剂图案的观察结果示于表1中。
表1
产业上的可利用性
本发明涉及的抗蚀剂下层膜形成用组合物,可以提供用于形成可以形成所期望的抗蚀剂图案的抗蚀剂下层膜的组合物、以及带有使用了该抗蚀剂下层膜形成用组合物形成的抗蚀剂图案的基板的制造方法、半导体装置的制造方法。
Claims (13)
1.一种抗蚀剂下层膜形成用组合物,其包含反应产物、及有机溶剂,所述反应产物是(A)具有2个环氧基的含乙内酰脲的化合物和(B)与(A)不同的含乙内酰脲的化合物的反应产物。
2.根据权利要求1所述的抗蚀剂下层膜形成用组合物,所述反应产物是(B)含乙内酰脲的化合物所具有的仲氨基与(A)含乙内酰脲的化合物所具有的环氧基的反应产物。
4.根据权利要求1~3中任一项所述的抗蚀剂下层膜形成用组合物,所述反应产物的末端被具有官能团的化合物封端。
5.根据权利要求4所述的抗蚀剂下层膜形成用组合物,所述官能团选自羧基、羟基、氨基、亚氨基及硫醇基。
6.根据权利要求4所述的抗蚀剂下层膜形成用组合物,所述具有官能团的化合物包含碳-碳键可以被杂原子中断且可以被取代基取代的脂肪族环。
8.根据权利要求1~7中任一项所述的抗蚀剂下层膜形成用组合物,其中还包含产酸剂。
9.根据权利要求1~8中任一项所述的抗蚀剂下层膜形成用组合物,其中还包含交联剂。
10.根据权利要求1~9中任一项所述的抗蚀剂下层膜形成用组合物,是电子束或EUV抗蚀剂下层膜形成用组合物。
11.一种抗蚀剂下层膜,其特征在于,是由权利要求1~10中任一项所述的抗蚀剂下层膜形成用组合物形成的涂布膜的烧成物。
12.一种图案化基板的制造方法,其包含在半导体基板上涂布权利要求1~10中任一项所述的抗蚀剂下层膜形成用组合物并进行烘烤而形成抗蚀剂下层膜的工序、在所述抗蚀剂下层膜上涂布抗蚀剂并进行烘烤而形成抗蚀剂膜的工序、对被所述抗蚀剂下层膜和所述抗蚀剂被覆的半导体基板进行曝光的工序、对曝光后的所述抗蚀剂膜进行显影、图案化的工序。
13.一种半导体装置的制造方法,其特征在于,包含:
在半导体基板上形成由权利要求1~10中任一项所述的抗蚀剂下层膜形成用组合物形成的抗蚀剂下层膜的工序、
在所述抗蚀剂下层膜上形成抗蚀剂膜的工序、
通过对抗蚀剂膜进行光或电子束的照射和之后的显影而形成抗蚀剂图案的工序、
隔着形成的所述抗蚀剂图案对所述抗蚀剂下层膜进行蚀刻,从而形成图案化的抗蚀剂下层膜的工序、和
利用已图案化的上述抗蚀剂下层膜对半导体基板进行加工的工序。
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