CN116249729A - 包含已封端的反应产物的抗蚀剂下层膜形成用组合物 - Google Patents
包含已封端的反应产物的抗蚀剂下层膜形成用组合物 Download PDFInfo
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- CN116249729A CN116249729A CN202180067677.5A CN202180067677A CN116249729A CN 116249729 A CN116249729 A CN 116249729A CN 202180067677 A CN202180067677 A CN 202180067677A CN 116249729 A CN116249729 A CN 116249729A
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- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C08G59/14—Polycondensates modified by chemical after-treatment
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1483—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing sulfur
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/32—Polymers modified by chemical after-treatment
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- C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
- C08G65/3346—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur having sulfur bound to carbon and oxygen
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- 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
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- 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
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- G03F7/20—Exposure; Apparatus therefor
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- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
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- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
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- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
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Abstract
本发明提供用于形成能够形成所希望的抗蚀剂图案的抗蚀剂下层膜的组合物、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。本发明为一种抗蚀剂下层膜形成用组合物,其包含末端被化合物(A)封闭的聚合物及有机溶剂,所述聚合物为由下述式(11)(式(11)中,Y1表示单键、氧原子、硫原子、可以被卤素原子或碳原子数6~40的芳基取代的碳原子数1~10的亚烷基或者磺酰基,T1及T2表示碳原子数1~10的烷基,n1及n2各自独立地表示0~4的整数)表示的化合物(B)衍生的聚合物。
Description
技术领域
本发明涉及在半导体制造中的光刻工艺中、尤其是最尖端(ArF、EUV、EB等)的光刻工艺中使用的组合物。另外,涉及采用了上述抗蚀剂下层膜的带有抗蚀剂图案的基板的制造方法、以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,实施了通过使用了抗蚀剂组合物的光刻进行的微细加工。上述微细加工为下述加工法:在硅晶片等半导体基板上形成光致抗蚀剂组合物的薄膜,隔着描绘有器件的图案的掩模图案而向其上照射紫外线等活性光线,进行显影,将所得到的光致抗蚀剂图案作为保护膜而对基板进行蚀刻处理,由此在基板表面形成与上述图案对应的微细凹凸。近年来,半导体器件的高集成度化发展,对于所使用的活性光线也除了以往所用的i射线(波长365nm)、KrF准分子激光(波长248nm)、ArF准分子激光(波长193nm)之外,在最尖端的微细加工中还研究了EUV光(极紫外线,波长13.5nm)或EB(电子射线)的实用化。与之相伴,由半导体基板对抗蚀剂造成的影响成为了大问题。
因此,为了解决该问题,广泛地研究了在抗蚀剂与半导体基板之间设置防反射膜(Bottom Anti-Reflective Coating:BARC)、抗蚀剂下层膜的方法。在专利文献1中,公开了一种在半导体装置制造的光刻工序中使用的抗蚀剂下层膜形成用组合物,其包含在聚合物的主链中含有具有多环式脂肪族环的重复单元结构的该聚合物。在专利文献2中,公开了一种光刻用抗蚀剂下层膜形成用组合物,其包含在末端具有特定结构的聚合物。
现有技术文献
专利文献
专利文献1:日本特开2009-093162号公报
专利文献2:国际公开2013/141015号公报
发明内容
发明所要解决的课题
作为抗蚀剂下层膜所要求的特性,可举出例如,不发生与在其上层形成的抗蚀剂膜的混杂(不溶于抗蚀剂溶剂),干式蚀刻速度比抗蚀剂膜快。
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度成为32nm以下,EUV曝光用的抗蚀剂下层膜以膜厚比以往薄的方式形成并使用。在形成这样的薄膜时,由于基板表面、使用的聚合物等的影响,容易产生针孔、凝集等,难以形成无缺陷的均匀膜。
另一方面,在形成抗蚀剂图案时,在显影工序中,有时采用下述方法:使用能将抗蚀剂膜溶解的溶剂、通常为有机溶剂,将上述抗蚀剂膜的未曝光部除去,使该抗蚀剂膜的曝光部作为抗蚀剂图案而残留。在这样的负性显影工艺中,抗蚀剂图案的密合性的改善成为了重大的课题。
另外,需要抑制形成抗蚀剂图案时的LWR(Line Width Roughness,线宽粗糙度,线宽度的变动(粗糙度))的恶化从而形成具有良好的矩形形状的抗蚀剂图案,以及提高抗蚀剂敏感度。
本发明的目的是提供解决了上述课题的,用于形成能够形成所希望的抗蚀剂图案的抗蚀剂下层膜的组合物、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。
用于解决课题的手段
本发明包括以下内容。
[1]一种抗蚀剂下层膜形成用组合物,其为包含末端被化合物(A)封闭的聚合物及有机溶剂的抗蚀剂下层膜形成用组合物,所述聚合物为由下述式(11)表示的化合物(B)衍生的聚合物。
(式(11)中,
Y1表示单键、氧原子、硫原子、可以被卤素原子或碳原子数6~40的芳基取代的碳原子数1~10的亚烷基或者磺酰基,
T1及T2表示碳原子数1~10的烷基,
n1及n2各自独立地表示0~4的整数)。
优选为下述抗蚀剂下层膜形成用组合物,其为包含末端被化合物(A)封闭的聚合物及有机溶剂的抗蚀剂下层膜形成用组合物,所述聚合物包含来自上述式(11)表示的化合物(B)的重复单元结构。
[2]根据[1]所述的抗蚀剂下层膜形成用组合物,所述化合物(A)包含可以被取代基取代的脂肪族环。
[3]根据[2]所述的抗蚀剂下层膜形成用组合物,所述脂肪族环为碳原子数3~10的单环式或多环式脂肪族环。
[4]根据[2]所述的抗蚀剂下层膜形成用组合物,所述脂肪族环为双环式环或三环式环。
[5]根据[2]~[4]中任一项所述的抗蚀剂下层膜形成用组合物,所述取代基选自羟基、直链状或支链状的碳原子数1~10的烷基、碳原子数1~20的烷氧基、可以被氧原子中断的碳原子数1~10的酰基氧基及羧基。
[6]根据[1]所述的抗蚀剂下层膜形成用组合物,所述化合物(A)由下述式(1)或式(2)表示,
(式(1)及式(2)中,R1表示可具有取代基的碳原子数1~6的烷基、苯基、吡啶基、卤代基或羟基,R2表示氢原子、碳原子数1~6的烷基、羟基、卤代基或-C(=O)O-X所示的酯基,X表示可具有取代基的碳原子数1~6的烷基,R3表示氢原子、碳原子数1~6的烷基、羟基或卤代基,R4表示直接连接键、或碳原子数1~8的二价有机基团,R5表示碳原子数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。)。
[7]根据[1]~[6]中任一项所述的抗蚀剂下层膜形成用组合物,所述聚合物包含由所述化合物(B)、和能与所述化合物(B)反应的化合物(C)衍生的重复单元结构,所述化合物(C)具有杂环结构。
优选为根据[1]~[6]中任一项所述的抗蚀剂下层膜形成用组合物,所述聚合物包含来自所述化合物(B)、和能与所述化合物(B)反应的化合物(C)的重复单元结构,所述化合物(C)具有杂环结构。
[8]根据[1]~[7]中任一项所述的抗蚀剂下层膜形成用组合物,所述Y1为磺酰基。
[9]根据[1]~[8]中任一项所述的抗蚀剂下层膜形成用组合物,其还包含产酸剂。
[10]根据[1]~[9]中任一项所述的抗蚀剂下层膜形成用组合物,其还包含交联剂。
[11]一种抗蚀剂下层膜,其特征在于,其是由[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]一种被图案化了的基板的制造方法,其包括: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从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从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所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从而进行图案化的工序。
[13]一种半导体装置的制造方法,其特征在于,包括:
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的光或电子射线的照射和其后的显影而形成抗蚀剂图案的工序;
通过隔着所形成的所述抗蚀剂图案对所述抗蚀剂下层膜进行蚀刻,从而形成被图案化了的抗蚀剂下层膜的工序;和
利用被图案化了的所述抗蚀剂下层膜对半导体基板进行加工的工序。
发明效果
由上述的包含末端被化合物封闭的聚合物的抗蚀剂下层膜形成用组合物形成的抗蚀剂下层膜,对于在该下层膜的上部形成的光致抗蚀剂中所用的有机溶剂显示出优异的耐性,并且,即使在极薄膜(膜厚为10nm以下)的情况下,也能够形成显示出良好的膜厚均匀性的抗蚀剂下层膜。另外,在使用本发明的抗蚀剂下层膜形成用组合物形成抗蚀剂图案的情况下,观察不到显影后的抗蚀剂图案倒塌的极限析像尺寸与以往的抗蚀剂下层膜相比变得更小,能形成更微细的抗蚀剂图案。另外,还可实现显示出良好图案的抗蚀剂图案尺寸的范围与现有技术相比增大这样的效果。
具体实施方式
<抗蚀剂下层膜形成用组合物>
本发明的抗蚀剂下层膜形成用组合物包含末端被化合物(A)封闭的聚合物及有机溶剂。
<聚合物>
本发明的聚合物为由下述式(11)表示的化合物(B)衍生的聚合物,优选包含上述化合物(B)和能与其反应的化合物(C)的反应产物作为重复单元结构。
(式(11)中,
Y1表示单键、氧原子、硫原子、可以被卤素原子或碳原子数6~40的芳基取代的碳原子数1~10的亚烷基或者磺酰基,
T1及T2表示碳原子数1~10的烷基,
n1及n2各自独立地表示0~4的整数)
上述Y1优选为磺酰基。
作为上述碳原子数6~40的芳基,可举出苯基、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-菲基及9-菲基。
作为上述碳原子数1~10的亚烷基,可举出亚甲基、亚乙基、亚正丙基、亚异丙基、亚环丙基、亚正丁基、亚异丁基、亚仲丁基、亚叔丁基、亚环丁基、1-甲基-亚环丙基、2-甲基-亚环丙基、亚正戊基、1-甲基-亚正丁基、2-甲基-亚正丁基、3-甲基-亚正丁基、1,1-二甲基-亚正丙基、1,2-二甲基-亚正丙基、2,2-二甲基-亚正丙基、1-乙基-亚正丙基、亚环戊基、1-甲基-亚环丁基、2-甲基-亚环丁基、3-甲基-亚环丁基、1,2-二甲基-亚环丙基、2,3-二甲基-亚环丙基、1-乙基-亚环丙基、2-乙基-亚环丙基、亚正己基、1-甲基-亚正戊基、2-甲基-亚正戊基、3-甲基-亚正戊基、4-甲基-亚正戊基、1,1-二甲基-亚正丁基、1,2-二甲基-亚正丁基、1,3-二甲基-亚正丁基、2,2-二甲基-亚正丁基、2,3-二甲基-亚正丁基、3,3-二甲基-亚正丁基、1-乙基-亚正丁基、2-乙基-亚正丁基、1,1,2-三甲基-亚正丙基、1,2,2-三甲基-亚正丙基、1-乙基-1-甲基-亚正丙基、1-乙基-2-甲基-亚正丙基、亚环己基、1-甲基-亚环戊基、2-甲基-亚环戊基、3-甲基-亚环戊基、1-乙基-亚环丁基、2-乙基-亚环丁基、3-乙基-亚环丁基、1,2-二甲基-亚环丁基、1,3-二甲基-亚环丁基、2,2-二甲基-亚环丁基、2,3-二甲基-亚环丁基、2,4-二甲基-亚环丁基、3,3-二甲基-亚环丁基、1-正丙基-亚环丙基、2-正丙基-亚环丙基、1-异丙基-亚环丙基、2-异丙基-亚环丙基、1,2,2-三甲基-亚环丙基、1,2,3-三甲基-亚环丙基、2,2,3-三甲基-亚环丙基、1-乙基-2-甲基-亚环丙基、2-乙基-1-甲基-亚环丙基、2-乙基-2-甲基-亚环丙基、2-乙基-3-甲基-亚环丙基、亚正庚基、亚正辛基、亚正壬基或亚正癸基。
作为上述碳原子数1~10的烷基,可举出甲基、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。它们之中,优选为碳原子数1~4的烷基,优选选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基,优选为甲基或乙基。
上述聚合物优选具有杂环结构。即,优选下文中记载的能进行反应的化合物(C)包含杂环结构。
作为上述杂环结构,可举出呋喃、噻吩、吡咯、咪唑、吡喃、吡啶、嘧啶、吡嗪、吡咯烷、哌啶、哌嗪、吗啉、吲哚、嘌呤、喹啉、异喹啉、奎宁环、色烯、噻蒽、吩噻嗪、吩噁嗪、呫吨、吖啶、吩嗪、咔唑、三嗪酮、三嗪二酮及三嗪三酮、以及作为下述化合物(C)的具体例而列举的(10-h)~(10-k)所示的杂环结构。它们之中,优选为三嗪三酮或下述式(10-k)所记载的杂环结构。
<能与化合物(B)反应的化合物(C)>
作为上述能进行反应的化合物(C),只要是具有能与化合物(B)所具有的羟基反应的取代基的化合物(C),就没有特别限制,但优选为含有2个环氧基的化合物。作为能进行反应的化合物(C)的具体例,可举出下文所记载的化合物。
上述聚合物的重均分子量优选为500~50,000,更优选为1,000~30,000。上述重均分子量可以利用例如实施例中记载的凝胶渗透色谱法来测定。
上述聚合物相对于本发明的抗蚀剂下层膜形成用组合物整体而被包含的比例通常为0.05质量%~3.0质量%,为0.08质量%~2.0质量%,为0.1质量%~1.0质量%。
作为本发明的抗蚀剂下层膜形成用组合物中所含的有机溶剂,可举出例如,乙二醇单甲基醚、乙二醇单乙基醚、甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯、二乙二醇单甲基醚、二乙二醇单乙基醚、丙二醇、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单甲基醚乙酸酯、丙二醇丙基醚乙酸酯、甲苯、二甲苯、甲基乙基酮、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者组合使用2种以上。
这些溶剂之中,优选为丙二醇单甲基醚、丙二醇单甲基醚乙酸酯、乳酸乙酯、乳酸丁酯及环己酮等。特别优选为丙二醇单甲基醚、丙二醇单甲基醚乙酸酯。
<化合物(A)[1]>
上述化合物(A)优选包含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3~10的单环式或多环式脂肪族环。作为上述碳原子数3~10的单环式或多环式脂肪族环,可举出环丙烷、环丁烷、环戊烷、环己烷、环己烯、环庚烷、环辛烷、环壬烷、环癸烷、螺双环戊烷、双环[2.1.0]戊烷、双环[3.2.1]辛烷、三环[3.2.1.02,7]辛烷、螺[3,4]辛烷、降冰片烷、降冰片烯、三环[3.3.1.13,7]癸烷(金刚烷)等。
上述多环式脂肪族环优选为双环式环或三环式环。
作为上述双环式环,可举出降冰片烷、降冰片烯、螺双环戊烷、双环[2.1.0]戊烷、双环[3.2.1]辛烷、螺[3,4]辛烷等。
作为上述三环式环,可举出三环[3.2.1.02,7]辛烷、三环[3.3.1.13,7]癸烷(金刚烷)。
上述可以被取代基取代的脂肪族环是指,该脂肪族环的1个以上的氢原子可以被下文所记载的取代基取代。
优选上述取代基选自羟基、直链状或支链状的碳原子数1~10的烷基、碳原子数1~20的烷氧基、可以被氧原子中断的碳原子数1~10的酰基氧基及羧基。
作为上述碳原子数1~20的烷氧基,可举出甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊基氧基、1-甲基正丁氧基、2-甲基正丁氧基、3-甲基正丁氧基、1,1-二甲基正丙氧基、1,2-二甲基正丙氧基、2,2-二甲基正丙氧基、1-乙基正丙氧基、正己基氧基、1-甲基正戊基氧基、2-甲基正戊基氧基、3-甲基正戊基氧基、4-甲基正戊基氧基、1,1-二甲基正丁氧基、1,2-二甲基正丁氧基、1,3-二甲基正丁氧基、2,2-二甲基正丁氧基、2,3-二甲基正丁氧基、3,3-二甲基正丁氧基、1-乙基正丁氧基、2-乙基正丁氧基、1,1,2-三甲基正丙氧基、1,2,2-三甲基正丙氧基、1-乙基-1-甲基正丙氧基、及1-乙基-2-甲基正丙氧基、环戊基氧基、环己基氧基、降冰片基氧基、金刚烷基氧基、金刚烷甲基氧基、金刚烷乙基氧基、四环癸基氧基、三环癸基氧基。
上述脂肪族环优选具有至少1个不饱和键(例如双键、三键)。上述脂肪族环优选具有1~3个不饱和键。上述脂肪族环优选具有1个或2个不饱和键。上述不饱和键优选为双键。
作为包含上述可以被取代基取代的脂肪族环的化合物的具体例,可举出以下记载的化合物。也可举出下述具体例的羧基替换为羟基、氨基或硫醇基而成的化合物作为具体例。
上文记载的化合物在聚合物末端反应后还具有羧基的情况下,该羧基与醇化合物可以进行反应。上述醇化合物可以为上述抗蚀剂下层膜形成用组合物所包含的有机溶剂。
作为上述醇的具体例,可举出丙二醇单甲基醚、丙二醇单乙基醚、甲醇、乙醇、1-丙醇及2-丙醇。
<化合物(A)[2])>
上述化合物(A)优选由下述式(1)及式(2)表示。
(式(1)及式(2)中,R1表示可具有取代基的碳原子数1~6的烷基、苯基、吡啶基、卤代基或羟基,R2表示氢原子、碳原子数1~6的烷基、羟基、卤代基或-C(=O)O-X所示的酯基,X表示可具有取代基的碳原子数1~6的烷基,R3表示氢原子、碳原子数1~6的烷基、羟基或卤代基,R4表示直接连接键、或碳原子数1~8的二价有机基团,R5表示碳原子数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。)
有关上述式(1)及式(2)的内容,将国际公开第2015/163195号公报中记载的全部公开内容援用到本申请中。
上述式(1)及式(2)表示的上述聚合物末端结构可以通过上述聚合物、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)及式(2a)的符号的含义如上述式(1)及式(2)中所说明的那样。)
作为上述式(1a)表示的化合物,可以举出例如下述式表示的化合物。
作为上述式(2a)表示的化合物,可以举出例如下述式表示的化合物。
上文记载的化合物在聚合物末端反应后还具有羧基的情况下,该羧基与醇化合物可以进行反应。上述醇化合物可以为上述抗蚀剂下层膜形成用组合物所包含的有机溶剂。
作为上述醇的具体例,可举出丙二醇单甲基醚、丙二醇单乙基醚、甲醇、乙醇、1-丙醇及2-丙醇。
<产酸剂>
作为可作为任选成分而包含于本发明的抗蚀剂下层膜形成用组合物中的产酸剂,可以使用热产酸剂、光产酸剂中的任意产酸剂,但优选使用热产酸剂。作为热产酸剂,可举出例如,对甲苯磺酸、三氟甲磺酸、吡啶鎓对甲苯磺酸盐(对甲苯磺酸吡啶鎓)、对羟基苯磺酸吡啶鎓(对苯酚磺酸吡啶鎓盐)、三氟甲磺酸吡啶鎓、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、N-甲基吗啉-对甲苯磺酸、N-甲基吗啉-对羟基苯磺酸、N-甲基吗啉-5-磺基水杨酸等磺酸化合物及羧酸化合物。
作为上述光产酸剂,可举出鎓盐化合物、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,可举出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,以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,可举出例如N-(三氟甲磺酰基氧基)琥珀酰亚胺、N-(九氟正丁烷磺酰基氧基)琥珀酰亚胺、N-(樟脑磺酰基氧基)琥珀酰亚胺及N-(三氟甲磺酰基氧基)萘二甲酰亚胺等。
作为二磺酰基重氮甲烷化合物,可举出例如,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,相对于下述交联剂,该产酸剂的含有比例例如为0.1质量%~50质量%,优选为1质量%~30质量%。
<交联剂>
作为可作为任选成分而包含于本发明的抗蚀剂下层膜形成用组合物中的交联剂,可举出例如,六甲氧基甲基三聚氰胺、四甲氧基甲基苯胍胺、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)脲及1,1,3,3-四(甲氧基甲基)脲。
另外,本申请的交联剂也可以为国际公开第2017/187969号公报中记载的、在1分子中具有2~6个的与氮原子键合的下述式(1d)表示的取代基的含氮化合物。
(式(1d)中,R1表示甲基或乙基。)
在1分子中具有2~6个上述式(1d)表示的取代基的含氮化合物可以为下述式(1E)表示的甘脲衍生物。
(式(1E)中,4个R1各自独立地表示甲基或乙基,R2及R3各自独立地表示氢原子、碳原子数1~4的烷基或苯基。)
作为上述式(1E)表示的甘脲衍生物,可举出例如下述式(1E-1)~式(1E-6)表示的化合物。
在1分子中具有2~6个上述式(1d)表示的取代基的含氮化合物可如下得到:使在1分子中具有2~6个的与氮原子键合的下述式(2d)表示的取代基的含氮化合物、和下述式(3d)表示的至少1种化合物进行反应。
(式(3d)中,R1表示甲基或乙基,式(2d)中,R4表示碳原子数1~4的烷基。)
上述式(1E)表示的甘脲衍生物可通过使下述式(2E)表示的甘脲衍生物与上述式(3d)表示的至少1种化合物进行反应而得到。
在1分子中具有2~6个上述式(2d)表示的取代基的含氮化合物例如为下述式(2E)表示的甘脲衍生物。
(式(2E)中,R2及R3各自独立地表示氢原子、碳原子数1~4的烷基或苯基,R4各自独立地表示碳原子数1~4的烷基。)
作为上述式(2E)表示的甘脲衍生物,可举出例如下述式(2E-1)~式(2E-4)表示的化合物。此外,作为上述式(3d)表示的化合物,可举出例如下述式(3d-1)及式(3d-2)表示的化合物。
关于上述在1分子中具有2~6个的与氮原子键合的下述式(1d)表示的取代基的含氮化合物相关的内容,将WO2017/187969号公报的全部公开内容援用到本申请中。
在使用上述交联剂的情况下,相对于上述反应产物,该交联剂的含有比例例如为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、进一步提高针对表面不均的涂布性,可以进一步添加表面活性剂。作为表面活性剂,可以举出例如,聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯鲸蜡基醚、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、聚氧乙烯壬基苯酚醚等聚氧乙烯烷基烯丙基醚类、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系表面活性剂、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)等氟系表面活性剂、有机硅氧烷聚合物KP341(信越化学工业(株)制)等。相对于本发明的抗蚀剂下层膜形成用组合物的全部固体成分,这些表面活性剂的混配量通常为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。
本发明的抗蚀剂下层膜形成用组合物优选为在电子射线(EB)描绘工序及EUV曝光工序中使用的、电子射线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于半导体基板上并进行烧成而制造。
本发明涉及的抗蚀剂下层膜优选为电子射线抗蚀剂下层膜或EUV抗蚀剂下层膜。
作为涂布本发明的抗蚀剂下层膜形成用组合物的半导体基板,可举出例如,硅晶片、锗晶片、以及砷化镓、磷化铟、氮化镓、氮化铟、氮化铝等化合物半导体晶片。
在使用表面上形成有无机膜的半导体基板的情况下,该无机膜可通过例如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)来形成。作为上述无机膜,可举出例如,多晶硅膜、氧化硅膜、氮化硅膜、BPSG(Boro-Phospho Silicate Glass,硼磷硅玻璃)膜、氮化钛膜、氮氧化钛膜、钨膜、氮化镓膜及砷化镓膜。
在这样的半导体基板上,利用旋转器、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,可从烘烤温度100℃~400℃、烘烤时间0.3分钟~60分钟中适宜选择。优选烘烤温度120℃~350℃、烘烤时间0.5分钟~30分钟,更优选烘烤温度150℃~300℃、烘烤时间0.8分钟~10分钟。
作为所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)、或0.005μm(5nm)~0.02μm(20nm)。在烘烤时的温度低于上述范围的情况下,交联变得不充分。另一方面,在烘烤时的温度高于上述范围的情况下,有时抗蚀剂下层膜因热而分解。
<已图案化的基板的制造方法、半导体装置的制造方法>
已图案化的基板的制造方法经由以下的工序。通常是在抗蚀剂下层膜上形成光致抗蚀剂层而制造的。作为在抗蚀剂下层膜上利用本身已知的方法涂布并烧成而形成的光致抗蚀剂,只要是对用于曝光的光敏感的光致抗蚀剂即可,没有特别限定。可以使用负型光致抗蚀剂及正型光致抗蚀剂中的任意光致抗蚀剂。有下述光致抗蚀剂:由酚醛清漆树脂和1,2-萘醌重氮磺酸酯组成的正型光致抗蚀剂;由具有在酸的作用下分解而使碱溶解速度上升的基团的粘结剂和光产酸剂组成的化学增强型光致抗蚀剂;由在酸的作用下分解而使光致抗蚀剂的碱溶解速度上升的低分子化合物、碱溶性粘结剂和光产酸剂组成的化学增强型光致抗蚀剂;以及由具有在酸的作用下分解而使碱溶解速度上升的基团的粘结剂、在酸的作用下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组成的化学增强型光致抗蚀剂;含有金属元素的抗蚀剂等。可举出例如,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,可以举出例如,Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)、Proc.SPIE,Vol.3999,365-374(2000)中记载的那样的、含氟原子聚合物类光致抗蚀剂。另外,可以为所谓的含有金属的含金属抗蚀剂(金属抗蚀剂)。作为具体例,可以使用WO2019/188595、WO2019/187881、WO2019/187803、WO2019/167737、WO2019/167725、WO2019/187445、WO2019/167419、WO2019/123842、WO2019/054282、WO2019/058945、WO2019/058890、WO2019/039290、WO2019/044259、WO2019/044231、WO2019/026549、WO2018/193954、WO2019/172054、WO2019/021975、WO2018/230334、WO2018/194123、日本特开2018-180525、WO2018/190088、日本特开2018-070596、日本特开2018-028090、日本特开2016-153409、日本特开2016-130240、日本特开2016-108325、日本特开2016-047920、日本特开2016-035570、日本特开2016-035567、日本特开2016-035565、日本特开2019-101417、日本特开2019-117373、日本特开2019-052294、日本特开2019-008280、日本特开2019-008279、日本特开2019-003176、日本特开2019-003175、日本特开2018-197853、日本特开2019-191298、日本特开2019-061217、日本特开2018-045152、日本特开2018-022039、日本特开2016-090441、日本特开2015-10878、日本特开2012-168279、日本特开2012-022261、日本特开2012-022258、日本特开2011-043749、日本特开2010-181857、日本特开2010-128369、WO2018/031896、日本特开2019-113855、WO2017/156388、WO2017/066319、日本特开2018-41099、WO2016/065120、WO2015/026482、日本特开2016-29498、日本特开2011-253185等中记载的抗蚀剂组合物、放射线敏感性树脂组合物、基于有机金属溶液的高分辨率图案化组合物等所谓的抗蚀剂组合物、含有金属的抗蚀剂组合物,但并不限定于此。
作为抗蚀剂组合物,可举出例如以下抗蚀剂组合物。
活性光线敏感性或放射线敏感性树脂组合物,其包含树脂A、及通式(1)表示的化合物,所述树脂A具有重复单元,该重复单元具有利用在酸的作用下脱离的保护基对极性基团进行了保护而得到的酸分解性基团的。
通式(1)中,m表示1~6的整数。
R1及R2各自独立地表示氟原子或全氟烷基。
L1表示-O-、-S-、-COO-、-SO2-或-SO3-。
L2表示可具有取代基的亚烷基或单键。
W1表示可具有取代基的环状有机基团。
M+表示阳离子。
用于极紫外线或电子射线光刻的含有金属的膜形成用组合物,其含有具有金属-氧共价键的化合物和溶剂,构成上述化合物的金属元素属于元素周期表第3族~第15族的第3周期~第7周期。
放射线敏感性树脂组合物,其含有:具有下述式(1)表示的第1结构单元及由下述式(2)表示且包含酸解离性基团的第2结构单元的聚合物;和产酸剂。
(式(1)中,Ar是从碳原子数6~20的芳烃除去(n+1)个氢原子而得到的基团。R1为羟基、硫烷基或碳原子数1~20的1价有机基团。n为0~11的整数。在n为2以上的情况下,多个R1相同或不同。R2为氢原子、氟原子、甲基或三氟甲基。
式(2)中,R3为包含上述酸解离性基团的碳原子数1~20的1价基团。Z为单键、氧原子或硫原子。R4为氢原子、氟原子、甲基或三氟甲基。)
抗蚀剂组合物,其含有树脂(A1);和产酸剂,所述树脂(A1)包含具有环状碳酸酯结构的结构单元、式(II)表示的结构单元及具有酸不稳定基团的结构单元。
[式(II)中,
R2表示可具有卤素原子的碳原子数1~6的烷基、氢原子或卤素原子,X1表示单键、-CO-O-*或-CO-NR4-*,*表示与-Ar的连接键,R4表示氢原子或碳原子数1~4的烷基,Ar表示可具有选自由羟基及羧基组成的组中的1个以上基团的碳原子数6~20的芳香族烃基。]
抗蚀剂组合物,其为通过曝光而产生酸、在显影液中的溶解性在酸的作用下变化的抗蚀剂组合物,其特征在于,
含有在显影液中的溶解性在酸的作用下变化的基材成分(A)及相对于碱显影液显示出分解性的氟添加剂成分(F),
上述氟添加剂成分(F)含有氟树脂成分(F1),所述氟树脂成分(F1)具有包含碱解离性基团的结构单元(f1)、和包含下述通式(f2-r-1)表示的基团的结构单元(f2)。
[式(f2-r-1)中,Rf21各自独立地为氢原子、烷基、烷氧基、羟基、羟基烷基或氰基。n”为0~2的整数。*为连接键。]
抗蚀剂组合物,其中,上述结构单元(f1)包含下述通式(f1-1)表示的结构单元、或下述通式(f1-2)表示的结构单元。
[式(f1-1)及(f1-2)中,R各自独立地为氢原子、碳原子数1~5的烷基或碳原子数1~5的卤代烷基。X为不具有酸解离性部位的2价连接基团。Aaryl为可具有取代基的2价的芳香族环式基团。X01为单键或2价连接基团。R2各自独立地为具有氟原子的有机基团。]
作为抗蚀剂材料,可举出例如以下抗蚀剂材料。
抗蚀剂材料,其包含具有下述式(a1)或(a2)表示的重复单元的聚合物。
(式(a1)及(a2)中,RA为氢原子或甲基。X1为单键或酯基。X2为直链状、支链状或环状的碳原子数1~12的亚烷基或者碳原子数6~10的亚芳基,构成该亚烷基的亚甲基的一部分可以被醚基、酯基或含有内酯环的基团取代,另外,X2中所含的至少1个氢原子被溴原子取代。X3为单键、醚基、酯基或者碳原子数1~12的直链状、支链状或环状的亚烷基,构成该亚烷基的亚甲基的一部分可以被醚基或酯基取代。Rf1~Rf4各自独立地为氢原子、氟原子或三氟甲基,但至少1个为氟原子或三氟甲基。另外,Rf1及Rf2可以结合而形成羰基。R1~R5各自独立地为直链状、支链状或环状的碳原子数1~12的烷基、直链状、支链状或环状的碳原子数2~12的烯基、碳原子数2~12的炔基、碳原子数6~20的芳基、碳原子数7~12的芳烷基或者碳原子数7~12的芳基氧基烷基,这些基团的氢原子的一部分或全部可以被羟基、羧基、卤素原子、氧代基、氰基、酰胺基、硝基、磺内酯基、磺基或含有锍盐的基团取代,构成这些基团的亚甲基的一部分可以被醚基、酯基、羰基、碳酸酯基或磺酸酯基取代。另外,R1与R2可以键合而与它们所键合的硫原子一起形成环。)
抗蚀剂材料,其包含基础树脂,所述基础树脂包含含有下述式(a)表示的重复单元的聚合物。
(式(a)中,RA为氢原子或甲基。R1为氢原子或酸不稳定基团。R2为直链状、支链状或环状的碳原子数1~6的烷基、或者除溴以外的卤素原子。X1为单键或亚苯基、或者酯基或可以包含内酯环的直链状、支链状或环状的碳原子数1~12的亚烷基。X2为-O-、-O-CH2-或-NH-。m为1~4的整数。n为0~3的整数。)
作为抗蚀剂膜,可举出例如以下抗蚀剂膜。
(i)抗蚀剂膜,其包含基础树脂,所述基础树脂包含下述式(a1)表示的重复单元和/或下述式(a2)表示的重复单元、以及通过曝光而产生键合于聚合物主链的酸的重复单元。
(式(a1)及(a2)中,RA各自独立地为氢原子或甲基。R1及R2各自独立地为碳原子数4~6的叔烷基。R3各自独立地为氟原子或甲基。m为0~4的整数。X1为单键、亚苯基或亚萘基、或者包含选自酯键、内酯环、亚苯基及亚萘基中的至少1种的碳原子数1~12的连接基团。X2为单键、酯键或酰胺键。)
作为涂覆溶液,可举出例如以下例子。
作为含有金属的抗蚀剂组合物,例如一种涂层,其包含通过金属碳键和/或金属羧酸盐键而具有有机配体的金属氧代-羟基(oxo-hydroxo)网络。
基于无机氧代/羟基的组合物。
一种涂覆溶液,其包含:有机溶剂;第一有机金属组合物;和水解性的金属化合物,所述第一有机金属组合物,其由式RzSnO(2-(z/2)-(x/2))(OH)x(其中,0<z≤2以及0<(z+x)≤4)、式R’nSnX4-n(其中,n=1或2)、或它们的混合物表示,其中,R及R’独立地为具有1~31个碳原子的烃基,并且,X为具有针对Sn的水解性键的配体或它们的组合;所述水解性的金属化合物,其由式MX’v(其中,M为选自元素周期表的第2~16族中的金属,v=2~6的数,并且,X’为具有水解性的M-X键的配体或它们的组合)表示。
一种涂覆溶液,其为包含有机溶剂和式RSnO(3/2-x/2)(OH)x(式中,0<x<3)表示的第1有机金属化合物的涂覆溶液,在上述溶液中包含约0.0025M~约1.5M的锡,R为具有3~31个碳原子的烷基或环烷基,上述烷基或环烷基在仲碳原子或叔碳原子处与锡键合。
一种无机图案形成用前体水溶液,其是包含水、金属亚氧化物阳离子、多原子无机阴离子、和包含过氧化物基团而成的放射线敏感配体的混合物而形成的。
曝光通过用于形成规定图案的掩模(中间掩膜(reticle))来进行,例如可使用i射线、KrF准分子激光、ArF准分子激光、EUV(极紫外线)或EB(电子射线),但本发明的抗蚀剂下层膜形成用组合物优选应用于EUV(极紫外线)曝光用途。在显影中,可使用碱显影液,可从显影温度5℃~50℃、显影时间10秒~300秒中适宜选择。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、乙基胺、正丙基胺等伯胺类、二乙基胺、二正丁基胺等仲胺类、三乙基胺、甲基二乙基胺等叔胺类、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。此外,也可以向上述碱类的水溶液中添加适当量的异丙醇等醇类、非离子系等的表面活性剂来使用。它们之中优选的显影液为季铵盐,进一步优选为四甲基氢氧化铵及胆碱。此外,也可以向这些显影液中加入表面活性剂等。也可以采用下述方法:代替碱显影液而利用乙酸丁酯等有机溶剂进行显影,使光致抗蚀剂的碱溶解速度未提高的部分显影。经由上述工序,能够制造上述抗蚀剂已被图案化的基板。
接着,将所形成的抗蚀剂图案作为掩模,对上述抗蚀剂下层膜进行干式蚀刻。此时,在所使用的半导体基板的表面形成有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,经由利用本身已知的方法(干式蚀刻法等)对基板进行加工的工序,从而能够制造半导体装置。
实施例
以下,举出实施例及比较例来更具体地说明本发明,但本发明并不限定于下述实施例。
本说明书的下述合成例1~合成例2、比较合成例1所示的聚合物的重均分子量是利用凝胶渗透色谱(以下,简称为GPC)得到的测定结果。在测定中,使用东ソー(株)制GPC装置,测定条件等如下所述。
GPC柱:Shodex KF803L、Shodex KF802、Shodex KF801〔注册商标〕(昭和电工(株))
柱温:40℃
溶剂:N,N-二甲基甲酰胺(DMF)
流量:0.6ml/分钟
标准试样:聚苯乙烯(東ソー(株)制)
<合成例1>
将作为聚合物1的原料的单烯丙基二缩水甘油基异氰脲酸(四国化成工业株式会社制)4.00g、双(4-羟基-3,5-二甲基苯基)砜(东京化成工业(株)制)3.72g、5-降冰片烯-2,3-二甲酸酐(东京化成工业(株)制)0.70g、2,6-二叔丁基对甲酚(东京化成工业(株)制)0.13g及四丁基溴化鏻(东京化成工业(株)制)0.36g加入丙二醇单甲基醚26.76g中,使其溶解。对反应容器进行氮置换后,在105℃下进行24小时反应,得到聚合物1的溶液。进行了GPC分析,结果,所得到的聚合物1按标准聚苯乙烯换算计,重均分子量为7600,分散度为3.2。将聚合物1中存在的结构示于下述式。
<合成例2>
将作为聚合物2的原料的单烯丙基二缩水甘油基异氰脲酸(四国化成工业株式会社制)4.00g、双(4-羟基-3,5-二甲基苯基)砜(东京化成工业(株)制)3.72g、1-羟基金刚烷甲酸(东京化成工业(株)制)0.77g、2,6-二叔丁基对甲酚(东京化成工业(株)制)0.13g及四丁基溴化鏻(东京化成工业(株)制)0.36g加入丙二醇单甲基醚26.96g中,使其溶解。对反应容器进行氮置换后,在105℃下进行24小时反应,得到聚合物2的溶液。进行了GPC分析,结果,所得到的聚合物2按标准聚苯乙烯换算计,重均分子量为7400,分散度为3.4。将聚合物2中存在的结构示于下述式。
<合成例3>
将作为聚合物3的原料的单烯丙基二缩水甘油基异氰脲酸(四国化成工业株式会社制)4.00g、双(4-羟基-3,5-二甲基苯基)砜(东京化成工业(株)制)3.72g、3-羟基-1-金刚烷甲酸(东京化成工业(株)制)0.84g、2,6-二叔丁基对甲酚(东京化成工业(株)制)0.13g及四丁基溴化鏻(东京化成工业(株)制)0.36g加入丙二醇单甲基醚27.17g中,使其溶解。对反应容器进行氮置换后,在105℃下进行24小时反应,得到聚合物3的溶液。进行了GPC分析,结果,所得到的聚合物3按标准聚苯乙烯换算计,重均分子量为7400,分散度为3.2。将聚合物3中存在的结构示于下述式。
<合成例4>
将作为聚合物4的原料的单烯丙基二缩水甘油基异氰脲酸(四国化成工业株式会社制)4.00g、双(4-羟基-3,5-二甲基苯基)砜(东京化成工业(株)制)3.72g、4-甲基磺酰基苯甲酸(东京化成工业(株)制)0.86g、2,6-二叔丁基对甲酚(东京化成工业(株)制)0.13g及四丁基溴化鏻(东京化成工业(株)制)0.36g加入丙二醇单甲基醚36.29g中,使其溶解。对反应容器进行氮置换后,在105℃下进行24小时反应,得到聚合物4的溶液。进行了GPC分析,结果,所得到的聚合物4按标准聚苯乙烯换算计,重均分子量为6200,分散度为3.9。将聚合物4中存在的结构示于下述式。
<比较合成例1>
将作为比较聚合物1的原料的单烯丙基二缩水甘油基异氰脲酸(四国化成工业株式会社制)3.00g、双(4-羟基-3,5-二甲基苯基)砜(东京化成工业(株)制)3.94g、2,6-二叔丁基对甲酚(东京化成工业(株)制)0.10g及四丁基溴化鏻(东京化成工业(株)制)0.27g加入丙二醇单甲基醚21.93g中,使其溶解。对反应容器进行氮置换后,在105℃下进行24小时反应,得到比较聚合物1的溶液。进行了GPC分析,结果,所得到的比较聚合物1按标准聚苯乙烯换算计,重均分子量为6400,分散度为4.6。将比较聚合物1中存在的结构示于下述式。
(抗蚀剂下层膜的调制)
(实施例)
将上述合成例1~4及比较合成例1中得到的聚合物、交联剂、固化催化剂(产酸剂)、溶剂按表1及2所示的比例混合,利用0.1μm的氟树脂制过滤器进行过滤,由此分别调制成抗蚀剂下层膜形成用组合物的溶液。
在表1及2中,将四甲氧基甲基甘脲(日本サイテックインダストリーズ(株)制)简记为PL-LI,将Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione,tetrahydro-1,3,4,6-tetrakis[(2-methoxy-1-methylethoxy)methyl]-(四氢-1,3,4,6-四[(2-甲氧基-1-甲基乙氧基)甲基]-咪唑并[4,5-d]咪唑-2,5(1H,3H)-二酮)简记为PGME-PL,将对羟基苯磺酸吡啶鎓简记为PyPSA,将丙二醇单甲基醚乙酸酯简记为PGMEA,将丙二醇单甲基醚简记为PGME。各添加量以质量份示出。
表1
表2
(向光致抗蚀剂溶剂中的溶出试验)
将实施例1~8及比较例1的抗蚀剂下层膜形成用组合物分别用旋转器涂布至硅晶片上。在加热板上,在205℃下对该硅晶片进行60秒钟烘烤,得到膜厚为5nm的膜。将这些抗蚀剂下层膜浸渍在用于光致抗蚀剂的溶剂即丙二醇单甲基醚/丙二醇单甲基醚=70/30的混合溶液中,在膜厚变化为以下的情况下记为良,在膜厚变化为/>以上的情况下记为不良,将其结果示于表3中。
(成膜性试验)
将实施例1~8及比较例1的抗蚀剂下层膜形成用组合物分别用旋转器涂布至硅晶片上。在加热板上,在205℃下对该硅晶片进行60秒钟烘烤,得到膜厚为5nm及3.5nm的膜。对于这些抗蚀剂下层膜,使用原子力显微镜(AFM)测定表面粗糙度(Sa),在与比较例1相比为良好的情况下记为良,在与比较例1相比恶化的情况下记为不良,将其结果示于表3中。
表3
(抗蚀剂图案化评价)
〔利用电子射线描绘装置实施的抗蚀剂图案的形成试验〕
使用旋转器,将抗蚀剂下层膜形成用组合物分别涂布至硅晶片上。在加热板上,在205℃下对该硅晶片进行60秒钟烘烤,得到膜厚为5nm的抗蚀剂下层膜。在该抗蚀剂下层膜上旋涂EUV用正型抗蚀剂溶液,在110℃下加热60秒钟,形成了EUV抗蚀剂膜。针对该抗蚀剂膜,使用电子射线描绘装置(ELS-G130),在规定的条件下进行了曝光。曝光后,在90℃下进行60秒钟烘烤(PEB),在冷却板上冷却至室温,使用2.38%四甲基氢氧化铵水溶液(东京应化工业(株)制,商品名NMD-3)作为光致抗蚀剂用显影液,进行60秒钟的旋覆浸没式显影。形成了线尺寸为15nm~27nm的抗蚀剂图案。在抗蚀剂图案的长度测量中,使用了扫描型电子显微镜((株)日立ハイテクノロジーズ制,CG4100)。
对于如上所述地得到的光致抗蚀剂图案,根据能否形成22nm的线与间隔(L/S)而进行了评价。在实施例1、实施例3及比较例1的所有情况下,确认了22nmL/S图案的形成。另外,将形成了22nm线/44nm间距(线与间隔(L/S=1/1)的电荷量作为最合适的照射能量,此时的照射能量(μC/cm2)的值越小,表示抗蚀剂的敏感度越高,实施例1及3的结果显示为低于比较例1的值,表明了敏感度的提高。另外,从图案上部进行观察,确认了在抗蚀剂图案的镜头内观察不到倒塌(塌陷)的最小CD尺寸。该值越小,表示与抗蚀剂的密合性越良好,实施例1及3的结果与比较例1相比,最小CD尺寸的值小,表明了与抗蚀剂的良好的密合性。
表4
产业可利用性
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能够形成所希望的抗蚀剂图案的抗蚀剂下层膜的组合物、以及使用了该抗蚀剂下层膜形成用组合物的带有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)
2.根据权利要求1所述的抗蚀剂下层膜形成用组合物,所述化合物(A)包含可以被取代基取代的脂肪族环。
3.根据权利要求2所述的抗蚀剂下层膜形成用组合物,所述脂肪族环为碳原子数3~10的单环式或多环式脂肪族环。
4.根据权利要求2所述的抗蚀剂下层膜形成用组合物,所述脂肪族环为双环式环或三环式环。
5.根据权利要求2~4中任一项所述的抗蚀剂下层膜形成用组合物,所述取代基选自羟基、直链状或支链状的碳原子数1~10的烷基、碳原子数1~20的烷氧基、可以被氧原子中断的碳原子数1~10的酰基氧基及羧基。
7.根据权利要求1~6中任一项所述的抗蚀剂下层膜形成用组合物,所述聚合物包含由所述化合物(B)、和能与所述化合物(B)反应的化合物(C)衍生的重复单元结构,所述化合物(C)具有杂环结构。
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,所述Y1为磺酰基。
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,其还包含产酸剂。
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,其还包含交联剂。
11.一种抗蚀剂下层膜,其特征在于,其是由权利要求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。
12.一种被图案化了的基板的制造方法,其包括: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从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从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所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从而进行图案化的工序。
13.一种半导体装置的制造方法,其特征在于,包括:
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的光或电子射线的照射和其后的显影而形成抗蚀剂图案的工序;
通过隔着所形成的所述抗蚀剂图案对所述抗蚀剂下层膜进行蚀刻,从而形成被图案化了的抗蚀剂下层膜的工序;和
利用被图案化了的所述抗蚀剂下层膜而对半导体基板进行加工的工序。
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