CN117843687A - Luminescent material with multi-ring ligand - Google Patents
Luminescent material with multi-ring ligand Download PDFInfo
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- CN117843687A CN117843687A CN202211206728.0A CN202211206728A CN117843687A CN 117843687 A CN117843687 A CN 117843687A CN 202211206728 A CN202211206728 A CN 202211206728A CN 117843687 A CN117843687 A CN 117843687A
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- carbon atoms
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- 239000000463 material Substances 0.000 title claims abstract description 67
- 239000003446 ligand Substances 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 560
- -1 alkyl germanium Chemical compound 0.000 claims description 176
- 125000001072 heteroaryl group Chemical group 0.000 claims description 93
- 125000001424 substituent group Chemical group 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 239000010410 layer Substances 0.000 claims description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 49
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 44
- 229910052805 deuterium Inorganic materials 0.000 claims description 44
- 229910052751 metal Inorganic materials 0.000 claims description 43
- 239000002184 metal Substances 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000004104 aryloxy group Chemical group 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000006413 ring segment Chemical group 0.000 claims description 25
- 125000005104 aryl silyl group Chemical group 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 229910052732 germanium Inorganic materials 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 239000012044 organic layer Substances 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229910052796 boron Inorganic materials 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 7
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 7
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- WLKSSWJSFRCZKL-UHFFFAOYSA-N trimethylgermanium Chemical compound C[Ge](C)C WLKSSWJSFRCZKL-UHFFFAOYSA-N 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 150000002739 metals Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 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 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 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 claims description 4
- 229960005544 indolocarbazole Drugs 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical group C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003636 chemical group Chemical group 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 15
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 abstract description 9
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000003111 delayed effect Effects 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 150000003384 small molecules Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 5
- 238000000103 photoluminescence spectrum Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 150000002503 iridium Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000003775 Density Functional Theory Methods 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-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
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-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
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-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
- 125000004429 atom Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
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Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
A luminescent material having a multi-ring ligand is disclosed. The luminescent material is a novel metal complex with multi-ring ligand and can be used as the luminescent material in electroluminescent devices. The novel metal complex can realize deep red to near infrared light emission, has very narrow half-peak width, can realize high-saturation luminescence, and has application potential of becoming an excellent deep red to near infrared luminescent material. An electroluminescent device and a compound composition are also disclosed.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. And more particularly, to a metal complex having a multi-ring ligand, an organic electroluminescent device and a compound composition including the same.
Background
Organic electronic devices include, but are not limited to, the following: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLEDs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.
In 1987, tang and Van Slyke of Isomandah reported a double-layered organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters,1987,51 (12): 913-915). Once biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). Most advanced OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Because OLEDs are self-emitting solid state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in flexible substrate fabrication.
OLEDs can be divided into three different types according to their light emission mechanism. The OLED of the Tang and van Slyke invention is a fluorescent OLED. It uses only singlet light emission. The triplet states generated in the device are wasted through non-radiative decay channels. Thus, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation prevents commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs using triplet emission from heavy metals containing complexes as emitters. Thus, both singlet and triplet states can be harvested, achieving a 100% IQE. Because of its high efficiency, the discovery and development of phosphorescent OLEDs has contributed directly to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency by Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons by reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymeric OLEDs depending on the form of the materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of the small molecules can be large as long as they have a precise structure. Dendrimers with a defined structure are considered small molecules. Polymeric OLEDs include conjugated polymers and non-conjugated polymers having pendant luminescent groups. Small molecule OLEDs can become polymeric OLEDs if post-polymerization occurs during fabrication.
Various methods of OLED fabrication exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymeric OLEDs are manufactured by solution processes such as spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be fabricated by solution processes if the material can be dissolved or dispersed in a solvent.
The emission color of an OLED can be achieved by the structural design of the luminescent material. The OLED may include a light emitting layer or layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full color OLED displays typically employ a mixing strategy using blue fluorescent and phosphorescent yellow, or red and green. Currently, a rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
CN104447880a discloses that byRepresented metal complexes, which disclose the complexes in specific structures: />The application claims to have an azacarbazole structure and R 2 The structures shown are metal complexes of ligands formed by c—c bond linkages alone. The application does not disclose metal complexes of ligands having more fused ring structures.
WO2019109886A1 discloses thatRepresented metal complexes, which disclose the complexes in specific structures: />What is claimed in this application is a compound having an azacarbazole structure and Ar 2 The structures shown are metal complexes of ligands formed by c—c bond linkages alone. The application does not disclose metal complexes of ligands having more fused ring structures.
With respect to phosphorescent luminescent materials, some orange-red and red luminescent materials have been reported at present, but various defects still exist, with the wide application of OLEDs, new and higher requirements are put forward for deep red luminescent materials and luminescent materials with near infrared wavelengths, and deep red luminescent materials and near infrared luminescent materials play an important role in special fields of detection, sensing, optical communication, night vision and the like. Therefore, research and development of a luminescent material with a longer luminescence wavelength, a narrower half-width of deep red or even near infrared has important practical significance.
Disclosure of Invention
The present invention aims to solve at least part of the above problems by providing a series of metal complexes with polycyclic ligands. The novel metal complexes can realize deep red to near infrared light emission, have very narrow half-peak width and can realize high-saturation luminescence. Further, the metal complex can be used as a light emitting material in an organic electroluminescent device.
According to one embodiment of the present invention, a metal complex is disclosed comprising a metal M, and a ligand L coordinated to the metal M a The metal M is selected from metals with a relative atomic mass of more than 40, and the ligand L a Has a structure represented by formula 1:
wherein,
w is selected from B, N or P;
k is selected from single bond, O or S;
ring a is selected from a five membered unsaturated carbocycle, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
ring D is selected from a five membered unsaturated carbocycle, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 4 to 30 carbon atoms; and when ring D is selected from five-membered heteroaryl rings, the heteroatoms contained in the five-membered heteroaryl rings are selected from the group consisting of O, S, se, si and P;
ring B is selected from a heterocycle having 2 to 30 carbon atoms or a heteroaryl ring having 2 to 30 carbon atoms;
Ring C is selected from heteroaryl rings having 3 to 30 carbon atoms;
R a 、R b 、R c and R is d Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
R a 、R b 、R c and R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
And R is a 、R b 、R c And R is d Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl havingCycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkyl silicon groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl silicon groups having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl germanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphine groups, and combinations thereof;
Adjacent substituents R a 、R b 、R c And R is d Can optionally be linked to form a ring.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the metal complex shown in the above embodiment.
According to another embodiment of the present invention, there is also disclosed a compound composition comprising the metal complex shown in the above embodiment.
The present invention discloses novel metal complexes with polycyclic ligands. The metal complex can realize deep red to near infrared light emission, has very narrow half-peak width, and can realize high-saturation luminescence. Further, the metal complex can be used as a light emitting material in an electroluminescent device.
Drawings
Fig. 1 is a schematic view of an organic light emitting device that may contain a combination of the metal complexes and compounds disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that may contain a combination of the metal complexes and compounds disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically illustrates, without limitation, an organic light-emitting device 100. The drawings are not necessarily to scale, and some of the layer structures in the drawings may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the layers described. The nature and function of the layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F in a 50:1 molar ratio 4 m-MTDATA of TCNQ as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1 as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of cathodes are disclosed in U.S. Pat. nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, including composite cathodes having a thin layer of metal, such as Mg: ag, with an overlying transparent, electrically conductive, sputter deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided by way of non-limiting example. The function of the OLED may be achieved by combining the various layers described above, or some of the layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sublayers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, such as the organic light emitting device 200 shown schematically and without limitation in fig. 2, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film packages are described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptops, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and taillights.
The materials and structures described herein may also be used in other organic electronic devices as listed above.
As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" on "the second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photosensitive" when it is believed that the ligand directly contributes to the photosensitive properties of the emissive material. When it is believed that the ligand does not contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary," but ancillary ligands may alter the properties of the photosensitive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by spin statistics that delay fluorescence by more than 25%. Delayed fluorescence can be generally classified into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. The P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
On the other hand, the E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between the triplet states and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have very small mono-triplet gaps in order for the conversion between the energy states. The thermal energy may activate a transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the delay component increases with increasing temperature. The fraction of backfill singlet excited states may reach 75% if the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet states. The total singlet fraction may be 100%, well in excess of 25% of the spin statistics of the electrically generated excitons.
The E-type delayed fluorescence characteristic can be seenIn a system of excited complexes or in a single compound. Without being bound by theory, it is believed that E-delayed fluorescence requires a luminescent material with a small mono-triplet energy gap (Δe S-T ). Organic non-metal containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor Charge Transfer (CT) type emission. The spatial separation of HOMO from LUMO in these donor-acceptor compounds generally results in a small Δe S-T . These states may include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
Definition of terms for substituents
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-as used herein, includes straight and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.
Cycloalkyl-as used herein, includes cyclic alkyl. Cycloalkyl groups may be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl are preferred. In addition, cycloalkyl groups may be optionally substituted.
Heteroalkyl-as used herein, a heteroalkyl comprises an alkyl chain in which one or more carbons is replaced by a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl. In addition, heteroalkyl groups may be optionally substituted.
Alkenyl-as used herein, covers straight chain, branched chain, and cyclic alkylene groups. Alkenyl groups may be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight chain alkynyl is contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of the aryl group include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl-4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-tetrabiphenyl. In addition, aryl groups may be optionally substituted.
Heterocyclyl or heterocycle-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms including at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thietaneyl, azepanyl and tetrahydrosilol. In addition, the heterocyclic group may be optionally substituted.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furodipyridine, benzothiophene, thienodipyridine, benzoselenophene, selenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-boron, 1, 3-aza-boron, 1-aza-boron-4-aza, boron-doped compounds, and the like. In addition, heteroaryl groups may be optionally substituted.
Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.
Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenoxy. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl-substituted alkyl. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthyl-ethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthyl-ethyl, 2- β -naphthyl-ethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, cyano, o-cyanobenzyl, o-chlorobenzyl, 1-chlorophenyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. In addition, aralkyl groups may be optionally substituted.
Alkyl-as used herein, alkyl-substituted silicon groups are contemplated. The silyl group may be a silyl group having 3 to 20 carbon atoms, preferably a silyl group having 3 to 10 carbon atoms. Examples of the alkyl silicon group include trimethyl silicon group, triethyl silicon group, methyldiethyl silicon group, ethyldimethyl silicon group, tripropyl silicon group, tributyl silicon group, triisopropyl silicon group, methyldiisopropyl silicon group, dimethylisopropyl silicon group, tri-t-butyl silicon group, triisobutyl silicon group, dimethyl-t-butyl silicon group, and methyldi-t-butyl silicon group. In addition, the alkyl silicon group may be optionally substituted.
Arylsilane-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenyl silyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, arylsilane groups may be optionally substituted.
Alkyl germanium group-as used herein, alkyl substituted germanium groups are contemplated. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkyl germanium groups include trimethyl germanium group, triethyl germanium group, methyl diethyl germanium group, ethyl dimethyl germanium group, tripropyl germanium group, tributyl germanium group, triisopropyl germanium group, methyl diisopropyl germanium group, dimethyl isopropyl germanium group, tri-t-butyl germanium group, triisobutyl germanium group, dimethyl-t-butyl germanium group, methyl-di-t-butyl germanium group. In addition, alkyl germanium groups may be optionally substituted.
Arylgermanium group-as used herein, encompasses at least one aryl or heteroaryl substituted germanium group. The arylgermanium group may be an arylgermanium group having 6-30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of aryl germanium groups include triphenylgermanium group, phenylbiphenyl germanium group, diphenylbiphenyl germanium group, phenyldiethyl germanium group, diphenylethyl germanium group, phenyldimethyl germanium group, diphenylmethyl germanium group, phenyldiisopropylgermanium group, diphenylisopropylgermanium group, diphenylbutylgermanium group, diphenylisobutylglycol group, and diphenyltert-butylgermanium group. In addition, the arylgermanium group may be optionally substituted.
The term "aza" in azadibenzofurans, azadibenzothiophenes and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.
In the present disclosure, when any one of the terms from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, which may be substituted with one or more groups selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted cycloalkyl having 1 to 20 carbon atoms, unsubstituted alkenyl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, unsubstituted arylgermanium groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphine groups, and combinations thereof.
It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.
In the compounds mentioned in this disclosure, the hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because of their enhanced efficiency and stability of the device.
In the compounds mentioned in this disclosure, polysubstituted means inclusive of disubstituted up to the maximum available substitution range. When a substituent in a compound mentioned in this disclosure means multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may be present at a plurality of available substitution positions on its linking structure, and the substituent present at each of the plurality of available substitution positions may be of the same structure or of different structures.
In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring. In the compounds mentioned in this disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents can be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. Where adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic (including spiro, bridged, fused, etc.), as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to further distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
The expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
the expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that the two substituents bound to further distant carbon atoms are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
furthermore, the expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the adjacent two substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
according to one embodiment of the present invention, a metal complex is disclosed comprising a metal M, and a ligand L coordinated to the metal M a The metal M is selected from metals with a relative atomic mass of more than 40, and the ligand L a Has a structure represented by formula 1:
wherein,
w is selected from B, N or P;
k is selected from single bond, O or S;
ring a is selected from a five membered unsaturated carbocycle, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
Ring D is selected from a five membered unsaturated carbocycle, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 4 to 30 carbon atoms; and when ring D is selected from five-membered heteroaryl rings, the heteroatoms contained in the five-membered heteroaryl rings are selected from the group consisting of O, S, se, si and P;
ring B is selected from a heterocycle having 2 to 30 carbon atoms or a heteroaryl ring having 2 to 30 carbon atoms;
ring C is selected from heteroaryl rings having 3 to 30 carbon atoms;
R a 、R b 、R c and R is d Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
R a 、R b 、R c and R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstitutedAlkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 ring atoms, substituted or unsubstituted alkylsilyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted germanium having 0 carbon atoms, carbonyl, cyano, sulfonyl, cyano, carbonyl, sulfonyl, cyano, or any combination thereof;
And R is a 、R b 、R c And R is d Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, and the likeSubstituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Adjacent substituents R a 、R b 、R c And R is d Can optionally be linked to form a ring.
Herein, adjacent substituents R a 、R b 、R c And R is d Can optionally be linked to form a ring, intended to mean groups of adjacent substituents therein, e.g. adjacent substituents R a Between adjacent substituents R b Between adjacent substituents R c Between adjacent substituents R d Between adjacent substituents R a And R is R b Between adjacent substituents R a And R is R d Between, and adjacent substituents R b And R is R c In between, any one or more of these substituent groups can be linked to form a ring. Obviously, none of these adjacent groups of substituents may be linked to form a ring.
According to one embodiment of the present invention, a metal complex is disclosed comprising a metal M, and a ligand L coordinated to the metal M a The metal M is selected from metals with a relative atomic mass of more than 40, and the ligand L a Has a structure represented by formula 1-1:
wherein,
w is selected from B, N or P;
k is selected from single bond, O or S;
ring a is selected from a five membered unsaturated carbocycle, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
ring B is selected from a heterocycle having 2 to 30 carbon atoms or a heteroaryl ring having 2 to 30 carbon atoms;
ring C is selected from heteroaryl rings having 3 to 30 carbon atoms;
R a 、R b And R is c Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
D 1 、D 2 is selected identically or differently on each occurrence from N or CR d ；
R a 、R b 、R c And R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
And R is a 、R b 、R c And R is d Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 20 carbon atomsAn alkoxy group of a child, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Adjacent substituents R a 、R b 、R c And R is d Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein the L a Wherein ring A is selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms; ring B is selected from heteroaromatic rings having 2 to 18 carbon atoms; ring C is selected from heteroaryl rings having 3 to 18 carbon atoms; ring D is selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 4 to 18 carbon atoms, and when ring D is selected from a five membered heteroaromatic ring, the heteroatoms contained in the five membered heteroaromatic ring are selected from the group consisting of O, S, se, si, P.
According to one embodiment of the invention, wherein the L a Wherein ring a is selected from a benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, furan ring, thiophene ring, selenophene ring, isoxazole ring, isothiazole ring, pyrrole ring, pyrazole ring, benzofuran ring, benzothiophene ring, azabenzofuran ring, or azabenzothiophene ring; ring B is selected from a pyrrole ring, an indole ring, an imidazole ring, a pyrazole ring, a triazole ring, or an azaindole ring; ring C is selected from a pyridine ring, a quinoline ring, an azabenzofuran ring, an azabenzothiophene ring, a pyrazole ring, an isoxazole ring, or an isothiazole ring; ring D is selected from benzene ring, naphthalene ring, pyridine ring, quinoline ring, isoquinoline ring, furan ring, thiophene ring, selenophene ring, benzofuro A furan ring, or a benzothiophene ring.
According to one embodiment of the invention, wherein the L a Wherein ring A and ring D are each independently selected from benzene ring, naphthalene ring, or pyridine ring; ring B is selected from a pyrrole ring, an indole ring, or an azaindole ring; ring C is selected from pyridine ring or quinoline ring.
According to one embodiment of the invention, wherein K is selected from single bonds and L is a A structure selected from any one of formulas 2 to 21:
wherein,
w is selected identically or differently on each occurrence from B, N or P;
A 1 -A 5 is selected identically or differently on each occurrence from N or CR a ；
B 1 -B 4 Is selected identically or differently on each occurrence from N or CR b ；
C 1 -C 4 Is selected identically or differently on each occurrence from N or CR c ；
D 1 -D 4 Is selected identically or differently on each occurrence from N or CR d ；
Z is selected identically or differently at each occurrence from O, S, se, NR z ，CR z R z ，SiR z R z Or PR (PR) z The method comprises the steps of carrying out a first treatment on the surface of the When a plurality of R are simultaneously present z When a plurality of R z The same or different;
x is selected, identically or differently, at each occurrence, from O, S, se, CR d R d ，SiR d R d Or PR (PR) d The method comprises the steps of carrying out a first treatment on the surface of the When a plurality of R are simultaneously present d When a plurality of R d The same or different;
R a 、R b 、R c 、R d and R is z And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
And R is a 、R b 、R c 、R d And R is z Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atomsUnsubstituted aryl silyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl germanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Adjacent substituents R a 、R b 、R c 、R d And R is z Can optionally be linked to form a ring.
In this embodiment, adjacent substituents R a 、R b 、R c 、R d And R is z Can optionally be linked to form a ring, intended to mean groups of adjacent substituents therein, e.g. adjacent substituents R a Between adjacent substituents R b Between adjacent substituents R c Between adjacent substituents R d Between adjacent substituents R a And R is R b Between adjacent substituents R a And R is R d Between adjacent substituents R b And R is R c Between adjacent substituents R a And R is R z Between adjacent substituents R c And R is R z Between adjacent substituents R d And R is R z Between, and adjacent substituents R z In between, any one or more of these substituent groups can be linked to form a ring. Obviously, none of these adjacent groups of substituents may be linked to form a ring.
According to one embodiment of the invention, wherein L a Selected from the structures represented by formula 2, formula 3, or formula 12.
According to one embodiment of the present invention, in the formulas 1 to 21, W is N.
According to one embodiment of the present invention, wherein, in the formulas 2 to 20, C 1 And C 2 At least one of which is N.
According to one embodiment of the present invention, wherein, in the formulas 2 to 20, C 1 Is N.
According to one embodiment of the inventionFor example, wherein, in the formulae 2 to 21, A 1 -A 5 Each independently selected from CR a ，B 1 -B 4 Each independently selected from CR b ，C 1 -C 4 Each independently selected from CR c ，D 1 -D 4 Each independently selected from CR d The method comprises the steps of carrying out a first treatment on the surface of the The R is a 、R b 、R c And R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
And said R is a 、R b 、R c And R is d Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 20 carbon atomsSubstituted or unsubstituted aryloxy groups having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Adjacent substituents R a 、R b 、R c And R is d Can optionally be linked to form a ring.
According to one embodiment of the present invention, wherein, in the formulas 2 to 21, A 1 -A 5 Each independently selected from CR a ，B 1 -B 4 Each independently selected from CR b ，C 1 -C 4 Each independently selected from CR c ，D 1 -D 4 Each independently selected from CR d The method comprises the steps of carrying out a first treatment on the surface of the The R is a 、R b 、R c And R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, and combinations thereofCombining;
and said R is a 、R b 、R c And R is d Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, and combinations thereof.
According to one embodiment of the present invention, wherein, in the formulas 2 to 21, A 1 -A 5 Each independently selected from CR a ，B 1 -B 4 Each independently selected from CR b ，C 1 -C 4 Each independently selected from CR c ，D 1 -D 4 Each independently selected from CR d The method comprises the steps of carrying out a first treatment on the surface of the The R is a 、R b 、R c And R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, cyano, and combinations thereof;
and said R is a 、R b 、R c And R is d Is the same or not at each occurrence of at least one ofAnd is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the present invention, wherein, in the formulas 2 to 21, B 1 -B n At least one of which is selected, identically or differently, at each occurrence, from CR b The B is n Corresponds to the B 1 -B 4 The number of which is the largest in any one of formulas 2 to 21; and said R is b And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilicon having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, and combinations thereof;
Adjacent substituents R b Can optionally be linked to form a ring.
In this embodiment, adjacent substituents R b Can be optionally linked to form a ring, aimed atIn which any adjacent substituents R are represented b Can be connected to form a ring. Obviously, any adjacent substituents R b Or may not be connected to form a ring.
In the present embodiment, in the formulas 2 to 21, B 1 -B n At least 1 of which is selected, identically or differently, at each occurrence, from CR b The B is n Corresponds to the B 1 -B 4 The one having the largest sequence number in any of formulas 2 to 21, for example, in the case of formula 2, the above-mentioned B n Corresponds to the B 1 -B 4 The number with the largest number B in formula 2 4 I.e. in formula 2, B 1 -B 4 At least 1 of which is selected, identically or differently, at each occurrence, from CR b The method comprises the steps of carrying out a first treatment on the surface of the For another example, for formula 4, the B n Corresponds to the B 1 -B 4 The number with the largest number B in formula 4 2 I.e. in formula 4, B 1 -B 2 At least 1 of which is selected, identically or differently, at each occurrence, from CR b 。
According to one embodiment of the present invention, wherein, in the formula 2, formula 3, formula 5 to formula 12, formula 16, and formula 18 to formula 21, B 2 And/or B 3 Is selected from CR, identically or differently at each occurrence b The method comprises the steps of carrying out a first treatment on the surface of the In the formulas 4, 13 to 15 and 17, B 1 And/or B 2 Is selected from CR, identically or differently at each occurrence b 。
According to one embodiment of the present invention, wherein, in the formula 2, formula 3, formula 5 to formula 12, formula 16, and formula 18 to formula 21, B 2 And/or B 3 Selected from CR b The method comprises the steps of carrying out a first treatment on the surface of the In the formulas 4, 13 to 15 and 17, B 1 And/or B 2 Selected from CR b The method comprises the steps of carrying out a first treatment on the surface of the The R is b And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluoro, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, epoxyhexyl, norbornyl, adamantyl, trimethylsilyl, trimethylgermanium, phenyl, pyridinyl, triazinyl, trifluoromethyl, methoxy, methylthio, N, N-dimethylamino, furanyl, thienylAnd combinations thereof.
According to one embodiment of the present invention, wherein, in the formulas 2 to 20, C 1 And/or C 2 Is selected from CR, identically or differently at each occurrence c The method comprises the steps of carrying out a first treatment on the surface of the And said R is c And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, and combinations thereof.
According to one embodiment of the present invention, wherein, in the formulas 2 to 20, C 1 And/or C 2 Is selected from CR, identically or differently at each occurrence c The method comprises the steps of carrying out a first treatment on the surface of the The R is c And is selected identically or differently on each occurrence from the group consisting of: deuterium, cyano, fluorine, trifluoromethyl, methyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, trimethylgermanium, phenyl, pyridinyl, triazinyl, and combinations thereof.
According to one embodiment of the present invention, wherein, in the formulas 2 to 21, A 1 -A n At least one of them is selected from CR a The method comprises the steps of carrying out a first treatment on the surface of the The A is n Corresponds to the A 1 -A 5 The number of which is the largest in any one of formulas 2 to 21; and/or, in the formulas 2 to 21, D 1 -D n At least one of them is selected from CR d The D is n Corresponds to the D 1 -D 4 The number of which is the largest in any one of formulas 2 to 21; the R is a 、R d And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atomsSubstituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having from 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, cyano groups, and combinations thereof.
In the present embodiment, in the formulas 2 to 21, a 1 -A n At least 1 of which is selected, identically or differently, at each occurrence, from CR a The A is n Corresponds to the A 1 -A 5 The one having the largest sequence number in any of formulas 2 to 21, for example, in the case of formula 2, the sequence number A n Corresponds to the A 1 -A 5 The sequence number with the largest value A in formula 2 3 I.e. in formula 2, A 1 -A 3 At least 1 of which is selected, identically or differently, at each occurrence, from CR a The method comprises the steps of carrying out a first treatment on the surface of the For another example, for formula 9, the A n Corresponds to the A 1 -A 5 The number with the largest value A in formula 9 5 I.e. in formula 9, A 1 -A 5 At least 1 of which is selected, identically or differently, at each occurrence, from CR a The method comprises the steps of carrying out a first treatment on the surface of the For another example, for formula 15, the A n Corresponds to the A 1 -A 5 The number with the largest value A in formula 15 1 I.e. in formula 15, A 1 Is selected from CR, identically or differently at each occurrence a 。
In the present embodiment, in the formulas 2 to 21, D 1 -D n At least 1 of which is selected, identically or differently, at each occurrence, from CR d The D is n Corresponds to the D 1 -D 4 The one having the largest sequence number in any of formulas 2 to 21, for example, in the case of formula 2, the above D n Corresponds to the D 1 -D 4 The number D with the largest number in formula 2 2 I.e. in formula 2, D 1 -D 2 At least 1 of which is selected, identically or differently, at each occurrence, from CR d The method comprises the steps of carrying out a first treatment on the surface of the For another example, for formula 12, the D n Corresponds to the D 1 -D 4 The number D with the largest number in formula 12 4 I.e. in formula 12, D 1 -D 4 At least 1 of which is selected, identically or differently, at each occurrence, from CR d 。
According to one embodiment of the present invention, wherein, in the formulas 2 to 14 and 18 to 21, A 1- A 3 At least one of which is selected, identically or differently, at each occurrence, from CR a The method comprises the steps of carrying out a first treatment on the surface of the In the formulae 15 to 17, A 1 Selected from CR a The method comprises the steps of carrying out a first treatment on the surface of the In the formulas 2 to 17 and 19 to 21, D 1 And/or D 2 Selected from CR d 。
According to one embodiment of the present invention, wherein, in the formulas 2 to 14 and 18 to 21, A 1- A 3 At least one of which is selected, identically or differently, at each occurrence, from CR a The method comprises the steps of carrying out a first treatment on the surface of the In the formulae 15 to 17, A 1 Selected from CR a The method comprises the steps of carrying out a first treatment on the surface of the In the formulas 2 to 17 and 19 to 21, D 1 And/or D 2 Selected from CR d The method comprises the steps of carrying out a first treatment on the surface of the The R is a 、R d And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluoro, cyano, trifluoromethyl, methyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethylene, cyclohexyl, trimethylsilyl, trimethylgermanium, phenyl, pyridinyl, triazinyl, and combinations thereof.
According to one embodiment of the invention, wherein in the formulae 4 to 7, 10, 11, 15 to 21, Z is selected identically or differently from O, S or Se for each occurrence.
According to one embodiment of the invention, wherein in the formulae 4 to 7, 10, 11, 15 to 21, Z is selected identically or differently from O or S for each occurrence.
According to one embodiment of the invention, wherein the L a Is selected identically or differently on each occurrence from the group consisting of L a1 To L a666 A group of; the L is a1 To L a666 See claim 10 for a specific structure of (c).
According to one embodiment of the invention, wherein the L a1 To L a666 Hydrogen in the structure of (a) can be partially or completely substituted with deuterium.
According to one embodiment of the invention, wherein the metal complex has M (L a ) m (L b ) n (L c ) q Is of the general formula (I);
wherein the metal M is selected from metals with relative atomic mass greater than 40; l (L) a 、L b And L c A first ligand, a second ligand and a third ligand coordinated to the metal M, respectively; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M; when m is equal to 2 or 3, a plurality of L a May be the same or different; when n is equal to 2, 2L b May be the same or different; when q is equal to 2, 2L c May be the same or different;
L a 、L b and L c Can optionally be linked to form a multidentate ligand;
L b and L c And is selected identically or differently on each occurrence from the group consisting of:
Wherein,
R i 、R ii and R is iii Each occurrence, identically or differently, represents mono-substituted, poly-substituted or unsubstituted;
X a and is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR N1 And CR (CR) C1 R C2 ；
X b And X c And is selected identically or differently on each occurrence from the group consisting of: o, S, se and NR N2 ；
R i 、R ii 、R iii 、R N1 、R N2 、R C1 And R is C2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Adjacent substituents R i 、R ii 、R iii 、R N1 、R N2 、R C1 And R is C2 Can optionally be linked to form a ring.
In this embodiment, adjacent substituents R i 、R ii 、R iii 、R N1 、R N2 、R C1 And R is C2 Can optionally be linked to form a ring, intended to mean that in said L b 、L c Adjacent substituent groups in the structure of (a), e.g. adjacent substituent R i Between adjacent substituents R ii Between adjacent substituents R iii Between adjacent substituents R i And R is R ii Between adjacent substituents R ii And R is R iii Between adjacent substituents R i And R is R iii Between adjacent substituents R i And R is R N1 Between adjacentSubstituent R of (2) i And R is R C1 Between adjacent substituents R i And R is R C2 Between adjacent substituents R ii And R is R N1 Between adjacent substituents R iii And R is R N1 Between adjacent substituents R ii And R is R C1 Between adjacent substituents R ii And R is R C2 Between adjacent substituents R iii And R is R C1 Between adjacent substituents R iii And R is R C2 Between adjacent substituents R i And R is R N2 Between adjacent substituents R ii And R is R N2 Between, and adjacent substituents R C1 And R is R C2 Any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be linked to form a ring. For example, the number of the cells to be processed,r is an adjacent substituent i ，R ii Can optionally be linked to form a ring, which can form a ring comprising, but not limited to, one or more of the following structures: / >
Wherein V is selected from O, S, se, NR ' or CR ' R '; wherein said R', R i ’，R ii ' definition and R i The same applies. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein the metal M is selected from Ir, rh, re, os, pt, au or Cu.
According to one embodiment of the invention, wherein the metal M is selected from Ir, pt or Os.
According to one embodiment of the invention, wherein the metal M is Ir.
According to one embodiment of the invention, wherein the L b Each occurrence is identically or differently selected from the following structures:
wherein R is 1 –R 7 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted alkenyl having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms, substituted aryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted carbon atoms.
According to one embodiment of the invention, wherein the L b Each occurrence is identically or differently selected from the following structures:
wherein R is 1 -R 3 At least one or two of which are identically or differently selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms,substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or a combination thereof; and/or R 4 -R 6 At least one or two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 1 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein the L b Each occurrence is identically or differently selected from the following structures:
wherein R is 1 -R 3 At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 2 to 20 carbon atoms, or combinations thereof; and/or R 4 -R 6 At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 2 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein the L b Is selected identically or differently on each occurrence from the group consisting of L b1 To L b322 A group of; the L is b1 To L b322 See claim 14 for a specific structure.
According to one embodiment of the invention, wherein the L c Is selected identically or differently on each occurrence from the group consisting of L c1 To L c231 A group of; the L is c1 To L c231 See claim 14 for a specific structure.
According to one embodiment of the invention, wherein the metal complex is an Ir complex and has a structure as shown in Ir (L a )(L b )(L c )、Ir(L a ) 2 (L b )、Ir(L a ) 2 (L c ) And Ir (L) a )(L c ) 2 Any of the structures shown; when the metal complex has Ir (L) a )(L b )(L c ) In the structure of (2), the L a Selected from the group consisting of L a1 To L a666 Any one of the group consisting of the L b Selected from the group consisting of L b1 To L b322 Any one of the group consisting of the L c Selected from the group consisting of L c1 To L c231 Any one of the group consisting of; when the metal complex has Ir (L) a ) 2 (L b ) In the structure of (2), the L a Is selected identically or differently on each occurrence from the group consisting of L a1 To L a666 Either or both of the group consisting of, L b Selected from the group consisting of L b1 To L b322 Any one of the group consisting of; when the metal complex has Ir (L) a ) 2 (L c ) In the structure of (2), the L a Is selected identically or differently on each occurrence from the group consisting of L a1 To L a666 Either or both of the group consisting of, L c Selected from the group consisting of L c1 To L c231 Any one of the group consisting of; when the metal complex has Ir (L) a )(L c ) 2 In the structure of (2), the L a Selected from the group consisting of L a1 To L a666 Any one of the group consisting of the L c Is selected identically or differently on each occurrence from the group consisting of L c1 To L c231 Either or both of the groups.
According to one embodiment of the invention, wherein the metal complex is selected from the group consisting of compound 1 to compound 433; the specific structure of said compounds 1 to 433 is seen in claim 15.
According to an embodiment of the present invention, there is also disclosed an electroluminescent device including:
an anode is provided with a cathode,
a cathode electrode, which is arranged on the surface of the cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex, the specific structure of the metal complex being as described in any of the foregoing embodiments.
According to one embodiment of the invention, in the device, the organic layer is a light emitting layer and the metal complex is a light emitting material.
According to one embodiment of the invention, the electroluminescent device emits red light.
According to one embodiment of the invention, the electroluminescent device emits white light.
According to one embodiment of the invention, in the device, the light emitting layer further comprises at least one host material.
According to one embodiment of the invention, the device wherein the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
According to one embodiment of the invention, the host material in the device may be a conventional host material of the prior art, for example, which may typically, but not limited to, include the following host materials:
according to another embodiment of the present invention, there is also disclosed a compound composition comprising a metal complex, the specific structure of which is as shown in any of the preceding embodiments.
Combined with other materials
The materials described herein for specific layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application 2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as useful for specific layers in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in combination with a variety of light-emitting dopants, hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. 2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
In the examples of material synthesis, all reactions were carried out under nitrogen protection, unless otherwise indicated. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structural confirmation and characterization testing using one or more equipment conventional in the art (including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai's optical technique fluorescence spectrophotometer, wuhan Koste's electrochemical workstation, anhui Bei Yi g sublimator, etc.), in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Frieda, st. John's, an ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.
In the preparation of the device, when more than two main materials and luminescent materials are used for co-evaporation to form the luminescent layer, the luminescent layer can be formed by respectively placing more than two main materials and the luminescent materials in different evaporation sources for co-evaporation, or the luminescent layer can be formed by placing a pre-mixed mixture of more than two main materials in the same evaporation source and then co-evaporation with the luminescent materials placed in another evaporation source, and the pre-mixing mode can further save the evaporation sources.
Material synthesis examples:
the preparation method of the compound of the present invention is not limited, and is typically, but not limited to, exemplified by the following compounds, the synthetic routes and preparation methods thereof are as follows:
synthesis example 1: synthesis of Compound 156
Step 1: synthesis of intermediate 3
Intermediate 1 (12.03 g,39.5 mmol) was mixed with PEPSI-IPr ([ 1, 3-bis (2, 6-diisopropylphenyl) imidazol-2-ylidene ] (3-chloropyridine) palladium dichloride) (1.08 g,1.6 mmol) in THF (200 mL). After nitrogen was replaced, a neopentyl magnesium bromide solution (100 mL,63.2 mmol) was added thereto, and the reaction was carried out at room temperature overnight, a saturated aqueous ammonium chloride solution was added to the reaction mixture to quench the reaction mixture, extraction was carried out with ethyl acetate, and the organic phase was collected, concentrated and purified by column chromatography to give intermediate 3 (8.2 g).
Step 2: synthesis of intermediate 4
Intermediate 3 (8.1 g,27.4 mmol) was mixed with m-chloroperoxybenzoic acid (18.35 g,90.4 mmol) in DCE (1, 2-dichloroethane)/EtOH (140 mL) and reacted overnight at 60 ℃. To the reaction mixture was added 1mol/L aqueous sodium hydroxide solution (90 mL), and after stirring for 30 minutes, DCM was added for extraction, and the organic phases were combined and purified by column chromatography to give intermediate 4 (4.9 g).
Step 3: synthesis of intermediate 5
Oxalyl chloride (2.84 g,22.4 mmol) was added dropwise to a solution of intermediate 4 (3.5 g,11.2 mmol) and triethylamine (2.27 g,22.4 mmol) in DCM (34 mL) at-72℃and allowed to react overnight after natural warming to room temperature, meOH (3 mL) was added to the reaction solution, followed by washing with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride in sequence, and the organic phase was collected, concentrated and purified by column chromatography to give intermediate 5 (2.5 g).
Step 4: synthesis of intermediate 6
To a solution of intermediate 5 (1 g,3 mmol), trimethyl orthoformate (3.18 g,30 mmol) and methanol (1.62 g,30 mmol) in nitromethane was added dropwise trifluoromethanesulfonic acid (1.35 g,9 mmol) at 0℃followed by heating to 100℃for 2 hours. After dilution with ethyl acetate, washing with saturated aqueous sodium chloride, concentration and purification by column chromatography gave intermediate 6 (410 mg).
Step 5: synthesis of intermediate 8
Intermediate 6 (400 mg,1.47 mmol), intermediate 7 (491 mg,1.7 mmol), palladium acetate (15.7 mg,0.07 mmol), SPhos (2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl) (57.5 mg,0.14 mmol) and sodium carbonate (233 mg,2.2 mmol) were mixed in a round bottom flask, and 1, 4-dioxane (6 mL) and water (1.5 mL) were added thereto after nitrogen substitution, and reacted overnight at 100 ℃. After cooling to room temperature, it was diluted with ethyl acetate, washed with water, and the organic phase was collected for column chromatography purification to give intermediate 8 (106 mg).
Step 6: synthesis of Iridium dimer 9
Intermediate 8 (100 mg,0.27 mmol), irCl 3 ·3H 2 O (38.7 mg,0.11 mmol) was mixed with ethoxyethanol (6 mL) and water (2 mL), and after nitrogen substitution, the mixture was refluxed at 130℃for 24 hours, and after cooling the reaction to room temperature, the mixture was concentrated to give iridium dimer 9, which was used in the next step without further purification.
Step 7: synthesis of Compound 156
The iridium dimer 9 obtained in the previous step was reacted with 3, 7-diethyl-3, 7-dimethyl-4, 6-nonanedione (53 mg,0.22 mmol), K 2 CO 3 (76 mg,0.55 mmol) and ethoxyethanol (6 mL) were mixed in a 100mL single-necked flask, replaced with nitrogen, reacted at 55℃overnight, and after completion of the TLC monitoring, cooled to room temperature. The reaction solution was filtered through celite, the filter cake was washed with a suitable amount of EtOH, the crude product was dissolved with DCM, a suitable amount of EtOH was added thereto, concentrated at normal temperature until the product precipitated, filtered off, dried and purified by column chromatography to give compound 156 (10 mg, yield 8%) which was confirmed by MS to be structurally correct and molecular weight 1154.5.
Those skilled in the art will recognize that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other compound structures of the present invention.
Photoluminescence spectrum data of compound 156 was measured in the present invention to verify its luminescence properties.
Determination of photoluminescence spectra:
photoluminescence spectrum (PL) data of compound 156 of the present invention was measured using a fluorescence spectrophotometer model number prismatic F98, manufactured by Shanghai prismatic light technologies, inc. The specific test method comprises the following steps: samples of the examples were formulated with HPLC grade toluene to a concentration of 3X 10 -5 mol/LThe solution was then excited with light of 590nm wavelength at room temperature (298K) and its emission spectrum was measured. Photoluminescence spectra of the compound 156 of the present invention were measured, and further triplet energy level (T1) and full width at half maximum (FWHM) of the compound 156 were obtained, and the data are shown in table 1.
Table 1T 1 and FWHM data for compound 156
| Numbering of compounds | T1(eV) | FWHM(nm) |
| Compound 156 | 1.73 | 29.9 |
As can be seen from the data in table 1, the compound 156 comprising the ligand having the structure of formula 1 disclosed in the present invention has T1 of 1.73eV (716 nm), and is a near infrared light emitting compound. In the patent applications CN104447880A and WO2019109886A1, the emission wavelengths of the comparative examples RD-A and RD-B were 582nm (T1: 2.13 eV) and 584nm (T1: 2.12 eV), respectively, and they were orange light-emitting compounds. Compared with the compound RD-A and the compound RD-B, the luminescence wavelength of the compound 156 of the invention is respectively shifted by 134nm and 132nm in red. It can be seen that the compound 156 of the present invention can emit near infrared light through the multi-ring ligand design, and the half-width thereof is quite narrow, namely, only 29.9nm, which is a level which is not achieved by most commercial materials at present, and shows that the compound 156 of the present invention has very excellent luminescence performance. It can be seen that the metal complex disclosed in the present invention can achieve near infrared light emission and has a very narrow half-peak width due to the main ligand having the multi-ring structure represented by formula 1, and can achieve high saturation luminescence. Further, the compound has the potential of becoming an excellent near infrared luminescent material in an organic electroluminescent device.
Specific structure of comparative example compound RD-A and RD-B:
the compound of the present invention can achieve near infrared luminescence due to ligand design with multiple parallel rings, and to further verify the luminescence effect, a three-wire state energy level (T1) of the compound 156, 174, 272, 432 and the comparative example compound RD-C disclosed by the present invention is obtained by performing DFT calculation in a Gaussian (Gaussian) software package by using a B3LYP hybridization functional group and a CEP-31G effective nuclear potential group and an SMD solvation model to simulate THF solvent environment.
The structures of compound 156, compound 174, compound 272, compound 432, and comparative compound RD-C are shown below:
discussion:
the calculated T1 of the compound 156 of the present invention is 1.64eV, and the difference from the actual measured T1 (1.73 eV) of the compound 156 is only 0.09eV, indicating that the calculated data can reflect the luminescence properties of the compound of the present invention.
The calculated T1 value of the compound RD-C of the comparative example is 1.90eV, which is dark red luminescence, and compared with the compound RD-C of the comparative example, the azacarbazole of the compound 156 of the invention is further connected with naphthalene ring to form a ring, so that the T1 of the compound 156 of the invention is reduced to 1.64eV, which is near infrared luminescence; the T1 of the compound 174, the compound 272 and the compound 432 are respectively 1.64eV,1.49eV and 1.50eV, and are respectively near infrared luminescence, which further indicates that the compound of the invention can achieve near infrared emission due to the special multi-ring ligand design, thus having important application potential in the fields of communication and the like; further, the HOMO levels of the compound 156 of the present invention and the compound RD-C of the comparative example were calculated by DFT (the calculation method is the same as the calculation method of T1 described above), and the HOMO level value of the compound 156 of the present invention was-4.68 eV, the HOMO level value of the compound RD-C of the comparative example was-4.84 eV, and the hole trapping ability of the compound 156 of the present invention was stronger than that of the compound RD-C of the comparative example, contributing to higher efficiency in the device. The above data illustrate the wide potential applicability of the compounds of the present invention in the near infrared field.
In summary, the compounds disclosed in the present invention can realize deep red to near infrared light emission, have very narrow half-peak widths, and can realize high-saturation luminescence. The metal complex with the multi-ring ligand disclosed by the invention has excellent performance and potential application prospect of becoming an excellent deep red to near infrared luminescent material.
It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. Thus, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. It is to be understood that the various theories as to why the present invention works are not intended to be limiting.
Claims (20)
1. A metal complex comprising a metal M, and a ligand L coordinated to the metal M a The metal M is selected from metals with a relative atomic mass of more than 40, and the ligand L a Has a structure represented by formula 1:
wherein,
w is selected from B, N or P;
k is selected from single bond, O or S;
ring a is selected from a five membered unsaturated carbocycle, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
Ring D is selected from a five membered unsaturated carbocycle, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 4 to 30 carbon atoms; and when ring D is selected from five-membered heteroaryl rings, the heteroatoms contained in the five-membered heteroaryl rings are selected from the group consisting of O, S, se, si and P;
ring B is selected from a heterocycle having 2 to 30 carbon atoms or a heteroaryl ring having 2 to 30 carbon atoms;
ring C is selected from heteroaryl rings having 3 to 30 carbon atoms;
R a 、R b 、R c and R is d Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
R a 、R b 、R c and R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
And R is a 、R b 、R c And R is d Is identical at each occurrence orDifferently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Adjacent substituents R a 、R b 、R c And R is d Can optionally be linked to form a ring.
2. The metal complex of claim 1, wherein L a Wherein ring A is selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms; ring B is selected from heteroaromatic rings having 2 to 18 carbon atoms; ring C is selected from heteroaryl rings having 3 to 18 carbon atoms; ring D is selected from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 4 to 18 carbon atoms, and when ring D is selected from a five membered heteroaromatic ring, the heteroatoms contained in the five membered heteroaromatic ring are selected from the group consisting of O, S, se, si and P;
preferably, ring a is selected from a benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, furan ring, thiophene ring, selenophene ring, isoxazole ring, isothiazole ring, pyrrole ring, pyrazole ring, benzofuran ring, benzothiophene ring, azabenzofuran ring, or azabenzothiophene ring; ring B is selected from a pyrrole ring, an indole ring, an imidazole ring, a pyrazole ring, a triazole ring, or an azaindole ring; ring C is selected from a pyridine ring, a quinoline ring, an azabenzofuran ring, an azabenzothiophene ring, a pyrazole ring, an isoxazole ring, or an isothiazole ring; ring D is selected from a benzene ring, naphthalene ring, pyridine ring, quinoline ring, isoquinoline ring, furan ring, thiophene ring, selenophene ring, benzofuran ring, or benzothiophene ring;
More preferably, ring a and ring D are each independently selected from a benzene ring, a naphthalene ring, or a pyridine ring; ring B is selected from a pyrrole ring, an indole ring, or an azaindole ring; ring C is selected from pyridine ring or quinoline ring.
3. The metal complex of claim 1, wherein K is selected from single bonds and L is a A structure selected from any one of formulas 2 to 21:
wherein,
w is selected identically or differently on each occurrence from B, N or P;
A 1 -A 5 is selected identically or differently on each occurrence from N or CR a ；
B 1 -B 4 Is selected identically or differently on each occurrence from N or CR b ；
C 1 -C 4 Is selected identically or differently on each occurrence from N or CR c ；
D 1 -D 4 Is selected identically or differently on each occurrence from N or CR d ；
Z is selected identically or differently at each occurrence from O, S, se, NR z ，CR z R z ，SiR z R z Or PR (PR) z The method comprises the steps of carrying out a first treatment on the surface of the When a plurality of R are simultaneously present z When a plurality of R z The same or different;
x is selected, identically or differently, at each occurrence, from O, S, se, CR d R d ，SiR d R d Or PR (PR) d The method comprises the steps of carrying out a first treatment on the surface of the When a plurality of R are simultaneously present d When a plurality of R d The same or different;
R a 、R b 、R c 、R d and R is z And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
And R is a 、R b 、R c 、R d And R is z Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atomsAralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Adjacent substituents R a 、R b 、R c 、R d And R is z Can optionally be linked to form a ring;
preferably, the L a Selected from the structures represented by formula 2, formula 3, or formula 12.
4. A metal complex according to claim 3, wherein in the formulae 2 to 21, W is N.
5. The metal complex according to claim 3 or 4, wherein, in the formulae 2 to 20, C 1 And C 2 At least one of them is N; preferably, in the formulas 2 to 20, C 1 Is N.
6. The metal complex according to claim 3, wherein, in the formulae 2 to 21, A 1 -A 5 Each independently selected from CR a ，B 1 -B 4 Each independently selected from CR b ，C 1 -C 4 Each independently selected from CR c ，D 1 -D 4 Each independently selected from CR d The method comprises the steps of carrying out a first treatment on the surface of the The R is a 、R b 、R c And R is d Identical or at each occurrenceDifferently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
And said R is a 、R b 、R c And R is d Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 6 to 20 carbon atomsSubstituted or unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Adjacent substituents R a 、R b 、R c And R is d Can optionally be linked to form a ring;
preferably, said R a 、R b 、R c And R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, and combinations thereof;
and said R is a 、R b 、R c And R is d Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms Substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, cyano groups, and combinations thereof;
more preferably, the R a 、R b 、R c And R is d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, cyano, and combinations thereof;
and said R is a 、R b 、R c And R is d Is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof.
7. The metal complex according to claim 3, wherein in the formulae 2 to 21, B 1 -B n At least one of which is selected, identically or differently, at each occurrence, from CR b The B is n Corresponds to the B 1 -B 4 The number of which is the largest in any one of formulas 2 to 21; and said R is b And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, cyano,hydroxy, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, and combinations thereof;
Adjacent substituents R b Can optionally be linked to form a ring;
preferably, in the formulas 2, 3, 5 to 12, 16 and 18 to 21, B 2 And/or B 3 Is selected from CR, identically or differently at each occurrence b The method comprises the steps of carrying out a first treatment on the surface of the In the formulas 4, 13 to 15 and 17, B 1 And/or B 2 Is selected from CR, identically or differently at each occurrence b ；
More preferably, the R b And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluoro, cyano, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, epoxyhexyl, norbornyl, adamantyl, trimethylsilyl, trimethylgermanium, phenyl, pyridinyl, triazinyl, trifluoromethyl, methoxy, methylthio, N-dimethylamino, furanyl, thienyl, and combinations thereof.
8. The metal complex as claimed in claim 3, wherein, in the formulae 2 to 20, C 1 And/or C 2 Is selected from CR, identically or differently at each occurrence c ；
And saidR c And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, and combinations thereof;
Preferably, said R c And is selected identically or differently on each occurrence from the group consisting of: deuterium, cyano, fluorine, trifluoromethyl, methyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, trimethylsilyl, trimethylgermanium, phenyl, pyridinyl, triazinyl, and combinations thereof.
9. The metal complex according to claim 3, wherein, in the formulae 2 to 21, A 1 -A n At least one of them is selected from CR a The method comprises the steps of carrying out a first treatment on the surface of the The A is n Corresponds to the A 1 -A 5 The number of which is the largest in any one of formulas 2 to 21; and/or, in the formulas 2 to 21, D 1 -D n At least one of them is selected from CR d The D is n Corresponds to the D 1 -D 4 The number of which is the largest in any one of formulas 2 to 21; the R is a 、R d And is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted silyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms Arylsilyl groups of 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups of 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups of 6-20 carbon atoms, substituted or unsubstituted amino groups of 0-20 carbon atoms, cyano groups, and combinations thereof;
preferably, in the formulas 2 to 14 and 18 to 21, a 1- A 3 At least one of which is selected, identically or differently, at each occurrence, from CR a The method comprises the steps of carrying out a first treatment on the surface of the In the formulae 15 to 17, A 1 Selected from CR a The method comprises the steps of carrying out a first treatment on the surface of the In the formulas 2 to 17 and 19 to 21, D 1 And/or D 2 Selected from CR d ；
More preferably, the R a 、R d And is selected identically or differently on each occurrence from the group consisting of: deuterium, fluoro, cyano, trifluoromethyl, methyl, isopropyl, isobutyl, t-butyl, neopentyl, cyclopentyl, cyclopentylmethylene, cyclohexyl, trimethylsilyl, trimethylgermanium, phenyl, pyridinyl, triazinyl, and combinations thereof.
10. The metal complex of claim 1, wherein L a And is selected identically or differently on each occurrence from the group consisting of:
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wherein, optionally, the L a1 To L a666 Hydrogen in the structure can be partially or fully replaced by deuterium.
11. The metal complex according to claim 1, wherein the metal complex has a structure of M (L a ) m (L b ) n (L c ) q Is of the general formula (I);
wherein the metal M is selected from metals with relative atomic mass greater than 40; l (L) a 、L b And L c A first ligand, a second ligand and a third ligand coordinated to the metal M, respectively; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M; when m is equal to 2 or 3, a plurality of L a May be the same or different; when n is equal to 2, 2L b May be the same or different; when q is equal to 2, 2L c May be the same or different;
L a 、L b and L c Can optionally be linked to form a multidentate ligand;
L b and L c And is selected identically or differently on each occurrence from the group consisting of:
wherein,
R i 、R ii and R is iii Each occurrence, identically or differently, represents mono-substituted, poly-substituted or unsubstituted;
X a the same or different at each occurrenceSelected from the group consisting of: o, S, se, NR N1 And CR (CR) C1 R C2 ；
X b And X c And is selected identically or differently on each occurrence from the group consisting of: o, S, se and NR N2 ；
R i 、R ii 、R iii 、R N1 、R N2 、R C1 And R is C2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Adjacent substituents R i 、R ii 、R iii 、R N1 、R N2 、R C1 And R is C2 Can optionally be linked to form a ring.
12. The metal complex of claim 11, wherein the metal M is selected from Ir, rh, re, os, pt, au or Cu; preferably, the metal M is selected from Ir, pt or Os; more preferably, the metal M is Ir.
13. The metal complex of claim 11, wherein L b Each occurrence is identically or differently selected from the following structures:
wherein R is 1 –R 7 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Preferably, wherein R 1 -R 3 At least one or two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 1 to 20 carbon atoms, or combinations thereof; and/or R 4 -R 6 At least one or both of which are identically or differently selected at each occurrence from substituted or unsubstitutedSubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof;
more preferably, wherein R 1 -R 3 At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 2 to 20 carbon atoms, or combinations thereof; and/or R 4 -R 6 At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 2 to 20 carbon atoms, or combinations thereof.
14. The metal complex of claim 11, wherein L b And is selected identically or differently on each occurrence from the group consisting of:
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wherein L is c And is selected identically or differently on each occurrence from the group consisting of:
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15. the metal complex according to claim 14, wherein the metal complex is an Ir complex and has a structure as described in Ir (L a )(L b )(L c )、Ir(L a ) 2 (L b )、Ir(L a ) 2 (L c ) And Ir (L) a )(L c ) 2 Any of the structures shown; when the metal complex has Ir (L) a )(L b )(L c ) In the structure of (2), the L a Selected from the group consisting of L a1 To L a666 Any one of the group consisting of the L b Selected from the group consisting of L b1 To L b322 Any one of the group consisting of the L c Selected from the group consisting of L c1 To L c231 Any one of the group consisting of; when the metal complex has Ir (L) a ) 2 (L b ) In the structure of (2), the L a Is selected identically or differently on each occurrence from the group consisting of L a1 To L a666 Either or both of the group consisting of, L b Selected from the group consisting of L b1 To L b322 Any one of the group consisting of; when the metal complex has Ir (L) a ) 2 (L c ) In the structure of (2), the L a Is selected identically or differently on each occurrence from the group consisting of L a1 To L a666 Either or both of the group consisting of, L c Selected from the group consisting of L c1 To L c231 Any one of the group consisting of; when the metal complex has Ir (L) a )(L c ) 2 In the structure of (2), the L a Selected from the group consisting of L a1 To L a666 Any one of the group consisting of the L c Is selected identically or differently on each occurrence from the group consisting of L c1 To L c231 Either or both of the group consisting of;
preferably, the metal complex is selected from the group consisting of compounds 1 to 433, the compounds 1 to 433 having Ir (L a ) 2 (L b ) Wherein two L a Identical, L a And L b Respectively correspond to structures selected from the list of:
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16. an electroluminescent device, comprising:
an anode is provided with a cathode,
a cathode electrode, which is arranged on the surface of the cathode,
and an organic layer disposed between the anode and cathode, wherein the organic layer comprises the metal complex of any one of claims 1-15.
17. The electroluminescent device of claim 16 wherein the organic layer is a light emitting layer and the metal complex is a light emitting material.
18. An electroluminescent device as claimed in claim 16 or 17 wherein the electroluminescent device emits red or white light.
19. The electroluminescent device of claim 17 wherein the light emitting layer further comprises at least one host material;
preferably, the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
20. A compound composition comprising the metal complex of any one of claims 1-15.
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| CN202211206728.0A CN117843687A (en) | 2022-09-30 | 2022-09-30 | Luminescent material with multi-ring ligand |
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| CN202211206728.0A CN117843687A (en) | 2022-09-30 | 2022-09-30 | Luminescent material with multi-ring ligand |
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