CN114957342A - Metal complex, organic electroluminescent element and consumer product - Google Patents
Metal complex, organic electroluminescent element and consumer product Download PDFInfo
- Publication number
- CN114957342A CN114957342A CN202210807924.7A CN202210807924A CN114957342A CN 114957342 A CN114957342 A CN 114957342A CN 202210807924 A CN202210807924 A CN 202210807924A CN 114957342 A CN114957342 A CN 114957342A
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- China
- Prior art keywords
- group
- metal complex
- radical
- hydrogen
- deuterium
- Prior art date
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 53
- -1 alkyl radical Chemical class 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- 239000003446 ligand Substances 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 150000002825 nitriles Chemical class 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 150000003254 radicals Chemical group 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 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
- 125000004354 sulfur functional group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 44
- 238000000295 emission spectrum Methods 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 124
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000000151 deposition Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 230000032258 transport Effects 0.000 description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
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- 239000007787 solid Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 230000000052 comparative effect Effects 0.000 description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Chemical group 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- 125000005580 triphenylene group Chemical group 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
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- 125000000592 heterocycloalkyl group Chemical group 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
- 239000012074 organic phase Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011574 phosphorus Chemical group 0.000 description 3
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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
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- 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
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
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- 230000008021 deposition Effects 0.000 description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 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
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
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- 238000004519 manufacturing process Methods 0.000 description 2
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- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 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
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000009210 therapy by ultrasound 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- HWIATMHDQVGMFQ-UHFFFAOYSA-N 1,3-azaborinine Chemical class B1=CC=CN=C1 HWIATMHDQVGMFQ-UHFFFAOYSA-N 0.000 description 1
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- OBUDOIAYABJUHQ-UHFFFAOYSA-N 1,4-azaborinine Chemical class B1=CC=NC=C1 OBUDOIAYABJUHQ-UHFFFAOYSA-N 0.000 description 1
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- HCZVRRQDPKTLAK-UHFFFAOYSA-N 1-nitrotriphenylene Chemical group C1=CC=CC2=C3C([N+](=O)[O-])=CC=CC3=C(C=CC=C3)C3=C21 HCZVRRQDPKTLAK-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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-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
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 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
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 1
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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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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Abstract
The invention relates to a metal complex, an organic electroluminescent element and a consumer product, the metal complex is used as a luminescent material to obtain a phosphorescent material with high luminescent efficiency, the thermal stability of the prepared luminescent material is good, and the organic electroluminescent element prepared by the invention emits green to red phosphorescence and has the advantages of narrow emission spectrum, high stability and high efficiency; the electronic device of the present invention can provide a consumer product with improved electroluminescent efficiency by including the organic electroluminescent element of the present invention.
Description
Technical Field
The invention belongs to the technical field of luminescent materials, and particularly relates to a metal complex, an organic electroluminescent element 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 particular 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 may 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 applications such as flat panel displays, lighting and backlighting.
One application of phosphorescent emissive molecules is 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, OLEDs can be designed to emit white light. In conventional liquid crystal displays, an absorptive filter is used to filter the emission from a white backlight 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 color can be measured using CIE coordinates well known in the art, and the luminescent material in the prior art has poor luminous stability and low luminous efficiency.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a metal complex, an organic electroluminescent device and a consumer product, which exhibit enhanced phosphorescence quantum yield when used in an OLED, particularly in green to red emission regions.
The first purpose of the invention is to provide a metal complex which has stable electroluminescence and high luminous efficiency.
In a second object of the present invention, there is provided an organic electroluminescent element made of the metal complex.
According to a third aspect of the present invention, there is provided a consumer product made from the organic electroluminescent device.
In order to achieve the purpose, the invention adopts the following technical scheme:
a metal complex comprising a ligand LA of formula I, formula I having the structure:
wherein, X 1 ～X 3 Each independently selected from N or CR 2 ；W 1 ～W 4 Each independently selected from N or CR 3 Or two arbitrary adjacent W 1 And W 2 、W 2 And W 3 Or W 3 And W 4 Represents a group represented by the following formula (II) or formula (III) or a combination thereof;
each X independently represents CR 4 Or N, and two of the vicinities ^ refer to the vicinal radicals W in the formula (I) 1 And W 2 、W 2 And W 3 Or W 3 And W 4 ；
Ring B is a five-membered carbocyclic ring, five-membered heterocyclic ring, six-membered carbocyclic ring, six-membered heterocyclic ring, seven-membered carbocyclic ring or seven-membered heterocyclic ring;
T 1 selected from O, S, Se, NR ', BR ', SiR ' R ", CR ' R", or GeR ' R ";
R 1 、R 2 、R 3 、R 4 r ', R' are, on each occurrence, identically or differently selected from hydrogen, deuterium, a halogen atom, C 1 ～C 40 Chain alkyl radical, C 3 ～C 40 Cycloalkyl radical, C 1 ～C 40 Heteroalkyl group, C 3 ～C 40 Heterocycloalkyl radical, C 6 ～C 60 Aralkyl radical, C 1 ～C 4 0 alkoxy group, C 6 ～C 60 Aryloxy, amino, C 3 ～C 40 Silane radical, C 2 ～C 40 Alkenyl radical, C 5 ～C 40 Cycloalkenyl radical, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl radical, C 2 ～C 60 Heteroaryl, C 1 ～C 40 Acyl, carboxylic acid group, ether, ester group, nitrile group, isonitrile group, sulfur group, sulfinyl group, sulfonyl group and phosphine group; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or polycyclic ring;
the ligand LA is coordinated through a metal M to form a five-membered chelate ring;
wherein the ligand LA may be linked to 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, and preferably, the M is selected from one of Ir, Pd or Pt.
Further, the ligand LA is selected from the group consisting of:
wherein, T 2 Selected from O, S, NR 'or SiR' R "; x 1 、X 2 、X 3 Each independently is N or CR 2 ；
R 1 ～R 12 R ', R' are, on each occurrence, identically or differently selected from hydrogen, deuterium, a halogen atom, C 1 ～C 40 Alkyl radical, C 3 ～C 40 Cycloalkyl radical, C 1 ～C 40 Heteroalkyl group, C 3 ～C 40 Heterocycloalkyl radical, C 3 ～C 40 Silyl radical, C 6 ～C 60 Aryl radical, C 2 ～C 60 Heteroaryl, nitrile; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or polycyclic ring.
Further, said R 1 ～R 12 R ', R' are each independently selected, at each occurrence, from hydrogen, deuterium, fluorine, nitrile, R A1 ～R A55 、R B1 ～R B45 、R C1 ～R C295 A group of compounds;
wherein R is A1 ～R A55 The structural formula is as follows:
R B1 ～R B45 the structural formula is as follows：
R C1 ～R C295 The structural formula is as follows:
further, the metal complex has the formula Ir (LA) (LB) 2 、Ir(LA) 2 (LB)、Ir(LA) 3 、Ir(LA) 2 (LC) or Ir (LA) (LB) (LC), wherein LA, LB, and LC are different from each other; or said goldThe metal complex has the formula Pt (LA) (LB), wherein LA and LB may be the same or different.
According to an embodiment of the invention, the LB is selected from the group consisting of the following structures:
according to an embodiment of the invention, the LC is:
wherein, Y 1 ～Y 14 At each occurrence, each is independently selected from N or CR; t is 1 Each independently selected from BR 3 、NR 4 、PR 5 、O、S、Se、C＝O、S＝O、SO 2 、CR 3 R 4 、SiR 3 R 4 And GeR 3 R 4 One of (1); r is 3 And R 4 May be optionally joined or fused to form a ring;
T 2 selected from N, B, SiR, P or P ═ O;
v is selected from B, Al, Ga or In;
each R, R a 、R b 、R c 、R d 、R e 、R f 、R 3 、R 4 、R 5 Each independently selected from hydrogen, deuterium, a halogen atom, C 1 ～C 40 Chain alkyl radical, C 3 ～C 40 Cycloalkyl radical, C 1 ～C 40 Heteroalkyl group, C 3 ～C 40 Heterocycloalkyl radical, C 3 ～C 40 Silyl radical, C 6 ～C 60 Aryl radical, C 2 ～C 60 Heteroaryl, nitrile; and any two or more adjacent substituents are optionally joined or fused together to form a substituentSubstituted or unsubstituted five, six or more membered rings.
Regarding the oxidation state of the metal M, when M is Ir, the oxidation state of Ir may be 3, and when M is Pt, the oxidation state 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 means a substituted carbonyl group (cOR).
"ester" in the sense of the present invention means a substituted oxycarbonyl group (-OCOR or CO) 2 R)。
"Ether" in the sense of the present invention means an-OR group.
The "thio" or "thioether" groups described herein are used interchangeably and refer to the-SR group.
"sulfinyl" in the sense of the present invention means the-SOR group.
"Sulfonyl" in the sense of the present invention means-SO 2 And R group.
"Phosphino" in the sense of the present invention means-PR 3 Groups, wherein each R may be the same or different.
"silyl" in the sense of the present invention means-SiR 3 Groups, wherein each R may be the same or different.
Each of the above R, preferably is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl.
"alkyl", "alkenyl" or "alkynyl" in the sense of the present invention is preferably to be understood as meaning 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, preferably alkoxy having 1 to 40 carbon atoms, is taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexoxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy and 2, 2, 2-trifluoroethoxy.
In general, "cycloalkyl", "cycloalkenyl" according to the invention refers to and includes monocyclic, polycyclic and spiroalkyl groups. Preferred cycloalkyl groups are those containing from 3 to 15 ring carbon atoms and may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, bicyclo [3.1.1]Heptyl, spiro [4.5 ]]Decyl, spiro [5.5 ]]Undecyl, adamantyl, and the like, wherein one or more-CH 2 The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also 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 alkyl or cycloalkyl having 1 to 40 carbon atoms, meaning hydrogen or-CH, respectively 2 Groups which may be substituted by oxygen, sulfur, halogen atoms, nitrogen, phosphorus, boron, silicon or selenium, preferably groups substituted by oxygen, sulfur or nitrogen. In addition, heteroalkyl or heterocycloalkyl groups may be optionally substituted.
"heteroalkenyl" or "heterocycloalkenyl" in the sense of the present invention refers to an alkenyl or cycloalkenyl group wherein at least one carbon atom is replaced by a heteroatom. Optionally, the at least one heteroatom is selected from oxygen, sulphur, nitrogen, phosphorus, boron, silicon or selenium, preferably oxygen, sulphur or nitrogen. Preferred alkenyl, cycloalkenyl groups are those containing from 3 to 15 carbon atoms. In addition, heteroalkenyl, heterocycloalkenyl may be optionally substituted.
"aralkyl" or "arylalkyl" in the sense of the present invention are used interchangeably and refer to an alkyl group substituted with an aryl group. In addition, the aralkyl group may be optionally substituted.
"aryl" according to the invention means and includes monocyclic ringsAromatic hydrocarbon groups and polycyclic aromatic ring systems. Polycyclic rings can have two or more rings in which two carbons are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocycles, and/or heteroaryls. Preferred aryl groups are those containing 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, and more preferably 6 to 12 carbon atoms. Especially preferred are aryl groups having six carbons, ten carbons, or twelve carbons. Suitable aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, opa, phenanthrene, fluorene, pyrene, perylene,
And azulenes, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted.
"heteroaryl" in the sense of the present invention means and includes monocyclic aromatic groups and polycyclic aromatic ring systems comprising 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. Monocyclic heteroaromatic systems are preferably monocyclic with 5 or 6 ring atoms, and rings may have one to six heteroatoms. A heteropolycyclic system can have two or more rings in which two atoms are common to two adjoining rings (the rings are "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocycles and/or heteroaryls. The heterocyclic aromatic ring system may have one to six heteroatoms per 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, pyrrolobipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothienopyridine, and selenenopyridine, preferably dibenzothiophene, and benzothiophene, Dibenzofurans, dibenzoselenophenes, carbazoles, indolocarbazoles, imidazoles, pyridines, triazines, benzimidazoles, 1, 2-azaborines, 1, 3-azaborines, 1, 4-azaborines, borazines, and aza analogs thereof. In addition, the heteroaryl group may be optionally substituted.
In many cases, the substituent is 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 phosphino.
As used herein, "a combination thereof" 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 envision from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl; halogen and alkyl groups may be combined to form haloalkyl substituents, such as trifluoromethyl and the like; and halogen, alkyl, and aryl groups may be combined to form haloaralkyl groups.
In one example, the term substituted includes combinations 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 those containing up to fifty atoms other than hydrogen or deuterium, or those containing up to forty atoms other than hydrogen or deuterium, or those containing 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 LB is selected from a group consisting of LB 1-LB 432, and the particular structures of LB 1-LB 432 are as follows:
further, the LC is selected from a group consisting of structures shown by LC 1-LC 44, and specific structures of LC 1-LC 44 are shown as follows:
further, the ligand LA comprises one of LA 1-LA 436, and LA 1-LA 436 have the following specific structures:
wherein R is 1 、R 2 、R 3 、R 4 At each occurrence, each is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, R A1 ～R A55 、R B1 ～R B45 、R C1 ～R C295 A group of compounds;
R 5 、R 6 、R 7 、R 8 、R 9 、R 10 at each occurrence, each is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, R A1 ～R A55 、R B1 ～R B45 A group of combinations thereof.
According to an embodiment of the invention, said R 1 、R 2 、R 3 、R 4 At each occurrence, each is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, R A1 ～R A3 、R B1 ～R B7 、R C1 ～R C140 A group of combinations thereof.
According to an embodiment of the invention, said R 5 、R 6 、R 7 、R 8 、R 9 、R 10 Each occurrence is independently selected from hydrogen, deuterium, fluorine, nitrile, R A1 ～R A3 、R B1 ～R B7 A group of combinations thereof.
According to an embodiment of the invention, the metal complex is Ir (LAi) or (LBj) 2 、Ir(LAi) 2 (LBj)、Ir(LAi) 3 、Ir(LAi) 2 (LCn) or Ir (LAi) (LBj) (LCn), wherein i is an integer of 1-436, j is an integer of 1-432, and n is an integer of 1-44; the LA 1-LA 436 are the structures preferably shown above; the LB 1-LB 432 and LC 1-LC 44 are the preferred structures.
The organic electroluminescent material of the present invention includes 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.
When the organic electroluminescent material of the present invention contains the metal complex of the present invention, an organic electroluminescent material having high electroluminescent efficiency can be obtained. In addition, the organic electroluminescent material of the present invention is an organic electroluminescent material having 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 further comprises a host material, and the host material comprises the following chemical groups: triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, nitrotriphenylene, azacarbazole, azadibenzothiophene, azadibenzofuran, and azadibenzoselenophene.
Wherein any substituent in the host is each independently selected from the group consisting of non-fused substituents consisting of: c m H 2m+1 、OC m H 2m+1 、OAr 1 、N(C m H 2m+1 ) 2 、N(Ar 1 )(Ar 2 )、CH＝CH-C m H 2m+1 、C≡CC m H 2m+1 、Ar 1 、Ar 1 -Ar 2 、C m H 2m -Ar 1 Or no substituent, wherein m is an integer of 1-10; and wherein Ar 1 And 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 contain 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 according to the invention may be one of the following products: a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior lighting and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cellular telephone, a tablet, a phablet, a Personal Digital Assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall containing multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a sign.
Compared with the prior art, the invention has the beneficial effects that:
the metal complex forms a large conjugated rigid structure ligand by connecting the pyridine derivative and polycyclic naphthalene or polycyclic aza-naphthalene, effectively prevents energy loss caused by free rotation of a single bond, and improves quantum efficiency. The electronic device of the invention can obtain a consumer product with narrow emission spectrum, high stability and high efficiency by containing the organic electroluminescent element.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
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 described layers.
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 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 described layers. Since the most common OLED devices have one light emitting layer, while device 200 has a first light emitting layer and a second light emitting layer, the light emitting peak shapes of the first light emitting layer and the second light emitting layer 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 layer other than the layer containing the metal complex of the present invention is not limited at all, and a person skilled in the art can determine the constitution of other layers of the organic electroluminescent element as necessary based on the general knowledge of the art in the field.
Generally, an OLED comprises 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 described layers.
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 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 described layers. Since the most common OLED devices have one single color light emitting layer or three light emitting layers of three primary colors, while the 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 can 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. A functional OLED may be realized by combining the various layers described in different ways, or several layers may be omitted altogether, based on design, performance and cost factors. 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 a host and a dopant, or more generally, mixtures. Also, the layer may have various sub-layers. 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, OLEDs having 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 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 vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured. Other suitable deposition methods include creating one or more layers, for example by spin coating, or by any desired printing method, such as screen printing, flexographic printing, lithography, photo-induced thermal imaging, thermal transfer, ink jet printing, or nozzle printing. Soluble compounds, for example obtained by appropriate substitution. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which one or more layers are applied, for example, from 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 barrier layer. One use 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, vapor, and/or gas. The barrier layer may be deposited on, under, or beside the substrate, electrode, or any other portion of the device, including the edges. The barrier layer may comprise a single layer or multiple layers. The barrier layer can be formed by various known chemical vapor deposition techniques and can include compositions having a single phase as well as compositions 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 95/5-5/95. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric and inorganic silicon.
In any of the above-mentioned compounds used in each layer of the above-described OLED devices, 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 (such as, but not limited to, alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be non-deuterated, partially deuterated, and fully deuterated forms thereof.
The materials and structures described herein can 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, organic devices such as organic transistors may use the materials and structures.
These methods are generally known to those skilled in the art and they can be applied without inventive effort to organic electroluminescent devices comprising the compounds according to the invention.
According to one embodiment, novel ligands for metal complexes are disclosed. The inventors have discovered 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 includes the following methods, but is not limited thereto, and those skilled in the art can variously change the method according to the general knowledge in the art. The preparation method comprises the following steps:
a cleaning procedure: cleaning the glass substrate with the ITO by using a cleaning agent, deionized water, an organic solvent and the like;
step of forming a hole injection layer: a hole injection layer forming material containing the metal complex of the present invention is vapor-deposited on the anode layer by vacuum vapor deposition, thereby forming a hole injection layer containing the metal complex of the present invention on the substrate;
step (2) 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 evaporation 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 transporting 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: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) life test: an LTS-1004AC life test apparatus was used.
Examples
The invention also discloses a method for preparing the metal complex Ir (LAi) 2 General synthesis method for (LCn), comprising the following steps:
the first step is as follows: preparation of Iridium chloride coordination intermediate
10.0mmol of the compound LAi and 5.0mmol of IrCl 3 ·3H 2 Dispersing O in 30mL of ethylene glycol ethyl ether and 10mL of water, heating and refluxing for reaction for 24 hours under the protection of nitrogen,and cooling to room temperature, filtering, washing a filter cake with water, and drying in vacuum to obtain an iridium chloride coordination intermediate which is directly used for the next preparation without purification.
The second step is that: preparation of the Metal Complex Ir (LAi) 2 (LCn)
Dispersing 5.0mmol of iridium chloride coordination intermediate, 15.0mmol of LCn and 25.0mmol of anhydrous potassium carbonate or anhydrous sodium carbonate in 40mL of acetonitrile and 40mL of chloroform, heating and refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, pouring the reaction liquid into water, extracting with dichloromethane, drying an organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying the residue by a silica gel column to obtain a compound Ir (LAi) 2 (LCn)。
Preparation of the Metal Complex Ir (LAi) 2 (LBj) or Ir (LAi) (LBj) 2 The general synthesis method comprises the following steps:
the first step is as follows: preparation of intermediate Ir (LAi) 2 OTf or Ir (LBj) 2 Alkyl alcohol complex of OTf with Ir (LAi) 2 The OTf is taken as an example of the OTf,
10.0mmol of the compound LAi and 4.5mmol of IrCl 3 ·3H 2 O is dispersed in 150mL of ethylene glycol ethyl ether and 50mL of water, the mixture is heated and refluxed for reaction for 24 hours under the protection of nitrogen, the mixture is cooled to room temperature and filtered, a filter cake is washed by water and ethanol, the mixture is dried in vacuum to obtain a solid, the obtained solid is dissolved in 250mL of dichloromethane and 25mL of methanol, 15.0mmol of silver trifluoromethanesulfonate is added, the mixture is stirred for reaction for 24 hours, the filtration is carried out, the filtrate is decompressed and concentrated to dryness, and a compound Ir (LAi) 2 The methanol complex of OTf, without purification, was used directly in the next step of preparation.
The second step is that: preparation of the Metal Complex Ir (LAi) 2 (LBj)
5.0mmol of the compound LBj and 2.4mmol of the intermediate Ir (LAi) prepared in the first stage 2 Dispersing OTf methanol complex in 50mL ethylene glycol ethyl ether and 50mL DMF, heating to 100 deg.C under nitrogen protection, stirring for reaction for 7 days, cooling to room temperature, concentrating under reduced pressure, purifying with silica gel column, eluting with dichloromethane-n-hexane to obtain compound Ir (LAi) 2 (LBj)。
Preparation of the Metal Complex Ir (LAi) 3 The general synthesis method comprises the following steps:
the first step is as follows: preparation of Iridium chloride coordination intermediate
10.0mmol of the compound LAi and 5.0mmol of IrCl 3 ·3H 2 Dispersing O in 30mL of ethylene glycol ethyl ether and 10mL of water, heating and refluxing for reaction for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water, and drying in vacuum to obtain an iridium chloride coordination intermediate, wherein the red solid is directly used for the next preparation without purification.
The second step: preparation of the Metal Complex Ir (LAi) 3
5.0mmol of intermediate Ir prepared in the first step 2 Cl 2 (LAi) 4 Dispersing 10.0mmol of silver trifluoromethanesulfonate and 12.0mmol of the same compound LAi in 20mL of ethylene glycol ethyl ether, heating under the protection of nitrogen, refluxing, stirring, reacting for 24 hours, cooling to room temperature, filtering, dissolving a filter cake with dichloromethane, and separating and purifying by a silica gel column to obtain a compound Ir (LAi) 3 。
A general synthesis method for preparing a metal complex Pt (LAi) (LBj) comprises the following steps:
the first step is as follows: preparation of platinum chloride coordination intermediate
Dispersing 10.0mmol of compound LAi and 5.0mmol of potassium tetrachloroplatinate in 30mL of ethylene glycol ethyl ether and 10mL of water, heating and refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, filtering, washing a filter cake with water, and drying in vacuum to obtain a platinum chloride coordination intermediate which is directly used for the next preparation without purification.
The second step is that: preparation of the Metal Complex Pt (LAi) (LBj)
Dispersing 5.0mmol of platinum chloride coordination intermediate and 12.5mmol of LBj and 25.0mmol of anhydrous potassium carbonate or anhydrous sodium carbonate in 40mL of acetonitrile and 40mL of chloroform, heating and refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, pouring the reaction liquid into water, extracting with dichloromethane, drying an organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying the residue by a silica gel column to obtain the compound Pt (LAi) or LBj.
Wherein i is an integer of 1 to 436, j is an integer of 1 to 432, and n is an integer of 1 to 44.
Example 1
The preparation of the metal complex Ir (LA4) is described below using the ligands LA4 and LC4 as representative examples 2 (LC4), further elaborating on, the preparation of the metal complex of the present invention, comprises the steps of:
the first step is as follows: preparation of Iridium chloride coordination intermediate
10.0mmol of the compound LA4 and 5.0mmol of IrCl 3 ·3H 2 O DispersionHeating and refluxing the mixture in 30mL of ethylene glycol ethyl ether and 10mL of water under the protection of nitrogen for 24 hours for reaction, cooling the mixture to room temperature, filtering, washing a filter cake with water, and drying the filter cake in vacuum to obtain an iridium chloride coordination intermediate, namely a red solid, wherein the red solid is directly used for the next preparation without purification.
The second step is that: preparation of Metal Complex Ir (LA4) 2 (LC4)
Dispersing 5.0mmol of iridium chloride coordination intermediate, 15.0mmol of LC4 and 25.0mmol of anhydrous sodium carbonate in 40mL of acetonitrile and 40mL of chloroform, heating under reflux for 24 hours under the protection of nitrogen, cooling to room temperature, pouring the reaction solution into water, extracting with dichloromethane, drying the organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying the residue with silica gel column to obtain compound Ir (LA4) 2 (LC4), red solid; the yield is 35-45%.
R 1 、R 2 、R 4 Is hydrogen; r is 3 Is isopropyl; r 5 、R 6 、R 7 、R 8 Is methyl; yield 39%, MS (MALDI-TOF): m/z 1161.5783[ M + H ]] + 。
R 1 、R 2 、R 4 、R 7 、R 8 Is hydrogen; r is 3 Is isopropyl; r 5 、R 6 Is methyl; yield 37%, MS (MALDI-TOF): m/z 1105.5159[ M + H ]] + 。
R 1 、R 2 、R 4 、R 5 、R 6 、R 7 、R 8 Is hydrogen; r 3 Is isopropyl; yield 43%, MS (MALDI-TOF): m/z 1049.4531[ M + H] + 。
Referring to the above synthetic method, preparation of the metal complexes shown in table 1 is exemplified by LCn represented only by ligand LC 4.
TABLE 1 Synthesis of Metal complexes of ligand LC4
Example 2
The preparation of the metal complex Ir (LA153) (LB90) is described below using the ligands LA153 and LB90 as representative examples 2 In further detail, the preparation of the metal complex of the present invention comprises the following steps:
the first step is as follows: preparation of Compound Int-1
Under the protection of nitrogen, 10.0mmol of compound LB90 and 4.5mmol of IrCl 3 ·3H 2 Dispersing O in 150mL of ethylene glycol ethyl ether and 50mL of water, heating and refluxing for reaction for 24 hours, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and drying in vacuum to obtain a yellow solid, dissolving the obtained solid in 250mL of dichloromethane and 25mL of methanol, adding 15.0mmol of silver trifluoromethanesulfonate, stirring for reaction for 24 hours, filtering, and concentrating the filtrate under reduced pressure to obtain a compound Int-1 with yield of 80%, wherein the compound Int-1 is directly used for the next preparation without purification.
The second step is that: compound Ir (LA153) (LB90) 2 Preparation of
5.0mmol of compound LA153 and 2.4mmol of intermediate Int-1 were dispersed in 50mL of ethylene glycol ethyl ether and 50mL of DMF, and the reaction was stirred at 100 ℃ for 7 days under nitrogen protection, cooled to room temperature, and decompressedConcentrating, purifying with silica gel column, eluting with dichloromethane-n-hexane to obtain compound Ir (LA153) (LB90) 2 Dark yellow solid, yield: 40-50%;
R 1 、R 2 is hydrogen, R 5 、R 6 Yield 46% as deuterium, MS (MALDI-TOF): m/z 771.2489[ M + H ]] + 。
R 1 、R 2 Is hydrogen, R 5 、R 6 Yield 48% for methyl-d 3, MS (MALDI-TOF): m/z 803.3049[ M + H] + 。
R 2 Is hydrogen, R 1 、R 5 、R 6 Yield was 42% for methyl-d 3, MS (MALDI-TOF): m/z 820.3396[ M + H ]] + 。
Referring to the above synthesis method, preparation of metal complexes as shown in Table 2 is exemplified by LBj only represented by ligand LB 105.
TABLE 2 Metal complexes synthesized from ligand LB105
EXAMPLE 3 preparation of organic electroluminescent element
The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, vapor-plating a layer on the ITO filmSilver metal as anode layer, and the thickness of evaporated film is
Continuing to respectively evaporate HI02 and F18TP as hole injection layers, wherein F18TP is 3% of HI02 by mass, and the thickness of the evaporated film is
Continuously depositing HTM on the hole injection layer film to form a hole transport layer, wherein the deposition film has a thickness of
Depositing EBM as an electron blocking layer on the hole transport layer to a thickness of
An organic light-emitting layer is evaporated on the electron blocking layer, the light-emitting layer contains H1 as a main body and 3 mass percent of the metal complex prepared by the invention is used as a doping material, and the thickness of the evaporated film is
Depositing an electron transport layer of LiQ and ETM as elements on the organic light-emitting layer, wherein LiQ is 50% of ETM mass, and the deposition film thickness is
Continuously evaporating a layer of LiF on the luminescent layer to form an electron injection layer of the device, wherein the thickness of the evaporated film is
Depositing magnesium and silver as cathode layer of the element on the electron injection layer at a mass ratio of 1: 2, and a thickness of the deposited film
Finally, a layer of CPL as an element NPB is evaporated on the transparent cathode, and the thickness of the evaporated film is
The OLED element provided by the invention is obtained.
Comparative example 1
Comparative element 1 was prepared by following the same procedure as in example 3, except that the compound represented by RD-1 was used in place of the metal complex of the present invention in example 3.
The structural formulas of the HI02, HTM, EBM, H1, LiQ, RD-1, F18TP and ETM are shown as follows:
the organic electroluminescent element prepared by the above process was subjected to the following performance tests:
the driving voltage and current efficiency of the organic electroluminescent elements prepared in example 3 and comparative example 1 and the lifetime of the elements were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and the current density of the organic electroluminescent element was measured to reach 10mA/em 2 The time voltage is the driving voltage, and the brightness at the time is measured; the ratio of the brightness to the current density is the current efficiency; the LT 95% lifetime test is as follows: using a luminance meter at 1000cd/m 2 The luminance degradation of the organic electroluminescent element was measured to 950cd/m while maintaining a constant current at luminance 2 Time in hours. Data is normalized compared to comparative element 1. The results are shown in Table 3.
TABLE 3 test results of device Properties
Wherein R is 1 、R 2 、R 5 、R 6 、R 7 、R 8 Each independently hydrogen, deuterium, methyl or methyl-d 3; r 4 Is hydrogen; r 3 Is isopropyl, tert-butyl or phenyl.
As can be seen from table 3, the metal complex of the present invention as a dopant material of the light emitting layer has a lower driving voltage compared to comparative example 1, and particularly has great advantages in external quantum efficiency and LT 95% lifetime.
Compared with the compound of the invention, the compound RD-1 in the comparative example 1 is distinguished in that isoquinoline is connected with naphthalene through a single bond, the planar conjugation capability is weak, and the compound is in a twisted state under the free rotation vibration of the single bond, so that energy loss is caused, and the performance of metal-ligand charge migration is reduced.
Table 3 above only shows the properties of some metal complexes, and the inventors also conducted the above tests on other metal complexes, and the results are substantially consistent, and are not shown one by one due to the 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 should be apparent that the described embodiments are only some embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without making any creative effort, shall fall within the protection scope of the present invention. The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (10)
1. A metal complex comprising a ligand LA of formula I, wherein formula I has the structure:
wherein X 1 ～X 3 Each independently selected from N or CR 2 ；W 1 ～W 4 Each independently selected from N or CR 3 Or two arbitrary adjacent W 1 And W 2 、W 2 And W 3 Or W 3 And W 4 Represents a group represented by the following formula (II) or formula (III), or a combination thereof;
each X independently represents CR 4 Or N, and two of the vicinities ^ refer to the vicinal radicals W in the formula (I) 1 And W 2 、W 2 And W 3 Or W 3 And W 4 ；
Ring B is a five-membered carbocyclic ring, five-membered heterocyclic ring, six-membered carbocyclic ring, six-membered heterocyclic ring, seven-membered carbocyclic ring or seven-membered heterocyclic ring;
T 1 selected from O, S, Se, NR ', BR ', SiR ' R ", CR ' R", or GeR ' R ";
R 1 、R 2 、R 3 、R 4 、R’r' on each occurrence, identically or differently, is selected from hydrogen, deuterium, a halogen atom, C 1 ～C 40 Chain alkyl radical, C 3 ～C 40 Cycloalkyl radical, C 1 ～C 40 Heteroalkyl group, C 3 ～C 40 Heterocycloalkyl radical, C 6 ～C 60 Aralkyl radical, C 1 ～C 40 Alkoxy radical, C 6 ～C 60 Aryloxy, amino, C 3 ～C 40 Silyl radical, C 2 ～C 40 Alkenyl radical, C 5 ～C 40 Cycloalkenyl radical, C 3 ～C 40 Heteroalkenyl, C 2 ～C 40 Alkynyl, C 6 ～C 60 Aryl radical, C 2 ～C 60 Heteroaryl group, C 1 ～C 40 Acyl, carboxylic acid group, ether, ester group, nitrile group, isonitrile group, sulfur group, sulfinyl group, sulfonyl group and phosphine group; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or polycyclic ring;
the ligand LA is coordinated through a metal M to form a five-membered chelate ring;
wherein the ligand LA may be linked to 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 the ligand LA is selected from the group consisting of:
wherein, T 2 Selected from O, S, NR 'or SiR' R "; x 1 、X 2 、X 3 Each independently is N or CR 2 ；
R 1 ～R 12 R ', R' are, on each occurrence, identically or differently selected from hydrogen, deuterium, a halogen atom, C 1 ～C 40 Chain alkyl radical, C 3 ～C 40 Cycloalkyl radical, C 1 ～C 40 Heteroalkyl group, C 3 ～C 40 Heterocycloalkyl radical, C 3 ～C 40 Silyl radical, C 6 ～C 60 Aryl radical, C 2 ～C 60 Heteroaryl, nitrile; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or polycyclic ring.
3. The metal complex of any one of claims 1 or 2, wherein R is 1 ～R 12 R ', R' are each independently selected, at each occurrence, from hydrogen, deuterium, fluorine, nitrile, R A1 ～R A55 、R B1 ～R B45 、R C1 ～R C295 A group of compounds;
wherein R is A1 ～R A55 The structural formula is as follows:
R B1 ～R B45 the structural formula is as follows:
R C1 ～R C295 the structural formula is as follows:
4. the metal complex of 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 、Ir(LA) 2 (LC) or Ir (LA) (LB) (LC), wherein LA, LB, and LC are different from each other; or the metal complex has the formula Pt () LA) (LB), wherein LA and LB may be the same or different.
5. The metal complex of claim 4, wherein the LB is selected from the group consisting of:
the LC is as follows:
wherein, Y 1 ～Y 14 At each occurrence, each is independently selected from N or CR; t is 1 Each independently selected from BR 3 、NR 4 、PR 5 、O、S、Se、C＝O、S＝O、SO 2 、CR 3 R 4 、SiR 3 R 4 And GeR 3 R 4 One of (1); r 3 And R 4 May be optionally joined or fused to form a ring;
T 2 selected from N, B, SiR, P or P ═ O;
v is selected from B, Al, Ga or In;
each R, R a 、R b 、R c 、R d 、R e 、R f 、R 3 、R 4 、R 5 Each independently selected from hydrogen, deuterium, a halogen atom, C 1 ～C 40 Chain alkyl radical, C 3 ～C 40 Cycloalkyl radical, C 1 ～C 40 Heteroalkyl group, C 3 ～C 40 Heterocycloalkyl radical, C 3 ～C 40 Silyl radical, C 6 ～C 60 Aryl radical, C 2 ～C 60 Heteroaryl, nitrile; and any two or more adjacent substituents are optionally joined or fused together to form a substituted or unsubstituted five-, six-or polycyclic ring.
6. The metal complex as claimed in any one of claims 1 to 5, wherein LB is selected from the group consisting of LB 1-LB 432, and the specific structures of LB 1-LB 432 are as follows:
the LC is selected from a group consisting of structures shown in LC 1-LC 44, and the specific structures of LC 1-LC 44 are shown as follows:
7. the metal complex of any one of claims 1 to 6, wherein the ligand LA comprises one of LA1 to LA436, and LA1 to LA436 have the following specific structures:
wherein R is 1 、R 2 、R 3 、R 4 At each occurrence, each is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, R A1 ～R A55 、R B1 ～R B45 、R C1 ～R C295 A group of compounds;
R 5 、R 6 、R 7 、R 8 、R 9 、R 10 at each occurrence, each is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, R A1 ～R A55 、R B1 ～R B45 A group of combinations thereof.
8. The metal complex of claim 7, wherein R is 1 、R 2 、R 3 、R 4 At each occurrence, each is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, R A1 ～R A3 、R B1 ～R B7 、R C1 ～R C140 A group of compounds; r 5 、R 6 、R 7 、R 8 、R 9 、R 10 At each occurrence, each is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, R A1 ～R A3 、R B1 ～R B7 A group of combinations thereof.
9. The metal complex of any one of claims 1 to 8, wherein the metal complex is Ir (LAi) (LBj) 2 、Ir(LAi) 2 (LBj)、Ir(LAi) 3 、Ir(LAi) 2 (LCn) or Ir (LAi) (LBj) (LCn), wherein i is an integer of 1-436, j is an integer of 1-432, and n is an integer of 1-44; the LA 1-LA 436 is structured as shown in claim 7; the structures of the LB 1-LB 432 and LC 1-LC 44 are shown in claim 6.
10. 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 9.
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