CN117567517A - Organic electroluminescent material and device thereof - Google Patents
Organic electroluminescent material and device thereof Download PDFInfo
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- CN117567517A CN117567517A CN202210914485.XA CN202210914485A CN117567517A CN 117567517 A CN117567517 A CN 117567517A CN 202210914485 A CN202210914485 A CN 202210914485A CN 117567517 A CN117567517 A CN 117567517A
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- 239000000463 material Substances 0.000 title abstract description 48
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 72
- 239000003446 ligand Substances 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 327
- -1 alkyl germanium Chemical compound 0.000 claims description 145
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 239000010410 layer Substances 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 50
- 229910052751 metal Inorganic materials 0.000 claims description 44
- 239000002184 metal Substances 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000006413 ring segment Chemical group 0.000 claims description 37
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 32
- 229910052805 deuterium Inorganic materials 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 14
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 229910052732 germanium Inorganic materials 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000005580 triphenylene group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical group C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-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
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical group C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 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
- 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
- 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 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical group C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002739 metals Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 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
- WLKSSWJSFRCZKL-UHFFFAOYSA-N trimethylgermanium Chemical compound C[Ge](C)C WLKSSWJSFRCZKL-UHFFFAOYSA-N 0.000 claims description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005577 anthracene group Chemical group 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
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000003111 delayed effect Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000005538 encapsulation Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Chemical group 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
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- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000002993 cycloalkylene group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
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- 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
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- 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
- 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
- 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
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 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
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- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000295 emission spectrum 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
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- 239000007943 implant Substances 0.000 description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- DBVXXBTUAZSUAY-UHFFFAOYSA-N tert-butyl(dimethyl)germanium Chemical group C[Ge](C)C(C)(C)C DBVXXBTUAZSUAY-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical group CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- UMRPCNGKANTZSN-UHFFFAOYSA-N tributylgermanium Chemical group CCCC[Ge](CCCC)CCCC UMRPCNGKANTZSN-UHFFFAOYSA-N 0.000 description 1
- ISEIIPDWJVGTQS-UHFFFAOYSA-N tributylsilicon Chemical group CCCC[Si](CCCC)CCCC ISEIIPDWJVGTQS-UHFFFAOYSA-N 0.000 description 1
- YMSWJBZPRYKQHJ-UHFFFAOYSA-N triethylgermanium Chemical group CC[Ge](CC)CC YMSWJBZPRYKQHJ-UHFFFAOYSA-N 0.000 description 1
- QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical group CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
- SLAJUCLVZORTHN-UHFFFAOYSA-N triphenylgermanium Chemical group C1=CC=CC=C1[Ge](C=1C=CC=CC=1)C1=CC=CC=C1 SLAJUCLVZORTHN-UHFFFAOYSA-N 0.000 description 1
- VCQDQISTTHQOPS-UHFFFAOYSA-N tripropylgermanium Chemical group CCC[Ge](CCC)CCC VCQDQISTTHQOPS-UHFFFAOYSA-N 0.000 description 1
- MMYRBBZVCDXGHG-UHFFFAOYSA-N tripropylsilicon Chemical group CCC[Si](CCC)CCC MMYRBBZVCDXGHG-UHFFFAOYSA-N 0.000 description 1
- TYCHBGWSCCIDHZ-UHFFFAOYSA-N tritert-butylgermanium Chemical group CC(C)(C)[Ge](C(C)(C)C)C(C)(C)C TYCHBGWSCCIDHZ-UHFFFAOYSA-N 0.000 description 1
- STDLEZMOAXZZNH-UHFFFAOYSA-N tritert-butylsilicon Chemical group CC(C)(C)[Si](C(C)(C)C)C(C)(C)C STDLEZMOAXZZNH-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
An organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material is L containing the structure of formula 1 a The metal complex of the ligand can obtain very excellent device performance when being applied to an electroluminescent device, for example, the half-peak width is reduced, the current efficiency, the power efficiency and the external quantum efficiency are improved, the performance of various aspects of the device can be comprehensively improved, and the comprehensive performance of the device is greatly improved. Also disclosed are an organic electroluminescent device comprising the metal complex and a composition comprising the metal complex.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a L comprising the structure of formula 1 a Metal complex of ligand, organic electroluminescent device comprising the same, and compound combination comprising the sameAnd (3) an object.
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 invention of Tang and EBXvan Slyke 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.
CN113717230a discloses a composition comprising the following L A Metal complex of (a):wherein A and B are each a fused heterocyclic or carbocyclic ring comprising three or more 5-and/or six-membered rings, and at least one of these rings is a 5-membered ring. Further disclosed are metal complexes of the structure: />The application discloses the effect of multiple (more than three) condensed ring structure ligands on the spectrum and half-width of the metal complex as a device of a luminescent material, but does not disclose and teach the effect of having a specific substituent on the dibenzofuran ring and at least two (hetero) aryl substituted ligands on the metal complex and the device thereof.
EP3912983A1 discloses a composition having M (L 1 )n 1 (L 2 )n 1 Metal complexes of the general structure, wherein L 1 Has the following structure:L 2 has the following structure: />L 2 Middle X 1 Selected from silicon or germanium. Further disclosed are metal complexes of the structure: />Etc. Meanwhile, about compound 485 +/disclosed by page 202 of the specification of this application>And compound 65As can be seen, the metal complexes containing two aryl substituted ligands on the dibenzofuran ring are even later in performance than the metal complexes of monoaryl substituted ligands. It is known that this application discloses the effect of introducing silicon-based and germanium-based substituents into the ligand on the performance of the metal complex and device, but this application does not disclose or teach that a metal complex having a specific substituent on the dibenzofuran ring while also having at least two (hetero) aryl-substituted ligands can enhance the performance of the device.
Disclosure of Invention
The present invention is directed to a series of comprising 1-knotL of the structure a Metal complexes of ligands to solve at least part of the above problems, wherein L a The ligand has a hexa-penta-hexa-multi fused cyclic structural unit and contains a specific R x And Ar substituents. The novel metal complexes can be applied to electroluminescent devices, can improve the device efficiency, reduce the half-peak width, are beneficial to improving the color saturation of the devices, and achieve the beneficial effect of improving the comprehensive performance of the devices.
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 Wherein L is a Has a structure represented by formula 1:
in the formula (1) of the present invention,
the metal M is selected from metals with relative atomic mass of more than 40;
cy is, identically or differently, selected at each occurrence from an aromatic ring having 6-10 ring atoms, a heteroaromatic ring having 5-10 ring atoms, or a combination thereof;
G 1 、G 2 each occurrence of which is identically or differently selected from a single bond, O or S;
x is selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ' and GeR ' R '; when two R's are present at the same time, the two R's are the same or different;
X 1 -X 8 is selected identically or differently on each occurrence from C, CR x Or N; x is X 1 -X 4 One of which is C and is linked to said Cy, cy may be linked to X by a carbon-carbon bond or a carbon-nitrogen bond 1 、X 2 、X 3 Or X 4 Are connected;
X 1 、X 2 、X 3 or X 4 Selected from N and linked to the metal M by a metal-nitrogen bond, or X 1 、X 2 、X 3 Or X 4 Selected from C through G 2 Is connected with the metal M;
X 1 -X 8 at least one ofEach is CR x And said R x Cyano or fluoro;
X 1 -X 8 at least two of them are CR x And R is x Ar, which Ar is selected, identically or differently, on each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group having from 5 to 30 ring atoms, or a combination thereof;
r represents monosubstituted, polysubstituted or unsubstituted; when a plurality of R are present, the plurality of R are the same or different;
r, R' and R x 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' can optionally be joined to form a ring.
According to another embodiment of the present invention, there is also disclosed an organic electroluminescent device including: an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the metal complex described in the above embodiments.
According to another embodiment of the present invention, there is also disclosed a compound composition comprising the metal complex described in the above embodiment.
The invention discloses a series of L containing a structure of formula 1 a Metal complexes of ligands to solve at least part of the above problems, wherein L a The ligand has a hexa-penta-hexa-multi fused cyclic structural unit and contains a specific R x And Ar substituents. The novel compounds can be applied to electroluminescent devices, can improve the device efficiency, reduce the half-peak width, are beneficial to improving the color saturation of the devices, and achieve the beneficial effect of improving the comprehensive performance of the devices.
Drawings
Fig. 1 is a schematic view of an organic light emitting device that may contain the metal complexes disclosed herein and a compound composition comprising the metal complexes.
Fig. 2 is a schematic view of another organic light emitting device that may contain the metal complexes disclosed herein and a compound composition comprising the metal complexes.
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 -TCNQ's m-MTDATA as disclosed in U.S. patent application publication No. 2003/0239980, 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.
Type E delayed fluorescence features can be found in excitation complex systems or in single compounds. 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, indene, fluorene, pyrene,perylene and azulene, preferably phenyl, biphenylTerphenyl, 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-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 at least two C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. 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, alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, any one or more of which may be substituted with one or at least two groups selected from 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 heteroaryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkoxy having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, aryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 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, multiple substitution is meant to encompass double substitution 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 Wherein L is a Has a structure represented by formula 1:
in the formula (1) of the present invention,
the metal M is selected from metals with relative atomic mass of more than 40;
cy is, identically or differently, selected at each occurrence from an aromatic ring having 6-10 ring atoms, a heteroaromatic ring having 5-10 ring atoms, or a combination thereof;
G 1 、G 2 each occurrence of which is identically or differently selected from a single bond, O or S;
X is selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ' and GeR ' R '; when two R's are present at the same time, the two R's are the same or different;
X 1 -X 8 is selected identically or differently on each occurrence from C, CR x Or N; x is X 1 -X 4 One of which is C and is linked to said Cy, cy may be linked to X by a carbon-carbon bond or a carbon-nitrogen bond 1 、X 2 、X 3 Or X 4 Are connected;
X 1 、X 2 、X 3 or X 4 Selected from N and linked to the metal M by a metal-nitrogen bond, or X 1 、X 2 、X 3 Or X 4 Selected from C through G 2 Is connected with the metal M;
X 1 -X 8 at least one of them is CR x And said R x Cyano or fluoro;
X 1 -X 8 at least two of them are CR x And R is x Ar, which Ar is selected, identically or differently, on each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group having from 5 to 30 ring atoms, or a combination thereof;
r represents monosubstituted, polysubstituted or unsubstituted; when a plurality of R are present, the plurality of R are the same or different;
r, R' and R x 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 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 An 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 alkylsilyl 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' can optionally be joined to form a ring.
Herein, "adjacent substituents R 'can optionally be linked to form a ring" is intended to mean that any one or more of the groups of substituents in which adjacent substituents R' are, for example, joined to form a ring. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein Cy is selected identically or differently on each occurrence from any one of the following structures:
Wherein,
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution; when there are multiple R in any structure, the R are the same or different;
r 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;
Wherein "#" indicates that with G 1 The position of the connection is determined by the position of the connection,representation and X 1 ，X 2 ，X 3 Or X 4 The location of the connection.
According to one embodiment of the invention, wherein the metal M is selected, identically or differently, for each occurrence, from the group consisting of Cu, ag, au, ru, rh, pd, os, ir and Pt.
According to one embodiment of the invention, the metal M is chosen, identically or differently, for each occurrence, from Pt or Ir.
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);
L a 、L b and L c First, second and third ligands coordinated to the metal M, respectively, and L c And said L a Or L b Is the same or different; wherein L is a 、L b And L c Can optionally be linked to form a multidentate ligand;
m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L a The same or different; when n is equal to 2, two L b The same or different; when q is equal to 2, two L c The same or different;
L a and is selected identically or differently on each occurrence from the group consisting of:
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x is selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ' and GeR ' R '; when two R's are present at the same time, the two R's are the same or different;
wherein R is x R represents monosubstituted, polysubstituted or unsubstituted, when a plurality of R's are present simultaneously x When a plurality of R x The same or different. When a plurality of R's are present at the same time, the plurality of R's are the same or different;
wherein R is x Wherein at least two of the Ar's are Ar's, the Ar's are the same or different at each occurrence and are selected from the group consisting of substituted or unsubstituted aromatic rings having from 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic rings having from 5 to 30 ring atoms, or combinations thereof;
R’，R x r 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 heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted cycloalkyl having 7 to 30 carbon atomsSubstituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 20 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, 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;
L b And L c And is selected identically or differently on each occurrence from monoanionic bidentate ligands.
According to one embodiment of the invention, wherein L b And L c A structure shown at each occurrence as being the same or different selected from any one of the group consisting of:
wherein,
X b and is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR N1 ，CR C1 R C2 ；
R a And R is b Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
R a ，R b ，R c ，R N1 ，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 unsubstitutedSubstituted 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 ，R N1 ，R C1 And R is C2 Can optionally be linked to form a ring.
Herein, "adjacent substituent R a ，R b ，R c ，R N1 ，R C1 And R is C2 Can optionally be linked to form a ring ", intended to mean groups of substituents adjacent thereto, e.g. two substituents R a Between two substituents R b Between, substituent R a And R is b Between, substituent R a And R is c Between, substituent R b And R is c Between, substituent R a And R is N1 Between, substituent R b And R is N1 Between, substituent R a And R is C1 Between, substituent R a And R is C2 Between, substituent R b And R is C1 Between, substituent R b And R is C2 Between, and R C1 And R is C2 Between, any of these substituent groupsOne or more may be joined to form a ring. Obviously, these substituents may not all be linked to form a ring. For example, the number of the cells to be processed,r is an adjacent substituent a ，R b Can optionally be linked to form a ring when R a Optionally when linked to form a ring, < >>Can form->Is a structure of (a).
According to one embodiment of the present invention, wherein the metal complex has a structure represented by formula 2:
wherein,
m is selected from 1,2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, a plurality of L a The same or different;
x is selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ' and GR ' R '; when two R's are present at the same time, the two R's are the same or different;
Y 1 -Y 4 Is selected identically or differently on each occurrence from CR or N
X 3 -X 8 Is selected from CR, identically or differently at each occurrence x Or N;
X 3 -X 8 at least one of them is CR x And said R x Cyano or fluoro;
X 3 -X 8 at least two of them are CR X And R is X Ar is selected, identically or differently, for each occurrence from a substituted or unsubstituted aromatic ring having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms, or a group thereofCombining;
R’，R x r 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 R's can optionally be linked to form a ring.
According to one embodiment of the invention, wherein X 1 -X 8 Is selected from CR, identically or differently at each occurrence x 。
According to one embodiment of the invention, wherein X 1 -X 8 Is selected from CR, identically or differently at each occurrence x Or N, and at least one of them is N. For example X 1 -X 8 One of which is selected from N, or X 1 -X 8 Two of which are selected from N.
According to one embodiment of the invention, wherein X 3 -X 8 Is selected from CR, identically or differently at each occurrence x 。
According to one embodiment of the invention, wherein X 3 -X 8 At each occurrenceIdentically or differently selected from CR x Or N, and at least one of them is N. For example X 3 -X 8 One of which is selected from N, or X 3 -X 8 Two of which are selected from N.
According to one embodiment of the invention, wherein Y 1 -Y 4 And is selected, identically or differently, for each occurrence, from CR.
According to one embodiment of the invention, wherein Y 1 -Y 4 Each occurrence is identically or differently selected from CR or N, and at least one of them is N. For example Y 1 -Y 4 One of which is selected from N, or Y 1 -Y 4 Two of which are selected from N.
According to one embodiment of the invention, wherein R x And R is, identically or differently, selected from the group consisting of: hydrogen, 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 alkylgermanium groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein R x And R is, identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted silyl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkyl germanium groups having 3 to 12 carbon atoms, cyano groups, and combinations thereof;
according to one embodiment of the invention, wherein R x And R is, identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl,deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanium, and combinations thereof.
According to an embodiment of the invention, wherein at least one R 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, and combinations thereof.
According to an embodiment of the invention, wherein at least one R 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, and combinations thereof.
According to an embodiment of the invention, wherein at least one R is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-6 ring carbon atoms, substituted or unsubstituted aryl groups having 6-12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein X 3 -X 8 At least one of them is selected from CR x The substituent R x Selected from cyano or fluoro.
According to one embodiment of the invention, wherein X 5 -X 8 At least one of them is selected from CR x The substituent R x Selected from cyano or fluoro.
According to one embodiment of the invention, wherein X 7 Or X 8 Selected from CR x The R is x Selected from cyano or fluoro.
According to one embodiment of the invention, wherein X 7 Selected from CR x The substituent R x Selected from cyano or fluoro.
According to one embodiment of the invention, wherein X 5 -X 8 At least one of them is selected from CR x And said R x Cyano or fluoro; at the same time X 5 -X 8 At least two of them are selected from CR x And said R x Is Ar.
According to one embodiment of the invention, wherein X 5 And X 8 Selected from CR x And said R x Is Ar; or X 6 And X 8 Selected from CR x And said R x Is Ar.
According to one embodiment of the invention, wherein X is selected from O or S.
According to one embodiment of the invention, wherein X is selected from O.
According to one embodiment of the invention, wherein Ar is selected identically or differently on each occurrence from the group consisting of: a substituted or unsubstituted aromatic ring having from 6 to 18 ring atoms, a substituted or unsubstituted heteroaromatic ring having from 5 to 18 ring atoms, or a combination thereof.
According to one embodiment of the invention, wherein Ar is selected identically or differently on each occurrence from the group consisting of substituted or unsubstituted: benzene rings, pyridine rings, pyrimidine rings, naphthalene rings, triazine rings, phenanthrene rings, anthracene rings, silafluorene rings, quinoline rings, isoquinoline rings, benzofuran rings, and dithiophene rings, and difuran rings, benzothiophene rings, indene rings, dibenzofuran rings, dibenzothiophene rings, triphenylene rings, carbazole rings, azacarbazole rings, azadibenzofuran rings, azadibenzothiophene rings, azasilafluorene rings, and combinations thereof.
According to one embodiment of the invention, at least one of Ar is a substituted or unsubstituted carbazole.
According to an embodiment of the invention, wherein Ar is selected identically or differently for each occurrence from the group consisting of Ar1 to Ar204, wherein the specific structure of Ar1 to Ar200 is indicated in claim 11.
According to one embodiment of the invention, wherein hydrogen energy in Ar1-Ar38, ar44, ar47-Ar96, ar99-Ar193 and Ar196-Ar204 is partially or fully substituted with deuterium.
According to one embodiment of the invention, at least one of Ar is a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted azacarbazolyl group.
According to one embodiment of the invention, wherein X 5 Selected from CR x And said R x Is Ar, which is a substituted or unsubstituted carbazole.
According to one embodiment of the invention, wherein R 1 -R 8 At least one or at least two of the substituents selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof; and all of the R 1 -R 4 And/or R 5 -R 8 The sum of the number of carbon atoms of (2) is at least 4.
According to one embodiment of the invention, wherein R 5 -R 8 At least one or at least two selected from the group consisting of substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof, and all of said substituents R 5 -R 8 The sum of the number of carbon atoms of (2) is at least 4.
According to one embodiment of the invention, wherein R 1 -R 4 At least one or at least two selected from the group consisting of substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof, and all of said substituents R 1 -R 4 The sum of the number of carbon atoms of (2) is at least 4.
According to one embodiment of the invention, wherein R 1 -R 4 At least one or at least two alkyl groups 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, or combinations thereof, and all of said substituents R 1 -R 4 Is at least 4; at the same time, R 5 -R 8 At least one or at least two selected from the group consisting of substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, orCombinations thereof, and all of the substituents R 5 -R 8 The sum of the number of carbon atoms of (2) is at least 4.
According to one embodiment of the invention, wherein R 2 Or R is 3 Selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein R 2 Or R is 3 Selected from substituted or unsubstituted alkyl groups of 4 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4 to 20 ring carbon atoms, or combinations thereof.
According to one embodiment of the invention, R' is selected identically or differently on each occurrence from a substituted or unsubstituted alkyl radical having from 1 to 20 carbon atoms or a substituted or unsubstituted cycloalkyl radical having from 3 to 20 ring carbon atoms.
According to one embodiment of the invention, wherein R' is methyl or deuterated methyl.
According to one embodiment of the invention, wherein L a Is selected identically or differently on each occurrence from the group consisting of L a1 To L a3756 A group consisting of said L a1 To L a3756 Is specified in claim 16.
According to one embodiment of the invention, wherein L a1 To L a3756 The hydrogen in (a) can be partially or completely replaced by deuterium.
According to one embodiment of the invention, wherein L b Is selected identically or differently on each occurrence from the group consisting of L b1 To L b151 A group consisting of said L a1 To L b151 Is specified in claim 17.
According to one embodiment of the invention, wherein L b1 To L b151 The hydrogen in (a) can be partially or completely replaced by deuterium.
According to one embodiment of the invention, wherein L c And is selected identically or differently on each occurrence from the group consisting of:
According to one embodiment of the invention, wherein the metal complex has Ir (L a ) 3 、IrL a (L b ) 2 、Ir(L a ) 2 L b 、Ir(L a ) 2 L c 、IrL a (L c ) 2 Or IrL a L b L c Wherein ligand L a Is selected identically or differently on each occurrence from the group consisting of L a1 To L a3756 Any one, any two or any three of the group consisting of ligand L b Is selected identically or differently on each occurrence from the group consisting of L b1 To L b151 Ligand L either or both of the group consisting of c Is selected identically or differently on each occurrence from the group consisting of L c1 To L c50 Either or both of the groups.
According to one embodiment of the invention, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 2584, wherein the specific structure of metal complex 1 to metal complex 2584 is shown in claim 18.
According to an embodiment of the present invention, there is also disclosed an organic electroluminescent device including: an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the metal complex of any of the foregoing embodiments.
According to one embodiment of the present invention, wherein the organic layer containing the metal complex in the organic electroluminescent device is a light emitting layer.
According to one embodiment of the invention, the light emitting layer in the organic electroluminescent device emits green light.
According to one embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further comprises a first host compound.
According to one embodiment of the present invention, the light-emitting layer of the organic electroluminescent device further comprises a first host compound and a second host compound.
According to one embodiment of the invention, the first host compound and/or the second host compound in the electroluminescent device 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, wherein the first host compound has a structure represented by formula X-1 or X-2:
wherein,
L x each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
G is selected identically or differently on each occurrence from C (R g ) 2 、NR g O or S;
v is selected, identically or differently, for each occurrence, from C, CR v Or N;
in formula X-1, T is selected identically or differently for each occurrence from C, CR t Or N;
in formula X-2, T is selected identically or differently for each occurrence from CR t Or N;
R g ，R v and R is t Each occurrence of which is identically or differently selected from the following compositionsIs set of (3): 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 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 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;
Ar 1 The same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, or combinations thereof;
adjacent substituents R g ，R v And R is t Can optionally be linked to form a ring.
In this embodiment, "adjacent substituent R g ，R v And R is t Can optionally be linked to form a ring ", intended to mean groups of substituents adjacent thereto, e.g. two substituents R v Between two substituents R t Between two substituents R g Between, substituent R v And R is t Between, substituent R v And R is g Between, substituent R g And R is t In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein the first host compound has a structure represented by one of formulas X-a to X-p:
wherein,
L x each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
G is selected identically or differently on each occurrence from C (R g ) 2 、NR g O or S;
v is selected, identically or differently, for each occurrence, from CR v Or N;
t is selected identically or differently for each occurrence from CR t Or N;
R g ，R v and R is t 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 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 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 alkylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 0 to 20 carbon atoms, carbonyl, carboxylic acid ester A group, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Ar 1 the same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, or combinations thereof;
adjacent substituents R g ，R v And R is t Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein the first host compound is selected from the group consisting of:
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according to one embodiment of the present invention, wherein the second host compound has a structure represented by formula 5:
wherein,
E 1 -E 6 is selected identically or differently on each occurrence from C, CR e Or N, and E 1 -E 6 At least two of them are N, E 1 -E 6 At least one of which is C and is linked to formula A;
wherein,
q goes out every timeThe same or different at the present time are selected from the group consisting of O, S, se, N, NR Q ，CR Q R Q ，SiR Q R Q ，GeR Q R Q And R is Q C＝CR Q A group of; when two R's are simultaneously present Q When two R Q May be the same or different;
p is 0 or 1; r is 0 or 1;
when Q is selected from N, p is 0, r is 1;
when Q is selected from O, S, se, NR Q ，CR Q R Q ，SiR Q R Q ，GeR Q R Q And R is Q C＝CR Q When the group is formed, p is 1, and r is 0;
L 1 each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Q 1 -Q 8 Is selected identically or differently on each occurrence from C, CR q Or N;
R e ，R Q and R is q 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 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 unsubstitutedOr an 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;
". Times." represents the connection position of formula A with formula 4;
adjacent substituents R e ，R Q ，R q Can optionally be linked into a ring.
Herein, "adjacent substituent R e ，R Q ，R q Can optionally be linked to form a ring ", intended to mean groups of substituents adjacent thereto, e.g. two substituents R e Between two substituents R Q Between two substituents R q Between two substituents R Q And R is q In between, any one or more of these substituent groups may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein the second host compound is selected from the group consisting of:
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according to one embodiment of the invention, the metal complex in the electroluminescent device is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% -30% of the total weight of the luminescent layer.
According to one embodiment of the invention, the metal complex in the electroluminescent device is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 3% -13% of the total weight of the luminescent layer.
According to one embodiment of the present invention, the organic electronic device further includes a hole injection layer, where the hole injection layer may be a single material functional layer, or may be a functional layer including multiple materials, where the multiple materials included are most commonly doped with a p-type conductive doping material in a proportion. Common p-type doping materials are: />
According to another embodiment of the present invention, there is also disclosed a compound composition comprising a metal complex having a specific structure 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 luminescent dopants disclosed herein may be used in combination with a variety of 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.
Examples of materials synthesis
Synthesis example 1: synthesis of Metal Complex 39
In a 100mL three-necked flask, intermediate 1 (2.9 g,10 mmol) was dissolved in 30mL tetrahydrofuran. To the solution of intermediate 1 was added a tetrahydrofuran solution of LDA (15 mmol) under nitrogen protection at 0 ℃, and after keeping the reaction at 0 ℃ for 1 hour, a tetrahydrofuran solution of N-fluorobiphenyl sulfonamide (NFSI, 5g,16 mmol) was added and room temperature was restored. After 1h, the reaction was purified by column chromatography (dichloromethane) to give intermediate 2 (2.6 g,8.5mmol, 85%).
In a 50mL three-necked flask, intermediate 2 (0.9 g,2.9 mmol) was dissolved in 15mL tetrahydrofuran. To the solution of intermediate 2 was added a tetrahydrofuran solution of a mixture of carbazole (1.67 g,10 mmol) and sodium t-butoxide (0.96 g,10 mmol) at 0℃under nitrogen protection, and after 0.5h, the reaction mixture was returned to room temperature, and after 1h, the solvent was removed by spin-drying under reduced pressure, and purified by column chromatography (dichloromethane) to give intermediate 3 (1.2 g,2.0mmol, 69%).
Intermediate 4 (1.4 g,1.6 mmol), intermediate 3 (1.2 g,2.0 mmol) were added sequentially to a mixed solvent of 2-ethoxyethanol (15.0 mL) and DMF (15.0 mL) in a 50mL two-necked flask under nitrogen atmosphere, and the temperature was raised to 100deg.C for 120h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure, and purified by column chromatography (dichloromethane/petroleum ether=1/1) to give metal complex 39 (0.6 g,0.5mmol, 31%). The product was identified as the target product and had a molecular weight of 1212.4.
Synthesis example 2: synthesis of Metal Complex 57
Intermediate 4 (0.66 g,0.8 mmol), intermediate 5 (0.54 g,0.87 mmol) were added sequentially to a mixed solvent of 2-ethoxyethanol (10.0 mL) and DMF (10.0 mL) in a 50mL two-necked flask under nitrogen, and the temperature was raised to 100deg.C for 120h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure, and purified by column chromatography (dichloromethane/petroleum ether=1/1) to give metal complex 57 (0.28 g,0.23mmol, 29%). The product was identified as the target product and had a molecular weight of 1228.5.
Synthesis example 3: synthesis of metal complex 102
Intermediate 4 (0.83 g,1.0 mmol), intermediate 5 (0.53 g,1.0 mmol) were added sequentially to a mixed solvent of 2-ethoxyethanol (10.0 mL) and DMF (10.0 mL) in a 50mL two-necked flask under nitrogen atmosphere, and the temperature was raised to 100deg.C for 120h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure, and purified by column chromatography (dichloromethane/petroleum ether=1/1) to give metal complex 102 (0.2 g,0.17mmol, 17%). The product was identified as the target product and had a molecular weight of 1136.5.
Device example 1
First, a glass substrate having an 80nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was baked in a glove box to remove moisture. The substrate is then mounted on a substrate support and loaded into a vacuum chamber. The organic layer specified below was at a vacuum level of about 10 -8 In the case of the support, vapor deposition was sequentially performed on the ITO anode by thermal vacuum vapor deposition at a rate of 0.2 to 2 Angstrom/sec. The compound HI is used as a Hole Injection Layer (HIL). The compound HT serves as a Hole Transport Layer (HTL). The compound PH-23 acts as an Electron Blocking Layer (EBL). The inventive metal complex 57 is then co-deposited with compound PH-23 and compound H-40 for use as an emissive layer (EML). On EML, compound H-2 acts as a Hole Blocking Layer (HBL). On the HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1nm was evaporated as an electron injection layer, and 120nm of aluminum was evaporated as a cathode. The device is then assembledTransferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.
Device example 2
The embodiment of device example 2 is the same as device example 1 except that the metal complex 57 of the present invention is replaced with a metal complex 102 in the light emitting layer (EML).
Device comparative example 1
The embodiment of device comparative example 1 is the same as device example 1 except that the compound GD1 is used in the light-emitting layer (EML) instead of the metal complex 57 of the present invention.
The detailed device layer structure and thickness are shown in the following table. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
TABLE 1 device architectures of examples 1-2 and comparative example 1
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The material structure used in the device is as follows:
the IVL characteristics of the device were measured. At 10mA/cm 2 The CIE data of the device, the maximum emission wavelength lambda, are measured max Half width of peak (FWHM), driving voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE). These data are recorded and shown in table 2.
Table 2 device data for example 1 and comparative example 1
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As can be seen from the data in table 2: example 1 compared with comparative example 1, the metal complexes 57 and GD1 were used as light-emitting materials, respectively, and the metal complexes 57 and GD1 were different only in that the metal complexes 57 further had one carbazole substituent on the basis of GD1, the half-width of example 1 was narrowed by 8.7nm, and the ce, pe, eqe were improved by 15.1%,13.1%,13.3%, respectively, and the driving voltages were comparable. Similarly, example 2 differs from comparative example 1 only in that the metal complex 102 further has a phenyl substituent on the basis of GD1, the half-width of example 2 is narrowed by 9.0nm, and ce, pe, eqe are increased by 8.1%,7.1%,6.3%, respectively, and the driving voltages are equivalent.
The above results indicate that the present application has specific Ar and R x Compared with the metal complex which is not used in the organic electroluminescent device, the metal complex can obviously improve the device efficiency (CE, PE and EQE), obviously reduce the half-peak width, be beneficial to improving the color saturation of the device and achieve the beneficial effect of greatly improving the comprehensive performance of the device.
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 (23)
1. A metal complex comprising a metal M, and a ligand L coordinated to the metal M a Wherein L is a Has a structure represented by formula 1:
in the formula (1) of the present invention,
the metal M is selected from metals with relative atomic mass of more than 40;
cy is, identically or differently, selected at each occurrence from an aromatic ring having 6-10 ring atoms, a heteroaromatic ring having 5-10 ring atoms, or a combination thereof;
G 1 、G 2 each occurrence of which is identically or differently selected from a single bond, O or S;
X is selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ' and GeR ' R '; when two R's are present at the same time, the two R's are the same or different;
X 1 -X 8 is selected identically or differently on each occurrence from C, CR x Or N; x is X 1 -X 4 One of which is C and is linked to said Cy, cy may be linked to X by a carbon-carbon bond or a carbon-nitrogen bond 1 、X 2 、X 3 Or X 4 Are connected;
X 1 、X 2 、X 3 or X 4 Selected from N and linked to the metal M by a metal-nitrogen bond, or X 1 、X 2 、X 3 Or X 4 Selected from C through G 2 Is connected with the metal M;
X 1 -X 8 at least one of them is CR x And said R x Cyano or fluoro;
X 1 -X 8 at least two of them are CR x And R is x Ar, which Ar is selected, identically or differently, on each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 ring atoms, a substituted or unsubstituted heteroaryl group having from 5 to 30 ring atoms, or a combination thereof;
r represents monosubstituted, polysubstituted or unsubstituted; when a plurality of R are present, the plurality of R are the same or different;
r, R' and R x 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 alkyl having 1 to 20 carbon atoms A heteroatom, a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, 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 alkylgermanium group having 6 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 mercapto group, a sulfonyl group, a phosphono group, and combinations thereof;
adjacent substituents R' can optionally be joined to form a ring.
2. The metal complex of claim 1, wherein Cy is selected identically or differently for each occurrence from any one of the following structures:
Wherein,
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution; when a plurality of R are present in any structure, the plurality of R are the same or different;
r 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;
Wherein "#" indicates that with G 1 The position of the connection is determined by the position of the connection,representation and X 1 ，X 2 ，X 3 Or X 4 The location of the connection.
3. The metal complex of claim 1, wherein the metal M is selected, identically or differently, at each occurrence, from the group consisting of Cu, ag, au, ru, rh, pd, os, ir and Pt;
preferably, the metal M is selected, identically or differently, for each occurrence, from Pt or Ir.
4. A metal complex as claimed in any one of claims 1 to 3, wherein the metal complex has a structure of M (L a ) m (L b ) n (L c ) q Is of the general formula (I);
L a 、L b and L c First, second and third ligands coordinated to the metal M, respectively, and L c And said L a Or L b Is the same or different; wherein L is a 、L b And L c Can optionally be linked to form a multidentate ligand;
m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L a The same or different; when n is equal to 2, two L b The same or different; when q is equal to 2, two L c The same or different;
L b and L c A structure shown at each occurrence as being the same or different selected from any one of the group consisting of:
wherein,
X b and is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR N1 ，CR C1 R C2 ；
R a And R is b Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
R a ，R b ，R c ，R N1 ，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 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 aryl having 2 to 20 carbon atomsSubstituted 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 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, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Adjacent substituents R a ，R b ，R c ，R N1 ，R C1 And R is C2 Can optionally be linked to form a ring.
5. The metal complex according to claim 4, wherein the metal complex has a structure represented by formula 2:
wherein,
m is selected from 1,2 or 3; when m is selected from 1, two L b The same or different; when m is selected from 2 or 3, a plurality of L a The same or different;
x is selected from the group consisting of O, S, se, NR ', CR ' R ', siR ' R ' and GeR ' R '; when two R's are present at the same time, the two R's are the same or different;
Y 1 -Y 4 each occurrence is selected identically or differently from CR or N;
X 3 -X 8 is selected from CR, identically or differently at each occurrence x Or N;
X 3 -X 8 at least one of them is CR x And said R x Cyano or fluoro;
X 3 -X 8 at least two of them are CR X And R is x Ar, which Ar is selected, identically or differently, on each occurrence, from a substituted or unsubstituted aromatic ring having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;
R’，R x ，R，R 1 -R 8 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 R's can optionally be linked to form a ring.
6. The metal complex according to claim 5, wherein X 3 -X 8 Is selected from CR, identically or differently at each occurrence x And/or Y 1 -Y 4 Selected identically or differently for each occurrence from CR;
R x and R is, identically or differently, 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, takenSubstituted 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, cyano groups, and combinations thereof;
preferably, R x And R is, identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted silyl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkyl germanium groups having 3 to 12 carbon atoms, cyano groups, and combinations thereof;
More preferably, R x And R is, identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, neopentyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated neopentyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermanium, and combinations thereof.
7. The metal complex according to claim 5, wherein Y 1 -Y 4 Each occurrence is identical or different CR or N, and Y 1 -Y 4 At least one of which is selected from CR, and said R 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, and combinations thereof;
preferably, said R is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-6 ring carbon atoms, substituted or unsubstituted aryl groups having 6-12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-12 carbon atoms, and combinations thereof.
8. The metal complex according to claim 5, wherein X 3 -X 8 At least one of which is N, and/or Y 1 -Y 4 At least one of which is N.
9. The metal complex as claimed in any one of claims 1 to 5, wherein X is selected from O or S; preferably, X is selected from O.
10. The metal complex of any one of claims 1-5, wherein Ar is selected identically or differently on each occurrence from the group consisting of: a substituted or unsubstituted aromatic ring having from 6 to 18 ring atoms, a substituted or unsubstituted heteroaromatic ring having from 5 to 18 ring atoms, or a combination thereof;
preferably, ar is selected identically or differently on each occurrence from the group consisting of substituted or unsubstituted: benzene rings, pyridine rings, pyrimidine rings, naphthalene rings, triazine rings, phenanthrene rings, anthracene rings, silafluorene rings, quinoline rings, isoquinoline rings, benzofuran rings, and dithiophene rings, and difuran rings, benzothiophene rings, indene rings, dibenzofuran rings, dibenzothiophene rings, triphenylene rings, carbazole rings, azacarbazole rings, azadibenzofuran rings, azadibenzothiophene rings, azasilafluorene rings, and combinations thereof.
11. The metal complex of any one of claims 1-5, wherein Ar is selected identically or differently on each occurrence from the group consisting of:
Optionally, hydrogen energy in Ar1-Ar38, ar44, ar47-Ar96, ar99-Ar193, and Ar196-Ar204 described above is partially or fully substituted with deuterium.
12. The metal complex as defined in claim 1 or 5, wherein X 5 -X 8 At least one of them is selected from CR x And said R x Cyano or fluoro;
preferably X 7 Or X 8 Selected from CR x And said R x Cyano or fluoro;
more preferably X 7 Selected from CR x And said R x Is cyano or fluoro.
13. The metal complex as defined in claim 1 or 5, wherein X 5 -X 8 At least two of them are selected from CR x And said R x Is Ar;
preferably X 5 And X 8 Selected from CR x And said R x Is Ar; or X 6 And X 8 Selected from CR x And said R x Is Ar.
14. The metal complex of any one of claims 1-13, wherein at least one of Ar is a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted azacarbazolyl group;
preferably X 5 Selected from CR x And said R x Is Ar, which is a substituted or unsubstituted carbazolyl group.
15. As claimed in claim 5The metal complex, wherein R 1 -R 8 At least one or at least two of the substituents selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof; and all of the R 1 -R 4 And/or R 5 -R 8 Is at least 4;
preferably, R 1 -R 4 At least one or at least two alkyl groups 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, or combinations thereof, and all of said substituents R 1 -R 4 Is at least 4; and/or R 5 -R 8 At least one or at least two selected from the group consisting of substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof, and all of said substituents R 5 -R 8 The sum of the number of carbon atoms of (2) is at least 4.
16. The metal complex of claim 11, wherein L a Is selected identically or differently on each occurrence from the group consisting of L a1 To L a3756 Group of L a1 To L a3756 The specific structure of (2) is as follows:
the following L a1 To L a3524 The structure is as follows:therein X, R Y2 -R Y3 、R X4 -R X8 An atom or group selected from the following table:
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in the above table, cy1 to Cy9 have the following structure:
wherein, "#" indicates the position of the connection to M,representing the connection location to the DBX;
L a3525 to L a3557 The structure is as follows:therein X, R X4 -R X8 An atom or group selected from the following table:
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the following L a3558 To L a3590 The structure is as follows:therein X, R X4 -R X8 An atom or group selected from the following table:
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The following are described belowL a3591 To L a3623 The structure is as follows:therein X, R X4 -R X8 An atom or group selected from the following table:
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the following L a3624 To L a3656 The structure is as follows:therein X, R X4 -R X8 An atom or group selected from the following table: />
L a3657 To L a3670 The ligand structure of (a) is as follows:
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optionally, L a1 To L a3756 The hydrogen atoms of (a) can be partially or fully substituted with deuterium.
17. The metal complex as defined in claim 5 or 16, wherein L b And is selected identically or differently on each occurrence from the group consisting of:
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optionally, L b1 To L b151 The hydrogen in (a) can be partially or completely replaced by deuterium.
18. The metal complex of claim 1, wherein the metal complex is selected identically or differently at each occurrence from the group consisting of metal complex 1 to metal complex 2584:
wherein metal complex 1 to metal complex 2576 have IrL a (L b ) 2 Of the general structure of (1), wherein two L b The same or different，L a And L b Respectively correspond to the structures in the following table:
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the metal complexes 2577 to 2584 have Ir (L a ) 2 L b Of the general structure of (1), wherein two L a Identical or different, L a And L b A structure selected from the following table:
19. an organic 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 the cathode, at least one of the organic layers comprising the metal complex of any one of claims 1-18.
20. The organic electroluminescent device of claim 19, wherein the organic layer comprising the metal complex is a light emitting layer.
21. The organic electroluminescent device of claim 20, wherein the light-emitting layer further comprises a first host compound;
preferably, the light emitting layer further comprises a second host compound;
more preferably, the first host compound and/or the second host compound 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.
22. The organic electroluminescent device of claim 21, wherein the metal complex is doped in the first and second host compounds, the metal complex accounting for 1% -30% of the total weight of the light emitting layer;
preferably, the metal complex accounts for 3% -13% of the total weight of the luminescent layer.
23. A compound composition comprising the metal complex of any one of claims 1-18.
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