WO2003000661A1 - Compose de coordination metallique et dispositif electroluminescent - Google Patents
Compose de coordination metallique et dispositif electroluminescent Download PDFInfo
- Publication number
- WO2003000661A1 WO2003000661A1 PCT/JP2002/006001 JP0206001W WO03000661A1 WO 2003000661 A1 WO2003000661 A1 WO 2003000661A1 JP 0206001 W JP0206001 W JP 0206001W WO 03000661 A1 WO03000661 A1 WO 03000661A1
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- WIPO (PCT)
- Prior art keywords
- group
- general formula
- atom
- alkyl group
- coordination compound
- Prior art date
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 47
- 239000002184 metal Substances 0.000 title claims abstract description 47
- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- 238000005401 electroluminescence Methods 0.000 title abstract 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000004429 atom Chemical group 0.000 claims abstract description 10
- 239000003446 ligand Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 34
- 229910052741 iridium Inorganic materials 0.000 abstract description 7
- 238000004020 luminiscence type Methods 0.000 abstract description 7
- 239000010409 thin film Substances 0.000 abstract description 4
- 229910052703 rhodium Inorganic materials 0.000 abstract description 3
- 229910052697 platinum Inorganic materials 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 235000019557 luminance Nutrition 0.000 description 6
- 238000006862 quantum yield reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 230000005684 electric field Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000005424 photoluminescence Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical group 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 206010039740 Screaming Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 230000009878 intermolecular interaction Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YFDVQUUMKXZPLK-ZHACJKMWSA-N (ne)-n-(3,4-dihydro-2h-naphthalen-1-ylidene)hydroxylamine Chemical compound C1=CC=C2C(=N/O)/CCCC2=C1 YFDVQUUMKXZPLK-ZHACJKMWSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 1
- ROLKDXFFBNOIDS-UHFFFAOYSA-N 5,6-dihydroquinoline Chemical compound C1=CN=C2C=CCCC2=C1 ROLKDXFFBNOIDS-UHFFFAOYSA-N 0.000 description 1
- KWHUHTFXMNQHAA-UHFFFAOYSA-N 6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CCCCC2=CC=CC=C12 KWHUHTFXMNQHAA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 101100214488 Solanum lycopersicum TFT2 gene Proteins 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- -1 aluminum quinolinol Chemical compound 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- KZEYRHDSWHSHIR-UHFFFAOYSA-N iridium;2-phenylpyrimidine Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC=N1 KZEYRHDSWHSHIR-UHFFFAOYSA-N 0.000 description 1
- 229930192419 itoside Natural products 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000005750 substituted cyclic group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
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- 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
- 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
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
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- H—ELECTRICITY
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- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1007—Non-condensed systems
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/181—Metal complexes of the alkali metals and alkaline earth metals
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Definitions
- the present invention relates to an electroluminescent device using an organic compound.
- an organic electro-optical device using a metal coordination compound as a light emitting material More specifically, an organic electro-optical device using a metal coordination compound as a light emitting material
- FIGS. 1 (a) and (b) The basic configuration is shown in FIGS. 1 (a) and (b) [see, for example, Macromol. Symp. 125, 1-48 (19997)].
- an organic EL device is generally composed of a plurality of organic film layers on a transparent substrate 15 between a transparent electrode 14 and a metal electrode 11.
- the organic layer is composed of the light emitting layer 12 and the hole transport layer 13.
- the transparent electrode 14 ITO or the like having a large work function is used, and good hole injection characteristics from the transparent electrode 14 to the hole transport layer 13 are provided.
- the metal electrode 11 a metal material having a small work function, such as aluminum, magnesium or an alloy using them, is used so as to have good electron injection into the organic layer.
- a film thickness of 50 to 200 n'm is used.
- an aluminum quinolinol complex having an electron transporting property and a light emitting property (a typical example is Alq 3 shown below) is used.
- the hole transport layer 13 is made of a material having an electron donating property, such as a biphenyldiamine derivative (a typical example is H_NPD shown below).
- the element having the above configuration exhibits rectifying properties, and when an electric field is applied such that the metal electrode 11 is a cathode and the transparent electrode 4 is an anode, electrons are injected from the metal electrode 11 into the light emitting layer 12 and the transparent electrode Holes are injected from 15.
- the injected holes and electrons recombine in the light emitting layer 12 to generate excitons and emit light.
- the hole transport layer 13 functions as an electron blocking layer, and the recombination efficiency at the interface between the light emitting layer 12 and the hole transport layer 13 increases, and the luminous efficiency increases.
- an electron transport layer 16 is provided between the metal electrode 11 and the light emitting layer 12 in FIG. 1A. Efficient light emission can be achieved by separating light emission from electron and hole transport to form a more effective carrier blocking configuration.
- an electron transport material such as an oxaziazole derivative can be used.
- a fluorescent light-emitting device the fluorescence when a luminescent material molecule transitions from a singlet exciton to a ground state is emitted. Taken out.
- a phosphorescent device uses light emission via triplet excitons.
- Literature 1 Improvdedenergyytranasfeerinelectrotophosphore sce nt de evice (D.F.
- a configuration having four organic layers is mainly used as shown in Fig. 1 (c). It consists of a hole transport layer 13, a light emitting layer 12, an exciton diffusion preventing layer 17 and an electron transport layer 16 from the anode side.
- the materials used are a carrier transporting material and a phosphorescent material shown below. Abbreviations of each material are as follows.
- PtOEP Platinum-octaethylporphyrin complex
- the organic EL element using the phosphorescent light emission there is a problem that the light emission deteriorates particularly in an energized state.
- the reason for this is not clear, but is presumed as follows.
- the lifetime of a triplet exciton is more than three orders of magnitude longer than the lifetime of a singlet exciton. Formation, changes in molecular microstructure, It is considered that the structural change of the surrounding material may occur.
- phosphorescent light-emitting devices are expected to have high luminous efficiency, but have a problem of deterioration of electrical conduction. Therefore, compounds with high efficiency luminescence and high stability are desired for luminescent materials used in phosphorescent light-emitting devices. ing.
- the present invention aims to provide a stable light-emitting element that maintains high luminance for a long period of time with high efficiency light emission, and provides a specific metal coordination compound as a novel light-emitting material for that purpose. is there.
- the metal coordination compound according to the present invention is represented by the following general formula (1).
- M is a metal atom of Ir., Pt, Rh or Pd, and L and L 'represent different bidentate ligands.
- m is 1, 2 or 3, and n is 0, 1 or 2.
- m + n is 2 or 3.
- the partial structure ML m is represented by the following general formula (2), and the partial structure ML 'n is represented by the following general formula
- N and C are a nitrogen atom and a carbon atom, respectively, A, A 'and A “are each a cyclic group which may have a substituent bonded to a metal atom M via a nitrogen atom, and B, B 'And B “are each an optionally substituted cyclic group bonded to a metal atom M via a carbon atom.
- the substituent is a halogen atom, a cyano group, a nitro group, a trialkylsilyl group (each of the alkyl groups is independently a linear or branched alkyl group having 1 to 8 carbon atoms), carbon A linear or branched alkyl group having 1 to 20 atoms (one or two or more non-adjacent methylene groups in the alkyl group are one O—, one S—, one CO—, one CO — O—, -OC
- 0_, _CH CH—, one C ⁇ C— may be substituted, and a hydrogen atom in the alkyl group may be substituted by a fluorine atom.
- X and X ′ each represent a linear or branched alkylene group having 2 to 10 carbon atoms (in the alkylene group, two or more non-adjacent methylene groups are _ ⁇ , 1 S—, One CO_, one CO—O—, one O—CO_, one CH2CH—, _C ⁇ C— may be substituted, and a hydrogen atom in the alkylene group may be substituted with a fluorine atom. )
- E and G each have a linear or branched alkyl group having 1 to 20 carbon atoms (a hydrogen atom in the alkyl group may be substituted by a fluorine atom) or a substituent.
- n is 0 in the general formula (1), and the partial structure ML, n in the general formula (1) is represented by the general formula (3);
- the partial structure ML'n is preferably represented by the general formula (4), and in the general formula (1), the partial structure ML'n is preferably represented by the general formula (5).
- X is a linear or branched alkylene group having 2 to 6 carbon atoms (one or two or more non-adjacent methylene groups in the alkylene group is one or more).
- 0—, _S—, —CO—, one CO—O—, _0—CO—, one CH CH—, one C ⁇ C—, and the hydrogen atom in the alkylene group is fluorine May be substituted with an atom.).
- the metal coordination compound M is I r in the general formula (1) is good preferable.
- the present invention is the electroluminescent device in which the layer containing the metal coordination compound is sandwiched between two opposing electrodes, and emits light when a voltage is applied between the electrodes.
- an electroluminescent element that emits phosphorescence by applying an electric field is preferable.
- FIG. 1 is a conceptual diagram showing an example of the light emitting device of the present invention.
- FIG. 2 is a diagram schematically illustrating an example of a configuration of a panel including an organic EL element and a driving unit.
- FIG. 3 is a diagram illustrating an example of a pixel circuit using a TFT (thin film transistor).
- the quantum yield of the light-emitting material itself is large in order to increase the luminous efficiency of the organic EL device. It is important to efficiently transfer energy between hosts or between hosts and guests. Although the cause of light emission deterioration due to energization is not clear at present, it is considered that it is at least related to the change in the light emitting material environment due to the light emitting material itself or its surrounding molecules.
- n is preferably 0 or 1, and more preferably 0.
- the partial structure ML'n is represented by the general formula (3).
- C is preferable, and M is preferably Ir or Rh, more preferably Ir. preferable.
- the metal coordination compound used in the present invention emits phosphorescent light.
- the lowest excited state is a triplet state MLCT * (Metal-to-Ligandchargetransfer) excited state force ⁇ - ⁇ excited state it is conceivable that. Phosphorescence is generated when transitioning from these states to the ground state.
- MLCT * Metal-to-Ligandchargetransfer
- the determination of phosphorescence was made based on whether or not oxygen was lost.
- a compound was dissolved in a chromatographic form, and the oxygen-substituted solution and the nitrogen-substituted solution were irradiated with light.Comparing the photoluminescence, the oxygen-substituted solution showed almost no emission from the compound. The solution after nitrogen substitution can be distinguished because photoluminescence can be confirmed.
- all the compounds of the present invention have been confirmed to be phosphorescent by this method unless otherwise specified.
- Sem (st) Emission spectrum area intensity when excited at the same wavelength
- Sem (sample) The intensity of the emission spectrum when excited at the same wavelength.
- the phosphorescence quantum yield referred to here is Ir (ppy) 3 as the standard sample, and the quantum yield It is given as a relative quantum yield with the ratio being unity.
- This is irradiated with a nitrogen laser beam with an excitation wavelength of 337 nm at room temperature using a luminescence lifetime measurement device manufactured by Hamamatsu Photonics, and the decay time of the luminescence intensity after the excitation pulse ends is measured.
- the emission intensity I after t seconds is defined by the following equation using the emission lifetime.
- the phosphorescence yield of the metal coordination compound of the present invention is as high as 0.1 to 0.8, and the phosphorescence lifetime is as short as 1 to 40 ⁇ sec.
- the metal coordination compound of the present invention is a material suitable for a luminescent material of an organic EL device because it has a high phosphorescence emission yield and a short phosphorescence life.
- the alkylene group represented by X in the general formula (2) which is a feature of the present invention, allows the cyclic groups A and B in the molecule (in addition, the partial structure ML ′ n
- the alkylene group represented by X ′ suppresses the rotational vibration in the dihedral direction between the cyclic group A ′ and ⁇ ′) in the molecule, It is considered that the metal coordination compound of the present invention reduced the path of energy deactivation in the molecule when emitting light, and achieved highly efficient light emission.
- a ring in the molecule can be obtained. It is possible to adjust the emission wavelength by changing the dihedral angle between the state groups A and B and A ′ and B ′, and in particular, to shorten the wavelength.
- the metal coordination compound of the present invention is suitable as a light emitting material for an organic EL device.
- the metal coordination compound of the present invention exhibited excellent performance in stability in an electric current endurance test. Due to the change in the state of intermolecular interaction due to the introduction of the alkylene group, which is a feature of the present invention, intermolecular interaction with a host material or the like can be controlled, which causes heat deactivation. It is considered that the formation of excited aggregates was suppressed, and thereby the device characteristics were improved.
- B to M which are used for X and X in Table 1 to Table 14, are Has the following structure
- CHCH- C One CH 2 CHCH 2 -D: — CH 2 CHCHCH 2 ——
- PQn2 used in the ring structures A "and B" in Tables 11 and 11 has the following structures.
- L and L ′ in Tables 11 to 1 to 14 and aromatic ring groups existing as substituents of the ring structures A ′′ and B ′′, and Ph 2 to P used in E and G h3 has the structure shown below.
- X-factory ZE IE-level -no X-ray Xn X-level X-type X X X X X-level
- X, X, Xn X, X. IE, IT, X, X, X, X, X, X
- the reaction product was cooled to room temperature, poured into 300 ml of 1N hydrochloric acid, and the precipitate was collected by filtration, washed with water, dissolved in acetone, and the insoluble material was removed by filtration.
- the acetone was evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography using chloroform as eluent to obtain iridium (III) tris.
- the Lmax (maximum emission wavelength) of the PL (photoluminescence) spectrum of a solution of this compound was 511 nm, and the quantum yield was 0.51.
- the PL spectrum of a solution of Ir (ppy) 3, which is the above-mentioned conventional luminescent material not crosslinked with an alkylene group was measured in the same manner.
- Lmax (maximum emission wavelength) was 510 nm, and the quantum yield was 0.40.
- the organic EL element obtained in shown to Example 3 after the addition c showed emission with high brightness by an electric field, the EL spectrum; L ma X (maximum emission wavelength) was filed at 5 1 0 nm.
- the organic layer was dried over anhydrous magnesium sulfate, dried under reduced pressure, and purified by silica gel column chromatography using a mixed solvent of hexane Z and ethyl acetate 5/1 as eluent to obtain 19 g of a light brown liquid.
- This liquid was purified with a Kugelro still, and a pale green 3,2,1-trimethylene-12-phenylviridine 13.5 R (yield 6.8%),
- glycerol 50 ml was placed in a 100 ml four-necked flask, and the mixture was heated and stirred at 130 to 140 ° C. for 2 hours while nitrogen was bubbled. Glycerol was allowed to cool to 100 ° C, and 3,2,1-trimethylene-12-phenylpyridine 0.98 g (5.0 2 mmole), iridium (III) acetylacetonate 0.50 g (1 0.2 mm o 1 e), and the mixture was heated and stirred at 190 to 210 ° C for 8 hours under a nitrogen stream.
- the reaction product was cooled to room temperature, poured into 300 ml of 1N hydrochloric acid, and the precipitate was collected by filtration, washed with water, dissolved in acetone, and the insoluble material was removed by filtration. The acetone was evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography using chloroform as eluent. g (yield 22.7%) was obtained.
- the organic EL device obtained in Example 6 described later emitted blue-green light due to the electric field.
- FIG. 1 (b) As the device configuration, a device having three organic layers as shown in FIG. 1 (b) was used. A 100 nm thick ITO (transparent electrode 14) was formed on a glass substrate (transparent substrate 15) and then patterned. The following organic layer on the ITO electrode And an electrode layer 1 0- 4 P a vacuum chamber within one, by vacuum deposition by resistance heating, and successively formed by the following film thickness.
- Organic layer 1 (hole transport layer 13) (40 nm): o; —NPD
- Organic layer 2 (Emitting layer 1 2) (30 nm): CB PZ luminescent material (295/5) CBP was used as the host material, and the metal coordination compound shown in Table 2 below was used as the luminescent material. Ratio 5 weight. / 0 was formed by co-evaporation.
- Organic layer 3 (Electron transport layer 16) (30 nm): A 1 q 3
- Metal electrode layer 1 (1 5 nm): A 1 L i alloys (L i content: 1.8 by weight 0/0)
- Metal electrode layer 2 (100 nm): A 1
- the measurement was performed in a dry nitrogen flow after removing from the vacuum chamber to remove the cause of deterioration due to oxygen and water.
- Comparative Example 1 a conventional light-emitting material is described in the aforementioned Reference 2.
- Table 2 shows the results of the current endurance test of the devices using each compound. The half-life of luminance was clearly longer than that of the device using the conventional light-emitting material, and a device having high durability derived from the stability of the material of the present invention was obtained. Table 2
- FIG. 2 schematically illustrates an example of a configuration of a panel including an organic EL element and a driving unit.
- the number of pixels was set to 128 ⁇ 128 pixels.
- One pixel was composed of three color pixels, a green pixel, a blue pixel and a red pixel.
- TFT circuit A thin film transistor circuit (called TFT circuit) using polysilicon was formed on a glass substrate by a well-known method.
- an organic layer and a metal electrode layer were vacuum-deposited to the following film thickness and patterned.
- the configuration of the organic layer corresponding to each color pixel is as follows.
- the light emitting layer for the green pixel was formed by co-evaporating a phosphorescent material No. 1 in a weight ratio of 7% using CBP as a host.
- a scanning signal driver, an information signal driver 1, and a current supply source are arranged and connected to a gate selection line, an information signal line, and a current supply line, respectively.
- the pixel circuit (equivalent circuit) shown in Fig. 3 is arranged at the intersection of the gate selection line and the information signal line.
- the scanning signal driver sequentially selects the gate selection lines G1, G2, G3... Gn, and in synchronization with this, the image signal is applied from the information signal driver.
- TFT 1 when a selection signal is applied to the gate selection line, TFT 1 is turned on, a display signal is supplied from the information signal line to the capacitor C add, and the good potential of the TFT 2 is determined.
- a current is supplied from a current supply line to an organic light-emitting element portion (abbreviated as EL) arranged in each pixel according to the gate potential of the TFT 2. Since the gate potential of TFT2 is held at Cadd during one frame period, the current from the current supply line continues to flow through the EL element during this period. This makes it possible to maintain light emission during one frame period.
- EL organic light-emitting element portion
- a method of driving using an active matrix type TFT circuit was used as an application to a display, but the present invention is not particularly limited to a switching element, and a single crystal silicon substrate or a MIM (Metal-insulator-metal) element, a-Si (amorphous silicon) type T
- a light-emitting element using the metal coordination compound of the present invention represented by the general formula (1) as a light-emitting material has high luminous efficiency and can maintain high-luminance luminescence for a long period of time. It became. In addition, it is an excellent material that can adjust the emission wavelength, especially shorten the wavelength. Further, the light emitting element of the present invention is excellent also as a display element.
- the high-efficiency light-emitting device indicated by the present invention can be applied to products that require energy saving and high brightness. Examples of applications include display devices, lighting devices, light sources for printers, and backlights for liquid crystal display devices.
- As a display device energy saving, high visibility and lightweight flat panel display can be realized.
- As a light source of a printer a laser light source unit of a laser beam printer which is currently widely used can be replaced with the light emitting element of the present invention.
- An image is formed by arranging elements that can be independently addressed on an array and performing desired exposure on a photosensitive drum. By using the element of the present invention, the volume of the device can be significantly reduced.
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Description
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EP02738730A EP1400514B1 (en) | 2001-06-25 | 2002-06-17 | Metal coordination compound and electroluminescence device |
DE60231117T DE60231117D1 (de) | 2001-06-25 | 2002-06-17 | Metallkoordinationsverbindung und elektrolumineszenzvorrichtung |
KR1020037016545A KR100747060B1 (ko) | 2001-06-25 | 2002-06-17 | 금속배위화합물 및 전계발광소자 |
US10/181,342 US6824894B2 (en) | 2001-06-25 | 2002-06-17 | Metal coordination compound and electroluminescence device |
US10/942,861 US7078115B2 (en) | 2001-06-25 | 2004-09-17 | Metal coordination compound and electroluminescence device |
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US10/942,861 Division US7078115B2 (en) | 2001-06-25 | 2004-09-17 | Metal coordination compound and electroluminescence device |
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Also Published As
Publication number | Publication date |
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EP1400514A1 (en) | 2004-03-24 |
KR100747060B1 (ko) | 2007-08-07 |
US6824894B2 (en) | 2004-11-30 |
EP1400514B1 (en) | 2009-02-11 |
US7078115B2 (en) | 2006-07-18 |
CN1503785A (zh) | 2004-06-09 |
KR20040010735A (ko) | 2004-01-31 |
ATE422493T1 (de) | 2009-02-15 |
US20050085654A1 (en) | 2005-04-21 |
CN100500656C (zh) | 2009-06-17 |
DE60231117D1 (de) | 2009-03-26 |
EP1400514A4 (en) | 2005-04-13 |
US20030235712A1 (en) | 2003-12-25 |
JP2003007469A (ja) | 2003-01-10 |
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