JP4746854B2 - 有機発光ダイオード - Google Patents
有機発光ダイオード Download PDFInfo
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- JP4746854B2 JP4746854B2 JP2004211837A JP2004211837A JP4746854B2 JP 4746854 B2 JP4746854 B2 JP 4746854B2 JP 2004211837 A JP2004211837 A JP 2004211837A JP 2004211837 A JP2004211837 A JP 2004211837A JP 4746854 B2 JP4746854 B2 JP 4746854B2
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- JP
- Japan
- Prior art keywords
- oled
- oled according
- light emitting
- aryl
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000003446 ligand Substances 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 14
- 125000003118 aryl group Chemical class 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 238000012986 modification Methods 0.000 claims description 9
- 230000004048 modification Effects 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical group OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical class 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- -1 phenyl C1-C6 alkyl Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical group 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- 125000005595 acetylacetonate group Chemical group 0.000 claims 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 238000003786 synthesis reaction Methods 0.000 description 44
- 239000010410 layer Substances 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 33
- 239000011777 magnesium Substances 0.000 description 28
- 238000000862 absorption spectrum Methods 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 238000005424 photoluminescence Methods 0.000 description 17
- 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 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 11
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000000295 emission spectrum Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical class [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 7
- 0 *C=Cc1ccccc1 Chemical compound *C=Cc1ccccc1 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- FJXNABNMUQXOHX-UHFFFAOYSA-N 4-(9h-carbazol-1-yl)-n,n-bis[4-(9h-carbazol-1-yl)phenyl]aniline Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1N(C=1C=CC(=CC=1)C=1C=2NC3=CC=CC=C3C=2C=CC=1)C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 FJXNABNMUQXOHX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- SMTDFMMXJHYDDE-GORDUTHDSA-N 2-[(e)-prop-1-enyl]pyridine Chemical compound C\C=C\C1=CC=CC=N1 SMTDFMMXJHYDDE-GORDUTHDSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- 101000964479 Homo sapiens Zinc finger and BTB domain-containing protein 18 Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 102100040762 Zinc finger and BTB domain-containing protein 18 Human genes 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- DNJOLLNKSHWUAN-UHFFFAOYSA-N n-[4-(4-carbazol-9-ylphenyl)phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 DNJOLLNKSHWUAN-UHFFFAOYSA-N 0.000 description 2
- LBFXFIPIIMAZPK-UHFFFAOYSA-N n-[4-[4-(n-phenanthren-9-ylanilino)phenyl]phenyl]-n-phenylphenanthren-9-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=C1 LBFXFIPIIMAZPK-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SENXCDRAXNPDOK-UHFFFAOYSA-N tributyl-[(z)-2-phenylethenyl]stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=CC1=CC=CC=C1 SENXCDRAXNPDOK-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- RTSZQXSYCGBHMO-UHFFFAOYSA-N 1,2,4-trichloro-3-prop-1-ynoxybenzene Chemical compound CC#COC1=C(Cl)C=CC(Cl)=C1Cl RTSZQXSYCGBHMO-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYOQVYHOVXOXIP-ZHACJKMWSA-N 1-[(e)-2-phenylethenyl]isoquinoline Chemical compound N=1C=CC2=CC=CC=C2C=1\C=C\C1=CC=CC=C1 RYOQVYHOVXOXIP-ZHACJKMWSA-N 0.000 description 1
- CQZMITKMELUCEX-UHFFFAOYSA-N 1-[4-(9h-carbazol-1-yl)phenyl]-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 CQZMITKMELUCEX-UHFFFAOYSA-N 0.000 description 1
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-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
- UUZHEBYAHWZAMP-UHFFFAOYSA-N 2-(1-phenylprop-1-en-2-yl)pyridine Chemical compound C=1C=CC=NC=1C(C)=CC1=CC=CC=C1 UUZHEBYAHWZAMP-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- VLAOGLXJBVSETF-PKNBQFBNSA-N 2-[(e)-2-naphthalen-2-ylethenyl]pyridine Chemical compound C=1C=C2C=CC=CC2=CC=1/C=C/C1=CC=CC=N1 VLAOGLXJBVSETF-PKNBQFBNSA-N 0.000 description 1
- LCIISWPXOZNVIG-ZHACJKMWSA-N 2-[(e)-2-phenylethenyl]-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1/C=C/C1=CC=CC=C1 LCIISWPXOZNVIG-ZHACJKMWSA-N 0.000 description 1
- BZQRVLYAUYYKQM-SOFGYWHQSA-N 2-[(e)-2-phenylethenyl]-5-(trifluoromethyl)pyridine Chemical compound N1=CC(C(F)(F)F)=CC=C1\C=C\C1=CC=CC=C1 BZQRVLYAUYYKQM-SOFGYWHQSA-N 0.000 description 1
- BIAWAXVRXKIUQB-MDZDMXLPSA-N 2-[(e)-2-phenylethenyl]pyridine Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=N1 BIAWAXVRXKIUQB-MDZDMXLPSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- OWEOYUSGIQAOBA-UHFFFAOYSA-N 3-(2-methylphenyl)-n-[4-[4-[3-(2-methylphenyl)anilino]phenyl]phenyl]aniline Chemical group CC1=CC=CC=C1C1=CC=CC(NC=2C=CC(=CC=2)C=2C=CC(NC=3C=C(C=CC=3)C=3C(=CC=CC=3)C)=CC=2)=C1 OWEOYUSGIQAOBA-UHFFFAOYSA-N 0.000 description 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- MPMZSHBASKBPKF-VAWYXSNFSA-N 4-methyl-2-[(e)-2-phenylethenyl]quinoline Chemical compound N=1C2=CC=CC=C2C(C)=CC=1\C=C\C1=CC=CC=C1 MPMZSHBASKBPKF-VAWYXSNFSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- BIIIJAIDRYEBIW-CSKARUKUSA-N 5-methyl-2-[(e)-2-phenylethenyl]pyridine Chemical compound N1=CC(C)=CC=C1\C=C\C1=CC=CC=C1 BIIIJAIDRYEBIW-CSKARUKUSA-N 0.000 description 1
- DQMMBEPJQZXXGK-UHFFFAOYSA-N 9-(4-phenylphenyl)carbazole Chemical compound C1=CC=CC=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 DQMMBEPJQZXXGK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WBLCBPKLJBWTIG-UHFFFAOYSA-N C(C1c2c3cccc2)=CC=CC1N3c(cc1)ccc1N(c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound C(C1c2c3cccc2)=CC=CC1N3c(cc1)ccc1N(c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2)c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 WBLCBPKLJBWTIG-UHFFFAOYSA-N 0.000 description 1
- LCIISWPXOZNVIG-UHFFFAOYSA-N C(c1nc(cccc2)c2[s]1)=C/c1ccccc1 Chemical compound C(c1nc(cccc2)c2[s]1)=C/c1ccccc1 LCIISWPXOZNVIG-UHFFFAOYSA-N 0.000 description 1
- UUZHEBYAHWZAMP-VAWYXSNFSA-N C/C(/c1ncccc1)=C\c1ccccc1 Chemical compound C/C(/c1ncccc1)=C\c1ccccc1 UUZHEBYAHWZAMP-VAWYXSNFSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N CC(c1ncccc1)=O Chemical compound CC(c1ncccc1)=O AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- TYWOINNRTBXUMZ-UHFFFAOYSA-N C[ClH]c1nc2ccccc2[s]1 Chemical compound C[ClH]c1nc2ccccc2[s]1 TYWOINNRTBXUMZ-UHFFFAOYSA-N 0.000 description 1
- ZTNANFDSJRRZRJ-UHFFFAOYSA-N Cc1c(cccc2)c2nc(C)c1 Chemical compound Cc1c(cccc2)c2nc(C)c1 ZTNANFDSJRRZRJ-UHFFFAOYSA-N 0.000 description 1
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin Proteins 0.000 description 1
- RZIAABRFQASVSW-UHFFFAOYSA-N Isoquinoline N-oxide Chemical compound C1=CC=CC2=C[N+]([O-])=CC=C21 RZIAABRFQASVSW-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- RQBJDYBQTYEVEG-UHFFFAOYSA-O [PH3+]Cc1ccccc1 Chemical compound [PH3+]Cc1ccccc1 RQBJDYBQTYEVEG-UHFFFAOYSA-O 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 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
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 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
- 238000004821 distillation Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- KYCHGXYBBUEKJK-UHFFFAOYSA-K indium(3+);trichloride;hydrate Chemical compound O.Cl[In](Cl)Cl KYCHGXYBBUEKJK-UHFFFAOYSA-K 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 102000045222 parkin Human genes 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- RLGKSXCGHMXELQ-ZRDIBKRKSA-N trans-2-styrylquinoline Chemical compound C=1C=C2C=CC=CC2=NC=1\C=C\C1=CC=CC=C1 RLGKSXCGHMXELQ-ZRDIBKRKSA-N 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
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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Description
本発明によるリン光性Ir錯体の主たる特徴は、次式の構造(I)または(II)を有する3つの二座配位子から形成される八面体六配位子錯体にある。
Zは、窒素含有ヘテロサイクリック基を形成可能な任意の原子部分、たとえば、ピリジン、キノリン、イソキノリン、ピラジン、ピリミジン、ピロール、ピラゾール、イミダゾール、インドール、チアゾール、イソチアゾール、オキサゾール、イソオキサゾール、ベンゾチアゾール、ベンゾオキサゾール、フェナントロリンまたはその他の形のものでる。
mは、0または正の整数で、その大きさは窒素含有ヘテロサイクリック環の大きさによって決まるものである。
この合成反応を以下に示す。
この合成反応を以下に示す。
この合成反応を以下に示す。
この合成反応を以下に示す。
この合成反応を以下に示す。
この合成反応を以下に示す。
(実施例7)2−[1−プロペニル]ピリジン(PP)の合成。
この合成反応を以下に示す。
この合成反応を以下に示す。
この合成反応を以下に示す。
この合成反応を以下に示す。
この合成反応を以下に示す。
実施例1で得られるPEPを配位子(L)として使用する。実施例11の工程を使用して錯体I−1を調製すると、その収率は72%である。ジクロロメタンに溶解させたI−1錯体の紫外線吸収スペクトルおよび光ルミネッセンス(PL)発光スペクトルを、図3に示す。これによる発光は、赤色で、その最大発光波長は616nmである。1HNMR(CDCl3、500MHz)は、δ(ppm)1.81(s、6H)、5.12(s、1H)、6.56(td、J=1.5Hz、J=6.0Hz、2H)、6.73(s、2H)、6.91(d、J=5.0Hz、10H)、7.09(d、J=8.0Hz、2H)、7.29(td、J=1.5Hz、J=7.5Hz、2H)、7.78(d、J=6.0Hz、2H)であり、HRMS(m/z)計算値(C31H27IrN2O2)652.1702、実測値652.1699である。
実施例2で得られるPETPを配位子(L)として使用する。実施例11の工程を使用して錯体I−2を調製すると、その収率は70%である。ジクロロメタンに溶解させたI−2錯体の紫外線吸収スペクトルおよびPL発光スペクトルを、図5に示す。その発光は、赤色で、最大発光波長は610nmである。1HNMR(CDCl3、400MHz)は、δ(ppm)1.85(s、6H)、5.17(s、1H)、6.76(s、2H)、6.81〜6.84(m、4H)、6.92〜6.96(m、6H)、7.14(d、J=8.4Hz、2H)、7.45(d、J=8.4Hz、2H)、7.93(s、2H)であり、HRMS(m/z)計算値(C33H25F6IrN2O2)788.1449、実測値788.1451である。
上述のようにして合成する本発明のリン光性Ir錯体を使用して、OLED素子を作製する。それらの素子はすべて、以下の工程に従って製造する。ガラス基材を備える工程は、順次、アノード、正孔注入モディフィケーション層(任意)、正孔輸送層、発光層、正孔阻止層、電子輸送層、正孔注入層(KFフッ化カリウム)(任意)およびカソードを形成する工程である。アノードは、厚み約100nmの電気伝導性ITO(インジウム−スズー酸化物)から作製する。発光層は、ホスト物質の中にリン光性Ir錯体をドーピングして形成する。有機層の蒸着を実施する前に、ITOガラスを清浄するが、それにはまず市販の洗浄剤と有機溶媒で清浄し、その後、UV−オゾンクリーナーを使用する。
素子の製造において、有機材料、リン光性Ir錯体および金属を蒸着する際には、チャンバーの圧力は約5×10-6トルより低く保つ。蒸着速度は、有機材料では約1.5〜2.5オングストローム/秒で、リン光性Ir錯体では約0.05〜0.2オングストローム/秒で、フッ化カリウムでは約0.5オングストローム/秒とする。層の厚みは、正孔注入モディフィケーション層は約10〜15nmで、正孔輸送層は約25〜50nmで、正孔阻止層は約10〜20nmで、電子輸送層は約10〜50nmで、電子注入層(フッ化カリウム)は約0.5nmとする。カソードはMg−Ag合金であるが、蒸着速度はマグネシウムの場合は5オングストローム/秒で、銀の場合は0.5オングストローム/秒とし、マグネシウムと銀は10対1の比率の共蒸発により蒸着して厚み55nmとする。最後に、保護層としての銀を、約100〜150nmの層厚みで蒸着させる。すべての素子(実施例22−実施例47)の主要な特性を表1に示すが、それら素子の構造は、次の通りである。
実施例23は、ITO/NPB(50nm)/I−1:CBP(14.3%、30nm)/TPBI(10nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例25は、ITO/NPB(50nm)/I−1:TPBI(8%、30nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例27:は、ITO/NPB(30nm)/I−2:CCP(5%、30nm)/BCP(10nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例29は、ITO/NPB(50nm)/I−2:CCP(9.7%、30nm)/BCP(10nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例31は、ITO/NPB(50nm)/I−4:CBP(5.7%、30nm)/BCP(10nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例33は、ITO/2−TNATA(10nm)/NPB(40nm)/I−4:CBP(5.7%、30nm)/BCP(10nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例36は、ITO/NPB(50nm)/I−4:CCP(6%、30nm)/BCP(10nm)/Alq(40nm)/Mg:Ag=1O:1である。
実施例38は、ITO/NPB(30nm)/CBP(20nm)/I−4:TPBI(6.7%、30nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例40は、ITO/TCTA(30nm)/I−4:CBP(6.7%、30nm)/BAlq(20nm)/Alq(10nm)/Mg:Ag=10:1である。
実施例42は、ITO/NPB(50nm)/I−5:CBP(6.7%、30nm)/TPBI(10nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例44は、ITO/2−TNATA(10nm)/NPB(40nm)/I−5:CBP(7%、30nm)/BCP(10nm)/Alq(40nm)/Mg:Ag=10:1である。
実施例46は、ITO/NPB(40nm)/I−5:CCP(7%、30nm)/BCP(10nm)/Alq(40nm)/Mg:Ag=10:1である。
Claims (26)
- 基材の上にアノード、前記アノードの上にエレクトロルミネッセント媒体、前記エレクトロルミネッセント媒体の上にカソードを含む有機発光ダイオード(OLED)であって、前記エレクトロルミネッセント媒体が以下の構造(I)または(II)を有するリン光性Ir錯体を含む発光層を含み、
Xは任意のモノアニオン性二座配位子であり、
Zは窒素含有ヘテロサイクリック基を形成可能な任意の原子部分であり、
R1はH、ハロゲン、C1〜C6アルキル、ハロゲン置換したC1〜C6アルキル、C1〜C6アルコキシ、フェニルC1〜C6アルキル、アミノ又はアリールからなる群より選択され、
mは0または前記窒素含有ヘテロサイクリック基の大きさによって決まる1、2、3、または4であり、
R2はH、ハロゲン、C1〜C6アルキル、ハロゲン置換したC1〜C6アルキル、C1〜C6アルコキシ、フェニルC1〜C6アルキル、アミノ、アリールおよびヘテロサイクリックアリールからなる群より選択され、
R3はアリールまたはヘテロサイクリックアリールであり、
前記窒素含有ヘテロサイクリック基はベンゾチアゾールであることを特徴とする有機発光ダイオード(OLED)。
- 前記アリールは、フェニル、ナフチル、ジフェニル、アントリル、ピレニルまたはフェナントリルであり、前記ヘテロサイクリックアリールはベンゾフランまたはチオフェンであることを特徴とする請求項1に記載のOLED。
- R2は、Hまたはメチルであり、R3はアリール基であることを特徴とする請求項1に記載のOLED。
- R3は、フェニルまたはナフチルであることを特徴とする請求項3に記載のOLED。
- 前記リン光性Ir錯体が構造(I)を有し、Xは、アセチルアセトネート、アミノ酸、サリチルアルデヒドまたはイミノアセトネートであることを特徴とする請求項1に記載のOLED。
- Xは、アセチルアセトネートであることを特徴とする請求項5に記載のOLED。
- 前記アノードおよび前記カソードに電圧をかけるときに、前記発光層が黄色から赤色の発光をすることを特徴とする請求項1に記載のOLED。
- 前記発光層は、ホスト化合物をさらに含み、前記Ir錯体が前記ホスト化合物の中にドーピングされることを特徴とする請求項1に記載のOLED。
- 前記ホスト化合物は、正孔輸送能を有する化合物であることを特徴とする請求項9に記載のOLED。
- 前記ホスト化合物は、電子輸送能を有する化合物であることを特徴とする請求項9に記載のOLED。
- 前記エレクトロルミネッセント媒体は、前記アノードと前記発光層との間に正孔輸送層をさらに含むことを特徴とする請求項1に記載のOLED。
- 前記エレクトロルミネッセント媒体は、前記アノードと前記正孔輸送層との間に正孔注入モディフィケーション層をさらに含むことを特徴とする請求項15に記載のOLED。
- 前記エレクトロルミネッセント媒体は、前記カソードと前記発光層との間に正孔阻止層をさらに含み、前記正孔阻止層が前記発光層と接触していることを特徴とする請求項1に記載のOLED。
- 前記エレクトロルミネッセント媒体は、前記正孔阻止層と前記カソードとの間に電子輸送層をさらに含むことを特徴とする請求項19に記載のOLED。
- Xは、アミノ酸またはサリチルアルデヒドであることを特徴とする請求項5に記載のOLED。
- R2は、H、C1〜C6アルキルまたはアリールであり、R3は、アリールであることを特徴とする請求項1に記載のOLED。
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TW092120288A TWI232704B (en) | 2003-07-24 | 2003-07-24 | Organic light emitting diode containing a novel Ir complex as a phosphorescent emitter |
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TWI428053B (zh) * | 2004-02-09 | 2014-02-21 | Idemitsu Kosan Co | Organic electroluminescent element |
US20060134461A1 (en) * | 2004-12-17 | 2006-06-22 | Shouquan Huo | Organometallic materials and electroluminescent devices |
KR100668328B1 (ko) | 2005-02-15 | 2007-01-12 | 삼성전자주식회사 | 양자점 수직공진형 표면방출 레이저 및 그 제조방법 |
TWI313292B (en) * | 2005-11-25 | 2009-08-11 | Chi Mei Optoelectronics Corp | Light-emitting element and iridium complex |
KR100732821B1 (ko) * | 2006-01-11 | 2007-06-27 | 삼성에스디아이 주식회사 | 유기 금속 화합물, 이를 이용한 유기 전계 발광 소자 및그의 제조방법 |
KR100732820B1 (ko) * | 2006-01-11 | 2007-06-27 | 삼성에스디아이 주식회사 | 유기 금속 화합물, 이를 이용한 유기 전계 발광 소자 및그의 제조방법 |
KR100786471B1 (ko) * | 2006-01-11 | 2007-12-17 | 삼성에스디아이 주식회사 | 유기 금속 화합물, 이를 이용한 유기 전계 발광 소자 및그의 제조방법 |
JP4879591B2 (ja) * | 2006-01-26 | 2012-02-22 | 昭和電工株式会社 | 高分子発光材料、有機エレクトロルミネッセンス素子および表示装置 |
CN101473464B (zh) | 2006-06-22 | 2014-04-23 | 出光兴产株式会社 | 应用含有杂环的芳胺衍生物的有机电致发光元件 |
US8062767B2 (en) * | 2007-03-06 | 2011-11-22 | Chien-Hong Cheng | Organic light emitting diode containing a Ir complex having a novel ligand as a phosphorescent emitter |
KR100933226B1 (ko) * | 2007-11-20 | 2009-12-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자 |
KR100933225B1 (ko) * | 2007-11-27 | 2009-12-22 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 인광 화합물 및 이를 발광재료로서 채용하고 있는유기발광소자 |
EP2224510A1 (en) * | 2007-12-21 | 2010-09-01 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
KR100966886B1 (ko) * | 2008-01-29 | 2010-06-30 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자 |
KR100946409B1 (ko) * | 2008-03-19 | 2010-03-09 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 전계 발광 소자 |
JP5382887B2 (ja) | 2009-08-27 | 2014-01-08 | 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 |
US20120211707A1 (en) | 2009-08-27 | 2012-08-23 | National Inst. Of Adv. Ind. Sci. And Tech. | Metal complex composition and complex polymer |
CN101787275B (zh) * | 2010-01-27 | 2013-04-10 | 南京邮电大学 | 含铱配合物的磷光共轭聚合物光电材料的制备和应用方法 |
WO2014044347A1 (de) | 2012-09-20 | 2014-03-27 | Merck Patent Gmbh | Metallkomplexe |
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JP2003253256A (ja) * | 2002-02-27 | 2003-09-10 | Sanyo Electric Co Ltd | 発光素子用発光材料及び有機エレクトロルミネッセント素子 |
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US5432014A (en) * | 1991-11-28 | 1995-07-11 | Sanyo Electric Co., Ltd. | Organic electroluminescent element and a method for producing the same |
US6830828B2 (en) * | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6893743B2 (en) * | 2000-10-04 | 2005-05-17 | Mitsubishi Chemical Corporation | Organic electroluminescent device |
US7118812B2 (en) * | 2003-12-05 | 2006-10-10 | Eastman Kodak Company | Organic element for electroluminescent devices |
US7147937B2 (en) * | 2003-12-05 | 2006-12-12 | Eastman Kodak Company | Organic element for electroluminescent devices |
US7101631B2 (en) * | 2003-12-05 | 2006-09-05 | Eastman Kodak Company | Organic element for electroluminescent devices |
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JP2002234894A (ja) * | 2000-11-29 | 2002-08-23 | Canon Inc | 金属配位化合物、発光素子及び表示装置 |
JP2003253256A (ja) * | 2002-02-27 | 2003-09-10 | Sanyo Electric Co Ltd | 発光素子用発光材料及び有機エレクトロルミネッセント素子 |
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TWI232704B (en) | 2005-05-11 |
JP2005044802A (ja) | 2005-02-17 |
KR100853701B1 (ko) | 2008-08-25 |
US20050227109A1 (en) | 2005-10-13 |
KR20050012132A (ko) | 2005-01-31 |
US7320834B2 (en) | 2008-01-22 |
TW200505279A (en) | 2005-02-01 |
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