CN109485590B - 单体、聚合物、抗蚀剂组合物和图案化方法 - Google Patents
单体、聚合物、抗蚀剂组合物和图案化方法 Download PDFInfo
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- CN109485590B CN109485590B CN201811066172.3A CN201811066172A CN109485590B CN 109485590 B CN109485590 B CN 109485590B CN 201811066172 A CN201811066172 A CN 201811066172A CN 109485590 B CN109485590 B CN 109485590B
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 23
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- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 32
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- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 12
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
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- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 5
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 5
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- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
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- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
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- 238000010943 off-gassing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
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- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 150000003440 styrenes Chemical class 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
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- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/22—Oxygen
- C08F212/24—Phenols or alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明为单体、聚合物、抗蚀剂组合物和图案化方法。提供了具有式(A)的单体。RA为H、甲基或三氟甲基,X1为单键,醚键、酯键或酰胺键,Ra为C1‑C20一价烃基,Rb为H或酸不稳定性基团,X为卤素,n为1至4的整数,m为0至3的整数,和1≤n+m≤4。包含衍生自所述单体的聚合物的抗蚀剂组合物具有对高能辐射、特别是EUV的高的感光度。
Description
相关申请的交叉引用
本非临时申请在美国法典第35卷第119节(a)款下要求2017年9月13日于日本提交的第2017-175900号专利申请的优先权,所述专利申请的全部内容通过引用并入本文。
技术领域
本发明涉及单体、聚合物、包含所述聚合物的抗蚀剂组合物和使用所述组合物的图案化方法。
背景技术
为了满足LSI的更高集成度和运行速度的要求,减小图案尺度的努力正在迅速进行。用于智能电话中的逻辑器件推动了微型化技术。使用基于ArF光刻法的多重图案化光刻法工艺大规模制造10nm节点的逻辑器件。
在将光刻法应用至下一代的7nm或5nm节点器件中,多重图案化光刻法的重合精确度和增加的花费变得显著。期望能够减少曝光数的EUV光刻法的到来。
因为极紫外线(EUV)的波长(13.5nm)短于ArF准分子激光的波长(193nm)的1/10,所以EUV光刻法实现高的光对比度,由此可预期高的分辨率。因为EUV的短的波长和高的能量密度,产酸剂对小剂量的光子敏感。EUV曝光出现的光子的数被认为是ArF曝光的1/14。在EUV光刻法中,线图案的边缘粗糙度(LWR)和孔图案的临界尺寸均匀性(CDU)由于光子数的改变而劣化的现象成为问题。
旨在降低光子数的改变,尝试使抗蚀剂更具吸收性,从而增加抗蚀剂中吸收的光子数。
专利文献1公开了经卤素取代的苯乙烯系树脂。卤素原子中,碘对波长13.5nm的EUV辐射为高度吸收性。最近专利文献2和3提出将碘取代的树脂用作EUV抗蚀剂组分。令人遗憾地,并非仅通过引入碘增加吸收的光子数而就能够获得较高的感光度。关于在EUV曝光中产酸,非专利文献1报道了碘化的苯乙烯的产酸效率仅为羟基苯乙烯的14%。
引用列表
专利文献1:JP-A H05-204157
专利文献2:JP-A 2015-161823
专利文献3:WO 2013/024777
非专利文献1:Jpn.J.Appl.Physics,Vol.46,No.7,第L142-L144页,2007
发明内容
对于酸催化的化学增幅抗蚀剂,期望开发提供高感光度和降低LWR或改进孔图案的CDU的抗蚀剂组合物。
本发明的目的在于提供抗蚀剂组合物和使用所述抗蚀剂组合物的图案形成方法,所述抗蚀剂组合物在曝光至高能辐射,特别是EUV时显示出高的感光度。另一目的在于提供充当抗蚀剂组合物中的基础树脂的聚合物,和可以被用作所述聚合物的起始原料的单体。
发明人已发现由包含作为基础树脂的聚合物的抗蚀剂组合物获得更好的结果,所述聚合物在键合至聚合物主链的芳环上的碳原子的邻位具有酚羟基并且在芳环上具有卤素原子,所述酚羟基任选地用酸不稳定性基团保护。当曝光至高能辐射,特别是EUV时,所述抗蚀剂组合物显示出高感光度、改进的CDU和宽的加工余裕。
在一个方面,本发明提供了具有式(A)的单体。
其中,RA为氢、甲基或三氟甲基,X1为单键,醚键、酯键或酰胺键,Ra为C1-C20一价烃基,其构成中任意亚甲基结构部分可以被醚键或羰基结构部分所替代,在包括至少两个Ra时,两个相邻的Ra可以键合在一起以与它们所连接的碳原子形成脂环结构,Rb为氢或酸不稳定性基团,X为卤素,n和m为在以下范围的整数:1≤n≤4,0≤m≤3和1≤n+m≤4。
优选地,X1为单键和X为碘。
在第二方面,本发明提供了聚合物,其包含在侧链上具有由式(B)表示的部分结构的重复单元。
其中,X1、Ra、Rb、X、n和m如上文所定义,虚线表示到聚合物主链的价键。
优选地,重复单元具有式(a)。
其中,RA、Ra、Rb、X1、X、n和m如上文所定义。
优选地,X1为单键,和X为碘。
聚合物可以另外包含具有能够在酸的作用下极性转换的基团的重复单元。具有能够在酸的作用下极性转换的基团的重复单元优选由式(b1)或(b2)表示。
其中,RA如上文所定义;Y1为单键,亚苯基,亚萘基或含有醚键、酯键或内酯环的C1-C12连接基;Y2为单键、酯键或酰胺键;R1和R2各自独立地为酸不稳定性基团;R3为氟、三氟甲基、氰基、C1-C6烷基、C1-C6烷氧基、C2-C7酰基、C2-C7酰氧基或C2-C7烷氧羰基;R4为单键或其中至少一个碳原子可以被醚键或酯键替代的C1-C6亚烷基;p为1或2,和q为0至4的整数。
所述聚合物可以另外包含具有粘合性基团的重复单元,所述粘合性基团选自羟基、羧基、内酯环、碳酸酯、硫代碳酸酯、羰基、环状缩醛、醚键、酯键、磺酸酯键、氰基、酰胺、-O-C(=O)-S-和-O-C(=O)-NH-。
聚合物可以另外包含选自具有式(d1)、(d2)和(d3)的重复单元的至少一种类型的重复单元。
其中,RA如上文所定义。R11和R12各自独立地为可以含有杂原子的C1-C20一价烃基,R11和R12可以键合在一起以与它们所连接的硫原子形成环。L1为单键、亚苯基、-C(=O)-L11-L12-或-O-L12-,L11为-O-或-NH-,L12为亚苯基,或可以含有羰基、酯键、醚键或羟基结构部分的C1-C6二价脂族烃基。L2为单键或-L21-C(=O)-O-,L21为可以含有杂原子的C1-C20二价烃基。L3为单键、亚甲基、亚乙基、亚苯基或氟化的亚苯基、-C(=O)-L31-L32-或-O-L32-,L31为-O-或-NH-,L32为亚苯基或可以含有羰基、酯键、醚键或羟基结构部分的C1-C6二价脂族烃基。M-为非亲核性反离子。
Q+为具有式(d4)的锍阳离子或具有式(d5)的碘鎓阳离子:
其中,R13至R17各自独立地为可以含有杂原子的C1-C20一价烃基,R13、R14和R15的任意两个可以键合在一起以与它们所键合的硫原子形成环。
在第三方面,本发明提供了抗蚀剂组合物,其包含含有上文定义的聚合物的基础树脂,有机溶剂和产酸剂;或抗蚀剂组合物,其包含含有上文定义并且另外包含单元(d1)至(d3)的聚合物的基础树脂,和有机溶剂。
抗蚀剂组合物可以另外包含猝灭剂和表面活性剂。
在第四方面,本发明提供了图案形成方法,所述方法包括以下步骤:将上文定义的抗蚀剂组合物涂覆至基底上,烘焙以形成抗蚀剂膜,将抗蚀剂膜曝光至高能辐射,和将经曝光的抗蚀剂膜用显影剂显影。
典型地,高能辐射为i-线、KrF准分子激光、ArF准分子激光、EB或波长3至15nm的EUV。
发明的有益效果
当将包含本发明的聚合物作为基础树脂的抗蚀剂组合物暴露至高能辐射,特别是波长13.5nm的EUV时是有利的。因为卤素,特别是碘对EUV是高吸收性,所以其在曝光期间有效地产生二次电子,所述二次电子被转移至产酸剂以诱导有效的产酸。这有助于更高的感光度。因为该聚合物在相对于主链的邻位具有酚羟基,所以其在碱性显影剂中具有适当的溶解速率。因此可以设计具有高的感光度和改进的CDU的抗蚀剂材料。
具体实施方式
如本文中所使用,除非上下文另有明确规定,否则单数形式“一种”、“一个”和“该”包括多个指代对象。标记(Cn-Cm)表示每个基团包含n至m个碳原子的基团。如本文中所使用,术语“碘化(的)”或“氟化(的)”表明化合物含有碘或氟。Me表示甲基,和Ac表示乙酰基。
缩写和首字母缩略词具有以下含义。
EB:电子束
EUV:极紫外线
Mw:重均分子量
Mn:数均分子量
Mw/Mn:分子量分布或分散度
GPC:凝胶渗透色谱法
PEB:曝光后烘焙
PAG:光致产酸剂
LWR:线宽粗糙度
LER:线边缘粗糙度
CDU:临界尺寸均匀度
单体
本发明的一个实施方案为具有式(A)的聚合性单体。
在式(A)中,RA为氢、甲基或三氟甲基。X1为单键、醚键、酯键或酰胺键。X1优选地为单键,因为获得牢固的聚合物主链。在X1为酯键或酰胺键时,优选酯键或酰胺键中的氧原子或氮原子与芳环上的碳原子连接。
在式(A)中,Ra为C1-C20一价烃基,其构成中任意亚甲基结构部分可以被醚键或羰基结构部分所替代。在包括至少两个Ra时,两个相邻的Ra可以键合在一起以与它们所连接的碳原子形成脂环结构。
C1-C20一价烃基可以为直链、支链或环状。合适的实例包括直链或支链的烷基,如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、2-乙基己基和正辛基;和一价环脂族饱和烃基如环戊基、环己基、降冰片基、三环癸基和金刚烷基。
在两个相邻的Ra键合在一起以与它们所连接的碳原子形成脂环结构时,合适的结构包括环丙烷环、环丁烷环、环戊烷环和环己烷环。
在式(A)中,Rb为氢或酸不稳定性基团。在Rb为酸不稳定性基团时,尽管并非重要,但期望的是,酸不稳定性基团与相邻的氧原子形成缩醛或叔醚结构。
在式(A)中,X为卤素。示例性的卤素为氟、氯、溴和碘。尤其是因为EUV吸收的高效率而优选溴和碘,其中最优选碘。
在式(A)中,n和m为在以下范围的整数:1≤n≤4,0≤m≤3和1≤n+m≤4。优选地,n为2至4的整数,和m为0。
具有式(A)的单体的实例示于下文,但不限于此。其中,RA和Rb如上文所定义。
单体的特征在于在相对于键合至聚合性基团的芳环上的碳原子的邻位具有酚羟基或用酸不稳定性基团保护的酚羟基,和具有键合至芳环上的碳原子的卤素原子。当将单体引入聚合物时,卤素原子在曝光期间有效地产生二次电子,其被转移至产酸剂以诱导有效的酸产生。这有助于较高的感光度。卤素原子中,碘对于高能辐射、特别是波长13.5nm的EUV最具吸收性。因此,当卤素为碘时,感光度增强效应变得最大。另外在相对于聚合物主链的邻位的酚羟基的存在保证了用碱性显影剂显影时的适当的聚合物溶解速率。当将酚羟基用酸不稳定性基团保护时,在酸的作用下发生脱保护反应,由此恢复酚羟基,这有助于曝光区域和未曝光区域之间的对比度的改进。由于这些机理的增效作用,可以设计具有改进的CDU的抗蚀剂组合物。
具有式(A)的单体可以例如通过以下反应来合成,尽管合成路线不限于此。作为典型实例,以下参考具有式(A)的单体(A’)描述该合成,其中RA为氢和X1为单键。
其中,Ra、Rb、X、n和m如上文所定义。
通过Wittig反应将作为起始反应物的芳族化合物上的甲酰基转变成乙烯基获得单体(A’)。
可以以标准程序进行反应。例如,通过将Wittig试剂前体如甲基三苯基溴化鏻溶于醚溶剂如四氢呋喃或***中,并且将碱添加至所述溶液同时如果必要则冷却所述溶液来制备Wittig试剂。本文中所使用的碱期望为强碱,其选自例如烷基锂试剂,如正丁基锂和碱金属盐如叔丁醇钾。一旦在体系中制备Wittig试剂,就将反应物溶于醚溶剂如四氢呋喃或***中,将其滴加至该体系并且熟化,生成单体(A’)。
考虑到其被芳族化合物上的羟基失活,按每摩尔芳族化合物计,所使用的Wittig试剂的量优选为2.0至5.0摩尔,更优选2.0至3.0摩尔。超过5.0摩尔的量由于增加的花费而可能是经济上不利的并且使得除去副产物三苯基氧化膦变得困难。还可以使用具有用酸不稳定性基团保护的羟基的反应物。如果必要可以进行冷却或加热的同时进行反应,典型地在0℃至接近溶剂的沸点的温度。出于收率的观点期望的是,通过气相色谱法(GC)或硅胶薄层色谱法(TLC)监控反应过程确定反应时间,从而驱动反应完全。通常,反应时间为约0.5至2小时。从反应混合物中通过普通含水处理回收单体(A’)。如果必要,可以通过标准技术如蒸馏、色谱法或重结晶来纯化单体。
在另一路线中,如下文所示通过以下获得单体(A’):借助于有机锂试剂(如甲基锂)或有机镁试剂(如甲基氯化镁)对作为起始反应物的芳族化合物上的甲酰基进行加成反应,使所得化合物(A”)脱水以将相关基团转变成乙烯基。
其中,Ra、Rb、X、n和m如上文所定义。
第一阶段为通过借助于有机锂试剂(如甲基锂)或有机镁试剂(如甲基氯化镁)对作为起始反应物的芳族化合物上的甲酰基进行加成反应形成化合物(A”)。
可以以标准程序进行反应。有机锂试剂(如甲基锂)或有机镁试剂(如甲基氯化镁)可以根据公知的配方在使用前制备或商业上能够得到。在使用商业上能够得到的试剂时,可以将其用溶剂如四氢呋喃或***稀释,这取决于购买的试剂浓度。通过将芳族化合物的溶液滴加至有机金属试剂,能够获得化合物(A”)。
考虑到其因芳族化合物上的羟基而失活,按每摩尔芳族化合物计,所使用的有机金属试剂的量优选为2.0至4.0摩尔,更优选2.0至3.0摩尔。超过4.0摩尔的量由于增加的花费经济上可能不利。如果必要可以冷却或加热的同时进行反应,并且典型地在0℃至50℃的温度。出于收率的观点期望的是,通过GC或硅胶TLC监控反应过程确定反应时间,从而推动反应完成。通常,反应时间为约0.5至12小时。从反应混合物中通过普通含水处理回收单体(A”)。如果必要,可以通过标准技术如蒸馏、色谱法或重结晶来纯化化合物。
第二阶段为通过在酸催化剂的存在下使化合物(A”)上的仲羟基脱水而形成单体(A’)。
可以以标准程序进行反应。通过将化合物(A”)溶于烃熔剂如正庚烷、甲苯或二甲苯中,向其中添加酸催化剂,和加热溶液以促进脱水反应能够获得单体(A’)。本文中使用的酸催化剂优选为强酸,特别是硫酸、硝酸、对甲苯磺酸或三氟甲磺酸。反应温度典型地为60℃至溶剂的沸点。优选地,将通过反应形成的水从体系馏除以加速反应。出于收率的观点期望的是通过GC或硅胶TLC监控反应过程确定反应时间,从而推动反应完成。通常,反应时间为约1至24小时。从反应混合物中通过普通含水处理回收单体(A’)。如果必要,可以通过标准技术如蒸馏、色谱法或重结晶来纯化单体。
聚合物
本发明还提供包含在侧链上具有由式(B)表示的部分结构的重复单元的聚合物。
在式(B)中,X1、Ra、Rb、X、n和m如上文所定义,并且虚线表示到聚合物主链的价键。优选地,X1为单键和X为碘。
专利文献2描述了包含衍生自碘化的对羟基苯乙烯或间羟基苯乙烯的重复单元的聚合物。在使用在主链的对位或间位具有酚羟基的苯乙烯结构单元时,形成具有从主链突出的酚羟基的结构。该结构提供了对碱性显影剂的更高的亲和力,由此预期聚合物在碱性显影剂中的溶解速率变得极高。经加速的溶解速率允许正型抗蚀剂甚至在未曝光区域中部分溶解,导致LWR和CDU劣化。
具有式(B)的部分结构的重复单元优选为衍生自具有式(A)的单体的单元,即具有式(a)的重复单元,在下文将其称为重复单元(a)。
其中,RA、X1、Ra、Rb、X、n和m如上文所定义。
本发明的聚合物可以另外包含具有能够在酸的作用下极性转换的基团的重复单元,在下文将其称为重复单元(b)。可以将包含含有重复单元(b)的聚合物的抗蚀剂组合物用作适合经由碱性显影形成正型图案的正型抗蚀剂组合物或适合经由有机溶剂显影形成负型图案的负型抗蚀剂组合物。
重复单元(b)优选为具有式(b1)的重复单元或具有式(b2)的重复单元。在下文将这些单元称为重复单元(b1)和(b2)。
其中,RA如上文所定义。Y1为单键,亚苯基,亚萘基或含有醚键、酯键或内酯环的C1-C12连接基。Y2为单键、酯键或酰胺键。R1和R2各自独立地为酸不稳定性基团。R3为氟,三氟甲基,氰基,C1-C6烷基,C1-C6烷氧基,C2-C7酰基,C2-C7酰氧基,或C2-C7烷氧羰基。R4为单键或其中至少一个碳原子可以被醚键或酯键替代的C1-C6亚烷基,p为1或2,和q为0至4的整数。
重复单元(b1)的说明性、非限制性的实例示于下文。其中,RA和R1如上文所定义。
重复单元(b2)的说明性、非限制性实例示于下文。其中,RA和R2如上文所定义。
式(b1)和(b2)中由R1和R2表示的酸不稳定性基团可以选自各种各样的这样的基团,例如描述于JP-A 2013-080033(USP 8,574,817)和JP-A 2013-083821(USP 8,846,303)中的那些基团。
典型的酸不稳定性基团为下式(AL-1)至(AL-3)的基团。
在式(AL-1)和(AL-2)中,RL1和RL2各自独立地为一价烃基,其可以含有杂原子如氧、硫、氮或氟。一价烃基可以为直链、支链或环状,并且优选为1至40个碳原子、更优选1至20个碳原子的烷基。在式(AL-1)中,“a”为0至10的整数,特别是1至5。
在式(AL-2)中,RL3和RL4各自独立地为氢或其可以含有杂原子如氧、硫、氮或氟的一价烃基。一价烃基可以为直链、支链或环状,并且优选为1至20个碳原子的烷基。RL2、RL3和RL4的任意两个可以键合在一起以与它们所连接的碳原子或碳原子和氧原子形成环,特别是脂族环,所述环含有3至20个碳原子、优选4至16个碳原子。
在式(AL-3)中,RL5、RL6和RL7各自独立地为一价烃基,其可以含有杂原子如氧、硫、氮或氟。一价烃基可以为直链、支链或环状,并且优选为1至20个碳原子的烷基。RL5、RL6和RL7的任意两个可以键合在一起以与它们所连接的碳原子形成环,特别是脂族环,所述环含有3至20个碳原子、优选4至16个碳原子。
作为重复单元(b),还可以使用由于借助于酸的脱水反应从亲水性转换至疏水性的重复单元,将其称为重复单元(b3)。当使用重复单元(b3)时,可以将本发明的抗蚀剂组合物用作适合经由碱性显影形成负型图案的负型抗蚀剂组合物。
由其衍生出重复单元(b3)的单体的实例示于下文,但不限于此。其中,RA如上文所定义。
在优选的实施方案中,聚合物可以另外包含具有粘合性基团的重复单元(c)。粘合性基团选自羟基、羧基、内酯环、碳酸酯、硫代碳酸酯、羰基、环状缩醛、醚键、酯键、磺酸酯键、氰基、酰胺、-O-C(=O)-S-和-O-C(=O)-NH-。由其衍生出重复单元(c)的单体的实例示于下文,但不限于此。其中,RA如上文所定义。
重复单元(c)中,优选具有羟基或内酯环的单元,更优选具有酚羟基或内酯环的单元。
在更优选的实施方案中,聚合物可以另外包含选自由下式(d1)至(d3)表示的重复单元中的至少一种类型的重复单元,也将其称为重复单元(d1)至(d3)。
在式(d1)至(d3)中,RA如上文所定义。L1为单键、亚苯基、-C(=O)-L11-L12-或-O-L12-,其中L11为-O-或-NH-,和L12为亚苯基,或其可以含有羰基、酯键、醚键或羟基结构部分C1-C6二价脂族烃基。L2为单键或-L21-C(=O)-O-,其中L21为可以含有杂原子的C1-C20二价烃基。L3为单键、亚甲基、亚乙基、亚苯基或氟化的亚苯基、-C(=O)-L31-L32-或-O-L32-,其中L31为-O-或-NH-,和L32为亚苯基,或C1-C6二价脂族烃基,所述C1-C6二价脂族烃基可以含有羰基、酯键、醚键或羟基结构部分。M-为非亲核性反离子。
由L12和L32表示的二价脂族烃基可以为直链、支链或环状。实例包括直链、支链或环状的二价饱和脂族烃基,如亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,2-二基、丙烷-2,2-二基、丙烷-1,3-二基、2-甲基丙烷-1,3-二基、丁烷-1,3-二基、丁烷-2,3-二基、丁烷-1,4-二基、戊烷-1,3-二基、戊烷-1,4-二基、2,2-二甲基丙烷-1,3-二基、戊烷-1,5-二基、己烷-1,6-二基、环戊烷-1,2-二基、环戊烷-1,3-二基和环己烷-1,6-二基;和直链、支链或环状的二价不饱和脂族烃基,如乙烯-1,2-二基、1-丙烯-1,3-二基、2-丁烯-1,4-二基、1-甲基-1-丁烯-1,4-二基和2-环己烯-1,4-二基。
任选含杂原子的二价烃基L21可以为直链、支链或环状。所述基团的说明性的非限制性实例示于下文。
在式(d2)和(d3)中,Q+为具有式(d4)的锍阳离子或具有式(d5)的碘鎓阳离子。
在式(d1)、(d4)和(d5)中,R11至R17各自独立地为可以含有杂原子的C1-C20一价烃基。R11和R12可以键合在一起以与它们所键合的硫原子形成环。R13、R14和R15的任意两个可以键合在一起以与它们所键合的硫原子形成环。
一价烃基R11至R17可以为直链、支链或环状。合适的实例包括直链或支链的烷基,如甲基、乙基、正丙基、异丙基、正丁基、叔丁基;环状饱和一价烃基,如环丙基、环戊基、环己基、环丙基甲基、4-甲基环己基、环己基甲基、降冰片基和金刚烷基;直链或支链的烯基,如乙烯基、1-丙烯基、2-丙烯基、丁烯基和己烯基;环状不饱和一价烃基,如环己烯基;芳基,如苯基、萘基和噻吩基;和芳烷基,如苄基、1-苯基乙基和2-苯基乙基,其中优选芳基。还包括其中至少一个氢被含有杂原子如氧、硫、氮或卤素的结构部分取代或其中至少一个碳被含有杂原子如氧、硫或氮的结构部分取代的前述基团,使得所述基团可以含有羟基、氰基、硝基、羰基、磺酰基、醚键、酯键、磺酸酯键、碳酸酯、内酯环、磺内酯环、羧酸酐或卤代烷基结构部分。
将产酸剂键合至聚合物主链有效降低了酸扩散并且防止分辨率由于酸扩散导致的模糊而降低。另外,因为产酸剂均匀地分散而改进了边缘粗糙度(LER、LWR)。
在R11和R12一起与硫原子形成环时,或在R13、R14和R15的任意两个一起与硫原子形成环时,所述环的实例示于下文,但不限于此。
在式中,R18为可以含有杂原子的C1-C20一价烃基。合适的一价烃基如上文对R11至R17所示例。
式(d4)的锍阳离子的说明性的非限制性实例在下文给出。
式(d5)的碘鎓阳离子的说明性、非限制性实例在下文给出。
由M-表示的非亲核性反离子的实例包括卤离子,如氯离子和溴离子;氟代烷基磺酸根离子,如三氟甲磺酸根、1,1,1-三氟乙烷磺酸根和九氟丁烷磺酸根;芳基磺酸根离子,如甲苯磺酸根、苯磺酸根、4-氟苯磺酸根和1,2,3,4,5-五氟苯磺酸根;烷基磺酸根离子,如甲磺酸根和丁磺酸根;酰亚胺离子,如双(三氟甲基磺酰)亚胺、双(全氟乙基磺酰)亚胺和双(全氟丁基磺酰)亚胺;甲烷阴离子(methide),如三(三氟甲基磺酰)甲烷阴离子和三(全氟乙基磺酰)甲烷阴离子。
还包括由式(F-1)表示的在α位氟化的磺酸根离子和由式(F-2)表示的在α和β位氟化的磺酸根离子。
R19-CF2-SO3 - (F-I)
在式(F-1)中,R19为氢或C1-C20烷基、C2-C20烯基或C6-C20芳基,其可以具有醚键、酯键、羰基结构部分、内酯环或氟原子。其中所述烷基和烯基可以为直链、支链或环状。
在式(F-2)中,R20为氢或C1-C30烷基、C2-C30酰基、C2-C20烯基、C6-C20芳基或C6-C20芳氧基,其可以具有醚键、酯键、羰基结构部分或内酯环。其中所述烷基、酰基和烯基可以为直链、支链或环状。
重复单元(d1)的实例在下文给出,但不限于此。注意RA如上文所定义。
重复单元(d2)的实例示于下文,但不限于此。注意RA如上文所定义。
重复单元(d3)的实例示于下文,但不限于此。注意RA如上文所定义。
除了重复单元(d1)至(d3)以外,本发明的聚合物可以另外包含如JP 5548473第[0129]-[0151]中所描述的具有键合至主链的磺酸、亚氨酸或甲基化物酸阴离子的重复单元或具有键合至主链的锍阳离子的重复单元或如WO 2011/070947第[0034]-[0038]段中所描述的衍生自含有磺酸阴离子的单体的重复单元。
重复单元(d1)至(d3)起产酸剂的作用。将产酸剂键合至聚合物主链有效地降低了酸扩散并且防止了分辨率由于酸扩散的模糊而下降。此外,边缘粗糙度(LER、LWR)因为产酸剂均匀地分散而得以改进。
在优选的实施方案中,该聚合物可以另外包含由下式(e1)至(e5)表示的衍生自茚、苊烯、色酮、香豆素或降冰片二烯的重复单元(e)。
其中,R31独立的为C1-C30烷基、C1-C30卤代烷基、羟基、C1-C30烷氧基、C1-C30酰基、C2-C30烷氧羰基、C6-C10芳基、卤素或1,1,1,3,3,3-六氟-2-丙醇基,和h为0或1。R32为氢、C1-C30烷基、C1-C30卤代烷基、羟基、C1-C30烷氧基、C1-C30酰基、C2-C30烷氧羰基、C6-C10芳基、卤素或1,1,1,3,3,3-六氟-2-丙醇基。X0为亚甲基、氧或硫。前述烷基、卤代烷基、烷氧基、酰基和烷氧羰基可以为直链、支链或环状。
在优选的实施方案中,聚合物可以另外包含衍生自苯乙烯、乙烯基萘、乙烯基蒽、乙烯基芘或亚甲基茚满化合物的重复单元(f)。
在该聚合物中,重复单元(a)至(f)的份额优选在以下范围:0<a<1.0,0≤b1<1.0,0≤b2<1.0,0<b1+b2<1.0,0≤c≤0.9,0≤d1≤0.5,0≤d2≤0.5,0≤d3≤0.5,0≤d1+d2+d3≤0.5,0≤e1≤0.5,0≤e2≤0.5,0≤e3≤0.5,0≤e4≤0.5,0≤e5≤0.5,0≤e1+e2+e3+e4+e5≤0.5和0≤f≤0.5;更优选0.02≤a≤0.8,0≤b1≤0.7,0≤b2≤0.7,0.1≤b1+b2≤0.7,0<c≤0.8,0≤d1≤0.4,0≤d2≤0.4,0≤d3≤0.4,0≤d1+d2+d3≤0.4,0≤e1≤0.4,0≤e2≤0.4,0≤e3≤0.4,0≤e4≤0.4,0≤e5≤0.4,0≤e1+e2+e3+e4+e5≤0.4和0≤f≤0.4;甚至更优选0.05≤a≤0.7,0≤b1≤0.6,0≤b2≤0.6,0.1≤b1+b2≤0.6,0<c≤0.7,0≤d1≤0.3,0≤d2≤0.3,0≤d3≤0.3,0≤d1+d2+d3≤0.3,0≤e1≤0.3,0≤e2≤0.3,0≤e3≤0.3,0≤e4≤0.3,0≤e5≤0.3,0≤e1+e2+e3+e4+e5≤0.3和0≤f≤0.3。注意,a+b1+b2+c+d1+d2+d3+e1+e2+e3+e4+e5+f=1。
聚合物应当优选具有在1,000至500,000、且更优选2,000至30,000范围内的重均分子量(Mw),其通过GPC相对于聚苯乙烯标样使用四氢呋喃(THF)溶剂测量。所述范围的Mw保证了抗蚀剂组合物充分耐热和碱可溶性。
如果聚合物具有宽的分子量分布或分散度(Mw/Mn),这表明存在较低的分子量和较高分子量的聚合物级分,则存在外来物质留在图案上或图案轮廓劣化的可能性。随着图案尺度变得越精细Mw和Mw/Mn的影响变得越强。因此,该聚合物应当优选具有1.0至2.0,特别是1.0至1.5的窄的分散度(Mw/Mn),以提供适合于微图案化至小的特征尺寸的抗蚀剂组合物。
该聚合物可以通过任意期望的方法来合成,例如通过将选自对应于重复单元(a)至(f)的单体中的一种或多种单体溶于有机溶剂中,向其中添加自由基聚合引发剂,并加热以聚合。可以用于聚合的有机溶剂的实例包括甲苯、苯、THF、***、二噁烷、环己烷、环戊烷、甲基乙基酮和γ-丁内酯。本文中使用的聚合引发剂的实例包括2,2’-偶氮二异丁腈(AIBN)、2,2’-偶氮二(2,4-二甲基戊腈)、2,2-偶氮二(2-甲基丙酸甲酯)、过氧化苯甲酰和过氧化月桂酰。优选地,反应温度为50至80℃和反应时间为2至100小时,更优选5至20小时。
当使带有羟基的单体共聚时,可以使用其中羟基已被易用酸脱保护的缩醛基团(典型地为乙氧基乙氧基)替代的相应单体,并且在聚合之后用弱酸和水脱保护。替代性地,羟基可以已被乙酰基、甲酰基或新戊酰基替代,并且在聚合之后碱性水解。
当使羟基苯乙烯或羟基乙烯基萘共聚时,可以为替代性方法。具体而言,使用乙酰氧基苯乙烯或乙酰氧基乙烯基萘替代羟基苯乙烯或羟基乙烯基萘,并且在聚合之后,将乙酰氧基通过碱性水解脱保护,由此将相关的单元转变成羟基苯乙烯单元或羟基乙烯基萘单元。对于碱性水解,可以使用碱,如氨水或三乙胺。优选地,反应温度为-20℃至100℃,更优选0℃至60℃,和反应时间为0.2至100小时,更优选0.5至20小时。
抗蚀剂组合物
本发明的另外的实施方案为抗蚀剂组合物,其包含含有上文定义的聚合物的基础树脂和有机溶剂。所述基础树脂可以为组成比、Mw和/或Mw/Mn不同的本发明的聚合物的共混物。
有机溶剂
本文中所使用的有机溶剂的实例描述于JP-A 2008-111103第[0144]至[0145]段(USP 7,537,880)中。合适的有机溶剂包括酮,如环己酮和甲基-2-正戊基酮;醇,如3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇和1-乙氧基-2-丙醇;醚,如丙二醇单甲醚、乙二醇单甲醚、丙二醇单***、乙二醇单***、丙二醇二甲醚和二乙二醇二甲醚;酯,如丙二醇单甲醚乙酸酯(PGMEA)、丙二醇单***乙酸酯、乳酸乙酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸叔丁酯、丙酸叔丁酯和丙二醇单叔丁醚乙酸酯;和内酯,如γ-丁内酯,其可以单独或混合使用。
优选按每100重量份的基础树脂计以50至10,000重量份,更优选100至5,000重量份的量使用有机溶剂。
产酸剂
抗蚀剂组合物可以包括产酸剂(也被称为添加类型的产酸剂),从而使得该组合物起化学增幅抗蚀剂组合物的作用。本文中所使用的典型的产酸剂为能够响应于光化辐射光或辐射而产生酸的光致产酸剂(PAG)。在作为基础树脂的聚合物含有重复单元(d1)至(d3)时,即当产酸剂结合在聚合物中时,添加型的产酸剂并非必要。
PAG为能够在曝光至高能辐射时产生酸的任意化合物。合适的PAG包括锍盐、碘鎓盐、磺酰基重氮甲烷、N-磺酰氧基酰亚胺和O-磺酸肟酯产酸剂。示例性PAG描述于USP 7,537,880(JP-A 2008-111103第[0122]-[0142]段)中。
作为PAG,还优选使用具有式(1-1)的锍盐和具有式(1-2)的碘鎓盐。
在式(1-1)和(1-2)中,R101、R102、R103、R104和R105各自独立地为可以含有杂原子的C1-C20一价烃基,并且R101、R102和R103的任意两个可以键合在一起以与它们所连接的硫原子形成环。所述一价烃基可以为直链、支链或环状,并且其实例如上文对于式(d1)、(d4)和(d5)中的R11至R17所示例。
具有式(1-1)的锍盐中的阳离子结构部分的实例如上文对具有式(d4)的阳离子所示例。具有式(1-2)的碘鎓盐中的阳离子结构部分的实例如上文对具有式(d5)的阳离子所示例。
在式(1-1)和(1-2)中,X-为选自式(1A)至(1D)的阴离子。
Rfa-CF2-SO3 - (1A)
在式(1A)中,Rfa为氟或可以含有杂原子的C1-C40一价烃基。所述一价烃基可以为直链、支链或环状,并且其实例如下文将对R105所示例。
式(1A)的阴离子中,优选具有式(1A’)的结构。
在式(1A’)中,R104为氢或三氟甲基,优选三氟甲基。R105为可以含有杂原子的C1-C38一价烃基。合适的杂原子包括氧、氮、硫和卤素,其中优选氧。那些6至30个碳原子的一价烃基是优选的,因为在精细图案形成中可得到高的分辨率。所述一价烃基可以为直链、支链或环状。合适的一价烃基包括直链或支链烷基,如甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、新戊基、环戊基、己基、庚基、2-乙基己基、壬基、十一烷基、十三烷基、十五烷基、十七烷基和二十烷基;一价饱和环脂族烃基,如环己基、1-金刚烷基、2-金刚烷基、1-金刚烷基甲基、降冰片基、降冰片基甲基、三环癸基、四环十二烷基、四环十二烷基甲基和二环己基甲基;一价不饱和脂族烃基,如烯丙基和3-环己烯基;和芳烷基如苄基和二苯基甲基。合适的含杂原子的一价烃基包括四氢呋喃基、甲氧基甲基、乙氧基甲基、甲硫基甲基、乙酰氨基甲基、三氟乙基、(2-甲氧基乙氧基)甲基、乙酰氧基甲基、2-羧基-1-环己基、2-氧代丙基、4-氧代-1-金刚烷基和3-氧代环己基。还包括其中至少一个氢被含有杂原子如氧、硫、氮或卤素的结构部分取代或其中至少一个碳被含有杂原子如氧、硫或氮的结构部分取代的前述基团,使得所述基团可以含有羟基、氰基、硝基、羰基、醚键、酯键、磺酸酯键、碳酸酯、内酯环、磺内酯环、羧酸酐或卤代烷基结构部分。
关于具有式(1A’)的阴离子的锍盐的合成,参考JP-A 2007-145797、JP-A 2008-106045、JP-A 2009-007327和JP-A 2009-258695。还有用的是描述于JP-A 2010-215608、JP-A 2012-041320、JP-A 2012-106986和JP-A 2012-153644中的锍盐。
具有式(1A)的阴离子的实例示于下文,但不限于此。
在式(1B)中,Rfb1和Rfb2各自独立地为氟或可以含有杂原子的C1-C40一价烃基。所述一价烃基可以为直链、支链或环状,并且其实例如上文对R105所示例。优选地,Rfb1和Rfb2各自为氟或直链C1-C4氟化烷基。Rfb1和Rfb2的一对可以键合在一起以与它们所连接的连接基(-CF2-SO2-N--SO2-CF2-)形成环,并且该对优选为氟化亚乙基或氟化亚丙基。
在式(1C)中,Rfc1、Rfc2和Rfc3各自独立地为氟或可以含有杂原子的C1-C40一价烃基。所述一价烃基可以为直链、支链或环状,并且其实例如上文对R105所示例。优选地,Rfc1、Rfc2和Rfc3各自为氟或直链C1-C4氟化烷基。Rfc1和Rfc2的一对可以键合在一起以与它们所连接的连接基(-CF2-SO2-C--SO2-CF2-)形成环,并且该对优选为氟化亚乙基或氟化亚丙基。
在式(1D)中,Rfd为可以含有杂原子的C1-C40一价烃基。所述一价烃基可以为直链、支链或环状,并且其实例如上文对R105所示例。
关于具有式(1D)的阴离子的锍盐的合成,参考JP-A 2010-215608和JP-A 2014-133723。
具有式(1D)的阴离子的实例示于下文,但不限于此。
具有式(1D)的阴离子的化合物因为其在磺基α位不含氟而在β位具有两个三氟甲基,所以具有足够的酸强度以裂解基础聚合物中的酸不稳定性基团。因此所述化合物为有用的PAG。
另外,具有式(2)的化合物也可用作PAG。
在式(2)中,R201和R202各自独立地为可以含有杂原子的C1-C30一价烃基。R203为可以含有杂原子的C1-C30二价烃基。R201、R202和R203的任意两个可以键合在一起以与它们所连接的硫原子形成环。LA为单键或醚键或可以含有杂原子的C1-C20二价烃基。XA、XB、XC和XD各自独立地为氢、氟或三氟甲基,前提是XA、XB、XC和XD的至少一个为氟或三氟甲基,和k为0至3的整数。
所述一价烃基可以为直链、支链或环状的并且包括直链或支链烷基,如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、叔戊基、正己基、正辛基、正壬基、正癸基和2-乙基己基;一价饱和环状烃基,如环戊基、环己基、环戊基甲基、环戊基乙基、环戊基丁基、环己基甲基、环己基乙基、环己基丁基、降冰片基、氧杂降冰片基、三环[5.2.1.02,6]癸基和金刚烷基;和芳基,如苯基、萘基和蒽基。还包括其中至少一个氢被杂原子如氧、硫、氮或卤素取代或其中至少一个碳被含有杂原子如氧、硫或氮的结构部分取代的前述基团,使得所述基团可以含有羟基、氰基、硝基、羰基、醚键、酯键、磺酸酯键、碳酸酯、内酯环、磺内酯环、羧酸酐或卤代烷基结构部分。
二价烃基可以为直链、支链或环状,并且其实例包括线性或支化烷烃二基如亚甲基、亚乙基、丙烷-1,3-二基、丁烷-1,4-二基、戊烷-1,5-二基、己烷-1,6-二基、庚烷-1,7-二基、辛烷-1,8-二基、壬烷-1,9-二基、癸烷-1,10-二基、十一烷-1,11-二基、十二烷-1,12-二基、十三烷-1,13-二基、十四烷-1,14-二基、十五烷-1,15-二基、十六烷-1,16-二基、十七烷-1,17-二基;饱和环状二价烃基,如环戊烷二基、环己烷二基、降冰片烷二基和金刚烷二基;和不饱和环状二价烃基,如亚苯基和亚萘基。还包括其中至少一个氢原子被烷基如甲基、乙基、丙基、正丁基或叔丁基取代或其中至少一个氢原子被含有杂原子如氧、硫、氮或卤素的结构部分取代或其中至少一个碳原子被含有杂原子如氧、硫或氮的结构部分取代的前述基团,从而所述基团可以含有羟基、氰基、羰基、醚键、酯键、磺酸酯键、碳酸酯、内酯环、磺内酯环、羧酸酐或卤代烷基结构部分。合适的杂原子包括氧、氮、硫或卤素,其中优选氧。
具有式(2)的PAG中,优选具有式(2’)的那些。
在式(2’)中,LA如上文所定义。R为氢或三氟甲基,优选三氟甲基。R301、R302和R303各自独立地为氢或可以含有杂原子的C1-C20一价烃基。所述一价烃基可以为直链、支链或环状,并且其实例如上文对R105所示例。下标x和y各自为0至5的整数,和z为0至4的整数。
具有式(2)的PAG的实例示于下文,但不限于此。其中,R如上文所定义。
前述PAG中,具有式(1A’)或(1D)的阴离子的那些化合物因为降低的酸扩散和在抗蚀剂溶剂中的高溶解度是特别优选的,具有式(2’)的阴离子的那些化合物因为酸扩散最小化而是特别优选的。
具有式(3-1)和(3-2)的含碘化苯甲酰氧基的氟化磺酸的锍盐和碘鎓盐也可用作PAG。
在式(3-1)和(3-2)中,R401为氢、羟基、羧基、硝基、氰基、氟、氯、溴、氨基,或C1-C20烷基、C1-C20烷氧基、C2-C20烷氧基羰基、C2-C20酰氧基或C1-C4烷基磺酰氧基,其可以含有氟、氯、溴、羟基、氨基或烷氧基结构部分,或-NR407-C(=O)-R408或-NR407-C(=O)-O-R408,其中R407为氢或其可以含有卤素、羟基、烷氧基、酰基或酰氧基结构部分的C1-C6烷基,R408为C1-C16烷基或C2-C16烯基,或C6-C12芳基,其可以含有卤素、羟基、烷氧基、酰基或酰氧基结构部分。
X11在r=1时为单键或C1-C20二价连接基,或当r=2或3时为C1-C20三价或四价连接基,所述连接基任选地含有氧、硫或氮原子。Rf11至Rf14各自独立地为氢、氟或三氟甲基,Rf11至Rf14的至少一个为氟或三氟甲基,或Rf11与Rf12可以合在一起形成羰基。
R402、R403、R404、R405和R406各自独立地为C1-C12烷基、C2-C12烯基、C2-C12炔基、C6-C20芳基、C7-C12芳烷基或C7-C12芳氧基烷基,其中至少一个氢(一个或多个或甚至全部氢原子)可以被羟基、羧基、卤素、氰基、氧代、酰胺、硝基、磺内酯、砜或含锍盐的结构部分取代,或其中至少一个碳可以被醚键、酯键、羰基、碳酸酯或磺酸酯结构部分取代。R402和R403可以键合在一起以与它们所连接的硫原子形成环。下标r为1至3的整数,s为1至5的整数,和t为0至3的整数。
前述烷基、烷氧基、烷氧基羰基、酰氧基、烷基磺酰氧基、烯基和炔基可以为直链、支链或环状。
另外,具有式(3-3)和(3-4)的含碘化苯的氟化磺酸的锍盐和碘鎓盐也可用作PAG。
在式(3-3)和(3-4)中,R411各自独立地为羟基、C1-C20烷基或烷氧基、C2-C20酰基或酰氧基、氟、氯、溴、氨基或被烷氧基羰基取代的氨基。R412各自独立地为单键或C1-C4亚烷基。R413在u=1时为单键或为C1-C20二价连接基或当u=2或3时为C1-C20三价或四价连接基,所述连接基任选地含有氧、硫或氮原子。
Rf21至Rf24各自独立地为氢、氟或三氟甲基,Rf21至Rf24的至少一个为氟或三氟甲基,或Rf21与Rf22一起可以形成羰基。
R414、R415、R416、R417和R418各自独立地为C1-C12烷基、C2-C12烯基、C6-C20芳基或C7-C12芳烷基或芳基氧代烷基,其中至少一个氢(一个或多个或甚至全部氢原子)可以被羟基、羧基、卤素、氰基、氧代、酰胺、硝基、磺内酯、砜或含锍盐的结构部分取代,或其中至少一个碳可以被醚、酯、羰基、碳酸酯或磺酸酯结构部分取代。R414和R415可以键合在一起以与它们所连接的硫原子形成环。下标u为1至3的整数,v为1至5的整数,和w为0至3的整数。
前述烷基、烷氧基、酰基、酰氧基和烯基可以为直链、支链或环状。
具有式(3-1)或(3-3)的锍盐中的阳离子结构部分如上文对式(d4)中的阳离子结构部分所示例。具有式(3-2)或(3-4)的碘鎓盐中的阳离子结构部分如上文对式(d5)中的阳离子结构部分所示例。
具有式(3-1)至(3-4)的鎓盐中的阴离子结构部分的实例如下文所示,但不限于此。
当抗蚀剂组合物含有添加型的产酸剂时,所添加的产酸剂的适当的量按每100重量份的基础树脂计为0.1至50重量份、更优选1至40重量份。
其他组分
抗蚀剂组合物可以另外包含任意的添加剂,如猝灭剂、溶解调节剂、表面活性剂和炔属醇。
将猝灭剂添加至抗蚀剂组合物例如对于降低抗蚀剂膜中的酸扩散速率是有效的,因此有助于分辨率的进一步改进。合适的猝灭剂为碱性化合物,包括描述于JP-A 2008-111103第[0146]-[0164]段(USP 7,537,880)中的那些。优选伯、仲和叔胺化合物,特别是具有羟基、醚键、酯键、内酯环、氰基或磺酸酯键的胺化合物。作为猝灭剂添加的碱性化合物的适当的量按每100重量份的基础树脂计为0至100重量份,更优选0.001至50重量份。
还可使用的是JP-A 2008-239918(USP 7,598,016)中所描述的聚合物型的猝灭剂。聚合物型猝灭剂在涂覆之后在抗蚀剂表面处取向(segregate)并且因此增强了抗蚀剂图案的矩形性。当将保护膜施加在抗蚀剂膜上时,聚合物型猝灭剂还对于防止抗蚀剂图案的任何膜厚度损失或图案顶部变圆有效。当添加聚合物型猝灭剂时,只要不损害本发明的优点,其量是任意的。
由式(4)表示的在α位未氟化的磺酸的鎓盐或由式(5)表示的羧酸的鎓盐也可用作猝灭剂。
其中,R501、R502和R503各自独立地为氢、不包括氟的卤素或可以含有杂原子的C1-C40一价烃基。R501、R502和R503的任意两个可以键合在一起以与它们所连接的碳原子形成环。R504为可以含有杂原子的C1-C40一价烃基。M+为鎓阳离子。所述一价烃基可以为直链、支链或环状。
在α位未氟化的磺酸的鎓盐描述于USP 8,795,942(JP-A 2008-158339)中。能够产生在α位未氟化的磺酸的PAG示例于JP-A 2010-155824,第[0019]-[0036]段和JP-A 2010-215608第[0047]-[0082]段中。羧酸的鎓盐描述于JP 3991462中。
式(4)或(5)中的阴离子为弱酸的共轭碱。本文中所使用的弱酸表示酸度不足以使酸不稳定性基团从基础树脂中的含有酸不稳定性基团的单元中脱保护。具有式(4)或(5)的鎓盐在与具有强酸(典型地为在α位氟化的磺酸)的共轭碱作为反阴离子的鎓盐型PAG组合使用时起猝灭剂的作用。
在使用能够产生强酸(例如,α位氟化的磺酸)的鎓盐和能够产生弱酸(例如,α位非氟化的磺酸或羧酸)的鎓盐的混合物的体系中,如果在曝光于高能辐射时由PAG产生的强酸与未反应的具有弱酸阴离子的鎓盐碰撞,则发生盐交换,由此释放弱酸并且形成具有强酸阴离子的鎓盐。在该过程中,使强酸交换成具有低催化性的弱酸,引起酸的明显失活,从而能够控制酸扩散。
特别是因为α位非氟化的磺酸和羧酸的锍盐和碘鎓盐是光可降解的,所以接收高光强度的那些部分的猝灭能力降低并且在α位氟化的磺酸、亚氨酸或甲基化物酸的浓度升高。这能够形成具有在经曝光的区域中的改进的对比度的图案,进一步改进的聚焦深度(DOF)和令人满意的尺寸控制。
如果能够产生强酸的PAG为鎓盐,则可以发生从在曝光至高能辐射时产生的强酸到上述弱酸的交换,但是从不发生在曝光至高能辐射时产生的弱酸与能够产生强酸的未反应的鎓盐碰撞而诱发盐交换。这是因为鎓阳离子与较强的酸阴离子容易形成离子对。
在酸不稳定性基团为对酸非常敏感的缩醛基团的情况下,用于消除保护基的酸无需必然为α-氟化的磺酸、亚氨酸或甲基化物酸。有时甚至可以与α位非氟化的磺酸发生脱保护反应。在该情况下,因为不能将磺酸的鎓盐用作猝灭剂,所以优选将羧酸的鎓盐单独用作猝灭剂。
α位非氟化的磺酸和羧酸的鎓盐中,优选具有下式(4’)的磺酸的锍盐和具有下式(5’)的羧酸的锍盐。
其中,R551、R552和R553各自独立地为可以含有杂原子的C1-C20一价烃基。R551、R552和R553的任意两个可以键合在一起以与它们所连接的原子和介于其间的原子形成环。R554为可以含有杂原子的C1-C40一价烃基。R555和R556各自独立地为氢或三氟甲基。R557和R558各自独立地为氢、氟或三氟甲基。R559为氢、羟基、可以含有杂原子的C1-C35一价烃基或任选取代的C6-C30芳基。下标j为1至3的整数,z1、z2和z3各自独立地为0至5的整数。所述一价烃基可以为直链、支链或环状。
作为猝灭剂的鎓盐可以单独或者两种或更多种混合使用。猝灭剂的适当的量按每100重量份的基础树脂计为0至50重量份,优选0.001至50重量份,更优选0.01至20重量份。猝灭剂的包含促进了抗蚀剂感光度的调整并且抑制了抗蚀剂膜之内的酸扩散速率,导致分辨率更好。此外,其抑制了曝光之后的感光度的改变并且降低了对基底和环境的依赖性,以及改善曝光裕度和图案轮廓。猝灭剂的包含还有效改善对基底的粘合性。
将表面活性剂添加至抗蚀剂组合物有效促进或控制涂覆操作。示例性表面活性剂,描述于JP-A 2008-111103第[0165]-[0166]段中。所添加的表面活性剂的适当的量按每100重量份的基础树脂计为0至10重量份,更优选0.0001至5重量份。
将溶解调节剂添加至抗蚀剂组合物有效扩大了曝光区域和未曝光区域之间的溶解速率的差异,因此有助于分辨率的进一步改进。示例性溶解调节剂描述于USP 7,771,914(JP-A 2008-122932第[0155]-[0178]段)中。所添加的溶解调节剂的适当的量按每100重量份的基础树脂计为0至50重量份,更优选0至40重量份。
示例性炔属醇描述于JP-A 2008-122932第[0179]-[0182]段中。所添加的炔属醇的适当的量为抗蚀剂组合物的0至2重量%,更优选0.02至1重量%。
还可以添加聚合物性添加剂,以改进在旋涂时在抗蚀剂膜表面上的防水性。可以将防水性改进剂用于无面漆浸没式光刻法中。优选的防水性改进剂包括含氟代烷基的聚合物和具有拥有1,1,1,3,3,3-六氟-2-丙醇残基的特定结构的聚合物,其中它们的实例描述于JP-A 2007-297590和JP-A 2008-111103中。待添加至抗蚀剂组合物的防水性改进剂应当溶于作为显影剂的有机溶剂中。具有1,1,1,3,3,3-六氟-2-丙醇残基的特定结构的防水性改进剂良好地溶于显影剂中。以重复单元共聚的具有氨基或胺盐的聚合物可以起防水性改进剂的作用并且有效防止酸在PEB期间蒸发和在显影之后的任何孔图案开口失效。防水性改进剂的适当的量按每100重量份的基础树脂计为0.1至20重量份,优选0.5至10重量份。
如前文所述,将聚合物有利地用作抗蚀剂组合物中的基础树脂。特别是将含有所述聚合物的基础树脂与任意期望的组分包括有机溶剂、产酸剂、溶解调节剂、碱性化合物和表面活性剂组合以配制抗蚀剂组合物。该抗蚀剂组合物之所以具有非常高的感光度,在于在经曝光的区域中的聚合物在显影剂中的溶解速率通过催化反应来加速。此外,抗蚀剂膜具有高的溶解对比度、分辨率、曝光裕度和工序适应性,并且提供了在曝光之后的良好的图案轮廓、和更好的耐蚀刻性以及抑制酸扩散带来的最小的邻近偏差。凭借这些优点,组合物完全可用于商业应用并且适合作为用于制造VLSI的图案形成材料。特别是当包括产酸剂以配制能够利用酸催化的反应的化学增幅抗蚀剂组合物时,组合物具有较高的感光度并且上文描述的性质进一步得到改进。
方法
将包含含有该聚合物的基础树脂、产酸剂、有机溶剂和碱性化合物的抗蚀剂组合物,典型地化学增幅抗蚀剂组合物用于制造各种集成电路。可以通过公知的光刻法方法进行使用所述抗蚀剂组合物的图案形成。所述方法通常涉及涂覆、预烘焙、曝光和显影。如果需要,则可以增加任意另外的步骤。
首先将抗蚀剂组合物通过合适的涂覆技术如旋涂、辊涂、流动涂覆、浸涂、喷涂或刮刀涂覆施加至待在其上形成集成电路的基底(例如Si、SiO2、SiN、SiON、TiN、WSi、BPSG、SOG、有机减反射涂层)或待在其上形成掩模电路的基底(例如Cr、CrO、CrON、MoSi2、SiO2)。将涂层在热板上在60至150℃的温度预烘焙10秒至30分钟,优选在80至120℃预烘焙30秒至20分钟。所产生的抗蚀剂膜通常为0.1至2.0μm厚。
如果需要,则可以在抗蚀剂膜上形成保护膜。保护膜优选由碱性显影剂可溶性组合物形成,从而可以在显影期间实现抗蚀剂图案的形成和保护膜的剥离二者。保护膜具有如下功能:抑制抗蚀剂膜脱气,过滤或切断由EUV激光器(不是13.5nm)发射的具有140至300nm波长的谱带外(OOB)光,和防止抗蚀剂膜在环境影响下损失其厚度或呈现T形顶部轮廓。
然后直接或通过掩模将抗蚀剂膜曝光至期望图案的高能辐射如UV、深UV、EUV、EB、X射线、软X射线、准分子激光、γ射线或同步辐射。曝光剂量优选为约1至200mJ/cm2、更优选约10至100mJ/cm2或约0.1至100μC/cm2、更优选约0.5至50μC/cm2。将抗蚀剂膜在热板上优选在60至150℃进一步烘焙(PEB)10秒至30分钟,优选在80至120℃进一步烘焙(PEB)30秒至20分钟。
其后将抗蚀剂膜用含水碱溶液形式的显影剂通过常规技术如浸渍(dip)、旋覆浸没(puddle)和喷雾(spray)技术显影3秒至3分钟,优选5秒至2分钟。合适的显影剂为0.1至10wt%,优选2至5wt%的四甲基氢氧化铵(TMAH)、四乙基氢氧化铵(TEAH)、四丙基氢氧化铵(TPAH)和四丁基氢氧化铵(TBAH)的水溶液。在其中该聚合物含有重复单元(b1)和/或(b2)的实施方案中,将曝光区域中的抗蚀剂膜溶于显影剂中,而未曝光区域中的抗蚀剂膜不溶解,由此在基底上形成正型图案。在其中该聚合物含有重复单元(b3)的实施方案中,在基底上形成负型抗蚀剂图案。应理解的是,本发明的抗蚀剂组合物最佳地适合于使用高能辐射如尤其是EB、EUV、X射线、软X射线、γ射线和同步辐射的微图案化。
尽管通常将TMAH水溶液用作显影剂,但具有更长的烷基链的TEAH、TPAH和TBAH有效地抑制抗蚀剂膜在显影期间被溶胀并且因此防止图案崩溃。JP 3429592描述了将TBAH水溶液用于包含具有脂环结构的重复单元如金刚烷甲基丙烯酸酯和具有酸不稳定性基团的重复单元如甲基丙烯酸叔丁酯的聚合物显影的实例,所述聚合物由于缺乏亲水性基团而是防水的。
TMAH显影剂最经常作为2.38wt%TMAH水溶液使用,其相当于0.26N。TEAH、TPAH和TBAH水溶液应当优选具有当量浓度(equivalent normality)。相当于0.26N的TEAH、TPAH和TBAH的浓度分别为3.84wt%、5.31wt%和6.78wt%。
当通过EB和EUV光刻法解析具有32nm以下的线尺寸的图案时,产生了线变成波浪形、线融合在一起和融合的线崩溃的现象。据认为,因为线在显影剂中溶胀并且因此扩张的线融合在一起而发生该现象。因为含有液体显影剂的溶胀的线如海绵一样软,所以它们容易在冲洗的应力下崩溃。出于该原因,使用长链烷基显影试剂的显影剂有效防止膜溶胀并且因此防止图案崩溃。
在其中该聚合物含有重复单元(b1)和/或(b2)的实施方案中,可以通过有机溶剂显影由所述抗蚀剂组合物形成负型图案。用于此目的的显影剂为选自以下的至少一种溶剂:2-辛酮、2-壬酮、2-庚酮、3-庚酮、4-庚酮、2-己酮、3-己酮、二异丁基酮、甲基环己酮、苯乙酮、甲基苯乙酮、乙酸丙酯、乙酸丁酯、乙酸异丁酯、乙酸戊酯、乙酸丁烯酯、乙酸异戊酯、甲酸丙酯、甲酸丁酯、甲酸异丁酯、甲酸戊酯、甲酸异戊酯、戊酸甲酯、戊烯酸甲酯、巴豆酸甲酯、巴豆酸乙酯、丙酸甲酯、丙酸乙酯、3-乙氧基丙酸乙酯、乳酸甲酯、乳酸乙酯、乳酸丙酯、乳酸丁酯、乳酸异丁酯、乳酸戊酯、乳酸异戊酯、2-羟基异丁酸甲酯、2-羟基异丁酸乙酯、苯甲酸甲酯、苯甲酸乙酯、乙酸苯酯、乙酸苄酯、苯乙酸甲酯、甲酸苄酯、甲酸苯乙酯、3-苯基丙酸甲酯、丙酸苄酯、苯乙酸乙酯和乙酸2-苯基乙酯。
在显影结束时冲洗抗蚀剂膜。作为冲洗液优选可与显影剂混溶并且不溶解抗蚀剂膜的溶剂。合适的溶剂包括3至10个碳原子的醇,8至12个碳原子的醚化合物,6至12个碳原子的烷烃、烯烃和炔烃,和芳族溶剂。特别是,合适的3至10个碳原子的醇包括正丙醇、异丙醇、1-丁醇、2-丁醇、异丁醇、叔丁醇、1-戊醇、2-戊醇、3-戊醇、叔戊醇、新戊醇、2-甲基-1-丁醇、3-甲基-1-丁醇、3-甲基-3-戊醇、环戊醇、1-己醇、2-己醇、3-己醇、2,3-二甲基-2-丁醇、3,3-二甲基-1-丁醇、3,3-二甲基-2-丁醇、2-乙基-1-丁醇、2-甲基-1-戊醇、2-甲基-2-戊醇、2-甲基-3-戊醇、3-甲基-1-戊醇、3-甲基-2-戊醇、3-甲基-3-戊醇、4-甲基-1-戊醇、4-甲基-2-戊醇、4-甲基-3-戊醇、环己醇和1-辛醇。合适的8至12个碳原子的醚化合物包括正丁醚、异丁醚、仲丁醚、正戊醚、异戊醚、仲戊醚、叔戊醚和正己醚。合适的6至12个碳原子的烷烃包括己烷、庚烷、辛烷、壬烷、癸烷、十一烷、十二烷、甲基环戊烷、二甲基环戊烷、环己烷、甲基环己烷、二甲基环己烷、环庚烷、环辛烷和环壬烷。合适的6至12个碳原子的烯烃包括己烯、庚烯、辛烯、环己烯、甲基环己烯、二甲基环己烯、环庚烯和环辛烯。合适的6至12个碳原子的炔烃包括己炔、庚炔和辛炔。合适的芳族溶剂包括甲苯、二甲苯、乙苯、异丙苯、叔丁苯和均三甲苯。溶剂可以单独或混合使用。
实施例
在下文给出实施例和比较例用于进一步说明本发明,但不应当将它们解读为将本发明限制与此。所有份数(pbw)为按重量计。Mw相对于聚苯乙烯标样通过GPC使用THF溶剂测量。
[1]合成聚合性单体
实施例1-1
合成单体1
在氮气气氛中,将89.3g甲基三苯基溴化鏻溶于400mL的THF。在冰浴中冷却下,将28.1g粉末形式的叔丁醇钾添加至溶液。将溶液在冰浴中熟化30分钟,之后滴加37.4g反应物1在100mL的THF中的溶液。将反应溶液熟化30分钟,然后冷却,之后滴加200mL水以猝灭反应。这之后是用400mL乙酸乙酯萃取和普通含水处理(aqueous workup)。然后馏除溶剂。将残余物通过硅胶柱色谱法纯化,生成白色晶体形式的单体1(量为31.4g,收率84%)。
产物通过IR和1H-NMR光谱法分析,结果如下所示。
IR(D-ATR):ν=3403,3084,3057,3023,1834,1750,1717,1658,1623,1569,1543,1442,1414,1394,1370,1323,1303,1258,1235,1202,1126,1100,1038,1023,994,915,863,804,757,734,697,664,584,542,530cm-1
1H-NMR(600MHz,在DMSO-d6中):δ=9.64(1H,s),7.89(1H,s),7.73(1H,s),6.90(1H,dd),5.89(1H,d),5.28(1H,d)ppm
实施例1-2至1-7
合成单体2至7
下文所示的单体2至7通过与实施例1-1中相同的方法来合成,不同之处在于使用相应的反应物替代反应物1。
[2]合成聚合物
用于抗蚀剂组合物中的每种聚合物(聚合物1至19和对比聚合物1至7)通过以下制备:在环戊酮溶剂中组合单体,进行共聚反应,从己烷结晶,用己烷洗涤若干次,分离和干燥。通过1H-NMR和13C-NMR光谱法对聚合物分析组成。
实施例2-1 聚合物1
实施例2-2 聚合物2
实施例2-3 聚合物3
实施例2-4 聚合物4
实施例2-5 聚合物5
实施例2-6 聚合物6
实施例2-7 聚合物7
实施例2-8 聚合物8
实施例2-9 聚合物9
实施例2-10 聚合物10
实施例2-11 聚合物11
实施例2-12 聚合物12
实施例2-13 聚合物13
实施例2-14 聚合物14
实施例2-15 聚合物15
实施例2-16 聚合物16
实施例2-17 聚合物17
实施例2-18 聚合物18
实施例2-19 聚合物19
对比例1-1 对比聚合物1
对比例1-2 对比聚合物2
对比例1-3 对比聚合物3
对比例1-4 对比聚合物4
对比例1-5 对比聚合物5
对比例1-6 对比聚合物6
对比例1-7 对比聚合物7
[3]制备抗蚀剂组合物
通过根据表1和2中所示的配方将聚合物和其它组分溶于含有100ppm的表面活性剂FC-4430(3M)的溶剂并且通过具有0.2μm孔尺寸的过滤器过滤来制备抗蚀剂组合物。
如下标识表1和2中的组分。
有机溶剂
PGMEA:丙二醇单甲醚乙酸酯
CyH:环己酮
PGME:丙二醇单甲醚
DAA:二丙酮醇
产酸剂:
以下结构式的PAG-1至PAG-3
猝灭剂:以下结构式的猝灭剂1至3
EUV光刻法测试
实施例3-1至3-19和对比例2-1至2-7
将表1和2中的抗蚀剂组合物的每一种旋涂在具有含硅旋涂硬掩模材料SHB-A940(硅含量为43wt%,Shin-Etsu Chemical Co.,Ltd.)的20nm涂层的硅基底上并且在热板上在105℃预烘焙60秒以形成60nm厚的抗蚀剂膜。使用EUV扫描仪NXE3300(ASML,NA 0.33,σ0.9/0.6,四极照明),将抗蚀剂膜通过带有具有46nm+20%偏差的节距(晶片上尺寸)的孔图案的掩模曝光至EUV。将抗蚀剂膜在表1和2中所示的温度烘焙(PEB)60秒并且在2.38wt%TMAH水溶液中显影30秒,以形成具有23nm尺寸的孔图案。
在CD-SEM(CG-5000,Hitachi High-Technologies Corp.)下观察抗蚀剂图案。将提供具有23nm尺寸的孔图案的曝光剂量记录为感光度。测量50个孔的尺寸,由其计算尺寸改变(3σ)并且将其记录为CDU。
将抗蚀剂组合物连同EUV光刻法的CDU和感光度示于表1和2中。
表1
表2
在表1和2中证实,包含在本发明的范围内的聚合物的抗蚀剂组合物显示出高的感光度和改进的CDU。所述组合物对于光刻法微加工有效。
通过引用将日本专利申请第2017-175900号并入本文中。
尽管已对一些优选的实施方案进行了描述,但根据上述教导可对其进行许多变形和改变。因此可理解,在不脱离所附权利要求的范围的情况下可在具体描述以外实施本发明。
Claims (19)
2.根据权利要求1所述的单体,其中X1为单键。
3.根据权利要求1所述的单体,其中Rb为酸不稳定性基团。
4.根据权利要求1所述的单体,其中m为0。
7.根据权利要求5所述的聚合物,其中X1为单键。
8.根据权利要求5所述的聚合物,其中Rb为酸不稳定性基团。
9.根据权利要求5所述的聚合物,其中m为0。
10.根据权利要求5所述的聚合物,其另外包含具有能够在酸的作用下极性转换的基团的重复单元。
12.根据权利要求5所述的聚合物,其另外包含具有粘合性基团的重复单元,所述粘合性基团选自羟基、羧基、内酯环、碳酸酯、硫代碳酸酯、羰基、环状缩醛、醚键、酯键、磺酸酯键、氰基、酰胺、-O-C(=O)-S-和-O-C(=O)-NH-。
13.根据权利要求5所述的聚合物,其另外包含选自具有式(d1)、(d2)和(d3)的重复单元的至少一种类型的重复单元:
其中,RA各自独立地为氢、甲基或三氟甲基,
R11和R12各自独立地为可以含有杂原子的C1-C20一价烃基,R11和R12可以键合在一起以与它们所连接的硫原子形成环,
L1为单键、亚苯基、-C(=O)-L11-L12-或-O-L12-,L11为-O-或-NH-,L12为亚苯基或者可以含有羰基、酯键、醚键或羟基结构部分的C1-C6二价脂族烃基,
L2为单键或-L21-C(=O)-O-,L21为可以含有杂原子的C1-C20二价烃基,
L3为单键、亚甲基、亚乙基、亚苯基或氟化的亚苯基、-C(=O)-L31-L32-或-O-L32-,L31为-O-或-NH-,L32为亚苯基或可以含有羰基、酯键、醚键或羟基结构部分的C1-C6二价脂族烃基,
M-为非亲核性反离子,
其中,R13至R17各自独立地为可以含有杂原子的C1-C20一价烃基,R13、R14和R15的任意两个可以键合在一起以与它们所键合的硫原子形成环。
14.抗蚀剂组合物,其包含含有根据权利要求5所述的聚合物的基础树脂、有机溶剂和产酸剂。
15.抗蚀剂组合物,其包含含有根据权利要求13所述的聚合物的基础树脂和有机溶剂。
16.根据权利要求14所述的抗蚀剂组合物,其另外包含猝灭剂。
17.根据权利要求14所述的抗蚀剂组合物,其另外包含表面活性剂。
18.图案形成方法,其包括以下步骤:将根据权利要求14所述的抗蚀剂组合物涂覆至基底上,烘焙以形成抗蚀剂膜,将所述抗蚀剂膜曝光至高能辐射,和将经曝光的抗蚀剂膜用显影剂显影。
19.根据权利要求18所述的方法,其中所述高能辐射为i线、KrF准分子激光、ArF准分子激光、EB或波长3至15nm的EUV。
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JP6939702B2 (ja) * | 2017-06-21 | 2021-09-22 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
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CN109485590A (zh) | 2019-03-19 |
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US20190079399A1 (en) | 2019-03-14 |
US10915021B2 (en) | 2021-02-09 |
KR102125616B1 (ko) | 2020-06-22 |
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