JP2017075149A - ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス - Google Patents
ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス Download PDFInfo
- Publication number
- JP2017075149A JP2017075149A JP2016217018A JP2016217018A JP2017075149A JP 2017075149 A JP2017075149 A JP 2017075149A JP 2016217018 A JP2016217018 A JP 2016217018A JP 2016217018 A JP2016217018 A JP 2016217018A JP 2017075149 A JP2017075149 A JP 2017075149A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- layer
- group
- organic
- 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
- -1 iridium carbene complexes Chemical class 0.000 title claims description 42
- 229910052741 iridium Inorganic materials 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 16
- 150000004820 halides Chemical class 0.000 claims abstract description 16
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 150000002825 nitriles Chemical class 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 239000012044 organic layer Substances 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 150000002527 isonitriles Chemical class 0.000 claims description 15
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 15
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 3
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000003446 ligand Substances 0.000 abstract description 26
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract description 24
- 150000002503 iridium Chemical class 0.000 abstract description 3
- 238000006467 substitution reaction Methods 0.000 abstract 2
- 239000010410 layer Substances 0.000 description 105
- 239000000463 material Substances 0.000 description 78
- 229910052751 metal Inorganic materials 0.000 description 25
- 239000002184 metal Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 230000000903 blocking effect Effects 0.000 description 16
- 230000032258 transport Effects 0.000 description 15
- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000007924 injection Substances 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 150000004696 coordination complex Chemical group 0.000 description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 238000000151 deposition Methods 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- 238000003775 Density Functional Theory Methods 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- OLGGLCIDAMICTA-UHFFFAOYSA-N 2-pyridin-2-yl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=N1 OLGGLCIDAMICTA-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- QZLAKPGRUFFNRD-UHFFFAOYSA-N [1]benzoselenolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3[se]C2=C1 QZLAKPGRUFFNRD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 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 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 2
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000010129 solution processing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- FPFAVRAWWGOLSN-UHFFFAOYSA-M 1-methyl-3-phenylimidazol-1-ium;iodide Chemical compound [I-].CN1C=C[N+](C=2C=CC=CC=2)=C1 FPFAVRAWWGOLSN-UHFFFAOYSA-M 0.000 description 1
- 150000005360 2-phenylpyridines Chemical class 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- ACEYZYYNAMWIIE-UHFFFAOYSA-N 4-iododibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(I)=CC=C2 ACEYZYYNAMWIIE-UHFFFAOYSA-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
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000005284 basis set Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- AKYIWGFQFIESOZ-UHFFFAOYSA-N dicyclohexyl-[3-(2,6-dimethoxyphenyl)phenyl]phosphane Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC(P(C2CCCCC2)C2CCCCC2)=C1 AKYIWGFQFIESOZ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 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
- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 1
- RIYPENPUNLHEBK-UHFFFAOYSA-N phenanthro[9,10-b]pyridine Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 RIYPENPUNLHEBK-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000001161 time-correlated single photon counting Methods 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- 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
-
- 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
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
表1 DFT結果
ヘテロレプティック錯体4002のHOMOは、−5.04eVであり、そのトリスCC3では、−5.56eVである。何ら理論に拘束されるものではないが、発光体のHOMOエネルギーが高いほど、発光体がホールを捕捉しやすくなり、その結果、より良好なデバイス効率と寿命が得られると考えられている。
有機発光デバイス中の特定の層に有用として本明細書において記述されている材料は、デバイス中に存在する多種多様な他の材料と組み合わせて使用され得る。例えば、本明細書において開示されている発光性ドーパントは、多種多様なホスト、輸送層、ブロッキング層、注入層、電極、及び存在し得る他の層と併せて使用され得る。以下で記述又は参照される材料は、本明細書において開示されている化合物と組み合わせて有用となり得る材料の非限定的な例であり、当業者であれば、組み合わせて有用となり得る他の材料を特定するための文献を容易に閲覧することができる。
HIL/HTL:
ホスト:
Z1及びZ2は、NR1、O、及びSから選択される。
HBL:
ETL:
110 基板
115 アノード
120 正孔注入層
125 正孔輸送層
130 電子ブロッキング層
135 発光層
140 正孔ブロッキング層
145 電子輸送層
150 電子注入層
155 保護層
160 カソード
162 第一の導電層
164 第二の導電層
170 バリア層
200 反転させたOLED、デバイス
210 基板
215 カソード
220 発光層
225 正孔輸送層
230 アノード
Claims (12)
- 下記の式IIを有するヘテロレプティックイリジウム錯体であることを特徴とする化合物。
R2、及びR5は、モノ、ジ置換又は無置換であることを表し;
Rx、及びR6は、モノ、ジ、トリ、テトラ置換又は無置換であることを表し;
R、R’、R1、R2、Rx、R4、R5、及びR6は、それぞれ独立して、水素、重水素、ハライド、アルキル、シクロアルキル、ヘテロアルキル、アリールアルキル、アルコキシ、アリールオキシ、アミノ、シリル、アルケニル、シクロアルケニル、ヘテロアルケニル、アルキニル、アリール、ヘテロアリール、アシル、カルボニル、カルボン酸、エステル、ニトリル、イソニトリル、スルファニル、スルフィニル、スルフォニル、及びホスフィノからなる群から選択され;
R、R’、R1、Rx、R4、及びR6の2つの隣接する置換基は、互いに結合して、更に置換されていてもよい環を形成してもよく;nは、1又は2である。) - 式IIにおけるnが2である請求項1に記載の化合物。
- 式IIにおけるnが1である請求項1に記載の化合物。
- 式IIにおけるXがOである請求項1に記載の化合物。
- 式IIにおけるXがSである請求項1に記載の化合物。
- 式IIにおけるR1が、アルキル又はシクロアルキルである請求項1に記載の化合物。
- 式IIにおけるR1が、アリール又は置換アリールである請求項1に記載の化合物。
- 式IIにおけるR1が、2,6−二置換アリールである請求項7に記載の化合物。
- 下記からなる群から選択される請求項1に記載の化合物。
(式中、XはO又はSであり;
R1及びR4は、それぞれ独立して、メチル、エチル、プロピル、1−メチルエチル、ブチル、1−メチルプロピル、2−メチルプロピル、ペンチル、1−メチルブチル、2−メチルブチル、3−メチルブチル、1,1−ジメチルプロピル、1,2−ジメチルプロピル、2,2−ジメチルプロピル、シクロペンチル、シクロヘキシル、フェニル、2,6−ジメチルフェニル、2,4,6−トリメチルフェニル、及び2,6−ジイソプロピルフェニル、からなる群から選択され、各基は、部分的に又は完全に重水素化されていてもよい。) - 式IIで表される化合物が下記の式を有する請求項1に記載の化合物。
- R1、R2、及びR4が、メチルである請求項10に記載の化合物。
- 有機発光デバイスを含む第1のデバイスであって、アノードと、カソードと、前記アノードと前記カソードとの間に配置された前記請求項1に記載された式IIで表されるヘテロレプティックイリジウム錯体である化合物を含む有機層とを更に含むことを特徴とする第1のデバイス。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161494667P | 2011-06-08 | 2011-06-08 | |
US61/494,667 | 2011-06-08 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014514571A Division JP2014523410A (ja) | 2011-06-08 | 2012-06-06 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018040841A Division JP6541819B2 (ja) | 2011-06-08 | 2018-03-07 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017075149A true JP2017075149A (ja) | 2017-04-20 |
JP6533204B2 JP6533204B2 (ja) | 2019-06-19 |
Family
ID=46246291
Family Applications (8)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014514601A Pending JP2014517009A (ja) | 2011-06-08 | 2012-06-06 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2014514571A Pending JP2014523410A (ja) | 2011-06-08 | 2012-06-06 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2014514573A Ceased JP2014517007A (ja) | 2011-06-08 | 2012-06-06 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2016217018A Active JP6533204B2 (ja) | 2011-06-08 | 2016-11-07 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2017066584A Active JP6431949B2 (ja) | 2011-06-08 | 2017-03-30 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2017144125A Pending JP2018008976A (ja) | 2011-06-08 | 2017-07-26 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2018040841A Active JP6541819B2 (ja) | 2011-06-08 | 2018-03-07 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2019129834A Active JP6869293B2 (ja) | 2011-06-08 | 2019-07-12 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014514601A Pending JP2014517009A (ja) | 2011-06-08 | 2012-06-06 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2014514571A Pending JP2014523410A (ja) | 2011-06-08 | 2012-06-06 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2014514573A Ceased JP2014517007A (ja) | 2011-06-08 | 2012-06-06 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017066584A Active JP6431949B2 (ja) | 2011-06-08 | 2017-03-30 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2017144125A Pending JP2018008976A (ja) | 2011-06-08 | 2017-07-26 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2018040841A Active JP6541819B2 (ja) | 2011-06-08 | 2018-03-07 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
JP2019129834A Active JP6869293B2 (ja) | 2011-06-08 | 2019-07-12 | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス |
Country Status (7)
Country | Link |
---|---|
US (6) | US9755164B2 (ja) |
EP (3) | EP3178832A1 (ja) |
JP (8) | JP2014517009A (ja) |
KR (8) | KR101933734B1 (ja) |
CN (2) | CN103596967B (ja) |
TW (3) | TWI560189B (ja) |
WO (3) | WO2012170571A1 (ja) |
Families Citing this family (83)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5939984B2 (ja) | 2009-10-28 | 2016-06-29 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ヘテロレプティックなカルベン錯体及び該錯体を有機エレクトロニクスで用いる使用 |
US8883322B2 (en) * | 2011-03-08 | 2014-11-11 | Universal Display Corporation | Pyridyl carbene phosphorescent emitters |
US9755164B2 (en) | 2011-06-08 | 2017-09-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9315724B2 (en) * | 2011-06-14 | 2016-04-19 | Basf Se | Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs |
JP5987281B2 (ja) * | 2011-08-24 | 2016-09-07 | 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及び有機エレクトロルミネッセンス素子の製造方法 |
JP5720505B2 (ja) * | 2011-09-09 | 2015-05-20 | 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、照明装置および表示装置 |
US9773985B2 (en) * | 2012-05-21 | 2017-09-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP2897959B1 (en) | 2012-09-20 | 2017-12-20 | UDC Ireland Limited | Azadibenzofurans for electronic applications |
DE102012020167A1 (de) * | 2012-10-13 | 2014-04-17 | Eberhard Karls Universität Tübingen | Metallkomplexe |
US10439081B2 (en) | 2012-11-06 | 2019-10-08 | Oti Lumionics Inc. | Method for depositing a conductive coating on a surface |
WO2014147134A1 (en) | 2013-03-20 | 2014-09-25 | Basf Se | Azabenzimidazole carbene complexes as efficiency booster in oleds |
JP6048281B2 (ja) * | 2013-03-29 | 2016-12-21 | 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 |
JP6206485B2 (ja) * | 2013-03-29 | 2017-10-04 | 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用金属錯体組成物、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 |
KR20140142000A (ko) * | 2013-06-03 | 2014-12-11 | 제일모직주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
EP3266789B1 (en) | 2013-07-02 | 2019-09-25 | UDC Ireland Limited | Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes |
US20150028290A1 (en) * | 2013-07-25 | 2015-01-29 | Universal Display Corporation | Heteroleptic osmium complex and method of making the same |
US9673408B2 (en) | 2013-07-31 | 2017-06-06 | Udc Ireland Limited | Luminescent diazabenzimidazole carbene metal complexes |
EP3063153B1 (en) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophenes for electronic applications |
US10033000B2 (en) * | 2013-11-15 | 2018-07-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP2874195B1 (en) * | 2013-11-15 | 2017-05-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20160100961A (ko) | 2013-12-20 | 2016-08-24 | 바스프 에스이 | 매우 짧은 감쇠 시간을 갖는 고효율 oled 장치 |
JP6250429B2 (ja) | 2014-02-13 | 2017-12-20 | エスアイアイ・セミコンダクタ株式会社 | 半導体装置およびその製造方法 |
CN115160373A (zh) | 2014-03-31 | 2022-10-11 | Udc 爱尔兰有限责任公司 | 金属络合物和其在有机发光二极管中的用途 |
KR101520278B1 (ko) * | 2014-07-01 | 2015-05-19 | 벽산페인트 주식회사 | 청색 인광 호스트용 화합물 및 이를 포함한 유기 발광 소자 |
WO2016016791A1 (en) | 2014-07-28 | 2016-02-04 | Idemitsu Kosan Co., Ltd (Ikc) | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
US10784448B2 (en) | 2014-08-08 | 2020-09-22 | Udc Ireland Limited | Electroluminescent imidazo-quinoxaline carbene metal complexes |
EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
US10043987B2 (en) * | 2014-09-29 | 2018-08-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
KR102386839B1 (ko) * | 2014-12-22 | 2022-04-15 | 삼성전자주식회사 | 유기 발광 소자 |
KR102385228B1 (ko) | 2014-12-30 | 2022-04-12 | 삼성디스플레이 주식회사 | 유기금속 화합물 및 이를 포함한 유기 발광 소자 |
KR102408143B1 (ko) | 2015-02-05 | 2022-06-15 | 삼성전자주식회사 | 유기금속 화합물, 유기금속 화합물-함유 조성물 및 이를 포함한 유기 발광 소자 |
EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
KR102654860B1 (ko) * | 2015-02-06 | 2024-04-05 | 삼성전자주식회사 | 유기금속 화합물, 유기금속 화합물-함유 조성물 및 이를 포함한 유기 발광 소자 |
US10326086B2 (en) | 2015-02-06 | 2019-06-18 | Samsung Electronics Co., Ltd. | Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound or composition |
EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
US11056657B2 (en) * | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
JP6070758B2 (ja) * | 2015-04-30 | 2017-02-01 | 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 |
EP3304612B1 (en) | 2015-06-03 | 2022-05-04 | UDC Ireland Limited | Highly efficient oled devices with very short decay times |
EP3356369B1 (en) | 2015-10-01 | 2022-05-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
US20180291028A1 (en) | 2015-10-01 | 2018-10-11 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
CN108349987A (zh) | 2015-11-04 | 2018-07-31 | 出光兴产株式会社 | 苯并咪唑稠合杂芳族类 |
WO2017093958A1 (en) | 2015-12-04 | 2017-06-08 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
WO2017100944A1 (en) * | 2015-12-16 | 2017-06-22 | Oti Lumionics Inc. | Barrier coating for opto-electronic devices |
US10968229B2 (en) | 2016-04-12 | 2021-04-06 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
DE102016208298A1 (de) * | 2016-05-13 | 2017-11-16 | Siemens Aktiengesellschaft | Organische elektronenleitende Schicht mit n-Dotierstoff |
US10651403B2 (en) * | 2016-06-20 | 2020-05-12 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10727423B2 (en) | 2016-06-20 | 2020-07-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10686140B2 (en) | 2016-06-20 | 2020-06-16 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN118388374A (zh) * | 2016-12-16 | 2024-07-26 | 株式会社半导体能源研究所 | 有机金属配合物 |
US10745431B2 (en) * | 2017-03-08 | 2020-08-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP6468314B2 (ja) * | 2017-06-15 | 2019-02-13 | 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 |
US12075690B2 (en) * | 2017-12-14 | 2024-08-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11165028B2 (en) * | 2018-03-12 | 2021-11-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11279722B2 (en) | 2018-03-12 | 2022-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN108707168B (zh) * | 2018-04-13 | 2020-06-26 | 苏州科技大学 | 含砜环金属铱配合物及基于该配合物的有机电致发光器件 |
CN108558951B (zh) * | 2018-04-13 | 2020-06-05 | 苏州科技大学 | 含亚砜环金属铱配合物及其在制备有机电致发光器件中的应用 |
CN108586539B (zh) * | 2018-04-13 | 2020-06-05 | 苏州科技大学 | 含二苯并噻吩环金属铱配合物及其作为有机电致发光器件发光层掺杂材料的应用 |
TW202030902A (zh) | 2018-09-12 | 2020-08-16 | 德商麥克專利有限公司 | 電致發光裝置 |
TWI826522B (zh) | 2018-09-12 | 2023-12-21 | 德商麥克專利有限公司 | 電致發光裝置 |
KR20210057092A (ko) | 2018-09-12 | 2021-05-20 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
CN117402190A (zh) | 2019-02-01 | 2024-01-16 | 北京夏禾科技有限公司 | 一种含有氰基取代配体的有机发光材料 |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
JP2022527591A (ja) | 2019-04-11 | 2022-06-02 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機エレクトロルミネッセンス素子のための材料 |
EP4055642B1 (en) | 2019-11-04 | 2024-09-04 | Merck Patent GmbH | Materials for organic electroluminescent devices |
TW202134252A (zh) | 2019-11-12 | 2021-09-16 | 德商麥克專利有限公司 | 有機電致發光裝置用材料 |
TW202136181A (zh) | 2019-12-04 | 2021-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置用的材料 |
US20230139809A1 (en) | 2020-01-29 | 2023-05-04 | Merck Patent Gmbh | Benzimidazole derivatives |
KR20220157456A (ko) | 2020-03-23 | 2022-11-29 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
CN118420679A (zh) | 2020-06-20 | 2024-08-02 | 北京夏禾科技有限公司 | 一种磷光有机金属配合物及其应用 |
CN117343078A (zh) | 2021-11-25 | 2024-01-05 | 北京夏禾科技有限公司 | 有机电致发光材料和器件 |
KR20230174902A (ko) | 2022-06-22 | 2023-12-29 | 대웅바이오(주) | 벤조아민 유도체의 제조방법 |
WO2024105066A1 (en) | 2022-11-17 | 2024-05-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005113704A2 (en) * | 2004-05-18 | 2005-12-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
JP2008147424A (ja) * | 2006-12-11 | 2008-06-26 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP2008521946A (ja) * | 2004-11-25 | 2008-06-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機発光ダイオード(oled)における遷移金属−カルベン錯体の使用 |
JP2009532431A (ja) * | 2006-04-05 | 2009-09-10 | ビーエーエスエフ ソシエタス・ヨーロピア | ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用 |
Family Cites Families (147)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769292A (en) | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
DE69412567T2 (de) | 1993-11-01 | 1999-02-04 | Hodogaya Chemical Co., Ltd., Tokio/Tokyo | Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung |
US5707745A (en) | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
US6939625B2 (en) | 1996-06-25 | 2005-09-06 | Nôrthwestern University | Organic light-emitting diodes and methods for assembly and enhanced charge injection |
US5844363A (en) | 1997-01-23 | 1998-12-01 | The Trustees Of Princeton Univ. | Vacuum deposited, non-polymeric flexible organic light emitting devices |
US6091195A (en) | 1997-02-03 | 2000-07-18 | The Trustees Of Princeton University | Displays having mesa pixel configuration |
US6013982A (en) | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US5834893A (en) | 1996-12-23 | 1998-11-10 | The Trustees Of Princeton University | High efficiency organic light emitting devices with light directing structures |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
US6337102B1 (en) | 1997-11-17 | 2002-01-08 | The Trustees Of Princeton University | Low pressure vapor phase deposition of organic thin films |
US6087196A (en) | 1998-01-30 | 2000-07-11 | The Trustees Of Princeton University | Fabrication of organic semiconductor devices using ink jet printing |
US6528187B1 (en) | 1998-09-08 | 2003-03-04 | Fuji Photo Film Co., Ltd. | Material for luminescence element and luminescence element using the same |
US6830828B2 (en) | 1998-09-14 | 2004-12-14 | The Trustees Of Princeton University | Organometallic complexes as phosphorescent emitters in organic LEDs |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
US6294398B1 (en) | 1999-11-23 | 2001-09-25 | The Trustees Of Princeton University | Method for patterning devices |
US6458475B1 (en) | 1999-11-24 | 2002-10-01 | The Trustee Of Princeton University | Organic light emitting diode having a blue phosphorescent molecule as an emitter |
KR100377321B1 (ko) | 1999-12-31 | 2003-03-26 | 주식회사 엘지화학 | 피-형 반도체 성질을 갖는 유기 화합물을 포함하는 전기소자 |
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 |
JP2002050860A (ja) | 2000-08-04 | 2002-02-15 | Toray Eng Co Ltd | 実装方法および実装装置 |
CN102041001B (zh) | 2000-08-11 | 2014-10-22 | 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 |
US6579630B2 (en) | 2000-12-07 | 2003-06-17 | Canon Kabushiki Kaisha | Deuterated semiconducting organic compounds used for opto-electronic devices |
JP3812730B2 (ja) | 2001-02-01 | 2006-08-23 | 富士写真フイルム株式会社 | 遷移金属錯体及び発光素子 |
JP4307000B2 (ja) | 2001-03-08 | 2009-08-05 | 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 |
JP4310077B2 (ja) | 2001-06-19 | 2009-08-05 | キヤノン株式会社 | 金属配位化合物及び有機発光素子 |
KR100925409B1 (ko) | 2001-06-20 | 2009-11-06 | 쇼와 덴코 가부시키가이샤 | 발광재료 및 유기발광소자 |
US7071615B2 (en) | 2001-08-20 | 2006-07-04 | Universal Display Corporation | Transparent electrodes |
US7250226B2 (en) | 2001-08-31 | 2007-07-31 | Nippon Hoso Kyokai | Phosphorescent compound, a phosphorescent composition and an organic light-emitting device |
US7431968B1 (en) | 2001-09-04 | 2008-10-07 | The Trustees Of Princeton University | Process and apparatus for organic vapor jet deposition |
US6835469B2 (en) | 2001-10-17 | 2004-12-28 | The University Of Southern California | Phosphorescent compounds and devices comprising the same |
US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
US6863997B2 (en) | 2001-12-28 | 2005-03-08 | The Trustees Of Princeton University | White light emitting OLEDs from combined monomer and aggregate emission |
US6723445B2 (en) * | 2001-12-31 | 2004-04-20 | Canon Kabushiki Kaisha | Organic light-emitting devices |
KR100691543B1 (ko) | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
US6878975B2 (en) | 2002-02-08 | 2005-04-12 | Agilent Technologies, Inc. | Polarization field enhanced tunnel structures |
US20030230980A1 (en) | 2002-06-18 | 2003-12-18 | Forrest Stephen R | Very low voltage, high efficiency phosphorescent oled in a p-i-n structure |
US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
EP2264122A3 (en) | 2002-08-27 | 2011-05-11 | Fujifilm Corporation | Organometallic complexes, organic electroluminescent devices and organic electroluminescent displays |
US6687266B1 (en) | 2002-11-08 | 2004-02-03 | Universal Display Corporation | Organic light emitting materials and devices |
JP4365196B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
JP4365199B2 (ja) | 2002-12-27 | 2009-11-18 | 富士フイルム株式会社 | 有機電界発光素子 |
CN101429219B (zh) | 2003-03-24 | 2014-08-06 | 南加利福尼亚大学 | Ir的苯基-吡唑配合物 |
US7090928B2 (en) | 2003-04-01 | 2006-08-15 | The University Of Southern California | Binuclear compounds |
KR101162933B1 (ko) | 2003-04-15 | 2012-07-05 | 메르크 파텐트 게엠베하 | 매트릭스 재료 및 방출 가능 유기 반도체의 혼합물, 그의 용도 및 상기 혼합물을 함유하는 전자 부품 |
US7029765B2 (en) | 2003-04-22 | 2006-04-18 | Universal Display Corporation | Organic light emitting devices having reduced pixel shrinkage |
JP4673744B2 (ja) | 2003-05-29 | 2011-04-20 | 新日鐵化学株式会社 | 有機電界発光素子 |
JP2005011610A (ja) | 2003-06-18 | 2005-01-13 | Nippon Steel Chem Co Ltd | 有機電界発光素子 |
US20050025993A1 (en) | 2003-07-25 | 2005-02-03 | Thompson Mark E. | Materials and structures for enhancing the performance of organic light emitting devices |
TWI390006B (zh) | 2003-08-07 | 2013-03-21 | Nippon Steel Chemical Co | Organic EL materials with aluminum clamps |
DE10338550A1 (de) | 2003-08-19 | 2005-03-31 | Basf Ag | Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs) |
US20060269780A1 (en) | 2003-09-25 | 2006-11-30 | Takayuki Fukumatsu | Organic electroluminescent device |
JP4822687B2 (ja) | 2003-11-21 | 2011-11-24 | 富士フイルム株式会社 | 有機電界発光素子 |
US7332232B2 (en) | 2004-02-03 | 2008-02-19 | Universal Display Corporation | OLEDs utilizing multidentate ligand systems |
EP2918590A1 (en) | 2004-03-11 | 2015-09-16 | Mitsubishi Chemical Corporation | Composition for charge-transport film and ionic compound, charge-transport film and organic electroluminescence device using the same, and production method of the organic electroluminescence device and production method of the charge-transport film |
TW200531592A (en) | 2004-03-15 | 2005-09-16 | Nippon Steel Chemical Co | Organic electroluminescent device |
JP4869565B2 (ja) | 2004-04-23 | 2012-02-08 | 富士フイルム株式会社 | 有機電界発光素子 |
US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
US7598388B2 (en) | 2004-05-18 | 2009-10-06 | The University Of Southern California | Carbene containing metal complexes as OLEDs |
US7154114B2 (en) * | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
US7279704B2 (en) * | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
JP4894513B2 (ja) | 2004-06-17 | 2012-03-14 | 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 |
JP5000496B2 (ja) | 2004-06-28 | 2012-08-15 | チバ ホールディング インコーポレーテッド | トリアゾールとベンゾトリアゾールのエレクトロルミネセンス金属錯体 |
US20060008670A1 (en) | 2004-07-06 | 2006-01-12 | Chun Lin | Organic light emitting materials and devices |
EP1784056B1 (en) | 2004-07-23 | 2011-04-13 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, display and illuminating device |
WO2006067074A1 (en) * | 2004-12-23 | 2006-06-29 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with nucleophilic carbene ligands |
US8362463B2 (en) | 2004-12-30 | 2013-01-29 | E. I. Du Pont De Nemours And Company | Organometallic complexes |
GB2437453B (en) | 2005-02-04 | 2011-05-04 | Konica Minolta Holdings Inc | Material for organic electroluminescence element, organic electroluminescence element, display device and lighting device |
KR100803125B1 (ko) | 2005-03-08 | 2008-02-14 | 엘지전자 주식회사 | 적색 인광 화합물 및 이를 사용한 유기전계발광소자 |
JP5125502B2 (ja) | 2005-03-16 | 2013-01-23 | 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材料、有機エレクトロルミネッセンス素子 |
DE102005014284A1 (de) | 2005-03-24 | 2006-09-28 | Basf Ag | Verwendung von Verbindungen, welche aromatische oder heteroaromatische über Carbonyl-Gruppen enthaltende Gruppen verbundene Ringe enthalten, als Matrixmaterialien in organischen Leuchtdioden |
JPWO2006103874A1 (ja) | 2005-03-29 | 2008-09-04 | 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 |
WO2006114966A1 (ja) | 2005-04-18 | 2006-11-02 | Konica Minolta Holdings, Inc. | 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 |
US7807275B2 (en) | 2005-04-21 | 2010-10-05 | Universal Display Corporation | Non-blocked phosphorescent OLEDs |
US8586204B2 (en) * | 2007-12-28 | 2013-11-19 | Universal Display Corporation | Phosphorescent emitters and host materials with improved stability |
JP4533796B2 (ja) | 2005-05-06 | 2010-09-01 | 富士フイルム株式会社 | 有機電界発光素子 |
US9051344B2 (en) | 2005-05-06 | 2015-06-09 | Universal Display Corporation | Stability OLED materials and devices |
CN101203583A (zh) | 2005-05-31 | 2008-06-18 | 通用显示公司 | 发射磷光的二极管中的苯并[9,10]菲基质 |
KR101010846B1 (ko) | 2005-06-07 | 2011-01-25 | 신닛테츠가가쿠 가부시키가이샤 | 유기 금속착체 및 이것을 이용한 유기 전계 발광소자 |
JP5324217B2 (ja) | 2005-06-27 | 2013-10-23 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 導電性ポリマー組成物 |
JP5076891B2 (ja) | 2005-07-01 | 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 |
JP5017954B2 (ja) * | 2005-08-01 | 2012-09-05 | 三菱化学株式会社 | 遷移金属錯体の製造方法 |
JP2007045742A (ja) * | 2005-08-10 | 2007-02-22 | Mitsubishi Chemicals Corp | 遷移金属錯体の製造方法及び遷移金属錯体 |
JP4935024B2 (ja) * | 2005-08-25 | 2012-05-23 | 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、それを用いた表示装置および照明装置 |
WO2007028417A1 (en) | 2005-09-07 | 2007-03-15 | Technische Universität Braunschweig | Triplett emitter having condensed five-membered rings |
US8148891B2 (en) * | 2005-10-04 | 2012-04-03 | Universal Display Corporation | Electron impeding layer for high efficiency phosphorescent OLEDs |
JP4887731B2 (ja) | 2005-10-26 | 2012-02-29 | 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 |
WO2007063796A1 (ja) | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子 |
WO2007063754A1 (ja) | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子用化合物及び有機電界発光素子 |
US8410280B2 (en) | 2006-01-31 | 2013-04-02 | Basf Se | Process for preparing transition metal-carbene complexes |
EP3569606B1 (en) | 2006-02-10 | 2022-01-05 | Universal Display Corporation | Metal complexes of cyclometallated imidazo (1,2-f)phenanthridine and diimidazo (1,2-a; 1', 2'-c)quinazoline ligands and isoelectronic and benzannulated analogs thereof |
JP4823730B2 (ja) | 2006-03-20 | 2011-11-24 | 新日鐵化学株式会社 | 発光層化合物及び有機電界発光素子 |
US20070247061A1 (en) * | 2006-04-20 | 2007-10-25 | Vadim Adamovich | Multiple dopant emissive layer OLEDs |
EP2639231B1 (en) | 2006-04-26 | 2019-02-06 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative, and organic electroluminescence element using the same |
EP2018090A4 (en) | 2006-05-11 | 2010-12-01 | Idemitsu Kosan Co | ORGANIC ELECTROLUMINESCENCE DEVICE |
US8563145B2 (en) | 2006-06-02 | 2013-10-22 | Idemitsu Kosan Co., Ltd. | Material containing two or three dibenzofuran groups, dibenzothiophene groups, or a combination thereof, which is operable for organic electroluminescence elements, and organic electroluminescence elements using the material |
JP5298460B2 (ja) * | 2006-06-08 | 2013-09-25 | 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 |
US7736756B2 (en) | 2006-07-18 | 2010-06-15 | Global Oled Technology Llc | Light emitting device containing phosphorescent complex |
WO2008023550A1 (fr) | 2006-08-23 | 2008-02-28 | Idemitsu Kosan Co., Ltd. | Dérivé d'amine aromatique et dispositif électroluminescent organique utilisant celui-ci |
JP5589251B2 (ja) | 2006-09-21 | 2014-09-17 | 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 |
US7968146B2 (en) | 2006-11-01 | 2011-06-28 | The Trustees Of Princeton University | Hybrid layers for use in coatings on electronic devices or other articles |
WO2008056746A1 (fr) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
CN103254113A (zh) | 2006-11-24 | 2013-08-21 | 出光兴产株式会社 | 芳香族胺衍生物及使用其的有机电致发光元件 |
JP2008147354A (ja) * | 2006-12-08 | 2008-06-26 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
US8778508B2 (en) | 2006-12-08 | 2014-07-15 | Universal Display Corporation | Light-emitting organometallic complexes |
US8119255B2 (en) | 2006-12-08 | 2012-02-21 | Universal Display Corporation | Cross-linkable iridium complexes and organic light-emitting devices using the same |
WO2008101842A1 (en) | 2007-02-23 | 2008-08-28 | Basf Se | Electroluminescent metal complexes with benzotriazoles |
WO2008132085A1 (de) | 2007-04-26 | 2008-11-06 | Basf Se | Silane enthaltend phenothiazin-s-oxid oder phenothiazin-s,s-dioxid-gruppen und deren verwendung in oleds |
WO2008156879A1 (en) | 2007-06-20 | 2008-12-24 | Universal Display Corporation | Blue phosphorescent imidazophenanthridine materials |
CN101720330B (zh) | 2007-06-22 | 2017-06-09 | Udc爱尔兰有限责任公司 | 发光Cu(I)络合物 |
US8373159B2 (en) | 2007-07-05 | 2013-02-12 | Basf Se | Organic light-emitting diodes comprising carbene-transition metal complex emitter, and at least one compound selected from disilylcarbazoles, disilyldibenzofurans, disilyldibenzothiophenes, disilyldibenzophospholes, disilyldibenzothiophene s-oxides and disilyldibe |
TW200909558A (en) | 2007-07-07 | 2009-03-01 | Idemitsu Kosan Co | Naphthalene derivative, material for organic electroluminescence device, and organic electroluminescence device using the same |
US20090045731A1 (en) | 2007-07-07 | 2009-02-19 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
US8330350B2 (en) | 2007-07-07 | 2012-12-11 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
US8221907B2 (en) | 2007-07-07 | 2012-07-17 | Idemitsu Kosan Co., Ltd. | Chrysene derivative and organic electroluminescent device using the same |
US8779655B2 (en) | 2007-07-07 | 2014-07-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and material for organic electroluminescence device |
TW200903877A (en) | 2007-07-10 | 2009-01-16 | Idemitsu Kosan Co | Material for organic electroluminescence device and organic electroluminescence device utilizing the same |
US8080658B2 (en) | 2007-07-10 | 2011-12-20 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element employing the same |
JP5194596B2 (ja) * | 2007-07-11 | 2013-05-08 | 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 |
KR20100065302A (ko) | 2007-07-27 | 2010-06-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무기 나노입자를 포함하는 전기 전도성 중합체의 수성 분산물 |
TWI511964B (zh) | 2007-08-08 | 2015-12-11 | Universal Display Corp | 苯并稠合噻吩/聯伸三苯混合材料 |
JP2009040728A (ja) | 2007-08-09 | 2009-02-26 | Canon Inc | 有機金属錯体及びこれを用いた有機発光素子 |
JP5194652B2 (ja) | 2007-09-03 | 2013-05-08 | 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 |
KR101741778B1 (ko) | 2007-10-17 | 2017-05-31 | 유디씨 아일랜드 리미티드 | 가교된 카르벤 리간드를 포함하는 전이 금속 착물 및 이의 용도 |
US20090101870A1 (en) | 2007-10-22 | 2009-04-23 | E. I. Du Pont De Nemours And Company | Electron transport bi-layers and devices made with such bi-layers |
US7914908B2 (en) | 2007-11-02 | 2011-03-29 | Global Oled Technology Llc | Organic electroluminescent device having an azatriphenylene derivative |
DE102007053771A1 (de) | 2007-11-12 | 2009-05-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
EP2216313B1 (en) | 2007-11-15 | 2013-02-20 | Idemitsu Kosan Co., Ltd. | Benzochrysene derivative and organic electroluminescent device using the same |
KR101583097B1 (ko) | 2007-11-22 | 2016-01-07 | 이데미쓰 고산 가부시키가이샤 | 유기 el 소자 및 유기 el 재료 함유 용액 |
EP2221896A4 (en) | 2007-11-22 | 2012-04-18 | Idemitsu Kosan Co | ORGANIC EL ELEMENT |
WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
US8221905B2 (en) | 2007-12-28 | 2012-07-17 | Universal Display Corporation | Carbazole-containing materials in phosphorescent light emitting diodes |
JP5709528B2 (ja) | 2008-02-12 | 2015-04-30 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ジベンゾ[f,h]キノキサリンを用いたエレクトロルミネッセンス金属錯体 |
JP2010021336A (ja) * | 2008-07-10 | 2010-01-28 | Konica Minolta Holdings Inc | 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 |
CN102203977B (zh) * | 2008-09-04 | 2014-06-04 | 通用显示公司 | 白色磷光有机发光器件 |
JP5707665B2 (ja) | 2008-12-03 | 2015-04-30 | 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、該素子を備えた照明装置及び表示装置 |
TWI770731B (zh) * | 2009-04-28 | 2022-07-11 | 美商環球展覽公司 | 具有甲基-d3取代之銥錯合物 |
JP5600894B2 (ja) * | 2009-06-24 | 2014-10-08 | コニカミノルタ株式会社 | 白色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 |
JP5939984B2 (ja) * | 2009-10-28 | 2016-06-29 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | ヘテロレプティックなカルベン錯体及び該錯体を有機エレクトロニクスで用いる使用 |
JP5491834B2 (ja) | 2009-12-01 | 2014-05-14 | 川崎重工業株式会社 | エッジグリップ装置、及びそれを備えるロボット。 |
CN102762582B (zh) * | 2009-12-14 | 2015-11-25 | 巴斯夫欧洲公司 | 包含二氮杂苯并咪唑卡宾配体的金属配合物及其在oled中的用途 |
US9304116B2 (en) | 2011-04-25 | 2016-04-05 | Waters Technologies Corporation | Cartridge with multiple electrospray emitters |
US9755164B2 (en) * | 2011-06-08 | 2017-09-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2012
- 2012-06-06 US US14/113,537 patent/US9755164B2/en active Active
- 2012-06-06 JP JP2014514601A patent/JP2014517009A/ja active Pending
- 2012-06-06 KR KR1020137033227A patent/KR101933734B1/ko active Application Filing
- 2012-06-06 CN CN201280027489.0A patent/CN103596967B/zh active Active
- 2012-06-06 KR KR1020187036702A patent/KR102003060B1/ko active IP Right Grant
- 2012-06-06 WO PCT/US2012/041149 patent/WO2012170571A1/en active Application Filing
- 2012-06-06 EP EP17152274.1A patent/EP3178832A1/en not_active Withdrawn
- 2012-06-06 EP EP18209104.1A patent/EP3473634B1/en active Active
- 2012-06-06 WO PCT/US2012/040990 patent/WO2012170461A1/en active Application Filing
- 2012-06-06 KR KR1020197006931A patent/KR20190029768A/ko active Search and Examination
- 2012-06-06 EP EP12727057.7A patent/EP2718302B1/en active Active
- 2012-06-06 KR KR1020137033218A patent/KR20140041551A/ko active Search and Examination
- 2012-06-06 JP JP2014514571A patent/JP2014523410A/ja active Pending
- 2012-06-06 US US14/113,533 patent/US9812656B2/en active Active
- 2012-06-06 KR KR1020137033214A patent/KR101958751B1/ko active IP Right Grant
- 2012-06-06 JP JP2014514573A patent/JP2014517007A/ja not_active Ceased
- 2012-06-06 KR KR1020197006065A patent/KR102166396B1/ko active IP Right Grant
- 2012-06-06 CN CN201611046099.4A patent/CN106588998B/zh active Active
- 2012-06-06 WO PCT/US2012/040993 patent/WO2012170463A1/en active Application Filing
- 2012-06-06 KR KR1020197037463A patent/KR102254061B1/ko active IP Right Grant
- 2012-06-06 US US14/113,530 patent/US9847495B2/en active Active
- 2012-06-06 KR KR1020197020907A patent/KR102119353B1/ko active IP Right Grant
- 2012-06-08 TW TW101120815A patent/TWI560189B/zh active
- 2012-06-08 TW TW101120813A patent/TWI560192B/zh active
- 2012-06-08 TW TW101120814A patent/TWI558714B/zh active
-
2016
- 2016-11-07 JP JP2016217018A patent/JP6533204B2/ja active Active
-
2017
- 2017-03-30 JP JP2017066584A patent/JP6431949B2/ja active Active
- 2017-06-15 US US15/623,491 patent/US10297769B2/en active Active
- 2017-07-26 JP JP2017144125A patent/JP2018008976A/ja active Pending
- 2017-09-28 US US15/718,931 patent/US10978648B2/en active Active
-
2018
- 2018-03-07 JP JP2018040841A patent/JP6541819B2/ja active Active
-
2019
- 2019-03-22 US US16/361,462 patent/US11063229B2/en active Active
- 2019-07-12 JP JP2019129834A patent/JP6869293B2/ja active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005113704A2 (en) * | 2004-05-18 | 2005-12-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
JP2008521946A (ja) * | 2004-11-25 | 2008-06-26 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機発光ダイオード(oled)における遷移金属−カルベン錯体の使用 |
JP2009532431A (ja) * | 2006-04-05 | 2009-09-10 | ビーエーエスエフ ソシエタス・ヨーロピア | ヘテロレプティックな遷移金属−カルベン錯体及びそれを有機発光ダイオード(oled)において用いる使用 |
JP2008147424A (ja) * | 2006-12-11 | 2008-06-26 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6541819B2 (ja) | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス | |
KR102599563B1 (ko) | 유기 전계발광 물질 및 소자 | |
JP6313069B2 (ja) | リン光化合物 | |
JP5982264B2 (ja) | 新規ヘテロレプティックイリジウム錯体 | |
JP6628470B2 (ja) | 有機エレクトロルミネセンス材料、及びデバイス | |
JP5982404B2 (ja) | 電子輸送化合物 | |
JP6427623B2 (ja) | 有機発光材料 | |
KR102051151B1 (ko) | 카르바졸-이미다졸-카르벤 리간드를 함유하는 헤테로렙틱 이리듐 착물 및 발광 디바이스에서의 이의 적용 | |
JP2018070639A (ja) | Oledデバイス用高効率黄色光発光体 | |
JP2015021007A (ja) | カルバゾール含有化合物 | |
JP6473437B2 (ja) | 高効率リン光材料 | |
JP6207273B2 (ja) | ジアリールアミノ置換金属錯体 | |
JP6062741B2 (ja) | 高効率リン光材料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20170817 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170822 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20171013 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20171107 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180307 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20180316 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20180427 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190305 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190405 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190523 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6533204 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |