CN116425798A - Metal complex and application thereof - Google Patents
Metal complex and application thereof Download PDFInfo
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- CN116425798A CN116425798A CN202211486712.XA CN202211486712A CN116425798A CN 116425798 A CN116425798 A CN 116425798A CN 202211486712 A CN202211486712 A CN 202211486712A CN 116425798 A CN116425798 A CN 116425798A
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- Prior art keywords
- metal complex
- layer
- formula
- organic
- organic electroluminescent
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 59
- 239000000463 material Substances 0.000 claims abstract description 54
- 239000010410 layer Substances 0.000 claims description 161
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000002347 injection Methods 0.000 claims description 25
- 239000007924 injection Substances 0.000 claims description 25
- 239000003446 ligand Substances 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 230000005525 hole transport Effects 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052741 iridium Inorganic materials 0.000 claims description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 150000002527 isonitriles Chemical class 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 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 2
- 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 2
- 125000003636 chemical group Chemical group 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 230000008901 benefit Effects 0.000 abstract description 5
- 238000000295 emission spectrum Methods 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 17
- -1 phosphino groups Chemical group 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 230000032258 transport Effects 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 9
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 239000011669 selenium Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000011574 phosphorus Chemical group 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 125000004149 thio group Chemical group *S* 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-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
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Chemical group 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000005401 electroluminescence Methods 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
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 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 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-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
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000012071 phase Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 150000008648 triflates Chemical class 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 1
- HMLURENDJQQGCM-UHFFFAOYSA-N 1-benzothiophene;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2SC=CC2=C1 HMLURENDJQQGCM-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 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 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OCFMSZDCRQQDHU-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.[N] Chemical group C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.[N] OCFMSZDCRQQDHU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- KCQLSIKUOYWBAO-UHFFFAOYSA-N azaborinine Chemical compound B1=NC=CC=C1 KCQLSIKUOYWBAO-UHFFFAOYSA-N 0.000 description 1
- 150000001545 azulenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
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- 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
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- 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
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- 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
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
- H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
- H10K50/131—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit with spacer layers between the electroluminescent layers
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- H—ELECTRICITY
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- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The invention relates to a metal complex, an organic electroluminescent element containing the metal complex and a consumer product, wherein the metal complex can be used as a luminescent material to obtain a green phosphorescent material with high luminous efficiency, and the prepared luminescent material has good thermal stability; the organic electroluminescent element disclosed by the invention emits green phosphorescence and has the advantages of narrow emission spectrum, high stability and high efficiency; by incorporating the organic electroluminescent element of the present invention in an electronic device, a consumer product which emits green light and has improved luminous efficiency can be obtained.
Description
Technical Field
The invention belongs to the technical field of luminescent materials, and particularly relates to a metal complex, an organic electroluminescent element containing the metal complex and a consumer product.
Background
Currently, optoelectronic devices utilizing organic materials are becoming increasingly popular, and many of the materials used to fabricate such devices are relatively inexpensive, so organic optoelectronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) may make them more suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.
OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, lighting and backlighting.
One application of phosphorescent emissive molecules is in full color displays. Industry standards for such displays require pixels adapted to emit a particular color. In particular, these standards require saturated red, green and blue pixels. Alternatively, the OLED may be designed to emit white light. In conventional liquid crystal displays, the emission from a white backlight is filtered using an absorbing filter to produce red, green and blue emissions. The same technique can also be used for OLEDs. The white OLED may be a single light emitting layer (EML) device or a stacked structure. The CIE coordinates, which are well known in the art, can be used to measure color, and the luminescent materials in the prior art have poor luminescence stability and low luminescence efficiency.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a metal complex exhibiting enhanced phosphorescent quantum yield when used in an OLED, particularly in a green emission region, an organic electroluminescent element comprising the same, and a consumer product.
The first object of the present invention is to provide a metal complex which is stable in electroluminescence and high in luminous efficiency.
A second object of the present invention is to provide an organic electroluminescent element made of the metal complex.
A third object of the present invention is to provide a consumer product made of said organic electroluminescent element.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a metal complex comprising a ligand of formula (LA):
wherein X is 1 ～X 8 Each independently selected from N or CR 6 ；
W 1 、W 2 Each independently selected from O, S, se, N, NR 7 、BR 7 、BR 7 R 8 、PR 7 、P(O)R 7 、C＝O、C＝S、C＝Se、C＝NR 7 、C＝CR 7 R 8 、S＝O、SO 2 、C＝R 7 、CR 7 R 8 、SiR 7 R 8 Or GeR 7 R 8 ；
R 1 ～R 8 Each of which is identically or differently selected from hydrogen, deuterium, fluorine, nitrile groups, C 1 ～C 40 Chain alkyl, C 3 ～C 40 Cycloalkyl, C 1 ～C 40 Heteroalkyl, C 3 ～C 40 Heterocycloalkyl, C 6 ～C 60 Aralkyl, C 3 ～C 40 Silane group, C 2 ～C 40 Alkenyl, C 5 ～C 40 Cycloalkenyl, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid, ether, ester, isonitrile, thio, sulfinyl, sulfonyl and phosphino; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring;
R 1 one or two;
the metal complex is formed by coordination of a ligand shown in a formula (LA) and metal M;
the metal complex also comprises other ligands, and the ligand shown in the formula (LA) is connected with the other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand;
the M is selected from one of Os, ir, pd, pt, cu, ag and Au, preferably, the M is selected from one of Ir, pd or Pt.
Further, the formula (LA) includes any one of the following structures:
wherein R is 1 One, two or more to saturation substitution;
the hydrogen in the above formulas may be partially or fully substituted with deuterium or fluorine.
Further, the metal complex has the chemical formula of M (LA) p (LB) q LB is a bidentate ligand, p is 1,2 or 3, q is 0, 1 or 2, and p+q is equal to the oxidation state of the metal M;
wherein LB is selected from one of the following structures:
wherein Y is 1 ～Y 16 Each independently selected from N or CR 17 ，T 1 Selected from BR 18 、NR 18 、PR 18 、O、S、Se、C＝O、S＝O、SO 2 、CR 18 R 19 、SiR 18 R 19 And GeR 18 R 19 One of R 18 And R is 19 Can be optionally joined or fused to form a ring; t (T) 2 Selected from N, B, siR 18 P or p=o;
R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 each independently selected from hydrogen, deuterium, halogen atoms, C 1 ～C 40 Chain alkyl, C 3 ～C 40 Cycloalkyl, C 1 ～C 40 Heteroalkyl, C 3 ～C 40 Heterocycloalkyl, C 6 ～C 60 Aralkyl, C 1 ～C 40 Alkoxy, C 6 ～C 60 Aryloxy, amino, C 3 ～C 40 Silane group, C 2 ～C 40 Alkenyl, C 5 ～C 40 Cycloalkenyl, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl and phosphino groups; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring.
Regarding the oxidation state of the metal M, when M is Ir, the oxidation valence of Ir may be 3, and when M is Pt, the oxidation valence of Pt may be 2.
"halogen", "halogen atom", "halo" in the sense of the present invention are used interchangeably and refer to fluorine, chlorine, bromine or iodine.
"acyl" in the sense of the present invention refers to a substituted carbonyl group (COR).
"esters" in the sense of the present invention mean substituted oxycarbonyl groups (-OCOR or CO) 2 R)。
"Ether" in the sense of the present invention means an-OR group.
"thio" or "thioether" as described herein is used interchangeably and refers to an-SR group.
"sulfinyl" in the sense of the present invention means a-SOR group.
"sulfonyl" in the sense of the present invention means-SO 2 An R group.
"phosphino" in the sense of the present invention means-PR 3 A group, wherein each R may be the same or different.
"silane group" in the sense of the present invention means-SiR 3 A group, wherein each R may be the same or different.
Each of the foregoing R is preferably selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl.
"alkyl", "alkenyl" or "alkynyl" in the sense of the present invention are preferably taken to mean the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
"alkoxy" in the sense of the present invention is preferably an alkoxy group having 1 to 40 carbon atoms, which is understood to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy and 2, 2-trifluoroethoxy.
In general, "cycloalkyl", "cycloalkenyl" according to the present invention refers to and includes monocyclic, polycyclic and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 15 ring carbon atoms, and may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenylCyclohexenyl, cycloheptyl, cycloheptenyl, bicyclo [3.1.1]Heptyl, spiro [4.5 ]]Decyl, spiro [5.5 ]]Undecyl, adamantyl, and the like, wherein one or more of-CH 2 The groups may be replaced by the groups described above; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
"heteroalkyl" or "heterocycloalkyl" in the sense of the present invention means alkyl or cycloalkyl, respectively, preferably having 1 to 40 carbon atoms, meaning hydrogen atom or-CH alone 2 -groups which may be substituted by oxygen, sulphur, halogen atoms, nitrogen, phosphorus, boron, silicon or selenium, preferably groups substituted by oxygen, sulphur or nitrogen. In addition, heteroalkyl or heterocycloalkyl groups may be optionally substituted.
"heteroalkenyl" or "heterocycloalkenyl" in the sense of the present invention means alkenyl or cycloalkenyl in which at least one carbon atom has been replaced with a heteroatom. Optionally, the at least one heteroatom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon or selenium, preferably oxygen, sulfur or nitrogen. Preferred alkenyl and cycloalkenyl groups are those containing from 3 to 15 carbon atoms. In addition, the heteroalkenyl, heterocyclenyl groups may be optionally substituted.
"aralkyl" or "arylalkyl" in the sense of the present invention is used interchangeably and refers to an alkyl group substituted with an aryl group. In addition, aralkyl groups may be optionally substituted.
"aryl" according to the present invention refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycyclic ring may have two or more rings in common in which two carbons are two adjoining rings (the rings being "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. Preferred aryl groups are those containing from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms, more preferably from 6 to 12 carbon atoms. Particularly preferred are aryl groups having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, pa, phenanthrene, fluorene, pyrene, perylene,
And azulenes, preferably phenyl, biphenyl, triphenylene, fluorene and naphthalene. In addition, aryl groups may be optionally substituted.
"heteroaryl" in the sense of the present invention refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems which include at least one heteroatom. Heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, or selenium. In many cases oxygen, sulfur or nitrogen are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring may have one to six heteroatoms. The heteropolycyclic ring system may have two or more rings in which two atoms are common to two adjoining rings (the rings being "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. The heteropolycyclic aromatic ring system may have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, more preferably from three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, diazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene (xanthene), acridine, phenazine, phenothiazine, phenoxazine, benzofurandipyridine, benzothiophene pyridine, thienodipyridine, benzoselenophene dipyridine, dibenzofuran, dibenzoselenium, carbazole, indolocarbazole, benzimidazole, triazine, 1, 2-borazine, 1-boron-nitrogen, 1-nitrogen, 4-boron-nitrogen, boron-nitrogen-like compounds, and the like. In addition, heteroaryl groups may be optionally substituted.
In many cases, the typical substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, and phosphine groups.
As used herein, "combination" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, alkyl and deuterium can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
In one example, the term substitution includes a combination of two to four of the listed groups.
In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms other than hydrogen or deuterium, or combinations comprising up to forty atoms other than hydrogen or deuterium, or combinations comprising up to thirty atoms other than hydrogen or deuterium. In many cases, a preferred combination of substituents will include up to twenty atoms that are not hydrogen or deuterium.
Further, the chemical formula of the metal complex is Ir (LA) (LB) 2 、Ir(LA) 2 (LB)、Ir(LA) 3 Or Pt (LA) (LB), wherein LB is selected from the group consisting of LB 1-LB 432, and the specific structure of LB 1-LB 432 is as follows:
further, M is selected from one of Ir, pd or Pt.
Preferably, M is Ir or Pt.
Further, the formula (LA) includes one of LA1 to LA216, and specific structures of LA1 to LA216 are as follows:
wherein W is 1 Mesh O, S, CD 2 、C(CH 3 ) 2 、C(CD 3 ) 2 Or Si (CH) 3 ) 2 。
Further, the chemical formula of the metal complex is Ir (LAi) (LBj) 2 、Ir(LAi) 2 (LBj) or h (LAi) 3 Wherein i is an integer of 1 to 216, and j is an integer of 1 to 432.
The structures of LA1 to LA216 and LB1 to LB432 are as described above.
The organic electroluminescent material of the present invention comprises one or more of the metal complexes of the present invention. The organic electroluminescent material of the present invention may be formed of only one or more of the metal complexes of the present invention, or may contain other materials than the metal complexes of the present invention.
By incorporating the metal complex of the present invention in the organic electroluminescent material of the present invention, an organic electroluminescent material having a high luminous efficiency in which electroluminescence is green emission can be obtained. In addition, the organic electroluminescent material provided by the invention is an organic electroluminescent material with good thermal stability.
An organic electroluminescent element comprising a first electrode, a second electrode and an organic layer interposed between the first electrode and the second electrode, the organic layer comprising the metal complex.
Further, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a charge generation layer; wherein the light emitting layer comprises one, two, three or more;
preferably, the light-emitting layer includes the metal complex.
Further, the light-emitting layer further comprises a host material, wherein the host material comprises a compound consisting of the following chemical groups: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, nitrogen triphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, and triazine.
Wherein any substituents in the host are non-fused substituents independently selected from the group consisting of: c (C) n H 2n+1 、OC n H 2n+1 、OAr 1 、N(C n H 2n+1 ) 2 、N(Ar 1 )(Ar 2 )、CH＝CH-C n H 2n+1 、C≡CC n H 2n+1 、Ar 1 、Ar 1 -Ar 2 、C n H 2n -Ar 1 Or no substituent, wherein n is an integer from 1 to 40; and wherein Ar is 1 With Ar 2 Independently selected from the group consisting of: benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
In the organic electroluminescent element of the present invention, one of the layers may be a layer containing the metal complex of the present invention, or two or more layers may contain the metal complex of the present invention.
The organic layer may be an emissive layer and the metal complex as described herein may be an emissive dopant or a non-emissive dopant.
A consumer product made from the organic electroluminescent element.
The consumer product described in the present invention may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
Compared with the prior art, the invention has the beneficial effects that:
according to the metal complex, the ligand with the rigid structure shown in the formula (LA) effectively prevents energy loss caused by free rotation between the ligand and metal, and improves quantum efficiency. The material has good thermal stability, the conjugated area is increased, the molecular film forming and exciton transmission performance is improved, the sublimation temperature of the material is reduced, and the material can be used as a luminescent material to obtain a phosphorescent material with high luminous efficiency; by incorporating the organic electroluminescent element of the present invention, an electronic device can obtain a consumer product having a narrow emission spectrum, high stability and high efficiency.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, an electron transport layer 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL) 110. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
Detailed Description
In the organic electroluminescent element of the present invention, the constitution of the layers other than the layer containing the metal complex of the present invention is not limited at all, and the constitution of the other layers of the organic electroluminescent element can be determined by a person skilled in the art as required according to the technical knowledge in the art.
In general, an OLED includes at least one organic layer disposed between and electrically connected to an anode and a cathode. Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, an electron transport layer 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL) 110. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 containing two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED devices have one single color light emitting layer or three light emitting layers of three primary colors, while device 200 has two light emitting layers of the same color. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
The simple layered structure illustrated in fig. 1 and 2 is provided as a non-limiting example, and it should be understood that embodiments of the present invention may be used in conjunction with a wide variety of other structures. The particular materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be implemented by combining the various layers described in different ways based on design, performance, and cost factors, or several layers may be omitted entirely. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it will be understood that combinations of materials may be used, such as mixtures of host and dopant, or more generally, mixtures. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 204 transports holes and injects holes into light emitting layer 205, and may be described as a hole transport layer or an electron blocking layer. In one embodiment, an OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may comprise a single layer or may further comprise multiple layers of different organic materials as described in fig. 1 and 2.
Structures and materials not specifically described, such as PLEDs comprising polymeric materials, may also be used. As another example, an OLED with a single organic layer or multiple stacks may be used. The OLED structure may deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve optical coupling.
Any of the layers of the various embodiments may be deposited by any suitable method unless otherwise specified. For the organic layers, preferred methods include thermal evaporation, organic vapor deposition methods or application of one or more layers by means of carrier gas sublimation, where, at 10- 5 The material is applied at a pressure between mbar and 1 bar. A particular example of this method is the organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured. Other suitable deposition methods include producing one or more layers, for example, by spin coating, or by means of any desired printing method, such as screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing, or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
Devices fabricated according to embodiments of the present invention may further optionally include a capping layer, also known as a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damage due to exposure to harmful substances in the environment, including moisture, vapors and/or gases, etc. The barrier layer may be deposited on the substrate, electrode, under the substrate, electrode, or beside the substrate, electrode, or on any other portion of the device, including the edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by a variety of known chemical vapor deposition techniques and may comprise a composition having a single phase as well as a composition having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic or organic compounds or both. Preferably, the barrier layer comprises a mixture of polymeric and non-polymeric materials. To be considered a mixture, the aforementioned polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same conditions and/or at the same time. The weight ratio of polymeric material to non-polymeric material may be in the range of 95/5 to 5/95. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.
In any of the above mentioned compounds used in each layer of the above mentioned OLED device, the hydrogen atoms may be partially or fully deuterated. Thus, any of the specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, and the like, can be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (e.g., without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be in their non-deuterated, partially deuterated, and fully deuterated forms.
The materials and structures described herein may be applied in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may use the materials and structures. Further, such materials and structures may be used for organic devices such as organic transistors.
These methods are generally known to those of ordinary skill in the art and they can be applied to organic electroluminescent devices comprising the compounds according to the present invention without inventive effort.
According to one embodiment, novel ligands for metal complexes are disclosed. The inventors have found that the introduction of these ligands unexpectedly narrows the emission spectrum, lowers the sublimation temperature, and increases the luminous efficiency of the device.
The method for producing the organic electroluminescent element of the present invention is not limited to the following, and may be variously modified by those skilled in the art based on the common general knowledge in the art. The preparation method comprises the following steps:
and (3) cleaning: cleaning the glass substrate with ITO by using cleaning agents, deionized water, organic solvents and the like;
a step of forming a hole injection layer: forming a hole injection layer containing the metal complex of the present invention on the substrate by vapor deposition of a hole injection layer forming material containing the metal complex of the present invention on the anode layer by vacuum vapor deposition;
a step of forming a hole transport layer: forming a hole transport layer on the hole injection layer by vacuum evaporation;
a step of forming an organic light-emitting layer: forming an organic light-emitting layer containing the metal complex of the present invention on the hole transport layer by vacuum vapor deposition of an organic light-emitting layer forming material containing the material of the present invention on the hole transport layer;
a step of forming an electron transport layer: forming an electron transport layer containing the metal complex of the present invention on the organic light-emitting layer by vacuum evaporation of an electron transport layer forming material containing the metal complex of the present invention on the organic light-emitting layer;
a step of forming a cathode layer: a cathode forming material is vapor deposited, sputtered, or spin coated on the electron transport layer to form a cathode layer.
In the embodiment of the invention, the performance detection conditions of the prepared electroluminescent device are as follows:
luminance and chromaticity coordinates: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: using the NEWPORT 1931-C test;
life test: LTS-1004AC life test apparatus was used.
Example 1
Metal complex: ir (LAi) (LBj) 2 Wherein i is 1 to 216, and a process for the preparation thereofAn integer j is an integer of 1 to 432, comprising the steps of;
the first step: preparation of triflate salt of bis-LBj iridium complex:
10.0mmol of compound LBj and 4.5mmol of IrCl 3 ·3H 2 O is dispersed in 60mL of ethylene glycol diethyl ether and 20mL of water, under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and the filter cake is washed by water and ethanol and dried in vacuum to obtain yellow solid, the obtained yellow solid is dissolved in 100mL of dichloromethane and 10mL of methanol, 5.0mmol of silver triflate is added, the mixture is stirred for 24 hours, the mixture is filtered, and the filtrate is concentrated to dryness under reduced pressure to obtain the triflate of the compound bis-LBj iridium complex.
And a second step of: metal complexes Ir (LAi) (LBj) 2 Is prepared from
4.8mmol of compound LAi and 2.3mmol of triflate of the compound bis-LBj iridium complex prepared in the first step are dispersed in 50mL of ethylene glycol diethyl ether and 50mL of DMF, and the mixture is heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 7 days, cooled to room temperature, concentrated to dryness under reduced pressure, separated and purified by a silica gel column, and eluted by methylene dichloride-normal hexane to obtain a metal complex Ir (LAi) (LBj) 2 The above-mentioned LA1 to LA216 and LB1 to LB432 are the same as defined above.
Reference is made to the above metal complexes: ir (LAi) (LBj) 2 Is prepared by the general preparation method of Ir (LA 3) (LB 105) only as a metal complex 2 Is illustrated in more detail by the preparation examples:
the first step: preparation of Compound Int-1
10.0g of compound LB105 and 9.5g of IrCl 3 ·3H 2 O is dispersed in 150mL of ethylene glycol diethyl ether and 50mL of water, under the protection of nitrogen, the mixture is heated and refluxed for 24 hours, cooled to room temperature, filtered, and filter cakes are washed with water and ethanol and dried in vacuum to obtain 14.8g of yellow solid, the obtained yellow solid is dissolved in 250mL of dichloromethane and 25mL of methanol, 6.5g of silver triflate is added, the mixture is stirred and reacted for 24 hours, the mixture is filtered, and the filtrate is concentrated to dryness under reduced pressure to obtain a compound Int-1, and the yield is: 83%.
And a second step of: ir (LA 3) metal complex (LB 105) 2 Is prepared from
4.8mmol of compound LA3 and 2.3mmol of intermediate Int-1 are dispersed in 50mL of ethylene glycol diethyl ether and 50mL of DMF, and the mixture is heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 7 days, cooled to room temperature, concentrated to dryness under reduced pressure, separated and purified by a silica gel column, and eluted by methylene dichloride-normal hexane to obtain a metal complex Ir (LA 3) (LB 105) 2 ；
W 1 As single bond, yellow solid, yield: 50%, HRMS (MALDI-TOF): m/z=931.2274 [ m+h ]] + 。
W 1 As O, yellow solid, yield: 47%, HRMS (MALDI-TOF): m/z=947.2253 [ m+h ]] + 。
W 1 As S, dark yellow solid, yield: 46%, HRMS (MALDI-TOF): m/z=963.2865 [ m+h ]] + 。
W 1 Is a CD 2 Yellow solid, yield: 44%, HRMS (MALDI-TOF): m/z=947.2577 [ m+h ]] + 。
W 1 Is CMe 2 Yellow solid, yield: 42%, HRMS (MALDI-TOF): m/z=973.3072 [ m+h ]] + 。
Example 2
Metal complex: ir (LAi) 2 (LBj) general preparation method, wherein i is an integer of 1 to 216, j is 1 to 432An integer comprising the steps of;
the first step: preparation of triflate salt of bis-LAi iridium complex:
referring to the synthesis of the first step of example 1, the intermediate compound bis-LAi iridium complex triflate was prepared by substituting only LBj in the first step of example 1 with LAi.
And a second step of: metal complex: ir (LAi) 2 Preparation of (LBj)
Referring to the synthesis method of the second step of example 1, only LAi in the second step of example 1 was replaced with LBj, and the triflate of the compound bis-LBj iridium complex was replaced with the triflate of the compound bis-LAi iridium complex, to prepare and obtain a metal complex Ir (LAi) 2 (LBj)。
The above-mentioned LA1 to LA216 and LB1 to LB432 are the same as defined above.
Reference is made to the above metal complexes: ir (LAi) 2 General preparation of (LBj) Ir (LA 44) alone as a metal complex 2 The preparation of (LB 77) is described in more detail;
ir metal complex (LA 44) 2 Preparation of (LB 77):
the first step: preparation of Compound Int-2
10.0mmol of compound LA44 and 4.5mmol of IrCl 3 ·3H 2 Dispersing O in 60mL of ethylene glycol diethyl ether and 20mL of water, heating and refluxing under nitrogen protection for 24 hours, cooling to room temperature, filtering, washing filter cake with water, ethanol, vacuum drying to obtain yellow solid, and collecting yellow solidThe color solid was dissolved in 50mL of dichloromethane and 5mL of methanol, 20.0mmol of silver triflate was added, and the mixture was stirred and reacted for 24 hours, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain the compound Int-2 as a yellow solid in yield: 76%.
And a second step of: ir metal complex (LA 44) 2 Preparation of (LB 77)
5.5mmol of compound LB77 and 2.5mmol of intermediate Int-2 are dispersed in 15mL of ethylene glycol diethyl ether and 15mL of DMF, and the mixture is stirred and reacted for 7 days under the protection of nitrogen, cooled to room temperature, the reaction solution is poured into 250mL of ice water, extracted by methylene dichloride, the organic phase is collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and separated and purified by a silica gel column, and methylene dichloride-n-hexane is eluted to obtain a metal complex Ir (LA 44) 2 (LB77)；
W 1 As single bond, brown solid, yield: 32%, HRMS (MALDI-TOF): m/z=1072.2635 [ m+h ]] + 。
W 1 As O, brown solid, yield: 38%, HRMS (MALDI-TOF): m/z=1104.2658 [ m+h ]] + 。
W 1 Is a CD 2 Brown solid, yield: 35%, HRMS (MALDI-TOF): m/z=1104.3464 [ m+h ]] + 。
In the above embodiment, W 1 Selected from single bond, O, s, CD 2 、C(CH 3 ) 2 、C(CD 3 ) 2 Or Si (CH) 3 ) 2 。
Example 3
Preparation of an organic electroluminescent element:
(1) Ultrasonic treating the glass substrate coated with the ITO conductive layer in a cleaning agent for 30 minutes, flushing in deionized water, ultrasonic treating in an acetone/ethanol mixed solvent for 30 minutes, baking in a clean environment until the glass substrate is completely dried, irradiating for 10 minutes by an ultraviolet cleaning machine, and bombarding the surface by a low-energy cation beam;
(2) Placing the above ITO glass substrate in a vacuum chamber, and vacuumizing to less than 1×10- 5 Pa, evaporating a metal silver layer as anode layer on the ITO film, and evaporating a film thickness of the film
Continuously evaporating compound HATCN as hole injection layer to obtain an evaporating film with a thickness of +.>
Continuously evaporating HTM as hole transport layer on the hole injection layer film to obtain an evaporating film with a thickness of +.>
(3) Evaporating EBM as electron blocking layer on the hole transport layer to obtain an evaporation film with a thickness of
(4) An organic light-emitting layer is deposited on the electron blocking layer, wherein the light-emitting layer contains H1 as a main body and 3% by mass of the metal complex prepared by the method of the invention is used as a doping material, and the thickness of the deposited film is
(5) Evaporating an electron transport layer of LiQ and ETM as elements on the organic light-emitting layer, wherein LiQ is 50% of ETM by mass, and the film thickness of the evaporated film is
(6) Continuously evaporating a LiF layer on the light-emitting layer to form an electron injection layer of the device, wherein the film thickness of the evaporated film is
(7) Evaporating metal magnesium and silver on the electron injection layer to serve as a cathode layer of the element, wherein the mass ratio of the magnesium to the silver is 1:2, film thickness of vapor depositionIs that
Finally, a CPL layer with NPB as an element is deposited on the transparent cathode, and the thickness of the deposited film is
The OLED element provided by the invention is obtained, and is shown in the attached figure 1.
Example 4
Referring to the preparation method of example 3 described above, an organic light-emitting element of two light-emitting layers or a plurality of light-emitting layers was prepared. As shown in fig. 2, the device 200 includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described using similar materials in example 3.
Comparative example 1
Comparative element 1 was produced by using the compound shown by GD-1 instead of the metal complex of the present invention in step 4 of example 3, and by the same procedure as in example 3.
The structural formulas of HATCN, HTM, EBM, H, liQ, GD-1 and ETM are as follows:
according to the same manner as in example 3, the metal complex Ir (LAi) according to the invention is used 2 (LBj) or Ir (LAi) (LBj) 2 An organic electroluminescent element was fabricated as a doping material for an organic light-emitting layer, and the following performance test was performed:
measurement using digital source meter and luminance meterThe organic electroluminescent elements prepared in examples 3 and 4 and comparative example 1 were driven in voltage and current efficiency and lifetime of the elements. Specifically, the voltage was increased at a rate of 0.1V per second, and it was determined that the current density of the organic electroluminescent element reached 10mA/cm 2 The voltage at the time is the driving voltage, and the brightness at the time is measured; the ratio of brightness to current density is the current efficiency; LT95% life test is as follows: at 1000cd/m using a luminance meter 2 The luminance decay of the organic electroluminescent element was measured to be 950cd/m while maintaining a constant current at luminance 2 Time in hours. Ir (LA 1 to LA 216) (LB 105) was used as the complex 2 For representative example, the data is normalized compared to the comparison element 1.
TABLE 1
As can be seen from table 1, the metal complex of the present invention as a doping material for the light emitting layer has a lower driving voltage than that of the comparative element 1, and the full-width at half maximum (FWHM) of the light emitting peak is narrowed, and particularly has a great advantage in terms of external quantum efficiency and LT95% lifetime.
The compound GD-1 of comparative example 1 is different from the compound of the present invention in that the dibenzofuran plane conjugation ability of the ligand is weak and the steric hindrance of the phenyl group and the nitrile group is small, and the performance of the metal-ligand charge transfer is lowered due to the energy loss caused by the free rotational vibration of the ligand, whereas the metal complex ligand of the present invention forms a rigid structure by introducing the benzofuran of the seven-membered ring, the conjugation plane is enhanced, the steric hindrance is increased, and the rotation of the ligand is blocked, so that the performance thereof in the metal-ligand charge transfer is improved, the driving voltage of the element is lowered, the light emission peak is narrowed, the color purity and the efficiency are improved, and is a luminescent material excellent in performance.
The properties of only a portion of the metal complexes are shown in Table 1 above, and the inventors have conducted the above-described experiments on other metal complexes, and the results are substantially consistent and not listed again because of limited space.
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims. The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (10)
1. A metal complex comprising a ligand of formula (LA):
wherein X is 1 ～X 8 Each independently selected from N or CR 6 ；
W 1 、W 2 Each independently selected from O, S, se, N, NR 7 、BR 7 、BR 7 R 8 、PR 7 、P(O)R 7 、C＝O、C＝S、C＝Se、C＝NR 7 、C＝CR 7 R 8 、S＝O、SO 2 、C＝R 7 、CR 7 R 8 、SiR 7 R 8 Or GeR 7 R 8 ；
R 1 ～R 8 Each of which is identically or differently selected from hydrogen, deuterium, fluorine, nitrile groups, C 1 ～C 40 Chain alkyl, C 3 ～C 40 Cycloalkyl, C 1 ～C 40 Heteroalkyl, C 3 ～C 40 Heterocycloalkyl, C 6 ～C 60 Aralkyl, C 3 ～C 40 Silane group, C 2 ～C 40 Alkenyl, C 5 ～C 40 Cycloalkenyl, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid, ether, ester, isonitrile, thio, sulfinyl, sulfonyl and phosphino; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring;
R 1 one or two;
the metal complex is formed by coordination of a ligand shown in a formula (LA) and metal M;
the metal complex also comprises other ligands, and the ligand shown in the formula (LA) is connected with the other ligands to form a tridentate, tetradentate, pentadentate or hexadentate ligand;
the M is selected from one of Os, ir, pd, pt, cu, ag and Au, preferably, the M is selected from one of Ir, pd or Pt.
2. The metal complex of claim 1, wherein said formula (LA) comprises any one of the following structures:
wherein R is 1 One, two or more to saturation substitution;
the hydrogen in the above formulas may be partially or fully substituted with deuterium or fluorine.
3. The metal complex of claim 1 or 2, wherein the metal complex has the formula M (LA) p (LB) q LB is a bidentate ligand, p is 1,2 or 3, q is 0, 1 or 2, and p+q is equal to the oxidation state of the metal M;
wherein LB is selected from one of the following structures:
wherein Y is 1 ～Y 16 Each independently selected from N or CR 17 ，T 1 Selected from BR 18 、NR 18 、PR 18 、O、S、Se、C＝O、S＝O、SO 2 、CR 18 R 19 、SiR 18 R 19 And GeR 18 R 19 One of R 18 And R is 19 Can be optionally joined or fused to form a ring; t (T) 2 Selected from N, B, siR 18 P or p=o;
R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 each independently selected from hydrogen, deuterium, halogen atoms, C 1 ～C 40 Chain alkyl, C 3 ～C 40 Cycloalkyl, C 1 ～C 40 Heteroalkyl, C 3 ～C 40 Heterocycloalkyl, C 6 ～C 60 Aralkyl, C 1 ～C 40 Alkoxy, C 6 ～C 60 Aryloxy, amino, C 3 ～C 40 Silane group, C 2 ～C 40 Alkenyl, C 5 ～C 40 Cycloalkenyl, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl and phosphino; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or multi-membered ring.
4. A metal complex according to any one of claims 1 to 3, wherein the metal complex has the formula Ir (LA) (LB) 2 、Ir(LA) 2 (LB)、Ir(LA) 3 Or Pt (LA) (LB), wherein LB is selected from the group consisting of LB 1-LB 432, and the specific structure of LB 1-LB 432 is as follows:
5. the metal complex according to any one of claims 1 to 4, wherein the formula (LA) comprises one of LA1 to LA216, and the specific structure of LA1 to LA216 is as follows:
wherein W is 1 Selected from O, S, CD 2 、C(CH 3 ) 2 、C(CD 3 ) 2 Or Si (CH) 3 ) 2 。
6. The metal complex according to claim 4 or 5, wherein the metal complex has a chemical formula of Ir (LAi) (LBj) 2 、Ir(LAi) 2 (LBj) or Ir (LAi) 3 Wherein i is an integer of 1 to 216, and j is an integer of 1 to 432.
7. An organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 6.
8. The organic electroluminescent element according to claim 7, wherein the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a charge generation layer;
wherein the light emitting layer comprises one, two, three or more;
preferably, the light-emitting layer comprises the metal complex according to any one of claims 1 to 6.
9. The organic electroluminescent element according to claim 8, wherein the light-emitting layer further comprises a host material, and the host material comprises a compound composed of the following chemical groups: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, and triazine.
10. A consumer product made from the organic electroluminescent element of claim 8 or 9.
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