JP4083243B2 - 有機金属錯体 - Google Patents
有機金属錯体 Download PDFInfo
- Publication number
- JP4083243B2 JP4083243B2 JP50183199A JP50183199A JP4083243B2 JP 4083243 B2 JP4083243 B2 JP 4083243B2 JP 50183199 A JP50183199 A JP 50183199A JP 50183199 A JP50183199 A JP 50183199A JP 4083243 B2 JP4083243 B2 JP 4083243B2
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- Prior art keywords
- complex
- group
- optionally substituted
- aryl
- otf
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- Expired - Lifetime
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- 125000002524 organometallic group Chemical group 0.000 title claims description 12
- 239000003446 ligand Substances 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 150000002602 lanthanoids Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 229910052771 Terbium Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 7
- 229910052693 Europium Inorganic materials 0.000 claims description 6
- 229910052684 Cerium Inorganic materials 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910052691 Erbium Inorganic materials 0.000 claims description 4
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 4
- 229910052779 Neodymium Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 229910052772 Samarium Inorganic materials 0.000 claims description 3
- 229910052775 Thulium Inorganic materials 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- ZEJHEROGFWIRLO-UHFFFAOYSA-N nitrosulfonylformonitrile Chemical compound [O-][N+](=O)S(=O)(=O)C#N ZEJHEROGFWIRLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 37
- 239000007787 solid Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 31
- 239000000460 chlorine Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 238000000605 extraction Methods 0.000 description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 230000005855 radiation Effects 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical group [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000005424 photoluminescence Methods 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 235000004338 Syringa vulgaris Nutrition 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 206010070834 Sensitisation Diseases 0.000 description 3
- 241001104043 Syringa Species 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- -1 lanthanide metals Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 230000005672 electromagnetic field Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000012857 radioactive material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- IAHHHZBPQZNCFG-UHFFFAOYSA-N 1-tert-butyl-4-(4-phenylphenyl)benzene Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 IAHHHZBPQZNCFG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001785 cerium compounds Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002471 indium Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910021644 lanthanide ion Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- TXBBUSUXYMIVOS-UHFFFAOYSA-N thenoyltrifluoroacetone Chemical compound FC(F)(F)C(=O)CC(=O)C1=CC=CS1 TXBBUSUXYMIVOS-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- FRNOGLGSGLTDKL-UHFFFAOYSA-N thulium atom Chemical compound [Tm] FRNOGLGSGLTDKL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ZRAOLHHYMQLCAW-UHFFFAOYSA-N tris(1h-pyrazol-5-yl) borate Chemical class C1=CNN=C1OB(OC1=NNC=C1)OC=1C=CNN=1 ZRAOLHHYMQLCAW-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- High Energy & Nuclear Physics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9711237.9 | 1997-06-02 | ||
| GBGB9711237.9A GB9711237D0 (en) | 1997-06-02 | 1997-06-02 | Organomettallic Complexes |
| PCT/GB1998/001587 WO1998055561A1 (en) | 1997-06-02 | 1998-06-01 | Organometallic complexes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002513440A JP2002513440A (ja) | 2002-05-08 |
| JP2002513440A5 JP2002513440A5 (enExample) | 2005-12-22 |
| JP4083243B2 true JP4083243B2 (ja) | 2008-04-30 |
Family
ID=10813346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50183199A Expired - Lifetime JP4083243B2 (ja) | 1997-06-02 | 1998-06-01 | 有機金属錯体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7601859B2 (enExample) |
| EP (1) | EP0988353B1 (enExample) |
| JP (1) | JP4083243B2 (enExample) |
| AU (1) | AU7668198A (enExample) |
| DE (1) | DE69809739D1 (enExample) |
| GB (1) | GB9711237D0 (enExample) |
| WO (1) | WO1998055561A1 (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9712483D0 (en) | 1997-06-17 | 1997-08-20 | Kathirgamanathan Poopathy | Fabrication of light emitting devices from chelates of transition metals, lanthanides and actinides |
| JP3907142B2 (ja) * | 1998-08-18 | 2007-04-18 | 富士フイルム株式会社 | 有機エレクトロルミネツセンス素子材料およびそれを使用した有機エレクトロルミネツセンス素子 |
| GB9820805D0 (en) | 1998-09-25 | 1998-11-18 | Isis Innovation | Divalent lanthanide metal complexes |
| GB9823761D0 (en) * | 1998-11-02 | 1998-12-23 | South Bank Univ Entpr Ltd | Novel electroluminescent materials |
| GB9826407D0 (en) | 1998-12-02 | 1999-01-27 | South Bank Univ Entpr Ltd | Novel electroluminescent materials |
| GB9826405D0 (en) | 1998-12-02 | 1999-01-27 | South Bank Univ Entpr Ltd | Method for forming films or layers |
| GB9901971D0 (en) | 1999-02-01 | 1999-03-17 | South Bank Univ Entpr Ltd | Electroluminescent material |
| US6872471B2 (en) * | 2000-03-06 | 2005-03-29 | The Ohio State University Research Foundation | Infrared emitting electroluminescent and photoluminescent devices |
| WO2002074015A2 (en) * | 2001-03-14 | 2002-09-19 | The Trustees Of Princeton University | Materials and devices for blue phosphorescence based organic light emitting diodes |
| GB0109755D0 (en) | 2001-04-20 | 2001-06-13 | Elam T Ltd | Devices incorporating mixed metal organic complexes |
| TWI303533B (en) | 2001-06-15 | 2008-11-21 | Oled T Ltd | Electroluminescent devices |
| GB0116644D0 (en) | 2001-07-09 | 2001-08-29 | Elam T Ltd | Electroluminescent materials and devices |
| US7303824B2 (en) | 2001-08-04 | 2007-12-04 | Oled-T Limited | Electroluminescent device |
| US6699597B2 (en) | 2001-08-16 | 2004-03-02 | 3M Innovative Properties Company | Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein |
| GB0120828D0 (en) * | 2001-08-28 | 2001-10-17 | Isis Innovation | Method of driving an electroluminescent device |
| US6603150B2 (en) | 2001-09-28 | 2003-08-05 | Eastman Kodak Company | Organic light-emitting diode having an interface layer between the hole-transporting layer and the light-emitting layer |
| US6610455B1 (en) | 2002-01-30 | 2003-08-26 | Eastman Kodak Company | Making electroluminscent display devices |
| US6872472B2 (en) | 2002-02-15 | 2005-03-29 | Eastman Kodak Company | Providing an organic electroluminescent device having stacked electroluminescent units |
| AU2003221969A1 (en) | 2002-04-19 | 2003-11-03 | 3M Innovative Properties Company | Materials for organic electronic devices |
| US7241512B2 (en) | 2002-04-19 | 2007-07-10 | 3M Innovative Properties Company | Electroluminescent materials and methods of manufacture and use |
| US20040004433A1 (en) | 2002-06-26 | 2004-01-08 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
| US6939660B2 (en) | 2002-08-02 | 2005-09-06 | Eastman Kodak Company | Laser thermal transfer donor including a separate dopant layer |
| US6890627B2 (en) | 2002-08-02 | 2005-05-10 | Eastman Kodak Company | Laser thermal transfer from a donor element containing a hole-transporting layer |
| US6747618B2 (en) | 2002-08-20 | 2004-06-08 | Eastman Kodak Company | Color organic light emitting diode display with improved lifetime |
| US7811675B2 (en) * | 2002-11-06 | 2010-10-12 | The University Of Hong Kong | Electroluminescent metallo-supramolecules with terpyridine-based groups |
| US7230594B2 (en) | 2002-12-16 | 2007-06-12 | Eastman Kodak Company | Color OLED display with improved power efficiency |
| US6975067B2 (en) | 2002-12-19 | 2005-12-13 | 3M Innovative Properties Company | Organic electroluminescent device and encapsulation method |
| US7811676B2 (en) | 2002-12-24 | 2010-10-12 | Merck Patent Gmbh | Electroluminescent materials and devices |
| US7271406B2 (en) | 2003-04-15 | 2007-09-18 | 3M Innovative Properties Company | Electron transport agents for organic electronic devices |
| US7192657B2 (en) | 2003-04-15 | 2007-03-20 | 3M Innovative Properties Company | Ethynyl containing electron transport dyes and compositions |
| DE602004011257T2 (de) | 2003-11-18 | 2009-01-08 | 3M Innovative Properties Co., St. Paul | Elektrolumineszenzbauelemente und verfahren zur herstellung von elektrolumineszenzbauelementen mit einem farbwandlungselement |
| US7221332B2 (en) | 2003-12-19 | 2007-05-22 | Eastman Kodak Company | 3D stereo OLED display |
| GB0411572D0 (en) * | 2004-05-24 | 2004-06-23 | Cambridge Display Tech Ltd | Light-emitting device |
| US7316756B2 (en) | 2004-07-27 | 2008-01-08 | Eastman Kodak Company | Desiccant for top-emitting OLED |
| US9040170B2 (en) | 2004-09-20 | 2015-05-26 | Global Oled Technology Llc | Electroluminescent device with quinazoline complex emitter |
| US7501152B2 (en) | 2004-09-21 | 2009-03-10 | Eastman Kodak Company | Delivering particulate material to a vaporization zone |
| US7315042B2 (en) | 2004-11-18 | 2008-01-01 | 3M Innovative Properties Company | Semiconductors containing trans-1,2-bis(acenyl)ethylene compounds |
| US8569948B2 (en) | 2004-12-28 | 2013-10-29 | Samsung Display Co., Ltd. | Electroluminescent devices and methods of making electroluminescent devices including an optical spacer |
| US7645478B2 (en) | 2005-03-31 | 2010-01-12 | 3M Innovative Properties Company | Methods of making displays |
| US7615501B2 (en) | 2005-08-11 | 2009-11-10 | 3M Innovative Properties Company | Method for making a thin film layer |
| US9666826B2 (en) | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
| JP5209504B2 (ja) | 2006-02-08 | 2013-06-12 | スリーエム イノベイティブ プロパティズ カンパニー | ガラス転移点を超える温度でのフィルム基材の製造のための方法 |
| EP2355198B1 (en) | 2006-05-08 | 2015-09-09 | Global OLED Technology LLC | OLED electron-injecting layer |
| US7667391B2 (en) | 2006-08-04 | 2010-02-23 | Eastman Kodak Company | Electrically excited organic light-emitting diodes with spatial and spectral coherence |
| DE102006048202A1 (de) * | 2006-10-11 | 2008-04-17 | Universität Regensburg | Lanthanoid-Emitter für OLED-Anwendungen |
| US7911133B2 (en) | 2007-05-10 | 2011-03-22 | Global Oled Technology Llc | Electroluminescent device having improved light output |
| US7812531B2 (en) | 2007-07-25 | 2010-10-12 | Global Oled Technology Llc | Preventing stress transfer in OLED display components |
| US8076009B2 (en) | 2007-10-26 | 2011-12-13 | Global Oled Technology, Llc. | OLED device with fluoranthene electron transport materials |
| US8016631B2 (en) | 2007-11-16 | 2011-09-13 | Global Oled Technology Llc | Desiccant sealing arrangement for OLED devices |
| US8900722B2 (en) | 2007-11-29 | 2014-12-02 | Global Oled Technology Llc | OLED device employing alkali metal cluster compounds |
| US8877350B2 (en) | 2007-12-11 | 2014-11-04 | Global Oled Technology Llc | White OLED with two blue light-emitting layers |
| US7947974B2 (en) | 2008-03-25 | 2011-05-24 | Global Oled Technology Llc | OLED device with hole-transport and electron-transport materials |
| US8283054B2 (en) | 2009-04-03 | 2012-10-09 | Global Oled Technology Llc | Tandem white OLED with efficient electron transfer |
| DE112010004188T5 (de) * | 2009-10-28 | 2012-11-22 | Sumitomo Chemical Co., Ltd. | Metallkomplex mit mehrzähnigem Liganden |
| WO2013000531A1 (de) * | 2011-06-28 | 2013-01-03 | Merck Patent Gmbh | Metallkomplexe |
| KR102051360B1 (ko) * | 2011-11-30 | 2019-12-03 | 노발레드 게엠베하 | 유기 전자 소자 |
| KR20150058189A (ko) | 2012-09-21 | 2015-05-28 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 장치 및 조명 장치 |
| US10593886B2 (en) | 2013-08-25 | 2020-03-17 | Molecular Glasses, Inc. | OLED devices with improved lifetime using non-crystallizable molecular glass mixture hosts |
| KR101746297B1 (ko) * | 2014-11-06 | 2017-06-21 | 포항공과대학교 산학협력단 | 유기 리간드가 치환된 페로브스카이트 나노결정입자 발광체 제조방법, 이에 의해 제조된 나노결정입자 발광체 및 이를 이용한 발광소자 |
| WO2016072807A1 (ko) | 2014-11-06 | 2016-05-12 | 포항공과대학교 산학협력단 | 유기 리간드가 치환된 페로브스카이트 나노결정입자 발광체 제조방법, 이에 의해 제조된 나노결정입자 발광체 및 이를 이용한 발광소자 |
| JP7082984B2 (ja) | 2017-02-20 | 2022-06-09 | ノヴァレッド ゲーエムベーハー | 電子半導体デバイスおよびその電子半導体デバイスの製造方法および化合物 |
| CN114057779B (zh) * | 2020-07-29 | 2023-06-06 | 北京大学 | 混配型Ce(III)配合物及其作为电致发光材料的应用 |
| CN116082376A (zh) * | 2021-11-01 | 2023-05-09 | 北京大学 | d-f跃迁稀土配合物的非掺杂器件 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5237069A (en) * | 1990-10-26 | 1993-08-17 | The Dow Chemical Company | Hydridotris(pyrazolyl)borate metal complexes and polymerization process |
| US5571897A (en) * | 1991-12-05 | 1996-11-05 | Wallac Oy | Luminescent lanthanide chelates |
| US5707745A (en) * | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
| US6358631B1 (en) * | 1994-12-13 | 2002-03-19 | The Trustees Of Princeton University | Mixed vapor deposited films for electroluminescent devices |
| US5627164A (en) * | 1995-06-13 | 1997-05-06 | Exxon Research And Engineering Company | Pyrazolyl borates complexes-(LAW294) |
-
1997
- 1997-06-02 GB GBGB9711237.9A patent/GB9711237D0/en active Pending
-
1998
- 1998-06-01 WO PCT/GB1998/001587 patent/WO1998055561A1/en not_active Ceased
- 1998-06-01 AU AU76681/98A patent/AU7668198A/en not_active Abandoned
- 1998-06-01 DE DE69809739T patent/DE69809739D1/de not_active Expired - Lifetime
- 1998-06-01 JP JP50183199A patent/JP4083243B2/ja not_active Expired - Lifetime
- 1998-06-01 EP EP98924488A patent/EP0988353B1/en not_active Expired - Lifetime
-
2004
- 2004-05-18 US US10/848,183 patent/US7601859B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7601859B2 (en) | 2009-10-13 |
| EP0988353A1 (en) | 2000-03-29 |
| EP0988353B1 (en) | 2002-11-27 |
| WO1998055561A1 (en) | 1998-12-10 |
| GB9711237D0 (en) | 1997-07-23 |
| AU7668198A (en) | 1998-12-21 |
| JP2002513440A (ja) | 2002-05-08 |
| DE69809739D1 (de) | 2003-01-09 |
| US20040215000A1 (en) | 2004-10-28 |
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