KR900003453B1 - 불소처리 산화주석 피막 형성용 불소함유 유기주석 화합물 - Google Patents
불소처리 산화주석 피막 형성용 불소함유 유기주석 화합물 Download PDFInfo
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- KR900003453B1 KR900003453B1 KR1019880700299A KR880700299A KR900003453B1 KR 900003453 B1 KR900003453 B1 KR 900003453B1 KR 1019880700299 A KR1019880700299 A KR 1019880700299A KR 880700299 A KR880700299 A KR 880700299A KR 900003453 B1 KR900003453 B1 KR 900003453B1
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- Prior art keywords
- tin oxide
- compound
- tin
- trifluoroacetic acid
- compounds containing
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 28
- 229910052731 fluorine Inorganic materials 0.000 title abstract description 10
- 239000011737 fluorine Substances 0.000 title abstract description 10
- 238000000576 coating method Methods 0.000 title abstract description 5
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 title abstract description 5
- 229910001887 tin oxide Inorganic materials 0.000 title abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 title abstract 2
- 239000011248 coating agent Substances 0.000 title 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 48
- -1 butyltin chloride bis-trifluoroacetate Chemical compound 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- MBKHKMOVCKNRHB-UHFFFAOYSA-K C(C)(=O)O.C(CCC)[Sn](Cl)(Cl)Cl Chemical compound C(C)(=O)O.C(CCC)[Sn](Cl)(Cl)Cl MBKHKMOVCKNRHB-UHFFFAOYSA-K 0.000 claims 1
- YXPSLKXRUCMRIN-UHFFFAOYSA-L butyl(dichloro)stannanylium;2,2,2-trifluoroethanolate Chemical compound [O-]CC(F)(F)F.CCCC[Sn+](Cl)Cl YXPSLKXRUCMRIN-UHFFFAOYSA-L 0.000 claims 1
- FYDLBBUBQFJOJT-UHFFFAOYSA-L butyl(dichloro)tin Chemical compound CCCC[Sn](Cl)Cl FYDLBBUBQFJOJT-UHFFFAOYSA-L 0.000 claims 1
- SYAXPJDYXAPBDK-UHFFFAOYSA-L dichloro(ethyl)tin Chemical compound CC[Sn](Cl)Cl SYAXPJDYXAPBDK-UHFFFAOYSA-L 0.000 claims 1
- YSCVYRUCAPMZFG-UHFFFAOYSA-K trichlorotin Chemical group Cl[Sn](Cl)Cl YSCVYRUCAPMZFG-UHFFFAOYSA-K 0.000 claims 1
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 abstract description 10
- 238000005229 chemical vapour deposition Methods 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 5
- GGBFOKTZTGOTFG-UHFFFAOYSA-K [butyl(dichloro)stannyl] 2,2,2-trifluoroacetate Chemical compound CCCC[Sn](Cl)(Cl)OC(=O)C(F)(F)F GGBFOKTZTGOTFG-UHFFFAOYSA-K 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical class Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- NPNMHHNXCILFEF-UHFFFAOYSA-N [F].[Sn]=O Chemical compound [F].[Sn]=O NPNMHHNXCILFEF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- FAOSYNUKPVJLNZ-UHFFFAOYSA-N butylstannane Chemical compound CCCC[SnH3] FAOSYNUKPVJLNZ-UHFFFAOYSA-N 0.000 description 3
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- QLWWJOOITQGSQE-UHFFFAOYSA-K dichloro(phenyl)stannanylium;hydroxide Chemical compound [OH-].Cl[Sn+](Cl)C1=CC=CC=C1 QLWWJOOITQGSQE-UHFFFAOYSA-K 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- QRRCTLYMABZQCS-IHWYPQMZSA-N (z)-4,4,4-trifluoro-3-methylbut-2-enoic acid Chemical compound FC(F)(F)C(/C)=C\C(O)=O QRRCTLYMABZQCS-IHWYPQMZSA-N 0.000 description 1
- QVXZSAWOXGFNIK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropan-2-ol Chemical compound FC(F)(F)C(F)(O)C(F)(F)F QVXZSAWOXGFNIK-UHFFFAOYSA-N 0.000 description 1
- FQDXJYBXPOMIBX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-methylpropan-2-ol Chemical compound FC(F)(F)C(O)(C)C(F)(F)F FQDXJYBXPOMIBX-UHFFFAOYSA-N 0.000 description 1
- OCGWWLDZAFOHGD-UHFFFAOYSA-N 1,1,1-trifluoro-2-methylpropan-2-ol Chemical compound CC(C)(O)C(F)(F)F OCGWWLDZAFOHGD-UHFFFAOYSA-N 0.000 description 1
- GILIYJDBJZWGBG-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-ol Chemical compound CC(O)C(F)(F)F GILIYJDBJZWGBG-UHFFFAOYSA-N 0.000 description 1
- GVEMIUUOJFZCOD-UHFFFAOYSA-N 1-fluoro-2-methylpropan-2-ol Chemical compound CC(C)(O)CF GVEMIUUOJFZCOD-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- XETRHNFRKCNWAJ-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropanoate Chemical compound FC(F)(F)C(F)(F)C(=O)OC(=O)C(F)(F)C(F)(F)F XETRHNFRKCNWAJ-UHFFFAOYSA-N 0.000 description 1
- WXJFKAZDSQLPBX-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)F WXJFKAZDSQLPBX-UHFFFAOYSA-N 0.000 description 1
- JUGSKHLZINSXPQ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoropentan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)F JUGSKHLZINSXPQ-UHFFFAOYSA-N 0.000 description 1
- MNAXKZBNGJCPED-UHFFFAOYSA-N 2,2-difluoroacetic acid hydrochloride Chemical compound Cl.OC(=O)C(F)F MNAXKZBNGJCPED-UHFFFAOYSA-N 0.000 description 1
- GGDYAKVUZMZKRV-UHFFFAOYSA-N 2-fluoroethanol Chemical compound OCCF GGDYAKVUZMZKRV-UHFFFAOYSA-N 0.000 description 1
- KSNKQSPJFRQSEI-UHFFFAOYSA-M 3,3,3-trifluoropropanoate Chemical class [O-]C(=O)CC(F)(F)F KSNKQSPJFRQSEI-UHFFFAOYSA-M 0.000 description 1
- MGAUIBBIERLJFJ-UHFFFAOYSA-N 3-fluorooxane-2,6-dione Chemical compound FC1CCC(=O)OC1=O MGAUIBBIERLJFJ-UHFFFAOYSA-N 0.000 description 1
- HSXMRBZVQXUROA-UHFFFAOYSA-N 3-fluorooxolane-2,5-dione Chemical compound FC1CC(=O)OC1=O HSXMRBZVQXUROA-UHFFFAOYSA-N 0.000 description 1
- SGNZYJXNUURYCH-UHFFFAOYSA-N 5,6-dihydroxyindole Chemical compound C1=C(O)C(O)=CC2=C1NC=C2 SGNZYJXNUURYCH-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JGAVRQUPAFDAQC-UHFFFAOYSA-N FC(C(=O)O)(F)F.C(C)(=O)OCCCC Chemical compound FC(C(=O)O)(F)F.C(C)(=O)OCCCC JGAVRQUPAFDAQC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XEKAUTDWPYQNFU-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl XEKAUTDWPYQNFU-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- DIVTWACHZOQOBF-UHFFFAOYSA-K diacetyloxy(butyl)stannanylium;acetate Chemical compound CCCC[Sn](OC(C)=O)(OC(C)=O)OC(C)=O DIVTWACHZOQOBF-UHFFFAOYSA-K 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- QXOAMRBDPILTFX-UHFFFAOYSA-L dichloro(pentyl)tin Chemical compound CCCCC[Sn](Cl)Cl QXOAMRBDPILTFX-UHFFFAOYSA-L 0.000 description 1
- GXWLHTAAGCHDAV-UHFFFAOYSA-L dichloro-bis(2-methylpropyl)stannane Chemical compound CC(C)C[Sn](Cl)(Cl)CC(C)C GXWLHTAAGCHDAV-UHFFFAOYSA-L 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- ZULTVNRFZRQYKL-UHFFFAOYSA-M fluorotin Chemical compound [Sn]F ZULTVNRFZRQYKL-UHFFFAOYSA-M 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- UFFSXJKVKBQEHC-UHFFFAOYSA-N heptafluorobutyric anhydride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(=O)OC(=O)C(F)(F)C(F)(F)C(F)(F)F UFFSXJKVKBQEHC-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- CXZGQIAOTKWCDB-UHFFFAOYSA-N perfluoropentanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CXZGQIAOTKWCDB-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- PDFNMVKYZSDSLJ-UHFFFAOYSA-K trichloro(2-methylpropyl)stannane Chemical compound CC(C)C[Sn](Cl)(Cl)Cl PDFNMVKYZSDSLJ-UHFFFAOYSA-K 0.000 description 1
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
-
- 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
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/40—Oxides
- C23C16/407—Oxides of zinc, germanium, cadmium, indium, tin, thallium or bismuth
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/004—Aftersun preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
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Abstract
내용 없음.
Description
[발명의 명칭]
불소처리 산화주석 피막 형성용 불소함유 유기주석 화합물
[발명의 상세한 설명]
본 발명은 불소처리(Fluorine doped) 산화주석 피막 형성에 유용한 불소함유 유기주석 화합물에 관한 것이다.
다음에 기술된 공지문헌들은 본 발명 화합물과 관련된 화합물에 대하여 기술하고 있으나 이들 화합물은 화학 증착법을 위한 액상 피막형성 조성물에 대해서는 기술하고 있지 않다.
미국특허 3,759,743에서 멘케는 트리플루오로 초산의 비 할로겐화 유기주석염의 제조 및 분무용액법에 의한 불소주석 피막 제조용으로서 메틸 에틸 케톤 같은 유기 용매내의 상기 조성물에 대하여 기술하였다.
그러나 이 전구물질들은 낮은 휘발성을 가지며 또한 용매를 첨가하지 않는 좀더 유리한 화학 증착방법에는 적합하지 않다.
케미칼콤뮤니케이션스(Chemical Communications)(1970) 151페이지 및 J.Organomet. Chem. 38(1972) 287페이지에 왕 및 스리브는 트리플루오로 초산의 디 알킬 염화 주석염의 제조에 대하여 기술하였다. 불행하게도, 상기 화합물들은 화학 증착방법에 사용할 수 없는 고체상이다.
미국특허 4,254,046에서 프란즈 등은 불소처러 산화주석 피막의분말 침착(powder deposition)용 디알킬 주석 디 플루오라이드에 대하여 기재하였다.
프랑스특허 1,400,314에서 톰프슨은 트리플루오로 초산의 모노-, 디-및 트리 알킬 주석염 및 그들의 제조에 대하여 기술하였다.
Organic preparation and Procedure 1(3) 173-176(1969)에서 리버르, 라이프, 데이빗슨은 폴리 플루오로카복실산의 디 알킬 주석염의 제조에 대하여 기술하였다.
J.Organomet, Chem., (3) 151(1970)에서는 트리플루오로메틸 초산의 디알킬 염화주석 염에 대하여 기술하였다.
J.Organomet, Chem. 3972(1971) 에서는 트리알킬주석과 플루오로알킬 옥사이드에 대하여 기술하였다.
상기 문헌들에서는 특히 액상 피막 조성물로부터의 화학 증착법에 유용한 유기주석 전구물질에 대해서는 기재하고 있지 않다. 더욱이 상기 문헌들은 모노알킬 또는 관련된 치환체 및 주석원자의 직접 결합된 적어도 하나의 염소원자 및 적어도 하나의 트리풀루오로 메틸 포함기를 갖는 유기주석 화합물은 기재하지 않았다.
따라서 본 발명의 목적은 저 박판저항(低薄板抵抗)을 갖는 불소 처리 산화주석 피막 형성에 직접적으로 사용할 수 있는 새롭고 개선된 유기주석 화합물을 제공하는 것이다.
본 발명의 또 다른 목적은 화학 증착방법에 의해 불소처리 산화주석피막을 제조하는데 사용할 수 있는 화합물 들을 제공하는 것이다.
본 발명의 또 다른 목적은 불소 산화주석 피막의 화학 증착법에 사용되는 유리한 액상 피막 조성물에 사용할 수 있는 트리플루오로 초산의 모노알킬 염화주석을 제조하는 것이다.
본 발명은 다음 일반식을 갖는 불소함유 유기화합물에 관한 것이다.
상기에서 R은 C1-2알킬 : 아릴 : 또는 카르발콕시알킬 a=1 ; b=1, 2 ; c=0, 1 ; d=0, 1 ; e=0-2 ; f=1, 2 ; 및 n=1-6 ; 이고 a+b+c+d=4이다.
표 1에 a, b, c, f, d, e 및 n의 각 경우에 대한 상기 일반식하에서 본 발명의 화합물을 요약하였다. 상기화합물을 제조하는데 사용한 반응물질도 기재하였다.
[표 1a][출발 물질]
[표 1b]
[표 1c]
따라서, 본 발명의 바람직한 화합물은 다음 화합물을 포함한다.
화합물 구조식
1.트리플루오로초산의 부틸 2염화주석염 C4HyCl3SnOCOCF3
2.트리플루오로초산의 부틸 염화주석염 C4HyClSn(OCOCF3)2
3.부틸 염화주석 아세테이트 트리플루오로아세테이트CtHyClSn(OCOCH3)(OCOCF3)
4.트리플루오로초산의 카르브에톡시에틸 2염화주석염CH3CH2OCOCH2CH2Cl2Sn(OCOCF3)
5.부틸 2염화주석 트리플루오로에톡사이드 CtHyCl2SnOCH2CF3
6.트리플루오로초산의 3염화주석염 SnCl3OCOCF3
[발명의 최선실시형태]
본 발명 화합물은 다음과 같이 제조할 수 있다.
반응 일반식
RaSnClb+1(OCOCH3)c+[O(CO)d(CH2)e(CnF2n+1)]fM+환류
RaSnClb(OCOCH3)c[O(CO)d(CH2)e(CnF2n+1)]f+M+Cl-
상기에서 M+는 양이온이다.
본 발명에서 "알킬이란 1-6개의 탄소원자를 갖는 직쇄 및 측쇄의 알칼기를 포함하고, 유기주석 화합물은 4염화주석을 포함한다.
따라서 본 발명 화합물의 제조에 사용되는 대표적인 유기주석 반응 물질은 3염화 모노부틸주석, 3염화 이소부틸주석, 3염화 메틸주석, 2염화 디부틸주석, 2염화 디이소부틸주석, 2염화 디 t-부틸주석 초산의 부틸 2염화주석염 및 3염화 카르브에톡시에틸주석 및 4염화 주석을 포함한다.
불소반응물질은, 카복실산, 무수물, 산할라이드 또는 알콜로부터 선택된 탄소가 산소와 결합된 기능기의 α또는 β 위치에 트리플루오로메틸기를 갖는다.
따라서, 적합한 불소 반응 물질은 다음을 포함한다.
카복실산
트리플루오로 초산
염화 디플루오로 초산
디 플루오로 초산
헵타 플루오로 부티르산
펜타 플루오로 프로피온산
3-트리플루오로 메틸크로톤산
노나플루오로 펜탄산
무수물
트리플루오로 초산 무수물
헵타 플루오로 부티르산 무수물
펜타 플루오로 프로피온산 무수물
염화 디플루오로 초산 무수물
과 플루오로 글루타르 산 무수물
과 플루오로 숙신산 무수물
산 할라이드
헵타 플루오로 부티릴 클로라이드
과 플루오로 글루타릴 플루오라이드
과 플루오로 옥타노일 플루오라이드
과 플루오로 숙신닐 클로라이드
알콜
2, 2, 2-트리플루오로 에탄올
1H, 1H-헵타 플루오로 부탄올-1
3, 3, 4, 4, 5, 5-헵타 플루오로 페탄올-2
헵타 플루오로 이소프로판올
헥사 플루오로-2-메틸 이소 프로판올
1H, 1H, 5H-옥타 플루오로-1-펜탄올
과 플루오로-t-부탄올
2-트리플루오로메틸 프로판올-2
1, 1, 1-트리플루오로 프로판올-2
과 플루오로 에탄올
본 발명의 바람직한 실시태양은 3염화 모노부틸 주석과 트리플루오로 초산이 반응하여 트리플루오로 초산의 부틸 2염화 주석염이 생성되는 것이다.
본 발명은 다음의 실시예에 의해 설명되어 질 것이다.
[실시예 1]
3염화 모노부틸주석과 트리플루오로 초산과의 반응물 : 트리플루오로 초산의 모노부틸 2염화 주석염의 제조.
CtHySnCl3+CF3COOK+-CtHyCl2SnOCOCF3+KCl
A : KOH를 물에 용해시키고 트리플루오로 초산(TFA)을 가하여 제 1 용액을 제조하고 따로 삼염화 모노부틸주석(MBTC), 에테르 및 메틸에틸케톤(MEK)을 체우고 N+Br-를 가한 제 2 용액을 제조한 후, 제 1 용액에 제 2 용액을 가하고 질소하에 교반하여 환류온도까지 가열한 후 48℃에서 2시간 동안 환류시켜서, MBTC 8.46g(0.03mole, 71.2중량%) 및 TFA 3.42g(0.03mole, 28.8중량%), KOH 2.08g(0.03mole), 15ml의 H2O, 50ml의 에테르, 50ml의 MEK 및 상이전촉매(M+Br-)로서 0.1g의 C16H33(CH3)3N+Br+의 반응 혼합물을 생성시켰다. 1주야 방치후, 수상(水相) 및 유기상(有機相)이 형성되었다. 수상은 맑고 무색의 저층이었고, 유기상은 맑고 황색의 상층이었다. 유기층을 농축시키고 잔사를 진공 데시케이터에서 1주야 방치시켰다. 갈색점성의 액상인 트리플루오로 초산의 모노부틸 2염화 주석염이 9.6g 생성되었다.(89% 수율)
주석 염소
분석치 33% 20%
실측치 36% 21%
B : 삼염화 모노부틸 주석 200g(0.7mole) 및 트리플루오로 초산 소디움염 10g(0.07mole)의 반응 혼합물을 70℃에서 3시간 동안 가열시키고 실은에서 1주야 방치시켰다. 부생물인 소디움 클로라이드와 미반응의 소디움염을 여과시켰다. 액상의 피막 조성물은 약 12중량%의 트리플루오로 초산의 모노부틸 2염화주석염 및 88중량%의 모노부틸주석 트리클로라이드이 었다.
[실시예 2]
모노페닐 디클로로주석 하이드록사이드와 트리플루오로 초산의 반응 생성물 : 모노 폐닐 디클로로주석 트리플루오로 아세테이트의 제조.
모노 페닐 디클로로주석 하이드록사이드 9.0g(0.03mole)와 트러플루오로 초산 3.42g(0.03mole)의 반응 혼합물을 실시예 1의 방법에 따라 제조하였고 2시간 동안 환류시킨 결과 81%의 소당 화합들이 생성되었다.
[실시예 3]
실시예 2의 실험을 트리플루오로 초산의 암모늄염을 사용하실시한 결과 유사한 결과를 얻었다.
[실시예 4]
불소 처리 산화주석 피막의 제조
실시예 1B의 액상고팅조성물을 화학증착법에 의한 유리의 불소 산화주석 피막 제조에 사용하였다.
수분을 포함하는 대기에서, 650℃에서 2초 동안 침착시켜 투명하고 트림이 없는 200mm 두께의 피막을 생성시켰다. 박판저항은 약 40옴(ohm)/스퀘어이었다. 적외선 반사율은 10마이크론에서 70% 이상이었고 가시광선 투과율은 70% 이상이었다.
Claims (8)
- 다음 구조식의 화합물
상기에서 R은 알킬 : 아릴 또는 카르브알콕시 알킬 : a는 1, b는 1, 2, c는 0, 1, d는 0, 1, e는 0-2, f는 1, 2, n은 1-6이고 a+b+c+d=4이다. - 제 1 항에 있어서, R은 C1-6의 알킬인 화합물.
- 제 1 항에 있어서, 트리플루오로 초산의 부틸 2염화주석인 화합물.
- 제 1 항에 있어서, 부틸 염화주석 비스-트리 플루오로아세테이트인 화합물.
- 제 1 항에 있어서, 부틸 염화주석 아세테이트 트리플루오로 아세테이트인 화합물.
- 제 1 항에 있어서, 카르브에톡시 에틸 2염화주석 트리플루오로 아세테이트인 화합물.
- 제 1 항에 있어서, 부틸 2염화주석 트리플루오로 에톡사이드인 화합물.
- 트리플루오로 초산의 3염화 주석인 화합물.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/888,298 US4731462A (en) | 1986-07-18 | 1986-07-18 | Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating |
| PCT/US1987/001746 WO1988000588A1 (en) | 1986-07-18 | 1987-07-17 | Organotin compounds containing fluorine useful for forming fluorine-doped tin oxide coating |
| US888298 | 2001-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR880701724A KR880701724A (ko) | 1988-11-04 |
| KR900003453B1 true KR900003453B1 (ko) | 1990-05-19 |
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|---|---|---|---|
| KR1019880700299A KR900003453B1 (ko) | 1986-07-18 | 1987-07-17 | 불소처리 산화주석 피막 형성용 불소함유 유기주석 화합물 |
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|---|---|
| US (1) | US4731462A (ko) |
| EP (1) | EP0318486B1 (ko) |
| JP (1) | JPH02500974A (ko) |
| KR (1) | KR900003453B1 (ko) |
| CN (1) | CN1051088C (ko) |
| AT (1) | ATE63918T1 (ko) |
| AU (1) | AU609734B2 (ko) |
| BR (1) | BR8707749A (ko) |
| CA (1) | CA1276160C (ko) |
| DE (1) | DE3770472D1 (ko) |
| DK (1) | DK167875B1 (ko) |
| EG (1) | EG19792A (ko) |
| ES (1) | ES2007080A6 (ko) |
| IL (1) | IL83178A (ko) |
| IN (1) | IN168762B (ko) |
| NO (1) | NO171068C (ko) |
| TR (1) | TR24843A (ko) |
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| DE4325648C1 (de) * | 1993-07-30 | 1994-09-08 | Goldschmidt Ag Th | Alkylzinnverbindungen, deren Herstellung und diese enthaltende Mittel zur Bildung elektrisch leitfähiger und IR-reflektierender Schichten auf Oberflächen von Glas, Glaskeramik oder Email |
| DE4433206A1 (de) * | 1994-09-17 | 1996-03-21 | Goldschmidt Ag Th | Verfahren zur pyrolytischen Beschichtung von Glas-, Glaskeramik- und Emailprodukten |
| US5725904A (en) * | 1995-06-02 | 1998-03-10 | Elf Atochem North America, Inc. | Liquid methyltin halide compositions |
| US5698262A (en) * | 1996-05-06 | 1997-12-16 | Libbey-Owens-Ford Co. | Method for forming tin oxide coating on glass |
| FR2795745B1 (fr) * | 1999-06-30 | 2001-08-03 | Saint Gobain Vitrage | Procede de depot d'une couche a base de tungstene et/ou de molybdene sur un substrat verrier, ceramique ou vitroceramique, et substrat ainsi revetu |
| EP1555696B1 (en) | 2002-10-25 | 2010-12-15 | Nakajima Glass Co., Inc. | Solar battery module manufacturing method |
| WO2005104242A1 (ja) * | 2004-04-27 | 2005-11-03 | Nakajima Glass Co., Inc. | 太陽電池モジュールの製造方法 |
| US7947374B2 (en) * | 2009-02-19 | 2011-05-24 | Guardian Industries Corp. | Coated article with sputter-deposited transparent conductive coating capable of surviving harsh environments, and method of making the same |
| US20100209730A1 (en) * | 2009-02-19 | 2010-08-19 | Guardian Industries Corp., | Coated article with sputter-deposited transparent conductive coating for refrigeration/freezer units, and method of making the same |
| US8097342B2 (en) | 2009-02-19 | 2012-01-17 | Guardian Industries Corp. | Coated article with sputter-deposited transparent conductive coating capable of surviving harsh environments, and method of making the same |
| US9625723B2 (en) * | 2013-06-25 | 2017-04-18 | Microsoft Technology Licensing, Llc | Eye-tracking system using a freeform prism |
| US10228561B2 (en) * | 2013-06-25 | 2019-03-12 | Microsoft Technology Licensing, Llc | Eye-tracking system using a freeform prism and gaze-detection light |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495783A1 (de) * | 1964-03-07 | 1969-04-03 | Hoechst Ag | Verfahren zur Herstellung von Polyaethylenterephthalat |
| US3836444A (en) * | 1968-10-01 | 1974-09-17 | Inst Francais Du Petrole | Process for polymerizing conjugated diolefins using organic compounds of the transition metals as catalysts |
| US3781315A (en) * | 1971-07-09 | 1973-12-25 | Prod Res & Chem Corp | Halo alkoxy metal compounds |
| US3775453A (en) * | 1972-03-14 | 1973-11-27 | Schaper | Preparation of hexafluoroisopropoxides of aluminum and group iv elements |
| DE3010077C2 (de) * | 1980-03-15 | 1981-07-30 | Vereinigte Glaswerke Gmbh, 5100 Aachen | Verfahren zum Aufbringen von mit einem Halogen, vorzugsweise mit Fluor dotierten Zinnoxidschichten auf Glasoberflächen durch Pyrolyse |
-
1986
- 1986-07-18 US US06/888,298 patent/US4731462A/en not_active Expired - Lifetime
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1987
- 1987-07-13 EG EG40987A patent/EG19792A/xx active
- 1987-07-13 ZA ZA875095A patent/ZA875095B/xx unknown
- 1987-07-13 IL IL83178A patent/IL83178A/xx unknown
- 1987-07-16 IN IN550/CAL/87A patent/IN168762B/en unknown
- 1987-07-17 CN CN87104911A patent/CN1051088C/zh not_active Expired - Fee Related
- 1987-07-17 AT AT87905098T patent/ATE63918T1/de not_active IP Right Cessation
- 1987-07-17 DE DE8787905098T patent/DE3770472D1/de not_active Expired - Fee Related
- 1987-07-17 EP EP87905098A patent/EP0318486B1/en not_active Expired - Lifetime
- 1987-07-17 ES ES8702098A patent/ES2007080A6/es not_active Expired
- 1987-07-17 BR BR8707749A patent/BR8707749A/pt not_active IP Right Cessation
- 1987-07-17 WO PCT/US1987/001746 patent/WO1988000588A1/en active IP Right Grant
- 1987-07-17 JP JP62504611A patent/JPH02500974A/ja active Granted
- 1987-07-17 TR TR87/0502A patent/TR24843A/xx unknown
- 1987-07-17 AU AU77837/87A patent/AU609734B2/en not_active Ceased
- 1987-07-17 KR KR1019880700299A patent/KR900003453B1/ko not_active IP Right Cessation
- 1987-07-17 CA CA000542377A patent/CA1276160C/en not_active Expired - Lifetime
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1988
- 1988-03-11 DK DK137088A patent/DK167875B1/da active
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Also Published As
| Publication number | Publication date |
|---|---|
| CN1051088C (zh) | 2000-04-05 |
| DK167875B1 (da) | 1993-12-27 |
| JPH0575756B2 (ko) | 1993-10-21 |
| KR880701724A (ko) | 1988-11-04 |
| CN87104911A (zh) | 1988-05-11 |
| EP0318486B1 (en) | 1991-05-29 |
| US4731462A (en) | 1988-03-15 |
| AU7783787A (en) | 1988-02-10 |
| DK137088D0 (da) | 1988-03-11 |
| WO1988000588A1 (en) | 1988-01-28 |
| EG19792A (en) | 1996-02-29 |
| CA1276160C (en) | 1990-11-13 |
| DK137088A (da) | 1988-03-11 |
| NO881186L (no) | 1988-03-17 |
| NO171068C (no) | 1993-01-20 |
| BR8707749A (pt) | 1989-08-15 |
| ES2007080A6 (es) | 1989-06-01 |
| IL83178A (en) | 1992-02-16 |
| TR24843A (tr) | 1992-06-19 |
| IN168762B (ko) | 1991-06-01 |
| JPH02500974A (ja) | 1990-04-05 |
| IL83178A0 (en) | 1987-12-31 |
| ZA875095B (en) | 1988-01-13 |
| NO171068B (no) | 1992-10-12 |
| EP0318486A1 (en) | 1989-06-07 |
| AU609734B2 (en) | 1991-05-09 |
| DE3770472D1 (de) | 1991-07-04 |
| NO881186D0 (no) | 1988-03-17 |
| ATE63918T1 (de) | 1991-06-15 |
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