CN1503785A - 金属配位化合物及电致发光装置 - Google Patents
金属配位化合物及电致发光装置 Download PDFInfo
- Publication number
- CN1503785A CN1503785A CNA028087011A CN02808701A CN1503785A CN 1503785 A CN1503785 A CN 1503785A CN A028087011 A CNA028087011 A CN A028087011A CN 02808701 A CN02808701 A CN 02808701A CN 1503785 A CN1503785 A CN 1503785A
- Authority
- CN
- China
- Prior art keywords
- group
- alkyl group
- formula
- atom
- carbon atoms
- 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.)
- Granted
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 25
- 239000002184 metal Substances 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 title claims abstract description 23
- 238000005401 electroluminescence Methods 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
- 125000004429 atom Chemical group 0.000 claims abstract description 8
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 7
- 239000003446 ligand Substances 0.000 claims abstract description 5
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 4
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 3
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- -1 metal complex compound Chemical class 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 9
- 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
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 34
- 238000004020 luminiscence type Methods 0.000 abstract description 8
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000005284 excitation Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000006862 quantum yield reaction Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 238000005424 photoluminescence Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 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 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 101100214488 Solanum lycopersicum TFT2 gene Proteins 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910021417 amorphous silicon Inorganic materials 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 239000003256 environmental substance Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000009878 intermolecular interaction Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 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
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical class [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
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-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
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- KYLIZBIRMBGUOP-UHFFFAOYSA-N Anetholtrithion Chemical group C1=CC(OC)=CC=C1C1=CC(=S)SS1 KYLIZBIRMBGUOP-UHFFFAOYSA-N 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 101100489584 Solanum lycopersicum TFT1 gene Proteins 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XIQUJVRFXPBMHS-UHFFFAOYSA-N hydron;o-prop-2-enylhydroxylamine;chloride Chemical compound Cl.NOCC=C XIQUJVRFXPBMHS-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- KZEYRHDSWHSHIR-UHFFFAOYSA-N iridium;2-phenylpyrimidine Chemical class [Ir].C1=CC=CC=C1C1=NC=CC=N1 KZEYRHDSWHSHIR-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- QRDGOCRZAXXYPV-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1.C1=CON=N1 QRDGOCRZAXXYPV-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 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 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Images
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
-
- 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
- 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
-
- 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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- C09K2211/1007—Non-condensed systems
-
- 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
-
- 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
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
-
- 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
-
- 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
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/181—Metal complexes of the alkali metals and alkaline earth metals
-
- 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
-
- 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]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- 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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
提供一种有通式MLmL’n(1)所示基本结构的金属配位化合物(其中M为Ir、Pt、Rh或Pd的金属原子;L和L’为相互不同的二齿配体;m为1、2或3;n为0、1或2,条件是m+n为2或3),该基本结构中至少一个二齿配体L有通过有2-10个碳原子的亚烷基缩合形成的部分结构。在由一或多个设置在阴极和阳极之间的有机薄膜构成的电致发光装置中,至少一层是通过有式(1)所示结构的金属配位化合物组成的发光分子作为客体材料混合在主体材料中形成的发光层。用此发光层可提供产生高效发光并长时间稳定地保持高发光度的电致发光装置。
Description
技术领域
本发明涉及利用有机化合物的电致发光装置,更特别地涉及用金属配位化合物作发光材料的有机电致发光装置(下文中称为“有机EL装置”)。
背景技术
有机EL装置作为高速响应性和高效发光装置的应用研究一直在积极进行。其基本结构示于图1(a)和(b)中(例如Macromol Symp.125,1-48(1977))。
如图1中所示,有机EL装置一般有这样的结构,包括在透明基板15之上的透明电极14、金属电极11、和置于其间的多个有机薄膜层。
图1(a)的装置中,所述有机层包括发光层12和空穴迁移层13。所述透明电极14使用有大功函的ITO等以提供从透明电极14至空穴迁移层13的良好的空穴注入特性。所述金属电极11使用小功函的金属如铝、镁或这些金属的合金以提供良好的电子注入特性。这些电极的厚度为50-200nm。
所述发光层12使用有电子迁移特性和发光特性的铝-羟基喹啉配合物(其典型实例是下文所示Alq3)等。所述空穴迁移层使用有给电子特性的联苯二胺衍生物(其典型实例是下文所示α-NPD)等。
上述结构的装置有整流特性,在作为阴极的金属电极11和作为阳极的透明电极14之间施加电场时,由金属电极11向发光层12注入电子并由透明电极15注入空穴。注入的空穴和电子在发光层12内重组形成激发子而产生激发光。此时,空穴迁移层13起电子阻挡层的作用以提高发光层12和空穴迁移层13间界面处的重组效率,从而提高发光效率。
而在图1(b)的结构中,电子迁移层16置于金属电极11和发光层12之间。使发光与电子和空穴迁移分离提供更有效的载流子阻挡结构,可实现有效发光。所述电子迁移层16使用电子迁移材料如含氧二唑(oxidiazole)衍生物。
迄今已知的有机EL装置中所用发光方法包括荧光和磷光。在荧光发光装置中,从单重激子状态跃迁至基态时产生荧光。另一方面,在磷光发光装置中,利用从三重激子状态至基态的跃迁。
近年来,一直在研究发光率比利用荧光的装置更高的利用磷光的装置。
代表性的公开文献可包括:
论文1:电致磷光装置中改进的能量转移(D.F.O’Brien,etal.,Applied Physics Letters,Vol.74,No.3,p.422(1999));和
论文2:基于电致磷光的极高效的绿色有机发光装置(M.A.Baldo,et al.,Applied Physics Letters,Vol.75,No.1,p.4(1999))。
这些论文中,主要使用包括图1(c)所示4有机层装置的结构,包括(从阳极侧)空穴迁移层13、发光层12、防止激发子扩散层17和电子迁移层16。其中所用材料包括载流子迁移材料和磷光材料,下面示出其中的缩写。
Alq3:铝-羟基喹啉配合物
α-NPD:N4,N4’-二-萘-1-基-N4,N4’-二苯基-联苯-4,4’-二胺
CBP:4,4’-N,N’-二咔唑-联苯
BCP:2,9-二甲基-4,7-二苯基-1,10-菲咯啉
PtOEP:铂-八乙基卟啉配合物
Ir(ppy)3:铱-苯基嘧啶配合物
上述利用磷光的有机EL装置伴有发光衰退的问题,尤其是在供能状态下。发光衰退的原因尚不清楚,但此现象的原因可归因于三重激子的寿命比单重激子的寿命长至少三位数,从而使分子长时间处于高能状态导致与环境物质反应、生成激态复合物或激态分子、瞬间分子结构改变、环境物质结构改变等。
总之,如上所述,预计磷光发光装置提供较高的发光效率,但该EL装置伴有在供能状态下发光衰退的问题。想要产生高效发光且有高稳定性的化合物作为磷光装置中所用发光材料。
发明内容
因此,本发明的目的是提供能产生高效发光并长时间保持高发光度(亮度)的稳定发光装置。作为新的发光材料,本发明提供一种特殊的金属配位化合物。
本发明所述金属配位化合物用下式(1)表示:
MLmL’n (1)
其中M为Ir、Pt、Rh或Pd的金属原子;L和L’为相互不同的二齿配体;m为1、2或3;n为0、1或2,条件是m+n为2或3;部分结构MLm用以下所示式(2)表示,部分结构ML’n用以下所示式(3)、(4)或(5)表示:
其中N和C分别为氮和碳原子;A和A’分别为能有取代基并通过所述氮原子与金属原子M键合的环状基团;B、B’和B”分别为能有取代基并通过所述碳原子与金属原子M相连的环状基团;
{其中所述取代基选自卤原子、氰基、硝基、三烷基甲硅烷基(其中所述烷基独立地为有1至8个碳原子的直链或支链烷基)、有1至20个碳原子的直链或支链烷基(其中所述烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述烷基可包括可用氟原子代替的氢原子)、或能有取代基的芳族环状基团(其中所述取代基为卤原子、氰基、硝基、或有1至20个碳原子的直链或支链烷基(其中所述烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述烷基可包括可用氟原子代替的氢原子)};
A和B、A’和B’、及A”和B”分别通过共价键彼此键合;A和B、及A’和B’分别通过X和X’彼此键合;
X和X’独立地为有2至10个碳原子的直链或支链亚烷基(其中所述亚烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述亚烷基可包括可用氟原子代替的氢原子);
E和G独立地为有1至20个碳原子的直链或支链烷基(其中所述烷基可包括任选地用氟原子代替的氢原子)、或能有取代基的芳族环状基团(其中所述取代基为卤原子、氰基、硝基、三烷基甲硅烷基(其中所述烷基独立地为有1至8个碳原子的直链或支链烷基)、或有1至20个碳原子的直链或支链烷基(其中所述烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述烷基可包括可用氟原子代替的氢原子))。
本发明所述金属配位化合物可优选为其中式(1)中n为0;式(1)中部分结构ML’n为式(3)表示;式(1)中部分结构ML’n为式(4)表示;或式(1)中部分结构ML’n为式(5)表示的那些。
此外,式(1)中,X可优选为有2至6个碳原子的直链或支链亚烷基(其中所述亚烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述亚烷基可包括可用氟原子代替的氢原子)。
此外,所述金属配位化合物可优选包含Ir作为如上所述式(1)中的M。
此外,本发明还提供一种电致发光装置,其中包含上述金属配位化合物的层夹在两个相对设置的电极之间,在所述电极之间施加电压产生激发光。
特别地,所述电致发光装置可优选为产生磷光的电致发光装置。
附图简述
图1说明本发明发光装置的实施方案,其中(a)为有两个有机层的装置结构,(b)为有三个有机层的装置结构,(c)为有四个有机层的装置结构。
图2示意地说明包括有机EL装置和驱动装置的面板结构的例子。
图3说明使用TFTs(薄膜晶体管)的像素电路的例子。
实施本发明的最佳方式
在发光层由载流子迁移主体材料和磷光客体材料形成的情况下,为改善所得有机EL装置的发光效率,要求中心发光材料本身提供较高的发光量子产量。此外,主体材料分子之间或主体材料分子与客体材料分子之间的有效能量转移也是重要因素。
此外,发光衰退的原因尚不清楚,但可推测至少与发光材料本身或因其周围分子结构所致环境变化有关。
为此,本发明人进行了许多研究,发现了上述式(1)所示金属配位化合物,而且发现使用所述发光材料的有机EL装置能高效发光、长时间保持高亮度(发光度)、而且在供能状态的(发光)衰退较小。
式(1)的金属配位化合物中,n可优选为0或1,更优选为0。此外,所述部分结构ML’n可优选为上述式(3)表示。
此外,式(1)中,X可优选为有2至10个碳原子的直链或支链亚烷基(其中所述亚烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述亚烷基可包括可用氟原子代替的氢原子)。此外,式中M可优选为Ir或Rh,更优选为Ir。
本发明所用金属配位化合物发射磷光,据信,其最低激发态为三重态中的MLCT*(金属至配体电荷转移)激发态或π-π*激发态,在从此态跃迁至基态时产生磷光。
<物理性能的测量方法>
下面描述本发明中物理性能的测量方法。
(1)磷光和荧光之间的判断方法
根据是否被氧气减活化来鉴别磷光。使(试样)化合物溶于氯仿,充以氧气或氮气之后,经光照比较光致发光。充以氧气的溶液几乎未观察到归因于所述化合物的发光,相反充以氮气的溶液有光致发光,从而可进行区别。除非另有说明,所有本发明化合物的磷光都通过此方法证明。
(2)本发明所用磷光产量可按下式确定:
Ф(试样)/Ф(st)=[Sem(试样)/Iabs(试样)]/[Sem(st)/Iabs(st)]
其中Iabs(st)代表在标准试样的激发波长下的吸收系数;Sem(st)代表在相同波长下激发时发光光谱的面积强度;Iabs(试样)代表在目标化合物的激发波长下的吸收系数;和Sem(试样)代表在相同波长下激发时发光光谱面积强度。
本文所述磷光产量值是相对于作为标准试样的Ir(ppy)3的磷光产量Ф=1的相对值。
(3)磷光寿命的测量方法。
使(试样)化合物溶于氯仿,以约0.1μm的厚度旋涂于石英基板之上,在室温下用发光寿命测定仪(Hamamatsu Photonics K.K.制造)使之暴露于337nm激发波长的脉动氮激光。所述激发脉冲结束后,测定发光强度的衰变时间。
用I0代表初始发光强度时,t(sec)后的发光强度相对于发光寿命τ(sec)按下式表示:
I=I0·exp(-t/τ)。
本发明金属配位化合物表现出0.11至0.8的高磷光量子产量和1至40微秒的短磷光寿命。如果磷光寿命长,则待发光的处于三重激发态的分子数量增加,从而造成发光效率降低的问题,尤其是电流密度高时。因此,为提高发光效率,缩短上述磷光寿命是有效的。本发明金属配位化合物有高磷光量子产量和相对短的磷光寿命,因而适合用作有机EL装置的发光材料。
此外,如后面描述的实施例1中所示,通过式(2)的用X表示的亚烷基(是本发明的特征)抑制分子间环状基团A和B之间(在所述部分结构ML’n为式(3)表示的情况下通过X’表示的亚烷基抑制分子内环状基团A’和B’之间)在两面角方向的旋转振动。为此,本发明金属配位化合物使发光时分子内的能量减活途径减少,从而实现高效发光。
此外,通过适当选择上述亚烷基的长度,改变分子内环状基团A和B及A’和B’之间的两面角以控制发射波长,特别是可向较短波长移动。
从上述观点出发,本发明金属配位化合物也适用作本发明发光材料。
此外,如后面的实施例中所述,在连续供能试验中已阐明本发明金属配位化合物还在稳定性方面显示出极佳性能。通过引入上述亚烷基(是本发明的特征)使分子间相互作用状态发生改变,可用所述主体材料等控制分子间相互作用,从而抑制形成导致热钝化的激发缔合物。结果,使装置特性得到改善。
<铱配位化合物的合成>
以铱配位化合物为例说明本发明式(1)所示金属配位化合物的合成方案。
铱配位化合物的合成
或
下表1-1至表1-14中示出本发明所用金属配位化合物的具体结构式。但这些只是代表性实例,本发明不限于这些例子。
表1-1至1-14中所示L和L’所用L1至L11’有如下所示结构。
此外,表1-1至1-14中X和X’所用B至M’有如下所示结构。
表1-1至1-11中环状结构A”和B”所用Pi至Qn2有如下所示结构。
此外,表1-1至1-14中L和L’所用Ph2至Ph3;用于环状结构A”和B”的以取代基形式存在的芳族基团;及E和G有如下所示结构。
表1-1
表1-2
表1-3
表1-4
表1-5
表1-6
表1-7
表1-8
表1-9
表1-10
No | M | m | n | L | X | R1 | R2 | X1 | X2 | X3 | X4 | R7 | R8 | R9 | R10 |
L′ | A″ | B″ | R3 | R4 | R5 | R6 | A″ | ||||||||
R7 | R8 | R9 | R10 | ||||||||||||
B″ | |||||||||||||||
R7 | R8 | R9 | R10 | ||||||||||||
376 | Ir | 2 | 1 | L1 | B | H | H | H | H | H | H | - | - | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
377 | Ir | 2 | 1 | L1 | B | H | H | F | CF3 | H | H | - | - | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
378 | Ir | 2 | 1 | L1 | B | H | H | Cl | CF3 | H | H | - | - | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
379 | Ir | 2 | 1 | L1 | B | H | H | H | OCF3 | H | H | - | - | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
380 | Ir | 2 | 1 | L1 | B | H | H | OC4H9 | H | H | H | - | - | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
381 | Ir | 2 | 1 | L1 | B | H | H | Ph2 | H | H | H | H | H | CF3 | H |
- | Ph1 | Pi | Ph2 | H | H | H | H | F | H | H | |||||
- | - | - | - | ||||||||||||
382 | Ir | 2 | 1 | L1 | B | H | H | Tn7 | H | H | H | H | H | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
383 | Ir | 2 | 1 | L1 | B | H | CH3 | Ph2 | H | H | H | H | F | H | H |
- | Tn2 | Pi | H | CH3 | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
384 | Ir | 2 | 1 | L1 | B | H | CH3 | Np3 | H | H | H | H | H | - | - |
- | Tn3 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
385 | Ir | 2 | 1 | L1 | C | H | - | H | H | H | H | - | - | - | - |
- | Tn4 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
386 | Ir | 2 | 1 | L1 | D | H | H | CF3 | H | H | H | - | - | - | - |
- | Np2 | Pi | H | H | H | CF3 | - | - | - | - | |||||
- | - | - | - | ||||||||||||
387 | Ir | 2 | 1 | L1 | E | - | - | H | Cl | H | H | - | - | - | - |
- | Pe1 | Py1 | H | - | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
388 | Ir | 2 | 1 | L1 | F | H | - | H | OCH(CH3)2 | H | H | - | - | - | - |
- | Tn1 | Pr | H | H | Ph3 | H | - | - | - | - | |||||
- | - | - | - |
表1-11
No | M | m | n | L | X | R1 | R2 | X1 | X2 | X3 | X4 | R7 | R8 | R9 | R10 |
L′ | A″ | B″ | R3 | R4 | R5 | R6 | A″ | ||||||||
R7 | R8 | R9 | R10 | ||||||||||||
B″ | |||||||||||||||
R7 | R8 | R9 | R10 | ||||||||||||
389 | Ir | 2 | 1 | L1 | H | H | - | Ph2 | H | H | H | H | H | CF3 | H |
- | Ph1 | Pi | H | H | H | Tn5 | - | - | - | - | |||||
H | H | - | - | ||||||||||||
390 | Ir | 2 | 1 | L1 | H | CH3 | - | H | Tn5 | H | H | H | H | - | - |
- | Ph1 | Pi | H | H | H | Tn8 | - | - | - | - | |||||
H | H | - | - | ||||||||||||
391 | Rh | 2 | 1 | L1 | I | H | H | Tn8 | H | H | H | H | H | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
392 | Rh | 2 | 1 | L1 | P | - | H | OCH3 | H | H | H | - | - | - | - |
- | Ph1 | Pi | H | Ph2 | H | H | F | F | F | F | |||||
- | - | - | - | ||||||||||||
393 | Rh | 2 | 1 | L1 | V | H | - | Ph2 | H | H | H | H | F | H | H |
- | Tn2 | Py2 | - | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
394 | Rh | 2 | 1 | L1 | D′ | H | - | Ph2 | H | H | H | H | F | H | H |
- | Tn3 | Pi | Np3 | H | CF3 | H | H | H | - | - | |||||
- | - | - | - | ||||||||||||
395 | Pt | 1 | 1 | L1 | F′ | - | - | F | CF3 | H | H | - | - | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
396 | Pt | 1 | 1 | L1 | J′ | - | - | Ph3 | H | H | CF3 | - | - | - | - |
- | Tn1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
397 | Pt | 1 | 1 | L1 | C | H | - | Pe2 | H | H | H | H | - | - | - |
- | Np2 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
398 | Pd | 1 | 1 | L1 | B | H | H | H | H | H | H | - | - | - | - |
- | Ph1 | Pi | H | H | H | H | - | - | - | - | |||||
- | - | - | - | ||||||||||||
399 | Pd | 1 | 1 | L1 | B | H | H | H | OCH(CH3)2 | H | H | - | - | - | - |
- | Tn3 | Pi | Ph2 | H | H | CH3 | H | C3F7 | H | H | |||||
- | - | - | - | ||||||||||||
400 | Pd | 1 | 1 | L1 | C | H | - | H | H | H | H | - | - | - | - |
- | Np1 | Pr | H | H | An | H | - | - | - | - | |||||
H | - | - | - |
表1-12
No | M | m | n | L | X | R1 | R2 | X1 | X2 | X3 | X4 | R7 | R8 | R9 | R10 |
E | E | ||||||||||||||
R7 | R8 | R9 | R10 | ||||||||||||
G | G | ||||||||||||||
R7 | R8 | R9 | R10 | ||||||||||||
401 | Ir | 2 | 1 | L1 | B | H | H | H | H | H | H | - | - | - | - |
CH3 | - | - | - | - | |||||||||||
CH3 | - | - | - | - | |||||||||||
402 | Ir | 2 | 1 | L1 | B | H | H | F | CF3 | H | H | - | - | - | - |
CH3 | - | - | - | - | |||||||||||
CH3 | - | - | - | - | |||||||||||
403 | Ir | 2 | 1 | L1 | B | H | H | Cl | CF3 | H | H | - | - | - | - |
CH3 | - | - | - | - | |||||||||||
CH3 | - | - | - | - | |||||||||||
404 | Ir | 2 | 1 | L1 | B | H | H | H | OCF3 | H | H | - | - | - | - |
CF3 | - | - | - | - | |||||||||||
CF3 | - | - | - | - | |||||||||||
405 | Ir | 2 | 1 | L1 | B | H | H | OC4H9 | H | H | H | - | - | - | - |
CF3 | - | - | - | - | |||||||||||
CF3 | - | - | - | - | |||||||||||
406 | Ir | 2 | 1 | L1 | B | H | H | Ph2 | H | H | H | H | H | CF3 | H |
Ph3 | - | - | - | - | |||||||||||
Ph3 | - | - | - | - | |||||||||||
407 | Ir | 2 | 1 | L1 | B | H | H | Tn7 | H | H | H | H | H | - | - |
Ph2 | H | C3H7 | H | H | |||||||||||
Ph2 | H | C3H7 | H | H | |||||||||||
408 | Ir | 2 | 1 | L1 | B | H | CH3 | Ph2 | H | H | H | H | F | H | H |
Tn5 | H | H | - | - | |||||||||||
Tn5 | H | H | - | - | |||||||||||
409 | Ir | 2 | 1 | L1 | B | H | CH3 | Np3 | H | H | H | H | H | - | - |
CH3 | - | - | - | - | |||||||||||
PH3 | - | - | - | - | |||||||||||
410 | Ir | 2 | 1 | L1 | C | H | - | H | H | H | H | - | - | - | - |
Tn6 | H | H | - | - | |||||||||||
Tn6 | H | H | - | - | |||||||||||
411 | Ir | 2 | 1 | L1 | D | H | H | CF3 | H | H | H | - | - | - | - |
Np3 | CH3O | H | - | - | |||||||||||
Np3 | CH3O | H | - | - | |||||||||||
412 | Ir | 2 | 1 | L1 | E | - | - | H | Cl | H | H | - | - | - | - |
Np4 | F | - | - | - | |||||||||||
Np4 | F | - | - | - | |||||||||||
413 | Ir | 2 | 1 | L1 | F | H | - | H | OCH(CH3)2 | H | H | - | - | - | - |
Tr7 | CH3 | H | - | - | |||||||||||
Tn7 | CH3 | H | - | - |
表1-13
No | M | m | n | L | X | R1 | R2 | X1 | X2 | X3 | X4 | R7 | R8 | R9 | R10 |
E | E | ||||||||||||||
R7 | R8 | R9 | R10 | ||||||||||||
G | G | ||||||||||||||
R7 | R8 | R9 | R10 | ||||||||||||
414 | Ir | 2 | 1 | L1 | H | H | - | Ph2 | H | H | H | H | H | CF3 | H |
Tn8 | H | H | - | - | |||||||||||
Tn8 | H | H | - | - | |||||||||||
415 | Ir | 2 | 1 | L1 | H | CH3 | - | H | Tn5 | H | H | H | H | - | - |
Pe2 | H | - | - | - | |||||||||||
Pe2 | H | - | - | - | |||||||||||
416 | Rh | 2 | 1 | L1 | I | H | H | Tn8 | H | H | H | H | H | - | - |
CH3 | - | - | - | - | |||||||||||
CH3 | - | - | - | - | |||||||||||
417 | Rh | 2 | 1 | L1 | P | - | H | OCH3 | H | H | H | - | - | - | - |
CH3 | - | - | - | - | |||||||||||
CH3 | - | - | - | - | |||||||||||
418 | Rh | 2 | 1 | L1 | V | H | - | Ph2 | H | H | H | H | F | H | H |
CH3 | - | - | - | - | |||||||||||
CH3 | - | - | - | - | |||||||||||
419 | Rh | 2 | 1 | L1 | D′ | H | - | Ph2 | H | H | H | H | F | H | H |
Ph3 | - | - | - | - | |||||||||||
Ph3 | - | - | - | - | |||||||||||
420 | Pt | 1 | 1 | L1 | F′ | - | - | F | CF3 | H | H | - | - | - | - |
CH3 | - | - | - | - | |||||||||||
CH3 | - | - | - | - | |||||||||||
421 | Pt | 1 | 1 | L1 | J′ | - | - | Ph3 | H | H | CF3 | - | - | - | - |
CF3 | - | - | - | - | |||||||||||
CF3 | - | - | - | - | |||||||||||
422 | Pt | 1 | 1 | L1 | C | H | - | Pe2 | H | H | H | H | - | - | - |
Pi2 | H | H | - | - | |||||||||||
Pi2 | H | H | - | - | |||||||||||
423 | Pd | 1 | 1 | L1 | B | H | H | H | H | H | H | - | - | - | - |
CH3 | - | - | - | - | |||||||||||
CH3 | - | - | - | - | |||||||||||
424 | Pd | 1 | 1 | L1 | B | H | H | H | OCH(CH3)2 | H | H | - | - | - | - |
CF3 | - | - | - | - | |||||||||||
CF3 | - | - | - | - | |||||||||||
425 | Pd | 1 | 1 | L1 | C | H | - | H | H | H | H | - | - | - | - |
Qn2 | H | H | - | - | |||||||||||
Qn2 | H | H | - | - |
表1-14
No | M | m | n | L | X | R1 | R2 | R3 | R4 | X1 | X2 | X3 | X4 |
426 | Ir | 3 | 0 | L2 | B | H | H | - | - | H | H | - | H |
427 | Ir | 3 | 0 | L3 | B | H | H | - | - | F | H | H | - |
428 | Ir | 3 | 0 | L4 | B | H | H | - | - | H | F | H | H |
429 | Ir | 3 | 0 | L5 | B | H | H | - | - | - | F | H | H |
430 | Ir | 3 | 0 | L6 | B | H | H | - | - | CF3 | - | - | H |
431 | Ir | 3 | 0 | L7 | B | H | H | - | - | H | H | H | H |
432 | Ir | 3 | 0 | L8 | B | H | H | - | - | F | CF3 | H | H |
433 | Ir | 3 | 0 | L9 | B | H | H | - | - | H | H | CF3 | F |
434 | Ir | 3 | 0 | L10 | B | H | H | - | - | H | H | H | H |
435 | Ir | 3 | 0 | L11 | B | H | H | - | - | H | H | H | H |
436 | Ir | 3 | 0 | L2′ | B | H | H | - | - | H | CH3 | - | H |
437 | Ir | 3 | 0 | L3′ | B | H | H | - | - | OCH3 | H | H | - |
438 | Ir | 3 | 0 | L4′ | B | H | H | - | - | H | H | H | H |
439 | Ir | 3 | 0 | L5′ | B | H | H | - | - | - | H | H | H |
440 | Ir | 3 | 0 | L6′ | B | H | H | - | - | H | - | - | H |
441 | Ir | 3 | 0 | L7′ | B | H | H | - | - | H | H | H | H |
442 | Ir | 3 | 0 | L8′ | B | H | H | - | - | H | H | H | H |
443 | Ir | 3 | 0 | L9′ | B | H | H | - | - | H | H | H | H |
444 | Ir | 3 | 0 | L10′ | B | H | H | - | - | H | H | H | H |
445 | Ir | 3 | 0 | L11′ | B | H | H | - | - | H | H | H | H |
446 | Ir | 3 | 0 | L1 | M′ | CH3 | CH3 | CH3 | CH3 | H | H | H | H |
447 | Ir | 3 | 0 | L1 | M′ | C2H5 | C2H5 | C2H5 | C2H5 | H | H | H | H |
448 | Ir | 3 | 0 | L1 | M′ | CH3 | CH3 | CH3 | CH3 | F | H | H | H |
449 | Ir | 3 | 0 | L1 | M′ | CH3 | CH3 | CH3 | CH3 | H | F | H | H |
450 | Ir | 3 | 0 | L1 | M′ | CH3 | CH3 | CH3 | CH3 | F | CH3 | H | H |
下面结合实施例解释本发明。
<实施例1>(实例化合物No.1的合成)
在2升三颈烧瓶中放入69.0g(472mM)α-四氢萘酮(α-tetralon)、50.0g(720mM)盐酸羟胺、500ml乙醇和360ml 2N-氢氧化钠水溶液,在室温下搅拌1小时。在减压下除去溶剂得到残余物(干固体)。向该残余物中加入500ml水,然后用乙酸乙酯萃取三遍,每次使用150ml乙酸乙酯。用无水硫酸镁使有机层干燥,然后在减压下除去溶剂,得到74g α-四氢萘酮=肟的浅黄色晶体(收率:97.2%)。
在1升三巯烧瓶中放入80ml四氢呋喃和23.8g(595mM)60%-含油的氢化钠,在室温下搅拌5分钟,然后在15分钟内滴加至74g(459mM)α-四氢萘酮=肟在500ml无水DMF(二甲基甲酰胺)溶液中。然后将所述混合物在室温下搅拌1小时,向其中加入113.5g(939mM)烯丙基溴,然后在室温下搅拌12小时。反应后,使反应产物减压干燥得到残余物。向该残余物中加入500ml水,然后用乙酸乙酯萃取三遍,每次使用200ml乙酸乙酯。用无水硫酸镁使有机层干燥,然后在减压下除去溶剂,得到棕色液体。使该液体减压蒸馏得到79.5g(收率:86.0%)α-四氢萘酮=肟=O-烯丙基=醚(沸点=75-80℃(6.7Pa))。
在1升高压釜中放入58.0g(288mM)α-四氢萘酮=肟=O-烯丙基=醚,充以氧气后,气密地密封,然后在190℃下剧烈搅拌5天。使该液体冷却至室温得到高粘性棕色液体,使之溶于氯仿,用5%盐酸萃取三遍(每次300ml)。用48%氢氧化钠使含水层碱化,用氯仿萃取三遍(每次350ml)。用无水硫酸镁使有机层干燥,然后在减压下蒸发。残余物通过硅胶柱色谱法(洗脱剂:氯仿)提纯,通过硅胶柱色谱法(洗脱剂:己烷/乙酸乙酯=5/1)进一步提纯,得到7.7g浅棕色液体。所述液体通过Kugelroh蒸馏器提纯得到6.6g无色的苯并-[h]-5,6-二氢喹啉(收率:12.6%)。
在100ml四巯烧瓶中放入50ml甘油,在搅拌并用氮气鼓泡下于130-140℃加热2小时。通过静置使所述甘油冷却至100℃,向其中加入0.91g(5.02mM)苯并-[h]-5,6-二氢喹啉和0.50g(1.02mM)乙酰丙酮合铱(III),然后在氮气流中于190-215℃加热搅拌5小时。使反应产物冷却至室温,倒入300ml 1N盐酸中。过滤回收沉淀物,水洗,溶于丙酮以通过过滤除去不溶物。在减压下除去丙酮得到残余物,通过硅胶柱色谱法(洗脱剂:氯仿)提纯,得到0.11g三{苯并-[h]-5,6-二氢喹啉}合铱(III)的黄色粉末(收率:14.7%)。
该化合物的溶液显示出*max(最大或峰发射波长)为511nm而量子产量为0.51的PL(光致发光)光谱。作为对照,测量与所述金属配位化合物不同的未用亚甲基交联的上述传统发光材料Ir(ppy)3的溶液的PL光谱时,该材料显示*max(最大发射波长)为510nm而量子产量为0.40。此外,通过施加电场,后面所述实施例3中得到的有机EL装置产生高发光度的激发光。而且其EL光谱*max(最大发射波长)为510nm。
<实施例2>(实例化合物No.53的合成)
在3升三巯烧瓶中放入166.0g(1036mM)1-苯并环庚酮、125.0g(1141mM)盐酸O-烯丙基羟胺、93.5g(1140mM)乙酸钠、158.0g(1143mM)碳酸钾和1500ml乙醇,于80℃加热搅拌1.5小时。使反应产物冷却至室温,在减压下除去溶剂得到残余物。向该残余物中加1500ml水,然后用乙酸乙酯萃取三遍(每次500ml)。用无水硫酸镁使有机层干燥,然后在减压下除去溶剂得到浅棕色液体。使该液体在减压下蒸馏得到221.8g(收率:99.0%)1-苯并环庚酮=肟=O-烯丙基=醚(沸点=75-83℃(4.0Pa))。
在5升高压釜中放入220.0g(1022mM)1-苯并环庚酮=肟=O-烯丙基=醚,充以氧气后,气密地密封,然后在190℃下剧烈搅拌3天。使该液体冷却至室温得到高粘性棕色液体,使之溶于2升氯仿,用5%盐酸萃取三遍(每次500ml)。用48%氢氧化钠使含水层碱化,用氯仿萃取三遍(每次500ml)。用无水硫酸镁使有机层干燥,然后通过硅胶柱色谱法(洗脱剂:己烷/乙酸乙酯=5/1)提纯,得到19g浅棕色液体。所述液体通过Kugelroh蒸馏器提纯得到13.5g 3,2’-亚丙基-2-苯基吡啶的浅绿色液体(收率:13.5%)。
在100ml四巯烧瓶中放入50ml甘油,在搅拌并用氮气鼓泡下于130-140℃加热2小时。通过静置使所述甘油冷却至100℃,向其中加入0.98g(5.02mM)3,2’-亚丙基-2-苯基吡啶和0.50g(1.02mM)乙酰丙酮合铱(III),然后在氮气流中于190-215℃加热搅拌8小时。使反应产物冷却至室温,倒入300ml 1N盐酸中。过滤回收沉淀物,水洗,溶于丙酮以通过过滤除去不溶物。在减压下除去丙酮得到残余物,通过硅胶柱色谱法(洗脱剂:氯仿)提纯,得到0.18g三{3,2 ’-亚丙基-2-苯基吡啶}合铱(III)的黄色粉末(收率:22.7%)。
通过施加电场,后面所述实施例6中得到的有机EL装置产生蓝绿色的激发光。
<实施例3-11和对比例1>
用有图1(b)所示三层结构有机层的装置作为装置结构。在玻璃基板(透明基板15)上形成100nm厚的ITO(氧化锡铟)薄膜(透明电极14),然后制作布线图。在真空室(10-4Pa)内用电阻加热通过真空(气相)沉积相继在所述形成ITO的基板上形成如下所示有机层和金属电极层。
有机层1(空穴迁移层13)(40nm):α-NPD
有机层2(发光层12)(20nm)∶CBP:发光材料(95∶5)的混合物
该层通过作为主体材料的CBP与重量比为5wt%的作为发光材料的下表2中所示金属配位化合物共沉积形成。
有机层3(电子迁移层16)(30nm):Alq3
金属电极层1(金属电极11)(15nm):Al-Li合金(Li=1.8wt%)
金属电极层2(金属电极11)(100nm):Al
形成电极材料层之后,进行布线以提供3mm2的电极面积。
向有ITO电极(作为阳极)和Al电极(作为阴极)的各发光装置施加电场(电压)以给每个装置提供相同的电流值,测量发光度(亮度)随时间的变化。电流量设定为70mA/cm2,初期各装置显示出在80-250cd/m2范围内的发光度。这些发光度值降至其1/2需要一段时间。
为测量,将各发光装置从真空室中取出,在干燥氮气流气氛中进行测量以消除装置衰退因素如氧气和湿气(水分)。
对比例1中,使用上述论文2中所述Ir(ppy)3作为传统发光材料。
使用各化合物的连续供能试验装置的结果示于表2中。与使用传统发光材料的装置相比,使用本发明金属配位化合物的发光装置提供较长的发光度半衰期,从而导致基于本发明材料的良好稳定性的具有高耐久性的装置。
表2
实施例号 实例化合物号 发光度半衰期(Hr)
3 (1) 950
4 (7) 850
5 (48) 700
6 (53) 900
7 (102) 600
8 (131) 500
9 (302) 800
10 (376) 750
11 (401) 650
对比例1 Ir(ppy)3 350
<实施例12>
结合图2,描述本发明电致发光装置用于采用图3所示TFT电路的活性基体型彩色有机EL显示器的实施方案。
图2示意地说明装配有机EL装置和驱动装置的面板结构的例子。该实施方案中,像素数量为128×128像素。顺便提及,一个像素由绿色像素、蓝色像素和红色像素组成的三色像素构成。
在玻璃基板上,按已知方式用多晶硅形成薄膜晶体管电路(称为“TFT电路”)。
在与所述每一彩色像素对应的区域,用硬掩模通过真空沉积形成以下所示厚度的有机层和金属电极层,然后制作布线图。以下示出与各像素对应的有机层的结构。
绿色像素:α-NPD(40nm)/CBP:磷光材料(=93∶7重量比)(30nm)/BCP(20nm)/Alq(40nm)
蓝色像素:α-NPD(50nm)/BCP(20nm)/Alq(50nm)
红色像素:α-NPD(40nm)/CBP:PtOEP(=93∶7重量比)(30nm)/BCP(20nm)/Alq(40nm)
所述绿色像素的发光层是通过作为主体材料的CBP与重量比为7%的磷光材料(实例化合物No.1)共沉积形成的。
图2所示面板中,配置扫描信号驱动器、数据信号驱动器和电流供应源,分别与门选择线(gate selection lines)、数据信号线和供电线相连。在门选择线和数据信号线的交叉点,设置图3中所示像素电路(等效电路)。扫描信号驱动器顺序选择门扫描线G1、G2、G3、…、Gn,与之同步地由数据信号驱动器提供图像信号。
下面结合图3中所示等效电路描述像素电路操作。当给门选择线施加选择信号时,打开TFT1使得由数据信号线向电容器Cadd供应显示信号,从而测定TFT2的门电位。根据TFT2的门电位通过供电线向在各像素配置的有机发光装置部分(缩写为EL)供应电流。在一个帧周期内使TFT2的门电位保持在Cadd,以致该周期内所述电流连续地从供电线流入EL装置部分。从而,在一个帧周期内保持发光。
结果证明可显示所要图像信息,而且发现稳定地显示良好的图像。
该实施方案中,尽管将采用TFT电路的活性基体型驱动方案用于所述显示器,但本发明所用开关装置不必特殊限制,甚至单晶硅基板、MIM(金属-绝缘体-金属)装置、a-Si(无定形硅)TFT电路等也可很容易地用于所述显示器。
工业实用性
如上所述,用本发明上述式(1)所示金属配位化合物作发光材料的发光装置可提供高发光效率并长时间保持高亮度的发光。此外,所述材料是能调节发射波长特别是提供较短波长的优异材料。本发明发光装置作为显示设备也极好。
本发明所示高效发光装置适用于要求节能和高亮度的产品。作为应用实例,可列举用于显示设备、照明设备、印刷机的光源和液晶显示设备的背光。作为显示设备,可提供能节能、分辨率高或重量减轻的平面显示器。此外,作为印刷机的光源,可用本发明发光装置代替目前广泛使用的激光束印刷机的激光源部分。通过以矩阵形式独立地排列可寻址装置和相对于感光鼓进行所要求的曝光形成图像。用本发明装置可显著地减小设备体积(尺寸)。
Claims (9)
1.一种金属配位化合物,用下式(1)表示:
MLmL’n (1)
其中M为Ir、Pt、Rh或Pd的金属原子;L和L’为相互不同的二齿配体;m为1、2或3;n为0、1或2,条件是m+n为2或3;部分结构MLm用以下所示式(2)表示,部分结构ML’n用以下所示式(3)、(4)或(5)表示:
其中N和C分别为氮和碳原子;A和A’分别为能有取代基并通过所述氮原子与金属原子M键合的环状基团;B、B’和B”分别为能有取代基并通过所述碳原子与金属原子M相连的环状基团;
{其中所述取代基选自卤原子、氰基、硝基、三烷基甲硅烷基(其中所述烷基独立地为有1至8个碳原子的直链或支链烷基)、有1至20个碳原子的直链或支链烷基(其中所述烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述烷基可包括可用氟原子代替的氢原子)、或能有取代基的芳族环状基团(其中所述取代基为卤原子、氰基、硝基、或有1至20个碳原子的直链或支链烷基(其中所述烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述烷基可包括可用氟原子代替的氢原子)};
A和B、A’和B’、及A”和B”分别通过共价键彼此键合;A和B、及A’和B’分别通过X和X’彼此键合;
X和X’独立地为有2至10个碳原子的直链或支链亚烷基(其中所述亚烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述亚烷基可包括可用氟原子代替的氢原子);
E和G独立地为有1至20个碳原子的直链或支链烷基(其中所述烷基可包括任选地用氟原子代替的氢原子)、或能有取代基的芳族环状基团(其中所述取代基为卤原子、氰基、硝基、三烷基甲硅烷基(其中所述烷基独立地为有1至8个碳原子的直链或支链烷基)、或有1至20个碳原子的直链或支链烷基(其中所述烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述烷基可包括可用氟原子代替的氢原子)}。
2.权利要求1的化合物,其中式(1)中n为0。
3.权利要求1的化合物,其中式(1)中部分结构ML’n为式(3)所示。
4.权利要求1的化合物,其中式(1)中部分结构ML’n为式(4)所示。
5.权利要求1的化合物,其中式(1)中部分结构ML’n为式(5)所示。
6.权利要求1的化合物,其中X为有2至10个碳原子的直链或支链亚烷基(其中所述亚烷基可包括一个或不相邻的两或多个可用-O-、-S-、-CO-、-CO-O-、-O-CO-、-CH=CH-或-C≡C-代替的亚甲基而且所述亚烷基可包括可用氟原子代替的氢原子)。
7.权利要求1的化合物,其中式(1)中的M为Ir。
8.一种电致发光装置,包括:基板、设置在所述基板之上的一对电极、和设置在所述电极对之间的至少一种权利要求1的式(1)所示金属配位化合物。
9.权利要求8的装置,其中在所述电极之间施加电压以产生磷光。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001190662A JP2003007469A (ja) | 2001-06-25 | 2001-06-25 | 発光素子及び表示装置 |
JP190662/2001 | 2001-06-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1503785A true CN1503785A (zh) | 2004-06-09 |
CN100500656C CN100500656C (zh) | 2009-06-17 |
Family
ID=19029400
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB028087011A Expired - Fee Related CN100500656C (zh) | 2001-06-25 | 2002-06-17 | 金属配位化合物及电致发光装置 |
Country Status (8)
Country | Link |
---|---|
US (2) | US6824894B2 (zh) |
EP (1) | EP1400514B1 (zh) |
JP (1) | JP2003007469A (zh) |
KR (1) | KR100747060B1 (zh) |
CN (1) | CN100500656C (zh) |
AT (1) | ATE422493T1 (zh) |
DE (1) | DE60231117D1 (zh) |
WO (1) | WO2003000661A1 (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100362006C (zh) * | 2005-09-16 | 2008-01-16 | 中国科学院长春应用化学研究所 | 树枝状铱配合物及使用该化合物的有机电致发光器件 |
CN102859743A (zh) * | 2010-04-28 | 2013-01-02 | 联邦科学和工业研究组织 | 基于磷光铱和相关第viii族金属多环化合物的电致发光装置 |
CN103650194A (zh) * | 2011-05-12 | 2014-03-19 | 剑桥显示技术有限公司 | 有机发光材料和器件 |
WO2018108109A1 (zh) * | 2016-12-13 | 2018-06-21 | 广州华睿光电材料有限公司 | 过渡金属配合物及其应用、混合物、有机电子器件 |
CN108467414A (zh) * | 2011-08-01 | 2018-08-31 | 通用显示公司 | 用于有机发光二极管的材料 |
Families Citing this family (79)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4438042B2 (ja) | 2001-03-08 | 2010-03-24 | キヤノン株式会社 | 金属配位化合物、電界発光素子及び表示装置 |
JP2003007469A (ja) * | 2001-06-25 | 2003-01-10 | Canon Inc | 発光素子及び表示装置 |
WO2003022908A1 (fr) * | 2001-09-04 | 2003-03-20 | Canon Kabushiki Kaisha | Composes de poids moleculaire eleve et dispositifs luminescents organiques |
JP3890242B2 (ja) * | 2002-03-26 | 2007-03-07 | キヤノン株式会社 | 高分子化合物及び電界発光素子 |
JP2003332074A (ja) * | 2002-05-09 | 2003-11-21 | Canon Inc | 金属配位化合物を用いた発光素子 |
TWI276369B (en) * | 2002-09-20 | 2007-03-11 | Idemitsu Kosan Co | Organic electroluminescent device |
EP1424381A3 (en) | 2002-11-26 | 2005-01-19 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, and display and illuminator |
US7198730B2 (en) | 2003-08-28 | 2007-04-03 | E. I. Du Pont De Nemours And Company | Phosphorescent material |
JP4455211B2 (ja) * | 2003-08-29 | 2010-04-21 | キヤノン株式会社 | 発光素子及び表示装置 |
DE10345572A1 (de) * | 2003-09-29 | 2005-05-19 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
US7279232B2 (en) * | 2004-01-26 | 2007-10-09 | Universal Display Corporation | Electroluminescent stability |
JP4378186B2 (ja) * | 2004-02-06 | 2009-12-02 | キヤノン株式会社 | 有機el素子アレイ |
US7709100B2 (en) * | 2004-07-07 | 2010-05-04 | Universal Display Corporation | Electroluminescent efficiency |
TW200614865A (en) * | 2004-08-23 | 2006-05-01 | Nippon Steel Chemical Co | Organic electroluminescent element |
JP4478555B2 (ja) * | 2004-11-30 | 2010-06-09 | キヤノン株式会社 | 金属錯体、発光素子及び画像表示装置 |
TW200634020A (en) | 2004-12-09 | 2006-10-01 | Merck Patent Gmbh | Metal complexes |
JP2008528646A (ja) * | 2005-02-03 | 2008-07-31 | メルク パテント ゲーエムベーハー | 金属錯体 |
US7498437B2 (en) * | 2005-04-27 | 2009-03-03 | Au Optronics Corporation | Phosphorescent light-emitting device with doped iridium-complex |
US7851072B2 (en) * | 2005-05-19 | 2010-12-14 | Universal Display Corporation | Stable and efficient electroluminescent materials |
WO2007004380A1 (ja) | 2005-07-01 | 2007-01-11 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
DE102005032332A1 (de) * | 2005-07-08 | 2007-01-11 | Merck Patent Gmbh | Metallkomplexe |
US20100177264A1 (en) * | 2005-08-15 | 2010-07-15 | Sumitomo Checmical Company, Limited | Light-emitting material containing metal complex and photoelectric device using same |
JP5076900B2 (ja) * | 2005-09-06 | 2012-11-21 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2007028417A1 (en) * | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
KR101358697B1 (ko) * | 2005-12-02 | 2014-02-07 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 반도체 장치, 디스플레이 장치, 및 전자 장치 |
JP2007173584A (ja) * | 2005-12-22 | 2007-07-05 | Canon Inc | 発光装置 |
DE102006006412A1 (de) * | 2006-02-13 | 2007-08-16 | Merck Patent Gmbh | Elektronisches Bauteil, Verfahren zu dessen Herstellung und dessen Verwendung |
EP1988143A4 (en) | 2006-02-20 | 2009-11-25 | Konica Minolta Holdings Inc | ORGANIC ELECTROLUMINESCENT ELEMENT, WHITE LIGHT EMITTING ELEMENT, DISPLAY DEVICE, AND LIGHTING DEVICE |
KR20080114749A (ko) * | 2006-02-22 | 2008-12-31 | 스미또모 가가꾸 가부시키가이샤 | 금속 착체, 고분자 화합물 및 이들을 포함하는 소자 |
EP1998387B1 (en) | 2006-03-17 | 2015-04-22 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
EP2615153B1 (en) | 2006-03-23 | 2017-03-01 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
JP2007269735A (ja) * | 2006-03-31 | 2007-10-18 | Canon Inc | 金属錯体、発光素子及び表示装置 |
US9118020B2 (en) | 2006-04-27 | 2015-08-25 | Global Oled Technology Llc | Electroluminescent devices including organic eil layer |
JP2007302565A (ja) * | 2006-05-08 | 2007-11-22 | Canon Inc | 金属錯体、発光素子及び画像表示装置 |
JP2008007500A (ja) * | 2006-06-02 | 2008-01-17 | Canon Inc | 金属錯体及び有機発光素子 |
JP2007335614A (ja) | 2006-06-15 | 2007-12-27 | Canon Inc | 有機電界発光素子及び表示装置 |
JP4965914B2 (ja) * | 2006-07-05 | 2012-07-04 | キヤノン株式会社 | 有機化合物及び発光素子 |
US7736756B2 (en) * | 2006-07-18 | 2010-06-15 | Global Oled Technology Llc | Light emitting device containing phosphorescent complex |
JP5127206B2 (ja) * | 2006-11-28 | 2013-01-23 | キヤノン株式会社 | 金属錯体化合物、有機発光素子及び表示装置 |
JP2008141000A (ja) * | 2006-12-01 | 2008-06-19 | Canon Inc | 有機発光素子 |
JP2008288254A (ja) * | 2007-05-15 | 2008-11-27 | Canon Inc | 有機el素子 |
JP5053713B2 (ja) * | 2007-05-30 | 2012-10-17 | キヤノン株式会社 | リン光発光材料、それを用いた有機電界発光素子及び画像表示装置 |
US8034465B2 (en) * | 2007-06-20 | 2011-10-11 | Global Oled Technology Llc | Phosphorescent oled having double exciton-blocking layers |
US20090066234A1 (en) | 2007-07-05 | 2009-03-12 | Hyun Sik Chae | Light emitting devices and compositions |
JP5305637B2 (ja) | 2007-11-08 | 2013-10-02 | キヤノン株式会社 | 有機金属錯体及びこれを用いた有機発光素子並びに表示装置 |
US20090191427A1 (en) * | 2008-01-30 | 2009-07-30 | Liang-Sheng Liao | Phosphorescent oled having double hole-blocking layers |
JP5472121B2 (ja) | 2009-01-28 | 2014-04-16 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置および照明装置、ならびに有機エレクトロルミネッセンス素子の製造方法 |
US9617255B2 (en) | 2009-02-06 | 2017-04-11 | Konica Minolta, Inc. | Organic electroluminescent element, and illumination device and display device each comprising the element |
EP2453496B1 (en) | 2009-07-07 | 2018-11-14 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, novel compound, lighting device and display device |
WO2011024737A1 (ja) | 2009-08-27 | 2011-03-03 | 独立行政法人産業技術総合研究所 | イリジウム錯体ならびに該化合物からなる発光材料 |
WO2011024761A1 (ja) | 2009-08-27 | 2011-03-03 | 住友化学株式会社 | 金属錯体組成物及び錯体高分子 |
JP5864525B2 (ja) | 2010-03-23 | 2016-02-17 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネセンスデバイス用材料 |
TW201223956A (en) * | 2010-08-13 | 2012-06-16 | Solvay | Light emitting materials for electronics |
US9923154B2 (en) | 2011-02-16 | 2018-03-20 | Konica Minolta, Inc. | Organic electroluminescent element, lighting device, and display device |
JP5742586B2 (ja) | 2011-08-25 | 2015-07-01 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
US9627653B2 (en) | 2011-11-14 | 2017-04-18 | Konica Minolta, Inc. | Organic electroluminescence element and planar light-emitting body each having light extraction sheet |
JP5880274B2 (ja) | 2012-05-21 | 2016-03-08 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP5849867B2 (ja) | 2012-06-21 | 2016-02-03 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
KR102102103B1 (ko) * | 2012-10-09 | 2020-04-20 | 메르크 파텐트 게엠베하 | 금속 착물 |
JP6428267B2 (ja) | 2012-12-10 | 2018-11-28 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
EP2930763B1 (en) | 2012-12-10 | 2020-07-29 | Konica Minolta, Inc. | Organic electroluminescence element, illumination device and display device |
JP5911418B2 (ja) | 2012-12-27 | 2016-04-27 | キヤノン株式会社 | 有機発光素子 |
JP5818870B2 (ja) | 2012-12-27 | 2015-11-18 | キヤノン株式会社 | 有機発光素子及び表示装置 |
JP5911419B2 (ja) | 2012-12-27 | 2016-04-27 | キヤノン株式会社 | 有機発光素子及び表示装置 |
JP6071569B2 (ja) | 2013-01-17 | 2017-02-01 | キヤノン株式会社 | 有機発光素子 |
JP6222931B2 (ja) | 2013-01-21 | 2017-11-01 | キヤノン株式会社 | 有機発光素子 |
JP5984689B2 (ja) | 2013-01-21 | 2016-09-06 | キヤノン株式会社 | 有機金属錯体及びこれを用いた有機発光素子 |
JP6095390B2 (ja) | 2013-02-06 | 2017-03-15 | キヤノン株式会社 | 有機発光素子及び表示装置 |
GB2515491B (en) * | 2013-06-24 | 2015-11-18 | Cambridge Display Tech Ltd | Phosphorescent light-emitting compounds and their use in light-emitting devices |
JP6372084B2 (ja) * | 2014-01-22 | 2018-08-15 | セイコーエプソン株式会社 | 発光装置、及び電子機器 |
KR102418886B1 (ko) * | 2014-12-29 | 2022-07-08 | 엘지디스플레이 주식회사 | 인광 화합물과 이를 이용한 발광다이오드 및 표시장치 |
WO2017016634A1 (de) * | 2015-07-30 | 2017-02-02 | Merck Patent Gmbh | Elektrolumineszierende überbrückte metallkomplexe zur verwendung in elektronischen vorrichtungen |
US11555048B2 (en) * | 2016-12-01 | 2023-01-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10745431B2 (en) * | 2017-03-08 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
GB2564490A (en) * | 2017-07-14 | 2019-01-16 | Sumitomo Chemical Co | Light-emitting compound |
KR102568783B1 (ko) * | 2018-03-22 | 2023-08-22 | 삼성디스플레이 주식회사 | 유기금속 화합물, 이를 포함한 유기 발광 소자 및 상기 유기 발광 소자를 포함한 유기 발광 장치 |
KR20200020061A (ko) * | 2018-08-16 | 2020-02-26 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
CN109232309A (zh) * | 2018-10-15 | 2019-01-18 | 安徽绩溪县徽煌化工有限公司 | 一种提高1-四氢萘酮肟产出率及纯化的加工方法 |
WO2020184369A1 (ja) * | 2019-03-11 | 2020-09-17 | 東レ株式会社 | ピロメテン金属錯体、ピロメテン化合物、発光素子材料、発光素子、表示装置および照明装置 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000005859A (ja) * | 1998-06-19 | 2000-01-11 | Toshiba Corp | 電子機器とその製造方法及び金型装置 |
JP4619546B2 (ja) | 1999-03-23 | 2011-01-26 | ザ ユニバーシティー オブ サザン カリフォルニア | 有機ledの燐光性ドーパントとしてのシクロメタル化金属錯体 |
AU1807201A (en) * | 1999-12-01 | 2001-06-12 | Trustees Of Princeton University, The | Complexes of form L2MX as phosphorescent dopants for organic leds |
JP2001181616A (ja) | 1999-12-27 | 2001-07-03 | Fuji Photo Film Co Ltd | オルトメタル化パラジウム錯体からなる発光素子材料および発光素子 |
US6821645B2 (en) * | 1999-12-27 | 2004-11-23 | Fuji Photo Film Co., Ltd. | Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex |
JP2001181617A (ja) | 1999-12-27 | 2001-07-03 | Fuji Photo Film Co Ltd | オルトメタル化白金錯体からなる発光素子材料および発光素子 |
US20020121638A1 (en) * | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
JP3345719B2 (ja) * | 2000-07-04 | 2002-11-18 | コナミ株式会社 | ゲーム制御方法、ゲーム装置、及び記録媒体 |
CN100505375C (zh) * | 2000-08-11 | 2009-06-24 | 普林斯顿大学理事会 | 有机金属化合物和发射转换有机电致磷光 |
JP4154139B2 (ja) * | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子 |
JP4154140B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物 |
JP4460743B2 (ja) * | 2000-09-29 | 2010-05-12 | 富士フイルム株式会社 | イリジウム錯体またはその互変異性体の製造方法 |
EP1348711B1 (en) | 2000-11-30 | 2018-06-13 | Canon Kabushiki Kaisha | Luminescent element and display |
JP4154145B2 (ja) * | 2000-12-01 | 2008-09-24 | キヤノン株式会社 | 金属配位化合物、発光素子及び表示装置 |
JP2003007469A (ja) * | 2001-06-25 | 2003-01-10 | Canon Inc | 発光素子及び表示装置 |
-
2001
- 2001-06-25 JP JP2001190662A patent/JP2003007469A/ja active Pending
-
2002
- 2002-06-17 DE DE60231117T patent/DE60231117D1/de not_active Expired - Lifetime
- 2002-06-17 EP EP02738730A patent/EP1400514B1/en not_active Expired - Lifetime
- 2002-06-17 US US10/181,342 patent/US6824894B2/en not_active Expired - Lifetime
- 2002-06-17 KR KR1020037016545A patent/KR100747060B1/ko active IP Right Grant
- 2002-06-17 CN CNB028087011A patent/CN100500656C/zh not_active Expired - Fee Related
- 2002-06-17 WO PCT/JP2002/006001 patent/WO2003000661A1/ja active Application Filing
- 2002-06-17 AT AT02738730T patent/ATE422493T1/de not_active IP Right Cessation
-
2004
- 2004-09-17 US US10/942,861 patent/US7078115B2/en not_active Expired - Fee Related
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100362006C (zh) * | 2005-09-16 | 2008-01-16 | 中国科学院长春应用化学研究所 | 树枝状铱配合物及使用该化合物的有机电致发光器件 |
CN102859743A (zh) * | 2010-04-28 | 2013-01-02 | 联邦科学和工业研究组织 | 基于磷光铱和相关第viii族金属多环化合物的电致发光装置 |
CN102859743B (zh) * | 2010-04-28 | 2015-09-23 | 联邦科学和工业研究组织 | 基于磷光铱和相关第viii族金属多环化合物的电致发光装置 |
CN103650194A (zh) * | 2011-05-12 | 2014-03-19 | 剑桥显示技术有限公司 | 有机发光材料和器件 |
CN108467414A (zh) * | 2011-08-01 | 2018-08-31 | 通用显示公司 | 用于有机发光二极管的材料 |
CN108467414B (zh) * | 2011-08-01 | 2022-09-23 | 通用显示公司 | 用于有机发光二极管的材料 |
WO2018108109A1 (zh) * | 2016-12-13 | 2018-06-21 | 广州华睿光电材料有限公司 | 过渡金属配合物及其应用、混合物、有机电子器件 |
CN109790193A (zh) * | 2016-12-13 | 2019-05-21 | 广州华睿光电材料有限公司 | 过渡金属配合物及其应用、混合物、有机电子器件 |
CN109790193B (zh) * | 2016-12-13 | 2022-03-22 | 广州华睿光电材料有限公司 | 过渡金属配合物及其应用、混合物、有机电子器件 |
Also Published As
Publication number | Publication date |
---|---|
EP1400514B1 (en) | 2009-02-11 |
EP1400514A1 (en) | 2004-03-24 |
DE60231117D1 (de) | 2009-03-26 |
JP2003007469A (ja) | 2003-01-10 |
CN100500656C (zh) | 2009-06-17 |
US20050085654A1 (en) | 2005-04-21 |
US6824894B2 (en) | 2004-11-30 |
US20030235712A1 (en) | 2003-12-25 |
KR20040010735A (ko) | 2004-01-31 |
ATE422493T1 (de) | 2009-02-15 |
US7078115B2 (en) | 2006-07-18 |
WO2003000661A1 (fr) | 2003-01-03 |
KR100747060B1 (ko) | 2007-08-07 |
EP1400514A4 (en) | 2005-04-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1503785A (zh) | 金属配位化合物及电致发光装置 | |
JP4438042B2 (ja) | 金属配位化合物、電界発光素子及び表示装置 | |
JP4006335B2 (ja) | 発光素子及び表示装置 | |
JP4307001B2 (ja) | 金属配位化合物、電界発光素子及び表示装置 | |
JP4154145B2 (ja) | 金属配位化合物、発光素子及び表示装置 | |
JP4550160B2 (ja) | 有機電界発光素子用化合物及び有機電界発光素子 | |
US6733905B2 (en) | Metal coordination compound, luminescence device and display apparatus | |
CN1374315A (zh) | 金属配位化合物,发光器件和显示设备 | |
JP5526074B2 (ja) | 有機エレクトロルミネッセンス装置に用いられる化合物及び有機エレクトロルミネッセンス装置 | |
EP1191613B1 (en) | Luminescence device, display apparatus and metal coordination compound | |
JP4593631B2 (ja) | 有機電界発光素子用化合物及び有機電界発光素子 | |
JP5127206B2 (ja) | 金属錯体化合物、有機発光素子及び表示装置 | |
JP4519946B2 (ja) | 有機電界発光素子用化合物及び有機電界発光素子 | |
JP4154139B2 (ja) | 発光素子 | |
EP1783133A1 (en) | Red phosphorescent compound and organic electroluminescent device using the same | |
US20020100906A1 (en) | Metal coordination compound, luminescence device and display apparatus | |
JP2003342284A (ja) | 金属配位化合物、発光素子及び表示装置 | |
JP4035372B2 (ja) | 発光素子 | |
KR20080085000A (ko) | 유기 전계 발광소자 | |
CN1413426A (zh) | 作为有机发光器件的磷光掺杂剂l2mx形式的络合物 | |
CN1648200A (zh) | 用于有机电致发光器件的苯基吡啶-铱金属配合物及使用该配合物的有机电致发光器件 | |
JP2007302565A (ja) | 金属錯体、発光素子及び画像表示装置 | |
KR100729739B1 (ko) | 금속 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
JP2005170851A (ja) | 金属配位化合物、有機発光素子及び画像表示装置 | |
KR100729737B1 (ko) | 금속 화합물 및 이를 포함하는 유기 전계 발광 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20090617 Termination date: 20190617 |