JP2020007302A - 有機エレクトロルミネセンス材料及びデバイス - Google Patents
有機エレクトロルミネセンス材料及びデバイス Download PDFInfo
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- JP2020007302A JP2020007302A JP2019118099A JP2019118099A JP2020007302A JP 2020007302 A JP2020007302 A JP 2020007302A JP 2019118099 A JP2019118099 A JP 2019118099A JP 2019118099 A JP2019118099 A JP 2019118099A JP 2020007302 A JP2020007302 A JP 2020007302A
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- 239000000463 material Substances 0.000 title abstract description 89
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 239000003446 ligand Substances 0.000 claims abstract description 92
- 229910052751 metal Inorganic materials 0.000 claims abstract description 26
- 239000002184 metal Substances 0.000 claims abstract description 26
- 238000006467 substitution reaction Methods 0.000 claims abstract description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims abstract description 7
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract description 7
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 7
- -1 amino, silyl Chemical group 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 18
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 150000004696 coordination complex Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical group 0.000 claims description 10
- 150000002527 isonitriles Chemical group 0.000 claims description 10
- 150000002825 nitriles Chemical group 0.000 claims description 10
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- 125000005580 triphenylene group Chemical group 0.000 claims description 10
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 8
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 230000000536 complexating effect Effects 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 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
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000003636 chemical group Chemical group 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 114
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000002019 doping agent Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 230000032258 transport Effects 0.000 description 18
- 230000000903 blocking effect Effects 0.000 description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 125000005842 heteroatom Chemical group 0.000 description 13
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- 229940093475 2-ethoxyethanol Drugs 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 6
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 229960005544 indolocarbazole Drugs 0.000 description 5
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 5
- 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 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 3
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 3
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 3
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 239000012267 brine Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
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Classifications
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- 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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Abstract
Description
本願は、その開示内容の全体を参照によって援用する、2018年7月11日出願の米国特許仮出願第62/696,383号に対する優先権を主張するものである。
下記の式IIの構造に基づくLA1〜LA448
(式中、LAは、LAiからなる群から選択され、式中iは、1〜1792の整数であり;
LBは、LBkからなる群から選択され、式中kは、1〜468の整数であり;
LCは、LCjからなる群から選択され、jは、1〜1260の整数であり;
x=i、y=468+k−468、z=1260i+j−1260であり;
各LBkは、下記の構造を有し;
他の材料との組合せ
伝導性(導電性)ドーパント:
EP01617493、EP01968131、EP2020694、EP2684932、US20050139810、US20070160905、US20090167167、US2010288362、WO06081780、WO2009003455、WO2009008277、WO2009011327、WO2014009310、US2007252140、US2015060804、US20150123047、及びUS2012146012
式中、kは1から20までの整数であり;X101からX108はC(CHを含む)又はNであり;Z101はNAr1、O、又はSであり;Ar1は、上記で定義したものと同じ基を有する。
CN102702075、DE102012005215、EP01624500、EP01698613、EP01806334、EP01930964、EP01972613、EP01997799、EP02011790、EP02055700、EP02055701、EP1725079、EP2085382、EP2660300、EP650955、JP07−073529、JP2005112765、JP2007091719、JP2008021687、JP2014−009196、KR20110088898、KR20130077473、TW201139402、US06517957、US20020158242、US20030162053、US20050123751、US20060182993、US20060240279、US20070145888、US20070181874、US20070278938、US20080014464、US20080091025、US20080106190、US20080124572、US20080145707、US20080220265、US20080233434、US20080303417、US2008107919、US20090115320、US20090167161、US2009066235、US2011007385、US20110163302、US2011240968、US2011278551、US2012205642、US2013241401、US20140117329、US2014183517、US5061569、US5639914、WO05075451、WO07125714、WO08023550、WO08023759、WO2009145016、WO2010061824、WO2011075644、WO2012177006、WO2013018530、WO2013039073、WO2013087142、WO2013118812、WO2013120577、WO2013157367、WO2013175747、WO2014002873、WO2014015935、WO2014015937、WO2014030872、WO2014030921、WO2014034791、WO2014104514、WO2014157018
ホスト:
EP2034538、EP2034538A、EP2757608、JP2007254297、KR20100079458、KR20120088644、KR20120129733、KR20130115564、TW201329200、US20030175553、US20050238919、US20060280965、US20090017330、US20090030202、US20090167162、US20090302743、US20090309488、US20100012931、US20100084966、US20100187984、US2010187984、US2012075273、US2012126221、US2013009543、US2013105787、US2013175519、US2014001446、US20140183503、US20140225088、US2014034914、US7154114、WO2001039234、WO2004093207、WO2005014551、WO2005089025、WO2006072002、WO2006114966、WO2007063754、WO2008056746、WO2009003898、WO2009021126、WO2009063833、WO2009066778、WO2009066779、WO2009086028、WO2010056066、WO2010107244、WO2011081423、WO2011081431、WO2011086863、WO2012128298、WO2012133644、WO2012133649、WO2013024872、WO2013035275、WO2013081315、WO2013191404、WO2014142472、US20170263869、US20160163995、US9466803
CN103694277、CN1696137、EB01238981、EP01239526、EP01961743、EP1239526、EP1244155、EP1642951、EP1647554、EP1841834、EP1841834B、EP2062907、EP2730583、JP2012074444、JP2013110263、JP4478555、KR1020090133652、KR20120032054、KR20130043460、TW201332980、US06699599、US06916554、US20010019782、US20020034656、US20030068526、US20030072964、US20030138657、US20050123788、US20050244673、US2005123791、US2005260449、US20060008670、US20060065890、US20060127696、US20060134459、US20060134462、US20060202194、US20060251923、US20070034863、US20070087321、US20070103060、US20070111026、US20070190359、US20070231600、US2007034863、US2007104979、US2007104980、US2007138437、US2007224450、US2007278936、US20080020237、US20080233410、US20080261076、US20080297033、US200805851、US2008161567、US2008210930、US20090039776、US20090108737、US20090115322、US20090179555、US2009085476、US2009104472、US20100090591、US20100148663、US20100244004、US20100295032、US2010102716、US2010105902、US2010244004、US2010270916、US20110057559、US20110108822、US20110204333、US2011215710、US2011227049、US2011285275、US2012292601、US20130146848、US2013033172、US2013165653、US2013181190、US2013334521、US20140246656、US2014103305、US6303238、US6413656、US6653654、US6670645、US6687266、US6835469、US6921915、US7279704、US7332232、US7378162、US7534505、US7675228、US7728137、US7740957、US7759489、US7951947、US8067099、US8592586、US8871361、WO06081973、WO06121811、WO07018067、WO07108362、WO07115970、WO07115981、WO08035571、WO2002015645、WO2003040257、WO2005019373、WO2006056418、WO2008054584、WO2008078800、WO2008096609、WO2008101842、WO2009000673、WO2009050281、WO2009100991、WO2010028151、WO2010054731、WO2010086089、WO2010118029、WO2011044988、WO2011051404、WO2011107491、WO2012020327、WO2012163471、WO2013094620、WO2013107487、WO2013174471、WO2014007565、WO2014008982、WO2014023377、WO2014024131、WO2014031977、WO2014038456、WO2014112450
ETL:
実験
2−(4−シクロヘキシルナフタレン−2−イル)ピリジンの合成
CC1の合成
(A)トリエチルホスフェート(16mL)中、2−(4−シクロヘキシルナフタレン−2−イル)ピリジン(1.2g、4.2mmol)の溶液を窒素で10分間スパージした。塩化イリジウム(III)水和物(862mg、2.33mmol)を添加し、反応混合物を120℃で25時間撹拌した。冷却した反応混合物をDIUF水(16mL)で希釈し、濾過し、固体をエタノール(3×10mL)で洗浄した。固体を空気乾燥し、オレンジ色の固体として、ジ−μ−クロロ−テトラキス[(2−(4−シクロヘキシルナフチル(cyclohexylnaphth)−1’イル)−ピリジン−1−イル)]ジイリジウム(III)を得た(2.11g、収率>100%)。(B)エタノール(25mL)中、ジ−μ−クロロ−テトラキス[(2−(4−シクロヘキシルナフチル(cyclohexylnaphth)−1’イル)−ピリジン−1−イル)]ジイリジウム(III)(2.11g、1.16mmol)及びアセチルアセトン(630mg、6.3mmol)の懸濁液を窒素で10分間スパージした。粉末状の炭酸カリウム(1.2g、8.4mmol)を添加し、暗所において室温で5時間反応混合物を撹拌した。DIUF水(25mL)を添加し、スラリーを1時間撹拌し、濾過し、水(3×5mL)及びエタノール(3×5mL)で固体を洗浄し、その後空気乾燥した。オレンジ色の固体(約2g)をシリカゲルのカラム(50g)に充填し、1:1ジクロロメタン及びヘキサン(250mL)で溶離した。最も清澄な生成物画分を濃縮し、真空オーブンにおいて50℃で固体を乾燥し、オレンジ色の固体として、化合物CC1、ビス[(2−(4−シクロヘキシルナフチル−1’−イル)−ピリジン−1−イル)]−(2,4−ペンタンジオナト(pen−tanedionato)−k2O,O’)イリジウム(III)を得た(0.81mg、収率40%)。
2−(4−シクロヘキシルナフタレン−2−イル)−4−メチルピリジンの合成
CC2の合成
2−(4−シクロヘキシルナフタレン−2−イル)−4−(トリフルオロメチル)ピリジンの合成
CC3の合成
4−(tert−ブチル)−2−(4−シクロヘキシルナフタレン−2−イル)ピリジンの合成
CC4の合成
2−(4−シクロヘキシル−ナフタレン−2−イル)−4−(3,3,3−トリフルオロ−2,2−ジメチルプロピル)ピリジンの合成
化合物C88,222の合成
(D)2−エトキシエタノール(100mL)中、ジ−μ−クロロ−テトラキス[(4−(4−シクロヘキシルナフタレン−2−イル)−4−(3,3,3−トリ−フルオロ−2,2−ジメチルプロピル)ピリジン−2−イル]ジイリジウム(III)(4.08g、3.9mmol)、及びペンタン−2,4−ジオン(0.78g、7.8mmol)の溶液を窒素で5分間スパージした。粉末状の炭酸カリウム(1.08g、7.8mmol)を添加し、スパージングを更に5分間続けた。混合物を50℃で24時間撹拌した。DIUF水(100mL)を添加し、懸濁液を30分間撹拌し、濾過し、僅かに粘性の固体を水(30mL)で洗浄した。固体をメタノール(50mL)中で10分間スラリー化し、濾過し、固体をメタノール(50mL)で洗浄した。ヘキサン(20mL)中30%ジクロロメタンに、赤色固体を溶解/懸濁し、35℃で30分間撹拌した。スラリーをシリカゲルのカラムに直接充填し、ヘキサン中30〜40%ジクロロメタンで溶離した。画分を含む生成物を減圧下で濃縮し、真空オーブンにおいて50℃で乾燥し、赤色固体として、化合物C88,222、[(2−(4−シクロヘキシル−ナフタレン−2−イル)−4−(3,3,3−トリ−フルオロ−2,2−ジメチルプロピル)ピリジン−2−イル]−(2,4−ペンタンジオナト−k2O,O’)イリジウム(III)を得た(1.8g、2ステップにおいて収率36%)。
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1の導電層
164 第2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 (15)
- 下記の式Iの配位子LAを含むことを特徴とする化合物。
RA、RB、及びRCは、それぞれ独立して、モノから置換の最大許容数を表す、又は無置換を表し;
RA、RB、及びRCは、それぞれ独立して、水素である、又は重水素、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、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、カルボン酸、エーテル、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、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
少なくとも1つのRAは、式−CH2R又は−CHRR’を有し;
R及びR’は、それぞれ独立して、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、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、アリール、ヘテロアリール、及びこれらの組合せからなる群から選択され;
LAは、金属Mと錯体化し;
Mは、任意に他の配位子と配位され;
前記配位子LAは、任意に他の配位子と連結され、三座配位子、四座配位子、五座配位子、又は六座配位子を含み;
RB及びRCの任意の2つの置換基は、共に結合又は縮合し、環を形成してもよい。) - Mが、Os、Ir、Pd、Pt、Cu、及びAuからなる群から選択される請求項1に記載の化合物。
- Rが、アルキル、シクロアルキル、それらの部分的にフッ素化したバリアント(variant)、それらの部分的又は完全に重水素化したバリアント、及びそれらの組合せからなる群から選択される請求項1に記載の化合物。
- 少なくとも1つのRBが、シクロヘキシル基又はtert−ブチル基を含む請求項1に記載の化合物。
- 環Cが、フラン環又はチオフラン環である;又は環Cが、ベンゼン、ピリジン、ピリミジン、ピラジン、及びピリダジンからなる群から選択される請求項1に記載の化合物。
- 前記配位子LAが、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。
- 前記配位子LAが、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。
下記の式IIの構造に基づくLA1〜LA448
- 前記化合物が、M(LA)x(LB)y(LC)zの式を有し、LB及びLCは、それぞれ二座配位子であり;xは、1、2、又は3であり;yは、0、1、又は2であり;zは、0、1、又は2であり;x+y+zは、前記金属Mの酸化状態である請求項1に記載の化合物。
- 前記化合物が、Ir(LA)3、Ir(LA)(LB)2、Ir(LA)2(LB)、Ir(LA)2(LC)、及びIr(LA)(LB)(LC)からなる群から選択される式を有し、LA、LB、及びLCは、互いに異なる;又は前記化合物が、Pt(LA)(LB)の式を有し、LA及びLBは、同じでも異なっていることもできる請求項8に記載の化合物。
- LB及びLCが、それぞれ独立して、下記からなる群から選択される請求項8に記載の化合物。
Y’は、BRe、NRe、PRe、O、S、Se、C=O、S=O、SO2、CReRf、SiReRf、及びGeReRfからなる群から選択され;
Re及びRfは、任意に縮合又は結合して環を形成し;
Ra、Rb、Rc、及びRdは、それぞれ独立して、モノ置換から置換の最大可能数を表してもよい、又は無置換を表してもよく;
Ra、Rb、Rc、Rd、Re、及びRfは、それぞれ独立して、水素である、又は重水素、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、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、カルボン酸、エーテル、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、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
Ra、Rb、Rc、及びRdの任意の2つの隣接する置換基は、任意に縮合又は結合し、環を形成する又は多座配位子を形成する。) - 前記化合物が、式Ir(LA)3を有する化合物Ax、式Ir(LA)(LB)2を有する化合物By、又は式Ir(LA)2(LC)を有する化合物Czである請求項7に記載の化合物。
(式中、LAは、LAiからなる群から選択され、式中iは、1〜1792の整数であり;
LBは、LBkからなる群から選択され、式中kは、1〜468の整数であり;
LCは、LCjからなる群から選択され、jは、1〜1260の整数であり;
x=i、y=468+k−468、z=1260i+j−1260であり;
各LBkは、下記の構造を有し;
- 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、下記の式Iの配位子LAを含む化合物を含む有機層とを含むことを特徴とする有機発光デバイス(OLED)。
RA、RB、及びRCは、それぞれ独立して、モノから置換の最大許容数を表す、又は無置換を表し;
RA、RB、及びRCは、それぞれ独立して、水素である、又は重水素、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、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、カルボン酸、エーテル、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、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
少なくとも1つのRAは、式−CH2R又は−CHRR’を有し;
R及びR’は、それぞれ独立して、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、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、アリール、ヘテロアリール、及びこれらの組合せからなる群から選択され;
LAは、金属Mと錯体化し;
Mは、任意に他の配位子と配位され;
前記配位子LAは、任意に他の配位子と連結され、三座配位子、四座配位子、五座配位子、又は六座配位子を含み;
RB及びRCの任意の2つの置換基は、共に結合又は縮合し、環を形成してもよい。) - 前記有機層がホストを更に含み、前記ホストが、金属錯体、トリフェニレン、カルバゾール、ジベンゾチオフェン、ジベンゾフラン、ジベンゾセレノフェン、アザトリフェニレン、アザカルバゾール、アザ−ジベンゾチオフェン、アザ−ジベンゾフラン、及びアザ−ジベンゾセレノフェンからなる群から選択される少なくとも1つの化学基を更に含む請求項12に記載のOLED。
- 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、下記の式Iの配位子LAを含む化合物を含む有機層とを含む有機発光デバイス(OLED)を含むことを特徴とする消費者製品。
RA、RB、及びRCは、それぞれ独立して、モノから置換の最大許容数を表す、又は無置換を表し;
RA、RB、及びRCは、それぞれ独立して、水素である、又は重水素、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、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、カルボン酸、エーテル、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、スルホニル、ホスフィノ、及びこれらの組合せからなる群から選択される置換基であり;
少なくとも1つのRAは、式−CH2R又は−CHRR’を有し;
R及びR’は、それぞれ独立して、ハロゲン、アルキル、シクロアルキル、ヘテロアルキル、ヘテロシクロアルキル、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、アリール、ヘテロアリール、及びこれらの組合せからなる群から選択され;
LAは、金属Mと錯体化し;
Mは、任意に他の配位子と配位され;
前記配位子LAは、任意に他の配位子と連結され、三座配位子、四座配位子、五座配位子、又は六座配位子を含み;
RB及びRCの任意の2つの置換基は、共に結合又は縮合し、環を形成してもよい。) - 請求項1に記載の化合物を含むことを特徴とする配合物。
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US20240025934A1 (en) | 2024-01-25 |
US11753425B2 (en) | 2023-09-12 |
CN110713498A (zh) | 2020-01-21 |
US20200017536A1 (en) | 2020-01-16 |
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