CN108291031B - 聚金属氧烷、其制造方法、其组合物、固化膜和其制造方法以及具备其的构件和电子部件 - Google Patents
聚金属氧烷、其制造方法、其组合物、固化膜和其制造方法以及具备其的构件和电子部件 Download PDFInfo
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- CN108291031B CN108291031B CN201680069004.2A CN201680069004A CN108291031B CN 108291031 B CN108291031 B CN 108291031B CN 201680069004 A CN201680069004 A CN 201680069004A CN 108291031 B CN108291031 B CN 108291031B
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- zirconium
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- -1 trihydroxysiloxy, trimethylsiloxy, triethylsiloxy, tripropylsiloxy, triisopropylsiloxy, tributylsiloxy, triisobutylsiloxy, tri-sec-butylsiloxy, tri-tert-butylsiloxy, tricyclohexylsiloxy Chemical group 0.000 claims description 124
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Images
Classifications
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- H—ELECTRICITY
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- H05B33/00—Electroluminescent light sources
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- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
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- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
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- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
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- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
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- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Abstract
Description
技术领域
本发明涉及聚金属氧烷(polymetalloxane)、其制造方法、其组合物、固化膜和其制造方法以及具备其的构件和电子部件。
背景技术
由金属氧化物形成的膜具有高耐热、高透明、高折射率等特性,在各种用途中期待具有有用的特性。
作为这样的膜的形成方法,已知通过化学的气相成长(Chemical vapordeposition;CVD)等气相法形成氧化钛、氧化锆的膜的方法等。但是,CVD等气相法中成膜速度慢,难以得到能在工业上使用的膜厚。
另一方面,提出了通过在溶剂中将金属烷氧化物水解并将其缩聚而形成聚金属氧烷,通过将其涂布、固化而得到高折射率薄膜的方法。但是,进行金属烷氧化物的水解时,水解物凝集,变得不溶于有机溶剂。因此,在溶液中以透明、均一的状态稳定地存在、且能形成均质的固化膜的聚金属氧烷现在还未实现工业化。
在过去的文献中,报告有通过将在特殊的条件下将水解十分小心地实施,来防止水解物的凝集的技术(例如参照专利文献1、2)。
现有技术文献
专利文献
专利文献1:日本特开平1−129032号公报
专利文献2: 日本特开2015−3896号公报。
发明内容
发明要解决的问题
作为在溶剂中水解金属烷氧化物的方法,专利文献1中记载的技术是将金属烷氧化物溶液的温度保持为70℃,以相对于钛烷氧化物1摩尔为1摩尔以上且1.7倍摩尔以下添加用于水解的水,由此得到可溶于有机溶剂的阶梯状的聚钛氧烷。但是,在该方法中,存在在小于70℃的温度下添加水、或者增加水的添加量时,由于水解物的凝集而发生析出的问题。此外,存在下述问题:由于水解率低,所得聚钛氧烷大量残存烷氧基,涂膜形成时因空气中的水分而发生烷氧基的水解,由于脱离而产生裂纹,不能得到均质的膜。
专利文献2中记载的技术是在特殊的盐酸盐的存在下,在醇溶液中使钛化合物与水反应而制造钛化合物低聚物的技术。但是,在该方法中,也存在下述问题:增加水的添加量时由于水解物的凝集而析出,因此不能得到高分子量的聚金属氧烷,涂膜形成时产生裂纹,不能得到均质的膜。
本发明的目的在于提供在溶液中透明、在均一的状态下稳定地存在、能形成均质的固化膜的聚金属氧烷。
解决问题的手段
本发明为具有下述通式(1)所示的构成单元的聚金属氧烷。
[化1]
(R1为有机基团,R1的至少一个为(R3 3SiO−)基。R3任选自羟基、碳原子数1〜12的烷基、碳原子数5〜12的脂环式烷基、碳原子数1〜12的烷氧基、碳原子数6〜30的芳族基、具有硅氧烷键的基团或具有金属氧烷(metalloxane)键的基团。R2任选自氢原子、碳原子数1〜12的烷基、或具有金属氧烷键的基团。R1、R2和R3存在多个时,可以各自相同,也可以不同。M表示选自Al、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Ga、Ge、Zr、Nb、Mo、Ru、Rh、Pd、Ag、In、Sn、Sb、Hf、Ta、W、Re、Os、Ir、Pt、Au、Tl和Bi中的金属原子。m为表示金属原子M的价数的整数,a为1〜(m−2)的整数)。
此外,本发明的另一方式是包括使下述通式(2)所示的化合物或其水解物缩聚的工序的聚金属氧烷的制造方法。
[化2]
(R4任选自羟基、碳原子数1〜12的烷基、碳原子数5〜12的脂环式烷基、碳原子数1〜12的烷氧基或碳原子数6〜30的芳族基。R5任选自氢原子或碳原子数1〜12的烷基。R4和R5存在多个时,可以各自相同,也可以不同。M表示选自Al、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Ga、Ge、Zr、Nb、Mo、Ru、Rh、Pd、Ag、In、Sn、Sb、Hf、Ta、W、Re、Os、Ir、Pt、Au、Tl和Bi中的金属原子。m为表示金属原子M的价数的整数,n为1〜(m−1)的整数)。
发明效果
本发明的聚金属氧烷在溶液中透明、在均一的状态下稳定地存在。此外,根据本发明的聚金属氧烷,可提供具有高透明性和高折射率的固化膜。
附图说明
[图1]示出透明导电膜图案、透明绝缘膜和配线的制作过程的示意图。
[图2]示出透明导电膜可见性评价用基板的截面的示意图。
发明实施方式
(聚金属氧烷)
本发明为具有下述通式(1)所示的构成单元的聚金属氧烷。
[化3]
R1为有机基团,R1的至少一个为(R3 3SiO−)基。R3任选自羟基、碳原子数1〜12的烷基、碳原子数5〜12的脂环式烷基、碳原子数1〜12的烷氧基、碳原子数6〜30的芳族基、具有硅氧烷键的基团或具有金属氧烷键的基团。R2任选自氢原子、碳原子数1〜12的烷基、或具有金属氧烷键的基团。R1、R2和R3存在多个时,可以各自相同,也可以不同。M表示选自Al、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Ga、Ge、Zr、Nb、Mo、Ru、Rh、Pd、Ag、In、Sn、Sb、Hf、Ta、W、Re、Os、Ir、Pt、Au、Tl和Bi中的金属原子。m为表示金属原子M的价数的整数,a为1〜(m−2)的整数。
作为R1所示的有机基团,优选羟基、碳原子数1〜12的烷基、碳原子数5〜12的脂环式烷基、碳原子数1〜12的烷氧基、碳原子数6〜30的芳族基、(R3 3SiO−)基、具有硅氧烷键的基团或具有金属氧烷键的基团。
作为碳原子数1〜12的烷基,可列举甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、2−乙基己基、壬基、癸基等。
作为碳原子数5〜12的脂环式烷基,可列举环戊基、环己基、环庚基、环辛基、环壬基、环癸基等。
作为碳原子数1〜12的烷氧基,可列举甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、戊氧基、己氧基、庚氧基、辛氧基、2−乙基己氧基、壬基、癸氧基等。
作为碳原子数6〜30的芳族基,可列举苯基、苯氧基、苄基、苯基乙基、萘基等。
具有硅氧烷键的基团是指与其它Si键合的基团。具有金属氧烷键的基团是指与其它M键合的基团。
除非另有说明,否则这些说明也在以下说明的通式(2)和通式(3)所示的金属化合物中通用。
本发明的聚金属氧烷是具有通式(1)所示的构成单元作为重复单元的物质。具有通式(1)所示的构成单元的聚金属氧烷通过具有(R3 3SiO−)基,显著提高与其它成分的相容性。因此,该聚金属氧烷在有机溶剂中稳定存在。
此外,具有通式(1)所示的构成单元的聚金属氧烷通过具有(R3 3SiO−)基,因此在后述形成固化膜的工序中,缓和了由加热带来的聚金属氧烷的缩合应力(condensationstress)。因此,通过使用该聚金属氧烷,可以得到难以发生裂纹的均质的固化膜。
作为(R3 3SiO−)基,可列举三羟基甲硅烷氧基、三甲基甲硅烷氧基、三乙基甲硅烷氧基、三丙基甲硅烷氧基、三异丙基甲硅烷氧基、三丁基甲硅烷氧基、三异丁基甲硅烷氧基、三仲丁基甲硅烷氧基、三叔丁基甲硅烷氧基、三环己基甲硅烷氧基、三甲氧基甲硅烷氧基、三乙氧基甲硅烷氧基、三丙氧基甲硅烷氧基、三异丙氧基甲硅烷氧基、三丁氧基甲硅烷氧基、三苯基甲硅烷氧基、羟基二苯基甲硅烷氧基、甲基二苯基甲硅烷氧基、乙基二苯基甲硅烷氧基、丙基二苯基甲硅烷氧基、二羟基(苯基)甲硅烷氧基、二甲基(苯基)甲硅烷氧基、二乙基(苯基)甲硅烷氧基、二丙基(苯基)甲硅烷氧基、三萘基甲硅烷氧基、羟基二萘基甲硅烷氧基、甲基二萘基甲硅烷氧基、乙基二萘基甲硅烷氧基、丙基二萘基甲硅烷氧基、二羟基(萘基)甲硅烷氧基、二甲基(萘基)甲硅烷氧基、二乙基(萘基)甲硅烷氧基、二丙基(萘基)甲硅烷氧基等。
从聚金属氧烷的耐热性的观点出发,优选R3为碳原子数1〜4的烷基、或苯基。作为碳原子数1〜4的烷基的具体例,可列举甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基。即,作为优选的(R3 3SiO−)基,可列举三甲基甲硅烷氧基、三乙基甲硅烷氧基、三丙基甲硅烷氧基、三异丙基甲硅烷氧基、三丁基甲硅烷氧基、三异丁基甲硅烷氧基、三仲丁基甲硅烷氧基、三叔丁基甲硅烷氧基、甲基二苯基甲硅烷氧基、乙基二苯基甲硅烷氧基、丙基二苯基甲硅烷氧基、二羟基(苯基)甲硅烷氧基、二甲基(苯基)甲硅烷氧基、二乙基(苯基)甲硅烷氧基、二丙基(苯基)甲硅烷氧基等。
此外,(R3 3SiO−)基的含量以Si原子的摩尔数相对于聚金属氧烷的M原子的摩尔数的比率来表示时,优选1摩尔%以上且250摩尔%以下,优选10摩尔%以上且200摩尔%以下。通过使(R3 3SiO−)基的含量为上述范围,该聚金属氧烷与其它成分的相容性进一步提高。因此,该聚金属氧烷在有机溶剂中特别稳定地存在。
优选聚金属氧烷中的R1的至少一个为羟基。具有通式(1)所示的构成单元的聚金属氧烷通过具有羟基,可成为即使在长期保管时也粘度上升小、保存稳定性优异的聚金属氧烷。
聚金属氧烷通过具有通式(1)所示的构成单元,可以形成以在主链具有电子密度高的金属原子的树脂为主体的固化膜。因此,可以使固化膜中的金属原子的密度变高,可以容易地得到高折射率。此外,聚金属氧烷通过具有通式(1)所示的构成单元,形成不具有自由电子的电介质,因此可得到高透明性和耐热性。
通式(1)中,M优选为选自Al、Ti、Zr和Sn中的金属原子。通过使用这些金属原子,可以成为具有高折射率的聚金属氧烷。进一步优选Ti或Zr。
通式(1)中,m优选3以上且5以下。
关于聚金属氧烷的重均分子量,作为下限,优选500以上,更优选1000以上,进一步优选10000以上。作为上限,优选1000000以下,更优选500000以下,进一步优选200000以下。通过使重均分子量为上述范围,涂布特性变得良好。此外,通过使重均分子量为下限值以上,可提高后述固化膜的物性,特别可得到耐裂纹性优异的固化膜。
本发明中的重均分子量是利用凝胶渗透色谱(GPC)测定的聚苯乙烯换算的值。
聚金属氧烷的重均分子量可通过例如以下的方法求出。以达到0.2wt%的方式使聚金属氧烷溶于展开溶剂,形成试样溶液。接着,将试样溶液注入填充有多孔质凝胶和展开溶剂的柱。通过差示折射率检测器检测柱溶出物,通过解析溶出时间,求出重均分子量。应予说明,作为展开溶剂,适合使用溶有氯化锂的N−甲基−2−吡咯烷酮。
(聚金属氧烷的制造方法)
具有通式(1)所示的构成单元的聚金属氧烷的合成方法没有特别限制,优选包括使下述通式(2)所示的化合物或其水解物缩聚的工序。即,本发明的另一方式是包括使下述通式(2)所示的化合物或其水解物缩聚的工序的聚金属氧烷的制造方法。
[化4]
R4任选自羟基、碳原子数1〜12的烷基、碳原子数5〜12的脂环式烷基、碳原子数1〜12的烷氧基或碳原子数6〜30的芳族基。R5任选自氢原子或碳原子数1〜12的烷基。R4和R5存在多个时,可以各自相同,也可以不同。M表示选自Al、Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Ga、Ge、Zr、Nb、Mo、Ru、Rh、Pd、Ag、In、Sn、Sb、Hf、Ta、W、Re、Os、Ir、Pt、Au、Tl和Bi中的金属原子。m为表示金属原子M的价数的整数,n为1〜(m−1)的整数。
更具体而言,优选:根据需要使通式(2)所示的化合物进行水解,然后,进行部分缩合和聚合,由此合成。在此,部分缩合是指不使水解物的M−OH完全缩合、所得聚金属氧烷残存一部分M−OH。在后述一般的缩合条件下,一般地M−OH部分地残存。残存的M−OH量没有限制。
一般地,向金属烷氧化物添加水时,烷氧基的水解性高,生成分子中的全部烷氧基被水解了的氢氧化金属化合物。该氢氧化金属化合物在溶液中凝集且变得不溶于溶剂,因此发生析出。
另一方面,通式(2)所示的化合物由于(R3 3SiO−)所示的甲硅烷氧基的水解性低,因此,通过水的添加,可选择性地使烷氧基水解。所得水解物由于甲硅烷氧基的立体障碍而不在溶液中凝集,可得到透明且均一的溶液。因此,与以往的技术相比,可提高水解率。因此,通过使通式(2)所示的化合物水解并缩聚,可得到高分子量的聚金属氧烷、特别是重均分子量超过10000的聚金属氧烷。
作为通式(2)所示的化合物的具体例,例如金属原子M为Ti时,作为n=1的化合物,可列举
三甲氧基(三甲基甲硅烷氧基)钛、三乙氧基(三甲基甲硅烷氧基)钛、三丙氧基(三甲基甲硅烷氧基)钛、三异丙氧基(三甲基甲硅烷氧基)钛、三丁氧基(三甲基甲硅烷氧基)钛、三异丁氧基(三甲基甲硅烷氧基)钛、三仲丁氧基(三甲基甲硅烷氧基)钛、三叔丁氧基(三甲基甲硅烷氧基)钛、三环己氧基(三甲基甲硅烷氧基)钛、三苯氧基(三甲基甲硅烷氧基)钛;
三甲氧基(三乙基甲硅烷氧基)钛、三乙氧基(三乙基甲硅烷氧基)钛、三丙氧基(三乙基甲硅烷氧基)钛、三异丙氧基(三乙基甲硅烷氧基)钛、三丁氧基(三乙基甲硅烷氧基)钛、三异丁氧基(三乙基甲硅烷氧基)钛、三仲丁氧基(三乙基甲硅烷氧基)钛、三叔丁氧基(三乙基甲硅烷氧基)钛、三环己氧基(三乙基甲硅烷氧基)钛、三苯氧基(三乙基甲硅烷氧基)钛;
三甲氧基(三丙基甲硅烷氧基)钛、三乙氧基(三丙基甲硅烷氧基)钛、三丙氧基(三丙基甲硅烷氧基)钛、三异丙氧基(三丙基甲硅烷氧基)钛、三丁氧基(三丙基甲硅烷氧基)钛、三异丁氧基(三丙基甲硅烷氧基)钛、三仲丁氧基(三丙基甲硅烷氧基)钛、三叔丁氧基(三丙基甲硅烷氧基)钛、三环己氧基(三丙基甲硅烷氧基)钛、三苯氧基(三丙基甲硅烷氧基)钛;
三甲氧基(三异丙基甲硅烷氧基)钛、三乙氧基(三异丙基甲硅烷氧基)钛、三丙氧基(三异丙基甲硅烷氧基)钛、三异丙氧基(三异丙基甲硅烷氧基)钛、三丁氧基(三异丙基甲硅烷氧基)钛、三异丁氧基(三异丙基甲硅烷氧基)钛、三仲丁氧基(三异丙基甲硅烷氧基)钛、三叔丁氧基(三异丙基甲硅烷氧基)钛、三环己氧基(三异丙基甲硅烷氧基)钛、三苯氧基(三异丙基甲硅烷氧基)钛;
三甲氧基(三丁基甲硅烷氧基)钛、三乙氧基(三丁基甲硅烷氧基)钛、三丙氧基(三丁基甲硅烷氧基)钛、三异丙氧基(三丁基甲硅烷氧基)钛、三丁氧基(三丁基甲硅烷氧基)钛、三异丁氧基(三丁基甲硅烷氧基)钛、三仲丁氧基(三丁基甲硅烷氧基)钛、三叔丁氧基(三丁基甲硅烷氧基)钛、三环己氧基(三丁基甲硅烷氧基)钛、三苯氧基(三丁基甲硅烷氧基)钛;
三甲氧基(三异丁基甲硅烷氧基)钛、三乙氧基(三异丁基甲硅烷氧基)钛、三丙氧基(三异丁基甲硅烷氧基)钛、三异丙氧基(三异丁基甲硅烷氧基)钛、三丁氧基(三异丁基甲硅烷氧基)钛、三异丁氧基(三异丁基甲硅烷氧基)钛、三仲丁氧基(三异丁基甲硅烷氧基)钛、三叔丁氧基(三异丁基甲硅烷氧基)钛、三环己氧基(三异丁基甲硅烷氧基)钛、三苯氧基(三异丁基甲硅烷氧基)钛;
三甲氧基(三仲丁氧基甲硅烷氧基)钛、三乙氧基(三仲丁氧基甲硅烷氧基)钛、三丙氧基(三仲丁氧基甲硅烷氧基)钛、三异丙氧基(三仲丁氧基甲硅烷氧基)钛、三丁氧基(三仲丁氧基甲硅烷氧基)钛、三异丁氧基(三仲丁氧基甲硅烷氧基)钛、三仲丁氧基(三仲丁氧基甲硅烷氧基)钛、三叔丁氧基(三仲丁氧基甲硅烷氧基)钛、三环己氧基(三仲丁氧基甲硅烷氧基)钛、三苯氧基(三仲丁氧基甲硅烷氧基)钛;
三甲氧基(三叔丁氧基甲硅烷氧基)钛、三乙氧基(三叔丁氧基甲硅烷氧基)钛、三丙氧基(三叔丁氧基甲硅烷氧基)钛、三异丙氧基(三叔丁氧基甲硅烷氧基)钛、三丁氧基(三叔丁氧基甲硅烷氧基)钛、三异丁氧基(三叔丁氧基甲硅烷氧基)钛、三仲丁氧基(三叔丁氧基甲硅烷氧基)钛、三叔丁氧基(三叔丁氧基甲硅烷氧基)钛、三环己氧基(三叔丁氧基甲硅烷氧基)钛、三苯氧基(三叔丁氧基甲硅烷氧基)钛;
三甲氧基(三环己基甲硅烷氧基)钛、三乙氧基(三环己基甲硅烷氧基)钛、三丙氧基(三环己基甲硅烷氧基)钛、三异丙氧基(三环己基甲硅烷氧基)钛、三丁氧基(三环己基甲硅烷氧基)钛、三异丁氧基(三环己基甲硅烷氧基)钛、三仲丁氧基(三环己基甲硅烷氧基)钛、三叔丁氧基(三环己基甲硅烷氧基)钛、三环己氧基(三环己基甲硅烷氧基)钛、三苯氧基(三环己基甲硅烷氧基)钛;
三甲氧基(三苯基甲硅烷氧基)钛、三乙氧基(三苯基甲硅烷氧基)钛、三丙氧基(三苯基甲硅烷氧基)钛、三异丙氧基(三苯基甲硅烷氧基)钛、三丁氧基(三苯基甲硅烷氧基)钛、三异丁氧基(三苯基甲硅烷氧基)钛、三仲丁氧基(三苯基甲硅烷氧基)钛、三叔丁氧基(三苯基甲硅烷氧基)钛、三环己氧基(三苯基甲硅烷氧基)钛、三苯氧基(三苯基甲硅烷氧基)钛;
等,作为n=2的化合物,可列举
二甲氧基双(三甲基甲硅烷氧基)钛、二乙氧基双(三甲基甲硅烷氧基)钛、二丙氧基双(三甲基甲硅烷氧基)钛、二异丙氧基双(三甲基甲硅烷氧基)钛、二丁氧基双(三甲基甲硅烷氧基)钛、二异丁氧基双(三甲基甲硅烷氧基)钛、二仲丁氧基双(三甲基甲硅烷氧基)钛、二叔丁氧基双(三甲基甲硅烷氧基)钛、二环己氧基双(三甲基甲硅烷氧基)钛、二苯氧基双(三甲基甲硅烷氧基)钛;
二甲氧基双(三乙基甲硅烷氧基)钛、二乙氧基双(三乙基甲硅烷氧基)钛、二丙氧基双(三乙基甲硅烷氧基)钛、二异丙氧基双(三乙基甲硅烷氧基)钛、二丁氧基双(三乙基甲硅烷氧基)钛、二异丁氧基双(三乙基甲硅烷氧基)钛、二仲丁氧基双(三乙基甲硅烷氧基)钛、二叔丁氧基双(三乙基甲硅烷氧基)钛、二环己氧基双(三乙基甲硅烷氧基)钛、二苯氧基双(三乙基甲硅烷氧基)钛;
二甲氧基双(三丙基甲硅烷氧基)钛、二乙氧基双(三丙基甲硅烷氧基)钛、二丙氧基双(三丙基甲硅烷氧基)钛、二异丙氧基双(三丙基甲硅烷氧基)钛、二丁氧基双(三丙基甲硅烷氧基)钛、二异丁氧基双(三丙基甲硅烷氧基)钛、二仲丁氧基双(三丙基甲硅烷氧基)钛、二叔丁氧基双(三丙基甲硅烷氧基)钛、二环己氧基双(三丙基甲硅烷氧基)钛、二苯氧基双(三丙基甲硅烷氧基)钛;
二甲氧基双(三异丙基甲硅烷氧基)钛、二乙氧基双(三异丙基甲硅烷氧基)钛、二丙氧基双(三异丙基甲硅烷氧基)钛、二异丙氧基双(三异丙基甲硅烷氧基)钛、二丁氧基双(三异丙基甲硅烷氧基)钛、二异丁氧基双(三异丙基甲硅烷氧基)钛、二仲丁氧基双(三异丙基甲硅烷氧基)钛、二叔丁氧基双(三异丙基甲硅烷氧基)钛、二环己氧基双(三异丙基甲硅烷氧基)钛、二苯氧基双(三异丙基甲硅烷氧基)钛;
二甲氧基双(三丁基甲硅烷氧基)钛、二乙氧基双(三丁基甲硅烷氧基)钛、二丙氧基双(三丁基甲硅烷氧基)钛、二异丙氧基双(三丁基甲硅烷氧基)钛、二丁氧基双(三丁基甲硅烷氧基)钛、二异丁氧基双(三丁基甲硅烷氧基)钛、二仲丁氧基双(三丁基甲硅烷氧基)钛、二叔丁氧基双(三丁基甲硅烷氧基)钛、二环己氧基双(三丁基甲硅烷氧基)钛、二苯氧基双(三丁基甲硅烷氧基)钛;
二甲氧基双(三异丁基甲硅烷氧基)钛、二乙氧基双(三异丁基甲硅烷氧基)钛、二丙氧基双(三异丁基甲硅烷氧基)钛、二异丙氧基双(三异丁基甲硅烷氧基)钛、二丁氧基双(三异丁基甲硅烷氧基)钛、二异丁氧基双(三异丁基甲硅烷氧基)钛、二仲丁氧基双(三异丁基甲硅烷氧基)钛、二叔丁氧基双(三异丁基甲硅烷氧基)钛、二环己氧基双(三异丁基甲硅烷氧基)钛、二苯氧基双(三异丁基甲硅烷氧基)钛;
二甲氧基双(三仲丁氧基甲硅烷氧基)钛、二乙氧基双(三仲丁氧基甲硅烷氧基)钛、二丙氧基双(三仲丁氧基甲硅烷氧基)钛、二异丙氧基双(三仲丁氧基甲硅烷氧基)钛、二丁氧基双(三仲丁氧基甲硅烷氧基)钛、二异丁氧基双(三仲丁氧基甲硅烷氧基)钛、二仲丁氧基双(三仲丁氧基甲硅烷氧基)钛、二叔丁氧基双(三仲丁氧基甲硅烷氧基)钛、二环己氧基双(三仲丁氧基甲硅烷氧基)钛、二苯氧基双(三仲丁氧基甲硅烷氧基)钛;
二甲氧基双(三叔丁氧基甲硅烷氧基)钛、二乙氧基双(三叔丁氧基甲硅烷氧基)钛、二丙氧基双(三叔丁氧基甲硅烷氧基)钛、二异丙氧基双(三叔丁氧基甲硅烷氧基)钛、二丁氧基双(三叔丁氧基甲硅烷氧基)钛、二异丁氧基双(三叔丁氧基甲硅烷氧基)钛、二仲丁氧基双(三叔丁氧基甲硅烷氧基)钛、二叔丁氧基双(三叔丁氧基甲硅烷氧基)钛、二环己氧基双(三叔丁氧基甲硅烷氧基)钛、二苯氧基双(三叔丁氧基甲硅烷氧基)钛;
二甲氧基双(三环己基甲硅烷氧基)钛、二乙氧基双(三环己基甲硅烷氧基)钛、二丙氧基双(三环己基甲硅烷氧基)钛、二异丙氧基双(三环己基甲硅烷氧基)钛、二丁氧基双(三环己基甲硅烷氧基)钛、二异丁氧基双(三环己基甲硅烷氧基)钛、二仲丁氧基双(三环己基甲硅烷氧基)钛、二叔丁氧基双(三环己基甲硅烷氧基)钛、二环己氧基双(三环己基甲硅烷氧基)钛、二苯氧基双(三环己基甲硅烷氧基)钛;
二甲氧基双(三苯基甲硅烷氧基)钛、二乙氧基双(三苯基甲硅烷氧基)钛、二丙氧基双(三苯基甲硅烷氧基)钛、二异丙氧基双(三苯基甲硅烷氧基)钛、二丁氧基双(三苯基甲硅烷氧基)钛、二异丁氧基双(三苯基甲硅烷氧基)钛、二仲丁氧基双(三苯基甲硅烷氧基)钛、二叔丁氧基双(三苯基甲硅烷氧基)钛、二环己氧基双(三苯基甲硅烷氧基)钛、二苯氧基双(三苯基甲硅烷氧基)钛;
等。
金属原子M为Zr时,作为n=1的化合物,可列举
三甲氧基(三甲基甲硅烷氧基)锆、三乙氧基(三甲基甲硅烷氧基)锆、三丙氧基(三甲基甲硅烷氧基)锆、三异丙氧基(三甲基甲硅烷氧基)锆、三丁氧基(三甲基甲硅烷氧基)锆、三异丁氧基(三甲基甲硅烷氧基)锆、三仲丁氧基(三甲基甲硅烷氧基)锆、三叔丁氧基(三甲基甲硅烷氧基)锆、三环己氧基(三甲基甲硅烷氧基)锆、三苯氧基(三甲基甲硅烷氧基)锆;
三甲氧基(三乙基甲硅烷氧基)锆、三乙氧基(三乙基甲硅烷氧基)锆、三丙氧基(三乙基甲硅烷氧基)锆、三异丙氧基(三乙基甲硅烷氧基)锆、三丁氧基(三乙基甲硅烷氧基)锆、三异丁氧基(三乙基甲硅烷氧基)锆、三仲丁氧基(三乙基甲硅烷氧基)锆、三叔丁氧基(三乙基甲硅烷氧基)锆、三环己氧基(三乙基甲硅烷氧基)锆、三苯氧基(三乙基甲硅烷氧基)锆;
三甲氧基(三丙基甲硅烷氧基)锆、三乙氧基(三丙基甲硅烷氧基)锆、三丙氧基(三丙基甲硅烷氧基)锆、三异丙氧基(三丙基甲硅烷氧基)锆、三丁氧基(三丙基甲硅烷氧基)锆、三异丁氧基(三丙基甲硅烷氧基)锆、三仲丁氧基(三丙基甲硅烷氧基)锆、三叔丁氧基(三丙基甲硅烷氧基)锆、三环己氧基(三丙基甲硅烷氧基)锆、三苯氧基(三丙基甲硅烷氧基)锆;
三甲氧基(三异丙基甲硅烷氧基)锆、三乙氧基(三异丙基甲硅烷氧基)锆、三丙氧基(三异丙基甲硅烷氧基)锆、三异丙氧基(三异丙基甲硅烷氧基)锆、三丁氧基(三异丙基甲硅烷氧基)锆、三异丁氧基(三异丙基甲硅烷氧基)锆、三仲丁氧基(三异丙基甲硅烷氧基)锆、三叔丁氧基(三异丙基甲硅烷氧基)锆、三环己氧基(三异丙基甲硅烷氧基)锆、三苯氧基(三异丙基甲硅烷氧基)锆;
三甲氧基(三丁基甲硅烷氧基)锆、三乙氧基(三丁基甲硅烷氧基)锆、三丙氧基(三丁基甲硅烷氧基)锆、三异丙氧基(三丁基甲硅烷氧基)锆、三丁氧基(三丁基甲硅烷氧基)锆、三异丁氧基(三丁基甲硅烷氧基)锆、三仲丁氧基(三丁基甲硅烷氧基)锆、三叔丁氧基(三丁基甲硅烷氧基)锆、三环己氧基(三丁基甲硅烷氧基)锆、三苯氧基(三丁基甲硅烷氧基)锆;
三甲氧基(三异丁基甲硅烷氧基)锆、三乙氧基(三异丁基甲硅烷氧基)锆、三丙氧基(三异丁基甲硅烷氧基)锆、三异丙氧基(三异丁基甲硅烷氧基)锆、三丁氧基(三异丁基甲硅烷氧基)锆、三异丁氧基(三异丁基甲硅烷氧基)锆、三仲丁氧基(三异丁基甲硅烷氧基)锆、三叔丁氧基(三异丁基甲硅烷氧基)锆、三环己氧基(三异丁基甲硅烷氧基)锆、三苯氧基(三异丁基甲硅烷氧基)锆;
三甲氧基(三仲丁氧基甲硅烷氧基)锆、三乙氧基(三仲丁氧基甲硅烷氧基)锆、三丙氧基(三仲丁氧基甲硅烷氧基)锆、三异丙氧基(三仲丁氧基甲硅烷氧基)锆、三−正丁氧基(三仲丁氧基甲硅烷氧基)锆、三异丁氧基(三仲丁氧基甲硅烷氧基)锆、三仲丁氧基(三仲丁氧基甲硅烷氧基)锆、三叔丁氧基(三仲丁氧基甲硅烷氧基)锆、三环己氧基(三仲丁氧基甲硅烷氧基)锆、三苯氧基(三仲丁氧基甲硅烷氧基)锆;
三甲氧基(三叔丁氧基甲硅烷氧基)锆、三乙氧基(三叔丁氧基甲硅烷氧基)锆、三丙氧基(三叔丁氧基甲硅烷氧基)锆、三异丙氧基(三叔丁氧基甲硅烷氧基)锆、三−正丁氧基(三叔丁氧基甲硅烷氧基)锆、三异丁氧基(三叔丁氧基甲硅烷氧基)锆、三仲丁氧基(三叔丁氧基甲硅烷氧基)锆、三叔丁氧基(三叔丁氧基甲硅烷氧基)锆、三环己氧基(三叔丁氧基甲硅烷氧基)锆、三苯氧基(三叔丁氧基甲硅烷氧基)锆;
三甲氧基(三环己基甲硅烷氧基)锆、三乙氧基(三环己基甲硅烷氧基)锆、三丙氧基(三环己基甲硅烷氧基)锆、三异丙氧基(三环己基甲硅烷氧基)锆、三丁氧基(三环己基甲硅烷氧基)锆、三异丁氧基(三环己基甲硅烷氧基)锆、三仲丁氧基(三环己基甲硅烷氧基)锆、三叔丁氧基(三环己基甲硅烷氧基)锆、三环己氧基(三环己基甲硅烷氧基)锆、三苯氧基(三环己基甲硅烷氧基)锆;
三甲氧基(三苯基甲硅烷氧基)锆、三乙氧基(三苯基甲硅烷氧基)锆、三丙氧基(三苯基甲硅烷氧基)锆、三异丙氧基(三苯基甲硅烷氧基)锆、三丁氧基(三苯基甲硅烷氧基)锆、三异丁氧基(三苯基甲硅烷氧基)锆、三仲丁氧基(三苯基甲硅烷氧基)锆、三叔丁氧基(三苯基甲硅烷氧基)锆、三环己氧基(三苯基甲硅烷氧基)锆、三苯氧基(三苯基甲硅烷氧基)锆;等,
作为n=2的化合物,可列举
二甲氧基双(三甲基甲硅烷氧基)锆、二乙氧基双(三甲基甲硅烷氧基)锆、二丙氧基双(三甲基甲硅烷氧基)锆、二异丙氧基双(三甲基甲硅烷氧基)锆、二丁氧基双(三甲基甲硅烷氧基)锆、二异丁氧基双(三甲基甲硅烷氧基)锆、二仲丁氧基双(三甲基甲硅烷氧基)锆、二叔丁氧基双(三甲基甲硅烷氧基)锆、二环己氧基双(三甲基甲硅烷氧基)锆、二苯氧基双(三甲基甲硅烷氧基)锆;
二甲氧基双(三乙基甲硅烷氧基)锆、二乙氧基双(三乙基甲硅烷氧基)锆、二丙氧基双(三乙基甲硅烷氧基)锆、二异丙氧基双(三乙基甲硅烷氧基)锆、二丁氧基双(三乙基甲硅烷氧基)锆、二异丁氧基双(三乙基甲硅烷氧基)锆、二仲丁氧基双(三乙基甲硅烷氧基)锆、二叔丁氧基双(三乙基甲硅烷氧基)锆、二环己氧基双(三乙基甲硅烷氧基)锆、二苯氧基双(三乙基甲硅烷氧基)锆;
二甲氧基双(三丙基甲硅烷氧基)锆、二乙氧基双(三丙基甲硅烷氧基)锆、二丙氧基双(三丙基甲硅烷氧基)锆、二异丙氧基双(三丙基甲硅烷氧基)锆、二丁氧基双(三丙基甲硅烷氧基)锆、二异丁氧基双(三丙基甲硅烷氧基)锆、二仲丁氧基双(三丙基甲硅烷氧基)锆、二叔丁氧基双(三丙基甲硅烷氧基)锆、二环己氧基双(三丙基甲硅烷氧基)锆、二苯氧基双(三丙基甲硅烷氧基)锆;
二甲氧基双(三异丙基甲硅烷氧基)锆、二乙氧基双(三异丙基甲硅烷氧基)锆、二丙氧基双(三异丙基甲硅烷氧基)锆、二异丙氧基双(三异丙基甲硅烷氧基)锆、二丁氧基双(三异丙基甲硅烷氧基)锆、二异丁氧基双(三异丙基甲硅烷氧基)锆、二仲丁氧基双(三异丙基甲硅烷氧基)锆、二叔丁氧基双(三异丙基甲硅烷氧基)锆、二环己氧基双(三异丙基甲硅烷氧基)锆、二苯氧基双(三异丙基甲硅烷氧基)锆;
二甲氧基双(三丁基甲硅烷氧基)锆、二乙氧基双(三丁基甲硅烷氧基)锆、二丙氧基双(三丁基甲硅烷氧基)锆、二异丙氧基双(三丁基甲硅烷氧基)锆、二丁氧基双(三丁基甲硅烷氧基)锆、二异丁氧基双(三丁基甲硅烷氧基)锆、二仲丁氧基双(三丁基甲硅烷氧基)锆、二叔丁氧基双(三丁基甲硅烷氧基)锆、二环己氧基双(三丁基甲硅烷氧基)锆、二苯氧基双(三丁基甲硅烷氧基)锆;
二甲氧基双(三异丁基甲硅烷氧基)锆、二乙氧基双(三异丁基甲硅烷氧基)锆、二丙氧基双(三异丁基甲硅烷氧基)锆、二异丙氧基双(三异丁基甲硅烷氧基)锆、二丁氧基双(三异丁基甲硅烷氧基)锆、二异丁氧基双(三异丁基甲硅烷氧基)锆、二仲丁氧基双(三异丁基甲硅烷氧基)锆、二叔丁氧基双(三异丁基甲硅烷氧基)锆、二环己氧基双(三异丁基甲硅烷氧基)锆、二苯氧基双(三异丁基甲硅烷氧基)锆;
二甲氧基双(三仲丁氧基甲硅烷氧基)锆、二乙氧基双(三仲丁氧基甲硅烷氧基)锆、二丙氧基双(三仲丁氧基甲硅烷氧基)锆、二异丙氧基双(三仲丁氧基甲硅烷氧基)锆、二丁氧基双(三仲丁氧基甲硅烷氧基)锆、二异丁氧基双(三仲丁氧基甲硅烷氧基)锆、二仲丁氧基双(三仲丁氧基甲硅烷氧基)锆、二叔丁氧基双(三仲丁氧基甲硅烷氧基)锆、二环己氧基双(三仲丁氧基甲硅烷氧基)锆、二苯氧基双(三仲丁氧基甲硅烷氧基)锆;
二甲氧基双(三叔丁氧基甲硅烷氧基)锆、二乙氧基双(三叔丁氧基甲硅烷氧基)锆、二丙氧基双(三叔丁氧基甲硅烷氧基)锆、二异丙氧基双(三叔丁氧基甲硅烷氧基)锆、二丁氧基双(三叔丁氧基甲硅烷氧基)锆、二异丁氧基双(三叔丁氧基甲硅烷氧基)锆、二仲丁氧基双(三叔丁氧基甲硅烷氧基)锆、二叔丁氧基双(三叔丁氧基甲硅烷氧基)锆、二环己氧基双(三叔丁氧基甲硅烷氧基)锆、二苯氧基双(三叔丁氧基甲硅烷氧基)锆;
二甲氧基双(三环己基甲硅烷氧基)锆、二乙氧基双(三环己基甲硅烷氧基)锆、二丙氧基双(三环己基甲硅烷氧基)锆、二异丙氧基双(三环己基甲硅烷氧基)锆、二−正丁氧基双(三环己基甲硅烷氧基)锆、二异丁氧基双(三环己基甲硅烷氧基)锆、二仲丁氧基双(三环己基甲硅烷氧基)锆、二叔丁氧基双(三环己基甲硅烷氧基)锆、二环己氧基双(三环己基甲硅烷氧基)锆、二苯氧基双(三环己基甲硅烷氧基)锆;
二甲氧基双(三苯基甲硅烷氧基)锆、二乙氧基双(三苯基甲硅烷氧基)锆、二丙氧基双(三苯基甲硅烷氧基)锆、二异丙氧基双(三苯基甲硅烷氧基)锆、二丁氧基双(三苯基甲硅烷氧基)锆、二异丁氧基双(三苯基甲硅烷氧基)锆、二仲丁氧基双(三苯基甲硅烷氧基)锆、二叔丁氧基双(三苯基甲硅烷氧基)锆、二环己氧基双(三苯基甲硅烷氧基)锆、二苯氧基双(三苯基甲硅烷氧基)锆;
等。
具有通式(1)所示的构成单元的聚金属氧烷的合成方法中,特别优选包括根据需要使通式(2)中R5的至少1个为氢原子的化合物进行水解而缩聚的工序。即,优选通式(2)所示的化合物为下述通式(3)所示的化合物。
[化5]
R6与通式(1)中的R4相同,R7为碳原子数1〜12的烷基。m为表示金属原子M的价数的整数,x为1〜(m−1)的整数,y为1〜(m−1)的整数,x+y≦m。
应予说明,y优选为2〜(m−1)的整数。
一般地,具有羟基的化合物因羟基的氢键而凝集,变得不溶于有机溶剂,通式(3)所示的金属化合物通过具有甲硅烷氧基,由于甲硅烷氧基的立体障碍而在有机溶剂中不发生凝集,可提供透明且均一的溶液。此外,羟基可发生脱水缩合,因此可通过使通式(3)所示的金属化合物发生缩聚而得到高分子量的聚金属氧烷。此外,甲硅烷氧基的耐热性高,因此可形成透明性优异的高分子量的聚金属氧烷。
应予说明,OR7存在时,优选在缩聚之前进行该水解。通式(3)所示的化合物的水解物与通式(2)所示的化合物的情况相同,由于甲硅烷氧基的立体障碍而不在溶液中凝集,可得到透明且均一的溶液。因此,与以往的技术相比,可提高水解率。
作为通式(3)所示的金属化合物,例如金属原子M为Ti时,作为y=2的化合物,可列举
甲氧基二羟基(三甲基甲硅烷氧基)钛、乙氧基二羟基(三甲基甲硅烷氧基)钛、丙氧基二羟基(三甲基甲硅烷氧基)钛、异丙氧基二羟基(三甲基甲硅烷氧基)钛、丁氧基二羟基(三甲基甲硅烷氧基)钛、异丁氧基二羟基(三甲基甲硅烷氧基)钛、仲丁氧基二羟基(三甲基甲硅烷氧基)钛、叔丁氧基二羟基(三甲基甲硅烷氧基)钛、环己氧基二羟基(三甲基甲硅烷氧基)钛、苯氧基二羟基(三甲基甲硅烷氧基)钛;
甲氧基二羟基(三乙基甲硅烷氧基)钛、乙氧基二羟基(三乙基甲硅烷氧基)钛、丙氧基二羟基(三乙基甲硅烷氧基)钛、异丙氧基二羟基(三乙基甲硅烷氧基)钛、丁氧基二羟基(三乙基甲硅烷氧基)钛、异丁氧基二羟基(三乙基甲硅烷氧基)钛、仲丁氧基二羟基(三乙基甲硅烷氧基)钛、叔丁氧基二羟基(三乙基甲硅烷氧基)钛、环己氧基二羟基(三乙基甲硅烷氧基)钛、苯氧基二羟基(三乙基甲硅烷氧基)钛;
甲氧基二羟基(三丙基甲硅烷氧基)钛、乙氧基二羟基(三丙基甲硅烷氧基)钛、丙氧基二羟基(三丙基甲硅烷氧基)钛、异丙氧基二羟基(三丙基甲硅烷氧基)钛、丁氧基二羟基(三丙基甲硅烷氧基)钛、异丁氧基二羟基(三丙基甲硅烷氧基)钛、仲丁氧基二羟基(三丙基甲硅烷氧基)钛、叔丁氧基二羟基(三丙基甲硅烷氧基)钛、环己氧基二羟基(三丙基甲硅烷氧基)钛、苯氧基二羟基(三丙基甲硅烷氧基)钛;
甲氧基二羟基(三异丙基甲硅烷氧基)钛、乙氧基二羟基(三异丙基甲硅烷氧基)钛、丙氧基二羟基(三异丙基甲硅烷氧基)钛、异丙氧基二羟基(三异丙基甲硅烷氧基)钛、丁氧基二羟基(三异丙基甲硅烷氧基)钛、异丁氧基二羟基(三异丙基甲硅烷氧基)钛、仲丁氧基二羟基(三异丙基甲硅烷氧基)钛、叔丁氧基二羟基(三异丙基甲硅烷氧基)钛、环己氧基二羟基(三异丙基甲硅烷氧基)钛、苯氧基二羟基(三异丙基甲硅烷氧基)钛;
甲氧基二羟基(三丁基甲硅烷氧基)钛、乙氧基二羟基(三丁基甲硅烷氧基)钛、丙氧基二羟基(三丁基甲硅烷氧基)钛、异丙氧基二羟基(三丁基甲硅烷氧基)钛、丁氧基二羟基(三丁基甲硅烷氧基)钛、异丁氧基二羟基(三丁基甲硅烷氧基)钛、丁氧基二羟基(三丁基甲硅烷氧基)钛、叔丁氧基二羟基(三丁基甲硅烷氧基)钛、环己氧基二羟基(三丁基甲硅烷氧基)钛、苯氧基二羟基(三丁基甲硅烷氧基)钛;
甲氧基二羟基(三异丁基甲硅烷氧基)钛、乙氧基二羟基(三异丁基甲硅烷氧基)钛、丙氧基二羟基(三异丁基甲硅烷氧基)钛、异丙氧基二羟基(三异丁基甲硅烷氧基)钛、丁氧基二羟基(三异丁基甲硅烷氧基)钛、异丁氧基二羟基(三异丁基甲硅烷氧基)钛、仲丁氧基二羟基(三异丁基甲硅烷氧基)钛、叔丁氧基二羟基(三异丁基甲硅烷氧基)钛、环己氧基二羟基(三异丁基甲硅烷氧基)钛、苯氧基二羟基(三异丁基甲硅烷氧基)钛;
甲氧基二羟基(三仲丁氧基甲硅烷氧基)钛、乙氧基二羟基(三仲丁氧基甲硅烷氧基)钛、丙氧基二羟基(三仲丁氧基甲硅烷氧基)钛、异丙氧基二羟基(三仲丁氧基甲硅烷氧基)钛、丁氧基二羟基(三仲丁氧基甲硅烷氧基)钛、异丁氧基二羟基(三仲丁氧基甲硅烷氧基)钛、仲丁氧基二羟基(三仲丁氧基甲硅烷氧基)钛、叔丁氧基二羟基(三仲丁氧基甲硅烷氧基)钛、环己氧基二羟基(三仲丁氧基甲硅烷氧基)钛、苯氧基二羟基(三仲丁氧基甲硅烷氧基)钛;
甲氧基二羟基(三叔丁氧基甲硅烷氧基)钛、乙氧基二羟基(三叔丁氧基甲硅烷氧基)钛、丙氧基二羟基(三叔丁氧基甲硅烷氧基)钛、异丙氧基二羟基(三叔丁氧基甲硅烷氧基)钛、丁氧基二羟基(三叔丁氧基甲硅烷氧基)钛、异丁氧基二羟基(三叔丁氧基甲硅烷氧基)钛、仲丁氧基二羟基(三叔丁氧基甲硅烷氧基)钛、叔丁氧基二羟基(三叔丁氧基甲硅烷氧基)钛、环己氧基二羟基(三叔丁氧基甲硅烷氧基)钛、苯氧基二羟基(三叔丁氧基甲硅烷氧基)钛;
甲氧基二羟基(三环己基甲硅烷氧基)钛、乙氧基二羟基(三环己基甲硅烷氧基)钛、丙氧基二羟基(三环己基甲硅烷氧基)钛、异丙氧基二羟基(三环己基甲硅烷氧基)钛、丁氧基二羟基(三环己基甲硅烷氧基)钛、异丁氧基二羟基(三环己基甲硅烷氧基)钛、仲丁氧基二羟基(三环己基甲硅烷氧基)钛、叔丁氧基二羟基(三环己基甲硅烷氧基)钛、环己氧基二羟基(三环己基甲硅烷氧基)钛、苯氧基二羟基(三环己基甲硅烷氧基)钛;
甲氧基二羟基(三苯基甲硅烷氧基)钛、乙氧基二羟基(三苯基甲硅烷氧基)钛、丙氧基二羟基(三苯基甲硅烷氧基)钛、异丙氧基二羟基(三苯基甲硅烷氧基)钛、丁氧基二羟基(三苯基甲硅烷氧基)钛、异丁氧基二羟基(三苯基甲硅烷氧基)钛、仲丁氧基二羟基(三苯基甲硅烷氧基)钛、叔丁氧基二羟基(三苯基甲硅烷氧基)钛、环己氧基二羟基(三苯基甲硅烷氧基)钛、苯氧基二羟基(三苯基甲硅烷氧基)钛;
等,作为y=3的化合物,可列举
三羟基(三甲基甲硅烷氧基)钛、三羟基(三乙基甲硅烷氧基)钛、三羟基(三丙基甲硅烷氧基)钛、三羟基(三异丙基甲硅烷氧基)钛、三羟基(三丁基甲硅烷氧基)钛、三羟基(三异丁基甲硅烷氧基)钛、三羟基(三仲丁氧基甲硅烷氧基)钛、三羟基(三叔丁氧基甲硅烷氧基)钛、三羟基(三环己基甲硅烷氧基)钛、三羟基(三苯基甲硅烷氧基)钛;
等。
金属原子M为Zr时,作为y=2的化合物,可列举
甲氧基二羟基(三甲基甲硅烷氧基)锆、乙氧基二羟基(三甲基甲硅烷氧基)锆、丙氧基二羟基(三甲基甲硅烷氧基)锆、异丙氧基二羟基(三甲基甲硅烷氧基)锆、丁氧基二羟基(三甲基甲硅烷氧基)锆、异丁氧基二羟基(三甲基甲硅烷氧基)锆、仲丁氧基二羟基(三甲基甲硅烷氧基)锆、叔丁氧基二羟基(三甲基甲硅烷氧基)锆、环己氧基二羟基(三甲基甲硅烷氧基)锆、苯氧基二羟基(三甲基甲硅烷氧基)锆;
甲氧基二羟基(三乙基甲硅烷氧基)锆、乙氧基二羟基(三乙基甲硅烷氧基)锆、丙氧基二羟基(三乙基甲硅烷氧基)锆、异丙氧基二羟基(三乙基甲硅烷氧基)锆、丁氧基二羟基(三乙基甲硅烷氧基)锆、异丁氧基二羟基(三乙基甲硅烷氧基)锆、仲丁氧基二羟基(三乙基甲硅烷氧基)锆、叔丁氧基二羟基(三乙基甲硅烷氧基)锆、环己氧基二羟基(三乙基甲硅烷氧基)锆、苯氧基二羟基(三乙基甲硅烷氧基)锆;
甲氧基二羟基(三丙基甲硅烷氧基)锆、乙氧基二羟基(三丙基甲硅烷氧基)锆、丙氧基二羟基(三丙基甲硅烷氧基)锆、异丙氧基二羟基(三丙基甲硅烷氧基)锆、丁氧基二羟基(三丙基甲硅烷氧基)锆、异丁氧基二羟基(三丙基甲硅烷氧基)锆、仲丁氧基二羟基(三丙基甲硅烷氧基)锆、叔丁氧基二羟基(三丙基甲硅烷氧基)锆、环己氧基二羟基(三丙基甲硅烷氧基)锆、苯氧基二羟基(三丙基甲硅烷氧基)锆;
甲氧基二羟基(三异丙基甲硅烷氧基)锆、乙氧基二羟基(三异丙基甲硅烷氧基)锆、丙氧基二羟基(三异丙基甲硅烷氧基)锆、异丙氧基二羟基(三异丙基甲硅烷氧基)锆、丁氧基二羟基(三异丙基甲硅烷氧基)锆、异丁氧基二羟基(三异丙基甲硅烷氧基)锆、仲丁氧基二羟基(三异丙基甲硅烷氧基)锆、叔丁氧基二羟基(三异丙基甲硅烷氧基)锆、环己氧基二羟基(三异丙基甲硅烷氧基)锆、苯氧基二羟基(三异丙基甲硅烷氧基)锆;
甲氧基二羟基(三丁基甲硅烷氧基)锆、乙氧基二羟基(三丁基甲硅烷氧基)锆、丙氧基二羟基(三丁基甲硅烷氧基)锆、异丙氧基二羟基(三丁基甲硅烷氧基)锆、丁氧基二羟基(三丁基甲硅烷氧基)锆、异丁氧基二羟基(三丁基甲硅烷氧基)锆、丁氧基二羟基(三丁基甲硅烷氧基)锆、叔丁氧基二羟基(三丁基甲硅烷氧基)锆、环己氧基二羟基(三丁基甲硅烷氧基)锆、苯氧基二羟基(三丁基甲硅烷氧基)锆;
甲氧基二羟基(三异丁基甲硅烷氧基)锆、乙氧基二羟基(三异丁基甲硅烷氧基)锆、丙氧基二羟基(三异丁基甲硅烷氧基)锆、异丙氧基二羟基(三异丁基甲硅烷氧基)锆、丁氧基二羟基(三异丁基甲硅烷氧基)锆、异丁氧基二羟基(三异丁基甲硅烷氧基)锆、仲丁氧基二羟基(三异丁基甲硅烷氧基)锆、叔丁氧基二羟基(三异丁基甲硅烷氧基)锆、环己氧基二羟基(三异丁基甲硅烷氧基)锆、苯氧基二羟基(三异丁基甲硅烷氧基)锆;
甲氧基二羟基(三仲丁氧基甲硅烷氧基)锆、乙氧基二羟基(三仲丁氧基甲硅烷氧基)锆、丙氧基二羟基(三仲丁氧基甲硅烷氧基)锆、异丙氧基二羟基(三仲丁氧基甲硅烷氧基)锆、丁氧基二羟基(三仲丁氧基甲硅烷氧基)锆、异丁氧基二羟基(三仲丁氧基甲硅烷氧基)锆、仲丁氧基二羟基(三仲丁氧基甲硅烷氧基)锆、叔丁氧基二羟基(三仲丁氧基甲硅烷氧基)锆、环己氧基二羟基(三仲丁氧基甲硅烷氧基)锆、苯氧基二羟基(三仲丁氧基甲硅烷氧基)锆;
甲氧基二羟基(三叔丁氧基甲硅烷氧基)锆、乙氧基二羟基(三叔丁氧基甲硅烷氧基)锆、丙氧基二羟基(三叔丁氧基甲硅烷氧基)锆、异丙氧基二羟基(三叔丁氧基甲硅烷氧基)锆、丁氧基二羟基(三叔丁氧基甲硅烷氧基)锆、异丁氧基二羟基(三叔丁氧基甲硅烷氧基)锆、仲丁氧基二羟基(三叔丁氧基甲硅烷氧基)锆、叔丁氧基二羟基(三叔丁氧基甲硅烷氧基)锆、环己氧基二羟基(三叔丁氧基甲硅烷氧基)锆、苯氧基二羟基(三叔丁氧基甲硅烷氧基)锆;
甲氧基二羟基(三环己基甲硅烷氧基)锆、乙氧基二羟基(三环己基甲硅烷氧基)锆、丙氧基二羟基(三环己基甲硅烷氧基)锆、异丙氧基二羟基(三环己基甲硅烷氧基)锆、丁氧基二羟基(三环己基甲硅烷氧基)锆、异丁氧基二羟基(三环己基甲硅烷氧基)锆、仲丁氧基二羟基(三环己基甲硅烷氧基)锆、叔丁氧基二羟基(三环己基甲硅烷氧基)锆、环己氧基二羟基(三环己基甲硅烷氧基)锆、苯氧基二羟基(三环己基甲硅烷氧基)锆;
甲氧基二羟基(三苯基甲硅烷氧基)锆、乙氧基二羟基(三苯基甲硅烷氧基)锆、丙氧基二羟基(三苯基甲硅烷氧基)锆、异丙氧基二羟基(三苯基甲硅烷氧基)锆、丁氧基二羟基(三苯基甲硅烷氧基)锆、异丁氧基二羟基(三苯基甲硅烷氧基)锆、仲丁氧基二羟基(三苯基甲硅烷氧基)锆、叔丁氧基二羟基(三苯基甲硅烷氧基)锆、环己氧基二羟基(三苯基甲硅烷氧基)锆、苯氧基二羟基(三苯基甲硅烷氧基)锆;
等,作为y=3的化合物,可列举
三羟基(三甲基甲硅烷氧基)锆、三羟基(三乙基甲硅烷氧基)锆、三羟基(三丙基甲硅烷氧基)锆、三羟基(三异丙基甲硅烷氧基)锆、三羟基(三丁基甲硅烷氧基)锆、三羟基(三异丁基甲硅烷氧基)锆、三羟基(三仲丁氧基甲硅烷氧基)锆、三羟基(三叔丁氧基甲硅烷氧基)锆、三羟基(三环己基甲硅烷氧基)锆、三羟基(三苯基甲硅烷氧基)锆;
等。
(通式(2)所示的化合物的制造方法)
通式(2)所示的化合物的制造方法没有特别限制,例如,R5为碳原子数1〜12的烷基时,可通过使金属烷氧化物、和下述通式(4)所示的化合物以规定的摩尔比发生反应而得到,以得到n为1、2或3的化合物。
[化6]
通式(4)中,R8与通式(2)中的R4相同。
作为通式(4)所示的化合物的具体例,可列举三甲基硅醇、三乙基硅醇、三丙基硅醇、三异丙基硅醇、三丁基硅醇、三异丁基硅醇、三仲丁基硅醇、三叔丁基硅醇、三戊基硅醇、三己基硅醇、三庚基硅醇、三辛基硅醇、三−2−乙基己基硅醇、三壬基硅醇、十三烷基硅醇、三苯基硅醇、(苯基)(二甲基)硅醇、(苯基)(二乙基)硅醇、(二苯基)(甲基)硅醇、(二苯基)(乙基)硅醇、二苯基硅烷二醇、二萘基硅烷二醇、三苄基硅醇、三苯基乙基硅醇、(三甲基甲硅烷氧基)(二甲基)硅醇、(三甲基甲硅烷氧基)(二甲基)硅醇、(三乙基甲硅烷氧基)(二甲基)硅醇等。其中,特别优选三甲基硅醇、三乙基硅醇。
作为金属烷氧化物,没有特别限定,例如金属原子M为Ti时,可列举四甲氧基钛、四乙氧基钛、四丙氧基钛、四异丙氧基钛、四丁氧基钛、四仲丁氧基钛、四异丁氧基钛、四叔丁氧基钛、四戊氧基钛、四己氧基钛、四庚氧基钛、四辛氧基钛、四壬氧基钛、四癸氧基钛等,金属原子M为Zr时,可列举四甲氧基锆、四乙氧基锆、四丙氧基锆、四异丙氧基锆、四丁氧基锆、四仲丁氧基锆、四异丁氧基锆、四叔丁氧基锆、四戊氧基锆、四己氧基锆、四庚氧基锆、四辛氧基锆、四壬氧基锆、四癸氧基锆等,金属原子M为Al时,可列举三甲氧基铝、三乙氧基铝、三丙氧基铝、三异丙氧基铝、三丁氧基铝、三仲丁氧基铝、仲丁氧基(二异丙氧基)铝、三异丁氧基铝、三叔丁氧基铝、三戊氧基铝、三己氧基铝、三庚氧基铝、三辛氧基铝、三壬氧基铝、三癸氧基铝等。
通式(2)所示的化合物为通式(3)所示的化合物时,例如,可利用上述方法通过使所得通式(2)所示的金属烷氧化物水解而得到。水解可使用一般的方法。例如,可列举向通式(2)所示的金属烷氧化物添加溶剂、水,根据需要添加催化剂,在−20〜60℃下搅拌0.1〜100小时左右的方法等。根据需要,可通过使水解副产物(甲醇等醇)减压蒸馏而馏去。
作为上述反应溶剂,没有特别限定,适合使用具有醇性羟基的化合物、酯类、醚类、酮类。作为醇系溶剂的具体例,可列举甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、叔丁醇、丙酮醇、3−羟基−3−甲基−2−丁酮、5−羟基−2−戊酮、4−羟基−4−甲基−2−戊酮(二丙酮醇)、乳酸乙酯、乳酸丁酯、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、丙二醇单叔丁基醚、二乙二醇单甲基醚、二乙二醇单乙基醚、二丙二醇单甲基醚、3−甲氧基−1−丁醇、3−甲基−3−甲氧基−1−丁醇、乙二醇、丙二醇等。
作为酯类,可列举乙酸乙酯、乙酸丙酯、乙酸异丙酯、乙酸丁酯、乙酸异丁酯、丙二醇单甲基醚乙酸酯、3−甲氧基−1−丁基乙酸酯、3−甲基−3−甲氧基−1−丁基乙酸酯、乙酰乙酸乙酯、环己醇乙酸酯等。
作为醚类,可列举二乙基醚、二异丙基醚、二丁基醚、二苯基醚、二乙二醇乙基甲基醚、二乙二醇二甲基醚、1,2−二乙氧基乙烷、二丙二醇二甲基醚等。
作为酮类溶剂的具体例,可列举甲基异丁基酮、二异丙基酮、二异丁基酮、乙酰基丙酮、环戊酮、环己酮、环庚酮等。
作为其它可优选使用的溶剂,可列举碳酸丙烯酯、N−甲基吡咯烷酮等。
另外,通过调整水解反应所用的水的添加量,可调整通式(3)所示的金属化合物的羟基的量。例如,y=1、即具有1个羟基的金属化合物时,可通过添加相对于金属烷氧化物1摩尔为1摩尔的水而得到。此外,通过添加相对于作为水解性基团的烷氧基1摩尔为1摩尔的水,可得到烷氧基完全水解了的金属化合物。水的添加量优选相对于烷氧基为0.1〜2摩尔。
根据需要而添加的催化剂没有特别限制,优选使用酸性催化剂或碱性催化剂。作为酸催化剂的具体例,可列举盐酸、硝酸、硫酸、氢氟酸、磷酸、乙酸、三氟乙酸、甲酸、多元羧酸或者其酸酐、离子交换树脂。作为碱催化剂的具体例,可列举三乙基胺、三丙基胺、三丁基胺、三戊基胺、三己基胺、三庚基胺、三辛基胺、二乙基胺、二丙基胺、二丁基胺、二异丁基胺、二戊基胺、二己基胺、二庚基胺、二辛基胺、三乙醇胺、二乙醇胺、二环己基胺、二环己基甲基胺、氢氧化钠、氢氧化钾、具有氨基的烷氧基硅烷、离子交换树脂。催化剂的添加量优选相对于通式(2)所示的甲硅烷氧基含有化合物100重量份为0.01〜30重量份。
(聚金属氧烷的制造方法)
通式(2)所示的化合物的水解以及部分缩合和聚合中可使用一般的方法。例如,水解的反应条件优选:在溶剂中,向通式(2)所示的化合物花费1〜180分钟添加水后,在室温〜110℃下反应1〜180分钟。通过在这样的条件下进行水解反应,可抑制剧烈的反应。反应温度优选30〜150℃。而且可根据需要添加催化剂。
另外,作为部分缩合和聚合的反应条件,优选在利用通式(2)所示的化合物的水解反应得到水解物后,将反应液直接在50℃〜180℃下加热1〜100小时。此外,为了提高聚金属氧烷的聚合度,也可以再加热或添加催化剂。此外,根据需要,在水解反应后,通过加热和/或减压而馏出适量的生成醇等,去除,然后可添加任意溶剂。
作为溶剂,没有特别限定,适合使用具有醇性羟基的化合物、酯类、醚类、酮类。使用这些溶剂时,可使聚金属氧烷的稳定性提高,可使所得涂布膜的透明性提高。
作为醇系溶剂的具体例,可列举甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、叔丁醇、丙酮醇、3−羟基−3−甲基−2−丁酮、5−羟基−2−戊酮、4−羟基−4−甲基−2−戊酮(二丙酮醇)、乳酸乙酯、乳酸丁酯、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单正丙基醚、丙二醇单正丁基醚、丙二醇单叔丁基醚、二乙二醇单甲基醚、二乙二醇单乙基醚、二丙二醇单甲基醚、3−甲氧基−1−丁醇、3−甲基−3−甲氧基−1−丁醇、乙二醇、丙二醇等。
作为酯类,可列举乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯、乙酸异丁酯、丙二醇单甲基醚乙酸酯、3−甲氧基−1−丁基乙酸酯、3−甲基−3−甲氧基−1−丁基乙酸酯、乙酰乙酸乙酯、环己醇乙酸酯等。
作为醚类,可列举二乙基醚、二异丙基醚、二正丁基醚、二苯基醚、二乙二醇乙基甲基醚、二乙二醇二甲基醚、1,2−二甲氧基乙烷、1,2−二乙氧基乙烷、二丙二醇二甲基醚等。
作为酮类溶剂的具体例,可列举甲基异丁基酮、二异丙基酮、二异丁基酮、乙酰基丙酮、环戊酮、环己酮、环庚酮等。
作为其它可优选使用的溶剂,可列举碳酸丙烯酯、N−甲基吡咯烷酮等。
另外,通过调整水解反应所用的水的添加量,可调整通式(2)所示的化合物的水解率。水的添加量优选相对于烷氧基1摩尔为0.1〜2摩尔。
根据需要而添加的催化剂没有特别限制,优选使用酸性催化剂或碱性催化剂。作为酸催化剂的具体例,可列举盐酸、硝酸、硫酸、氢氟酸、磷酸、乙酸、三氟乙酸、甲酸、多元羧酸或者其酸酐、离子交换树脂。作为碱催化剂的具体例,可列举三乙基胺、三丙基胺、三丁基胺、三戊基胺、三己基胺、三庚基胺、三辛基胺、二乙基胺、二丙基胺、二丁基胺、二异丁基胺、二戊基胺、二己基胺、二庚基胺、二辛基胺、三乙醇胺、二乙醇胺、二环己基胺、二环己基甲基胺、氢氧化钠、氢氧化钾、具有氨基的烷氧基硅烷、离子交换树脂。
更优选的催化剂为碱催化剂。通过使用碱催化剂,尤其可得到高分子量的聚金属氧烷。碱催化剂中,特别优选三丙基胺、三异丁基胺、三戊基胺、三异戊基胺、三己基胺、三庚基胺、三辛基胺、二丁基胺、二异丁基胺、二戊基胺、二己基胺、二庚基胺、二辛基胺。
此外,从组合物的储存稳定性的观点出发,优选水解、部分缩合和聚合后的聚金属氧烷溶液中不含上述催化剂,可根据需要进行催化剂的去除。去除方法没有特别限制,从操作简便性和去除性的观点,优选水洗涤、和/或离子交换树脂的处理。水洗涤是用适当的疏水性溶剂稀释聚金属氧烷溶液后,用水洗涤数次,利用蒸发器浓缩所得有机层的方法。利用离子交换树脂的处理是使聚硅氧烷溶液与适当的离子交换树脂接触的方法。
(聚金属氧烷的组合物)
本发明的聚金属氧烷可与溶剂、其它必要的成分混合而形成组合物。
本发明的聚金属氧烷优选利用溶剂稀释、调整固体成分浓度。溶剂没有特别限制,优选使用与聚金属氧烷的合成中使用的溶剂相同的溶剂。含有聚金属氧烷的溶液的固体成分浓度优选达到0.1〜50wt%,通过使固体成分浓度为该范围,涂布膜的膜厚控制变得良好。
调整聚金属氧烷溶液的固体成分时,可添加其它成分。作为其它成分,可列举无机颗粒、表面活性剂、硅烷偶联剂、交联剂、交联促进剂等。
无机颗粒优选为了提高固化膜的折射率而使用。无机颗粒优选为选自(b1)铝化合物颗粒、锡化合物颗粒、钛化合物颗粒和锆化合物颗粒中的1者以上的颗粒、或(b2)选自铝化合物、锡化合物、钛化合物和锆化合物中的1者以上的金属化合物与硅化合物的复合颗粒。以下,将这些颗粒总称为"金属化合物颗粒"。通过添加这些颗粒,可更加提高折射率。
金属化合物颗粒的平均粒径优选1nm〜400nm。通过为1nm以上,可更加抑制厚膜形成时的裂纹发生,更优选为5nm以上。另外,通过为400nm以下,可使折射率提高而不使固化膜相对于可见光的透明性降低,更优选70nm以下。
作为金属化合物颗粒的例子,可列举氧化锡−氧化钛复合颗粒的“オプトレイクTR−502”、“オプトレイクTR−504”、氧化硅−氧化钛复合颗粒的“オプトレイクTR−503”、“オプトレイクTR−513”、“オプトレイクTR−520”、“オプトレイクTR−527”、“オプトレイクTR−528”、“オプトレイクTR−529”、“オプトレイクTR−543”、“オプトレイクTR−544”、“オプトレイクTR−550”、氧化钛颗粒的“オプトレイクTR−505”(以上为商品名、催化剂化成工业(株)制)、NOD−7771GTB(商品名、ナガセケムテックス(株)制)、氧化锆颗粒((株)高纯度化学研究所制)、氧化锡−氧化锆复合颗粒(催化剂化成工业(株)制)、氧化锡颗粒((株)高纯度化学研究所制)、“バイラール”Zr−C20(氧化钛颗粒;平均粒径=20nm;多木化学(株)制)、ZSL−10A(氧化钛颗粒;平均粒径=60−100nm;第一稀元素株式会公司制)、ナノユースOZ−30M(氧化钛颗粒;平均粒径=7nm;日产化学工业(株)制)、SZR−M或SZR−K(以上为氧化锆颗粒;均为堺化学(株)制)、HXU−120JC(氧化氧化锆颗粒;住友大阪水泥(株)制)、ZR−010(氧化氧化锆颗粒;株式会公司ソーラー)或ZRPMA(氧化锆颗粒;シーアイ化成株式会公司)。
为了提高涂布时的流动性,优选使用表面活性剂。表面活性剂可残存于固化膜。
表面活性剂的种类没有特别限制,可使用例如“メガファック(注册商标)”F142D、メガファックF172、メガファックF173、メガファックF183、メガファックF444、メガファックF445、メガファックF470、メガファックF475、メガファックF477(以上DIC(株)制)、NBX−15、FTX−218、DFX−18((株)ネオス制)等氟系表面活性剂、BYK−333、BYK−301、BYK−331、BYK−345、BYK−307(ビックケミージャパン(株)制)等硅酮系表面活性剂、聚环氧烷系表面活性剂、聚(甲基)丙烯酸酯系表面活性剂等。它们可以使用2种以上。
表面活性剂的添加含量优选相对于聚金属氧烷100重量份为0.001〜10重量份,进一步优选0.01〜1重量份。
硅烷偶联剂优选为了提高与基板的密合性而使用。硅烷偶联剂没有特别限制,例如可使用乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、2−(3,4环氧环己基)乙基三甲氧基硅烷、3−环氧丙氧基丙基三甲氧基硅烷、3−甲基丙烯酰氧基丙基甲基二甲氧基硅烷、3−甲基丙烯酰氧基丙基三甲氧基硅烷、3−丙烯酰氧基丙基三甲氧基硅烷、3−氨基丙基三甲氧基硅烷、3−氨基丙基三乙氧基硅烷、3−三乙氧基甲硅烷基−N−(1,3−二甲基−丁叉基)丙基胺、3−巯基丙基甲基二甲氧基硅烷、3−巯基丙基三甲氧基硅烷、3−异氰酸酯丙基三乙氧基硅烷、二苯基二甲氧基硅烷、三甲基硅醇、二苯基硅烷二醇等。
硅烷偶联剂的添加量优选相对于聚金属氧烷100重量份为0.1〜50重量份,进一步优选1〜20重量份。
交联剂和交联促进剂优选为了提高固化膜的耐药品性而使用。交联剂和交联促进剂的种类没有特别限制,例如可使用单仲丁氧基二异丙醇铝、仲丁醇铝、乙基乙酰乙酸酯铝二异丙醇、三(乙基乙酸酯)铝、烷基アセト二异丙醇铝、单乙酰基アセトネート双(乙基乙酰乙酸酯)铝、三(乙酰基アセトネート)铝、三(乙酰基乙酸酯)锆、三(乙基乙酰乙酸酯)锆、三(乙酰基乙酸酯)钛、三(乙基乙酰乙酸酯)钛等。
交联剂和交联促进剂的含量优选以总量计、相对于聚金属氧烷100重量份为0.1〜50重量份,进一步优选1〜20重量份。交联剂和交联促进剂可以各自单独使用,也可以两者组合使用。
基板没有特别限制,可列举硅晶片、蓝宝石晶片、玻璃、光学膜。作为玻璃,可列举例如碱玻璃、无碱玻璃、热强化玻璃或化学强化玻璃。作为光学膜,可列举由丙烯酸树脂、聚酯树脂、聚碳酸酯、聚芳酯、聚醚砜、聚丙烯、聚乙烯、聚酰亚胺或环烯烃聚合物形成的膜。
(形成固化膜的工序)
本发明的聚金属氧烷或含有其的组合物可通过加热而形成固化膜。这样得到的固化膜由于是以在主链具有电子密度高的金属原子的树脂作为主体的固化膜,因此可提高固化膜中的金属原子的密度,可容易地得到高折射率。此外,由于形成不具有自由电子的电介质,因此可得到高透明性和耐热性。
可使用含有聚金属氧烷的溶液的涂布方法所公知的方法。作为涂布所用的装置,可列举旋涂、浸涂、幕流涂布、喷涂或狭缝涂布等全表面涂布装置或丝网印刷、辊涂、微凹版涂布或喷墨等印刷装置。
涂布后,根据需要,可使用烤盘、烤箱等加热装置进行加热(预焙Pre-baking)。预焙优选在50〜150℃的温度范围内进行30秒〜30分钟,形成预焙膜。通过进行预焙,可得到膜厚均一性好的膜。预焙后的膜厚优选0.1〜15μm。
通过将涂布膜、或者预焙膜使用烤盘或者烤箱等加热装置在150℃〜450℃的温度范围下加热(固化)30秒〜2小时左右,可得到含有聚金属氧烷的固化膜。该固化膜的膜厚优选0.1〜15μm。
所得固化膜在波长550nm下的折射率优选1.58以上且2.20以下,更优选1.65以上且2.10以下。
固化膜的折射率可以利用以下方法测定。使用光谱椭偏仪,测定来自固化膜和基板的反射光的偏光状态变化,得到与入射光的相位差和振幅反射率的光谱。通过拟合计算模型的介电函数以接近所得光谱,得到折射率光谱。由所得折射率光谱读取波长550nm下的折射率值,由此得到固化膜的折射率。
所得固化膜优选在波长400nm下的每1μm膜厚的透光率为90%以上。若透光率在透明基板上制成,则可利用以下方法测定。首先,使用分光光度计,测定基板的紫外可见吸收光谱,将其作为参照。接着,测定在透明基板上制成的固化膜的紫外可见吸收光谱,通过与参照的差异,算出固化膜的紫外可见吸收光谱。使用所得紫外可见吸收光谱和固化膜的膜厚,算出微透镜的波长400nm下的每1μm膜厚的透光率。
在硅晶片等不透明基板上形成的固化膜的透光率可利用以下方法测定。使用光谱椭偏仪,测定来自固化膜和基板的反射光的偏光状态变化,得到与入射光的相位差和振幅反射率的光谱。通过拟合计算模型的介电函数以接近所得光谱,得到消衰系数光谱。由所得消衰系数光谱读取波长400nm下的消衰系数,通过使用下述式而求出以波长400nm下的膜厚1μm换算的透光率(%)
透光率=exp(−4πkt/λ)
其中,k表示消衰系数,t表示换算膜厚(μm),λ表示测定波长(nm)。应予说明,本测定中为了求出1μm换算的透光率,t为1(μm)。
(用途)
上述固化膜由于折射率、透明性优异,因此适用于固体成像元件、光学过滤器、显示器等电子部件。更具体而言,可列举背照式CMOS图像传感器等固体成像元件等中形成的聚焦用微透镜、光波导、设置作为光学过滤器的防反射膜、显示器用TFT基板的平坦化材料、液晶显示器等彩色过滤器及其保护膜、移相器等。
其中,由于可兼顾高透明性和高折射率,特别适合用于在固体成像元件上形成的聚焦用微透镜、或连接聚焦用微透镜和光传感器部分的光波导。此外,也可用作半导体装置的缓冲涂层(Buffer coat)、层间绝缘膜、各种保护膜。
(接触式传感器用途)
由本发明的聚金属氧烷或其组合物得到的固化膜由于高透明性和高折射率,因此适合用于智能手机、平板电脑终端所使用的接触式传感器构件。更具体而言,可列举传感器形成中使用的透明导电膜的上部或下部形成的绝缘层薄膜。
作为接触式传感器、和使用其的显示器的问题之一,可列举基于Indium TinOxide(以下简写为"ITO")等透明导电膜图案的可见的终端的外观恶化。作为抑制透明电极图案的可见性的代表的技术,开发了通过在透明电极的上部或下部形成绝缘层薄膜,降低界面反射,抑制透明电极图案的可见性的技术(例如日本特开平1−205122号公报、日本特开平6−033000号公报、日本特开平8−240800号公报)。在该绝缘层薄膜,由于透明电极图案的折射率高,因此要求高折射率和透明性。
作为降低透明电极图案的可见性的技术,开发了将Nb2O3和SiO2的薄膜设置作为底涂层或顶涂层的技术(例如日本特开2010−152809号公报、日本特开2010−086684号公报)。进而,为了低成本、省工序,开发了形成折射率为1.58〜1.85的有机系薄膜和氧化硅薄膜的技术(例如WO2014/119372号)。该技术使用含有单体的折射率高的氧化钛颗粒、钛酸钡颗粒等钛氧化物微粒或氧化锆颗粒等锆氧化物颗粒的有机组合物,将折射率控制在期望的范围内。或将折射率高的取代基导入有机成分、将折射率控制在期望的范围内。
但是,用以往的金属氧化物颗粒进行折射率控制时,除金属氧化物颗粒价格高外,而且金属氧化物颗粒的含有比例增大,因此变得分散不良,存在颗粒沉淀的问题。此外,折射率在基于折射率高的取代基的控制下,折射率只能在能变化的范围内变化,因此难以实现超过1.8这样的高折射率。
因此,通过使用由本发明的聚金属氧烷或其组合物得到的固化膜,可简便地控制折射率,因此可容易且低成本地提供大幅降低透明导电膜图案的可见性的基板。
具体而言,通过具有构件,所述构件接触式传感器具有自透明基底基材的上表面起以透明导电薄膜(I)、本发明的聚金属氧烷或其组合物得到的固化膜(II)的顺序层叠薄膜的部位,可减弱在下层形成的透明导电薄膜(I)的上部界面和下部界面的反射光,可降低透明导电薄膜的图案可见性。并且,由于透明导电膜被薄膜保护,因此可使接触式传感器的耐久性提高。
对具有以透明导电薄膜(I)、由本发明的聚金属氧烷或其组合物得到的固化膜(II)的顺序层叠薄膜的部位的构件进行详细说明。
作为透明基底基材的原材料,只要具有透过光的功能就没有特别限制,优选每0.1mm厚度的全线透过率(基于JIS K 7361−1:1997)为80%以上,可列举例如玻璃、光学膜。从耐热性、耐药品性的观点出发,更优选玻璃。作为玻璃,可列举例如碱玻璃、无碱玻璃、热强化玻璃或化学强化玻璃,优选作为接触面板的盖板玻璃广泛使用的热强化玻璃或化学强化玻璃。作为光学膜,可列举丙烯酸树脂、聚酯树脂、聚碳酸酯、聚芳酯、聚醚砜、聚丙烯、聚乙烯、聚酰亚胺或环烯烃聚合物。其中,从透明性的观点出发,优选丙烯酸树脂、聚酯树脂、聚碳酸酯或环烯烃聚合物。作为丙烯酸树脂,优选聚甲基丙烯酸甲酯。作为聚酯树脂,优选聚对苯二甲酸乙二醇酯、聚萘二甲酸乙二醇酯或聚对苯二甲酸丁二醇酯。作为聚碳酸酯,优选通过双酚A和光气的缩聚而得到的树脂。作为聚酰亚胺,从透明性的观点出发,优选以脂肪族羧酸二酐和/或脂肪族二胺作为单体的树脂。作为环烯烃聚合物,优选例如使环己烯或降冰片烯或它们的衍生物加成聚合或开环易位聚合而得到的聚合物。
作为透明导电薄膜(I),ITO薄膜最普遍。本申请以ITO薄膜举例说明,但不限定于它们。作为透明导电薄膜的形成方法,由于能容易地得到低电阻的薄膜,能控制精密的膜厚,因此优选溅射法。透明导电薄膜(I)的膜厚优选1〜200nm。
在透明导电薄膜(I)的上表面层叠的由本发明的聚金属氧烷或其组合物得到的固化膜(II)的膜厚和折射率各自优选0.01〜3μm和1.58〜1.95。通过在此范围,可控制包含在前述组合物的薄膜(II)的上部界面和下部界面的反射光的相位和强度,可减弱在上述这样的透明导电薄膜(I)的上部界面和下部界面的反射光,降低透明导电薄膜的图案可见性。通过使包含前述组合物的薄膜(II)的膜厚在此范围,可控制相位,图案可见性的降低效果充分。通过包含前述组合物的薄膜(II)的折射率在此范围,可控制反射光的强度,图案可见性的降低效果充分。作为膜厚和折射率的范围,进一步优选膜厚和折射率各自为0.1〜2.5μm和1.65〜1.95,特别优选0.15〜2μm和1.80〜1.95。
进而,优选具有在由本发明的聚金属氧烷或其组合物得到的固化膜(II)的上表面层叠氧化硅薄膜(III)和/或折射率为1.46〜1.53的透明粘接薄膜(IV)的部位。
通过具有氧化硅薄膜(III),可控制下部界面的反射光(即由前述聚金属氧烷或其组合物得到的固化膜(II)的上部界面的反射光)的强度。此外,由于可同时保护包含透明导电薄膜(I)的基底金属,因此在接触式传感器用途中,可使接触式传感器的信赖性提高。
氧化硅薄膜(III)的膜厚优选0.01〜10μm。低于0.01μm时,由于影响上部界面的反射光而难以得到图案可见性的降低效果,进而不能得到保护基底金属的功能。超过10μm时,因略微的变形而变得容易导入裂纹,会损坏接触面板的信赖性和外观。
作为氧化硅薄膜(III)的形成方法,可列举例如溅射法、真空蒸镀法(电子束法)、离子电镀法(IP法)或CVD(Chemical Vapor Deposition)法等干法工艺或SOG(Spin onGlass)等湿法工艺。其中,由于CVD法能在较低温度下形成缺陷少的薄膜,故而优选。
透明粘接薄膜(IV)是指由透明粘接剂形成的薄膜。在此,透明粘接剂是指透光且具有粘接性的原材料。
从粘接性和透明性的观点出发,透明粘接薄膜(IV)的膜厚优选1〜200μm。
透明粘接剂的粘接力优选3〜100N/20mm。而且,从接触式传感器的外观的观点出发,透明粘接剂的透过率以全线透过率(JIS K 7361−1:1997)计优选90%以上。
作为透明粘接剂,可列举例如热固化型粘接剂或UV固化型粘接剂。作为折射率为1.46〜1.52的热固化型透明粘接剂,可列举例如以碳原子数1〜20的烷基(甲基)丙烯酸酯、含有羟基的(甲基)丙烯酸酯和/或含有羧基的(甲基)丙烯酸衍生物作为构成单体的共聚物、或者含有多官能异氰酸酯化合物和/或多官能环氧化合物的热固化型粘接剂。作为折射率为1.46〜1.52的UV固化型透明粘接剂,可列举例如以单官能或多官能的(甲基)丙烯酸酯单体和/或低聚物、和光聚合引发剂作为主成分的UV固化型粘接剂。
作为这样的透明粘接剂,可使用用于使各种基板之间贴合的OCA(Optical ClaerAdhesive)材料(热固化型粘接剂的通称)或OCR(Optical Claer Adhesive Resin)材料(UV固化型粘接剂的通称)。而且,作为由上述这样的透明粘接剂形成的透明粘接薄膜(IV),可使用具备防飞散膜等市售多功能膜的粘接剂。
作为能形成透明粘接薄膜(IV)的市售OCA材料,可列举例如8171CL、8172CL、8146−1或8146−2(均为住友スリーエム(株)制)、CS9622T、CS9621T或CS9070(均为日东电工(株)制)、TE−9000、TE−7000、TE−8500或DA−5000H(以上为日立化成(株)制)或MO−3010或MO−T010(均为リンテック(株)制)。作为能形成透明粘接薄膜(IV)的市售OCR材料,可列举例如XV−SV−B1或XV−7811(均为パナソニック(株)制)或UVP−1003、UVP−1100、UVP−7100或UVP−7000(均为东亚合成(株)制)。作为能形成透明粘接薄膜(IV)的市售带透明粘接剂的多功能膜,可列举例如广泛用作防飞散膜的HA−110、HA−115、HA−116或HA−203(均为リンテック(株)制)或HC1100F−BP或HC2120F−BP(均为DIC(株)制)。
具有以透明导电薄膜(I)、由本发明的聚金属氧烷或其组合物得到的固化膜(II)的顺序层叠薄膜的部位的构件适用于显示器用途。例如可列举电阻膜式接触面板、静电容量式接触面板、TFT基板,优选用于静电容量式接触面板,更优选用于盖板玻璃一体型静电容量式接触面板。
(透镜用途)
由本发明的聚金属氧烷得到的固化膜由于折射率、透明性优异,因此适用于透镜。更具体而言,可适用于背照式CMOS图像传感器等固体成像元件等中形成的聚焦用微透镜。
固体成像元件具备在半导体基板上以矩阵状排列的多个光电转换元件。在各光电转换元件前方,将入射光聚焦于光电转换元件的微透镜排列于每个光电转换元件。从聚焦效率的观点出发,对微透镜要求高折射率和透明性。
作为这样的微透镜的制造方法,有利用干式蚀刻的方法。该方法为以下这样的方法。在基板上形成透镜材料的固化膜。接着,在固化膜上以与微透镜相同的形状形成光刻胶的图案。然后,光刻胶与固化膜一起进行干式蚀刻,将光刻胶的图案转写到固化膜上,得到微透镜。
由本发明的聚金属氧烷得到的固化膜由于形成不具有自由电子的电介质,因此可得到高透明性和耐热性。此外,可形成以树脂成分作为主体的固化膜,干式蚀刻时的固化膜和蚀刻气体的反应性可在膜整体中基本均一。因此,干式蚀刻速度不会局部地产生差别,可得到表面不粗糙且平滑的微透镜。
由聚金属氧烷的固化膜形成的透镜的制造方法没有特别限制,优选包括在基板上形成包含本发明的聚金属氧烷的固化膜的工序、在固化膜上形成光刻胶图案的工序、和将光刻胶图案和固化膜干式蚀刻的工序。对各工序进行详细说明。
上述的基板没有特别限制,可列举硅晶片、蓝宝石晶片、玻璃、光学膜。作为玻璃,可列举例如碱玻璃、无碱玻璃、热强化玻璃或化学强化玻璃。作为光学膜,可列举由丙烯酸树脂、聚酯树脂、聚碳酸酯、聚芳酯、聚醚砜、聚丙烯、聚乙烯、聚酰亚胺或环烯烃聚合物形成的膜。
作为在基板上形成含有聚金属氧烷的固化膜的方法,优选将含有聚金属氧烷的溶液涂布、加热而形成固化膜的方法。
在含有前述聚金属氧烷的固化膜上形成光刻胶层,将该光刻胶层通过光刻而进行图案化,由此得到光刻胶图案。
光刻胶层可通过涂布市售的光刻胶而得到。涂布方法可使用公知的方法。作为涂布所用的装置,可列举旋涂、浸涂、幕流涂布、喷涂或狭缝涂布等全表面涂布装置或丝网印刷、辊涂、微凹版涂布或喷墨等印刷装置。
涂布后,根据需要,可使用烤盘、烤箱等加热装置进行加热(预焙)。预焙优选在50〜150℃的温度范围下进行30秒〜30分钟,作为预焙膜。通过进行预焙,可得到膜厚均一性好的膜。预焙后的膜厚优选0.1〜15μm。
光刻胶层的基于光刻的图案化方法没有特别限制,优选使用步进重复投影曝光(stepper)、镜面投影掩模对准器(MPA)、平行光掩膜对准器(PLA)等紫外可见曝光机,通过期望的掩膜进行图案曝光,接着,优选通过使用公知的光刻胶用显影液进行显影而得到图案。
在此,作为图案曝光时所使用的掩膜,适合使用为了得到0.1μm〜10μm的圆点状或者正方形状的光刻胶图案而设计的掩膜。光刻胶图案根据需要也可进行热熔融。通过热熔融,可使光刻胶图案为凸面状。作为热熔融的条件,没有特别限定,优选使用烤盘或者烤箱等加热装置在50℃〜300℃的温度范围下加热30秒〜2小时左右。
可通过对光刻胶图案、和含有聚金属氧烷的固化膜进行全表面干式蚀刻而得到微透镜。干式蚀刻优选使用反应性离子蚀刻装置(RiE装置),以CHF3(三氟甲烷)、CF4(四氟甲烷)、氧气、或它们的混合气体作为处理气体。通过这样的干式蚀刻,可将前述光刻胶图案和含有前述聚金属氧烷的固化膜同时蚀刻,因此将前述含有聚金属氧烷的固化膜加工为微透镜形状。
干式蚀刻后,产生光刻胶图案的干式蚀刻残渣时,根据需要可进行光刻胶的去除。去除方法没有特别限制,可列举处理气体使用氧气的灰化、浸渍于市售的蚀刻剥离液的方法。
(有机EL用途)
由本发明的聚金属氧烷得到的固化膜适合用作有机EL元件、有机EL照明用途。更具体而言,可列举在有机EL元件或者有机EL照明中使用的透明导电膜的上部或下部形成的绝缘层薄膜。
现在,有机EL为表面发光的新光源,期待在下一代的显示器、照明中的应用。有机EL为在电极间具有发光层、控制载流子的注入性、传输性的层等有机层的构成。有机EL存在光取出效率、即产生的光发出至设备的外部的效率低的问题。即,课题在于:由于有机层的折射率、和透明电极的折射率大,因此传播至折射率低的基板(n〜1.5)、空气(n〜1.0)时,大部分的光在界面发生全反射,取出效率降低。
因此,通过将由本发明的聚金属氧烷得到的固化膜设置于透明电极的上部、或下部,可控制在固化膜的上部界面和下界面的反射光的相位和强度,可抑制透明电极的上部界面、或下部界面的反射,大幅改善光取出效率。
(建材用途)
本发明的金属氧烷通过涂布并固化,可得到金属氧化膜,因此可用于建材。更具体而言,可列举阻燃材料、亲水性赋予材料。作为阻燃剂,本发明的聚金属氧烷成为不燃层,因此因其燃烧的阻断效果,可赋予阻燃性。此外,通过在建材表面涂布本发明的聚金属氧烷,可形成亲水性高的膜,因此可期待防污效果。
(放射性核素发生器用途)
本发明的聚金属氧烷可用于放射性核素发生器用途。具体而言,为具备填充有本发明的聚金属氧烷的柱的放射性核素发生器。
现在,在医疗领域中,放射性核种被用作放射性诊断药和放射性治疗药。特别是作为放射性诊断药的放射性核种即99mTc(锝−99m、半衰期6.01小时)最多被使用。
99mTc是利用亲核种即99Mo(钼−99、半衰期65.9小时)的β衰变而制造的。即,将包含利用核分裂法或者放射化法生成的99Mo的MoO3颗粒形成钼酸钠水溶液,将该水溶液通过填充有吸附材料的柱,由此吸附材料捕获Mo。捕获的Mo中,仅98Mo产生β衰变,形成98mTc。在该状态下使水通过柱,由此可选择性地取出98mTc。
99Mo的制造方法中的核分裂法是通过对浓缩铀中的235U(铀−235)照射中子而发生核分裂反应,经过复杂的工序,取出99Mo的方法。但是,本方法中,具有产生大量放射性废弃物的缺点。另一方面,放射化法中,是对天然存在的98Mo(钼−98)照射中子而制造99Mo的方法。在该放射化法中,有不产生放射性废弃物的优点,但具有生成的99Mo的比放射能低的问题。因此,要求吸附能高吸附材料和柱。
作为吸附性能高的吸附材料,已开发无机高分子氯化锆化合物。但是,本化合物中,使钼酸钠水溶液通过柱时,化合物末端的氯基发生水解,生成氯化氢。该氯化氢为腐食性气体,因此具有安全性问题。因此,要求不产生氯化氢且吸附性能高的吸附材料。
本发明的聚金属氧烷由于在末端具有(R3 3SiO−)基和或羟基,其成为Mo的吸附位点。因此,与上述无机高分子锆氯化锆同样地,具有高吸附性能,但不产生氯化氢等腐食性气体,因此可适合用作高吸附性能和安全性高的吸附材料。
通过将填充有本发明的聚金属氧烷的柱用作放射性核素发生器,利用高吸附能,可高效率地制造98mTc,因此可将装置进行小型轻量化。
实施例
以下列举合成例、实施例,更具体地说明本发明,但本发明不受这些实施例限定。
各合成例中,基于傅里叶变换型红外分光(以下简写为FT−IR)的分析利用以下方法进行。首先,使用傅里叶变换型红外分光计(岛津制作所制FT720),测定2片层叠的硅晶片,将其作为基线。接着,将1滴金属化合物或者其溶液滴在硅晶片上,将其用另一硅晶片夹持,将其作为测定试样。由测定试样的吸光度、与基线的吸光度的差,算出化合物或者其溶液的吸光度,读取吸收峰。
(合成例1)钛化合物(T1)的合成
向容量500ml的三口烧瓶加入四丁氧基钛34.0g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三甲基硅醇9.0g(0.1mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色液体的钛化合物(T1)。
利用FT−IR分析该钛化合物(T1)时,由于生成Ti−O−Si的吸收峰(958cm-1),不存在硅醇的吸收(883cm-1),因此确认所得钛化合物(T1)为三丁氧基(三甲基甲硅烷氧基)钛。
(合成例2)钛化合物(T2)的合成
向容量500ml的三口烧瓶加入四异丙氧基钛28.4g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三甲基硅醇9.0g(0.1mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的异丙醇,由此得到无色液体的钛化合物(T2)。
利用FT−IR分析该钛化合物(T2)时,由于生成Ti−O−Si的吸收峰(958cm-1),不存在硅醇的吸收(883cm-1),因此确认所得钛化合物(T2)为三异丙氧基(三甲基甲硅烷氧基)钛。
(合成例3)钛化合物(T3)的合成
向容量500ml的三口烧瓶加入四叔丁氧基钛34.0g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三甲基硅醇9.0g(0.1mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的叔丁醇,由此得到无色液体的钛化合物(T3)。
利用FT−IR分析该钛化合物(T3)时,由于生成Ti−O−Si的吸收峰(958cm-1),不存在硅醇的吸收(883cm-1),因此确认所得钛化合物(T3)为三叔丁氧基(三甲基甲硅烷氧基)钛。
(合成例4)钛化合物(T4)的合成
向容量500ml的三口烧瓶加入四丁氧基钛34.0g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三乙基硅醇13.3g(0.1mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色液体的钛化合物(T4)。
利用FT−IR分析该钛化合物(T4)时,由于生成Ti−O−Si的吸收峰(958cm-1),不存在硅醇的吸收(883cm-1),因此确认所得钛化合物(T4)为三丁氧基(三乙基甲硅烷氧基)钛。
(合成例5)钛化合物(T5)的合成
向容量500ml的三口烧瓶加入四丁氧基钛34.0g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三甲基硅醇18.0g(0.2mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色液体的钛化合物(T5)。
利用FT−IR分析该钛化合物(T5)时,确认生成Ti−O−Si的吸收峰(958cm-1),且不存在硅醇的吸收(883cm-1)。此外,Ti−O−Si的吸收峰强度与钛化合物(T1)相比较,达到2倍,因此确认所得钛化合物(T5)为二丁氧基双(三甲基甲硅烷氧基)钛。
(合成例6)钛化合物(T6)的合成
向容量500ml的三口烧瓶加入四丁氧基钛34.0g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三甲基硅醇27.1g(0.3mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色液体的钛化合物(T6)。
利用FT−IR分析该钛化合物(T6)时,确认生成Ti−O−Si的吸收峰(958cm-1),且不存在硅醇的吸收(883cm-1)。此外,Ti−O−Si的吸收峰强度与钛化合物(T1)相比较,达到3倍,因此确认所得钛化合物(T6)为丁氧基三(三甲基甲硅烷氧基)钛)。
(合成例7)锆化合物(Z1)的合成
向容量500ml的三口烧瓶加入四丁氧基锆38.4g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三甲基硅醇9.0g(0.1mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色液体的锆化合物(Z1)。
利用FT−IR分析该锆化合物(Z1)时,由于生成Zr−O−Si的吸收峰(968cm-1),不存在硅醇的吸收(883cm-1),因此确认所得锆化合物(Z1)为三丁氧基(三甲基甲硅烷氧基)锆。
(合成例8)锆化合物(Z2)的合成
向容量500ml的三口烧瓶加入四丙氧基锆32.8g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三甲基硅醇9.0g(0.1mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丙醇,由此得到无色液体的锆化合物(Z2)。
利用FT−IR分析该锆化合物(Z2)时,由于生成Zr−O−Si的吸收峰(968cm-1),不存在硅醇的吸收(883cm-1),因此确认所得锆化合物(Z2)为三丙氧基(三甲基甲硅烷氧基)锆。
(合成例9)锆化合物(Z3)的合成
向容量500ml的三口烧瓶加入四丁氧基锆38.4g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三乙基硅醇18.0g(0.1mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色液体的锆化合物(Z3)。
利用FT−IR分析该锆化合物(Z3)时,由于生成Zr−O−Si的吸收峰(968cm−1),不存在硅醇的吸收(883cm−1),因此确认所得锆化合物(Z3)为三丁氧基(三乙基甲硅烷氧基)锆。
(合成例10)锆化合物(Z4)的合成
向容量500ml的三口烧瓶加入四丁氧基锆38.4g(0.1mol),将烧瓶浸于40℃的油浴搅拌30分钟。然后,使用滴液漏斗花费1小时添加三甲基硅醇18.0g(0.2mol),添加后再搅拌1小时。将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色液体的锆化合物(Z4)。
利用FT−IR分析该锆化合物(Z4),确认Zr−O−Si的吸收峰(968cm-1)的生成、及不存在硅醇的吸收峰(883cm-1)。此外,Zr−O−Si的吸收峰强度与锆化合物(Z3)相比,达到2倍,因此确认所得锆化合物(Z4)为二丁氧基双(三甲基甲硅烷氧基)锆。
关于合成例1〜10,总结记载于表1。
[表1]
(合成例11)钛化合物(T1−H1)溶液
向容量500ml的三口烧瓶加入钛化合物(T1)35.6g(0.1mol)、和作为溶剂的丙二醇单甲基醚乙酸酯(以下简写为PGMEA)50.0g,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充水1.8g(0.1mol),花费1小时添加至烧瓶内。在水的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时。
将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色透明的钛化合物(T1−H1)溶液。利用FT−IR分析所得钛化合物(T1−H1)溶液时,可确认Ti−O−Si的吸收峰(958cm-1)和Ti−OH的吸收峰(1645cm-1和3380cm-1),因此推定钛化合物(T1−H1)为二丁氧基(羟基)(三甲基甲硅烷氧基)钛。
这些结果记载于表2。
(合成例12〜合成例25、比较合成例1〜比较合成例3)
向容量500ml的三口烧瓶加入表2所示的钛化合物和溶剂,与合成例11同样地搅拌。然后,与合成例11同样地添加表2所示的量的水,进行水解。水的添加中的烧瓶内容液外观示于表2。此外,与合成例11同样地减压馏去作为副产物的醇,利用FT−IR分析的结果示于表2。
关于比较合成例1〜3,添加水时,瞬间产生白色的析出。认为这是钛烷氧化物的水解速度大而生成了四羟基钛。因此,推定生成的四羟基钛发生凝集,不溶于溶剂。
[表2]
(合成例26)锆化合物(Z1−H1)溶液
向容量500ml的三口烧瓶加入锆化合物(Z1)40.0g(0.1mol)、和作为溶剂的PGMEA50.0g,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充水1.8g(0.1mol),花费1小时添加至烧瓶内。在水的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时。
将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到无色透明的锆化合物(Z1−H1)溶液。利用FT−IR分析所得锆化合物(Z1−H1)溶液时,可确认Zr−O−Si的吸收峰(968cm-1)和Zr−OH的吸收峰(1600cm-1和3410cm-1),因此推定锆化合物(Z1−H1)为二丁氧基(羟基)(三甲基甲硅烷氧基)锆。
这些结果记载于表3。
(合成例27〜合成例36、比较合成例4〜比较合成例5)
向容量500ml的三口烧瓶加入表3所示的钛化合物和溶剂,与合成例26同样地搅拌。然后,与合成例26同样地添加表3所示的量的水,进行水解。水的添加中的烧瓶内容液外观示于表3。此外,与合成例26同样地减压馏去作为副产物的醇,利用FT−IR分析的结果示于表3。
关于比较合成例4和5,添加水时,瞬间产生白色的析出。认为这是锆烷氧化物的水解速度大而生成了四羟基锆。因此,推定生成的四羟基锆发生凝集,不溶于溶剂。
[表3]
以下各实施例中,聚金属氧烷溶液的固体成分浓度通过以下方法求出:在铝杯称取聚金属氧烷溶液1.0g,使用烤盘在250℃下加热30分钟,使液体成分蒸发,通过称量加热后的铝杯中残留的固体成分而求出。
基于FT−IR的分析利用以下方法进行。首先,使用傅里叶变换型红外分光计(岛津制作所制FT720),仅测定硅晶片,将其作为基线。接着,将聚金属氧烷溶液滴在硅晶片上,接着,以任意的转速进行旋涂,然后,通过真空干燥来制作测定试样。由测定试样的吸光度、与基线的吸光度的差算出聚金属氧烷的吸光度,读取吸收峰。
重均分子量(Mw)利用以下方法求出。作为展开溶剂,使氯化锂溶于N−甲基−2−吡咯烷酮,制作0.02M氯化锂N−甲基−2−吡咯烷酮溶液。使聚金属氧烷溶于展开溶剂,以达到0.2wt%,将其作为试样溶液。将展开溶剂以流速0.5mL/min填充于多孔质凝胶柱(东ソー制TSKgel α−M、α−3000各1根),向其中注入试样溶液0.2mL。利用差示折射率检测器(昭和电工制RI−201型)检测柱溶出物,通过解析溶出时间来求出重均分子量(Mw)。
实施例1 聚金属氧烷(TP−1)的合成
混合钛化合物(T1)35.6g(0.1mol)、和作为溶剂的丙二醇单甲基醚乙酸酯(以下简写为PGMEA)50.0g,将其作为溶液1。此外,混合水1.8g(0.1mol)、作为水稀释溶剂的异丙醇(以下简写为IPA)50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−1)溶液。
利用FT−IR分析聚金属氧烷(TP−1)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−1)的重均分子量(Mw)以聚苯乙烯换算为6000。
实施例2 聚金属氧烷(TP−2)的合成
混合钛化合物(T1)35.6g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水3.6g(0.2mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−2)溶液。
利用FT−IR分析聚金属氧烷(TP−2)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−2)的重均分子量(Mw)以聚苯乙烯换算为21000。
实施例3 聚金属氧烷(TP−3)的合成
混合钛化合物(T1)35.6g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水3.6g(0.2mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的二异丁基胺1.3g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−3)溶液。
利用FT−IR分析聚金属氧烷(TP−3)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−3)的重均分子量(Mw)以聚苯乙烯换算为25000。
实施例4 聚金属氧烷(TP−4)的合成
混合钛化合物(T1)35.6g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水3.6g(0.2mol)、和作为水稀释溶剂的IPA50.0g,将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−4)溶液。
利用FT−IR分析聚金属氧烷(TP−4)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−4)的重均分子量(Mw)以聚苯乙烯换算为6000。
实施例5 聚金属氧烷(TP−5)的合成
混合钛化合物(T1)35.6g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水5.4g(0.3mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−5)溶液。
利用FT−IR分析聚金属氧烷(TP−5)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−5)的重均分子量(Mw)以聚苯乙烯换算为44000。
实施例6 聚金属氧烷(TP−6)的合成
混合钛化合物(T1)35.6g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水5.4g(0.3mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的二异丁基胺1.3g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−6)溶液。
利用FT−IR分析聚金属氧烷(TP−6)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−6)的重均分子量(Mw)以聚苯乙烯换算为25000。
实施例7 聚金属氧烷(TP−7)的合成
混合钛化合物(T2)31.4g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水5.4g(0.3mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−7)溶液。
利用FT−IR分析聚金属氧烷(TP−7)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−7)的重均分子量(Mw)以聚苯乙烯换算为46000。
实施例8 聚金属氧烷(TP−8)的合成
混合钛化合物(T4)39.8g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水5.4g(0.3mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−8)溶液。
利用FT−IR分析聚金属氧烷(TP−8)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−8)的重均分子量(Mw)以聚苯乙烯换算为28000。
实施例9 聚金属氧烷(TP−9)的合成
混合钛化合物(T5)37.2g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水3.6g(0.2mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−9)溶液。
利用FT−IR分析聚金属氧烷(TP−9)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−9)的重均分子量(Mw)以聚苯乙烯换算为18000。
实施例10 聚金属氧烷(TP−10)的合成
称量钛化合物(T2−H3)溶液68.81g(由三羟基(三甲基甲硅烷氧基)钛为18.81g(0.1mol)、PGMEA50.0g构成),将其作为溶液1。此外,混合作为稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA和作为副产物的水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−10)溶液。
利用FT−IR分析聚金属氧烷(TP−10)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−10)的重均分子量(Mw)以聚苯乙烯换算为48000。
实施例11 聚金属氧烷(TP−11)的合成
称量钛化合物(T2−H2)溶液73.02g(由(异丙氧基)(二羟基)(三甲基甲硅烷氧基)钛为18.81g(0.1mol)、PGMEA50.0g构成),将其作为溶液1。此外,混合水1.8g(0.1mol)、作为稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA和水が留出した。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(TP−11)溶液。
利用FT−IR分析聚金属氧烷(TP−11)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−11)的重均分子量(Mw)以聚苯乙烯换算为47000。
实施例12 聚金属氧烷(TP−12)的合成
将作为实施例7的溶剂的PGMEA改变为1,2−二乙氧基乙烷,除此以外,与实施例7同样地进行合成、及固体成分调整,得到聚金属氧烷(TP−12)溶液。所得聚金属氧烷(TP−12)溶液的外观为淡黄色透明。
利用FT−IR分析聚金属氧烷(TP−12)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−12)的重均分子量(Mw)以聚苯乙烯换算为49000。
实施例13 聚金属氧烷(TP−13)的合成
将作为实施例7的溶剂的PGMEA改变为2,6−二甲基−4−庚酮,除此以外,与实施例7同样地进行合成、及固体成分调整,得到聚金属氧烷(TP−13)。所得聚金属氧烷(TP−13溶液的外观为淡黄色透明。
利用FT−IR分析聚金属氧烷(TP−13)溶液时,可确认Ti−O−Si的吸收峰(958cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(TP−13)的重均分子量(Mw)以聚苯乙烯换算为46000。
实施例14 聚金属氧烷(ZP−1)的合成
混合锆化合物(Z−1)40.0g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水5.4g(0.3mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(ZP−1)溶液。
利用FT−IR分析聚金属氧烷(ZP−1)溶液时,可确认Zr−O−Si的吸收峰(968cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(ZP−1)的重均分子量(Mw)以聚苯乙烯换算为45000。
实施例15 聚金属氧烷(ZP−2)的合成
混合锆化合物(Z−4)41.6g(0.1mol)、和作为溶剂的PGMEA50.0g,将其作为溶液1。此外,混合水3.6g(0.2mol)、作为水稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出作为副产物的丁醇和水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(ZP−2)溶液。
利用FT−IR分析聚金属氧烷(ZP−2)溶液时,可确认Zr−O−Si的吸收峰(968cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(ZP−2)的重均分子量(Mw)以聚苯乙烯换算为19000。
实施例16 聚金属氧烷(ZP−3)的合成
称量锆化合物(Z1−H3)溶液73.1g(由三羟基(三甲基甲硅烷氧基)锆g(0.1mol)、PGMEA50.0g构成),将其作为溶液1。此外,混合作为稀释溶剂的IPA50.0g、和作为聚合催化剂的三丁基胺2.2g(0.01mol),将其作为溶液2。
向容量500ml的三口烧瓶中加入溶液1的全部量,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的,向滴液漏斗填充溶液2的全部量,花费1小时添加至烧瓶内。在溶液2的添加中,烧瓶内容液不发生析出,为均一的无色透明溶液。添加后再搅拌1小时,得到含羟基的金属化合物。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出IPA、作为副产物的水。加热搅拌中,烧瓶内容液不发生析出,为均一的透明溶液。
加热结束后,将烧瓶内容液冷却至室温,得到聚金属氧烷溶液。所得聚金属氧烷溶液的外观为淡黄色透明。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,作为聚金属氧烷(ZP−3)溶液。
利用FT−IR分析聚金属氧烷(ZP−3)溶液时,可确认Zr−O−Si的吸收峰(968cm-1),因此确认为具有三甲基甲硅烷氧基的聚金属氧烷。
聚金属氧烷(ZP−3)的重均分子量(Mw)以聚苯乙烯换算为46000。
关于实施例1〜16,总结记载于表4。
[表4]
(比较合成例6) 聚金属氧烷(TP−14)的合成
向容量500ml的三口烧瓶加入四丁氧基钛34.0g(0.1mol),将烧瓶浸于75℃的油浴搅拌30分钟(内温为70℃)。然后,以水解为目的用滴液漏斗花费1小时添加水3.1g(0.17mol)和丁醇50g的混合溶液。添加中,然后,升温至90℃保持搅拌1小时,使反应熟化。
将烧瓶内容物转移至200ml茄型烧瓶,减压馏去生成的丁醇,由此得到白色固体的聚金属氧烷(TP−10)。
聚金属氧烷(TP−14)不溶于PGMEA,因此溶于四氢呋喃,进行调整以使固体成分浓度达到20wt%。
聚金属氧烷(TP−14)的重均分子量(Mw)以聚苯乙烯换算为1700。
(比较合成例7) 聚金属氧烷(TP−15)的合成
向容量500ml的三口烧瓶加入四丁氧基钛34.0g(0.1mol)、和作为溶剂的100g乙醇,将烧瓶浸于40℃的油浴搅拌30分钟。然后,以水解为目的将水2.7g(0.15mol)和叔丁基肼盐酸盐0.25g(0.002摩尔)和乙醇50g的混合溶液填充至滴液漏斗,花费1小时添加至烧瓶内。添加后,加入PGMEA50g,再搅拌1小时。然后,以缩聚为目的,花费30分钟将油浴升温至140℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜130℃)。反应中,馏出作为副产物的丁醇和水。
求出所得聚金属氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,得到聚金属氧烷(TP−15)溶液。
聚金属氧烷(TP−15)的重均分子量(Mw)以聚苯乙烯换算为8000。
(比较合成例8) 聚硅氧烷(SP−1)的合成
向容量500ml的三口烧瓶加入2−蒽基三甲氧基硅烷20.9g(0.07mol)、4−羟基苄基三甲氧基硅烷6.8g(0.03mol)和作为溶剂的PGMEA50.0g,搅拌的同时,以水解为目的用滴液漏斗花费1小时添加水5.4g(0.3mol)和磷酸0.2g的混合溶液。然后,将烧瓶浸于40℃的油浴搅拌60分钟后,将油浴花费30分钟升温至120℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜110℃)。反应中馏出作为副产物的甲醇、水。
求出所得聚硅氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,得到聚硅氧烷(SP−1)溶液。所得聚硅氧烷(SP−01)的重均分子量(Mw)以聚苯乙烯换算为3000。
(比较合成例9) 含有金属化合物颗粒的聚硅氧烷(SP−2)的合成
向容量500ml的三口烧瓶加入甲基三甲氧基硅烷4.1g(0.03mol)、苯基三甲氧基硅烷13.9g(0.07mol)、数均颗粒系15nm的“オプトレイクTR−527”(商品名、催化剂化成工业(株)制 组成:氧化钛颗粒20重量%、甲醇80重量%)315g、和作为溶剂的PGMEA50.0g,搅拌的同时,以水解为目的用滴液漏斗花费1小时添加水5.4g(0.3mol)和磷酸0.2g的混合溶液。然后,将烧瓶浸于40℃的油浴搅拌60分钟后,将油浴花费30分钟升温至120℃。升温开始1小时后,溶液的内温达到100℃,自此再加热搅拌2小时(内温为100〜110℃)。反应中馏出作为副产物的甲醇、水。
求出所得含有金属化合物颗粒的聚硅氧烷溶液的固体成分浓度,然后加入PGMEA,以使固体成分浓度达到20wt%,得到含有金属化合物颗粒的聚硅氧烷(SP−2)溶液。
实施例17
(1)固化膜的制作
使用各自旋转涂布机(ミカサ(株)制1H−360S)将聚金属氧烷(TP−1)溶液旋涂于4寸硅晶片和Tempax玻璃板上后,使用烤盘(大日本スクリ−ン制造(株)制SCW−636)在100℃下加热3分钟,制作预焙膜。然后,使用烤盘在300℃下固化5分钟制作膜厚0.3μm和0.5μm的固化膜。应予说明,使用光干渉式膜厚计(大日本スクリ−ン制造(株)制ラムダエ−スSTM602)测定膜厚。
(2)固化膜的耐裂纹性评价
对于(1)中所得固化膜的耐裂纹性用下述5级进行评价。4以上为合格。
5 : 光学显微镜观察(倍率:5倍)中未发现裂纹
4 : 光学显微镜观察(倍率:5倍)中发现略微裂纹
3 : 光学显微镜观察(倍率:5倍)中发现明显裂纹
2 : 通常肉眼可见略微裂纹
1 : 通常肉眼可见明显裂纹。
(3)固化膜的折射率测定
对于(1)中硅晶片上制作的膜厚0.3μm的固化膜,测定时的温度为22℃,使用光谱椭偏仪(大塚电子(株)制FE5000)测定来自固化膜的反射光的偏光状态变化,得到与入射光的相位差和振幅反射率的光谱。通过拟合计算模型的介电函数以接近所得光谱,得到折射率光谱。由折射率光谱读取波长550nm下的折射率值,由此得到固化膜的折射率。
(4)固化膜的透光率测定
使用分光光度计(岛津制作所制MultiSpec−1500),测定Tempax玻璃板的紫外可见吸收光谱,将其作为参照。接着,测定(1)中Tempax玻璃板上制作的膜厚0.3μm的固化膜的紫外可见吸收光谱,通过与参照的差异,算出固化膜的紫外可见吸收光谱。使用所得紫外可见吸收光谱和膜厚,算出固化膜的波长400nm下的每1μm膜厚的透光率。
这些结果示于表5。
实施例18〜32、比较例1〜4
针对表5所示的溶液,与实施例17同样地进行(1)固化膜的制作、(2)固化膜的耐裂纹性评价、(3)固化膜的折射率测定、(4)固化膜的透过率测定。评价结果示于表5。
关于比较例1和比较例2,制作固化膜时,可见裂纹的发生,不能得到均质的膜。认为这是因为大量残存烷氧基的聚金属氧烷,在涂膜形成时因空气中的水分而发生烷氧基的水解,发生脱离,因此收缩应力变大,产生裂纹。
实施例33
混合聚金属氧烷(TP−5)溶液3.5g(固体成分重量0.7g)和氧化硅−氧化钛复合颗粒即 “オプトレイクTR−513”(商品名、催化剂化成工业(株)制、固体成分浓度30%γ−丁内酯分散液)1.0g(固体成分重量0.3g),制备组合物1。与实施例17同样地进行(1)固化膜的制作、(2)固化膜的耐裂纹性评价、(3)固化膜的折射率测定、(4)固化膜的透过率测定。评价结果示于表5。
[表5]
实施例34
制作具有在透明基底基材的上表面层叠有透明导电膜(I)、聚金属氧烷固化膜(II)、氧化硅薄膜(III)和/或透明粘接薄膜(IV)的部位的构件,进行(5)透明导电膜可见性评价。
(5)透明导电膜可见性评价
(5a)构件的制作
(5a−1)透明导电膜图案的制作
在作为透明基底基材的厚度1.1mm的化学强化玻璃基板上,以形成透明导电膜(I)的ITO作为目标进行溅射,形成膜厚50nm的ITO。接着,使用旋转涂布机(1H−360S;ミカサ(株)制)在透明导电膜(I)上旋涂正型光刻胶(OFPR−800;东京応化工业(株)制)后,使用烤盘(SCW−636;大日本スクリーン制造(株)制)在100℃下加热2分钟,形成预焙膜。使用PLA以超高压水银灯作为光源,通过掩膜用100μm的间隙对所得光刻胶的预焙膜进行1000J/m2曝光。然后,使用自动显影装置(AD−2000;滝沢産业(株)制),用2.38wt%氢氧化四甲基铵(以下简写为TMAH)水溶液进行90秒钟淋浴显影,接着,用水漂洗30秒钟,进行光刻胶的图案加工。然后,用HCl−HNO3系的蚀刻液蚀刻ITO,用剥离液去除光刻胶,制作具有第一电极和与其垂直的第二电极的一部分被图案加工的ITO(图1和图2的符号2)的基板(相当于图1的a)。
(5a−2)透明绝缘膜的制作
在(5a−1)中得到的基板上旋涂负型感光性树脂组合物NS−E2000(东レ(株)制)后,使用烤盘在90℃加热2分钟,制作预焙膜。通过掩膜用100μm的间隙对所得预焙膜进行2000J/m2曝光。然后,用0.4wt%TMAH水溶液进行90秒钟淋浴显影,接着,用水漂洗30秒钟。接着,在空气中在230℃下进行1小时固化,制作膜厚1.5μm的透明绝缘膜(图1和图2的符号3)(相当于图1的b)。
(5a−3)钼/铝/钼(以下简写为MAM)配线的制作
在(5a−2)所得的基板上,使用钼和铝作为目标,作为蚀刻液使用H3PO4/HNO3/CH3COOH/H2O=65/3/5/27(重量比)混合溶液,除此以外,利用与上述(5a−1)相同的流程制作MAM配线(图1和图2的符号4)(相当于图1的c)。而且MAM的膜厚调整为250nm。
(5a−4)聚金属氧烷固化膜(II)的形成
在(5a−3)所得的基板上,将聚金属氧烷(TP−1)溶液利用喷墨涂布装置进行图案涂布后,使用烤盘在90℃下预焙2分钟。接着,在空气中在230℃下进行固化1小时,制作聚金属氧烷(TP−1)固化膜(II)(图2的符号5)。
(5a−5)氧化硅薄膜(III)的形成
使用高速等离子体CVD成膜装置(PD−270STL;サムコ(株)制),以四乙氧基硅烷作为原料形成氧化硅薄膜(III)(图2的符号6)。此时,以氧化硅薄膜(III)和包含含聚金属氧烷的组合物的薄膜(II)的图案重合的方式实施掩膜成膜。氧化硅薄膜(III)的膜厚为0.5μm。
(5a−6)带透明粘接剂的膜的贴合
在(5a−5)所得的基板上的一部分贴合粘接剂和其反面具备硬涂层的PET膜(HA−116;リンテック(株)制、粘接剂折射率=1.47),以使空气不会被吸入,形成透明粘接层(IV)。
(5b)透明导电膜可见性评价
由(5a−6)中所得的基板的背面侧观察,对透明导电膜的可见性,进行下述10级评价。应予说明,6以上为合格。
10: 白色荧光灯3cm下凝视下完全看不见图案
9 : 白色荧光灯3cm下凝视下看见略微图案。
8 : 白色荧光灯3cm下凝视下看见少许图案。
7 : 白色荧光灯3cm下凝视下看见明显图案。
6 : 白色荧光灯3cm下通常肉眼可见略微图案。
5 : 白色荧光灯3cm下通常肉眼可见少许图案。
4 : 白色荧光灯3cm下通常肉眼可见明显图案。
3 : 室内灯下通常肉眼可见略微图案。
2 : 室内灯下通常肉眼可见少许图案。
1 : 室内灯下通常肉眼可见明显图案。
(6)基底金属腐蚀性评价
在作为基底金属在全表面具备MAM的玻璃上利用上述(5a−4)记载的方法形成聚金属氧烷固化膜(II),接着,利用上述(5a−5)记载的方法形成氧化硅薄膜(III)。接着,置于温度121℃、湿度100%、气压=2atm的烤箱(HAST CHAMBERE EHS−221MD;エスペック株式会公司制)内,进行试验(プレッシャークッカークッカーテスト、PCT试验)20小时后,利用肉眼观察,用下述11级对固化膜下的MAM因腐蚀而变色的缺陷的占有面积比例进行评价。7以上为合格。
10:固化膜下的MAM的变色面积比例为0%。固化膜本身没有外观变化。
9:固化膜下的MAM的变色面积比例为1〜3%。固化膜本身没有外观变化。
8:固化膜下的MAM的变色面积比例为4〜6%。固化膜本身没有外观变化。
7:固化膜下的MAM的变色面积比例为7〜9%。固化膜本身没有外观变化。
6:固化膜下的MAM的变色面积比例为10〜15%。固化膜本身没有外观变化。
5:固化膜下的MAM的变色面积比例为16〜20%。固化膜本身没有外观变化。
4:固化膜下的MAM的变色面积比例为21〜30%。固化膜本身没有外观变化。
3:固化膜下的MAM的变色面积比例为31〜50%。固化膜本身没有外观变化。
2:固化膜下的MAM的变色面积比例为51〜70%。固化膜本身没有外观变化。
1:固化膜下的MAM的变色面积比例为71〜100%。固化膜本身没有外观变化。
0:固化膜下的MAM的变色面积比例为100%。而且,固化膜本身发生变色、裂纹等。
实施例35〜49、比较例5〜8
以表6所示的构成利用与实施例34相同的方法,进行(5)透明导电膜可见性评价、和(6)基底金属评价。评价结果示于表6。
实施例50
(5a−3)聚金属氧烷固化膜(II)形成中,代替聚金属氧烷(TP−1)溶液,使用实施例33中制备的组合物1,除此以外,利用于实施例34相同的方法进行(5)透明导电膜可见性评价、和(6)基底金属评价。评价结果示于表6。
实施例51
不进行形成(5a−5)氧化硅薄膜(III)的工序,除此以外,利用与实施例40相同的方法,进行(5)透明导电膜可见性评价、和(6)基底金属评价。评价结果示于表6。
实施例52
不进行贴合带(5a−6)透明粘接剂的膜的工序,除此以外,利用与实施例40相同的方法,进行(5)透明导电膜可见性评价、和(6)基底金属评价。评价结果示于表6。
实施例53
(5a−1)透明导电膜图案的制作中,代替化学强化玻璃基板,使用厚度0.2mm的聚对苯二甲酸乙二醇酯(以下简写为PET)基材,除此以外,利用与实施例40相同的方法,进行(5)透明导电膜可见性评价。评价结果示于表6。
比较例9
不进行形成(5a−4)聚金属氧烷固化膜(II)的工序,除此以外,利用与实施例40相同的方法,进行(5)透明导电膜可见性评价、和(6)基底金属评价。评价结果示于表6。
[表6]
实施例54
进行基板上制作的聚金属氧烷固化膜的干式蚀刻,测定干式蚀刻后的表面粗糙度Ra和透光率。详细如下所述。测定结果示于表6。
(6−1)固化膜的制作
各自使用旋转涂布机(ミカサ(株)制1H−360S)将聚金属氧烷(TP−05)溶液旋涂于6寸硅晶片和Tempax玻璃板后,使用烤盘(大日本スクリーン制造(株)制SCW−636)在100℃下加热3分钟,制作预焙膜。然后,使用烤盘在300℃下固化5分钟制作膜厚0.5μm的固化膜。应予说明,膜厚使用光干渉式膜厚计(大日本スクリーン制造(株)制ラムダエースSTM602)进行测定。
(6−2)折射率测定
对于在硅晶片上制作的固化膜,测定时的温度为22℃,使用光谱椭偏仪(大塚电子(株)制FE5000)测定来自固化膜的反射光的偏光状态变化,得到与入射光的相位差和振幅反射率的光谱。通过拟合计算模型的介电函数以接近所得光谱,得到折射率光谱。由折射率光谱读取波长550nm下的折射率值,由此得到固化膜的折射率。
(6−3)固化膜的透光率测定
使用分光光度计(島津制作所制MultiSpec−1500),测定Tempax玻璃板的紫外可见吸收光谱,将其作为参照。接着,测定在Tempax玻璃板上制作的固化膜的紫外可见吸收光谱,通过与参照的差异,算出固化膜的紫外可见吸收光谱。使用所得紫外可见吸收光谱和膜厚,算出固化膜的波长400nm下的每1μm膜厚的透光率。
(6−4)干式蚀刻
使用反应性离子蚀刻装置(サムコ(株)制RIE−10N),对在Tempax玻璃板上制作的固化膜进行使用CF4(4氟甲烷)和氧气的混合气体作为处理气体的干式蚀刻。应予说明,干式蚀刻条件为:气体混合比为CF4:氧气=80:20,气体流量为50sccm、输出功率199W、内压为10Pa、处理时间为2min。
(6−5)干式蚀刻后的表面粗糙度测定
利用扫描型探针显微镜(Bruker Corporation制Dimension Icon)扫描干式蚀刻处理后的固化膜表面,得到固化膜表面的3维立体图像。切断所得图像,得到固化膜截面的轮廓曲线。基于JIS B 0601:2013计算所得轮廓曲线,由此得出算术平均粗糙度Ra。
(6−6)干式蚀刻后的透光率测定
使用分光光度计(島津制作所制MultiSpec−1500),测定Tempax玻璃板的紫外可见吸收光谱,将其作为参照。接着,测定在Tempax玻璃板上制作的干式蚀刻处理后的固化膜的紫外可见吸收光谱,通过与参照的差异,算出干式蚀刻处理后的固化膜的紫外可见吸收光谱。使用所得紫外可见吸收光谱和膜厚,算出干式蚀刻处理后的固化膜的波长400nm下的每1μm膜厚的透光率。
这些结果示于表7。
实施例55〜65、比较例10〜11
对于表7所示的溶液,与实施例54同样地进行(6−1)固化膜的制作、(6−2)折射率的测定、(6−3)固化膜的透光率的测定、(6−4)干式蚀刻、(6−5)干式蚀刻后的表面粗糙度测定。进行(6−6)干式蚀刻后的透光率测定。评价结果示于表7。
[表7]
比较例10是使用聚硅氧烷(SP−1)溶液制作固化膜的比较例。聚硅氧烷(SP−1)具有折射率高的蒽基,因此可实现折射率高达1.63的折射率。但是,由于来自蒽基,在可见光领域具有吸收,因此透过率达到85%且不能得到微透镜所要求的高透明性。
比较例11是使用含金属化合物颗粒的聚硅氧烷(SP−2)溶液来制作固化膜的比较例。由于使用折射率高的氧化钛颗粒,因此可实现达到1.75、非常高的折射率。但是,在干式蚀刻时,因氧化钛颗粒和聚硅氧烷成分与蚀刻气体的反应性各自不同,因此干式蚀刻速度局部地产生差异。因此,固化膜的表面粗糙,算术平均粗糙度Ra为50nm。此外,由于固化膜的表面粗糙,光发生散射,因此干式蚀刻后的透过率达到80%,不能得到微透镜所要求的高透明性。
实施例66
使用旋转涂布机(ミカサ(株)制1H−360S)将聚金属氧烷溶液(TP−7)旋涂于6寸硅晶片后,使用烤盘(大日本スクリーン制造(株)制SCW−636)在100℃下加热3分钟,制作预焙膜。然后,使用烤盘在300℃下固化5分钟来制作含有膜厚0.5μm的聚金属氧烷的固化膜。
然后,在含有聚金属氧烷的固化膜上旋涂正型光刻胶(东京応化工业(株)制OFPR−800)后,使用烤盘在100℃下加热2分钟,形成光刻胶层。然后,使用i线ステッパー((株)ニコン性NSR−i9C),通过掩膜,进行图案曝光。应予说明,作为掩膜,使用为了得到2μm的圆点状的图案而设计的掩膜。
然后,使用自动显影装置(滝沢产业(株)制AD−2000),作为显影液使用2.38wt%氢氧化四铵水溶液,进行90秒钟淋浴显影,接着,漂洗30秒钟,得到2μm的圆点状的光刻胶图案。然后,使用烤盘在120℃下加热5分钟,使光刻胶图案热熔融。
使用反应性离子蚀刻装置(サムコ(株)制RIE−10N),使用CF4(4氟甲烷)和氧气的混合气体作为处理气体对含有光刻胶图案和聚金属氧烷的固化膜进行全表面干式蚀刻,得到含有聚金属氧烷的微透镜图案。应予说明,干式蚀刻条件为:气体混合比为CF4:氧气=80:20,气体流量为50sccm、输出功率199W、内压为10Pa、处理时间为5min。
使用扫描型电子显微镜(日立ハイテクテクノロジーズ制S−4800)观察所得微透镜图案时,确认为表面不粗糙且光滑的微透镜图案。
此外,微透镜图案的算术平均表面粗糙度利用以下方法求出。利用扫描型探针显微镜(Bruker Corporation制Dimension Icon)扫描微透镜图案的表面,得到3维立体图像。切断所得图像,得到微透镜截面的轮廓曲线。从轮廓曲线中去除微透镜的曲率,得到表面粗糙度曲线。由表面粗糙度曲线基于JIS B 0601:2013进行计算,由此得到算术平均粗糙度Ra。所得微透镜图案的算术平均表面粗糙度Ra为4nm。
1 : 透明基底基板
2 : 透明导电薄膜(I)
3 : 绝缘膜
4 : MAM配线
5 : 由聚金属氧烷或其组合物得到的固化膜(II)
6 : 氧化硅薄膜(III)
7 : 透明粘接层(IV)。
Claims (29)
1.具有下述通式(1)所示的构成单元的聚金属氧烷,
[化1]
R1为羟基、碳原子数1〜12的烷基、碳原子数5〜12的脂环式烷基、碳原子数1〜12的烷氧基、碳原子数6〜30的芳族基、(R3 3SiO−)基、具有硅氧烷键的基团或具有金属氧烷键的基团,R1的至少一个为(R3 3SiO−)基;(R3 3SiO−)基任选自三羟基甲硅烷氧基、三甲基甲硅烷氧基、三乙基甲硅烷氧基、三丙基甲硅烷氧基、三异丙基甲硅烷氧基、三丁基甲硅烷氧基、三异丁基甲硅烷氧基、三仲丁基甲硅烷氧基、三叔丁基甲硅烷氧基、三环己基甲硅烷氧基、三甲氧基甲硅烷氧基、三乙氧基甲硅烷氧基、三丙氧基甲硅烷氧基、三异丙氧基甲硅烷氧基、三丁氧基甲硅烷氧基、三苯基甲硅烷氧基、羟基二苯基甲硅烷氧基、甲基二苯基甲硅烷氧基、乙基二苯基甲硅烷氧基、丙基二苯基甲硅烷氧基、二羟基(苯基)甲硅烷氧基、二甲基(苯基)甲硅烷氧基、二乙基(苯基)甲硅烷氧基、二丙基(苯基)甲硅烷氧基、三萘基甲硅烷氧基、羟基二萘基甲硅烷氧基、甲基二萘基甲硅烷氧基、乙基二萘基甲硅烷氧基、丙基二萘基甲硅烷氧基、二羟基(萘基)甲硅烷氧基、二甲基(萘基)甲硅烷氧基、二乙基(萘基)甲硅烷氧基和二丙基(萘基)甲硅烷氧基;R2任选自氢原子、碳原子数1〜12的烷基、或具有金属氧烷键的基团;R1、R2和R3存在多个时,可以各自相同,也可以不同;M表示选自Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Ga、Ge、Zr、Nb、Mo、Ru、Rh、Pd、Ag、In、Sn、Sb、Hf、Ta、W、Re、Os、Ir、Pt、Au、Tl和Bi的金属原子;m为表示金属原子M的价数的整数,a为1〜(m−2)的整数。
2.根据权利要求1所述的聚金属氧烷,其中,所述聚金属氧烷中的R1的至少一个为羟基。
3.根据权利要求1或2所述的聚金属氧烷,其中,M包含1种以上选自Ti、Zr和Sn中的金属原子。
4.聚金属氧烷的制造方法,其包括使下述通式(2)所示的化合物或其水解物缩聚,得到权利要求1中所述的聚金属氧烷的工序,
[化2]
R4任选自羟基、碳原子数1〜12的烷基、碳原子数5〜12的脂环式烷基、碳原子数1〜12的烷氧基或碳原子数6〜30的芳族基;R5任选自氢原子或碳原子数1〜12的烷基;R4和R5存在多个时,可以各自相同,也可以不同;M表示选自Ti、V、Cr、Mn、Fe、Co、Ni、Cu、Zn、Ga、Ge、Zr、Nb、Mo、Ru、Rh、Pd、Ag、In、Sn、Sb、Hf、Ta、W、Re、Os、Ir、Pt、Au、Tl和Bi中的金属原子;m为表示金属原子M的价数的整数,n为1〜(m−1)的整数。
6.根据权利要求5所述的聚金属氧烷的制造方法,其中,所述通式(3)中的y为2〜(m−1)的整数。
7.根据权利要求4〜6中任一项所述的聚金属氧烷的制造方法,其中,所述通式(2)中的M包含1种以上选自Ti、Zr和Sn中的金属原子。
8.组合物,其包含权利要求1〜3中任一项所述的聚金属氧烷。
9.组合物,其特征在于,包含权利要求1〜3中任一项所述的聚金属氧烷和无机颗粒。
10.根据权利要求9所述的组合物,其中,所述无机颗粒为金属化合物颗粒。
11.权利要求1〜4中任一项所述的聚金属氧烷的固化膜。
12.权利要求8〜10中任一项所述的组合物的固化膜。
13.根据权利要求11或12所述的固化膜,其中,波长400nm下的每1μm膜厚的透光率为90%以上。
14.根据权利要求11或12所述的固化膜,其中,波长550nm下的折射率为1.58〜2.20。
15.固化膜的制造方法,其包括加热权利要求1〜3中任一项所述的聚金属氧烷、或权利要求9〜11中任一项所述的组合物的工序。
16.构件,其具备权利要求11〜14中任一项所述的固化膜。
17.根据权利要求16所述的构件,所述构件具有自透明基底基材的上表面起依次层叠有透明导电薄膜(I)、权利要求11〜14中任一项所述的固化膜(II)的部位。
18.根据权利要求17所述的构件,其中,在权利要求11〜14中任一项所述的固化膜(II)的上表面具有层叠有氧化硅薄膜(III)和/或折射率为1.46〜1.53的透明粘接薄膜(IV)的部位。
19.根据权利要求17或18的构件,其中,所述透明基底基材为玻璃基板或光学膜。
20.根据权利要求16所述的构件,其中,所述构件为透镜。
21.透镜的制造方法,其包括
在基板上形成权利要求11〜14中任一项所述的固化膜的工序、在所述固化膜上形成光刻胶图案的工序、和将所述光刻胶图案和所述固化膜干式蚀刻的工序。
22.电子部件,其具备权利要求16〜20中任一项所述的构件。
23.根据权利要求22的电子部件,其中,所述电子部件为接触式传感器。
24.根据权利要求22的电子部件,其中,所述电子部件为图像传感器。
25.根据权利要求22的电子部件,其中,所述电子部件为有机EL元件。
26.根据权利要求22的电子部件,其中,所述电子部件为有机EL照明。
27.建材,其含有权利要求1〜4中任一项所述的聚金属氧烷。
28.柱,其填充有权利要求1〜4中任一项所述的聚金属氧烷。
29.放射性核素发生器,其具备权利要求28所述的柱。
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- 2016-11-17 KR KR1020187015605A patent/KR102438946B1/ko active IP Right Grant
- 2016-11-17 US US15/772,881 patent/US11795064B2/en active Active
- 2016-11-17 SG SG11201803938RA patent/SG11201803938RA/en unknown
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- 2016-11-17 CN CN201680069004.2A patent/CN108291031B/zh active Active
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- 2016-11-17 EP EP16868460.3A patent/EP3381969B1/en active Active
- 2016-11-24 TW TW105138583A patent/TWI679224B/zh active
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TWI679224B (zh) | 2019-12-11 |
KR102438946B1 (ko) | 2022-09-02 |
EP3381969B1 (en) | 2020-06-03 |
TW201739797A (zh) | 2017-11-16 |
US20180327275A1 (en) | 2018-11-15 |
EP3381969A1 (en) | 2018-10-03 |
US11795064B2 (en) | 2023-10-24 |
WO2017090512A1 (ja) | 2017-06-01 |
CN108291031A (zh) | 2018-07-17 |
JPWO2017090512A1 (ja) | 2018-04-05 |
JP6327366B2 (ja) | 2018-05-23 |
EP3381969A4 (en) | 2019-06-26 |
KR20180086202A (ko) | 2018-07-30 |
SG11201803938RA (en) | 2018-06-28 |
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