CN103415576B - 氧化锌系膜形成用组合物、氧化锌系膜的制造方法及锌化合物 - Google Patents
氧化锌系膜形成用组合物、氧化锌系膜的制造方法及锌化合物 Download PDFInfo
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- CN103415576B CN103415576B CN201280012284.5A CN201280012284A CN103415576B CN 103415576 B CN103415576 B CN 103415576B CN 201280012284 A CN201280012284 A CN 201280012284A CN 103415576 B CN103415576 B CN 103415576B
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- Prior art keywords
- zinc oxide
- mesentery
- oxide mesentery
- cpds
- composition
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 title claims abstract description 210
- 239000011787 zinc oxide Substances 0.000 title claims abstract description 105
- 210000000713 mesentery Anatomy 0.000 title claims abstract description 88
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 43
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 54
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 34
- 239000011159 matrix material Substances 0.000 claims description 15
- -1 acyl acetic acid ester Chemical class 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000011247 coating layer Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 229960001296 zinc oxide Drugs 0.000 description 92
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 239000011701 zinc Chemical class 0.000 description 15
- 229910052725 zinc Inorganic materials 0.000 description 15
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 14
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000007591 painting process Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003595 mist Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CBQQDXWCFAEIDL-UHFFFAOYSA-N CC(O)=O.CCC(C)OC(C)CC Chemical compound CC(O)=O.CCC(C)OC(C)CC CBQQDXWCFAEIDL-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- PKZCRWFNSBIBEW-UHFFFAOYSA-N 2-n,2-n,2-trimethylpropane-1,2-diamine Chemical compound CN(C)C(C)(C)CN PKZCRWFNSBIBEW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/09—Diamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/65—Metal complexes of amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C07C69/72—Acetoacetic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D1/00—Coating compositions, e.g. paints, varnishes or lacquers, based on inorganic substances
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/06—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the coating material
- C23C14/08—Oxides
- C23C14/086—Oxides of zinc, germanium, cadmium, indium, tin, thallium or bismuth
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
- C23C18/12—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material
- C23C18/1204—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition characterised by the deposition of inorganic material other than metallic material inorganic material, e.g. non-oxide and non-metallic such as sulfides, nitrides based compounds
- C23C18/1208—Oxides, e.g. ceramics
- C23C18/1216—Metal oxides
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/16—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by reduction or substitution, e.g. electroless plating
- C23C18/31—Coating with metals
- C23C18/42—Coating with noble metals
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- H—ELECTRICITY
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Abstract
本发明提供一种含有下述通式(1)(在通式(1)中,R1及R2彼此独立地表示碳原子数1~4的烷基)所示的锌化合物作为必需成分的氧化锌系膜形成用组合物、氧化锌系膜的制造方法及锌化合物。根据上述本发明,可提供一种氧化锌系膜形成用组合物,其可在300℃以下的低温下形成具有透明性、均质性及导电性的高品质的氧化锌系膜。
Description
技术领域
本发明涉及一种用于在各种基体上形成氧化锌系膜的氧化锌系膜形成用组合物、使用其的氧化锌系膜的制造方法、及适用于氧化锌膜形成用组合物的锌化合物。
背景技术
研究了氧化锌系膜作为透明导电膜、电极材料、半导体的各种应用。作为使用氧化锌的前体化合物形成氧化锌系膜的方法,报道了CVD法、ALD法等使前体化合物气化而成的气体与基体(基体材料)接触的气相工艺;MOD法、溶胶-凝胶法等使前体化合物的溶液或分散液与基体接触的液相工艺。
作为这些工艺中所使用的氧化锌的前体化合物即锌化合物,有醇盐、β-二酮络合物、有机酸金属盐、烷基锌、无机盐等。这些前体化合物通过利用加热和/或氧化剂的反应转化为氧化锌。
例如,在专利文献1中公开了下述氧化锌薄膜的制造方法:使分散有锌化合物的粉末或微粒的悬浮液与基体表面接触后,使锌化合物热分解而转化为氧化锌。需要说明的是,作为锌化合物,公开了醋酸锌、锌的乙酰丙酮盐、草酸锌、乳酸锌。
另外,在专利文献2中公开下述方法:使在大气压或大气压附近的压力下为等离子体状态的有机金属化合物气体与基体接触来形成透明导电膜。在专利文献2中,例示了氧化锌作为透明导电膜,例示了乙酰乙酸乙酯作为用于形成有机金属的配合基。另外,例示了乙酰丙酮锌作为锌化合物。
一般认为在使用前体化合物形成氧化锌系膜的情况下,为了表现出所期待的功能,转化为品质优异的氧化锌膜所需的温度为350℃以上。然而,由于对树脂基体的适应性及减少相对于基体的损伤等原因,优选可在更低温下转化为氧化锌系膜。因此,期望开发一种与以往相比以低温的成膜温度制造氧化锌系膜的方法。
现有技术文献
专利文献
专利文献1:日本特开平7-180060号公报
专利文献2:日本特开2004-22268号公报
发明内容
发明所要解决的课题
本发明是鉴于这样的现有技术所具有的课题而完成的,研究该课题时,可提供一种氧化锌系膜形成用组合物及其所使用的锌化合物,所述氧化锌系膜形成用组合物可在300℃以下的低温下形成具有透明性、均质性及导电性的高品质的氧化锌系膜。另外,研究本发明的课题时,可提供一种氧化锌系膜的制造方法,该方法可在300℃以下的低温下形成具有透明性、均质性及导电性的高品质的氧化锌系膜。
用于解决课题的方法
本发明人等进行了潜心研究,结果发现,通过使用具有特定结构的锌化合物,可解决上述课题,以至完成了本发明。即,根据本发明,可提供一种含有下述通式(1)所示的锌化合物作为必需成分的氧化锌系膜形成用组合物。
(在所述通式(1)中,R1及R2彼此独立地表示碳原子数1~4的烷基)
在本发明中,优选所述通式(1)中的R1及R2为甲基。
另外,根据本发明,可提供一种氧化锌系膜的制造方法,其包括:将上述的氧化锌系膜形成用组合物涂布在基体上形成涂布层的工序;和在150~300℃下对所述涂布层进行处理来转化为膜的工序。
另外,根据本发明,可提供下述式(2)所示的锌化合物。
发明的效果
使用本发明的氧化锌系膜形成用组合物及锌化合物,可以在300℃以下的低温下形成具有透明性、均质性及导电性的高品质的氧化锌系膜。另外,根据本发明的氧化锌系膜的制造方法,可以在300℃以下的低温下形成具有透明性、均质性及导电性的高品质氧化锌系膜。
附图说明
图1为式(2)所示的锌化合物的IR图表。
图2为式(2)所示的锌化合物的1H-NMR图表。
图3为式(2)所示的锌化合物的TG-DTA图表。
具体实施方式
下面,对本发明的氧化锌系膜形成用组合物进行说明。本发明的氧化锌系膜形成用组合物含有上述通式(1)所示的锌化合物作为必需成分。该锌化合物是可作为氧化锌前体化合物发挥功能的成分。在上述通式(1)中,作为R1及R2所示的碳原子数1~4的烷基的具体例,可以举出:甲基、乙基、丙基、异丙基、丁基、2-丁基、异丁基、叔丁基等。作为R1,从原料廉价的方面考虑,优选为甲基。另外,作为R2,优选相对于各种有机溶剂的溶解性良好且能形成稳定的组合物的甲基或乙基,进一步优选甲基。
在上述通式(1)所示的化合物中最优选的是上述式(2)所示的锌化合物。需要说明的是,上述式(2)所示的锌化合物为新型化合物。
本发明的氧化锌系膜形成用组合物中作为必需成分所含有的锌化合物例如可以通过下述方法制备:将下述通式(3)所示的酰基乙酸酯的锌络合物或其水合物与N,N,N’,N’-四甲基乙二胺混合。例如,上述式(2)所示的锌化合物可通过下述方法得到:将乙酰乙酸甲酯的锌络合物(水合物)与N,N,N’,N’-四甲基乙二胺于室温或加热下在有机溶剂中进行搅拌。
(在上述通式(3)中,R1及R2彼此独立地表示碳原子数1~4的烷基)
本发明的氧化锌系膜形成用组合物中也可以含有作为必需成分的特定的锌化合物以外的任意成分。作为本发明的氧化锌系膜形成用组合物的典型例子,可以举出:(a)含有上述通式(1)所示的锌化合物和能够使其分散或溶解的有机溶剂的组合物;(b)含有上述通式(1)所示的锌化合物、N,N,N’,N’-四甲基乙二胺和能够使这些成分溶解或分散的有机溶剂的组合物等。
在使乙酰乙酸酯的锌络合物的水合物(锌原料)和N,N,N’,N’-四甲基乙二胺在期望的有机溶剂中反应时,得到的氧化锌系膜形成用组合物中含有源自锌原料的水合水。可以从得到的氧化锌系膜形成用组合物中除去该水合水,也可以不除去。另外,相对于锌原料,使N,N,N’,N’-四甲基乙二胺过量地进行反应时,则得到的氧化锌系膜形成用组合物中含有过剩量的N,N,N’,N’-四甲基乙二胺。可以从得到的氧化锌系膜形成用组合物中除去该过剩量的N,N,N’,N’-四甲基乙二胺,也可以不除去。
本发明的氧化锌系膜形成用组合物中若含有适量的N,N,N’,N’-四甲基乙二胺,则组合物的稳定性良好,得到的膜的品质(氧化锌膜的情况下为透明性和导电性)提高,故优选。
在本发明的氧化锌系膜形成用组合物中,通常含有作为溶剂或分散剂的有机溶剂。该有机溶剂可以为单一溶剂,也可以为混合溶剂。作为有机溶剂,可以举出:醇系溶剂、二醇系溶剂、酮系溶剂、酯系溶剂、醚系溶剂、脂肪族或脂环族烃系溶剂、芳香族烃系溶剂、具有氰基的烃系溶剂及其它溶剂等。
作为醇系溶剂的具体例,可以举出:甲醇、乙醇、丙醇、异丙醇、1-丁醇、异丁醇、2-丁醇、叔丁醇、戊醇、异戊醇、2-戊醇、新戊醇、叔戊醇、己醇、2-己醇、庚醇、2-庚醇、辛醇、2-乙基己醇、2-辛醇、环戊醇、环己醇、环庚醇、甲基环戊醇、甲基环己醇、甲基环庚醇、苄醇、2-甲氧基乙醇、2-丁氧基乙醇、2-(2-甲氧基乙氧基)乙醇、1-甲氧基-2-丙醇、2-(N,N-二甲基氨基)乙醇、3-(N,N-二甲基氨基)丙醇等。
作为二醇系溶剂,可以举出:乙二醇、丙二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、1,5-戊二醇、新戊二醇、异戊二醇(3-甲基-1,3-丁二醇)、1,2-己二醇、1,6-己二醇、3-甲基-1,5-戊二醇、1,2-辛二醇、辛二醇(2-乙基-1,3-己二醇)、2-丁基-2-乙基-1,3-丙二醇、2,5-二甲基-2,5-己二醇、1,2-环己二醇、1,4-环己二醇、1,4-环己烷二甲醇等。
作为酮系溶剂,可以举出:丙酮、甲基乙基酮、甲基丁基酮、甲基异丁基酮、乙基丁基酮、二丙基酮、二异丁基酮、甲基戊基酮、环己酮、甲基环己酮等。
作为酯系溶剂,可以举出:甲酸甲酯、甲酸乙酯、乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸丁酯、乙酸异丁酯、乙酸仲丁酯、乙酸叔丁酯、乙酸戊酯、乙酸异戊酯、乙酸叔戊酯、乙酸苯酯、丙酸甲酯、丙酸乙酯、丙酸异丙酯、丙酸丁酯、丙酸异丁酯、丙酸仲丁酯、丙酸叔丁酯、丙酸戊酯、丙酸异戊酯、丙酸叔戊酯、丙酸苯酯、2-乙基己酸甲酯、2-乙基己酸乙酯、2-乙基己酸丙酯、2-乙基己酸异丙酯、2-乙基己酸丁酯、乳酸甲酯、乳酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸甲酯、甲氧基丙酸乙酯、乙氧基丙酸乙酯、乙二醇单甲醚乙酸酯、二乙二醇单甲醚乙酸酯、乙二醇单乙醚乙酸酯、乙二醇单丙醚乙酸酯、乙二醇单异丙基醚乙酸酯、乙二醇单丁醚乙酸酯、乙二醇单仲丁基醚乙酸酯、乙二醇单异丁基醚乙酸酯、乙二醇单叔丁基醚乙酸酯、丙二醇单甲醚乙酸酯、丙二醇单乙醚乙酸酯、丙二醇单丙醚乙酸酯、丙二醇单异丙基醚乙酸酯、丙二醇单丁醚乙酸酯、丙二醇单仲丁基醚乙酸酯、丙二醇单异丁基醚乙酸酯、丙二醇单叔丁基醚乙酸酯、丁二醇单甲醚乙酸酯、丁二醇单乙醚乙酸酯、丁二醇单丙醚乙酸酯、丁二醇单异丙基醚乙酸酯、丁二醇单丁醚乙酸酯、丁二醇单仲丁基醚乙酸酯、丁二醇单异丁基醚乙酸酯、丁二醇单叔丁基醚乙酸酯、乙酰乙酸甲酯、乙酰乙酸乙酯、丁酮酸甲酯、丁酮酸乙酯、γ-丁内酯、δ-戊内酯等。
作为醚系溶剂,可以举出:四氢呋喃、四氢吡喃,吗啉、乙二醇二甲醚、二乙二醇二甲醚、三乙二醇二甲醚、丁醚、乙醚、二烷等。
作为脂肪族或脂环族烃系溶剂,可以举出:戊烷、己烷、环己烷、甲基环己烷、二甲基环己烷、乙基环己烷、庚烷、辛烷、萘烷、溶剂石脑油等。
作为芳香族烃系溶剂,可以举出:苯、甲苯、乙基苯、二甲苯、均三甲苯、二乙基苯、异丙苯、异丁基苯、异丙基甲苯、四氢化萘等。
作为具有氰基的烃系溶剂,可以举出:1-氰基丙烷、1-氰基丁烷、1-氰基己烷,氰基环己烷、氰基苯、1,3-二氰基丙烷、1,4-二氰基丁烷、1,6-二氰基己烷、1,4-二氰基环己烷、1,4-二氰基苯等。
作为其它有机溶剂,可以举出:N-甲基-2-吡咯烷酮、二甲基亚砜、二甲基甲酰胺等。
上述有机溶剂中,醇系溶剂及酯系溶剂由于廉价,并且对于锌化合物显示出充分的溶解性,且作为涂布溶剂相对于硅基体、金属基体、陶瓷基体、玻璃基体、树脂基体等各种基体显示出良好的涂布性,故优选。另外,在使用混合溶剂的情况下,也更优选含有50质量%以上的醇系溶剂和酯系溶剂中的至少任一种。另外,优选沸点比转化为膜的温度低的有机溶剂,更优选沸点为150℃以下的有机溶剂。
本发明的氧化锌系膜形成用组合物的优选方式为:以上述通式(1)所示的锌化合物、N,N,N’,N’-四甲基乙二胺及有机溶剂作为必需成分,且溶解有锌化合物的溶液。氧化锌系膜形成用组合物中的锌化合物的浓度优选为形成稳定溶液的浓度。具体而言,氧化锌系膜形成用组合物中所含的锌化合物的比例优选为0.01~0.1mol/L。另外,氧化锌系膜形成用组合物中所含的N,N,N’,N’-四甲基乙二胺的量优选相对于锌化合物为2~20倍摩尔(mol)。需要说明的是,有机溶剂优选沸点为150℃以下的酯系溶剂和/或醇系溶剂。
根据需要,本发明的氧化锌系膜形成用组合物可以在不妨碍本发明效果的范围内含有上述成分以外的“其它成分”。作为其它成分,可以举出:抗胶凝剂、增溶剂、消泡剂、增稠剂、触变剂、及流平剂等改善组合物的稳定性及涂布性的添加剂;反应剂、反应助剂、交联助剂等成膜助剂。氧化锌系膜形成用组合物中所含的“其它成分”的比例优选分别为10质量%以下、更优选为5质量%以下。
例如,作为上述通式(1)所示的锌化合物的增溶剂,优选与锌化合物的配合基相同的酰基乙酸酯。氧化锌系膜形成组合物中所含的酰基乙酸酯的比例优选为0.05~5质量%。若酰基乙酸酯的含有比例低于0.05质量%,则有时无法得到作为增溶剂的效果。另一方面,即使酰基乙酸酯的含有比例超过5质量%,作为增溶剂的效果有时也不进一步提高,反而不经济。
另外,氧化锌系膜形成用组合物中优选含有可将作为前体化合物的锌化合物转化为氧化锌的氧化剂。作为氧化剂,优选水。水在锌化合物转化为氧化锌时发挥作用,有助于所形成的氧化锌系膜的高品质化。氧化锌系膜形成用组合物中所含的水的比例优选为1~10质量%。若水的含有比例低于1质量%,则有时无法得到使用水的效果。另一方面,若水的含有比例超过10质量%,则有时锌化合物易分解,成为发生凝胶化和固体生成等组合物变质的主要原因。可以预先在氧化锌系膜形成用组合物中添加需要量的水,也可以在制造氧化锌系膜之前添加。
接着,对本发明的氧化锌系膜的制造方法进行说明。本发明的氧化锌系膜的制造法为可有效地发挥上述氧化锌系膜形成用组合物的特征的方法。具体而言,本发明的氧化锌系膜的制造方法包括:(1)将上述的氧化锌系膜形成用组合物涂布在基体上形成涂布层的工序(以下也记作“涂布工序”);和(2)在150~300℃下对所形成的涂布层进行处理而转化为膜的工序(以下也记作“膜转化工序”)。
作为涂布工序中的氧化锌系膜形成用组合物的涂布方法,可以举出:旋涂法、浸渍涂布法、喷涂法、雾涂法、流涂法、幕式涂布法、辊涂法、刀涂法、棒涂法、丝网印刷法、刷涂等。另外,涂布有氧化锌系膜形成用组合物的基体的种类没有特别限定,可以举出:玻璃、硅等无机基体,聚酰亚胺、聚碳酸酯、聚对苯二甲酸乙二醇酯、聚萘二甲酸乙二醇酯等树脂基体等。
在150~300℃下、优选在200~300℃下对基体上所形成的涂布层进行处理,使锌化合物氧化而形成氧化锌系膜。需要说明的是,可以在涂布了氧化锌系膜形成用组合物后,于150~300℃下进行处理,也可以在涂布氧化锌系膜形成用组合物的同时于150~300下进行处理。即,涂布工序和膜转化工序也可以大致同时进行。为了在涂布氧化锌系膜形成用组合物的同时于150~300℃下进行处理,例如只要将基体预先设为期望的转化温度并在该基体上涂布氧化锌系膜形成用组合物即可。这样的方法可以应用于喷涂法及雾涂法。
膜转化工序的气氛优选存在氧、臭氧、二氧化氮、一氧化氮、水蒸气、过氧化氢、甲酸、乙酸、乙酸酐等氧化性物质的氧化性气氛。为了调节氧化性气氛,可以使用非活性气体作为稀释气体。
涂布氧化锌系膜形成用组合物后,为了使有机溶剂等低沸点成分气化,还优选设置干燥工序。另外,为了形成品质良好的氧化锌系膜,也可以在膜转化后,于非活性气氛下、氧化性气氛下或还原性气氛下进行退火处理。退火处理的温度通常为150~400℃、优选为150~300℃。
另外,为了将所形成的氧化锌系膜制成需要的膜厚,也可以重复进行多次涂布工序和膜转化工序。例如,可以将从涂布工序至膜转化工序为止重复多次,也可以将涂布工序和干燥工序分别重复多次。另外,在各自的工序中,也可以施加或照射等离子体、各种放射线等热以外的能量。
在本发明中,通过在氧化锌系膜形成用组合物中含有其它成分的前体、适宜选择各工序的条件或在各工序使用反应性气体等,可以形成氧化锌陶瓷、氧化锌和其它元素的复合氧化物、氧化锌和其它元素的复合膜等显示期望的特性的氧化锌系膜(薄膜)。
作为所制造的氧化锌系膜(薄膜)的种类,例如可以举出:氧化锌、锌-铟复合氧化物、铅-锌复合氧化物、铅-锌-铌复合氧化物、铋-锌-钽复合氧化物、锡-锌复合氧化物、添加锂的氧化锌、添加锌的铁素体等。另外,作为这些氧化锌系膜(薄膜)的用途,例如可以举出:半导体、透明导体、发光体、荧光体、光催化剂、磁性体、导体、电极、高介电体、强介电体、压电体、微波电介质、光波导、光放大器、光开关、电磁屏蔽、太阳能电池等。
实施例
下面,以实施例进一步详细地说明本发明。但是,本发明并不受以下实施例的任何限制。
(1)式(2)所示的锌化合物的制造
[实施例1]
将氯化锌1摩尔份、甲醇钠2摩尔份及相对于氯化锌为8倍质量的甲醇混合,并将得到的反应液于室温下搅拌30分钟。滤除析出的氯化钠。将得到的滤液加入含有乙酰乙酸甲酯2摩尔份和为乙酰乙酸甲酯的3倍质量的甲醇的溶液中,在室温下搅拌30分钟。滤取析出的结晶后,用甲醇清洗及干燥,作为中间体,以收率95%得到锌的乙酰乙酸甲酯络合物。将该中间体1摩尔份及N,N,N’,N’-四甲基乙二胺1摩尔份加入相对于中间体为1倍质量的己烷中,在加热回流下搅拌1小时。将得到的溶液进行过滤,在-30℃下进行重结晶处理,以收率97%得到目标物即式(2)所示的锌化合物(白色结晶)。对得到的白色结晶进行IR、1H-NMR、及TG-DTA测定。将得到的IR图表示于图1、1H-NMR图表示于图2、及TG-DTA图表示于图3。需要说明的是,测定条件如下所示。
〈IR测定〉
测定装置:商品名“Nicolet6700”(ThermoFisherScientific公司制)
〈1H-NMR测定〉
测定装置:商品名“JNM-ECA400”(日本电子公司制),频率:400MHz,溶剂:重苯
〈TG-DTA〉
测定装置:商品名“EXSTRA6000”(SIINanotechnology公司制,样品量:6mg,空气:300mL/mL,升温速度10℃/分钟,参比物:氧化铝)
(2)氧化锌系膜形成用组合物的制备
[实施例2]
使实施例1中得到的式(2)所示的锌化合物溶解在乙酸甲酯中,制备了氧化锌系膜形成用组合物(实施例2)。另外,式(2)所示的锌化合物的浓度为0.05mol/L。
[实施例3~9、比较例1~10]
混合表1所示的各成分,制备了氧化锌系膜形成用组合物(实施例3~9、比较例1~10)。需要说明的是,将式(4)所示的锌成分及式(5)所示的锌成分如下所示。
表1
*1:双(戊烷-2,5-二酮基)锌(bis(pentane-2,5-dionato)zinc)
*2:N,N,N’,N’-四甲基乙二胺
*3:三乙胺
*4:乙二胺
*5:乙醇胺
*6:2-甲氧基乙胺
*7:N-甲基乙醇胺
*8:N,N-二甲基乙醇胺
*9:乙二醇二甲醚
*10:2-甲氧基乙醇
(3)氧化锌系膜的制造
[实施例10~17、比较例11~20]
使用实施例2~9及比较例1~10中得到的各自的氧化锌系膜形成用组合物在以下条件下形成锌系氧化膜。在用热板加热为200℃的4cm见方的玻璃基板上通过喷雾喷上各自的氧化锌系膜形成用组合物。将喷雾1次的喷雾量设为0.1mL,重复喷雾200次,总计喷雾20mL。喷雾后,将玻璃基板在200℃下保持30分钟形成膜,得到带膜的玻璃基板。
目视观察得到的带膜玻璃基板,评价所形成的膜的均质性。将评价结果示于表2及3。关于评价基准,将涂膜不均的情况设为“不均”,将有凝聚物的情况设为“有凝聚物”,将均质的情况设为“均质”。需要说明的是,将未得到膜的情况设为“无膜”。
另外,评价形成的膜的透明性及导电性。透明性使用浊度计(商品名“NDH2000”(日本电色工业公司制)),通过利用D65光源测定总光线透射率进行评价。另外,导电性使用商品名“Loresta-EPMCP-T360”(三菱化学公司制),通过利用四探针法测定体积电阻率进行评价。需要说明的是,体积电阻率在任意多个测定点进行测定,用平均值表示。需要说明的是,将测定值超过作为测定界限的107Ω·cm的情况表示为“∞”。将透射率及电阻率的测定结果示于表2及3。
进而,测定所形成的膜的雾度及膜厚。雾度使用浊度计(商品名“NDH2000”(日本电色工业公司制))进行测定。另外,使用FE-SEM测定膜的中央部的厚度。将雾度及膜厚的测定结果示于表2及3。
表2
表3
如表2及3所示,可以确认在使用实施例2~9中得到的氧化锌系膜形成用组合物的情况下,即使在于200℃下进行处理的情况下,也可形成均质且透明的氧化锌系膜。相比之下,在使用比较例1~10中得到的氧化锌系膜形成用组合物的情况下,未能形成良好的膜。另外,所形成的膜的电阻率也很高,以至于无法测定。
工业实用性
使用本发明的氧化锌系膜形成用组合物,可以容易地形成例如半导体、透明导体、发光体、荧光体、光催化剂、磁性体、导体、电极、高介电体、强介电体、压电体、微波电介质、光波导、光放大器、光开关、电磁屏蔽、太阳能电池等中所使用的氧化锌系膜。
Claims (5)
1.一种氧化锌系膜形成用组合物,其含有下述通式(1)所示的锌化合物作为必需成分,还含有N,N,N’,N’-四甲基乙二胺、沸点为150℃以下的酯系溶剂和/或醇系溶剂,
在所述通式(1)中,R1及R2彼此独立地表示碳原子数1~4的烷基,
所述氧化锌系膜形成用组合物中所含的N,N,N’,N’-四甲基乙二胺的量相对于锌化合物为2~20倍摩尔。
2.如权利要求1所述的氧化锌系膜形成用组合物,其中,所述通式(1)中的R1及R2为甲基。
3.如权利要求1或2所述的氧化锌系膜形成用组合物,其中,所述锌化合物的含有比例为0.01~0.1mol/L。
4.如权利要求1或2所述的氧化锌系膜形成用组合物,其还含有0.05~5质量%的酰基乙酸酯。
5.一种氧化锌系膜的制造方法,其包括:
将权利要求1或2所述的氧化锌系膜形成用组合物涂布在基体上形成涂布层的工序;和
在150~300℃下对所述涂布层进行处理而转化为膜的工序。
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