CN101501139B - 硅氧烷树脂和硅氧烷组合物 - Google Patents
硅氧烷树脂和硅氧烷组合物 Download PDFInfo
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- CN101501139B CN101501139B CN2007800291096A CN200780029109A CN101501139B CN 101501139 B CN101501139 B CN 101501139B CN 2007800291096 A CN2007800291096 A CN 2007800291096A CN 200780029109 A CN200780029109 A CN 200780029109A CN 101501139 B CN101501139 B CN 101501139B
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- Prior art keywords
- silicone resin
- silane
- sio
- silicone
- coating
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- 229920002050 silicone resin Polymers 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 24
- 229910052796 boron Inorganic materials 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 31
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 29
- 239000000758 substrate Substances 0.000 claims abstract description 26
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 15
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011248 coating agent Substances 0.000 claims description 47
- 238000000576 coating method Methods 0.000 claims description 47
- 239000003960 organic solvent Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 21
- 239000011347 resin Substances 0.000 claims description 21
- 229920003209 poly(hydridosilsesquioxane) Polymers 0.000 claims description 15
- 238000000197 pyrolysis Methods 0.000 claims description 14
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 9
- 239000012298 atmosphere Substances 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims 1
- 239000010936 titanium Substances 0.000 abstract description 19
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000077 silane Inorganic materials 0.000 description 63
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 28
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 18
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 18
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- 238000004821 distillation Methods 0.000 description 16
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- 239000004215 Carbon black (E152) Substances 0.000 description 4
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229910008051 Si-OH Inorganic materials 0.000 description 4
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- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 239000011521 glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
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- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910018557 Si O Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- LBZRRXXISSKCHV-UHFFFAOYSA-N [B].[O] Chemical compound [B].[O] LBZRRXXISSKCHV-UHFFFAOYSA-N 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- HLQVEUJQDVTTIF-UHFFFAOYSA-N CCO[SiH2]OC(C)CC Chemical class CCO[SiH2]OC(C)CC HLQVEUJQDVTTIF-UHFFFAOYSA-N 0.000 description 1
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- ZCDBRVXGHZHBIX-UHFFFAOYSA-N [acetyloxy-di(propan-2-yloxy)silyl] acetate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)=O)OC(C)=O ZCDBRVXGHZHBIX-UHFFFAOYSA-N 0.000 description 1
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- KHAYZVWNEUMMDR-UHFFFAOYSA-N dimethyl dipropan-2-yl silicate Chemical compound CC(C)O[Si](OC)(OC)OC(C)C KHAYZVWNEUMMDR-UHFFFAOYSA-N 0.000 description 1
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- TZFKGXIWDXYRCE-UHFFFAOYSA-N ethoxy(propan-2-yloxy)silane Chemical class C(C)O[SiH2]OC(C)C TZFKGXIWDXYRCE-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
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- 239000001307 helium Substances 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- HCOKJWUULRTBRS-UHFFFAOYSA-N propan-2-yloxysilane Chemical compound CC(C)O[SiH3] HCOKJWUULRTBRS-UHFFFAOYSA-N 0.000 description 1
- GIOQZJKIWPMFIM-UHFFFAOYSA-N propan-2-yloxysilyl acetate Chemical class C(C)(C)O[SiH2]OC(C)=O GIOQZJKIWPMFIM-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- XNPPQWFAKVLIOW-UHFFFAOYSA-N triethyl propan-2-yl silicate Chemical compound CCO[Si](OCC)(OCC)OC(C)C XNPPQWFAKVLIOW-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- CHUAQURBBLLEGO-UHFFFAOYSA-N trimethyl propan-2-yl silicate Chemical compound CO[Si](OC)(OC)OC(C)C CHUAQURBBLLEGO-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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Abstract
本发明涉及包含硼、铝和/或钛并具有与硅键合的支链烷氧基的硅氧烷树脂;包含硅氧烷树脂的硅氧烷组合物;以及制备涂布的基底的方法,该方法包括将硅氧烷组合物施加到基底上以形成膜并使膜中的硅氧烷树脂热解。
Description
相关申请的交叉引用
根据35 U.S.C.§119(e),本申请要求2006年8月4日提交的美国临时专利申请60/835656的优先权。美国临时专利申请60/835656作为参考并入本文。
技术领域
本发明涉及硅氧烷树脂,更特别涉及包含硼、铝和/或钛并具有与硅键合的支链烷氧基的硅氧烷树脂。本发明还涉及包含硅氧烷树脂的硅氧烷组合物,以及涉及制备涂布的基底的方法,该方法包括将硅氧烷组合物施加到基底上以形成膜并使膜中的硅氧烷树脂热解。
背景技术
本领域已知包含硼的硅氧烷聚合物。例如,Kasgoz等(J.Non-Cryst.Solids 1999,243(2,3),168-174)报道了通过使硅酸与三正丁氧硼反应和然后与1-丁醇进行烷氧基化来合成作为硼硅酸盐凝胶板材和纤维的前体的聚硼硅氧烷。
Kasgoz等(J.Mater.Sci.1999,34(24),6137-6141)描述了通过在四氢呋喃中使四乙酰氧基硅烷与三正丁氧硼反应形成的硼硅氧烷聚合物来制备凝胶和凝胶的性质。
Kasgoz等(J.Polym.Sci.,Part A:Polym.Chem.1994,32(6),1049-1056)报道了通过使用(AcO)4Si和(BuO)3B的溶胶-凝胶法形成SiO2-B2O3凝胶纤维和氧化物。
Kasgoz等(Nippon Seramikkusu Kyokai Gakujutsu Ronbunshi1989,97(11),1432-1434)报道了作为硼硅酸盐纤维的前体的聚硼硅氧烷的制备。
Soraru等(Chem.Mater.1999,11(4),910-919)报道了通过改性硅氧烷烷氧化物[RSi(OEt)3,R=Me、Vi或Et]与B(OEt)3进行共水解合成杂化物SiO2-B2O3凝胶。
Kobayashi等的日本专利公报04-359056公开了通过向式(SiO4)1(PO5/2)m(BO3/2)n所示的有机硅聚合物的树脂溶液中加入硅溶胶获得的树脂组合物,其中l、m和n是(99-40)/(0.5-30)/(0.5-30),并且聚合物的平均分子量是500-30,000。
尽管上述参考文献公开了包含硼的硅氧烷聚合物,但是它们未公开本发明的包含硼、铝和/或钛并且具有与硅键合的支链烷氧基的硅氧烷树脂。
发明概述
本发明涉及下式所示的硅氧烷树脂:
(EOs/2)t(HSiO3/2)v((R1O)3SiO1/2))w((R1O)2SiO2/2))x(R1OSiO3/2)y(SiO4/2)z(I),
其中每个E独立地是选自B、Al和Ti的原子;R1为C1-C10支链烷基;当E为B或Al时s=3或者当E为Ti时s=4;t为0.01到0.8;v为0到0.99;w为0到0.99;x为0到0.99;y为0到0.99;z为0到0.8;w+x+y=0.01到0.99;和t+v+w+x+y+z=1。
本发明还涉及包括上述的硅氧烷树脂和有机溶剂的硅氧烷组合物。
本发明进一步涉及制备涂布的基底的方法,该方法包括:(i)将硅氧烷组合物施加到基底上以形成膜,其中硅氧烷组合物包含式(I)所示的硅氧烷树脂以及有机溶剂;和(ii)使膜中的硅氧烷树脂热解。
本发明的硅氧烷树脂可溶于许多有机溶剂中并且基本上不含凝胶。另外,可热解该硅氧烷树脂得到显示出对许多基底具有良好粘合性的硅酸盐涂层。
本发明的硅氧烷组合物可被方便地配制成具有良好的货架稳定性的单部分组合物。另外,该组合物可通过常规的高速方法如旋涂、浸涂、印刷和喷涂被施加到基底上。
制备涂布的基底的方法可以采用常规的设备和技术进行。另外,该方法还可按比例扩大应用于工业制造工艺中。
本发明的硅氧烷树脂可被用来制备在多种消费器件中有用的保护或介电涂层,所述器件包括半导体器件、液晶、发光二极管、有机发光二极管、光电子器件、光学器件、光伏电池、薄膜电池和太阳能电池。
发明详述
本文使用的术语“支链烷基”是指其中带有游离价的碳原子与两个或三个其它碳原子中的每一个连接的烷基。另外,术语“支链烷氧基”是指其中带有游离价的氧原子与支链烷基连接的烷氧基。另外,符号EOs/2,其中E是B或Al且s=3,表示下式所示的单元:
另外,符号EOs/2,其中E是Ti且s=4,表示下式所示的单元:
本发明的硅氧烷树脂具有下式:
(EOs/2)t(HSiO3/2)v((R1O)3SiO1/2))w((R1O)2SiO2/2))x(R1OSiO3/2)y(SiO4/2)z(I),
其中每个E独立地是选自B、Al和Ti的原子;R1为C1-C10支链烷基;当E为B或Al时s=3或者当E为Ti时s=4;t为0.01到0.8;v为0到0.99;w为0到0.99;x为0到0.99;y为0到0.99;z为0到0.8;w+x+y=0.01到0.99;和t+v+w+x+y+z=1。
由R1表示的支链烷基通常含1-10个碳原子,或者含1-6个碳原子,或者含1-4个碳原子。支链烷基的例子包括但不限于:1-甲基乙基(异丙基),1-甲基丙基(仲丁基),1,1二甲基乙基(叔丁基),1-甲基丁基,1-乙基丙基,1,2-二甲基丙基,1-甲基戊基,1-甲基己基,1-甲基庚基,1-甲基辛基和1-甲基壬基。
在硅氧烷树脂的式(I)中,下标t、v、w、x、y和z是摩尔分数。下标t通常为0.01到0.8,或者为0.02到0.6,或者为0.05到0.4;下标v通常为0到0.99,或者为0.005到0.8,或者为0.01到0.7;下标w通常为0到0.99,或者为0.02到0.5,或者为0.05到0.2;下标x通常为0到0.99,或者为0.005到0.8,或者为0.01到0.7;下标y通常为0到0.99,或者为0.02到0.8,或者为0.05到0.7;下标z通常为0到0.8,或者为0.02到0.7,或者为0.05到0.6;并且总和w+x+y通常为0.01到0.99,或者为0.15到0.90,或者为0.3到0.8。
硅氧烷树脂通常具有的重均分子量为500到150,000,或者为1000到50,000,或者为3000到25,000,其中分子量通过采用折光率检测仪和聚苯乙烯标准样品的凝胶渗透色谱法测定。
硅氧烷树脂通常包含10-110摩尔%或20-105摩尔%或40-100摩尔%的与硅键合的羟基,基于树脂中硅原子的总摩尔数计算,这通过29SiNMR测定。
硅氧烷树脂的例子包括但不限于下式所示的树脂:
(BO3/2)0.3(iso-PrOSiO3/2)0.7,(BO3/2)0.3(sec-BuOSiO3/2)0.7,
(BO3/2)0.3(tert-BuOSiO3/2)0.7,(BO3/2)0.1(HSiO3/2)0.3(iso-PrOSiO3/2)0.6,
(BO3/2)0.1(HSiO3/2)0.3((iso-PrO)2SiO2/2)0.6,(BO3/2)0.1(HSiO3/2)0.3(tert-BuOSiO3/2)0.6,(BO3/2)0.1(HSiO3/2)0.3((sec-BuO)2SiO2/2)0.6,(AlO3/2)0,3(iso-PrOSiO3/2)0.7,(AlO3/2)0.3(sec-BuOSiO3/2)0.7,(AlO3/2)0.3(tert-BuOSiO3/2)0.7,
(AlO3/2)0.1(HSiO3/2)0.3(iso-PrOSiO3/2)0.6,(AlO3/2)0.1(HSiO3/2)0.3((iso-PrO)2SiO2/2)0.6,(AlO3/2)0.1(HSiO3/2)0.3(tert-BuOSiO3/2)0.6,
(AlO3/2)0.1(HSiO3/2)0.3((sec-BuO)2SiO2/2)0.6,(TiO4/2)0.3(iso-PrOSiO3/2)0.7,
(TiO4/2)0.3(sec-BuOSiO3/2)0.7,(TiO4/2)0.3(tert-BuOSiO3/2)0.7,
(TiO4/2)0.1(HSiO3/2)0.3(iso-PrOSiO3/2)0.6,(TiO4/2)0.1(HSiO3/2)0.3((iso-PrO)2SiO2/2)0.6,(TiO4/2)0.1(HSiO3/2)0.3(sec-BuOSiO3/2)0.6,
(TiO4/2)0.1(HSiO3/2)0.3((tert-BuO)2SiO2/2)0.6,(BO3/2)0.15(AlO3/2)0.15(iso-PrOSiO3/2)0.7,(BO3/2)0.15(AlO3/2)0.15(sec-BuOSiO3/2)0.7,
(BO3/2)0.15(AlO3/2)0.15(tert-BuOSiO3/2)0.7,(BO3/2)0.05(AlO3/2)0.05(HSiO3/2)0.3(iso-PrOSiO3/2)0.6,(BO3/2)0.05(AlO3/2)0.05(HSiO3/2)0.3(sec-BuOSiO3/2)0.6,
(BO3/2)0.05(AlO3/2)0.05(HSiO3/2)0.3((tert-BuO)2SiO2/2)0.6,
(BO3/2)0.05((AlO3/2)0.05(HSiO3/2)0.3((iso-PrO)2SiO2/2)0.6,
(BO3/2)0.15(TiO4/2)0.15(iso-PrOSiO3/2)0.7,(BO3/2)0.15(TiO4/2)0.15(sec-BuOSiO3/2)0.7,(BO3/2)0.15(TiO4/2)0.15(tert-BuOSiO3/2)0.7,
(BO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.3(iso-PrOSiO3/2)0.6,
(BO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.3(sec-BuOSiO3/2)0.6,
(BO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.3((tert-BuO)2SiO2/2)0.6,
(BO3/2)0.05((TiO4/2)0.05(HSiO3/2)0.3((iso-PrO)2SiO2/2)0.6,
(AlO3/2)0.15(TiO4/2)0.15(iso-PrOSiO3/2)0.7,(AlO3/2)0.15(TiO4/2)0.15(sec-BuOSiO3/2)0.7,(AlO3/2)0.15(TiO4/2)0.15(tert-BuOSiO3/2)0.7,
(AlO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.3(iso-PrOSiO3/2)0.6,
(AlO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.3(tert-BuOSiO3/2)0.6,
(AlO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.3((sec-BuO)2SiO2/2)0.6,(AlO3/2)0.05
(TiO4/2)0.05(HSiO3/2)0.3((iso-PrO)2SiO2/2)0.6,(BO3/2)0.1(AlO3/2)0.1(TiO4/2)0.1(iso-PrOSiO3/2)0.7,(BO3/2)0.1(AlO3/2)0.1(TiO4/2)0.1(sec-BuOSiO3/2)0.7,
(BO3/2)0.1(AlO3/2)0.1(TiO4/2)0.1(tert-BuOSiO3/2)0.7,
(BO3/2)0.05(AlO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.25(iso-PrOSiO3/2)0.6,
(BO3/2)0.05(AlO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.25(tert-BuOSiO3/2)0.6,
(BO3/2)0.05(AlO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.25((sec-BuO)2SiO2/2)0.6,and
(BO3/2)0.05(AlO3/2)0.05(TiO4/2)0.05(HSiO3/2)0.25((iso-PrO)2SiO2/2)0.6,
其中iso-Pr为异丙基,sec-Bu为仲丁基,tert-Bu为叔丁基,且括号外的数字下标表示摩尔分数。另外,在上述式子中,未指明各单元的顺序。
本发明的硅氧烷树脂可如下制备:(i)使(a)至少一种式E(OR)m所示的烷氧基化合物、(b)至少一种式HSiX3所示的硅烷和(c)至少一种式(R1O)nSiX4-n所示的硅烷与水在有机溶剂存在的条件下反应,形成水解物,其中R为C1-C8烃基,E为选自B、Al和Ti的原子,当E为B或Al时m=3或者当E为Ti时m=4,X为-OH或可水解基团,R1为C1-C10支链烷基,并且n是0、1、2或3,条件是在硅烷(b)和硅烷(c)二者中的-X比在硅烷(c)中的-OR1与水更具反应性;和(ii)将水解物蒸馏以除去水。
在制备硅氧烷树脂的方法的步骤(i)中,(a)至少一种式E(OR)m所示的烷氧基化合物、(b)至少一种式HSiX3所示的硅烷和(c)至少一种式(R1O)nSiX4-n所示的硅烷与水在有机溶剂存在的条件下反应,形成水解物,其中R为C1-C8烃基,E为选自B、Al和Ti的原子,当E为B或Al时m=3或者当E为Ti时m=4,X为-OH或可水解基团,R1为C1-C10支链烷基,并且n是0、1、2或3,条件是在硅烷(b)和硅烷(c)二者中的-X比在硅烷(c)中的-OR1与水更具反应性。
烷氧基化合物(a)为至少一种式E(OR)m所示的烷氧基化合物,其中R为C1-C8烃基,E为选自B、Al和Ti的原子,且当E为B或Al时m=3或者当E为Ti时m=4。
由R表示的烃基通常含1-8个碳原子,或者含3-6个碳原子。包含至少3个碳原子的非环烃基可具有支链或非支链结构。由R表示的烃基的例子包括但不限于:非支链烷基和支链烷基,如甲基,乙基,丙基,1-甲基乙基,丁基,1-甲基丙基,2-甲基丙基,1,1-二甲基乙基,戊基,1-甲基丁基,1-乙基丙基,2-甲基丁基,3-甲基丁基,1,2-二甲基丙基,2,2-二甲基丙基,己基,庚基和辛基;环烷基,如环戊基,环己基和甲基环己基;苯基;烷芳基,如甲苯基和二甲苯基;芳烷基,如苄基和苯乙基;链烯基,如乙烯基,烯丙基和丙烯基;芳基烯基,如苯乙烯基;和炔基,如乙炔基和丙炔基。
适用作烷氧基化合物(a)的烷氧基化合物的例子包括但不限于三甲基硼酸酯,三乙基硼酸酯,三丙基硼酸酯,三异丙基硼酸酯,三叔丁基硼酸酯,三甲氧基铝,三乙氧基铝,三异丙氧基铝,三丁氧基铝,三仲丁氧基铝,三叔丁氧基铝,甲氧基钛(IV),乙氧基钛(IV),丙氧基钛(IV),异丙氧基钛(IV),和叔丁氧基钛(IV)。
烷氧基化合物(a)可以是单-烷氧基化合物或者是包括两种或更多种不同的烷氧基化合物的混合物,每种烷氧基化合物由式E(OR)m表示,其中R、E和m如上所述和例举。
制备烷氧基硼、烷氧基铝和烷氧基钛化合物的方法是本领域公知的;这些化合物中有许多是市售的。
硅烷(b)是至少一种式HSiX3所示的硅烷,其中X为-OH或可水解基团,条件是-X比在硅烷(c)中的-OR1与水更具反应性。本文使用的术语“可水解基团”是指与硅键合的基团在从室温(~23℃±2℃)到100℃的任何温度下在几分钟内例如在三十分钟内在无催化剂的条件下与水反应形成硅烷醇(Si-OH)基团。由X表示的可水解基团的例子包括但不限于-Cl,-Br,-OR,-OCH2CH2OR,CH3C(=O)O-,Et(Me)C=N-O-,CH3C(=O)N(CH3)-和-ONH2,其中R为C1-C8烃基。
适用作硅烷(b)的硅烷的例子包括但不限于三甲氧基硅烷、三乙氧基硅烷、三正丙氧基硅烷和三异丙氧基硅烷。
硅烷(b)可以是单一硅烷或者是包括两种或更多种不同的硅烷的混合物,每种硅烷由式HSiX3所示,其中X如上进行定义和例举。另外,制备包含可水解基团的硅烷的方法是本领域公知的;这些化合物中有许多是市售的。
硅烷(c)是至少一种式(R1O)nSiX4-n所示的硅烷,其中R1为C1-C10支链烷基,X是-OH或可水解基团,且n是0、1、2或3,条件是-X比该硅烷中的-OR1与水更具反应性。
适用作硅烷(c)的硅烷的例子包括但不限于异丙氧基三甲氧基硅烷,异丙氧基三乙氧基硅烷,异丙氧基三乙酰氧基硅烷,仲丁氧基三乙氧基硅烷,仲丁氧基三氨基硅烷,仲丁氧基三乙酰氧基硅烷,叔丁氧基三羟基硅烷,叔丁氧基三甲氧基硅烷,叔丁氧基三乙氧基硅烷,叔丁氧基三乙酰氧基硅烷,二异丙氧基二甲氧基硅烷,二异丙氧基二乙氧基硅烷,二异丙氧基二乙酰氧基硅烷,二仲丁氧基二甲氧基硅烷,二仲丁氧基二乙氧基硅烷,二仲丁氧基二乙酰氧基硅烷,二叔丁氧基二羟基硅烷,二叔丁氧基二甲氧基硅烷,二叔丁氧基二乙氧基硅烷,二叔丁氧基二乙酰氧基硅烷,三异丙氧基甲氧基硅烷,三异丙氧基乙氧基硅烷,三异丙氧基乙酰氧基硅烷,三仲丁氧基甲氧基硅烷,三仲丁氧基乙氧基硅烷,三仲丁氧基乙酰氧基硅烷,三叔丁氧基羟基硅烷,三叔丁氧基甲氧基硅烷,三叔丁氧基乙氧基硅烷和三叔丁氧基乙酰氧基硅烷。
硅烷(c)可以是单一硅烷或者是包括两种或更多种不同的硅烷的混合物,每种硅烷由式(R1O)nSiX4-n所示,其中R1、X和n如上所述和例举。另外,制备包含可水解基团的硅烷的方法是本领域公知的;这些化合物中有许多是市售的。
有机溶剂是至少一种有机溶剂。该有机溶剂可以是任何的非质子或偶极非质子有机溶剂,其与水部分混溶或与水不混溶,与烷氧基化合物(a)、硅烷(b)、硅烷(c)或硅氧烷树脂在本发明的条件下不反应,并且与烷氧基化合物(a)、硅烷(b)、硅烷(c)和硅氧烷树脂可混溶。本文使用的术语“部分混溶”是指水在溶剂中的溶解度在25℃下为低于约0.1克/100克溶剂。优选地,有机溶剂与水形成最小沸腾共沸物。如果有机溶剂不与水形成共沸物,则有机溶剂优选具有的沸点大于水的沸点。否则,在所述方法的蒸馏步骤(ii)期间,有机溶剂可在水之前被完全除去。
有机溶剂的例子包括但不限于饱和脂肪烃,如正戊烷,己烷,正庚烷,异辛烷和十二烷;脂环烃,如环戊烷和环己烷;芳烃,如苯,甲苯,二甲苯和均三甲苯;环醚,如四氢呋喃(THF)和二氧杂环己烷;酮,如甲基异丁基酮(MIBK);卤代烷烃,如三氯乙烷;和卤代芳烃,如溴苯和氯苯。有机溶剂可以是单一有机溶剂,或者是包括两种或更多种不同的有机溶剂的混合物,每种溶剂如上面所定义。
制备硅氧烷树脂的方法可以在用于使有机卤硅烷与水接触的任何标准的反应器中进行。适当的反应器包括玻璃反应器和聚四氟乙烯内衬的玻璃反应器。优选地,反应器装备有搅动如搅拌装置。
烷氧基化合物(a)、硅烷(b)、硅烷(c)、有机溶剂和水通常如下结合:将水加入到组分(a)、(b)、(c)和有机溶剂的混合物中。反向加入,即,将烷氧基化合物(a)、硅烷(b)和硅烷(c)加入到水中也是可以的。然而,反向加入可能导致形成凝胶。
对于装备有有效的搅拌装置的1000毫升的反应容器而言,将水加入到烷氧基化合物(a)、硅烷(b)和硅烷(c)中的添加速度通常为1-100毫升/分钟。当添加速度太慢时,反应时间不必要地被延长。当添加速度太快时,反应混合物可能形成凝胶。
烷氧基化合物(a)、硅烷(b)和硅烷(c)与水的反应通常在20℃-150℃或20℃-100℃的温度下进行。在硅烷(b)和/或硅烷(c)中的与硅键合的可水解基团-X是酰氧基如乙酰氧基时,反应通常在低于50℃的温度下进行。
反应时间取决于以下的几个因素:烷氧基化合物(a)、硅烷(b)和硅烷(c)的结构以及温度。反应通常进行足够使烷氧基化合物(a)、硅烷(b)和硅烷(c)完全水解的时间段。本文使用的术语“完全水解”是指在烷氧基化合物(a)、硅烷(b)和硅烷(c)中原来存在的至少85摩尔%的与硅键合的基团-OR和-X被转化成与硅键合的羟基。例如,在20-60℃下,反应时间通常为5-180分钟,或者为10-60分钟,或者为15-25分钟。最佳的反应时间可采用下文实施例中所述方法通过常规试验确定。
基于组分(a)、(b)和(c)的摩尔数的总和,烷氧基化合物(a)的浓度通常为1到80摩尔%,或者为10到40摩尔%,或者为5到15摩尔%。
基于反应混合物的总重量,有机溶剂的浓度通常为30到99%(w/w),或者为45到90%(w/w),或者为40到80%(w/w)。
反应混合物中水的浓度通常足以实现烷氧基化合物(a)、硅烷(b)和硅烷(c)的水解。例如,水的浓度通常为使得水的摩尔数与在烷氧基化合物(a)、硅烷(b)和硅烷(c)中的与硅键合的基团-OR和-X的摩尔数总和的比为0.5到2,或者为0.8到1.2。
在制备硅氧烷树脂的方法的步骤(ii)中,将水解物蒸馏以除去水。该蒸馏可以在大气压或低于大气压的压力下进行。当溶剂与水形成最小沸腾共沸物时,蒸馏可以方便地使用迪安-斯达克分水器进行,该分水器收集水并使溶剂返回到蒸馏器中。蒸馏通常在80-110℃或90-110℃的温度下在100kPa下进行。蒸馏通常持续进行足够产生具有500到150,000重均分子量的硅氧烷树脂的时间段。
当在硅烷(b)和/或硅烷(c)中的与硅结合的可水解基团-X是酰氧基如乙酰氧基时,酸(如乙酸)在步骤(i)的水解反应中作为副产物产生,该酸可不利地影响硅氧烷树脂产品的稳定性。在这种情况下,水解物中的酸通常在步骤(ii)中将水解物蒸馏以除去水之前被中和或被除去。酸可以通过用中和剂处理水解物而被中和。适当的中和剂的例子包括但不限于无机碱如碳酸钙、碳酸钠、碳酸氢钠、碳酸铵,氨水,氧化钙和氢氧化钙。或者,酸可以通过蒸馏水解物以与溶剂的共沸物形式被除去。
硅氧烷树脂可无需进一步分离或纯化即可使用,或者,该树脂可以通过常规的蒸发方法与大部分溶剂分离。例如,经蒸馏的水解物可以在减压下被加热。
本发明的硅氧烷组合物包含:
(A)下式所示的硅氧烷树脂:
(EOs/2)t(HSiO3/2)v((R1O)3SiO1/2))w((R1O)2SiO2/2))x(R1OSiO3/2)y(SiO4/2)z(I),
其中每个E独立地是选自B、Al和Ti的原子;R1为C1-C10支链烷基;当E为B或Al时s=3或者当E为Ti时s=4;t为0.01到0.8;v为0到0.99;w为0到0.99;x为0到0.99;y为0到0.99;z为0到0.8;w+x+y=0.01到0.99;和t+v+w+x+y+z=1;和
(B)有机溶剂。
组分(A)是如上描述和例举的式(I)的硅氧烷树脂。组分(A)可以是单一的硅氧烷树脂或者是包括两种或更多种不同的硅氧烷树脂的混合物,其中每种硅氧烷树脂如式(I)所示。
组分(B)是至少一种有机溶剂。该有机溶剂可以是任何的质子、非质子或偶极非质子有机溶剂,其不与硅氧烷树脂反应并且可与硅氧烷树脂混溶。
有机溶剂的例子包括但不限于:醇,如甲醇,乙醇,1-丙醇,2-丙醇,1-丁醇,2-丁醇,2-甲基基-1-丁醇,1-戊醇和环己醇;饱和脂肪烃,如正戊烷,己烷,正庚烷,异辛烷和十二烷;脂环烃,如环戊烷和环己烷;芳烃,如苯,甲苯,二甲苯和均三甲苯;环醚,如四氢呋喃(THF)和二氧杂环己烷;酮,如甲基异丁基酮(MIBK);卤代烷烃,如三氯乙烷;和卤代芳烃,如溴苯和氯苯。有机溶剂可以是单一有机溶剂,或者是包括两种或更多种不同的有机溶剂的混合物,其中每种溶剂如上面定义。
基于硅氧烷组合物的总重量,有机溶剂的浓度通常为20-95%(w/w),或者为50-90%(w/w),或者为70-80%(w/w)。
硅氧烷组合物可以进一步包含氢倍半硅氧烷树脂。氢倍半硅氧烷树脂(H-树脂)可由通式HSi(OH)a(OR′)bOc/2表示,其中每个R′独立地为烃基,其当通过氧原子与硅结合时形成可水解的取代基,a=0-2,b=0-2,c=1-3,且a+b+c=3。烃基的例子包括:烷基,例如甲基,乙基,丙基和丁基;芳基,例如苯基;和链烯基,如烯丙基和乙烯基。这些树脂可完全缩合(HSiO3/2)n或部分水解(即,包含一些Si-OR′基团)和/或部分缩合(即,包含一些Si-OH基团)。尽管不由上式表示,但是树脂还可包含少量(例如低于约10%)的结合有0或2个氢原子的硅原子。
氢倍半硅氧烷树脂可以是单一的氢倍半硅氧烷树脂,或者是包括两种或更多种不同的氢倍半硅氧烷树脂的混合物,每种氢倍半硅氧烷树脂如上所述。
当在硅氧烷组合物中存在氢倍半硅氧烷树脂时,基于硅氧烷组合物的总重量,氢倍半硅氧烷树脂的浓度通常为1-99%(w/w),或者为2-60%(w/w),或者为5-40%(w/w)。
制备H-树脂的方法是本领域公知的,并且例举在Collins等的美国专利3,615,272;Bank等的美国专利5,010,159;Frye等的美国专利4,999,397;Hanneman等的美国专利5,063,267;Frye等的美国专利4,999,397;日本公开特许公报59-178749;日本公开特许公报60-86017;和日本公开特许公报63-107122中。
本发明的涂布的基底包括:
基底;和
基底上的涂层,其中涂层是下式所示的硅氧烷树脂的热解产物:
(EOs/2)t(HSiO3/2)v((R1O)3SiO1/2))w((R1O)2SiO2/2))x(R1OSiO3/2)y(SiO4/2)z(I),
其中每个E独立地是选自B、Al和Ti的原子;R1为C1-C10支链烷基;当E为B或Al时s=3或者当E为Ti时s=4;t为0.01到0.8;v为0到0.99;w为0到0.99;x为0到0.99;y为0到0.99;z为0到0.8;w+x+y=0.01到0.99;和t+v+w+x+y+z=1。
基底可以是任何的硬质或挠性的具有平坦、复杂或不规则轮廓的材料。基底可透过或不透过电磁谱可见光谱区(~400到~700nm)内的光。另外,基底可以是电的导体、半导体或绝缘体。另外,基底可以是电子器件,如分立器件和集成电路。
基底的例子包括但不限于半导体,例如硅,具有二氧化硅表层的硅,碳化硅,磷化铟和砷化镓;石英;熔融石英;氧化铝;陶瓷;玻璃;金属箔;聚烯烃,例如聚乙烯,聚丙烯,聚苯乙烯,聚对苯二甲酸乙二酯(PET)和聚萘二甲酸乙二酯;碳氟聚合物,例如聚四氟乙烯和聚氟乙烯;聚酰胺,例如尼龙;聚酰亚胺;聚酯,例如聚(甲基丙烯酸甲酯);环氧树脂;聚醚;聚碳酸酯;聚砜;和聚醚砜。
分立器件的例子包括但不限于:二极管,如PIN二极管,参考电压二极管,变容二极管,雪崩二极管,DIAC,耿氏二极管,急变二极管,IMPATT二极管,隧道二极管,齐纳二极管,标准(p-n)二极管,和Shottky二极管;晶体管,如双极晶体管,包括绝缘栅双极晶体管(IGBT)和达林顿晶体管,以及场效应晶体管(FET),包括金属氧化物半导体FET(MOSFET),结型场效应晶体管(JFET),金属-半导体场效应晶体管(MESFET),有机FET,高电子迁移率晶体管(HEMT),和薄膜晶体管(TFT),包括有机场效应晶体管;晶闸管,例如DIAC,TRIAC,硅控整流器(SCR),分布缓冲-闸门关断(DB-GTO)晶闸管,闸门关断(GTO)晶闸管,MOFSET控晶闸管(MCT),改性阳极-闸门关断(MA-GTO)晶闸管,静电感应晶闸管(SITh)和场控制晶闸管(FCTh);调节电阻器;电阻器;容电器;电容器;热敏电阻器;和光电子器件,例如光二极管,太阳能电池(例如CIGS太阳能电池和有机光伏电池),光敏晶体管,光电倍增器,集成光学电路(IOC)元件,光敏电阻,激光二极管,发光二极管(LED),和有机发光二极管(OLED),包括小分子OLED(SM-OLED)和聚合物发光二极管(PLED)。
集成电路的例子包括但不限于:单片式集成电路,例如存储器IC,包括RAM(随机存取存储器),包括DRAM和SRAM,以及ROM(只读存储器);逻辑电路;模拟集成电路;混合式集成电路,包括薄膜混合式集成电路和厚膜混合式集成电路;薄膜电池;和燃料电池。
基底上的涂层是下式所示的硅氧烷树脂的热解产物:
(EOs/2)t(HSiO3/2)v((R1O)3SiO1/2))w((R1O)2SiO2/2))x(R1OSiO3/2)y(SiO4/2)z(I),
其中E,R1,s,t,v,w,x,y,z,w+x+y和t+v+w+x+y+z如上面定义和例举。本文使用的术语“硅氧烷树脂的热解产物”是指包含硼、铝和钛中至少之一的硅酸盐玻璃。
涂布的基底的涂层通常具有的厚度为0.1到5微米,或者为0.2到3微米,或者为0.25到2微米。
涂层通常具有的介电常数为2.5到3.4,或者为2.6到3。另外,涂层通常具有的杨氏模量为7到20GPa,或者为7到15GPa。另外,对于具有632.8纳米波长的光而言,涂层通常具有的折射率为1.30到1.50,或者为1.35到1.47。
涂布的基底可以如下制备:将上述包括本发明的硅氧烷树脂和有机溶剂的硅氧烷组合物施加到基底上,以形成膜,并使膜中的硅氧烷树脂热解。
可以采用常规方法如旋涂、浸涂、喷涂、流涂、丝网印刷和辊涂将上述的硅氧烷组合物施加到基底上。当存在溶剂时,溶剂通常在膜被加热之前从涂布的基底中被蒸发。可采用任何适当的蒸发方法,例如简单的空气干燥,施加真空,或加热(最高约50℃)。
可以如下热解硅氧烷树脂:将膜在空气或惰性气体如氮气、氦气或氩气的气氛中在350-1000℃或350-800℃或400-700℃的温度下加热。可以在大气压、低于大气压或超过大气压的压力下加热膜。可以采用常规设备如石英管熔炉、对流加热炉和辐射能体系(例如微波炉)加热膜。通常加热膜持续一定的时间段,使得热解的产物在25℃下的杨氏模量为至少5GPa。例如,通常加热膜持续0.1-3小时或0.5-1.5小时的时间段。
或者,可以如下热解膜中的硅氧烷树脂:首先固化膜中的硅氧烷树脂(即,交联),然后在350-800℃的温度下加热该固化的硅氧烷树脂。可以通过在50-260℃或50-250或100-200℃的温度下加热膜而固化硅氧烷树脂。
本发明的方法可以进一步包括在包括硅氧烷树脂的热解产物的涂层的至少一部分上形成涂层。涂层的例子包括但不限于:无机氧化物,例如铟锡氧化物,二氧化硅和二氧化钛;无机氮化物,如氮化硅和氮化镓;无机碳化物,如碳化硅和氢化碳氧化硅;金属,例如铜,银,金,镍和铬;和硅,例如非晶硅,微晶硅和多晶硅。形成无机涂层的方法,例如物理气相沉积和化学蒸气沉积,是本领域公知的。
本发明的硅氧烷树脂可溶于许多有机溶剂中并且基本上不含凝胶。另外,可热解该硅氧烷树脂得到显示出对许多基底具有良好粘合性的硅酸盐涂层。
本发明的硅氧烷组合物可被方便地配制成具有良好的货架稳定性的单部分组合物。另外,该组合物可通过常规的高速方法如旋涂、浸涂、印刷和喷涂被施加到基底上。
制备涂布的基底的方法可以采用常规的设备和技术进行。另外,该方法还可按比例扩大应用于工业制造工艺中。
本发明的硅氧烷树脂可被用来制备在多种消费器件中有用的保护或介电涂层,所述器件包括半导体器件、液晶、发光二极管、有机发光二极管、光电子器件、光学器件、光伏电池、薄膜电池和太阳能电池。
实施例
提供以下的实施例以更好地说明本发明的硅氧烷树脂、硅氧烷组合物和方法,但是这些实施例不被认为对本发明构成限制,本发明的范围由权利要求书限定。除非另作说明,实施例中报道的所有的份数和百分数用重量表示。在实施例中使用了以下的方法和材料。
分子量
硅氧烷树脂的数均分子量和重均分子量(Mn和Mw)采用PLgel(Polymer Laboratories,Inc.)5微米柱在室温(~23℃)下以1毫升/分钟的THF流动相和折光率检测器通过凝胶渗透色谱法(GPC)进行测定。聚苯乙烯标准样品用于线性回归校准。
红外光谱
将涂布的硅片的红外光谱记录在Perkin Elmer Instruments 1600FT-IR分光计上。
折射率和厚度
硅片上涂层的折射率(RI)和厚度采用装备有用于数据分析的WVASE32软件的Woollam M-88光谱椭圆偏振光计进行测量。测量在20℃下对于具有632.8纳米波长的光的折射率。关于折射率和厚度的报道值各自表示在相同涂布的硅片的不同区域上进行三次测量的平均值。
介电常数
涂层的介电常数由采用HP4194A Impedance/Gain-Phase分析仪在金属-绝缘体-半导体(MIS)电容器上进行的电容测量来测定。通过蒸发将环形的铝电极沉积到涂层上。采用具有相同直径的电极对测量通过硅片的串联电容。使用三对具有不同直径(0.12英寸、0.191英寸和0.252英寸)的电极在102-107赫兹的频率范围内获得电容测量值。报道的介电常数来自在106赫兹下进行的测量值。介电常数Dk的报告值表示采用具有不同直径的电极进行三次测量的平均值。
对比模量和硬度
硅片上涂层的对比模量和硬度在室温(~23℃±2℃)下,采用装备有Berkovich金刚石压痕计的Hysitron纳米机械测试仪进行测量。硬度和对比模量值在约15%的透入深度下进行测定。对比模量可采用以下公式计算:
ER=E/(1-v2),
其中:
ER是对比模量,GPa,
E是杨氏模量,GPa,和
v是泊松比。
杨氏模量由载荷位移曲线的斜率确定。对比模量和硬度的报道值各自表示对相同涂布的硅片的不同区域上进行三次测量的平均值。
三乙氧基硅烷得自Gelest(Morrisville,Pennsylvania)。
三甲基硼酸酯(≥90%)得自Aldrich(St.Louis,Missouri)。
四叔丁氧基钛得自Dow Corning Corporation(Midland,Michigan)。
二叔丁氧基二乙酰氧基硅烷得自Gelest(Morrisville,Pennsylvania)。
实施例1
在氩气下,在2升烧瓶中,将三乙氧基硅烷(45.0克)、14.2克的三甲基硼酸酯、280.0克的二叔丁氧基二乙酰氧基硅烷和440.6克的四氢呋喃混合。在14分钟内,将水(53.4克)加入到混合物中。在室温下搅拌混合物1小时,然后用400.3克的甲苯稀释。使用旋转蒸发器将混合物在33℃下减压浓缩。将残余物用500.6克的甲苯处理,并使用旋转蒸发器将混合物再次在33℃下减压浓缩。最后,将残余物用720.7克的甲苯处理,并将混合物转移到装备有迪安-斯达克分水器和温度计的烧瓶中。将混合物蒸馏以除去与甲苯的共沸物形式的任何残留的乙酸。在除去214克的挥发性物质后,将水解物蒸馏1小时以除去水。在此期间,允许溶剂返回到蒸馏烧瓶中。将冷却的溶液过滤并使用旋转蒸发器在33℃下减压浓缩。将残余物进一步在25℃下在高真空(1毫米汞柱)下浓缩,得到148克的硅氧烷树脂。
实施例2
在氩气下,在2升烧瓶中,将三乙氧基硅烷(33.7克)、7.3克的三甲基硼酸酯、120.6克的二叔丁氧基二乙酰氧基硅烷和220.6克的四氢呋喃混合。在14分钟内,将水(26.6克)加入到混合物中。在室温下搅拌混合物1小时,然后用200.5克的甲苯稀释。使用旋转蒸发器将混合物在33℃下减压浓缩。将残余物用250.4克的甲苯处理,并使用旋转蒸发器将混合物再次在33℃下减压浓缩。最后,将残余物用360克的甲苯处理,并将混合物转移到装备有迪安-斯达克分水器和温度计的烧瓶中。将混合物蒸馏以除去与甲苯的共沸物形式的任何残留的乙酸。在除去214克的挥发性物质后,将水解物蒸馏1小时以除去水。在此期间,允许溶剂返回到蒸馏烧瓶中。将冷却的溶液过滤并使用旋转蒸发器在33℃下减压浓缩。将残余物进一步在25℃下在高真空(1毫米汞柱)下浓缩,得到72.3克的硅氧烷树脂。
实施例3
在1升烧瓶中,将二叔丁氧基二乙酰氧基硅烷(40.0克)与120.0克的四氢呋喃混合。向溶液中慢慢地滴加水(4.9克)。在室温下搅拌混合物30分钟。向混合物中慢慢地加入四叔丁氧基钛(20.0克)。将反应混合物在室温下搅拌1小时,然后用100克的甲苯稀释。采用旋转蒸发器将混合物在25-35℃下减压浓缩。将残余物用200.6克的甲苯处理,并使用旋转蒸发器将混合物再次在33℃下减压浓缩。最后,将残余物用140克的甲苯处理,并将混合物转移到装备有迪安-斯达克分水器和温度计的烧瓶中。将混合物蒸馏以除去与甲苯的共沸物形式的任何残留的乙酸。在除去22克的挥发性物质后,将水解物蒸馏1小时以除去水。在此期间,允许溶剂返回到蒸馏烧瓶中。将经冷却的溶液过滤并使用旋转蒸发器在33℃下进行减压浓缩。将残余物进一步在25℃下在高真空(1毫米汞柱)下浓缩,得到30克的具有1550的重均分子量和979的数均分子量的硅氧烷树脂。
实施例4
在1升烧瓶中,将二叔丁氧基二乙酰氧基硅烷(40.0克)与120.0克的四氢呋喃混合。向溶液中慢慢地滴加水(7.7克)。在室温下搅拌混合物20分钟。在10分钟内向混合物中加入四叔丁氧基钛(46.7克)。将反应混合物在室温下搅拌1小时,然后用100克的甲苯稀释。采用旋转蒸发器将混合物在25-35℃下减压浓缩。将残余物用200克的甲苯处理,并使用旋转蒸发器将混合物再次在33℃下减压浓缩。最后,将残余物用140克的甲苯处理,并将混合物转移到装备有迪安-斯达克分水器和温度计的烧瓶中。在除去22克的挥发性物质后,将水解物蒸馏1小时以除去水。在此期间,允许溶剂返回到蒸馏烧瓶中。将经冷却的溶液过滤并使用旋转蒸发器在33℃下减压浓缩。将残余物进一步在25℃下在高真空(1毫米汞柱)下浓缩,得到51克的具有1500的重均分子量和1120的数均分子量的硅氧烷树脂。
实施例5
在氩气下,在2升烧瓶中,将三甲基硼酸酯(6.0克)和150.2克的二叔丁氧基二乙酰氧基硅烷和260.4克的四氢呋喃混合。将水(20.2克)滴加到混合物中。在室温下搅拌混合物1小时,然后用200.3克的甲苯稀释。使用旋转蒸发器将混合物在33℃下减压浓缩。将残余物用250.1克的甲苯处理,并使用旋转蒸发器将混合物再次在33℃下减压浓缩。最后,将残余物用209.9克的甲苯处理,并将混合物转移到装备有迪安-斯达克分水器和温度计的烧瓶中。将水解物蒸馏1小时以除去水。在此期间,允许溶剂返回到蒸馏烧瓶中。将经冷却的溶液过滤并使用旋转蒸发器在33℃下减压浓缩。将残余物进一步在25℃下在高真空(1毫米汞柱)下浓缩,得到67.7克的具有12100的重均分子量和5140的数均分子量的硅氧烷树脂。
实施例6
将包含25%(w/w)在甲基异丁基酮中的实施例2的硅氧烷树脂的溶液过滤通过1.0微米和0.2微米的注射器膜滤器组合。将溶液旋涂在150毫米单晶硅片上(2000rpm,20秒),将涂布的硅片置于处在氮气氛下(流速=20升/分钟)的石英管熔炉中。将熔炉以25℃/分钟的速度加热到700℃,在700℃保持30分钟,然后将其冷却到室温并同时保持氮气流。涂层厚度为3982,折射率为1.3788,模量为12.9GPa,且在1MHz下的介电常数(Dk)为4.46。涂层的FT-IR光谱显示,基于涂层中Si-O键的总摩尔数SiO2包含痕量的Si-H和4.43摩尔%的Si-OH。
实施例7
将包含25%(w/w)在甲基异丁基酮中的实施例2的硅氧烷树脂的溶液过滤通过1.0微米和0.2微米的注射器膜滤器组合。将溶液旋涂在150毫米单晶硅片上(1000rpm,20秒)。将涂布的硅片置于石英管熔炉中并将熔炉用氮气吹扫(流速=20升/分钟)。将氮气替换为流速为10升/分钟的氧气。将熔炉以25℃/分钟的速度加热到680℃。当温度达到680℃时,将加热速度降低到4℃/分钟。将蒸汽以24克/分钟的速度引入到熔炉中。将熔炉在700℃保持30分钟,同时保持氧气和蒸汽流。然后中止氧气和蒸汽并将氮气以20升/分钟的流速引入到熔炉中。以25℃/分钟的速度将熔炉冷却到室温。涂层厚度为3180,折射率为1.390,模量为36.6GPa,且硬度为2.67GPa。涂层的FT-IR光谱显示,基于涂层中Si-O键的总摩尔数不含残余的Si-H且包含1.6摩尔%的Si-OH。
实施例8
将包含25%(w/w)在甲基异丁基酮中的实施例2的硅氧烷树脂的溶液(15.5克)与84.5克的-17 Flowable Oxide混合。将得到的溶液旋涂在150mm单晶硅片上以实现加热后的膜厚度为1微米。将涂布的硅片在150℃、200℃和350℃下的三个加热板的每个加热板上加热1分钟。然后将涂布的硅片置于处在氮气氛(流速=20升/分钟)的石英管熔炉中。将熔炉在400℃加热60分钟,然后将其冷却到室温并同时保持氮气流。涂布的硅片的机械性能如表1所示。
实施例9
如实施例8所述制备涂布的硅片,不同之处在于最终的加热步骤在425℃而非400℃下进行。涂布的硅片的机械性能如表1所示。
实施例10
实施例11
如实施例10所述制备涂布的硅片,不同之处在于最终的加热步骤在425℃而非400℃下进行。涂布的硅片的机械性能如表1所示。
实施例12
将包含25%(w/w)在甲基异丁基酮中的实施例1的硅氧烷树脂的溶液(5克)与95克的-17 Flowable Oxide混合。如实施例8所述制备涂布的硅片。涂布的硅片的机械性能如表1所示。
比较例1
比较例2
如比较例1所述制备涂布的硅片,不同之处在于最终的加热步骤在425℃而非400℃下进行。涂布的硅片的机械性能如表1所示。
表1
RI是指折射率,Dk是指介电常数,和模量是指对比模量。
Claims (10)
1.一种硅氧烷树脂,其具有下式:
(EOs/2)t(HSiO3/2)v((R1O)3SiO1/2)w((R1O)2SiO2/2)x(R1OSiO3/2)y(SiO4/2)z(I),
其中每个E独立地是选自B、Al和Ti的原子;R1为C1-C10支链烷基;当E为B或Al时s=3或者当E为Ti时s=4;t为0.01到0.8;v为0到0.99;w为0到0.99;x为0到0.99;y为0到0.99;z为0到0.8;w+x+y=0.01到0.99;和t+v+w+x+y+z=1。
2.权利要求1的硅氧烷树脂,其中E是硼。
3.权利要求1的硅氧烷树脂,其中硅氧烷树脂包含20-105摩尔%的与硅键合的羟基,基于树脂中硅原子的总摩尔数计算。
4.一种硅氧烷组合物,其包含:
(A)下式所示的硅氧烷树脂:
(EOs/2)t(HSiO3/2)v((R1O)3SiO1/2)w((R1O)2SiO2/2)x(R1OSiO3/2)y(SiO4/2)z(I),
其中每个E独立地是选自B、Al和Ti的原子;R1为C1-C10支链烷基;当E为B或Al时s=3或者当E为Ti时s=4;t为0.01到0.8;v为0到0.99;w为0到0.99;x为0到0.99;y为0到0.99;z为0到0.8;w+x+y=0.01到0.99;和t+v+w+x+y+z=1;和
(B)有机溶剂。
5.权利要求4的硅氧烷组合物,其中E是硼。
6.权利要求4的硅氧烷组合物,进一步包含氢倍半硅氧烷树脂。
7.一种制备涂布的基底的方法,该方法包括:
将硅氧烷组合物施加到基底上以形成膜,其中硅氧烷组合物包含:
(A)下式所示的硅氧烷树脂:
(EOs/2)t(HSiO3/2)v((R1O)3SiO1/2)w((R1O)2SiO2/2)x(R1OSiO3/2)y(SiO4/2)z(I),
其中每个E独立地是选自B、Al和Ti的原子;R1为C1-C10支链烷基;当E为B或Al时s=3或者当E为Ti时s=4;t为0.01到0.8;v为0到0.99;w为0到0.99;x为0到0.99;y为0到0.99;z为0到0.8;w+x+y=0.01到0.99;和t+v+w+x+y+z=1;和
(B)有机溶剂;和
使膜中的硅氧烷树脂热解。
8.权利要求7的方法,其中E是硼。
9.权利要求7的方法,其中热解步骤在惰性气体的气氛中进行。
10.权利要求7的方法,其中热解步骤在350-800℃的温度下进行。
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2007
- 2007-07-23 JP JP2009522781A patent/JP5107354B2/ja not_active Expired - Fee Related
- 2007-07-23 WO PCT/US2007/016522 patent/WO2008018981A2/en active Application Filing
- 2007-07-23 US US12/375,436 patent/US7989030B2/en not_active Expired - Fee Related
- 2007-07-23 CN CN2007800291096A patent/CN101501139B/zh not_active Expired - Fee Related
- 2007-07-23 EP EP07836185A patent/EP2046893A2/en not_active Withdrawn
- 2007-07-23 KR KR1020097002180A patent/KR20090034953A/ko active IP Right Grant
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EP0625532A1 (en) * | 1993-05-17 | 1994-11-23 | Dow Corning Corporation | Precursor for ceramic coatings |
CN1367205A (zh) * | 2001-01-17 | 2002-09-04 | 气体产品与化学公司 | 用于低介电常数层间介质薄膜的有机硅前体 |
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Also Published As
Publication number | Publication date |
---|---|
CN101501139A (zh) | 2009-08-05 |
WO2008018981A2 (en) | 2008-02-14 |
WO2008018981A3 (en) | 2008-03-20 |
EP2046893A2 (en) | 2009-04-15 |
US20090226609A1 (en) | 2009-09-10 |
KR20090034953A (ko) | 2009-04-08 |
JP2009545649A (ja) | 2009-12-24 |
JP5107354B2 (ja) | 2012-12-26 |
US7989030B2 (en) | 2011-08-02 |
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