CN104246614B - 含有添加剂的含硅极紫外抗蚀剂下层膜形成用组合物 - Google Patents
含有添加剂的含硅极紫外抗蚀剂下层膜形成用组合物 Download PDFInfo
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- CN104246614B CN104246614B CN201380021388.7A CN201380021388A CN104246614B CN 104246614 B CN104246614 B CN 104246614B CN 201380021388 A CN201380021388 A CN 201380021388A CN 104246614 B CN104246614 B CN 104246614B
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZESWBFKRPIRQCD-UHFFFAOYSA-N trimethoxy-(4-methoxyphenyl)silane Chemical compound COC1=CC=C([Si](OC)(OC)OC)C=C1 ZESWBFKRPIRQCD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- NBNZEBUNZGWIRJ-UHFFFAOYSA-N triphenylsulfanium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NBNZEBUNZGWIRJ-UHFFFAOYSA-N 0.000 description 1
- 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
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
本发明的目的在于提供抗蚀剂形状良好的极紫外抗蚀剂下层膜形成用组合物。于是,提供了一种极紫外光刻用抗蚀剂下层膜形成用组合物,含有聚硅氧烷A和水解性硅烷化合物b,所述聚硅氧烷A含有水解性硅烷a的水解缩合物,所述水解性硅烷化合物b具有磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构。还提供了一种极紫外光刻用抗蚀剂下层膜形成用组合物,含有聚硅氧烷B,所述聚硅氧烷B含有水解性硅烷a与水解性硅烷化合物b的水解缩合物,所述水解性硅烷化合物b具有磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构。聚硅氧烷(A)是四烷氧基硅烷和烷基三烷氧基硅烷和芳基三烷氧基硅烷的共水解缩合物。
Description
技术领域
本发明涉及用于在制造半导体装置时使用的基板和抗蚀剂(例如、极紫外(下文中也称作“EUV”)抗蚀剂)之间形成下层膜的组合物。更具体地说,涉及用于形成在半导体装置制造的光刻工序中作为抗蚀剂的下层使用的下层膜的光刻用抗蚀剂下层膜形成用组合物。此外,涉及使用该下层膜形成用组合物形成抗蚀剂图案的形成方法。
背景技术
一直以来,在半导体装置的制造中,使用光致抗蚀剂通过光刻进行微细加工。上述微细加工为在硅晶片等半导体基板上形成光致抗蚀剂的薄膜,在其上介由描绘有半导体器件图案的掩模图案来照射紫外线等活性光线,进行显影,将所得的光致抗蚀剂图案作为保护膜对基板进行蚀刻处理,从而在基板表面形成与上述图案对应的微细凹凸的加工法。然而,近年来,半导体器件的高集成度化进展,所使用的活性光线也有从KrF准分子激光(248nm)向ArF准分子激光(193nm)、极紫外光(EUV光,13.5nm)短波长化发展的倾向。
需要比以往更好地控制图形(抗蚀剂形状)、提高与基板的密合性。
此外,作为半导体基板与光致抗蚀剂之间的下层膜,使用了作为包含硅等金属元素的硬掩模而已知的膜。在该情况下,对于抗蚀剂和硬掩模,由于其构成成分有大的差异,因此它们的通过干蚀刻而被除去的速度很大程度依赖于干蚀刻中使用的气体种类。而且,通过适当地选择气体种类,不会导致光致抗蚀剂的膜厚的大幅减少,能够通过干蚀刻除去硬掩模。这样,在近年来的半导体装置的制造中,为了实现各种效果,渐渐在半导体基板与光致抗蚀剂之间配置抗蚀剂下层膜(参照专利文献1、2)。
而且,迄今为止也进行了抗蚀剂下层膜用组合物的研究,但从其要求特性的多样性等出发,期望开发出抗蚀剂下层膜用的新材料。
现有技术文献
专利文献
专利文献1:日本特开2008-076889
专利文献2:日本特开2010-237667
发明内容
发明所要解决的课题
本发明的目的是提供能够利用矩形抗蚀剂图案进行微细的基板加工,可以用于制造半导体装置的形成EUV光刻用抗蚀剂下层膜的组合物。本发明的目的,详细地说,是提供用于形成可作为硬掩模使用的抗蚀剂下层膜的、形成光刻用抗蚀剂下层膜的组合物。此外,本发明的目的是提供EUV抗蚀剂的曝光灵敏度提高,不发生与抗蚀剂的混合,与抗蚀剂相比具有大的干蚀刻速度,用EUV光曝光时释气发生少的光刻用抗蚀剂下层膜和用于形成该下层膜的形成抗蚀剂下层膜的组合物。
用于解决课题的方法
本发明中,作为方案1,是一种极紫外光刻用抗蚀剂下层膜形成用组合物,含有聚硅氧烷A和水解性硅烷化合物b,所述聚硅氧烷A含有水解性硅烷a的水解缩合物,所述水解性硅烷化合物b具有磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构。
作为方案2,是一种极紫外光刻用抗蚀剂下层膜形成用组合物,含有聚硅氧烷B,所述聚硅氧烷B含有水解性硅烷a与水解性硅烷化合物b的水解缩合物,所述水解性硅烷化合物b具有磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构。
作为方案3,是如方案1或2所述的抗蚀剂下层膜形成用组合物,水解性硅烷a是选自四烷氧基硅烷、烷基三烷氧基硅烷和芳基三烷氧基硅烷中的至少1种水解性硅烷。
作为方案4,是如方案3所述的抗蚀剂下层膜形成用组合物,所述烷基三烷氧基硅烷是甲基三烷氧基硅烷。。
作为方案5,是如方案3或4所述的抗蚀剂下层膜形成用组合物,所述芳基三烷氧基硅烷是苯基三烷氧基硅烷。
作为方案6,是如方案1~5的任一项所述的抗蚀剂下层膜形成用组合物,所述水解性硅烷化合物b是下述通式(b-1)所表示的硅烷化合物,
R3-R2-R1-Si(R4)3 式(b-1)
上述式(b-1)中,R4表示碳原子数1~10的烷氧基,R1表示碳原子数1~10的亚烷基,R2是下述磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构
R3表示氢原子、碳原子数1~10的烷基、碳原子数1~10的氟烷基、碳原子数2~10的烯基、或碳原子数6~20的芳基。
作为方案7,是如方案1和方案3~6的任一项所述的抗蚀剂下层膜形成用组合物,所述聚硅氧烷A是以相对于四烷氧基硅烷70摩尔,烷基三烷氧基硅烷为10~35摩尔、芳基三烷氧基硅烷为2~25摩尔的比例使它们共水解、缩合而成的,
作为方案8,是如方案1~7的任一项所述的抗蚀剂下层膜形成用组合物,还含有酸化合物。
作为方案9,是如方案1~8的任一项所述的抗蚀剂下层膜形成用组合物,还含有水。
作为方案10,是如方案1~9的任一项所述的抗蚀剂下层膜形成用组合物,还含有铵化合物、环状铵化合物、环状胺化合物、或锍化合物。
作为方案11,是一种抗蚀剂下层膜,是通过将方案1~10的任一项所述的抗蚀剂下层膜形成用组合物涂布到半导体基板上并烘烤而得到。
作为方案12,是一种半导体装置的制造方法,包含以下工序:
将方案1~10的任一项所述的抗蚀剂下层膜形成用组合物涂布到半导体基板上、并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用组合物而形成抗蚀剂膜的工序,
使所述抗蚀剂膜曝光的工序,
在曝光后使抗蚀剂膜显影而得到图案化了的抗蚀剂膜的工序,
通过图案化了的抗蚀剂膜对抗蚀剂下层膜进行蚀刻的工序,以及
通过图案化了的抗蚀剂膜和抗蚀剂下层膜对半导体基板进行加工的工序。
作为方案13,是一种半导体装置的制造方法,包含以下工序:
在半导体基板上形成有机下层膜的工序,
在有机下层膜上涂布方案1~10的任一项所述的抗蚀剂下层膜形成用组合物、并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用组合物而形成抗蚀剂膜的工序,
使所述抗蚀剂膜曝光的工序,
在曝光后使抗蚀剂膜显影而得到图案化了的抗蚀剂膜的工序,
通过图案化了的抗蚀剂膜对抗蚀剂下层膜进行蚀刻的工序,
通过图案化了的抗蚀剂下层膜对有机下层膜进行蚀刻的工序,以及
通过图案化了的有机下层膜对半导体基板进行加工的工序。
作为方案14,是如方案12或13所述的制造方法,显影通过碱性水溶液或有机溶剂进行。
发明效果
本发明的抗蚀剂下层膜形成用组合物,由于含有水解性硅烷的水解缩合物,即含有聚有机硅氧烷结构,所以由该组合物形成的抗蚀剂下层膜,相对于在基板和基板上形成的有机下层膜的蚀刻时使用的氧系干蚀刻气体具有充分的耐蚀性,因而,在半导体装置的制造中能够发挥硬掩模和防反射膜的功能。
此外,本发明的抗蚀剂下层膜形成用组合物,由于具有所述特定结构的水解性硅烷化合物能够调整在极紫外抗蚀剂膜和下层膜之间的界面存在的光产酸剂所产生的酸的量的平衡,所以能够抑制该酸造成的抗蚀剂图案的形状不良。
此外,本发明的抗蚀剂下层膜形成用组合物,通过含有该水解性硅烷化合物,能够提高由该组合物形成的抗蚀剂下层膜和抗蚀剂膜之间的贴附性,并且由于该水解性硅烷化合物通过具有水解性的基团,能够导入聚有机硅氧烷结构,所以能够发挥抑制释气发生的效果。
具体实施方式
在本发明中,通过涂布法在基板上形成抗蚀剂下层膜,或者介由基板上的有机下层膜通过涂布法在其上形成抗蚀剂下层膜,在该抗蚀剂下层膜上形成抗蚀剂膜(例如,EUV抗蚀剂)。然后,通过曝光和显影来形成抗蚀剂图案,使用该抗蚀剂图案对抗蚀剂下层膜进行干蚀刻来进行图案的转印,按照该图案对基板进行加工,或者通过对有机下层膜进行蚀刻来进行图案转印,按照该有机下层膜进行基板加工。
在形成微细图案方面,为了防止图案倒塌而倾向于使抗蚀剂膜厚变薄。由于抗蚀剂的薄膜化,因而如果为了向存在于其下层的膜转印图案而进行的干蚀刻的蚀刻速度不高于上层的膜,则无法进行图案转印。在本发明中,在基板上,介由有机下层膜或不介由有机下层膜,在其上被覆本申请抗蚀剂下层膜(含有无机系硅系化合物),在其上依次被覆抗蚀剂膜(有机抗蚀剂膜)。通过选择蚀刻气体而使有机系成分的膜与无机系成分的膜的干蚀刻速度大不相同,使有机系成分的膜在氧系气体下干蚀刻速度高,无机系成分的膜在含卤气体下干蚀刻速度高。
例如形成抗蚀剂图案,用含卤气体对存在于其下层的本申请抗蚀剂下层膜进行干蚀刻,从而在抗蚀剂下层膜上转印图案,使用含卤气体按照该被转印到抗蚀剂下层膜的图案来进行基板加工。或者,使用被转印上图案的抗蚀剂下层膜,利用氧系气体对其下层的有机下层膜进行干蚀刻,从而对有机下层膜进行图案转印,使用含卤气体按照该被转印图案了的有机下层膜进行基板加工。
在本发明中,该抗蚀剂下层膜作为硬掩模起作用,结构中的烷氧基、酰氧基、卤基等水解性基团水解或部分水解,然后通过硅烷醇基的缩合反应而形成聚硅氧烷结构的聚合物。该聚有机硅氧烷结构具有作为硬掩模的充分的功能。
而且,聚有机硅氧烷结构(中间膜)在其下存在的有机下层膜的蚀刻、基板的加工(蚀刻)中作为硬掩模是有效的。即,对基板加工时、有机下层膜的氧系干蚀刻气体具有充分的耐干蚀刻性。
本发明中与聚硅氧烷一起使用的硅烷化合物,在极紫外抗蚀剂的光刻中能够使抗蚀剂形状为矩形。这是由于,由极紫外抗蚀剂中含有的光产酸剂产生的酸,如果存在于极紫外抗蚀剂和下层膜之间的界面,则抗蚀剂图案的底部有成为削脚(小脚,under cut)的倾向,进而如果极紫外抗蚀剂和下层膜之间的界面上存在的酸不足,则会成为拖脚(footing),本发明中所述硅烷化合物的添加,是为了将界面存在的酸中和(quenching)、或通过供给进行改善。因此,所述添加的硅烷化合物优选是能够通过光进行分解而形成碱的物质、或是能够捕捉硅烷化合物本身的碱性或由氢键产生的酸性的化合物。此外,添加的硅烷化合物优选是能够通过光产生二次电子或酸的化合物。通过这样添加硅烷化合物,能够调节界面上的酸的平衡。
此外,这些硅烷化合物对于改善与抗蚀剂的贴附性也有效。
并且,由于硅烷化合物具有水解性基,能够通过其硅醇基与聚硅氧烷结合,而导入聚硅氧烷,所以具有能够抑制曝光时释气发生的效果。
本发明是极紫外光刻用抗蚀剂下层膜形成用组合物,其含有含水解性硅烷(a)的水解缩合物的聚硅氧烷(A),和具有磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构的水解性硅烷化合物(b)。
此外,本发明是含有聚硅氧烷(B)的极紫外光刻用抗蚀剂下层膜形成用组合物,所述聚硅氧烷(B)含有水解性硅烷(a)与具有磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构的水解性硅烷化合物(b)之间的水解缩合物。
所述水解缩合物是聚硅氧烷,但也可以使用在获得水解缩合物时水解没有完全结束的水解物、部分水解物和/或硅烷化合物混合在水解缩合物中的混合物。
本发明的抗蚀剂下层膜形成用组合物含有所述聚硅氧烷(A)或聚硅氧烷(B),还含有溶剂。并且,可以作为任意成分,含有酸、水、醇、固化催化剂、产酸剂、其它有机聚合物、吸光性化合物、和表面活性剂等。
本发明的抗蚀剂下层膜形成用组合物中的固体成分,可以列举出例如0.1~50质量%、或0.1~30质量%、0.1~25质量%。这里的固体成分是从抗蚀剂下层膜形成用组合物的所有成分中除去溶剂成分后的成分。
固体成分中占据的聚硅氧烷(A)或聚硅氧烷(B)的比例是20质量%以上,例如50~99.999质量%、或60~99.99质量%、或70~99.5质量%。
此外,水解性硅烷化合物(b)可以相对于聚硅氧烷(A)以0.001~15质量%、或0.01~15质量%、或1~15质量%、或5~10质量%的范围添加。
本发明中使用的聚硅氧烷(A)是水解性硅烷(a)的水解缩合物,水解性硅烷(a)是选自四烷氧基硅烷、烷基三烷氧基硅烷、芳基三烷氧基硅烷中的水解性硅烷的共水解缩合物。聚硅氧烷(A)优选是四烷氧基硅烷和烷基三烷氧基硅烷和芳基三烷氧基硅烷之间的共水解缩合物。
四烷氧基硅烷是四甲氧基硅烷、四乙氧基硅烷、四异丙氧基硅烷、四丁氧基硅烷等硅烷化合物。
烷基三烷氧基硅烷的烷基是具有直链或支链的碳原子数1~10的烷基,可以列举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、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、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-甲基正丙基和1-乙基-2-甲基正丙基等。此外可以使用环状烷基,例如作为碳原子数1~10的环状烷基,可以列举出环丙基、环丁基、1-甲基-环丙基、2-甲基-环丙基、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、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-环丙基和2-乙基-3-甲基-环丙基等。
特别优选使用甲基。此外,水解基,可以列举出甲氧基、乙氧基、异丙氧基、丁氧基等。
芳基三烷氧基硅烷的芳基,可以列举出取代或非取代的苯基、萘基。特别优选是苯基。作为其取代基,可以列举出氟原子、氯原子、溴原子、碘原子等卤原子、甲氧基、乙氧基、正丙氧基、异丙氧基等烷氧基、甲氧基甲氧基、乙氧基乙氧基、甲氧基乙氧基、乙氧基甲氧基等烷氧基烷氧基。
此外,水解基,可以列举出甲氧基、乙氧基、异丙氧基、丁氧基等。
该芳基三烷氧基硅烷可以例示以下的。
上述式中X表示甲氧基、乙氧基、异丙氧基、丁氧基等水解性基。
聚硅氧烷(A),是相对于四烷氧基硅烷70摩尔,以烷基三烷氧基硅烷10~35摩尔、芳基三烷氧基硅烷0~25摩尔的比例进行共水解、缩合而成的。
此外,聚硅氧烷(A),优选是相对于四烷氧基硅烷70摩尔,以烷基三烷氧基硅烷10~35摩尔、芳基三烷氧基硅烷2~25摩尔的比例共水解、缩合而成的。
聚硅氧烷(A)的具体例可以例示以下的。
水解性硅烷(a)的水解缩合物(聚有机硅氧烷(A))可以获得重均分子量1000~1000000,或1000~100000的缩合物。它们的分子量为通过GPC分析,以聚苯乙烯换算得到的分子量。
GPC的测定条件例如可以如下:使用GPC装置(商品名HLC-8220GPC,东ソ一株式会社制),GPC柱(商品名ShodexKF803L,KF802,KF801,昭和电工制),柱温度使用40℃,洗脱液(洗脱溶剂)使用四氢呋喃,流量(流速)使用1.0ml/分钟,标准试样使用聚苯乙烯(昭和电工株式会社制)。
水解性基团水解时,相对于每1摩尔水解性基团使用0.5~100摩尔,优选为1~10摩尔的水。
此外,可以相对于每1摩尔水解性基团使用0.001~10摩尔,优选为0.001~1摩尔的水解催化剂。
进行水解和缩合时的反应温度通常为20~90℃。
水解可以进行完全水解,也可以进行部分水解。即,在水解缩合物中可以残存水解物、单体。
可以在水解缩合时使用催化剂。
作为水解催化剂,可举出金属螯合物、有机酸、无机酸、有机碱、无机碱。
作为水解催化剂的金属螯合物,可以举出例如三乙氧基·单(乙酰丙酮)合钛、三正丙氧基·单(乙酰丙酮)合钛、三异丙氧基·单(乙酰丙酮)合钛、三正丁氧基·单(乙酰丙酮)合钛、三仲丁氧基·单(乙酰丙酮)合钛、三叔丁氧基·单(乙酰丙酮)合钛、二乙氧基·双(乙酰丙酮)合钛、二正丙氧基·双(乙酰丙酮)合钛、二异丙氧基·双(乙酰丙酮)合钛、二正丁氧基·双(乙酰丙酮)合钛、二仲丁氧基·双(乙酰丙酮)合钛、二叔丁氧基·双(乙酰丙酮)合钛、单乙氧基·三(乙酰丙酮)合钛、单正丙氧基·三(乙酰丙酮)合钛、单异丙氧基·三(乙酰丙酮)合钛、单正丁氧基·三(乙酰丙酮)合钛、单仲丁氧基·三(乙酰丙酮)合钛、单叔丁氧基·三(乙酰丙酮)合钛、四(乙酰丙酮)合钛、三乙氧基·单(乙氧乙酰乙酰)合钛、三正丙氧基·单(乙氧乙酰乙酰)合钛、三异丙氧基·单(乙氧乙酰乙酰)合钛、三正丁氧基·单(乙氧乙酰乙酰)合钛、三仲丁氧基·单(乙氧乙酰乙酰)合钛、三叔丁氧基·单(乙氧乙酰乙酰)合钛、二乙氧基·双(乙氧乙酰乙酰)合钛、二正丙氧基·双(乙氧乙酰乙酰)合钛、二异丙氧基·双(乙氧乙酰乙酰)合钛、二正丁氧基·双(乙氧乙酰乙酰)合钛、二仲丁氧基·双(乙氧乙酰乙酰)合钛、二叔丁氧基·双(乙氧乙酰乙酰)合钛、单乙氧基·三(乙氧乙酰乙酰)合钛、单正丙氧基·三(乙氧乙酰乙酰)合钛、单异丙氧基·三(乙氧乙酰乙酰)合钛、单正丁氧基·三(乙氧乙酰乙酰)合钛、单仲丁氧基·三(乙氧乙酰乙酰)合钛、单叔丁氧基·三(乙氧乙酰乙酰)合钛、四(乙氧乙酰乙酰)合钛、单(乙酰丙酮)三(乙氧乙酰乙酰)合钛、双(乙酰丙酮)双(乙氧乙酰乙酰)合钛、三(乙酰丙酮)单(乙氧乙酰乙酰)合钛等钛螯合化合物;三乙氧基·单(乙酰丙酮)合锆、三正丙氧基·单(乙酰丙酮)合锆、三异丙氧基·单(乙酰丙酮)合锆、三正丁氧基·单(乙酰丙酮)合锆、三仲丁氧基·单(乙酰丙酮)合锆、三叔丁氧基·单(乙酰丙酮)合锆、二乙氧基·双(乙酰丙酮)合锆、二正丙氧基·双(乙酰丙酮)合锆、二异丙氧基·双(乙酰丙酮)合锆、二正丁氧基·双(乙酰丙酮)合锆、二仲丁氧基·双(乙酰丙酮)合锆、二叔丁氧基·双(乙酰丙酮)合锆、单乙氧基·三(乙酰丙酮)合锆、单正丙氧基·三(乙酰丙酮)合锆、单异丙氧基·三(乙酰丙酮)合锆、单正丁氧基·三(乙酰丙酮)合锆、单仲丁氧基·三(乙酰丙酮)合锆、单叔丁氧基·三(乙酰丙酮)合锆、四(乙酰丙酮)合锆、三乙氧基·单(乙氧乙酰乙酰)合锆、三正丙氧基·单(乙氧乙酰乙酰)合锆、三异丙氧基·单(乙氧乙酰乙酰)合锆、三正丁氧基·单(乙氧乙酰乙酰)合锆、三仲丁氧基·单(乙氧乙酰乙酰)合锆、三叔丁氧基·单(乙氧乙酰乙酰)合锆、二乙氧基·双(乙氧乙酰乙酰)合锆、二正丙氧基·双(乙氧乙酰乙酰)合锆、二异丙氧基·双(乙氧乙酰乙酰)合锆、二正丁氧基·双(乙氧乙酰乙酰)合锆、二仲丁氧基·双(乙氧乙酰乙酰)合锆、二叔丁氧基·双(乙氧乙酰乙酰)合锆、单乙氧基·三(乙氧乙酰乙酰)合锆、单正丙氧基·三(乙氧乙酰乙酰)合锆、单异丙氧基·三(乙氧乙酰乙酰)合锆、单正丁氧基·三(乙氧乙酰乙酰)合锆、单仲丁氧基·三(乙氧乙酰乙酰)合锆、单叔丁氧基·三(乙氧乙酰乙酰)合锆、四(乙氧乙酰乙酰)合锆、单(乙酰丙酮)三(乙氧乙酰乙酰)合锆、双(乙酰丙酮)双(乙氧乙酰乙酰)合锆、三(乙酰丙酮)单(乙氧乙酰乙酰)合锆等锆螯合化合物;三(乙酰丙酮)合铝、三(乙氧乙酰乙酰)合铝等铝螯合化合物;等。
作为水解催化剂的有机酸,可以举出例如乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、草酸、马来酸、甲基丙二酸、己二酸、癸二酸、没食子酸、丁酸、苯六甲酸、花生四烯酸、莽草酸、2-乙基己酸、油酸、硬脂酸、亚油酸、亚麻酸、水杨酸、苯甲酸、对氨基苯甲酸、对甲苯磺酸、苯磺酸、单氯乙酸、二氯乙酸、三氯乙酸、三氟乙酸、甲酸、丙二酸、磺酸、邻苯二甲酸、富马酸、柠檬酸、酒石酸等。
作为水解催化剂的无机酸,可以举出例如盐酸、硝酸、硫酸、氢氟酸、磷酸等。
作为水解催化剂的有机碱,可以举出例如吡啶、吡咯、哌嗪、吡咯烷、哌啶、皮考啉、三甲胺、三乙胺、单乙醇胺、二乙醇胺、二甲基单乙醇胺、单甲基二乙醇胺、三乙醇胺、二氮杂二环辛烷、二氮杂二环壬烷、二氮杂二环十一碳烯、四甲基氢氧化铵等。作为无机碱,可以举出例如氨、氢氧化钠、氢氧化钾、氢氧化钡、氢氧化钙等。这些催化剂中,优选金属螯合物、有机酸、无机酸,它们可以同时使用1种或者2种以上。
作为水解中使用的有机溶剂,可以举出例如正戊烷、异戊烷、正己烷、异己烷、正庚烷、异庚烷、2,2,4-三甲基戊烷、正辛烷、异辛烷、环己烷、甲基环己烷等脂肪族烃系溶剂;苯、甲苯、二甲苯、乙苯、三甲基苯、甲基乙基苯、正丙基苯、异丙基苯、二乙基苯、异丁基苯、三乙基苯、二异丙基苯、正戊基萘、三甲基苯等芳香族烃系溶剂;甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、正戊醇、异戊醇、2-甲基丁醇、仲戊醇、叔戊醇、3-甲氧基丁醇、正己醇、2-甲基戊醇、仲己醇、2-乙基丁醇、仲庚醇、庚醇-3、正辛醇、2-乙基己醇、仲辛醇、正壬醇、2,6-二甲基庚醇-4、正癸醇、仲十一醇、三甲基壬醇、仲十四烷醇、仲十七烷醇、苯酚、环己醇、甲基环己醇、3,3,5-三甲基环己醇、苄基醇、苯基甲基甲醇、双丙酮醇、甲酚等一元醇系溶剂;乙二醇、丙二醇、1,3-丁二醇、戊二醇-2,4、2-甲基戊二醇-2,4、己二醇-2,5、庚二醇-2,4、2-乙基己二醇-1,3、二甘醇、双丙甘醇、三甘醇、三丙二醇、甘油等多元醇系溶剂;丙酮、甲基乙基甲酮、甲基-正丙基甲酮、甲基-正丁基甲酮、二乙基甲酮、甲基异丁基甲酮、甲基-正戊基甲酮、乙基-正丁基甲酮、甲基-正己基甲酮、二异丁基甲酮、三甲基壬酮、环己酮、甲基环己酮、2,4-戊二酮、丙酮基丙酮、双丙酮醇、苯乙酮、葑酮等酮系溶剂;乙醚、异丙基醚、正丁基醚、正己基醚、2-乙基己基醚、环氧乙烷、1,2-环氧丙烷、二氧戊环、4-甲基二氧戊环、二烷、二甲基二烷、乙二醇单甲基醚、乙二醇单乙基醚、乙二醇二乙基醚、乙二醇单正丁基醚、乙二醇单正己基醚、乙二醇单苯基醚、乙二醇单-2-乙基丁基醚、乙二醇二丁基醚、二甘醇单甲基醚、二甘醇单乙基醚、二甘醇二乙基醚、二甘醇单正丁基醚、二甘醇二正丁基醚、二甘醇单正己基醚、乙氧基三甘醇、四甘醇二正丁基醚、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单丙基醚、丙二醇单丁基醚、双丙甘醇单甲基醚、双丙甘醇单乙基醚、双丙甘醇单丙基醚、双丙甘醇单丁基醚、三丙二醇单甲基醚、四氢呋喃、2-甲基四氢呋喃等醚系溶剂;碳酸二乙酯、乙酸甲酯、乙酸乙酯、γ-丁内酯、γ-戊内酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯、乙酸异丁酯、乙酸仲丁酯、乙酸正戊酯、乙酸仲戊酯、乙酸3-甲氧基丁酯、乙酸甲基戊酯、乙酸2-乙基丁酯、乙酸2-乙基己酯、乙酸苄酯、乙酸环己酯、乙酸甲基环己酯、乙酸正壬酯、乙酰乙酸甲酯、乙酰乙酸乙酯、乙酸乙二醇单甲基醚、乙酸乙二醇单乙基醚、乙酸二甘醇单甲基醚、乙酸二甘醇单乙基醚、乙酸二甘醇单正丁基醚、乙酸丙二醇单甲基醚、乙酸丙二醇单乙基醚、乙酸丙二醇单丙基醚、乙酸丙二醇单丁基醚、乙酸双丙甘醇单甲基醚、乙酸双丙甘醇单乙基醚、二乙酸乙二醇酯、乙酸甲氧基三甘醇酯、丙酸乙酯、丙酸正丁酯、丙酸异戊酯、草酸二乙酯、草酸二正丁酯、乳酸甲酯、乳酸乙酯、乳酸正丁酯、乳酸正戊酯、丙二酸二乙酯、邻苯二甲酸二甲酯、邻苯二甲酸二乙酯等酯系溶剂;N-甲基甲酰胺、N,N-二甲基甲酰胺、N,N-二乙基甲酰胺、乙酰胺、N-甲基乙酰胺、N,N-二甲基乙酰胺、N-甲基丙酰胺、N-甲基吡咯烷酮等含氮系溶剂;甲硫醚、乙硫醚、噻吩、四氢噻吩、二甲亚砜、环丁砜、1,3-丙磺酸内酯等含硫系溶剂等。这些溶剂可以使用1种或2种以上的组合。
从溶液的保存稳定性方面考虑,特别优选为丙酮、甲基乙基甲酮、甲基-正丙基甲酮、甲基-正丁基甲酮、二乙基甲酮、甲基-异丁基甲酮、甲基-正戊基甲酮、乙基-正丁基甲酮、甲基-正己基甲酮、二异丁基甲酮、三甲基壬酮、环己酮、甲基环己酮、2,4-戊二酮、丙酮基丙酮、双丙酮醇、苯乙酮、葑酮(1,1,3-三甲基-2-降冰片烯)等酮系溶剂。
在溶剂中使用催化剂将水解性有机硅烷进行水解缩合,所得的水解缩合物(聚合物)可以通过减压蒸馏等将作为副生成物的醇、所使用的水解催化剂、水同时除去。另外,水解中使用的酸、碱催化剂可以通过中和、离子交换而除去。而且对于本发明的形成光刻用抗蚀剂下层膜的组合物,含有其水解缩合物的形成抗蚀剂下层膜的组合物为了稳定化可以添加酸(例如有机酸)、水、醇、或它们的组合。
作为上述有机酸,可以举出例如草酸、丙二酸、甲基丙二酸、琥珀酸、马来酸、苹果酸、酒石酸、邻苯二甲酸、柠檬酸、戊二酸、柠檬酸、乳酸、水杨酸等。其中,优选为草酸、马来酸等。加入的有机酸相对于缩合物(聚有机硅氧烷)100质量份为0.5~5.0质量份。另外,加入的水可以使用纯水、超纯水、离子交换水等,其添加量相对于形成抗蚀剂下层膜的组合物100质量份可以为1~20质量份。
另外,作为加入的醇,优选为通过涂布后的加热容易飞散的醇,可以举出例如甲醇、乙醇、丙醇、异丙醇、丁醇等。加入的醇相对于形成抗蚀剂下层膜的组合物100质量份可以为1~20质量份。
本发明中可以添加具有磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构的水解性硅烷化合物(b)。
所述水解性硅烷(b)可以以通式(b-1)表示。
上述式(b-1)中,R4表示甲氧基、乙氧基、异丙氧基、丁氧基等碳原子数1~10的烷氧基。R1表示碳原子数1~10的亚烷基,可以列举出例如亚甲基、亚乙基、亚丙基、亚丁基等。R2表示上述所示的磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构。
R3表示氢原子、碳原子数1~10的烷基、碳原子数1~10的氟烷基、碳原子数2~10的烯基、或碳原子数6~20的芳基。作为碳原子数1~10的烷基,可以列举出例如、甲基、乙基、丙基、异丙基等。碳原子数2~10的烯基,可以列举出乙烯基、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-丙烯基等。特别优选使用2-丙烯基(即,烯丙基)。作为碳原子数1~10的氟烷基,可以列举出全氟甲基、全氟乙基、全氟丙基、全氟丁基等。作为碳原子数6~20的芳基,可以列举出可以被取代了的苯基、萘基等。
水解性硅烷(b)可以例示以下的。
此外,本发明涉及含有聚硅氧烷(B)的极紫外光刻用抗蚀剂下层膜形成用组合物,所述聚硅氧烷(B)含有水解性硅烷(a)与具有磺酰胺结构、羧酰胺结构、脲结构、或异氰脲酸结构的水解性硅烷化合物(b)之间的水解缩合物。
作为水解性硅烷(a)和水解性硅烷(b)的水解缩合物(聚硅氧烷(B)),可以是重均分子量1000~1000000、或1000~100000的缩合物。它们的分子量是通过GPC分析,经聚苯乙烯换算而得的分子量。
GPC的测定条件,可以使用以下条件进行,例如GPC装置(商品名HLC-8220GPC、东ソー株式会社制)、GPC柱(商品名Shodex KF803L、KF802、KF801、昭和电工制)、柱温度是40℃、洗脱液(溶出溶剂)是四氢呋喃、流量(流速)是1.0ml/min,标准试料使用聚苯乙烯(昭和电工株式会社制)。
水解缩合物的制造方法可以如上述那样进行。
所述聚硅氧烷(B)的具体例例示以下的。
在本发明中,可以含有交联性化合物。作为这些交联剂,优选使用具有至少二个交联形成取代基的交联性化合物。可举出例如,具有羟甲基、甲氧基甲基这样的交联形成取代基的三聚氰胺系化合物、取代脲系化合物。具体而言,为甲氧基甲基化甘脲或甲氧基甲基化三聚氰胺等化合物,例如为四甲氧基甲基甘脲、四丁氧基甲基甘脲或六甲氧基甲基三聚氰胺。此外,还可举出四甲氧基甲基脲、四丁氧基甲基脲等化合物。在包含这些交联剂的情况下,在固体成分中例如为50质量%以下,为0.01~50质量%,或为10~40质量%。
本发明的形成抗蚀剂下层膜的组合物可以包含酸化合物。作为酸化合物,可举出例如,对甲苯磺酸、三氟甲磺酸和吡啶-对-甲苯磺酸盐等磺酸化合物、水杨酸、磺基水杨酸、柠檬酸、苯甲酸和羟基苯甲酸等羧酸化合物。此外,作为酸化合物,可举出例如,2,4,4,6-四溴环己二烯酮、苯偶姻甲苯磺酸酯、2-硝基苄基甲苯磺酸酯、对-三氟甲基苯磺酸-2,4-二硝基苄基酯、苯基-双(三氯甲基)-均-三嗪和N-羟基琥珀酰亚胺三氟甲烷磺酸酯等通过热或光而产生酸的产酸剂。作为酸化合物,此外,可举出二苯基碘六氟磷酸盐、二苯基碘三氟甲磺酸盐和双(4-叔丁基苯基)碘三氟甲磺酸盐等碘盐系产酸剂、和三苯基锍六氟锑酸盐、和三苯基锍三氟甲磺酸盐等锍盐系产酸剂。作为酸化合物,优选使用磺酸化合物、碘盐系产酸剂、锍盐系产酸剂。酸化合物可以仅使用一种,此外可以二种以上组合使用。酸化合物的含量在固体成分中例如为0.1~10质量%,或为0.1~5质量%。
本发明的形成抗蚀剂下层膜的组合物可以含有固化催化剂。固化催化剂在将含有由水解缩合物形成的聚有机硅氧烷的涂布膜进行加热使其固化时发挥固化催化剂的作用。
作为固化催化剂,可以使用铵盐、环状铵化合物、环状胺化合物、或锍化合物。
固化催化剂,相对于聚有机硅氧烷100质量份,是0.01~10质量份、或0.01~5质量份、或0.01~3质量份。
作为流变调节剂,可举出例如,邻苯二甲酸二甲酯、邻苯二甲酸二乙酯、邻苯二甲酸二异丁酯、邻苯二甲酸二己酯、邻苯二甲酸丁基异癸基酯等邻苯二甲酸化合物、己二酸二正丁酯、己二酸二异丁酯、己二酸二异辛酯、己二酸辛基癸基酯等己二酸化合物、马来酸二正丁酯、马来酸二乙酯、马来酸二壬酯等马来酸化合物、油酸甲酯、油酸丁酯、油酸四氢糠酯等油酸化合物、和硬脂酸正丁酯、硬脂酸甘油酯等硬脂酸化合物。在使用流变调节剂的情况下,作为其使用量,在固体成分中例如为0.001~10质量%。
作为表面活性剂,可举出例如,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芳基醚类、聚氧乙烯-聚氧丙烯嵌段共聚物类、失水山梨糖醇单月桂酸酯、失水山梨糖醇单棕榈酸酯、失水山梨糖醇单硬脂酸酯、失水山梨糖醇单油酸酯、失水山梨糖醇三油酸酯、失水山梨糖醇三硬脂酸酯等失水山梨糖醇脂肪酸酯类、聚氧乙烯失水山梨糖醇单月桂酸酯、聚氧乙烯失水山梨糖醇单棕榈酸酯、聚氧乙烯失水山梨糖醇单硬脂酸酯、聚氧乙烯失水山梨糖醇三油酸酯、聚氧乙烯失水山梨糖醇三硬脂酸酯等聚氧乙烯失水山梨糖醇脂肪酸酯类等非离子系表面活性剂、商品名エフトップ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-08、R-30(大日本インキ化学工业(株)制)、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)等氟系表面活性剂、和有机硅氧烷聚合物KP341(信越化学工业(株)制)等。这些表面活性剂可以单独使用,此外也可以2种以上组合使用。在使用表面活性剂的情况下,作为其使用量,在固体成分中例如为0.0001~5质量%。
作为本发明的抗蚀剂下层膜形成用组合物中使用的溶剂,只要为可以溶解上述固体成分的溶剂,就可以没有特别限制地使用。作为这样的溶剂,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、二甘醇单甲基醚、二甘醇单乙基醚、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、环戊酮、环己酮、2-羟基丙酸乙酯、2-羟基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羟基乙酸乙酯、2-羟基-3-甲基丁酸甲酯、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、乳酸乙酯和乳酸丁酯等。这些溶剂可以单独使用,或二种以上组合使用。此外,可以将丙二醇单丁基醚、丙二醇单丁基醚乙酸酯等高沸点溶剂混合来使用。
在半导体基板(例如,硅/二氧化硅被覆基板、氮化硅基板、玻璃基板和ITO基板等)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,进行烘烤,从而形成抗蚀剂下层膜。
作为进行烘烤的条件,从烘烤温度80℃~250℃,烘烤时间0.3~60分钟中进行适宜选择。优选为烘烤温度130℃~250℃,烘烤时间0.5~5分钟。这里,作为所形成的抗蚀剂下层膜的膜厚,例如为0.01~3.0μm,优选为例如0.01~1.0μm,或为0.01~0.5μm,或为0.01~0.05μm。
接着,在抗蚀剂下层膜上,形成EUV抗蚀剂等高能量射线抗蚀剂的层。高能量射线抗蚀剂的层的形成可以通过周知的方法,即,通过高能量射线抗蚀剂组合物溶液在下层膜上的涂布和烘烤来进行。
作为EUV抗蚀剂,可以采用例如使用了PMMA(聚甲基丙烯酸甲酯)、聚羟基苯乙烯、酚醛树脂等树脂的抗蚀剂组合物。
接下来,通过规定的掩模来进行曝光。曝光时,可以使用EUV光(13.5nm)、电子束、X射线等。曝光后,还可以根据需要进行曝光后加热(PEB:Post Exposure Bake)。曝光后加热从加热温度70℃~150℃,加热时间0.3~10分钟进行适宜选择。
接着,通过显影液进行显影。作为显影液,作为例子可举出氢氧化钾、氢氧化钠等碱金属氢氧化物的水溶液、氢氧化四甲铵、氢氧化四乙铵、胆碱等氢氧化季铵的水溶液、乙醇胺、丙胺、乙二胺等胺水溶液等碱性水溶液。此外,还可以在这些显影液中添加表面活性剂等。作为显影的条件,从温度5~50℃,时间10~300秒进行适宜选择。
此外,本发明中可以作为显影液使用有机溶剂进行抗蚀剂的显影。通过这样,能够在使用例如正型光致抗蚀剂时,将没有被曝光部分的光致抗蚀剂除去、形成光致抗蚀剂的图案。
作为显影液,举例可以列举出例如,乙酸甲酯、乙酸丁酯、乙酸乙酯、乙酸异丙酯、乙酸戊酯、乙酸异戊酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、丙二醇单甲基醚、乙二醇单乙基醚乙酸酯、乙二醇单丙基醚乙酸酯、乙二醇单丁基醚乙酸酯、乙二醇单苯基醚乙酸酯、二甘醇单甲基醚乙酸酯、二甘醇单丙基醚乙酸酯、二甘醇单乙基醚乙酸酯、二甘醇单苯基醚乙酸酯、二甘醇单丁基醚乙酸酯、二甘醇单乙基醚乙酸酯、2-甲氧基丁基乙酸酯、3-甲氧基丁基乙酸酯、4-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯、3-乙基-3-甲氧基丁基乙酸酯、丙二醇单甲基醚乙酸酯、丙二醇单乙基醚乙酸酯、丙二醇单丙基醚乙酸酯、2-乙氧基丁基乙酸酯、4-乙氧基丁基乙酸酯、4-丙氧基丁基乙酸酯、2-甲氧基戊基乙酸酯、3-甲氧基戊基乙酸酯、4-甲氧基戊基乙酸酯、2-甲基-3-甲氧基戊基乙酸酯、3-甲基-3-甲氧基戊基乙酸酯、3-甲基-4-甲氧基戊基乙酸酯、4-甲基-4-甲氧基戊基乙酸酯、丙二醇二乙酸酯、甲酸甲酯、甲酸乙酯、甲酸丁酯、甲酸丙酯、乳酸乙酯、乳酸丁酯、乳酸丙酯、碳酸乙酯、碳酸丙酯、碳酸丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸丙酯、丙酮酸丁酯、乙酰乙酸甲酯、乙酰乙酸乙酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸异丙酯、2-羟基丙酸甲酯、2-羟基丙酸乙酯、甲基-3-甲氧基丙酸酯、乙基-3-甲氧基丙酸酯、乙基-3-乙氧基丙酸酯、丙基-3-甲氧基丙酸酯等。进而、可以在这些显影液中加入表面活性剂等。作为显影的条件,可以从温度5~50℃、时间10~600秒中适宜选择。
然后,以如此形成的光致抗蚀剂的图案作为保护膜,进行抗蚀剂下层膜的除去和半导体基板的加工。抗蚀剂下层膜的除去使用四氟甲烷、全氟环丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷、一氧化碳、氩气、氧气、氮气、六氟化硫、二氟甲烷、三氟化氮和三氟化氯等气体进行。
在半导体基板上形成本发明的抗蚀剂下层膜之前,还可以形成平坦化膜、缝隙填充材层、有机下层膜。在使用具有大的高度差或洞隙的半导体基板时,优选形成平坦化膜、缝隙填充材层。
实施例
(抗蚀剂的显影液是碱性水溶液时的工艺评价)
合成例1
将四乙氧基硅烷15.21g(70mol%)、甲基三乙氧基硅烷3.72g(20mol%)、苯基三甲氧基硅烷2.07g(10mol%)、丙酮31.49g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸6.95g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯42.00g,将作为反应副生成物的乙醇、甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(1-1),使用GPC测定的重均分子以聚苯乙烯换算Mw是1100。
合成例2
将四乙氧基硅烷15.21g(70mol%)、甲基三乙氧基硅烷4.65g(25mol%)、苯基三甲氧基硅烷1.03g(5mol%)、丙酮31.33g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸6.95g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯42.00g,将作为反应副生成物的乙醇、甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(1-1),使用GPC测定的重均分子以聚苯乙烯换算Mw是1300。
合成例3
将四甲氧基硅烷11.11g(70mol%)、甲基三甲氧基硅烷3.55g(25mol%)、苯基三甲氧基硅烷1.03g(5mol%)、丙酮23.55g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸6.95g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯32.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(1-1),使用GPC测定的重均分子以聚苯乙烯换算Mw是1300。
合成例4
将四甲氧基硅烷11.11g(70mol%)、甲基三甲氧基硅烷2.84g(20mol%)、4-甲氧基苯基三甲氧基硅烷2.38g(10mol%)、丙酮24.50g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸6.95g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯32.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(1-2),使用GPC测定的重均分子以聚苯乙烯换算Mw是1200。
合成例5
将四甲氧基硅烷11.11g(70mol%)、甲基三甲氧基硅烷4.26g(30mol%)、丙酮23.06g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸6.95g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯30.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(1-9),使用GPC测定的重均分子以聚苯乙烯换算Mw是1300。
合成例6
将四乙氧基硅烷24.58g(70mol%)、三乙氧基甲基硅烷6.01g(20mol%)、N-(3-(三乙氧基甲硅烷基)丙基)丁酰胺4.91g、丙酮53.26g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸11.23g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-1),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例7
将四乙氧基硅烷23.34g(70mol%)、三乙氧基甲基硅烷5.71g(20mol%)、七氟-N-(3-(三乙氧基甲硅烷基)丙基)丁酰胺6.68g、丙酮53.60g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.67g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-2),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例8
将四乙氧基硅烷24.81g(70mol%)、三乙氧基甲基硅烷7.58g(25mol%)、N-(3-(三乙氧基甲硅烷基)丙基)苯磺酰胺3.08g、丙酮53.20g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸11.34g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-3),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例9
将四乙氧基硅烷24.21g(70mol%)、三乙氧基甲基硅烷5.92g(20mol%)、N-(3-(三乙氧基甲硅烷基)丙基)丙磺酰胺5.44g、丙酮53.36g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸11.06g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-4),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例10
将四乙氧基硅烷24.87g(70mol%)、三乙氧基甲基硅烷6.08g(20mol%)、1-丙基-3-(3-(三甲氧基甲硅烷基)丙基)脲4.51g、丙酮53.18g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸11.36g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-5),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例11
将四乙氧基硅烷23.38g(70mol%)、三乙氧基甲基硅烷5.72g(20mol%)、3-(三乙氧基甲硅烷基)丙基二烯丙基异氰脲酸酯6.63g、丙酮53.59g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.68g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-6),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例12
将四乙氧基硅烷23.95g(70mol%)、三乙氧基甲基硅烷5.86g(20mol%)、式(b-1-8)单体5.82g、丙酮53.43g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.94g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-7),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例13
将四乙氧基硅烷23.90g(70mol%)、三乙氧基甲基硅烷5.84g(20mol%)、式(b-1-9)单体5.89g、丙酮53.45g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.92g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-8),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例14
将四乙氧基硅烷24.46g(70mol%)、三乙氧基甲基硅烷5.98g(20mol%)、式(b-1-10)单体5.09g、丙酮53.29g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸11.18g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-9),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例15
将四乙氧基硅烷24.31g(70mol%)、三乙氧基甲基硅烷5.94g(20mol%)、N-(5-(三甲氧基甲硅烷基)-2-氮杂-1-氧代戊基)-己内酰胺(式(b-1-11))5.31g、丙酮53.37g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸11.11g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-10),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例16
将四乙氧基硅烷23.81g(70mol%)、三乙氧基甲基硅烷5.82g(20mol%)、(S)-N-1-苯基乙基-N-三乙氧基甲硅烷基丙基脲(式(b-1-12))6.02g、丙酮53.47g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.88g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-11),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例17
将四乙氧基硅烷23.46g(70mol%)、三乙氧基甲基硅烷2.87g(20mol%)、N-(3-(三乙氧基甲硅烷基)丙基)丁酰胺9.38g、丙酮53.57g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.72g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-1),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例18
将四乙氧基硅烷21.37g(70mol%)、三乙氧基甲基硅烷2.61g(10mol%)、3-(三乙氧基甲硅烷基)丙基二烯丙基异氰脲酸酯12.12g、丙酮54.14g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸9.76g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-6),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例19
将四乙氧基硅烷22.33g(70mol%)、三乙氧基甲基硅烷2.73g(10mol%)、式(b-1-8)单体10.86g、丙酮53.88g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.20g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-7),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例20
将四乙氧基硅烷23.24g(70mol%)、三乙氧基甲基硅烷2.84g(10mol%)、式(b-1-10)单体9.67g、丙酮53.63g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.62g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-9),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例21
将四乙氧基硅烷22.97g(70mol%)、三乙氧基甲基硅烷2.81g(10mol%)、N-(5-(三甲氧基甲硅烷基)-2-氮杂-1-氧代戊基)-己内酰胺(式(b-1-11)10.03g、丙酮53.70g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.49g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-10),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例22
将四乙氧基硅烷22.44g(70mol%)、N-(3-(三乙氧基甲硅烷基)丙基)丁酰胺13.46g、丙酮53.85g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.25g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-12),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例23
将四乙氧基硅烷19.67g(70mol%)、3-(三乙氧基甲硅烷基)丙基二烯丙基异氰脲酸酯16.73g、丙酮54.61g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸8.99g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-13),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例24
将四乙氧基硅烷20.92g(70mol%)、式(b-1-8)单体15.26g、丙酮54.26g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸9.56g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-14),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例25
将四乙氧基硅烷22.14g(70mol%)、式(b-1-10)单体13.82g、丙酮53.93g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸10.12g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-14-2),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例26
将四乙氧基硅烷21.76g(70mol%)、N-(5-(三甲氧基甲硅烷基)-2-氮杂-1-氧代戊基)-己内酰胺(式(b-1-11))14.26g、丙酮54.03g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸9.95g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-15),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例27
将四乙氧基硅烷25.59g(70mol%)、三乙氧基甲基硅烷6.26g、苯基三甲氧基硅烷3.48g、丙酮52.98g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸11.69g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(1-1),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
比较合成例1
将四乙氧基硅烷25.25g(70mol%)、三乙氧基甲基硅烷6.18g(20mol%)、[4-(甲氧基甲氧基)苯基]三甲氧基硅烷3.95g(10mol%)、丙酮53.08g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸11.54g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物使用GPC的重均分子量经聚苯乙烯换算为Mw2000。
(含Si抗蚀剂下层膜的调制)
将所述合成例1~5中得到的含硅聚合物、酸、固化催化剂、溶剂、水按照表1所示比例混合,分别配制出抗蚀剂下层膜形成用组合物。表1中的聚合物的添加比例显示的不是聚合物溶液的添加量,而是聚合物本身的添加量。
在表1中,马来酸缩写为MA,苄基三乙基氯化铵缩写为BTAC,N-(3-三乙氧基甲硅烷基丙基)-4,5-二氢咪唑缩写为IMIDTEOS,三苯基氯化锍缩写为TPSCl,马来酸单三苯基锍缩写为TPSMA,丙二醇单甲基醚乙酸酯缩写为PGMEA,丙二醇单乙基醚缩写为PGEE,丙二醇单甲基醚缩写为PGME。
此外,表1中N-(3-(三乙氧基甲硅烷基)丙基)丁酰胺缩写为AmideTEOS、七氟-N-(3-(三乙氧基甲硅烷基)丙基)丁酰胺缩写为FamideTEOS、N-(3-(三乙氧基甲硅烷基)丙基)苯磺酰胺缩写为BSA、N-(3-(三乙氧基甲硅烷基)丙基)丙磺酰胺缩写为PrSA、1-(3-(三甲氧基甲硅烷基)丙基)脲缩写为UreaTMOS、1-丙基-3-(3-(三甲氧基甲硅烷基)丙基)脲缩写为PrureaTMOS、3-(三乙氧基甲硅烷基)丙基二烯丙基异氰脲酸酯缩写为DAICATEOS。水使用超纯水。各添加量以质量份表示。
表1
表1续
将上述合成例中得到的含硅聚合物、酸、固化催化剂、以及添加剂、溶剂、水按照表1所示比例混合,使用0.1μm的氟树脂制过滤器过滤,由此分别配制出抗蚀剂下层膜形成用组合物的溶液。表1中的聚合物的添加比例不是聚合物溶液的添加量而是聚合物本身的添加量。
表1中马来酸缩写为MA、苄基三乙基氯化铵缩写为BTEAC、N-(3-三乙氧基甲硅烷基丙基)-4,5-二氢咪唑缩写为IMIDTEOS、三苯基锍硝酸盐缩写为TPSNO3、三苯基锍樟脑磺酸盐缩写为TPSCS、双苯酚砜缩写为BPS、6-(3-(三甲氧基甲硅烷基)丙基)-5H-二苯并[c,e]氮杂卓(Azepine)-5,7(6H)-二酮缩写为DPImTMOS、2-(3-(三乙氧基甲硅烷基)丙基)-1H-苯并[f]异吲哚-1,3(2H)-二酮缩写为NAImTEOS、1-(3―(三乙氧基甲硅烷基)丙基)吡咯烷-2,5-二酮缩写为SucImTEOS、N-(5-(三甲氧基甲硅烷基)-2-氮杂-1-氧代戊基)-己内酰胺缩写为CapUreaTMOS、(S)-N-1-苯基乙基-N-三乙氧基甲硅烷基丙基脲缩写为PhEtUreaTEOS、丙二醇单甲基醚乙酸酯缩写为PGMEA、丙二醇单乙基醚缩写为PGEE、丙二醇单甲基醚缩写为PGME。水使用超纯水。各添加量缩写以质量份表示。
表2
表2续
(有机下层膜(A1层))
使用圆善石油化学株式会社制的CNp-PM(成分以摩尔比计为乙烯基萘60%:羟基苯乙烯40%、重均分子量:6000)形成有机下层膜(A1层)。
下面示出使用由本发明的薄膜形成用组合物形成的薄膜作为抗蚀剂下层膜时的评价结果。
(光学常数测定)
将实施例1-14、比较例1-5中配制的本申请的抗蚀剂下层膜形成用组合物分别使用旋转涂布器涂布到硅晶片上。在电热板上240℃加热1分钟,形成本申请的抗蚀剂下层膜(膜厚0.05μm)。然后对这些抗蚀剂下层膜使用光谱椭偏仪(J.A.Woollam社制、VUV-VASEVU-302)测定波长193、248nm下的折射率(n值)和光学吸光系数(也称作k值、衰减系数)。
表3
〔通过EUV曝光进行的抗蚀剂图案的形成〕
将上述有机下层膜(A1层)形成用组合物涂布在硅晶片上,在电热板上在240℃烘烤60秒,获得膜厚90nm的有机下层膜(A1层)。在其上旋转涂布由本发明的实施例1~14、比较例1~5调制的抗蚀剂下层膜形成用组合物溶液,在240℃加热1分钟,从而形成抗蚀剂下层膜(B)层(20nm)。在该硬掩模上,将EUV用抗蚀剂溶液(甲基丙烯酸酯树脂系抗蚀剂)进行旋转涂布,进行加热,形成EUV抗蚀剂层(C)层,使用EUV曝光装置(Micro Exposure Tool,简称MET),在NA=0.30,σ=0.36/0.68,Quadropole的条件下进行曝光。曝光后,进行PEB(曝光后加热),在冷却板上冷却至室温,通过碱性水溶液(四甲基氢氧化铵的2.38质量%水溶液)进行显影和冲洗处理,形成抗蚀剂图案。通过评价26nm的线与间隙的形成可否、以及图案截面观察到的图案形状进行评价。
表4
(有机抗蚀剂下层膜(A2层)的调制)
在氮气中,向100mL四口烧瓶中加入咔唑(6.69g、0.040mol、东京化成工业(株)制)、9-芴酮(7.28g、0.040mol、东京化成工业(株)制)、对甲苯磺酸一水和物(0.76g、0.0040mol、东京化成工业(株)制),加入1,4-二烷(6.69g、关东化学(株)制),然后搅拌,升温到100℃,使其溶解,开始聚合。24小时后放置冷却到60℃,然后加入氯仿(34g、关东化学(株)制)进行稀释,在甲醇(168g、关东化学(株)制)中再沉淀。将所得的沉淀物过滤,在减压干燥机中80℃干燥24小时,从而得到目标聚合物(式(C-1),下面简写成PCzFL)9.37g。
PCzFL的1H-NMR的测定结果如下。
1H-NMR(400MHZ,DMSO-d6):δ7.03-7.55(br,12H),δ7.61-8.10(br,4H),δ11.18(br,1H)
PCzFL使用GPC以聚苯乙烯换算的重均分子量Mw是2800、多分散度Mw/Mn是1.77。
在所得的树脂20g中混合作为交联剂的四甲氧基甲基甘脲(三井サイテック(株)制、商品名パウダーリンク1174)3.0g、作为催化剂的对甲苯磺酸吡啶0.30g、作为表面活性剂的メガファックR-30(大日本インキ化学(株)制、商品名)0.06g,将它们溶解在丙二醇单甲基醚乙酸酯88g中而形成溶液。之后,使用孔径0.10μm的聚乙烯制微滤器过滤,进而、使用孔径0.05μm的聚乙烯制微滤器进行过滤,配制出可以在利用多层膜进行的光刻工艺中使用的有机下层膜(A2层)形成用组合物的溶液。
(干蚀刻速度的测定)
干蚀刻速度的测定中使用的蚀刻机和蚀刻气体如下。
ES401(日本サイエンティフィック制):CF4
RIE-10NR(サムコ制):O2
将实施例15~40、比较例6中配制的含Si抗蚀剂下层膜形成用组合物的溶液使用旋转涂布器涂布到硅晶片上。在电热板上240℃加热1分钟,分别形成含Si抗蚀剂下层膜(膜厚50nm(使用CF4气体时的蚀刻速度测定用)、50nm(使用O2气体时的蚀刻速度测定用)。此外,同样使用旋转涂布器将有机下层膜(A2层)形成用组合物涂布在硅晶片上形成涂膜(膜厚0.20μm)。使用O2气作为蚀刻气体测定干蚀刻速度,对实施例15~40、比较例6的含Si抗蚀剂下层膜的干蚀刻速度进行比较。
表5中示出了使用氟系气体(CF4气)时的蚀刻速度(蚀刻速度:nm/分钟),氧系气体(O2气)耐性显示的是(本申请的抗蚀剂下层膜)/(有机下层膜A2层)的蚀刻速度比。
表5
〔通过EUV曝光进行的抗蚀剂图案的形成〕
将上述有机下层膜(A2层)形成用组合物涂布在硅晶片上,在电热板上在240℃烘烤60秒,获得膜厚90nm的有机下层膜(A2层)。在其上旋转涂布由本发明的实施例15~40、比较例6调制的抗蚀剂下层膜形成用组合物溶液,在240℃加热1分钟,从而形成抗蚀剂下层膜(B)层(20nm)。在该硬掩模上,将EUV用抗蚀剂溶液(甲基丙烯酸酯树脂系抗蚀剂)进行旋转涂布,进行加热,形成EUV抗蚀剂层(C)层,使用EUV曝光装置,在NA=0.30,σ=0.3/0.7,Annular的条件下进行曝光。曝光后,进行PEB(曝光后加热),在冷却板上冷却至室温,通过碱性水溶液(四甲基氢氧化铵的2.38质量%水溶液)进行显影和冲洗处理,形成抗蚀剂图案。通过评价26nm的线与间隙的形成可否、以及图案截面观察到的图案形状进行评价。
表6中的“良好”表示的是从拖脚(footing)到削脚(小脚,under cut)之间的形状,并且是间隙部没有明显残渣的状态,“倒塌”表示的是抗蚀剂图案剥离倒塌之类的不理想状态,“桥接”表示的是抗蚀剂图案的上部或下部彼此接触的不理想状态。
表6
(抗蚀剂的显影液是有机溶剂时的工艺评价)
合成例28
将四甲氧基硅烷22.68g(70mol%)、甲基三甲氧基硅烷7.25g(25mol%)、三乙氧基甲硅烷基丙基二烯丙基异氰脲酸酯4.40g、丙酮51.49g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸14.18g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-6),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例29
将四甲氧基硅烷21.62g(70mol%)、甲基三甲氧基硅烷4.15g(15mol%)、三乙氧基甲硅烷基丙基二烯丙基异氰脲酸酯4.20g(5mol%)、[4-(甲氧基甲氧基)苯基]三甲氧基硅烷4.63g(10mol%)、丙酮51.89g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸13.52g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-16),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
合成例30
将四甲氧基硅烷21.12g(70mol%)、甲基三甲氧基硅烷5.40g(20mol%)、三乙氧基甲硅烷基丙基二烯丙基异氰脲酸酯8.20g、丙酮52.08g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸13.21g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物相当于式(B-6),使用GPC测定的重均分子以聚苯乙烯换算Mw是2000。
比较合成例2
将四甲氧基硅烷23.25g(70mol%)、甲基三甲氧基硅烷5.95g(20mol%)、[4-(甲氧基甲氧基)苯基]三甲氧基硅烷4.98g(10mol%)、丙酮51.27g加入到300ml烧瓶中,一边将混合溶液用磁搅拌器搅拌,一边向混合溶液中滴加0.01mol/l的盐酸14.54g。添加后,将烧瓶转移到调到85℃的油浴中,在加热回流下反应240分钟。之后,将反应溶液冷却到室温,向反应溶液中加入丙二醇单甲基醚乙酸酯68.00g,将作为反应副生成物的甲醇、丙酮、水、盐酸减压蒸馏除去、浓缩,从而得到水解缩合物(聚合物)的丙二醇单甲基醚乙酸酯溶液。加入丙二醇单乙基醚,以丙二醇单甲基醚乙酸酯/丙二醇单乙基醚20/80的溶剂比率调整到以140℃下的固体残留物计算其为20重量%。所得的聚合物使用GPC经聚苯乙烯换算的重均分子量为Mw2000。
表7
(有机抗蚀剂下层膜(A3层)的调制)
将4-羟基苯基甲基丙烯酰胺30.0g、1-金刚烷基甲基丙烯酸酯37.3g、甲基丙烯酸苄基酯14.9g、2,2’-偶氮二异丁腈4.11g、丙二醇单甲基醚345.4g溶解,然后将该溶液加热,在85℃搅拌约20小时。所得的树脂相当于下述式(C-2)。通过GPC经聚苯乙烯换算而测定的重均分子量Mw是6100。
在所得的树脂2g中加入四甲氧基甲基甘脲0.3g、作为催化剂的对甲苯磺酸吡啶0.03g、表面活性剂(DIC(株)制、品名:メガファック〔商品名〕R-30、成分是氟系表面活性剂)0.01g、丙二醇单甲基醚16.1g、丙二醇单甲基醚乙酸酯6.9g,使它们溶解而形成溶液。之后,使用孔径0.2μm的聚乙烯制微滤器过滤,配制出可以在利用多层膜进行的光刻工艺中使用的有机下层膜(A3层)形成用组合物的溶液。
(干蚀刻速度的测定)
干蚀刻速度的测定中使用的蚀刻机和蚀刻气体如下。
ES401(日本サイエンティフィック制):CF4
RIE-10NR(サムコ制):O2
将实施例41~49、比较例7中配制的含Si抗蚀剂下层膜形成用组合物的溶液使用旋转涂布器涂布到硅晶片上。在电热板上240℃加热1分钟,分别形成含Si抗蚀剂下层膜(膜厚50nm(使用CF4气时的蚀刻速度测定用)、50nm(使用O2气时的蚀刻速度测定用)。此外,同样使用旋转涂布器将有机下层膜(A3层)形成用组合物涂布在硅晶片上形成涂膜(膜厚0.20μm)。使用O2气作为蚀刻气体测定干蚀刻速度,对实施例41~49、比较例7的含Si抗蚀剂下层膜的干蚀刻速度进行比较。
表8中示出了使用氟系气体(CF4气)时的蚀刻速度(蚀刻速度:nm/分钟),氧系气体(O2气)耐性显示的是(本申请的抗蚀剂下层膜)/(有机下层膜A3层)的蚀刻速度比。
表8
〔通过EUV曝光进行的抗蚀剂图案的形成〕
将上述有机下层膜(A3层)形成用组合物涂布在硅晶片上,在电热板上在240℃烘烤60秒,获得膜厚90nm的有机下层膜(A3层)。在其上旋转涂布由本发明的实施例41~49、比较例7调制的抗蚀剂下层膜形成用组合物溶液,在240℃加热1分钟,从而形成抗蚀剂下层膜(B)层(20nm)。在该硬掩模上,将EUV用抗蚀剂溶液(FFEM社制NTD抗蚀剂)进行旋转涂布,进行加热,形成EUV抗蚀剂层(C)层,使用EUV曝光装置,在NA=0.30,σ=0.3/0.7,Annular的条件下进行曝光。曝光后,进行PEB(曝光后加热),在冷却板上冷却至室温,使用FFEM社制FN-DP001(有机溶剂/乙酸丁酯)进行显影和冲洗处理,形成抗蚀剂图案。通过评价26nm的线与间隙的形成可否、和图案截面观察到的图案形状来进行评价。
表2中的“良好”表示的是从拖脚到削脚之间的形状,并且是在间隙部没有明显残渣的状态,“倒塌”表示的是抗蚀剂图案剥离倒塌之类的不理想状态,“桥接”(bridge)表示的是抗蚀剂图案的上部或下部彼此接触的不理想状态。
表9
产业可利用性
本发明的薄膜形成组合物可以作为光致抗蚀剂等抗蚀剂下层膜形成用组合物、极紫外抗蚀剂等抗蚀剂下层膜形成用组合物、极紫外抗蚀剂上层膜形成用组合物、翻转材料形成用组合物等使用。
Claims (12)
2.如权利要求1所述的抗蚀剂下层膜形成用组合物,水解性硅烷a是选自四烷氧基硅烷、烷基三烷氧基硅烷和芳基三烷氧基硅烷中的至少1种水解性硅烷。
3.如权利要求2所述的抗蚀剂下层膜形成用组合物,所述烷基三烷氧基硅烷是甲基三烷氧基硅烷。
4.如权利要求2或3所述的抗蚀剂下层膜形成用组合物,所述芳基三烷氧基硅烷是苯基三烷氧基硅烷。
5.如权利要求1或2所述的抗蚀剂下层膜形成用组合物,所述聚硅氧烷A是以相对于四烷氧基硅烷70摩尔,烷基三烷氧基硅烷为10~35摩尔、芳基三烷氧基硅烷为2~25摩尔的比例使它们共水解、缩合而成的,
6.如权利要求1或2所述的抗蚀剂下层膜形成用组合物,还含有酸化合物。
7.如权利要求1或2所述的抗蚀剂下层膜形成用组合物,还含有水。
8.如权利要求1或2所述的抗蚀剂下层膜形成用组合物,还含有铵化合物、环状铵化合物、环状胺化合物或锍化合物。
9.一种抗蚀剂下层膜的制造方法,包含以下工序:将权利要求1~8的任一项所述的抗蚀剂下层膜形成用组合物涂布到半导体基板上并烘烤。
10.一种半导体装置的制造方法,包含以下工序:
将权利要求1~8的任一项所述的抗蚀剂下层膜形成用组合物涂布到半导体基板上、并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用组合物而形成抗蚀剂膜的工序,
使用极紫外光使所述抗蚀剂膜曝光的工序,
在使用极紫外光曝光后使抗蚀剂膜显影而得到图案化了的抗蚀剂膜的工序,
通过图案化了的抗蚀剂膜对抗蚀剂下层膜进行蚀刻的工序,以及
通过图案化了的抗蚀剂膜和抗蚀剂下层膜对半导体基板进行加工的工序。
11.一种半导体装置的制造方法,包含以下工序:
在半导体基板上形成有机下层膜的工序,
在有机下层膜上涂布权利要求1~8的任一项所述的抗蚀剂下层膜形成用组合物、并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用组合物而形成抗蚀剂膜的工序,
使用极紫外光使所述抗蚀剂膜曝光的工序,
在使用极紫外光曝光后使抗蚀剂膜显影而得到图案化了的抗蚀剂膜的工序,
通过图案化了的抗蚀剂膜对抗蚀剂下层膜进行蚀刻的工序,
通过图案化了的抗蚀剂下层膜对有机下层膜进行蚀刻的工序,以及
通过图案化了的有机下层膜对半导体基板进行加工的工序。
12.如权利要求10或11所述的制造方法,显影通过碱性水溶液或有机溶剂进行。
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CN104246614A (zh) | 2014-12-24 |
US20150079792A1 (en) | 2015-03-19 |
JP6120013B2 (ja) | 2017-04-26 |
JP6418412B2 (ja) | 2018-11-07 |
TW201716510A (zh) | 2017-05-16 |
JP2017083849A (ja) | 2017-05-18 |
US9627217B2 (en) | 2017-04-18 |
KR20150008065A (ko) | 2015-01-21 |
TWI643906B (zh) | 2018-12-11 |
WO2013161372A1 (ja) | 2013-10-31 |
CN107966879B (zh) | 2021-06-01 |
CN107966879A (zh) | 2018-04-27 |
JPWO2013161372A1 (ja) | 2015-12-24 |
KR102044968B1 (ko) | 2019-12-05 |
TW201402696A (zh) | 2014-01-16 |
TWI633156B (zh) | 2018-08-21 |
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