DE69906593T2 - Verfahren zur herstellung von 8-chinolinolato metallkomplexen - Google Patents
Verfahren zur herstellung von 8-chinolinolato metallkomplexen Download PDFInfo
- Publication number
- DE69906593T2 DE69906593T2 DE69906593T DE69906593T DE69906593T2 DE 69906593 T2 DE69906593 T2 DE 69906593T2 DE 69906593 T DE69906593 T DE 69906593T DE 69906593 T DE69906593 T DE 69906593T DE 69906593 T2 DE69906593 T2 DE 69906593T2
- Authority
- DE
- Germany
- Prior art keywords
- aluminum
- hydroxyquinoline
- metal
- yellow
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229910052751 metal Inorganic materials 0.000 title claims description 36
- 239000002184 metal Substances 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 26
- 229910052782 aluminium Inorganic materials 0.000 claims description 38
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 29
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 26
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 26
- 229960003540 oxyquinoline Drugs 0.000 claims description 26
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 claims description 26
- -1 8-hydroxyquinoline compound Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 claims description 18
- 229940063655 aluminum stearate Drugs 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 150000007942 carboxylates Chemical class 0.000 claims description 17
- 239000007983 Tris buffer Substances 0.000 claims description 16
- 239000003446 ligand Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 13
- 150000004325 8-hydroxyquinolines Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004246 zinc acetate Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 238000010992 reflux Methods 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 238000004020 luminiscence type Methods 0.000 description 10
- 230000008901 benefit Effects 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 238000007605 air drying Methods 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 7
- CTQMJYWDVABFRZ-UHFFFAOYSA-N cloxiquine Chemical compound C1=CN=C2C(O)=CC=C(Cl)C2=C1 CTQMJYWDVABFRZ-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229920000767 polyaniline Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000010408 film Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- WDFKMLRRRCGAKS-UHFFFAOYSA-N chloroxine Chemical compound C1=CN=C2C(O)=C(Cl)C=C(Cl)C2=C1 WDFKMLRRRCGAKS-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZDASUJMDVPTNTF-UHFFFAOYSA-N 5,7-dibromo-8-quinolinol Chemical compound C1=CN=C2C(O)=C(Br)C=C(Br)C2=C1 ZDASUJMDVPTNTF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005485 electric heating Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- RJIWZDNTCBHXAL-UHFFFAOYSA-N nitroxoline Chemical compound C1=CN=C2C(O)=CC=C([N+]([O-])=O)C2=C1 RJIWZDNTCBHXAL-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 2
- WQXKGOOORHDGFP-UHFFFAOYSA-N 1,2,4,5-tetrafluoro-3,6-dimethoxybenzene Chemical compound COC1=C(F)C(F)=C(OC)C(F)=C1F WQXKGOOORHDGFP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PJICSCIQDNKYJR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)benzenethiol Chemical compound SC1=CC=CC=C1C1=NC2=CC=CC=C2S1 PJICSCIQDNKYJR-UHFFFAOYSA-N 0.000 description 1
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 description 1
- DKXHWIYYIFXGRB-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)benzenethiol Chemical compound SC1=CC=CC=C1C1=NC2=CC=CC=C2O1 DKXHWIYYIFXGRB-UHFFFAOYSA-N 0.000 description 1
- GHGZVWOTJDLREY-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2O1 GHGZVWOTJDLREY-UHFFFAOYSA-N 0.000 description 1
- QBKTXRLYEHZACW-UHFFFAOYSA-K 2-ethylhexanoate;neodymium(3+) Chemical compound [Nd+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QBKTXRLYEHZACW-UHFFFAOYSA-K 0.000 description 1
- YEDRPPAWPVYYIG-UHFFFAOYSA-N 3,5,7-trichloroquinolin-8-ol Chemical compound ClC1=CN=C2C(O)=C(Cl)C=C(Cl)C2=C1 YEDRPPAWPVYYIG-UHFFFAOYSA-N 0.000 description 1
- QHOMONLFHWLKIM-UHFFFAOYSA-N 3-decylquinolin-8-ol Chemical compound OC1=CC=CC2=CC(CCCCCCCCCC)=CN=C21 QHOMONLFHWLKIM-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- OYUKRQOCPFZNHR-UHFFFAOYSA-N 4-methylquinolin-8-ol Chemical compound C1=CC=C2C(C)=CC=NC2=C1O OYUKRQOCPFZNHR-UHFFFAOYSA-N 0.000 description 1
- KDZOCMHDOCFKRK-UHFFFAOYSA-N 5-(n-phenylanilino)quinolin-8-ol Chemical compound C12=CC=CN=C2C(O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 KDZOCMHDOCFKRK-UHFFFAOYSA-N 0.000 description 1
- GYNOCDRNIVTYOG-UHFFFAOYSA-N 5-(nonoxymethyl)quinolin-8-ol Chemical compound C1=CC=C2C(COCCCCCCCCC)=CC=C(O)C2=N1 GYNOCDRNIVTYOG-UHFFFAOYSA-N 0.000 description 1
- DGIQZKXQEUGFPA-UHFFFAOYSA-N 5-chloro-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C=CC=C2Cl DGIQZKXQEUGFPA-UHFFFAOYSA-N 0.000 description 1
- 229940105058 5-methyl-8-hydroxyquinoline Drugs 0.000 description 1
- DQDASZMPEDEYMO-UHFFFAOYSA-N 6-methyl-7,8,9,10-tetrahydrophenanthridin-4-ol Chemical compound C1CCCC2=C1C1=CC=CC(O)=C1N=C2C DQDASZMPEDEYMO-UHFFFAOYSA-N 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229940009827 aluminum acetate Drugs 0.000 description 1
- QXKWMSWOMAKXFY-UHFFFAOYSA-K aluminum octadecanoate toluene Chemical compound [Al+3].CC1=CC=CC=C1.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O QXKWMSWOMAKXFY-UHFFFAOYSA-K 0.000 description 1
- JJCSYJVFIRBCRI-UHFFFAOYSA-K aluminum;hexadecanoate Chemical compound [Al].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O JJCSYJVFIRBCRI-UHFFFAOYSA-K 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- PAANDJQFKIOOFM-UHFFFAOYSA-N benzo[f]quinolin-5-ol Chemical compound C1=CN=C2C(O)=CC3=CC=CC=C3C2=C1 PAANDJQFKIOOFM-UHFFFAOYSA-N 0.000 description 1
- ZCLVNIZJEKLGFA-UHFFFAOYSA-H bis(4,5-dioxo-1,3,2-dioxalumolan-2-yl) oxalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O ZCLVNIZJEKLGFA-UHFFFAOYSA-H 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- VBXWCGWXDOBUQZ-UHFFFAOYSA-K diacetyloxyindiganyl acetate Chemical compound [In+3].CC([O-])=O.CC([O-])=O.CC([O-])=O VBXWCGWXDOBUQZ-UHFFFAOYSA-K 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- XXCLAJNAENJKLS-UHFFFAOYSA-N phenanthridin-4-ol Chemical compound N1=CC2=CC=CC=C2C2=C1C(O)=CC=C2 XXCLAJNAENJKLS-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- MHTSJSRDFXZFHQ-UHFFFAOYSA-N quinoline-8-thiol Chemical compound C1=CN=C2C(S)=CC=CC2=C1 MHTSJSRDFXZFHQ-UHFFFAOYSA-N 0.000 description 1
- ZUQDDQFXSNXEOD-UHFFFAOYSA-N quinoxalin-5-ol Chemical compound C1=CN=C2C(O)=CC=CC2=N1 ZUQDDQFXSNXEOD-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- RPVGLMKJGQMQSN-UHFFFAOYSA-N tiliquinol Chemical compound C1=CC=C2C(C)=CC=C(O)C2=N1 RPVGLMKJGQMQSN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/30—Metal salts; Chelates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/413,415 US6362339B1 (en) | 1999-10-06 | 1999-10-06 | Method of making metal 8-quinolinolato complexes |
| US413415 | 1999-10-06 | ||
| PCT/US1999/031173 WO2001025211A1 (en) | 1999-10-06 | 1999-12-29 | Method of making metal 8-quinolinolato complexes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69906593D1 DE69906593D1 (de) | 2003-05-08 |
| DE69906593T2 true DE69906593T2 (de) | 2004-03-11 |
Family
ID=23637140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69906593T Expired - Fee Related DE69906593T2 (de) | 1999-10-06 | 1999-12-29 | Verfahren zur herstellung von 8-chinolinolato metallkomplexen |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6362339B1 (https=) |
| EP (1) | EP1218345B1 (https=) |
| JP (1) | JP2003511372A (https=) |
| AU (1) | AU2716200A (https=) |
| DE (1) | DE69906593T2 (https=) |
| WO (1) | WO2001025211A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1326072A1 (en) * | 2000-09-12 | 2003-07-09 | Shino-Test Corporation | Chelate reagent for measuring aluminum and measuring method |
| JP3889564B2 (ja) * | 2000-10-31 | 2007-03-07 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子 |
| US6558735B2 (en) * | 2001-04-20 | 2003-05-06 | Eastman Kodak Company | Reusable mass-sensor in manufacture of organic light-emitting devices |
| AU2002950217A0 (en) * | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
| US6969952B2 (en) * | 2003-08-01 | 2005-11-29 | Hewlett-Packard Development Company, L.P. | System and method for automatically routing power for an integrated circuit |
| DE10351556A1 (de) * | 2003-11-03 | 2005-06-02 | Covion Organic Semiconductors Gmbh | Halogenierte Koordinationsverbindungen, deren Darstellung und Verwendung |
| KR20080109547A (ko) * | 2007-06-13 | 2008-12-17 | 삼성모바일디스플레이주식회사 | 유기 금속 착물, 이의 제조방법 및 이를 이용한 유기 발광소자 |
| CN101857568B (zh) * | 2010-06-03 | 2012-01-11 | 安徽大学 | 一种八面体形貌的8-羟基喹啉锌的制备方法 |
| KR20120002365A (ko) * | 2010-06-30 | 2012-01-05 | 코오롱인더스트리 주식회사 | 흡습제 및 이를 포함하는 광학소자용 보호막 |
| US8801972B2 (en) | 2011-02-14 | 2014-08-12 | Indian Institute Of Technology Kanpur | Zinc chalcogenides, doped zinc chalcogenides, and methods of making |
| WO2012110857A1 (en) * | 2011-02-14 | 2012-08-23 | Indian Institute Of Technology Kanpur | Zinc chalcogenides, doped zinc chalcogenides, and methods of making |
| CN104151238B (zh) * | 2014-07-30 | 2016-01-20 | 南昌航空大学 | 一种直接制备纯8-羟基喹啉铝的方法 |
| WO2019073480A1 (en) | 2017-10-13 | 2019-04-18 | Sree Chitra Tirunal Institute For Medical Sciences And Technology | IMPLANTABLE INTER-AURICULAR COMMUNICATION OCCLUSION DEVICE HAVING A CENTRAL SECTION WIRE ON A LEFT HAND BRIDGE |
| CN110922356B (zh) * | 2019-12-03 | 2022-05-20 | 宁波南大光电材料有限公司 | 一种电子级高纯8-羟基喹啉铝的制备方法 |
| CN114621753A (zh) * | 2022-03-03 | 2022-06-14 | 青岛大学 | 一种利用铝络合物制备的青色荧光材料及方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300498A (en) | 1962-05-08 | 1967-01-24 | Gershon Herman | 8-hydroxyquinoline metal chelates |
| JPH0788444B2 (ja) | 1986-11-19 | 1995-09-27 | 三菱電線工業株式会社 | 難燃性樹脂組成物 |
| US4720432A (en) | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
| US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
| US5141671A (en) | 1991-08-01 | 1992-08-25 | Eastman Kodak Company | Mixed ligand 8-quinolinolato aluminum chelate luminophors |
| JPH05279371A (ja) | 1992-04-02 | 1993-10-26 | Denki Kagaku Kogyo Kk | ８−オキシキノリンアルミニウム錯体の製造法 |
| JPH07196620A (ja) | 1994-01-10 | 1995-08-01 | Nippon Steel Chem Co Ltd | ８−オキシキノリン−アルミニウム塩の製造方法 |
-
1999
- 1999-10-06 US US09/413,415 patent/US6362339B1/en not_active Expired - Fee Related
- 1999-12-29 DE DE69906593T patent/DE69906593T2/de not_active Expired - Fee Related
- 1999-12-29 JP JP2001528157A patent/JP2003511372A/ja not_active Withdrawn
- 1999-12-29 AU AU27162/00A patent/AU2716200A/en not_active Abandoned
- 1999-12-29 EP EP99968974A patent/EP1218345B1/en not_active Expired - Lifetime
- 1999-12-29 WO PCT/US1999/031173 patent/WO2001025211A1/en not_active Ceased
-
2001
- 2001-10-31 US US09/996,871 patent/US20020040143A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE69906593D1 (de) | 2003-05-08 |
| WO2001025211A1 (en) | 2001-04-12 |
| JP2003511372A (ja) | 2003-03-25 |
| US6362339B1 (en) | 2002-03-26 |
| EP1218345B1 (en) | 2003-04-02 |
| US20020040143A1 (en) | 2002-04-04 |
| EP1218345A1 (en) | 2002-07-03 |
| AU2716200A (en) | 2001-05-10 |
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