CN113906077A - 抗蚀剂下层膜形成用组合物 - Google Patents
抗蚀剂下层膜形成用组合物 Download PDFInfo
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- CN113906077A CN113906077A CN202080033573.8A CN202080033573A CN113906077A CN 113906077 A CN113906077 A CN 113906077A CN 202080033573 A CN202080033573 A CN 202080033573A CN 113906077 A CN113906077 A CN 113906077A
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- underlayer film
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- 239000011593 sulfur Substances 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
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- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
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- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
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- 150000003624 transition metals Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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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
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
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- 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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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C08G59/625—Hydroxyacids
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- 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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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
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- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
- H01L21/0276—Photolithographic processes using an anti-reflective coating
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Abstract
本发明提供显示高的蚀刻耐性、良好的干蚀刻速度比及光学常数,即使对所谓高低差基板也被覆性良好,埋入后的膜厚差小,可形成平坦的膜的抗蚀剂下层膜形成用组合物。此外,提供使用该抗蚀剂下层膜形成用组合物的抗蚀剂下层膜及半导体装置的制造方法。一种抗蚀剂下层膜形成用组合物,其含有下述式(A)表示的化合物的一种或二种以上、下述式(B)表示的聚合物的一种或二种以上及溶剂;(式(A)中,X表示碳原子数2~50的n价有机基,n个Y分别独立地表示具有至少1个羟基的碳原子数6~60的芳香族烃基,n表示1~4的整数);[式(B)中,R1表示氢原子或甲基,R2表示选自下述式(B‑1)~(B‑3)中的至少一种基;(式(B‑1)~(B‑3)中,*表示与邻接的氧原子的键结部位)]。
Description
技术领域
本发明涉及显示高的蚀刻耐性、良好的干蚀刻速度比及光学常数,即使对所谓高低差基板也被覆性良好,埋入后的膜厚差小,可形成平坦的膜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下层膜和半导体装置的制造方法。
背景技术
近年来,对于多层抗蚀剂工艺用的抗蚀剂下层膜材料,特别要求相对于短波长的曝光发挥抗反射膜的功能,具有适当的光学常数,并且也一并具备基板加工中的蚀刻耐性,提出了利用具有包含苯环的重复单元的聚合物(专利文献1)。
现有技术文献
[专利文献]
[专利文献1]日本特开2004-354554号公报
发明内容
[发明所要解决的课题]
由于伴随抗蚀剂图案的微细化而要求抗蚀剂层的薄膜化,已知有形成至少2层的抗蚀剂下层膜,且使用该抗蚀剂下层膜作为掩模材的光刻工艺。其于半导体基板上设置至少一层的有机膜(下层有机膜)和至少一层的无机下层膜,以形成于上层抗蚀剂膜的抗蚀剂图案为掩模来将无机下层膜图案化,并以该图案为掩模来进行下层有机膜的图案化的方法,已知可形成高长宽比的图案。作为形成前述至少2层的材料,可列举有机树脂(例如丙烯酸树脂、酚醛清漆树脂)与无机材料(硅树脂(例如有机聚硅氧烷)、无机硅化合物(例如SiON、SiO2)等)的组合。进一步地,近年来广为应用为了得到1个图案而进行2次光刻与2次蚀刻的双重图案化(double patterning)技术,在各自的步骤中使用上述多层工艺。此时,对于形成最初的图案后所要形成的有机膜,必需有使高低差平坦化的特性。
但是,对于在被加工基板上所形成的抗蚀剂图案具有高低差或疏密的所谓高低差基板,也有以抗蚀剂下层膜形成用组合物的被覆性低,埋入后的膜厚差增大,不易形成平坦的膜的问题。
本发明基于这样的课题解决而完成,其目的是提供显示高的蚀刻耐性、良好的干蚀刻速度比及光学常数,即使对所谓高低差基板也被覆性良好,埋入后的膜厚差小,可形成平坦的膜的抗蚀剂下层膜形成用组合物。此外,本发明的目的是提供使用该抗蚀剂下层膜形成用组合物的抗蚀剂下层膜,及半导体装置的制造方法。
[用以解决课题的手段]
本发明包含以下方案。
[1].一种抗蚀剂下层膜形成用组合物,含有下述式(A)表示的化合物的一种或二种以上、下述式(B)表示的聚合物的一种或二种以上、以及溶剂,
式(A)中,X表示碳原子数2~50的n价有机基,n个Y分别独立地表示具有至少1个羟基的碳原子数6~60的芳香族烃基,n表示1~4的整数;
式(B)中,R1表示氢原子或甲基,R2表示选自下述式(B-1)~(B-3)中的至少一种基;
式(B-1)~(B-3)中,*表示与邻接的氧原子的键结部位。
[2].如[1]所述的抗蚀剂下层膜形成用组合物,所述式(A)中的X包含1个以上苯环、萘环、蒽环、芘环或它们的组合。
[3].如[1]所述的抗蚀剂下层膜形成用组合物,所述式(A)中的n个Y分别独立地包含具有至少1个羟基的苯环、萘环、蒽环或芘环或它们的组合。
[4].如[1]所述的抗蚀剂下层膜形成用组合物,所述式(A)中的n为2。
[5].如[1]所述的抗蚀剂下层膜形成用组合物,其中所述溶剂的沸点为160℃以上。
[6].一种抗蚀剂下层膜,其特征在于,是由[1]~[5]中任一项所述的抗蚀剂下层膜形成用组合物形成的涂膜的烧成物。
[7].一种半导体装置的制造方法,包含:
使用[1]~[5]中任一项所述的抗蚀剂下层膜形成用组合物在半导体基板上形成抗蚀剂下层膜的步骤,
在所形成的抗蚀剂下层膜之上形成抗蚀剂膜的步骤,
通过对所形成的抗蚀剂膜照射光或电子束并显影,而形成抗蚀剂图案的步骤,
经由所形成的抗蚀剂图案来蚀刻所述抗蚀剂下层膜、进行图案化的步骤,以及
经由图案化了的抗蚀剂下层膜来加工半导体基板的步骤。
[发明效果]
本发明的抗蚀剂下层膜形成用组合物,不仅具有高蚀刻耐性、良好的干蚀刻速度比及光学常数,且所得的抗蚀剂下层膜即使对所谓高低差基板也被覆性良好,埋入后的膜厚差小,形成平坦的膜,实现了更微细的基板加工。
特别是本发明的抗蚀剂下层膜形成用组合物,对于形成至少2层的以抗蚀剂膜厚的薄膜化为目的的抗蚀剂下层膜,且使用该抗蚀剂下层膜作为蚀刻掩模的光刻工艺是有效的。
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,含有下述式(A)表示的化合物的一种或二种以上、下述式(B)表示的聚合物的一种或二种以上、以及溶剂,
式(A)中,X表示碳原子数2~50的n价有机基,n个Y分别独立地表示具有至少1个羟基的碳原子数6~60的芳香族烃基,n表示1~4的整数;
式(B)中,R1表示氢原子或甲基,R2表示选自下述式(B-1)~(B-3)中的至少一种基;
式(B-1)~(B-3)中,*表示与邻接的氧原子键结的部位。
以下依序进行说明。
[式(A)表示的化合物]
式(A)中的X为碳原子数2~50的n价有机基。n价有机基,指从含碳化合物去除n个氢后的基。n为1、2、3或4。含碳化合物包括烃化合物,烃化合物包括脂肪族烃、脂环式烃、芳香族烃。含碳化合物,其分子中也可包含碳及氢以外的原子例如氧、氮、硫、卤素、碱金属、碱土类金属、过渡金属等中的一种或二种以上的原子。有机基中所含有的碳原子数为2~50;优选为4以上、6以上、8以上、10以上、42以下、34以下、26以下或18以下。
式(A)中的n个Y,分别独立地为具有至少1个羟基的碳原子数6~60的芳香族烃基。
碳原子数6~60的芳香族烃基,指由以下化合物(a)~(e)去除1个氢原子后的基:
(a)如苯、苯酚、间苯三酚之类的单环化合物、
(b)如萘、二羟基萘之类的缩合环化合物、
(c)如呋喃、噻吩、吡啶、咔唑之类的杂环化合物、
(d)如联苯、苯基吲哚、9,9-双(4-羟基苯基)芴、α,α,α’,α’-四(4-羟基苯基)-对二甲苯之类,将(a)~(c)的芳香族环以单键而键结的化合物,或
(e)如苯基萘胺之类,以例示为-CH2-、-(CH2)n-(n=1~20)、-CH<、-CH=CH-、-C≡C-、-N=N-、-NH-、-NR-、-NHCO-、-NRCO-、-S-、-COO-、-O-、-CO-及-CH=N-的间隔基(spacer)而将(a)~(d)的芳香族环连结而成的化合物。
进一步地,上述芳香族化合物具有至少1个羟基。
如此具有至少1个羟基的芳香族化合物,优选为含酚性羟基的化合物。
作为含酚性羟基的化合物,可列举苯酚、二羟基苯、三羟基苯、羟基萘、二羟基萘、三羟基萘、三(4-羟基苯基)甲烷、三(4-羟基苯基)乙烷、1,1,2,2-四(4-羟基苯基)乙烷、多核酚等。
作为上述多核酚,可列举二羟基苯、三羟基苯、羟基萘、二羟基萘、三羟基萘、三(4-羟基苯基)甲烷、三(4-羟基苯基)乙烷、2,2’-联苯酚,或1,1,2,2-四(4-羟基苯基)乙烷等。
上述碳原子数6~60的芳香族化合物的氢原子,也可被碳原子数1~20的烷基、缩环基、杂环基、羟基、氨基、硝基、醚基、烷氧基、氰基及羧基取代。
作为上述碳原子数1~20的烷基,可列举具有也可不具有取代基的直链或具有分支的烷基,可列举例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、正己基、异己基、正庚基、正辛基、环己基、2-乙基己基、正壬基、异壬基、对叔丁基环己基、正癸基、正十二烷基壬基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基及二十烷基等。优选为碳原子数1~12的烷基、更优选为碳原子数1~8的烷基、进而更优选为碳原子数1~4的烷基。
作为被氧原子、硫原子或酰胺键中断的碳原子数1~20的烷基,例如可列举含有结构单位-CH2-O-、-CH2-S-、-CH2-NHCO-或-CH2-CONH-的烷基。-O-、-S-、-NHCO-或-CONH-在前述烷基中可具有一个单位或个二单位以上。被-O-、-S-、-NHCO-或-CONH-单位中断的碳原子数1~20的烷基的具体例子,为甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基氨基、乙基羰基氨基、丙基羰基氨基、丁基羰基氨基、甲基氨基羰基、乙基氨基羰基、丙基氨基羰基、丁基氨基羰基等,进而为甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基或十八烷基,且其各自具有甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基氨基、乙基羰基氨基、甲基氨基羰基、乙基氨基羰基等取代基。优选为甲氧基、乙氧基、甲硫基、乙硫基;更优选为甲氧基、乙氧基。
杂环基指来自杂环式化合物的取代基,具体而言可列举噻吩基、呋喃基、吡啶基、嘧啶基、吡嗪基、吡咯基、唑基、噻唑基、咪唑基、喹啉基、咔唑基、喹唑啉基、嘌呤基、吲嗪基、苯并噻吩基、苯并呋喃基、吲哚基、吖啶基、异吲哚基、苯并咪唑基、异喹啉基、喹喔啉基、噌啉(Cinnoline)基、蝶啶基、色烯基(苯并吡喃基)、异色烯基(苯并吡喃基)、呫吨基、噻唑基、吡唑基、咪唑啉基、吖嗪基,这些中特别以噻吩基、呋喃基、吡啶基、嘧啶基、吡嗪基、吡咯基、唑基、噻唑基、咪唑基、喹啉基、咔唑基、喹喔啉基、嘌呤基、吲嗪基、苯并噻吩基、苯并呋喃基、吲哚基及吖啶基为优选;最优选为噻吩基、呋喃基、吡啶基、嘧啶基、吡咯基、唑基、噻唑基、咪唑基及咔唑基。
再者,以上的芳香族烃基,也可通过单键或间隔基而连结。
作为间隔基的例子可列举-CH2-、-(CH2)n-(n=1~20)、-CH<、-CH=CH-、-C≡C-、-N=N-、-NH-、-NR-、-NHCO-、-NRCO-、-S-、-COO-、-O-、-CO-及-CH=N-的一种或二种以上的组合。这些间隔基也可连结有2个以上。
上述芳香族烃基,优选包含1个以上的苯环、萘环、蒽环、芘环或它们的组合;更优选包含2个以上的苯环、萘环、蒽环、芘环或它们的组合。
[化合物(A)的调制]
式(A)表示的化合物,可通过本领域的技术人员公知的任意方法来调制。例如取n为2时为例,可通过如下述的合成流程来调制。
上述合成流程中,可通过使1分子的二环氧丙基化合物与2分子的羧酸化合物反应,使二环氧丙基化合物的2个环氧基各自开环,连结2个羧酸化合物,而得到化合物(A)。
反应温度通常为40℃至200℃。反应时间依反应温度而选择各种,但通常为30分钟至50小时左右。
如此所得的粗生成物,也可添加阴离子交换树脂及/或阳离子交换树脂,通过常规方法进行离子交换处理。
如以上方式所得的化合物的重均分子量Mw通常为500至1,000,或600至900。
[式(B)表示的聚合物]
式(B)表示的聚合物,可通过将具有由上述式(B-1)~(B-3)中选出的至少一种基的(甲基)丙烯酸或其衍生物,以本领域技术人员所公知的任意方法聚合而调制。
式(B)表示的聚合物的重均分子量并无特殊限制,优选为1,000以上、2,000以上、5,000以上、50,000以下、20,000以下,或10,000以下。
[溶剂]
作为本发明的抗蚀剂下层膜形成用组合物的溶剂,只要可溶解上述化合物(A)、上述聚合物(B)、其他成分的溶剂,则可无特殊限制地使用。特别是本发明的抗蚀剂下层膜形成用组合物能够以均匀的溶液状态来使用,因此考虑到其涂布性能时,推荐合并使用光刻步骤中一般所使用的溶剂。
如此的溶剂例如可列举甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯、丙二醇、丙二醇单甲基醚、丙二醇单乙基醚、甲基异丁基甲醇、丙二醇单丁基醚、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、丙二醇单丁基醚乙酸酯、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、乙二醇单甲基醚、乙二醇单乙基醚、乙二醇单丙基醚、乙二醇单丁基醚、乙二醇单甲基醚乙酸酯、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、二乙二醇二甲基醚、二乙二醇二乙基醚、二乙二醇二丙基醚、二乙二醇二丁基醚丙二醇单甲基醚、丙二醇二甲基醚、丙二醇二乙基醚、丙二醇二丙基醚、丙二醇二丁基醚、乳酸乙酯、乳酸丙酯、乳酸异丙酯、乳酸丁酯、乳酸异丁酯、甲酸甲酯、甲酸乙酯、甲酸丙酯、甲酸异丙酯、甲酸丁酯、甲酸异丁酯、甲酸戊酯、甲酸异戊酯、乙酸甲酯、乙酸乙酯、乙酸戊酯、乙酸异戊酯、乙酸己酯、丙酸甲酯、丙酸乙酯、丙酸丙酯、丙酸异丙酯、丙酸丁酯、丙酸异丁酯、丁酸甲酯、丁酸乙酯、丁酸丙酯、丁酸异丙酯、丁酸丁酯、丁酸异丁酯、羟基乙酸乙酯、2-羟基-2-甲基丙酸乙酯、3-甲氧基-2-甲基丙酸甲酯、2-羟基-3-甲基丁酸甲酯、甲氧基乙酸乙酯、乙氧基乙酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸乙酯、乙酸3-甲氧基丁酯、乙酸3-甲氧基丙酯、乙酸3-甲基-3-甲氧基丁酯、丙酸3-甲基-3-甲氧基丁酯、丁酸3-甲基-3-甲氧基丁酯、乙酰乙酸甲酯、甲苯、二甲苯、甲基乙基酮、甲基丙基酮、甲基丁基酮、2-庚酮、3-庚酮、4-庚酮、环己酮、N,N-二甲基甲酰胺、N-甲基乙酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、4-甲基-2-戊醇及γ-丁内酯等。这些溶剂可单独使用,或组合二种以上来使用。
此外,也可使用WO2018/131562A1记载的下述化合物。
(式(i)中的R1、R2及R3各自表示氢原子、可被氧原子、硫原子或酰胺键中断的碳原子数1~20的烷基,彼此可相同也可不同,彼此也可键结而形成环构造)。
作为碳原子数1~20的烷基,可列举具有也可不具有取代基的直链或具有分支的烷基,例如,可列举甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、正己基、异己基、正庚基、正辛基、环己基、2-乙基己基、正壬基、异壬基、对叔丁基环己基、正癸基、正十二烷基壬基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基及二十烷基等。优选为碳原子数1~12的烷基、更优选为碳原子数1~8的烷基、进而更优选为碳原子数1~4的烷基。
作为可被氧原子、硫原子或酰胺键中断的碳原子数1~20的烷基,例如可列举含有结构单位-CH2-O-、-CH2-S-、-CH2-NHCO-或-CH2-CONH-的烷基。-O-、-S-、-NHCO-或-CONH-在前述烷基中可具有一个单位或二个单位以上。被-O-、-S-、-NHCO-或-CONH-单位中断的碳原子数1~20的烷基的具体例子,为甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基氨基、乙基羰基氨基、丙基羰基氨基、丁基羰基氨基、甲基氨基羰基、乙基氨基羰基、丙基氨基羰基、丁基氨基羰基等;进而为甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十二烷基或十八烷基,且其各自具有甲氧基、乙氧基、丙氧基、丁氧基、甲硫基、乙硫基、丙硫基、丁硫基、甲基羰基氨基、乙基羰基氨基、甲基氨基羰基、乙基氨基羰基等取代基。优选为甲氧基、乙氧基、甲硫基、乙硫基;更优选为甲氧基、乙氧基。
这些溶剂为较高沸点,所以就对抗蚀剂下层膜形成用组合物赋予高埋入性或高平坦化性的目的上也为有效。
以下显示式(i)表示的优选化合物的具体例子。
上述之中,优选为3-甲氧基-N,N-二甲基丙酰胺、N,N-二甲基异丁酰胺,及下述式表示的化合物;作为式(i)表示的化合物特优选为3-甲氧基-N,N-二甲基丙酰胺及N,N-二甲基异丁酰胺。
这些溶剂可单独使用,或组合二种以上来使用。这些溶剂当中优选沸点160℃以上的,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、环己酮、3-甲氧基-N,N-二甲基丙酰胺、N,N-二甲基异丁酰胺、二乙酸2,5-二甲基己烷-1,6-二基酯(DAH;cas,89182-68-3),及1,6-二乙酰氧基己烷(cas,6222-17-9)等。特优选为丙二醇单甲基醚、丙二醇单甲基醚乙酸酯、N,N-二甲基异丁酰胺。
[交联剂、酸及/或产酸剂]
上述式(B)表示的聚合物,仅以热就会进行交联,而且无脱离成分,因此所形成的膜不会产生收缩,具有可实现平坦的膜的优点。但是,掺合上述式(B)表示的聚合物以外的交联剂时,因为交联的过程中的官能基脱离,或交联所需的加热等,有引起膜收缩,结果对所得的膜的平坦性造成不良影响的风险。因而,本发明的抗蚀剂下层膜形成用组合物,在上述式(B)表示的聚合物以外,不含有交联剂。此处所称的“交联剂”,一般包含具有至少2个交联形成取代基的低分子化合物或聚合物。
作为本发明的抗蚀剂下层膜形成用组合物中所不含有的交联剂,可列举三聚氰胺、取代脲,或它们的聚合物等。更具体而言,为具有至少2个交联形成取代基的交联剂,其是甲氧基甲基化乙炔脲、丁氧基甲基化乙炔脲、甲氧基甲基化三聚氰胺、丁氧基甲基化三聚氰胺、甲氧基甲基化苯并胍胺、丁氧基甲基化苯并胍胺、甲氧基甲基化脲、丁氧基甲基化脲,或甲氧基甲基化硫脲等的化合物。此外,也不含这些化合物的缩合体。
此外,本发明的抗蚀剂下层膜形成用组合物所不含有的交联剂,可列举分子内含有具有芳香族环(例如苯环、萘环)的交联形成取代基的耐热性高的交联剂。
作为如此的本发明的抗蚀剂下层膜形成用组合物所不含有的交联剂,可列举具有下述式(4)的部分构造的化合物,或具有下述式(5)的重复单位的聚合物或寡聚物。
上述R11、R12、R13及R14为氢原子或碳数1至10的烷基。
式(4)及式(5)的化合物、聚合物、寡聚物如以下所例示。
因此,本发明的抗蚀剂下层膜形成用组合物,也不含有与上述“交联剂”一同惯用的“酸”及“产酸剂”。
本发明的抗蚀剂下层膜形成用组合物中所不含有的酸,例如可列举对甲苯磺酸、三氟甲磺酸、吡啶对甲苯磺酸、水杨酸、5-磺基水杨酸、4-苯酚磺酸、樟脑磺酸、4-氯苯磺酸、苯二磺酸、1-萘磺酸、柠檬酸、苯甲酸、羟基苯甲酸、萘甲酸等。
作为本发明的抗蚀剂下层膜形成用组合物中所不含有的产酸剂,可列举热产酸剂或光产酸剂。
本发明的抗蚀剂下层膜形成用组合物中所不含有的热产酸剂,可列举2,4,4,6-四溴环己二烯酮、苯偶姻甲苯磺酸酯、甲苯磺酸2-硝基苄酯、其他有机磺酸烷基酯等。
作为本发明的抗蚀剂下层膜形成用组合物中所不含有的盐化合物,可列举二苯基碘六氟磷酸盐、二苯基碘三氟甲磺酸盐、二苯基碘九氟正丁磺酸盐、二苯基碘全氟正辛磺酸盐、二苯基碘樟脑磺酸盐、双(4-叔丁基苯基)碘樟脑磺酸盐及双(4-叔丁基苯基)碘三氟甲磺酸盐等的碘盐化合物,及三苯基锍六氟锑酸盐、三苯基锍九氟正丁磺酸盐、三苯基锍樟脑磺酸盐及三苯基锍三氟甲磺酸盐等的锍盐化合物等。
作为本发明的抗蚀剂下层膜形成用组合物中所不含有的磺酰亚胺化合物,例如可列举N-(三氟甲烷磺酰氧基)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)琥珀酰亚胺及N-(三氟甲烷磺酰氧基)萘二甲酰亚胺等。
本发明的抗蚀剂下层膜形成用组合物中所不含有的二磺酰基重氮甲烷化合物,例如可列举双(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。
[其他成分]
本发明的抗蚀剂下层膜形成用组合物中,为了不产生针孔或条纹等,进一步提高对表面不均的涂布性,可掺合表面活性剂。表面活性剂例如可列举聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯鲸蜡基醚、聚氧乙烯油基醚等的聚氧乙烯烷基醚类;聚氧乙烯辛基苯酚醚、聚氧乙烯壬基苯酚醚等的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的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的聚氧乙烯失水山梨糖醇脂肪酸酯类等的非离子表面活性剂;Eftop EF301、EF303、EF352(Tokem Products株式会社制、商品名);Megafac F171、F173、R-40、R-40N、R-40LM(DIC株式会社制、商品名);Fluorad FC430、FC431(住友3M株式会社制、商品名);Asahiguard AG710;Surflon S-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子株式会社制、商品名)等的氟表面活性剂;有机硅氧烷聚合物KP341(信越化学工业株式会社制)等。这些表面活性剂的掺合量,相对于抗蚀剂下层膜材料的全部固体成分而言通常为2.0质量%以下、优选为1.0质量%以下。这些表面活性剂可单独使用、也可组合二种以上来使用。使用表面活性剂时,作为其比例,相对于抗蚀剂下层膜形成用组合物的固体成分100质量份而言,为0.0001至5质量份,或0.001至1质量份,或0.01至0.5质量份。
本发明的抗蚀剂下层膜形成用组合物中,可添加吸光剂、流变性调整剂、粘合辅助剂等。流变性调整剂对于提高下层膜形成用组合物的流动性有效。粘合辅助剂对于提高半导体基板或抗蚀剂与下层膜的密合性有效。
吸光剂例如可适合使用“工业用色素的技术与市场(工業用色素の技術と市場)”(CMC出版)或“染料便览”(有机合成化学协会编)中记载的市售的吸光剂,例如C.I.分散黄1、3、4、5、7、8、13、23、31、49、50、51、54、60、64、66、68、79、82、88、90、93、102、114及124;C.I.分散橙1、5、13、25、29、30、31、44、57、72及73;C.I.分散红1、5、7、13、17、19、43、50、54、58、65、72、73、88、117、137、143、199及210;C.I.分散紫43;C.I.分散蓝96;C.I.荧光增白剂112、135及163;C.I.溶剂橙2及45;C.I.溶剂红1、3、8、23、24、25、27及49;C.I.颜料绿10;C.I.颜料褐2等。上述吸光剂通常相对于抗蚀剂下层膜形成用组合物的全部固体成分而言以10质量%以下、优选为5质量%以下的比例掺合。
流变性调整剂,主要以提高抗蚀剂下层膜形成用组合物的流动性,特别是于烘烤步骤中,提高抗蚀剂下层膜的膜厚均匀性或提高抗蚀剂下层膜形成用组合物对孔洞内部的填充性为目的来添加。具体例子可列举邻苯二甲酸二甲酯、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、邻苯二甲酸丁酯异癸酯等的邻苯二甲酸衍生物;己二酸二正丁酯、己二酸二异丁酯、己二酸二异辛酯、己二酸辛酯癸酯等的己二酸衍生物;马来酸二正丁酯、马来酸二乙酯、马来酸二壬酯等的马来酸衍生物;油酸甲酯、油酸丁酯、油酸四氢呋喃甲酯等的油酸衍生物,或硬脂酸正丁酯、硬脂酸甘油酯等的硬脂酸衍生物。这些流变性调整剂,相对于抗蚀剂下层膜形成用组合物的全部固体成分而言,通常以低于30质量%的比例掺合。
粘合辅助剂,主要以提高基板或抗蚀剂与抗蚀剂下层膜形成用组合物的密合性,特别是于显影中使抗蚀剂不会剥离为目的而添加。具体例子可列举三甲基氯硅烷、二甲基羟甲基氯硅烷、甲基二苯基氯硅烷、氯甲基二甲基氯硅烷等的氯硅烷类;三甲基甲氧基硅烷、二甲基二乙氧基硅烷、甲基二甲氧基硅烷、二甲基羟甲基乙氧基硅烷、二苯基二甲氧基硅烷、苯基三乙氧基硅烷等的烷氧基硅烷类;六甲基二硅氮烷、N,N’-双(三甲基硅烷基)脲、二甲基三甲基硅烷基胺、三甲基硅烷基咪唑等的硅氮烷类;羟甲基三氯硅烷、γ-氯丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三甲氧基硅烷等的硅烷类;苯并三唑、苯并咪唑、吲唑、咪唑、2-巯基苯并咪唑、2-巯基苯并噻唑、2-巯基苯并唑、脲唑、硫脲嘧啶、巯基咪唑、巯基嘧啶等的杂环式化合物,或1,1-二甲基脲、1,3-二甲基脲等的脲,或硫脲化合物。这些粘合辅助剂,相对于抗蚀剂下层膜形成用组合物的全部固体成分而言,通常以低于5质量%、优选以低于2质量%的比例掺合。
本发明的抗蚀剂下层膜形成用组合物的固体成分通常为0.1至70质量%、优选为0.1至60质量%。固体成分为由抗蚀剂下层膜形成用组合物中去除溶剂后的全部成分的含有比例。固体成分中之上述化合物(A)与上述聚合物(B)的合计比例(含有2种以上的上述化合物(A)、上述聚合物(B)时为它们的合计)依序优选为1至100质量%、1至99.9质量%、50至99.9质量%、50至95质量%、50至90质量%。
评估抗蚀剂下层膜形成用组合物是否为均匀的溶液状态的尺度之一,为观察特定微滤器的通过性,本发明的抗蚀剂下层膜形成用组合物,会通过孔径0.1μm的微滤器,呈现均匀的溶液状态。
上述微滤器材质,可列举PTFE(聚四氟乙烯)、PFA(四氟乙烯/全氟烷基乙烯基醚共聚物)等的氟树脂、PE(聚乙烯)、UPE(超高分子量聚乙烯)、PP(聚丙烯)、PSF(聚砜)、PES(聚醚砜)、尼龙,优选为PTFE(聚四氟乙烯)制。
[抗蚀剂下层膜及半导体装置的制造方法]
以下,说明使用本发明的抗蚀剂下层膜形成用组合物的抗蚀剂下层膜及半导体装置的制造方法。
在半导体装置的制造所使用的基板(例如硅晶圆基板、硅/二氧化硅被覆基板、氮化硅基板、玻璃基板、ITO基板、聚酰亚氨基板,及低介电常数材料(low-k材料)被覆基板等)上通过旋转器、涂布器等的适当涂布方法涂布本发明的抗蚀剂下层膜形成用组合物后,通过烧成而形成抗蚀剂下层膜。烧成的条件,由烧成温度80℃至250℃、烧成时间0.3至60分钟中适当选择。优选为烧成温度150℃至250℃、烧成时间0.5至2分钟。此处,所形成的下层膜的膜厚,例如为10至1000nm,或20至500nm,或30至400nm,或50至300nm。
此外,也可在本发明的有机抗蚀剂下层膜上形成无机抗蚀剂下层膜(硬掩模)。例如可为由旋转涂布形成如WO2009/104552A1记载的含硅抗蚀剂下层膜(无机抗蚀剂下层膜)形成用组合物的方法,此外可由CVD法等形成Si的无机材料膜。
此外,可通过将本发明的抗蚀剂下层膜形成用组合物涂布于具备具有高低差的部分与不具有高低差的部分的半导体基板(所谓的高低差基板)上并烧成,而形成该具有高低差的部分与不具有高低差的部分的高低差为3~50nm的范围内的抗蚀剂下层膜。
接着于该抗蚀剂下层膜上形成抗蚀剂膜,例如光致抗蚀剂的层。光致抗蚀剂的层的形成,可通过众所周知的方法,也即对下层膜上涂布光致抗蚀剂组合物溶液并烧成来进行。光致抗蚀剂的膜厚例如为50至10000nm,或100至2000nm,或200至1000nm。
抗蚀剂下层膜之上所形成的光致抗蚀剂,只要对曝光所使用的光会感光、就无特殊限定。负型光致抗蚀剂及正型光致抗蚀剂均可使用。有包含酚醛清漆树脂与1,2-萘醌重氮磺酸酯的正型光致抗蚀剂;包含具有通过酸而分解而使碱溶解速度上升的基的粘合剂与光产酸剂的化学增强型光致抗蚀剂;包含通过酸而分解而使光致抗蚀剂的碱溶解速度上升的低分子化合物、碱可溶性粘合剂与光产酸剂的化学增强型光致抗蚀剂,及包含具有通过酸而分解而使碱溶解速度上升的基的粘合剂、通过酸而分解而使光致抗蚀剂的碱溶解速度上升的低分子化合物与光产酸剂的化学增强型光致抗蚀剂等。例如可列举Shipley公司制商品名APEX-E、住友化学工业株式会社制商品名PAR710,及信越化学工业株式会社制商品名SEPR430等。此外,例如可列举如Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)或Proc.SPIE,Vol.3999,365-374(2000)所记载的含氟原子聚合物光致抗蚀剂。
接着,通过光或电子束的照射与显影而形成抗蚀剂图案。首先,通过特定的掩模进行曝光。曝光可使用近紫外线、远紫外线,或极紫外线(例如EUV(波长13.5nm))等。具体而言,可使用KrF准分子激光(波长248nm)、ArF准分子激光(波长193nm)及F2准分子激光(波长157nm)等。这些中特别以ArF准分子激光(波长193nm)及EUV(波长13.5nm)为优选。曝光后,也可依需要进行曝光后加热(post exposure bake)。曝光后加热以从加热温度70℃至150℃、加热时间0.3至10分钟中所适当选择的条件来进行。
此外,本发明中,作为抗蚀剂,可使用电子束光刻用抗蚀剂以取代光致抗蚀剂。作为电子束抗蚀剂,负型、正型均可使用。有包含产酸剂与具有通过酸而分解而使碱溶解速度变化的基的粘合剂的化学增强型抗蚀剂;包含碱可溶性粘合剂、产酸剂与通过酸而分解而使抗蚀剂的碱溶解速度变化的低分子化合物的化学增强型抗蚀剂;包含产酸剂、具有通过酸而分解而使碱溶解速度变化的基的粘合剂与通过酸而分解而使抗蚀剂的碱溶解速度变化的低分子化合物的化学增强型抗蚀剂;包含具有通过电子束而分解而使碱溶解速度变化的基的粘合剂的非化学增强型抗蚀剂;包含具有通过电子束而被切断而使碱溶解速度变化的部位的粘合剂的非化学增强型抗蚀剂等。使用这些电子束抗蚀剂时使照射源为电子束,也与使用光致抗蚀剂时同样地可形成抗蚀剂图案。
接着,通过显影液而进行显影。通过这样,例如使用正型光致抗蚀剂的情况时,经曝光部分的光致抗蚀剂被去除,而形成光致抗蚀剂的图案。
显影液可列举例如氢氧化钾、氢氧化钠等的碱金属氢氧化物的水溶液;氢氧化四甲基铵、氢氧化四乙基铵、胆碱等的氢氧化季铵的水溶液;乙醇胺、丙胺、乙二胺等的胺水溶液等的碱性水溶液。进一步地,这些显影液中也可添加表面活性剂等。显影的条件,由温度5至50℃、时间10至600秒中适当选择。
然后,以如此所形成的光致抗蚀剂(上层)的图案为保护膜,进行去除无机下层膜(中间层),接着以包含图案化了的光致抗蚀剂及无机下层膜(中间层)的膜为保护膜,进行去除有机下层膜(下层)。最后,以图案化了的无机下层膜(中间层)及有机下层膜(下层)为保护膜,进行半导体基板的加工。
首先,通过干蚀刻去除已经将光致抗蚀剂去除了的部分的无机下层膜(中间层),使半导体基板露出。无机下层膜的干蚀刻可使用四氟甲烷(CF4)、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、三氟化氮及三氟化氯、氯气、三氯硼烷及二氯硼烷等的气体。无机下层膜的干蚀刻优选使用卤素类气体,更优选以氟类气体进行。氟类气体例如可列举四氟甲烷(CF4)、全氟环丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷,及二氟甲烷(CH2F2)等。
然后,以包含图案化了的光致抗蚀剂及无机下层膜的膜为保护膜,进行去除有机下层膜。有机下层膜(下层)优选以氧气类气体进行干蚀刻。这是由于含大量硅原子的无机下层膜,不易被氧气类气体的干蚀刻去除的原因。
最后,进行半导体基板的加工。半导体基板的加工优选通过以氟气类气体的干蚀刻来进行。
氟气类气体例如可列举四氟甲烷(CF4)、全氟环丁烷(C4F8)、全氟丙烷(C3F8)、三氟甲烷,及二氟甲烷(CH2F2)等。
此外,在抗蚀剂下层膜之上层,在光致抗蚀剂形成前可形成有机的抗反射膜。这里所使用的抗反射膜组合物并无特殊限制,可由至今为止在光刻工艺中所惯用的当中任意选择来使用,此外,可通过惯用的方法例如以旋转器、涂布器的涂布及烧成来进行抗反射膜形成。
本发明中,在基板上使有机下层膜成膜之后,可于其上使无机下层膜成膜,进而于其上被覆光致抗蚀剂。由此光致抗蚀剂的图案宽度变窄,即使为了防止图案倒塌而薄薄地被覆光致抗蚀剂时,也能够通过选择适当的蚀刻气体进行基板加工。例如,能够以对光致抗蚀剂为充分快的蚀刻速度的氟气类气体为蚀刻气体对抗蚀剂下层膜加工,且能够以对无机下层膜为充分快的蚀刻速度的氟气类气体为蚀刻气体来进行基板的加工,进而能够以对有机下层膜为充分快的蚀刻速度的氧气类气体为蚀刻气体,来进行基板的加工。
此外,由抗蚀剂下层膜形成用组合物所形成的抗蚀剂下层膜,依光刻工艺中所使用的光的波长不同,可能有具有对该光的吸收的情况。而如此情况下,可作为具有防止来自基板的反射光的效果的抗反射膜而发挥功能。进一步地,本发明的抗蚀剂下层膜形成用组合物所形成的下层膜也可作为硬掩模而发挥功能。本发明的下层膜,也可使用为如下的层:用以防止基板与光致抗蚀剂的相互作用的层、具有防止光致抗蚀剂所用的材料或对光致抗蚀剂曝光时所生成的物质对基板的不良作用的功能的层、具有防止加热烧成时由基板所生成的物质对上层光致抗蚀剂的扩散的功能的层,及用以减少半导体基板介电体层所造成的光致抗蚀剂层的毒化(poisoning)效果的阻挡层等。
此外,由抗蚀剂下层膜形成用组合物所形成的下层膜,可应用于双重镶嵌(dualdamascene)工艺所用的形成有通孔(via hole)的基板,作为可将孔洞无间隙地填充的埋入材来使用。此外,也可作为用以将具有凹凸的半导体基板的表面平坦化的平坦化材来使用。
[实施例]
以下,使用下述实施例说明本发明的抗蚀剂下层膜形成用组合物的具体例子,但并非用此来限定本发明。
示出用于测定下述合成例所得反应生成物的重均分子量的装置等。
装置:东曹株式会社制HLC-8320GPC
GPC管柱:TSKgel Super-MultiporeHZ-N(2支)
管柱温度:40℃
流量:0.35ml/分钟
洗脱液:THF
标准试样:聚苯乙烯(昭和电工株式会社)
使用于下述合成例的试药的化学结构如下示那样。
<合成例1>
向丙二醇单甲基醚(以下,本说明书中简称为PGME)149.42g中添加商品名HP-4032D(DIC株式会社制)25.00g、3,7-二羟基-2-萘甲酸(Midori化学株式会社制)37.34g,及作为催化剂的乙基三苯基溴化1.70g后,在140℃反应24小时,得到含反应生成物的溶液。添加阴离子交换树脂(制品名:Dowex[注册商标]MONOSPHERE[注册商标]550A、Muromachi Technos株式会社)64.00g与阳离子交换树脂(制品名:Amberlyst[注册商标]15JWET、有机株式会社)64.00g,在25℃至30℃搅拌4小时后过滤。
进行所得反应生成物的GPC分析后,以标准聚苯乙烯换算,重均分子量为680。推定所得到的反应生成物为具有下述式(1)表示的结构单位的化合物。
<合成例2>
向PGME154.07g中添加商品名YX8800(三菱化学株式会社制)30.00g、3,7-二羟基-2-萘甲酸(Midori化学株式会社制)34.46g,及作为催化剂的乙基三苯基溴化1.57g后,在140℃反应24小时,得到含反应生成物的溶液。添加阴离子交换树脂(制品名:Dowex[注册商标]MONOSPHERE[注册商标]550A、Muromachi Technos株式会社)66.00g与阳离子交换树脂(制品名:Amberlyst[注册商标]15JWET、有机株式会社)66.00g,在25℃至30℃搅拌4小时后过滤。
进行所得反应生成物的GPC分析后,以标准聚苯乙烯换算,重均分子量为690。推定所得到的反应生成物,为具有下述式(2)表示的结构单位的化合物。
<合成例3>
向PGME35.18g中添加商品名YX4000(三菱化学株式会社制)7.00g、3,7-二羟基-2-萘甲酸(Midori化学株式会社制)7.73g,及作为催化剂的乙基三苯基溴化0.35g后,在140℃反应24小时,得到含反应生成物的溶液。添加阴离子交换树脂(制品名:Dowex[注册商标]MONOSPHERE[注册商标]550A、Muromachi Technos株式会社)15.00g与阳离子交换树脂(制品名:Amberlyst[注册商标]15JWET、有机株式会社)15.00g,在25℃至30℃搅拌4小时后过滤。
进行所得反应生成物的GPC分析后,以标准聚苯乙烯换算,重均分子量为820。推定所得到的反应生成物为具有下述式(3)表示的结构单位的化合物。
<合成例4>
向PGME34.22g中添加商品名HP-4032D(DIC株式会社制)6.00g、6-羟基-2-萘甲酸(东京化成工业株式会社制)8.27g,及作为催化剂的乙基三苯基溴化0.41g后,在140℃反应24小时,得到含反应生成物的溶液。添加阴离子交换树脂(制品名:Dowex[注册商标]MONOSPHERE[注册商标]550A、Muromachi Technos株式会社)14.70g与阳离子交换树脂(制品名:Amberlyst[注册商标]15JWET、有机株式会社)14.70g,在25℃至30℃搅拌4小时后过滤。
进行所得反应生成物的GPC分析后,以标准聚苯乙烯换算,重均分子量为720。推定所得到的反应生成物为具有下述式(4)表示的结构单位的化合物。
<合成例5>
向PGME34.22g中添加商品名HP-4032D(DIC株式会社制)6.00g、6-羟基-1-萘甲酸(东京化成工业株式会社制)8.27g,及作为催化剂的乙基三苯基溴化0.41g后,在140℃反应24小时,得到含反应生成物的溶液。添加阴离子交换树脂(制品名:Dowex[注册商标]MONOSPHERE[注册商标]550A、Muromachi Technos株式会社)14.70g与阳离子交换树脂(制品名:Amberlyst[注册商标]15JWET、有机株式会社)14.70g,在25℃至30℃搅拌4小时后过滤。
进行所得反应生成物的GPC分析后,以标准聚苯乙烯换算,重均分子量为680。推定所得到的反应生成物为具有下述式(5)表示的结构单位的化合物。
<交联剂合成例1>
将甲基丙烯酸环氧丙酯(东京化成工业株式会社)20.00g、2,2’-偶氮双异丁酸二甲酯(富士胶卷和光纯药株式会社)1.00g溶解于丙二醇单甲基醚乙酸酯(以下,本说明书中简称为PGMEA)21.00g后,添加到加热并保持于100℃的PGMEA28.00g中,反应24小时,得到含反应生成物的溶液。使用甲醇(630g、关东化学株式会社制)进行再沉淀。将所得的沉淀物过滤,以减压干燥机60℃干燥24小时,得到目标的聚合物。
进行反应生成物的GPC分析后,以标准聚苯乙烯换算,重均分子量为8,100。推定所得到的反应生成物为具有下述式(6)表示的结构单位的聚合物。
[抗蚀剂下层膜形成用组合物的调制]
<实施例1>
在含有前述合成例1所得到的化合物1.66g的溶液(溶剂为合成时所使用的PGME、固体成分为25.94质量%)6.38g中,混合含有前述交联剂合成例1所得到的聚合物0.74g的溶液(溶剂为PGMEA、固体成分为32.20质量%)2.31g、PGME3.56g、PGMEA17.70g,及表面活性剂(DIC株式会社制、商品名:R-40)1质量%PGMEA溶液0.050g,成为8.0质量%溶液。将该溶液使用孔径0.2μm的聚四氟乙烯制微滤器过滤,调制抗蚀剂下层膜形成用组合物。
<实施例2>
在含有前述合成例2所得到的化合物1.16g的溶液(溶剂为合成时所使用的PGME、固体成分为26.05质量%)4.45g中,混合含有前述交联剂合成例1所得到的聚合物0.52g的溶液(溶剂为PGMEA、固体成分为32.20质量%)1.62g、PGME2.21g、PGMEA12.44g,及表面活性剂(DIC株式会社制、商品名:R-40)1质量%PGMEA溶液0.035g,成为8.4质量%溶液。将该溶液使用孔径0.2μm的聚四氟乙烯制微滤器过滤,调制抗蚀剂下层膜形成用组合物。
<实施例3>
在含有前述合成例3所得到的化合物1.45g的溶液(溶剂为合成时所使用的PGME、固体成分为25.92质量%)5.59g中,混合含有前述交联剂合成例1所得到的聚合物0.65g的溶液(溶剂为PGMEA、固体成分为32.20质量%)2.02g、PGME2.73g、PGMEA14.62g,及表面活性剂(DIC株式会社制、商品名:R-40)1质量%PGMEA溶液0.043g,成为8.4质量%溶液。将该溶液使用孔径0.2μm的聚四氟乙烯制微滤器过滤,调制抗蚀剂下层膜形成用组合物。
<实施例4>
在含有前述合成例4所得到的化合物1.45g的溶液(溶剂为合成时所使用的PGME、固体成分为24.35质量%)5.95g中,混合含有前述交联剂合成例1所得到的聚合物0.65g的溶液(溶剂为PGMEA、固体成分为32.20质量%)2.02g、PGME2.37g、PGMEA14.62g,及表面活性剂(DIC株式会社制、商品名:R-40)1质量%PGMEA溶液0.043g,成为8.4质量%溶液。将该溶液使用孔径0.2μm的聚四氟乙烯制微滤器过滤,调制抗蚀剂下层膜形成用组合物。
<实施例5>
在含有前述合成例5所得到的化合物1.45g的溶液(溶剂为合成时所使用的PGME、固体成分为24.67质量%)5.87g中,混合含有前述交联剂合成例1所得到的聚合物0.65g的溶液(溶剂为PGMEA、固体成分为32.20质量%)2.02g、PGME2.45g、PGMEA14.62g,及表面活性剂(DIC株式会社制、商品名:R-40)1质量%PGMEA溶液0.043g,成为8.4质量%溶液。将该溶液使用孔径0.2μm的聚四氟乙烯制微滤器过滤,调制抗蚀剂下层膜形成用组合物。
<比较例1>
向商品名TEP-TPA(旭有机材株式会社制、下述式(7))0.87g中混合含有前述交联剂合成例1所得到的聚合物0.39g的溶液(溶剂为PGMEA、固体成分为32.20质量%)1.21g、PGME4.12g、PGMEA8.77g,及表面活性剂(DIC株式会社制、商品名:R-40)1质量%PGMEA溶液0.026g,成为8.4质量%溶液。将该溶液使用孔径0.2μm的聚四氟乙烯制微滤器过滤,调制抗蚀剂下层膜形成用组合物。
<比较例2>
向商品名TEP-DF(旭有机材株式会社制、下述式(8))0.87g中混合含有前述交联剂合成例1所得到的聚合物0.39g的溶液(溶剂为PGMEA、固体成分为32.20质量%)1.21g、PGME4.12g、PGMEA8.77g,及表面活性剂(DIC株式会社制、商品名:R-40)1质量%PGMEA溶液0.026g,成为8.4质量%溶液。将该溶液使用孔径0.2μm的聚四氟乙烯制微滤器过滤,调制抗蚀剂下层膜形成用组合物。
<比较例3>
在含有商品名GNC-8(群荣化学工业株式会社制、下述式(9))0.87g的溶液(溶剂为PGMEA、固体成分为29.10质量%)2.99g中混合含有前述交联剂合成例1所得到的聚合物0.39g的溶液(溶剂为PGMEA、固体成分为32.20质量%)1.21g、PGME4.12g、PGMEA6.65g,及表面活性剂(DIC株式会社制、商品名:R-40)1质量%PGMEA溶液0.026g,成为8.4质量%溶液。将该溶液使用孔径0.2μm的聚四氟乙烯制微滤器过滤,调制抗蚀剂下层膜形成用组合物。
[溶解性试验]
确认实施例1至实施例5及比较例1至比较例3所调制的抗蚀剂下层膜形成用组合物中有无不溶物。无不溶物时,其结果在下述表1中以“○”表示。比较例2在调制后的时间点确认到有不溶物,因此未实施之后的评估。
[向光致抗蚀剂溶剂中溶出的试验]
将实施例1至实施例5、比较例1及比较例3所调制的抗蚀剂下层膜形成用组合物分别通过旋转器涂布于硅晶片上。然后,在加热板上以下述表1所示的温度烘烤1分钟,形成抗蚀剂下层膜(膜厚0.2μm)。将这些抗蚀剂下层膜浸渍于光致抗蚀剂溶液所使用的溶剂PGME/PGMEA混合溶剂(PGME/PGMEA的质量基准的混合比率为70/30)中,确认不溶于溶剂,其结果于下述表1中以“○”表示。
[光学参数的试验]
将实施例1至实施例5、比较例1及比较例3所调制的抗蚀剂下层膜形成用组合物通过旋转器涂布于硅晶片上。然后,在加热板上以下述表1所示的温度烘烤1分钟,形成抗蚀剂下层膜(膜厚0.2μm)。然后,将这些抗蚀剂下层膜使用光谱椭偏仪(J.A.Woollam公司制、VUV-VASE VU-302),测定于波长193nm的折射率(n值)及衰减系数(k值)。其结果示于下述表1。为了使上述抗蚀剂下层膜具有充分的抗反射功能,在波长193nm的k值较期望为0.1以上、0.5以下。
表1
[对高低差基板被覆的试验]
作为平坦化性的评估,对100nm膜厚的SiO2基板进行沟槽(trench)宽10nm、节距(pitch)100nm的密集区域(DENSE)与沟槽宽100nm、节距10μm的稀疏沟槽图案区域(ISO,ァイソ卜レンチパタ一ン工リァ)的被覆膜厚的比较。将实施例1至实施例5、比较例1及比较例3的抗蚀剂下层膜形成用组合物涂布于上述基板上为240nm的膜厚后,在加热板上以上述表1所示的温度烘烤1分钟,形成抗蚀剂下层膜(膜厚0.24μm)。使用日立高科技株式会社制扫描型电子显微镜(S-4800)观察该基板的高低差被覆性,通过测定高低差基板的密集区域(图案部)与稀疏沟槽图案区域的膜厚差(密集区域与稀疏沟槽图案区域的涂布高低差,称为Bias),而评估平坦化性。在各区域的膜厚与涂布高低差的值示于表2。平坦化性评估,Bias的值越小,平坦化性越高。再者,上述表1中,将涂布高低差低于50nm的表示为“○”、50nm以上的表示为“×”。
表2
Trench | Iso | Trench/Iso | |
膜厚(nm) | 膜厚(nm) | 涂布高低差(nm) | |
实施例1 | 238 | 214 | 24 |
实施例2 | 240 | 206 | 34 |
实施例3 | 240 | 198 | 42 |
实施例4 | 236 | 210 | 26 |
实施例5 | 240 | 200 | 40 |
比较例1 | 244 | 194 | 50 |
比较例2 | - | - | - |
比较例3 | 238 | 181 | 57 |
比较平坦化性时,实施例1至实施例5的结果是,密集区域与稀疏沟槽图案区域的涂布高低差较比较例1及比较例3的结果更小,所以可以说由实施例1至实施例5的抗蚀剂下层膜形成用组合物所得到的抗蚀剂下层膜其平坦化性良好。
[产业上的可利用性]
本发明的抗蚀剂下层膜形成用组合物在涂布于基板后,通过烧成步骤展现高的回流性,即使在具有高低差的基板上也可平坦地涂布,可形成平坦的膜。此外,由于具有适当的抗反射效果,因此作为抗蚀剂下层膜形成用组合物是有用的。
Claims (7)
2.如权利要求1所述的抗蚀剂下层膜形成用组合物,所述式(A)中的X包含1个以上苯环、萘环、蒽环、芘环或它们的组合。
3.如权利要求1所述的抗蚀剂下层膜形成用组合物,所述式(A)中的n个Y分别独立地包含具有至少1个羟基的苯环、萘环、蒽环或芘环或它们的组合。
4.如权利要求1所述的抗蚀剂下层膜形成用组合物,所述式(A)中的n为2。
5.如权利要求1所述的抗蚀剂下层膜形成用组合物,其中所述溶剂的沸点为160℃以上。
6.一种抗蚀剂下层膜,其特征在于,是由权利要求1~5中任一项所述的抗蚀剂下层膜形成用组合物形成的涂膜的烧成物。
7.一种半导体装置的制造方法,包含:
使用权利要求1~5中任一项所述的抗蚀剂下层膜形成用组合物在半导体基板上形成抗蚀剂下层膜的步骤,
在所形成的抗蚀剂下层膜之上形成抗蚀剂膜的步骤,
通过对所形成的抗蚀剂膜照射光或电子束并显影,而形成抗蚀剂图案的步骤,
经由所形成的抗蚀剂图案来蚀刻所述抗蚀剂下层膜、进行图案化的步骤,以及
经由图案化了的抗蚀剂下层膜来加工半导体基板的步骤。
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