CN1443218A - 用于光刻法的旋压玻璃抗反射涂层的吸收性化合物 - Google Patents
用于光刻法的旋压玻璃抗反射涂层的吸收性化合物 Download PDFInfo
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- CN1443218A CN1443218A CN01813009A CN01813009A CN1443218A CN 1443218 A CN1443218 A CN 1443218A CN 01813009 A CN01813009 A CN 01813009A CN 01813009 A CN01813009 A CN 01813009A CN 1443218 A CN1443218 A CN 1443218A
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- silicon
- silane
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 46
- 238000000206 photolithography Methods 0.000 title abstract description 6
- 239000006117 anti-reflective coating Substances 0.000 title abstract description 5
- 239000011521 glass Substances 0.000 title abstract description 5
- -1 acetoxysilicon compound Chemical class 0.000 claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 21
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- 239000011248 coating agent Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
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- 229910000077 silane Inorganic materials 0.000 claims description 12
- TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 claims description 11
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- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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- 239000002253 acid Substances 0.000 claims description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
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- JCJNNHDZTLRSGN-UHFFFAOYSA-N anthracen-9-ylmethanol Chemical compound C1=CC=C2C(CO)=C(C=CC=C3)C3=CC2=C1 JCJNNHDZTLRSGN-UHFFFAOYSA-N 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 4
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 4
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- 239000005055 methyl trichlorosilane Substances 0.000 claims description 3
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005049 silicon tetrachloride Substances 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- AUEJBKCWXPYRGZ-UHFFFAOYSA-N 1,1'-biphenyl diethoxysilane Chemical compound C(C)O[SiH2]OCC.C1(=CC=CC=C1)C1=CC=CC=C1 AUEJBKCWXPYRGZ-UHFFFAOYSA-N 0.000 claims description 2
- YYJNOEZFFSJVDD-UHFFFAOYSA-N 2-chloroethoxy-diethoxy-phenylsilane Chemical compound ClCCO[Si](OCC)(OCC)C1=CC=CC=C1 YYJNOEZFFSJVDD-UHFFFAOYSA-N 0.000 claims description 2
- IKBFHCBHLOZDKH-UHFFFAOYSA-N 2-chloroethyl(triethoxy)silane Chemical compound CCO[Si](CCCl)(OCC)OCC IKBFHCBHLOZDKH-UHFFFAOYSA-N 0.000 claims description 2
- CASYTJWXPQRCFF-UHFFFAOYSA-N 2-chloroethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCl CASYTJWXPQRCFF-UHFFFAOYSA-N 0.000 claims description 2
- BCSZALSGPTYQQW-UHFFFAOYSA-N O(C)[SiH](OC)OC.[Cl] Chemical compound O(C)[SiH](OC)OC.[Cl] BCSZALSGPTYQQW-UHFFFAOYSA-N 0.000 claims description 2
- IJUZIFGEBYXQJT-UHFFFAOYSA-N O(CC)[SiH](OCC)OCC.[Cl] Chemical compound O(CC)[SiH](OCC)OCC.[Cl] IJUZIFGEBYXQJT-UHFFFAOYSA-N 0.000 claims description 2
- NPVQBEIMNWDKEU-UHFFFAOYSA-N chloromethoxy-dimethoxy-phenylsilane Chemical compound ClCO[Si](OC)(OC)C1=CC=CC=C1 NPVQBEIMNWDKEU-UHFFFAOYSA-N 0.000 claims description 2
- ZDOBWJOCPDIBRZ-UHFFFAOYSA-N chloromethyl(triethoxy)silane Chemical compound CCO[Si](CCl)(OCC)OCC ZDOBWJOCPDIBRZ-UHFFFAOYSA-N 0.000 claims description 2
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- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 claims description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 claims description 2
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- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 claims description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005052 trichlorosilane Substances 0.000 claims description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 2
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- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims 2
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- 238000003756 stirring Methods 0.000 claims 1
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 10
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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Classifications
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
-
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Abstract
作为有机光吸收化合物,使用了吸收性类醚化合物,其包含通过氧键连接到萘或者蒽发色团的硅乙氧基、硅二乙氧基或者硅三乙氧基物质。该吸收性类醚化合物被引入旋压玻璃材料,为深紫外光刻法提供抗反射涂层材料。合成该光吸收醚化合物的方法基于醇取代的发色团与乙酰氧基硅化合物在醇存在下的反应。还提供了制造包含吸收性类醚化合物的吸收性旋压玻璃材料的方法。
Description
技术领域
本发明一般地涉及光吸收旋压玻璃材料,更具体地涉及可以引入旋压玻璃材料的吸收性化合物,其在光刻法中用作抗反射层,以及生产吸收性化合物的方法。
发明背景
为了满足更快性能的要求,集成电路设备部件的特征尺寸不断减小。具有较小部件尺寸的设备的制造在许多通常用于半导体制造的方法中带来了新的挑战。这些制造方法中最重要的一种是光刻法。
长期以来已经认识到,通过光刻法生产的图案中的线宽度偏差可能源于从半导体片上底层反射的光的光学干涉。由于底层的表面形态引起的光致抗蚀剂厚度的偏差同样诱导线宽度偏差。涂覆在抗光蚀剂层下的抗反射涂层(ARC)已经被用于防止来自照射光束反射的干涉。此外,抗反射涂层部分地平面化薄片的表面形态,有助于改善梯级上的线宽度偏差,因为光致抗蚀剂的厚度更均匀。
有机聚合物薄膜,尤其是在通常用于曝光抗光蚀剂的i-线(365nm)和g-线(436nm)波长和最近使用的248nm波长具有吸收的那些,通常被用作抗反射涂层。然而,有机ARC与有机抗光蚀剂共有许多化学性能的事实可能限制可用的加工程序。此外有机ARC可能与抗光蚀剂层混合。避免混合的一种解决方案是引入热固性粘结剂作为有机ARC另外的组分,例如在Flaim等的美国专利号5,693,691中描述的。染料也可以引入有机ARC,以及任选地另外的添加剂,例如润湿剂、增粘剂、防腐剂和增塑剂,如Arnold等的美国专利号4,910,122所描述的。
氮氧化硅是另一种已经用作抗反射涂层的材料。然而,氮氧化硅与ARC一样通过相消干涉方法而不是通过吸收起作用,其意味着必需非常严格控制氧氮化物厚度,并且该材料不能如ARC那样在高度变化的表面形态上起作用。此外,氮氧化硅通常通过化学蒸汽淀积进行沉积,而抗光蚀剂层通常使用旋压-涂布机涂覆。额外的化学蒸汽淀积方法增加了加工复杂性。
可以用作抗反射层的另一类材料是包含染料的旋压玻璃(SOG)组合物。Yau等美国专利号4,587,138公开了与旋压玻璃混合的染料,例如碱性黄#11,其量为大约1重量%。Allman等美国专利号5,100,503公开了交联的聚硅氧烷,其包含无机染料,例如TiO2、Cr2O7、MoO4、MnO4或者ScO4和增粘剂。Allman另外教导了也作为平面化层的旋压玻璃组合物。然而,迄今已经公开的旋压玻璃、染料混合物对于暴露于深紫外、尤其是248和193nm光源不是最佳的,而这些光源正在被普遍地用于生产具有小的部件尺寸的设备。此外,不是所有染料都可以容易地引入任意的旋压玻璃组合物中。
因此需要在深紫外光谱区中具有强烈吸收性的化合物,其可以被引入旋压玻璃组合物,以提供抗反射涂层,同时需要合成这类吸收性化合物的方法。
发明概述
用于深紫外光刻法的抗反射涂层材料包括引入旋压玻璃(SOG)材料中的一种或多种有机吸收性化合物。按照本发明的实施方案,吸收性类醚化合物,其包含通过氧键连接到萘或者蒽发色团的硅乙氧基、硅二乙氧基或者硅三乙氧基物质,被用作有机吸收性化合物。该吸收性类醚化合物具有通式C14H9(CH2)nOSiRm(OC2H5)3-m或者C10H8(CH2)nOSiRm(OC2H5)3-m,其中n=1-3,m=0-2,和R是氢或者烷基基团,例如甲基、乙基或者丙基基团。
合成本发明的光吸收类醚化合物的方法基于醇取代的发色团与乙酰氧基硅化合物在化学计量量的醇存在下的反应,该乙酰氧基硅化合物具有通式RmSi(OCOCH3)4-m其中反应物的摩尔比为1∶1∶3-m。例如,9-蒽甲氧基-甲基二乙氧基硅烷的合成使用9-蒽甲醇、甲基三乙酰氧基硅烷(MTAS)和乙醇以1∶1∶2的摩尔比作为反应物来进行。反应物与丙酮或者适合的选择性的酮混合以形成反应混合物,将其搅拌足够长时间以形成产品,然后通过惰性气体净化或者通过真空抽出除去乙酸副产品。
可以将吸收性类醚化合物引入旋压玻璃材料中,其包括甲基硅氧烷、甲基硅倍半氧烷、苯基硅氧烷、苯基硅倍半氧烷、甲基苯基硅氧烷、甲基苯基硅倍半氧烷和硅酸盐聚合物。在此,旋压玻璃材料也包括通式为(H0-1.0SiO1.5-2.0)x的氢硅氧烷聚合物,和氢硅倍半氧烷聚合物,其具有通式(HSiO1.5)x,其中x大于约8。还包括氢硅倍半氧烷和烷氧基氢化硅氧烷或者羟基氢化硅氧烷的共聚物。旋压玻璃材料还包括有机氢化硅氧烷聚合物,其通式为(H0-10SiO1.5-2.0)n(R′0-1.0SiO1.5-2.0)m,和有机氢化硅倍半氧烷聚合物,其通式为(HSiO1.5)n(R′SiO1.5)m,其中m大于0和n和m的和大于约8和R′是烷基或者芳基。引入了吸收性化合物的旋压玻璃材料的涂料溶液被用来在各种集成电路设备中的层上形成抗反射薄膜。
按照本发明的另一方面,还提供了合成吸收性旋压玻璃组合物的方法,该吸收性旋压玻璃组合物包含吸收性醚化合物。
附图描述
图1描绘了按照本发明的实施方案、用于使用甲基三乙酰氧基硅烷合成9-蒽甲氧基-甲基二乙氧基硅烷的反应流程。
详细说明
用于深紫外光刻法的抗反射涂层材料包括引入旋压玻璃(SOG)材料中的一种或多种有机吸收性化合物。吸收性旋压玻璃组合物被溶于适当的溶剂以形成涂料溶液和施加到各种在制造半器件中的材料层。吸收性旋压玻璃抗反射涂层已经被设计成能容易地应用到现有半导体制造方法中。提供应用的性能包含显影剂耐受性、在标准光致抗蚀剂工艺期间的热稳定性和相对于底层的选择脱除。
许多萘-和蒽-基化合物在248nm和低于248nm具有显著的吸收。苯-基化合物、在此相等地称作苯基-基化合物在短于200nm的波长具有显著的吸收。虽然这些萘-、蒽-和苯基-基化合物经常地被称为染料,在此使用术语吸收性化合物,因为这些化合物的吸收不局限于可见光谱区中的波长。然而,不是所有这类吸收性化合物可以被引入旋压玻璃用作ARC材料。适用于本发明的吸收性化合物,在例如248nm、193nm或者其他可以用于光刻法的紫外线波长例如365nm周围具有至少大约10nm宽波长范围的吸收峰。仅仅具有窄吸收峰,例如在这些波长周围小于2nm宽的吸收性化合物不是适合的。
适合的吸收性化合物的发色团通常具有一个、两个或者三个苯环,其可以是稠合的或者不是稠合的。可结合的吸收性化合物具有可使用的、连接到发色团的活性基团,该活性基团包括羟基基团、胺基团、羧酸基团和取代的甲硅烷基基团,其中硅键接到一个、两个或者三个“离去基团”,例如烷氧基基团或者卤素原子。乙氧基或者甲氧基基团或者氯原子常常被用作离去基团。因此,适合的活性基团包括硅乙氧基、硅二乙氧基、硅三乙氧基、硅甲氧基、硅二甲氧基、硅三甲氧基、氯代甲硅烷基、二氯代甲硅烷基和三氯代甲硅烷基基团。用于旋压玻璃组合物的结合的吸收性化合物的特定例子描述于美国专利申请序列号09/491,166,其与本申请普通转让并且在此引入作为参考。包含具有一个或多个乙氧基键接到硅的活性基团已经发现是有利的,特别是对于提高吸收性SOG薄膜的热稳定性。
按照本发明的一个方面,可结合的吸收性化合物包括作为活性基团通过氧键连接到萘或者蒽发色团的硅乙氧基、硅二乙氧基或者硅三乙氧基物质。因此,本发明的吸收性化合物是类似醚的。(如果吸收性化合物中的硅原子被碳原子替代,该化合物将被严格地分类为醚。)该化合物可以具有以下通式结构:其中,n=1-3,m=0-2,和R是氢或者烷基基团,例如甲基、乙基或者丙基基团。结构1和2举例说明其中活性基团在具体的取代基位置连接到发色团的化合物。其中活性基团连接到选择性位置的类似的化合物,其全部通过通式C14H9(CH2)nOSiRm(OC2H5)3-m或者C10H8(CH2)nOSiRm(OC2H5)3-m描述,也包括在本发明中。
合成结构1和2的光吸收类醚化合物的方法基于醇取代的稠环发色团与乙酰氧基硅化合物在醇存在下的反应。乙酰氧基硅反应物由通式RmSi(OCOCH3)4-m给出,其中R和m在以上定义。有用的乙酰氧基硅化合物的具体的例子包括甲基三乙酰氧基硅烷(MTAS)、四乙酰氧基硅烷(TAS)、二甲基二乙酰氧基硅烷和二乙基二乙酰氧基硅烷。有用的醇包括甲醇、乙醇和丙醇。
例如合成9-蒽甲氧基-甲基二乙氧基硅烷3使用摩尔比为1∶1∶2的9-蒽甲醇、MTAS和乙醇作为反应物。如可以从图1的反应机理理解的,MTAS上的一个乙酰氧基基团与9-蒽甲醇上的-CH2OH反应形成含硅活性基团的醚键和乙酸,而MTAS上的两个乙酰氧基基团与乙醇反应形成乙氧基和乙酸。在该合成法中,反应物与丙酮,或者选择性的酮例如甲基异丁基酮(MIBK)或者甲乙酮混合,形成反应混合物,其被搅拌足够长时间以形成产品3,通常几天,然后通过用惰性气体净化或者通过真空抽出除去乙酸副产品。从该反应机理可以理解,一般说来醇取代的稠环化合物与乙酰氧基硅化合物,RmSi(OCOCH3)4-m与醇的比例为1∶1∶3-m。
可以引入旋压玻璃材料中的吸收性类醚化合物包括甲基硅氧烷、甲基硅倍半氧烷、苯基硅氧烷、苯基硅倍半氧烷、甲基苯基硅氧烷、甲基苯基硅倍半氧烷和硅酸盐聚合物。在此,旋压玻璃材料也包括通式为(H0-1.0SiO1.5-2.0)x的氢硅氧烷聚合物,和氢硅倍半氧烷聚合物,其具有通式(HSiO1.5)x,其中x大于约8。还包括氢硅倍半氧烷和烷氧基氢化硅氧烷或者羟基氢化硅氧烷的共聚物。旋压玻璃材料还包括有机氢化硅氧烷聚合物,其通式为(H0-1.0SiO1.5-2.0)n(R′0-1.0SiO1.5-2.0)m,和有机氢化硅倍半氧烷聚合物,其通式为(HSiO1.5)n(R′SiO1.5)m,其中m大于0和n和m的和大于约8和R′是烷基或者芳基。某些有用的有机氢化硅氧烷聚合物的n和m的和为约8到约5000,其中R′为C1-C20烷基基团或者C6-C12芳基基团。有机氢化硅氧烷和有机氢化硅倍半氧烷聚合物是可选择地表示的旋压聚合物。特定的例子包括甲基氢化硅氧烷、乙基氢化硅氧烷、丙基氢化硅氧烷、叔丁基氢化硅氧烷、苯基氢化硅氧烷、甲基氢化硅倍半氧烷、乙基氢化硅倍半氧烷、丙基氢化硅倍半氧烷、叔丁基氢化硅倍半氧烷、苯基氢化硅倍半氧烷和其混合物。
在吸收性旋压玻璃组合物中,吸收性化合物可以填隙地引入旋压玻璃基质。可选择地,吸收性化合物化学地键接到旋压玻璃聚合物。不束缚于任何理论,本发明人建议可结合的吸收性化合物通过可使用的活性基团对旋压玻璃聚合物主链的键接提供有益结果。
旋压玻璃材料通常合成自各种硅烷反应物,包括例如三乙氧基硅烷(HTEOS)、四乙氧基硅烷(TEOS)、甲基三乙氧硅烷(MTEOS)、二甲基二乙氧基硅烷、二甲基二甲氧基硅烷、四甲氧基硅烷(TMOS)、甲基三甲氧基硅烷(MTMOS)、三甲氧基硅烷、二甲基二甲氧基硅烷、苯基三乙氧基硅烷(PTEOS)、苯基三甲氧基硅烷(PTMOS)、二苯基二乙氧基硅烷和二苯基二甲氧基硅烷。卤代硅烷,尤其是氯硅烷例如三氯硅烷、甲基三氯硅烷、乙基三氯硅烷、苯基三氯硅烷、四氯化硅、二氯甲硅烷、甲基二氯硅烷、二甲基二氯硅烷、氯三乙氧基硅烷、氯三甲氧基硅烷、氯甲基三乙氧基硅烷、氯乙基三乙氧基硅烷、氯苯基三乙氧基硅烷、氯甲基三甲氧基硅烷、氯乙基三甲氧基硅烷和氯苯基三甲氧基硅烷也被用作硅烷反应物。为了生产吸收性旋压玻璃组合物,吸收性醚化合物,例如结构(1)或者(2)或者结构(1)和/或(2)及其他吸收性化合物的混合物,在合成SOG材料期间与硅烷反应物混合。
在生产吸收性旋压玻璃组合物的一般方法中,在反应器中形成包含以下的反应混合物:硅烷反应物,例如HTEOS,或者TEOS和MTEOS,或者TMOS和MTMOS;或者,可选择地四氯化硅和甲基三氯硅烷,一种或多种吸收性化合物;溶剂或者溶剂混合物;和酸/水混合物。适当的溶剂包括丙酮、异丙醇及其他简单的醇、酮和酯例如1-丙醇、MIBK、丙氧基丙醇和乙酸丙酯。酸/水混合物是例如硝酸和水。其他质子酸或者酸酐,例如乙酸、甲酸、磷酸、盐酸或者乙酸酐可选择地被用于酸混合物。得到的混合物在约30和80℃之间的温度保持大约1到24小时以生产吸收性SOG聚合物溶液。
吸收性SOG可以用适当的溶剂稀释以获得涂料溶液,其产生各种厚度的薄膜。适合的稀释剂溶剂包括丙酮、异丙醇、乙醇、丁醇、甲醇、乙酸丙酯、乳酸乙酯、丙二醇单甲醚乙酸酯和丙二醇丙醚,商业上称为Propasol-P。高沸点的稀释剂溶剂例如乳酸乙酯和丙二醇丙醚被认为是有益的。认为高沸点溶剂降低形成泡膜缺陷的概率。与此相反,较低沸点的溶剂可以在薄膜的交联顶层下面截留和随后当在烘烤过程步骤期间除去时产生砂眼。可用于本发明的其他溶剂包括乙二醇二甲醚,可以称作甘醇二甲醚,苯甲醚、二丁醚、二丙醚和戊醇。任选地,表面活性剂例如产品FC430,由3M(Minneapolis,MN)提供,或者产品Megaface R08,由DIC(Japan)提供,也被加入到涂料溶液中。涂料溶液通常包含约0.5和20%重量之间的聚合物。在使用之前,该涂料溶液通过标准过滤技术过滤。
形成吸收性有机氢化硅氧烷材料的方法包括:形成双相溶剂的混合物,其包括非极性溶剂和极性溶剂两者和相转移催化剂;加入一种或多种有机三卤硅烷、氢化三卤硅烷和一种或多种吸收性化合物,以提供双相反应混合物;和反应该双相反应混合物1到24小时,以生产吸收性有机氢化硅氧烷聚合物。相转移催化剂包括,但是不局限于,四丁铵氯化物和苄基三甲基铵氯化物。示例性的非极性溶剂包括,但是不局限于,戊烷、己烷、庚烷、环己烷、苯、甲苯、二甲苯、卤代溶剂例如四氯化碳及其混合物。有用的极性溶剂包括水、醇和醇和水混合物。吸收性聚合物溶液如上所述被稀释和过滤以形成涂料溶液。
吸收性SOG涂料溶液被施加到各种用于半导体加工的层,取决于特定的制造方法,通常通过常规的旋压沉积技术。这些技术包括分配旋压、厚度旋压和热烘烤步骤,以生产吸收性SOG抗反射薄膜。典型工艺包括在1000和4000rpm之间持续约20秒的厚度旋压和在80℃和300℃之间的温度每个持续约1分钟的两个或三个烘烤步骤。如在以下实施例2中报告的,含有结构(3)吸收性醚的吸收性SOG抗反射薄膜具有大于0.18的消光系数。
合成9-蒽甲氧基-甲基二乙氧基硅烷3、9-蒽甲氧基-三乙氧基硅烷和包含这些吸收性化合物的吸收性SOG材料的方法描述在下面的实施例中。
实施例1
9-蒽甲氧基-甲基二乙氧基硅烷的合成
在3升烧瓶中,混合92.37克(0.419mol)甲基三乙酰氧基硅烷(MTAS)、87.36克(0.419mol)9-蒽甲醇、38.56克(0.839mol)乙醇、595.51克(10.20mol)丙酮。将该溶液在氮气氛中搅拌7天。将该溶液脱气以除去乙酸副产品。
实施例2
含9-蒽甲氧基甲基二乙氧基硅烷的吸收性SOG的合成
在1-升烧瓶中,将297克(4.798mol)异丙醇、148克(2.55gmol)丙酮、123克(0.593mol)TEOS、77克(0.432mol)MTEOS、200g的9-蒽甲氧基-甲基二乙氧基硅烷,在实施例1中生产,2.61克(0.009)mol玫红酸、10克(0.024mol)2-羟基-4(3-三乙氧基硅烷基丙氧基)-二苯基酮、0.09克(0.0004mol)2,6-二羟蒽醌、0.6克1.0M硝酸和72克(3.716mol)去离子水混合。将烧瓶回流4小时。将43克(0.590mol)丁醇加入该溶液。将所述溶液过滤。将该溶液分配,然后进行3000rpm厚度旋压20秒并在80℃和180℃分别烘烤1分钟。光学性质用N & KTechnology Model 1200分析仪测定。薄膜厚度为2801埃。在248nm,折射率(n)为1.470和消光系数(k)为0.185。
实施例3
9-蒽甲氧基-三乙氧基硅烷的合成
在3升烧瓶中,混合110.73克(0.419mol)四乙酰氧基硅烷(TAS)、87.36克(0.419mol)9-蒽甲醇、57.98克(1.2585mol)乙醇、595.51克(10.20mol)丙酮。将该溶液在氮气氛中搅拌7天。将该溶液脱气以除去乙酸副产品。
实施例4
含9-蒽甲氧基-三乙氧基硅烷的吸收性SOG的合成
在1-升烧瓶中,将297克(4.798mol)异丙醇、148克(2.558mol)丙酮、123克(0.593mol)TEOS、77克(0.432mol)MTEOS、200g的9-蒽甲氧基-三乙氧基硅烷,在实施例3中生产,0.6克1.0M硝酸和72克(3.716mol)去离子水混合。将烧瓶回流4小时。将43克(0.590mol)丁醇加入该溶液。将所述溶液过滤。
实施例5
含9-蒽甲氧基甲基二乙氧基硅烷的吸收性SOG的合成
在1-升烧瓶中,将297克(4.798mol)异丙醇、148克(2.558mol)丙酮、123克(0.593mol)TEOS、77克(0.432mol)MTEOS、200g的9-蒽甲氧基-甲基二乙氧基硅烷,在实施例1中生产,0.6克1.0M硝酸和72克(3.716mol)去离子水混合。将烧瓶回流4小时。将43克(0.590mol)丁醇加入该溶液。将所述溶液过滤。
尽管本发明已经参考具体的实施例进行了描述,该描述仅仅为本发明的实施例,不应当将其理解为限制性的。公开的实施例的各种改进和特征结合都包括在如以下权利要求所定义的发明范围内。
Claims (18)
1.制造光吸收类醚化合物的方法,该方法包括:
混合醇取代的稠合的苯环化合物,该稠环化合物包含两个或三个环,乙酰氧基硅化合物、醇和溶剂,以生产反应混合物;
搅拌该反应混合物足够的时间以形成光吸收醚化合物;和
除去酸性副产品。
2.权利要求1的方法,其中乙酰氧基硅化合物具有通式RmSi(OCOCH3)4-m其中R选自氢、甲基、乙基和丙基,和m=0-2,和其中稠环化合物、乙酰氧基硅化合物和醇以1∶1∶3-m的化学计量比混合。
3.权利要求2的方法,其中乙酰氧基硅化合物是甲基三乙酰氧基硅烷。
4.权利要求2的方法,其中稠环化合物是9-蒽甲醇。
5.权利要求2的方法,其中所述醇是乙醇。
6.权利要求3的方法,其中所述光吸收醚化合物是9-蒽甲氧基-甲基二乙氧基硅烷。
7.一种光吸收旋压玻璃组合物,其包含硅氧烷聚合物和吸收性类醚化合物,该类醚化合物包含两个或三个稠合的苯环和连接选自硅乙氧基、硅二乙氧基和硅三乙氧基的含硅物质的氧键。
8.权利要求7的组合物,其中吸收性醚化合物具有通式C14H9(CH2)nOSiRm(OC2H5)3-m或者C10H8(CH2)nOSiRm(OC2H5)3-m,其中n=1-3,m=0-2和R选自氢、甲基、乙基和丙基。
9.权利要求8的组合物,其中所述吸收性醚化合物是9-蒽甲氧基-甲基二乙氧基硅烷。
10.权利要求7的组合物,其中所述硅氧烷聚合物是选自甲基硅氧烷、甲基硅倍半氧烷、苯基硅氧烷、苯基硅倍半氧烷、甲基苯基硅氧烷、甲基苯基硅倍半氧烷和硅酸盐聚合物的聚合物。
11.权利要求7的组合物,其中所述硅氧烷聚合物是选自氢硅氧烷、氢硅倍半氧烷、有机氢化硅氧烷和有机氢化硅倍半氧烷聚合物和氢硅倍半氧烷和烷氧基氢化硅氧烷或者羟基氢化硅氧烷的共聚物的聚合物。
12.权利要求11的组合物,其中硅氧烷聚合物是具有选自以下通式的聚合物:(H0-1.0SiO1.5-2.0)x,其中x大于约8,和(H0-1.0SiO1.5-2.0)n(R′0-1.0SiO 1.5-2.0 ) m ,其中m大于0,和n和m的和为约8到约5000和R′是C1-C20烷基基团或者C6-C12芳基基团。
13.一种涂料溶液,其包含权利要求7的所述吸收性旋压玻璃组合物和溶剂或者溶剂混合物。
14.权利要求13的涂料溶液,其中所述溶液为约0.5%和约20%重量之间的吸收性旋压玻璃组合物。
15.制造吸收性旋压玻璃组合物的方法,其包括:
混合一种或多种选自烷氧基硅烷和卤代硅烷的硅烷反应物、一种或多种可结合的有机吸收性化合物,其中至少一种有机吸收性化合物是吸收性醚化合物,其包含两个或者三个稠合的苯环和连接选自硅乙氧基、硅二乙氧基和硅三乙氧基的含硅物质的氧键,酸/水混合物,和一种或多种溶剂,以形成反应混合物;和
在约30和约80℃之间的温度保持该反应混合物足够的时间,以形成吸收性旋压玻璃组合物。
16.权利要求15的方法,其中所述一种或多种硅烷反应物选自三乙氧基硅烷、四乙氧基硅烷、甲基三乙氧基硅烷、二甲基二乙氧基硅烷、二甲基二甲氧基硅烷、四甲氧基硅烷、甲基三甲氧基硅烷、三甲氧基硅烷、二甲基二甲氧基硅烷、苯基三乙氧基硅烷、苯基三甲氧基硅烷、二苯基二乙氧基硅烷,和二苯基二甲氧基硅烷、三氯硅烷、甲基三氯硅烷、乙基三氯硅烷、苯基三氯硅烷、四氯化硅、氯三乙氧基硅烷、氯三甲氧基硅烷、氯甲基三乙氧基硅烷、氯乙基三乙氧基硅烷、氯苯基三乙氧基硅烷、氯甲基三甲氧基硅烷、氯乙基三甲氧基硅烷和氯苯基三甲氧基硅烷。
17.权利要求16的方法,其中所述一种或多种硅烷反应物是四乙氧基硅烷和甲基三乙氧基硅烷。
18.权利要求15的方法,其中酸/水混合物是硝酸/水混合物。
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- 2001-07-12 JP JP2002512299A patent/JP2004504328A/ja not_active Withdrawn
- 2001-07-12 EP EP01958953A patent/EP1301569A4/en not_active Withdrawn
- 2001-07-12 AU AU2001280558A patent/AU2001280558A1/en not_active Abandoned
- 2001-07-12 WO PCT/US2001/022232 patent/WO2002006402A1/en active Application Filing
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- 2001-07-17 TW TW090117454A patent/TWI238174B/zh not_active IP Right Cessation
- 2001-08-07 TW TW093130882A patent/TW200512257A/zh unknown
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Cited By (3)
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CN102015827B (zh) * | 2008-04-28 | 2012-09-05 | 三菱瓦斯化学株式会社 | 具有紫外线吸收能力的聚碳酸酯树脂、树脂组合物、及光学材料 |
CN109722033A (zh) * | 2018-12-10 | 2019-05-07 | 沈阳化工大学 | 一种二蒽基二苯醚乙烯基硅橡胶制备方法 |
CN109722033B (zh) * | 2018-12-10 | 2021-08-06 | 沈阳化工大学 | 一种二蒽基二苯醚乙烯基硅橡胶制备方法 |
Also Published As
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CN1296435C (zh) | 2007-01-24 |
CA2413726A1 (en) | 2002-01-24 |
TW200512257A (en) | 2005-04-01 |
US6605362B2 (en) | 2003-08-12 |
WO2002006402A1 (en) | 2002-01-24 |
KR20030031120A (ko) | 2003-04-18 |
JP2004504328A (ja) | 2004-02-12 |
AU2001280558A1 (en) | 2002-01-30 |
KR100804870B1 (ko) | 2008-02-20 |
US20030199659A1 (en) | 2003-10-23 |
EP1301569A1 (en) | 2003-04-16 |
CA2413726C (en) | 2005-11-29 |
US20020068181A1 (en) | 2002-06-06 |
TWI238174B (en) | 2005-08-21 |
US6914114B2 (en) | 2005-07-05 |
US6368400B1 (en) | 2002-04-09 |
EP1301569A4 (en) | 2007-08-29 |
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