US20030205707A1 - Electroluminescent materials - Google Patents
Electroluminescent materials Download PDFInfo
- Publication number
- US20030205707A1 US20030205707A1 US10/137,272 US13727202A US2003205707A1 US 20030205707 A1 US20030205707 A1 US 20030205707A1 US 13727202 A US13727202 A US 13727202A US 2003205707 A1 US2003205707 A1 US 2003205707A1
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- United States
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- emissive
- halogen
- alkyl
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 29
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 239000002019 doping agent Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 10
- 239000003446 ligand Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 9
- 238000005401 electroluminescence Methods 0.000 claims description 6
- HRQXKKFGTIWTCA-UHFFFAOYSA-L beryllium;2-pyridin-2-ylphenolate Chemical compound [Be+2].[O-]C1=CC=CC=C1C1=CC=CC=N1.[O-]C1=CC=CC=C1C1=CC=CC=N1 HRQXKKFGTIWTCA-UHFFFAOYSA-L 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000001771 vacuum deposition Methods 0.000 claims description 4
- HPDNGBIRSIWOST-UHFFFAOYSA-N 2-pyridin-2-ylphenol Chemical compound OC1=CC=CC=C1C1=CC=CC=N1 HPDNGBIRSIWOST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052790 beryllium Inorganic materials 0.000 claims description 3
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 150000005045 1,10-phenanthrolines Chemical class 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000004528 spin coating Methods 0.000 claims 1
- 238000000859 sublimation Methods 0.000 claims 1
- 230000008022 sublimation Effects 0.000 claims 1
- 238000007740 vapor deposition Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000010409 thin film Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 0 [1*]C1=C2OC34OC5=C([14*])C([13*])=C([12*])C([11*])=C5C5=C([10*])/C([9*])=C([8*])/C(=N/53)C3=C([7*])C([6*])=C([5*])C(=N34)C2=C([4*])C([3*])=C1[2*].[1*]C1=C2OC34OC5=C([14*])C([13*])=C([12*])C([11*])=C5C5=C([10*])/C([9*])=C6/C(/[8*])=C(/[7*])C7=C(\C6=N/53)N4=C(C([5*])=C7[6*])C2=C([4*])C([3*])=C1[2*] Chemical compound [1*]C1=C2OC34OC5=C([14*])C([13*])=C([12*])C([11*])=C5C5=C([10*])/C([9*])=C([8*])/C(=N/53)C3=C([7*])C([6*])=C([5*])C(=N34)C2=C([4*])C([3*])=C1[2*].[1*]C1=C2OC34OC5=C([14*])C([13*])=C([12*])C([11*])=C5C5=C([10*])/C([9*])=C6/C(/[8*])=C(/[7*])C7=C(\C6=N/53)N4=C(C([5*])=C7[6*])C2=C([4*])C([3*])=C1[2*] 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007787 solid Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005424 photoluminescence Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- DZOUBSHHDJLOCP-UHFFFAOYSA-N CC(C)(C)C1=CC2=N3C(=C1)C1=N4C(=C\C(C(C)(C)C)=C/1)\C1=CC=CC=C1OC3\4OC1=CC=CC=C12 Chemical compound CC(C)(C)C1=CC2=N3C(=C1)C1=N4C(=C\C(C(C)(C)C)=C/1)\C1=CC=CC=C1OC3\4OC1=CC=CC=C12 DZOUBSHHDJLOCP-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000003057 platinum Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- -1 α-naphthylphenylbiphenyl amine Chemical class 0.000 description 3
- BURSNCWCYGTJNM-UHFFFAOYSA-L C1=CC=C(C2=CC3=N4C5=C2/C=C\C2=C(C6=CC=CC=C6)\C=C6\C7=CC=CC=C7O[Pt]4(OC4=CC=CC=C43)/N6=C52)C=C1 Chemical compound C1=CC=C(C2=CC3=N4C5=C2/C=C\C2=C(C6=CC=CC=C6)\C=C6\C7=CC=CC=C7O[Pt]4(OC4=CC=CC=C43)/N6=C52)C=C1 BURSNCWCYGTJNM-UHFFFAOYSA-L 0.000 description 2
- AUGYFZNGFFJSPZ-UHFFFAOYSA-N CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC(C3=CC=CC=C3O)=N2)=NC(C2=CC=CC=C2O)=C1 Chemical compound CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC(C3=CC=CC=C3O)=N2)=NC(C2=CC=CC=C2O)=C1 AUGYFZNGFFJSPZ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- SNGOTMASNQJGQE-UHFFFAOYSA-N 2,9-bis(2-methoxyphenyl)-4,7-diphenyl-1,10-phenanthroline Chemical compound COC1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=CC=2C3=NC(=CC=2C=2C=CC=CC=2)C=2C(=CC=CC=2)OC)C3=N1 SNGOTMASNQJGQE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- JGQVSEUPZBMOAP-UHFFFAOYSA-N 4-tert-butyl-2-[4-tert-butyl-6-(2-methoxyphenyl)pyridin-2-yl]-6-(2-methoxyphenyl)pyridine Chemical compound COC1=CC=CC=C1C1=CC(C(C)(C)C)=CC(C=2N=C(C=C(C=2)C(C)(C)C)C=2C(=CC=CC=2)OC)=N1 JGQVSEUPZBMOAP-UHFFFAOYSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- RCSFSIJTIVNFIL-UHFFFAOYSA-N C1=CC=C(C2=CC3=N4C5=C2/C=C\C2=C(C6=CC=CC=C6)\C=C6\C7=CC=CC=C7OC4(OC4=CC=CC=C43)/N6=C52)C=C1 Chemical compound C1=CC=C(C2=CC3=N4C5=C2/C=C\C2=C(C6=CC=CC=C6)\C=C6\C7=CC=CC=C7OC4(OC4=CC=CC=C43)/N6=C52)C=C1 RCSFSIJTIVNFIL-UHFFFAOYSA-N 0.000 description 1
- ZHEIJKQGCFVASM-UHFFFAOYSA-L CC(C)(C)C1=CC2=N3C(=C1)C1=N4C(=C\C(C(C)(C)C)=C/1)\C1=CC=CC=C1O[Pt]3\4OC1=CC=CC=C12 Chemical compound CC(C)(C)C1=CC2=N3C(=C1)C1=N4C(=C\C(C(C)(C)C)=C/1)\C1=CC=CC=C1O[Pt]3\4OC1=CC=CC=C12 ZHEIJKQGCFVASM-UHFFFAOYSA-L 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 229910020427 K2PtCl4 Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- CLHHRZSJZXBQDW-UHFFFAOYSA-N OC1=CC=CC=C1C1=NC2=C(/C=C\C3=C(C4=CC=CC=C4)\C=C(C4=CC=CC=C4O)\N=C23)C(C2=CC=CC=C2)=C1 Chemical compound OC1=CC=CC=C1C1=NC2=C(/C=C\C3=C(C4=CC=CC=C4)\C=C(C4=CC=CC=C4O)\N=C23)C(C2=CC=CC=C2)=C1 CLHHRZSJZXBQDW-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001875 compounds Chemical group 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- DQMSBDXZGJIRDX-UHFFFAOYSA-N methanol;propan-2-ol;propan-2-one Chemical compound OC.CC(C)O.CC(C)=O DQMSBDXZGJIRDX-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition 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
- 238000005019 vapor deposition process Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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Definitions
- LED light-emitting diode
- OLEDs organic light-emitting devices
- gallium arsenide-based LEDs in the market are commonly available with efficiencies in some spectral regions exceeding conventional filtered fluorescent lamps.
- inorganic semi-conductor materials are not compatible for large-area assembled displays.
- some phosphorescent materials have intrinsic disadvantages, such as saturation of emission sites due to excessively long lifetimes as well as triplet-triplet annihilation and concentration quenching arising from strong intermolecular interactions at high doping levels ( Phys. Rev. B. 60, 14422, (1999)).
- the main objective of this invention is to prepare organic light-emitting devices (OLEDs) doped with new light-emitting materials.
- OLEDs organic light-emitting devices
- the devices exhibit low turn-on voltages and high luminance and efficiencies.
- An object of the present invention is to provide thermally stable, moisture-resistant metal-chelated materials that can be deposited as a thin layer of known thickness by a vapor deposition process.
- the present invention concerns the design of high luminous dopants, which can be used at low concentration levels in light-emitting devices.
- M represents Group 10 metal (including platinum) and R 1 -R 14 are each independently selected from the group consisting of hydrogen; halogen; alkyl; substituted alkyl; aryl; substituted aryl, with substitutents selected from the group consisting of halogen, lower alkyl and recognized donor and acceptor groups.
- Embodiments of the present invention includes, but is not limited to, OLEDs comprising heterostructures for producing electroluminescence which contain anode (ITO glass substance), hole transport layer (NPB ( ⁇ -naphthylphenylbiphenyl amine)), matrix emissive layer [host material (beryllium bis(2-(2′-hydroxyphenyl)pyridine) (Bepp 2 )) with different concentration of dopants as illustrated by formula I and II herein], charge transport layer (lithium fluoride) and cathode (aluminum metal).
- OLEDs comprising heterostructures for producing electroluminescence which contain anode (ITO glass substance), hole transport layer (NPB ( ⁇ -naphthylphenylbiphenyl amine)), matrix emissive layer [host material (beryllium bis(2-(2′-hydroxyphenyl)pyridine) (Bepp 2 )) with different concentration of dopants as illustrated by formula I and II herein], charge transport
- FIG. 2 Emission spectra of complex 1b in CH 2 Cl 2 and as thin film at 298 K
- FIG. 3 Emission spectra of complex 2b in CH 2 Cl 2 and as thin film at 298 K
- FIG. 4 TGA thermograms of complexes 1b and 2b under nitrogen and air
- FIG. 5 Schematic diagram of OLED in present invention
- FIG. 6 Electroluminescent spectrum, current density-voltage-luminance curves of Device A containing complex 1b (doping level 0.3 wt %)
- FIG. 7 Electroluminescent spectrum, current density-voltage-luminance curves of Device B containing complex 1b (doping level 1.0 wt %)
- FIG. 8 Electroluminescent spectrum of Device C containing complex 1b (doping level 2.0 wt %)
- the inventions are generally related to syntheses, spectral characterization, phosphorescence, light-emitting properties of the new light-emitting materials, and their applications in OLEDs.
- the examples are set forth to aid in an understanding of the inventions but are not intended to, and should not be interpreted to, limit in any way the invention as set forth in the claims which follow thereafter.
- FIG. 5 An electroluminescent device according to this invention is schematically illustrated in FIG. 5.
- the device A was assembled as follows: indium tin oxide (ITO) electrode with sheet resistance of 20 ⁇ /square on glass substrate, a hole transport material NPB ( ⁇ -naphthylphenylbiphenyl amine) with thickness of 500 ⁇ , an emitting layer made of mixture of 0.3 wt. % complex 1b and blue luminescent material Bepp 2 (beryllium bis(2-(2′-hydroxyphenyl)pyridine) with 400 ⁇ thickness, an enhanced charge transport layer LiF with thickness of 15 ⁇ , and aluminum layer with 2000 ⁇ thickness.
- the metal and organic layers were laminated in sequence under 5 ⁇ 10 ⁇ 6 mbar without breaking vacuum between different vacuum deposition processes.
- the layers were deposited at rates of 2 or 5 ⁇ per second.
- the emissive area of the device as defined by overlapping area of cathode and anode was 3 ⁇ 3 mm 2 .
- the ITO coated glass slides were cleaned with organic solvents (acetone-isopropanol-methanol), deionized water, followed by ultra-violet-ozone cleaner.
- EL spectra and current density-voltage-luminance characteristics of the devices were measured with a spectrophotometer and a computer-controlled direct-current power supply respectively at room temperature.
- the device external efficiencies increase when the doping concentration levels of complex 1b were adjusted from 2 to 0.3 wt %.
- the specific examples are further illustrated as follows:
- FIG. 6 The performances of device A with 0.3 wt % doping level of complex 1b are shown in FIG. 6. Two intense EL emissions at 453 and 540 nm are observed when the device was driven under forward bias. The current density-voltage-luminance characteristics curves of device A are also shown. The turn-on voltage is approximately 6-7 V. The maximum efficiency of the device was 4.1 cd/A at luminance of 2849 cd/m 2 . The maximum luminance of 9325 cd/M 2 was obtained at driving voltage of 10 V.
- FIG. 7 The performances of device B with 1.0 wt % doping level of complex 1b are shown in FIG. 7.
- the device exhibits an intense EL emission peak at 546 nm and a weak emission at 457 nm.
- the onset voltage of device B was approximately at 6-7 V.
- the efficiency and maximum luminance were 1.9 cd/A at luminance of 1927 cd/m 2 and 6563 cd/M 2 at driving voltage of 9.5 V respectively.
- doping level of greater than 5% is reported to achieve dopant emission in organic or polymeric light-emitting devices.
- the OLEDs show virtually complete emission of complex 1b when the doping level is around 2% and the efficiencies of devices increase from 1.5 to 4.1 cd/A when the doping levels of complex are decreased from 2.0 to 0.3 wt %.
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Abstract
Description
- The present invention relates to light-emitting materials, which can be deposited as a thin layer by vacuum deposition, and which can be used as effective dopants in organic light-emitting devices (OLEDs).
- The progress of light-emitting diode (LED) over the past two decades has primarily focused on inorganic types because early development in organic light-emitting devices (OLEDs) resulted in poor fabrication and packaging, and short lifetimes. Today, gallium arsenide-based LEDs in the market are commonly available with efficiencies in some spectral regions exceeding conventional filtered fluorescent lamps. However, in the development of light-emitting materials for display technology, inorganic semi-conductor materials are not compatible for large-area assembled displays.
- Pope et al. at New York University demonstrated organic electroluminescence in the 1960s based on anthracene materials (J. Chem. Phys. 38, 2042, (1963)). Much progress have been made since the discovery of the tris(8-hydroxyquinolato)aluminum (Alq3) based thin film device by C. W. Tang et al. at Kodak (Appl. Phys. Lett. 51, 913, (1987)). These contributed largely to the continuous discovery of new and improved electroluminescent materials. From small fluorescent molecules to conjugated polymers, many OLEDs have been shown to exhibit sufficient brightness, remarkable efficiencies, good operating lifetimes and desirable ranges of color emission.
- Organic light-emitting devices containing metal complexes are of particular interest because of their unusual chemical and electronic properties. Some compounds bearing heavy metals exhibit potential advantages for OLEDs owing to their high internal quantum efficiencies. Conventionally, fluorescent materials are employed as dopants in emissive hosts. Singlet excitons (maximum theoretical internal quantum efficiency=25%) are formed after recombination of hole and electron to emit electroluminescence via dipole-dipole interaction through Forster mechanism (U.S. Pat. No. 6,310,360). Whereas, for heavy metal complexes, strong spin-orbit coupling can lead to singlet-triplet state mixing, which can result in high-efficiency electrophosphorescence in OLEDs (theoretical internal quantum efficiency up to 100%) (Nature, 395, 151, (1998); Synthetic Metals, 93, 245, (1998); Appl. Phys. Lett. 77, 904, (2000)).
- However, some phosphorescent materials have intrinsic disadvantages, such as saturation of emission sites due to excessively long lifetimes as well as triplet-triplet annihilation and concentration quenching arising from strong intermolecular interactions at high doping levels (Phys. Rev. B. 60, 14422, (1999)).
- For example, quadridentate azomethine-zinc complexes have been used as blue light emitters in organic light-emitting devices, which exhibit maximum luminance of approximately 1000 cd/m2 only (Jpn. J. Appl. Phys., 32, L511 (1993); U.S. Pat. No. 5,432,014).
- Azomethine-aluminum/gallium complexes have been employed in OLEDs as emissive materials. The current density of the device containing azomethine-gallium complex is 1 mA/cm2 at 10 V and the electroluminescence is greenish blue (U.S. Pat. No. 6,316,130).
- It is therefore desirable to develop emissive dopant materials that can permit efficient energy transfer between the host and dopant in OLEDs, while causing little or no self-quenching even at sufficiently high doping concentrations.
- Examples of objects of the present invention in embodiments thereof include:
- The main objective of this invention is to prepare organic light-emitting devices (OLEDs) doped with new light-emitting materials. The devices exhibit low turn-on voltages and high luminance and efficiencies.
- An object of the present invention is to provide thermally stable, moisture-resistant metal-chelated materials that can be deposited as a thin layer of known thickness by a vapor deposition process.
- Further, the present invention concerns the design of high luminous dopants, which can be used at low concentration levels in light-emitting devices.
-
- wherein M represents
Group 10 metal (including platinum) and R1-R14 are each independently selected from the group consisting of hydrogen; halogen; alkyl; substituted alkyl; aryl; substituted aryl, with substitutents selected from the group consisting of halogen, lower alkyl and recognized donor and acceptor groups. - Embodiments of the present invention includes, but is not limited to, OLEDs comprising heterostructures for producing electroluminescence which contain anode (ITO glass substance), hole transport layer (NPB (α-naphthylphenylbiphenyl amine)), matrix emissive layer [host material (beryllium bis(2-(2′-hydroxyphenyl)pyridine) (Bepp2)) with different concentration of dopants as illustrated by formula I and II herein], charge transport layer (lithium fluoride) and cathode (aluminum metal).
-
- The present invention provides new materials for applications as emissive dopants in electroluminescent devices. The invention includes the synthetic methods for these novel complexes plus their use as light-emitting materials. The devices of the present invention can be applied to field of display, light-emitter, display board for sign lamp, or light source for liquid crystal display.
- FIG. 1. Absorption spectra of
complexes 1b & 2b in CH2Cl2 - FIG. 2. Emission spectra of
complex 1b in CH2Cl2 and as thin film at 298 K - FIG. 3. Emission spectra of
complex 2b in CH2Cl2 and as thin film at 298 K - FIG. 4. TGA thermograms of
complexes - FIG. 5. Schematic diagram of OLED in present invention
- FIG. 6. Electroluminescent spectrum, current density-voltage-luminance curves of Device
A containing complex 1b (doping level 0.3 wt %) - FIG. 7. Electroluminescent spectrum, current density-voltage-luminance curves of Device
B containing complex 1b (doping level 1.0 wt %) - FIG. 8. Electroluminescent spectrum of Device
C containing complex 1b (doping level 2.0 wt %) - The inventions are generally related to syntheses, spectral characterization, phosphorescence, light-emitting properties of the new light-emitting materials, and their applications in OLEDs. The examples are set forth to aid in an understanding of the inventions but are not intended to, and should not be interpreted to, limit in any way the invention as set forth in the claims which follow thereafter.
- The examples given illustrate the synthetic methods of ligands la and 2a, and the
platinum complexes -
- A mixture of 6,6′-bis(2-methoxyphenyl)-4,4′-bis(tert-butyl)-2,2′-bipyridine (1 g) in hydrobromic acid (47%, 20 mL) was refluxed for 12 hours. This was cooled to room temperature and was neutralized with an aqueous saturated Na2CO3 solution at room temperature. The organic product was extracted with chloroform and the extracts were washed with deionized water (50 mL x 2), dried over anhydrous Na2SO4, and a solid residue was obtained by removal of solvent. Crystalline product of la was obtained by recrystallization from a methanol/dichloromethane solution. EI-MS (m/z): 452 [M]+. 1H NMR (CDCl3, δ, ppm): 14.45 (2H, s, OH), 8.16 (2H, d, J=1.4 Hz, ArH), 7.97 (2H, d, J=1.3 Hz, ArH), 7.90 (2H, dd, J=8.0 Hz, J=1.4 Hz, ArH), 7.34 (2H, td, J=8.4 Hz, J=1.5 Hz, ArH), 7.07 (2H, dd, J=8.2 Hz, J=1.6 Hz, ArH), 6.96 (2H, td, J=8.1 Hz, J=1.2 Hz, ArH), 1.47 (18H, s, tBu). 13C NMR (CDCl3, δ, ppm): 163.3, 159.7, 157.5, 152.2, 131.5, 126.5, 119.2, 118.9, 118.4, 116.4, 35.6, 30.6.
-
- The synthetic method of
metal complex 1b is described. A mixture of NaOMe (0.014 g, 0.25 mmol) and the ligand la (0.113 g, 0.25 mmol) in methanol (20 mL) was stirred for 2 hours. An acetonitrile solution (20 mL) of Pt(CH3CN)2Cl2 (0.25 mmol) was added to the methanolic suspension, which was refluxed for 24 hours. The resulting suspension was filtered and concentrated to about 5 mL. Upon addition of diethyl ether, a brown-yellow solid was obtained. The crude product was recrystallized by diffusion of diethyl ether into a dichloromethane solution to afford yellow crystals. FAB-MS (m/z): 645 [M]+, 1292 (2M++2), 1938 (3M++3). 1H NMR (CDCl3, δ, ppm): 8.32 (d, 2H, J=1.41 Hz ArH), 8.01 (d, 2H, J=7.25 Hz, ArH), 7.85 (d, 2H, J=1.68 Hz, ArH), 7.48 (dd, 2H, J=7.38 Hz, J=1.13 Hz, ArH), 7.38 (td, 2H, J=5.35, 1.61 Hz, ArH), 6.79 (td, 2H, J=5.40, 1.35 Hz, ArH), 1.54 (s, 18H, tBu). 13C NMR (CDCl3, δ, ppm): 162.745, 159.105, 155.291, 149.851, 131.269, 128.005, 124.060, 120.465, 120.402, 116.302, 116.148, 30.402, 29.715. FTIR (KBr, cm−1): 3086 w, 2953 m, 1612 w, 1528 s, 1351 s, 1034 m, 885 w, 723 m. -
- In a 100 mL round-bottom flask equipped with a reflux condenser, 2,9-bis(2-methoxyphenyl)-4,7-diphenyl-1,10-phenanthroline (finely ground, 2 g, 3.7 mmol) and pyridinium hydrochloride (4.23 g, 37 mmol) were mixed. The mixture was heated under nitrogen flow to 210° C. for 36 hours. After cooling, water (30 mL) was added and the aqueous solution was extracted with chloroform (3×30 mL). Combined organic extracts were washed with saturated sodium bicarbonate solution (5×30 mL) and water (3×30 mL), dried over anhydrous magnesium sulfate and evaporated to give a bright yellow solid. Chromatography over silica gel using n-hexane: dichloromethane (1:2) as eluent afforded 0.99 g of a yellow solid. FAB-MS (m/z): 517 [M+H]+. 1H NMR (300 MHz, CDCl3, δ, ppm): 14.69 (2H, s, OH), 8.52 (2H, s, ArH), 8.41 (2H, dd, J=8.0, 1.3 Hz, ArH), 7.90 (2H, s, ArH), 7.71 (4H, d, J=7.4 Hz), 7.64 (6H, m, ArH), 7.43 (2H, td, J=7.7, 1.5 Hz, ArH), 7.10 (2H, dd, J=7.4 Hz, 1.3 Hz, ArH), 7.04 (2H, td, J=7.5, 1.3 Hz, ArH). 13C NMR (600 MHz, CDCl3): δ=160.5, 157.7, 150.3, 142.8, 137.8, 132.2, 129.6, 128.9, 128.8, 127.1, 125.7, 123.7, 120.6, 119.4, 119.2, 118.9.
-
- K2PtCl4 (0.08 g, 0.19 mmol) and 2a (0.1 g, 0.19 mmol) were refluxed in glacial acetic acid (10 mL) for 2 days. After cooling, the resulting suspension was collected by filtration, washed with acetic acid and water successively and then dried under vacuum to afford a brown solid. The crude product was purified by chromatography on a silica gel column with dichloromethane as eluent. The product was recrystallized by slow evaporation of a dichloromethane solution to afford red crystals. FAB-MS: m/z=710 [M+H]+. 1H NMR (270 MHz, DMSO-d6) 8.81 (2H, s, ArH), 8.56 (2H, d, J=8.9 Hz, ArH), 8.01 (2H, s, ArH), 7.86 (4H, m, ArH), 7.71 (6H, dd, J=4.9, 2.0 Hz, ArH), 7.44 (2H, t, J 7.4 Hz, ArH), 7.24 (2H, d, J=8.2 Hz, ArH), 6.80 (2H, t, J=7.6 Hz, ArH).
- The spectral characteristics of the
platinum complexes TABLE 1 UV/vis absorption data of 1b and 2b in CH2Cl2 Complexes λmax/nm (ε/104 × dm3mol−1cm−1) 1b 255 (3.80), 315 (1.75), 400 (0.82), 480 (0.25), 505 (0.22) 2b 291 (3.92), 315 (3.40), 325 (3.23), 352 (2.58), 375 (2.47), 420 (0.52), 488 (0.67), 504 (0.72) - The photoluminescence (PL) of the
platinum complexes complexes TABLE 2 PL properties of complexes Complexes (Measuring medium/ Emission Temperature) (Maximum/nm) Lifetime (μs) Quantum yield 1b (CH2Cl2/298 K) 595 1.9 0.1 1b (Thin Film/298 K) 599 / / 2b (CH2Cl2/298 K) 586 5.3 0.6 2b (Thin Film/298 K) 651 / / - The TGA thermograms of
complexes - An electroluminescent device according to this invention is schematically illustrated in FIG. 5. As examples of the present invention, OLEDs with configurations of ITO/NPB (α-naphthylphenylbiphenyl amine) (500 Å)/[0.3 wt % (device A), 1 wt % (device B), or 2 wt % (device C) of complex 1b]:Bepp2 (400 Å)/LiF (15 Å)/A1 (2000 Å) were prepared. The fabrication of device A (0.3 wt % of 1b) follows:
- The device A was assembled as follows: indium tin oxide (ITO) electrode with sheet resistance of 20 Ω/square on glass substrate, a hole transport material NPB (α-naphthylphenylbiphenyl amine) with thickness of 500 Å, an emitting layer made of mixture of 0.3 wt.
% complex 1b and blue luminescent material Bepp2 (beryllium bis(2-(2′-hydroxyphenyl)pyridine) with 400 Å thickness, an enhanced charge transport layer LiF with thickness of 15 Å, and aluminum layer with 2000 Å thickness. The metal and organic layers were laminated in sequence under 5×10−6 mbar without breaking vacuum between different vacuum deposition processes. The layers were deposited at rates of 2 or 5 Å per second. The emissive area of the device as defined by overlapping area of cathode and anode was 3×3 mm2. The ITO coated glass slides were cleaned with organic solvents (acetone-isopropanol-methanol), deionized water, followed by ultra-violet-ozone cleaner. EL spectra and current density-voltage-luminance characteristics of the devices were measured with a spectrophotometer and a computer-controlled direct-current power supply respectively at room temperature. - For these examples, the device external efficiencies increase when the doping concentration levels of complex 1b were adjusted from 2 to 0.3 wt %. The specific examples are further illustrated as follows:
- The performances of device A with 0.3 wt % doping level of complex 1b are shown in FIG. 6. Two intense EL emissions at 453 and 540 nm are observed when the device was driven under forward bias. The current density-voltage-luminance characteristics curves of device A are also shown. The turn-on voltage is approximately 6-7 V. The maximum efficiency of the device was 4.1 cd/A at luminance of 2849 cd/m2. The maximum luminance of 9325 cd/M2 was obtained at driving voltage of 10 V. The EL color of device A is yellow (CIE coordinates: x=0.33, y=0.47).
- The performances of device B with 1.0 wt % doping level of complex 1b are shown in FIG. 7. The device exhibits an intense EL emission peak at 546 nm and a weak emission at 457 nm. The onset voltage of device B was approximately at 6-7 V. The efficiency and maximum luminance were 1.9 cd/A at luminance of 1927 cd/m2 and 6563 cd/M2 at driving voltage of 9.5 V respectively. The EL color of device B is yellow (CIE coordinates: x=0.39, y=0.54).
- Device C with 2.0 wt % doping level of complex 1b exhibits an intense EL emission peak at 548 nm with an extremely weak emission at around 450 nm (FIG. 8); EL efficiency of 1.5 cd/A was detected. Luminance of 6450 cd/m2 was observed at driving voltage of 12 V. The EL color of device C is yellow (CIE coordinates: x=0.42, y=0.56).
- Typically, doping level of greater than 5% is reported to achieve dopant emission in organic or polymeric light-emitting devices. In this invention, the OLEDs show virtually complete emission of complex 1b when the doping level is around 2% and the efficiencies of devices increase from 1.5 to 4.1 cd/A when the doping levels of complex are decreased from 2.0 to 0.3 wt %.
Claims (15)
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JP4981252B2 (en) | 2012-07-18 |
EP1499624A1 (en) | 2005-01-26 |
AU2003218866A1 (en) | 2003-11-17 |
CN100509827C (en) | 2009-07-08 |
TWI267544B (en) | 2006-12-01 |
TW200427814A (en) | 2004-12-16 |
JP2010050451A (en) | 2010-03-04 |
KR100991874B1 (en) | 2010-11-04 |
JP2005524727A (en) | 2005-08-18 |
KR20050007357A (en) | 2005-01-17 |
EP1499624B1 (en) | 2016-01-06 |
CN1649886A (en) | 2005-08-03 |
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WO2003093283A1 (en) | 2003-11-13 |
US6653654B1 (en) | 2003-11-25 |
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