CN117024481A - Organic electroluminescent material and device thereof - Google Patents
Organic electroluminescent material and device thereof Download PDFInfo
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- CN117024481A CN117024481A CN202210464091.9A CN202210464091A CN117024481A CN 117024481 A CN117024481 A CN 117024481A CN 202210464091 A CN202210464091 A CN 202210464091A CN 117024481 A CN117024481 A CN 117024481A
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- 239000000463 material Substances 0.000 title abstract description 50
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 88
- 239000003446 ligand Substances 0.000 claims abstract description 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 229910052751 metal Inorganic materials 0.000 claims abstract description 37
- 239000002184 metal Substances 0.000 claims abstract description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 445
- -1 alkyl germanium Chemical compound 0.000 claims description 151
- 125000001424 substituent group Chemical group 0.000 claims description 146
- 239000010410 layer Substances 0.000 claims description 82
- 125000003118 aryl group Chemical group 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims description 69
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 59
- 229910052805 deuterium Inorganic materials 0.000 claims description 59
- 125000006413 ring segment Chemical group 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 238000006467 substitution reaction Methods 0.000 claims description 29
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 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 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 12
- 229910052732 germanium Inorganic materials 0.000 claims description 12
- 125000005549 heteroarylene group Chemical group 0.000 claims description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
- 229910052796 boron Inorganic materials 0.000 claims description 9
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 229910005965 SO 2 Inorganic materials 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 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 7
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002462 isocyano group Chemical group *[N+]#[C-] 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
- 238000000034 method Methods 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
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 229910052770 Uranium Inorganic materials 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- 150000002739 metals Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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 class C[Ge](C)C WLKSSWJSFRCZKL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical class [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 2
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical class [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 abstract description 4
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000003111 delayed effect Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 230000036961 partial effect Effects 0.000 description 6
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000005104 aryl silyl group Chemical group 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000005538 encapsulation Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- 229940093475 2-ethoxyethanol Drugs 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 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
- 238000004440 column chromatography Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
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- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
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- 239000002019 doping agent Substances 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
- 230000005669 field effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 150000002290 germanium Chemical class 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 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
- 230000008569 process Effects 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
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- 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
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C07F15/0086—Platinum compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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Abstract
An organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material is L containing the structure of formula 1A a Ligand and L of structure 1B b The novel metal complexes of the ligand are applied to the organic electroluminescent device, can provide very excellent device performances, such as half-width, current efficiency, power efficiency, external quantum efficiency and device life, are favorable for obtaining more saturated green luminescence, comprehensively improve the performances of the device in all aspects, and finally greatly improve the comprehensive performance of the device. Also disclosed are an organic electroluminescent device comprising the metal complex and a compound combination comprising the metal complex.
Description
Technical Field
The present invention relates toA compound for use in an organic electronic device, such as an organic light emitting device. More particularly, it relates to a L comprising the structure of formula 1A a Ligand and L of structure 1B b Metal complexes of ligands, organic electroluminescent devices comprising the same, and compound compositions comprising the same.
Background
Organic electronic devices include, but are not limited to, the following: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLEDs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.
In 1987, tang and Van Slyke of Isomandah reported a double-layered organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters,1987,51 (12): 913-915). Once biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). Most advanced OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Because OLEDs are self-emitting solid state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in flexible substrate fabrication.
OLEDs can be divided into three different types according to their light emission mechanism. The OLED of the Tang and van Slyke invention is a fluorescent OLED. It uses only singlet light emission. The triplet states generated in the device are wasted through non-radiative decay channels. Thus, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation prevents commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs using triplet emission from heavy metals containing complexes as emitters. Thus, both singlet and triplet states can be harvested, achieving a 100% IQE. Because of its high efficiency, the discovery and development of phosphorescent OLEDs has contributed directly to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency by Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons by reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymeric OLEDs depending on the form of the materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of the small molecules can be large as long as they have a precise structure. Dendrimers with a defined structure are considered small molecules. Polymeric OLEDs include conjugated polymers and non-conjugated polymers having pendant luminescent groups. Small molecule OLEDs can become polymeric OLEDs if post-polymerization occurs during fabrication.
Various methods of OLED fabrication exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymeric OLEDs are manufactured by solution processes such as spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be fabricated by solution processes if the material can be dissolved or dispersed in a solvent.
The emission color of an OLED can be achieved by the structural design of the luminescent material. The OLED may include a light emitting layer or layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full color OLED displays typically employ a mixing strategy using blue fluorescent and phosphorescent yellow, or red and green. Currently, a rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
Metal complexes comprising ligands of the following structure are disclosed in US20220089624 A1:wherein R is 1 -R 3 At least one of which has the following structure: />The following structure is further disclosed:the application does not disclose or teach the present application for L comprising the structure of formula 1A a Ligand and L of structure 1B b Metal complexes of ligands.
An iridium complex having the following structure is disclosed in US20140306205 A1:wherein A is 1 -D 1 The four rings are 5-membered or 6-membered; and further discloses that the metal complex has the following structure:wherein G is selected from carbazole, fluorene, dibenzothiophene, dibenzofuran, etc., and further discloses iridium complex +.>The application does not disclose or teach the present application for L comprising the structure of formula 1A a Ligand and L of structure 1B b Metal complexes of ligands.
Disclosure of Invention
The present application aims to provide a series of L comprising the structure of 1A a Ligand and L of structure 1B b 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, L b The ligand has a substituent of formula 2 in a specific position. The novel metal complexes can be applied to electroluminescent devices to obtain very excellent device performances such as half-width, current efficiency, power efficiency, external quantum efficiency and device life, and are beneficial to obtaining The device emits more saturated green light, comprehensively improves the performance of the device in all aspects, and finally greatly improves the comprehensive performance of the device.
According to one embodiment of the present invention, a metal complex is disclosed having M (L a ) m (L b ) n (L c ) q Is represented by the general formula (I),
wherein,
L a 、L b and L c A first ligand, a second ligand and a third ligand which are coordinated with the metal M, respectively, and the third ligand L c Capable of binding to the first ligand L a Or a second ligand L b Selected from the same or different structures; wherein L is a 、L b And L c Can optionally be linked to form a multidentate ligand;
the metal M is selected from metals with relative atomic mass of more than 40;
m is selected from 1 or 2; n is selected from 1 or 2; q is selected from 0 or 1; when m=2, two L a The same or different; when n=2, two L b The same or different;
L a each occurrence of which is the same or different having the structure of formula 1A; l (L) b Each occurrence of which is the same or different having the structure of formula 1B;
wherein,
the ring Cy is, identically or differently, selected at each occurrence from an aromatic ring having 6-30 ring atoms, a heteroaromatic ring having 5-30 ring atoms, or a combination thereof;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
z is selected from the group consisting of O, S, se, CR 'R', siR 'R' and GeR 'R'; when two R's are present simultaneously, 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; and X is 1 -X 4 One of which is selected from C and is linked to a ring Cy;
X 1 ，X 2 ，X 3 or X 4 Coordination to the metal M via a metal-carbon bond or a metal-nitrogen bond;
a is selected from 0 or 1;
W 1 -W 3 is selected from CR, identically or differently at each occurrence w Or N;
U 1 -U 4 is selected from CR, identically or differently at each occurrence u 、NR u O, S or N, and U 1 -U 4 At most one of which is selected from N;
ar has a structure represented by formula 2:
in formula 2, "" represents the position of attachment of formula 2;
R A and R is B Each occurrence, identically or differently, represents mono-, poly-or unsubstituted;
ring a and ring B are identically or differently selected from carbocycles having 3 to 30 ring atoms, or heterocycles having 3 to 30 ring atoms;
l is selected from the group consisting of: single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", ger" R ", BR", PR ", P (O) R", R "c=cr", substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, and combinations thereof;
R，R’，R”，R x ，R u ，R w ，R A And R is B And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstitutedSubstituted 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 arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 0 to 20 carbon atoms, substituted or unsubstituted aminoyl having 0 to 20 carbon atoms, carbonyl, sulfonyl, cyano, sulfonyl, and combinations thereof;
L c The same or different at each occurrence is selected from monoanionic bidentate ligands;
adjacent substituents R', R x R can optionally be linked to form a ring;
adjacent substituents R ", R A ，R B Can optionally be linked to form a ring;
adjacent substituents R u Can optionally be linked to form a ring;
adjacent substituents R u And R is w Can optionally be linked 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 combination comprising the metal complex described in the above embodiment.
The invention discloses a series of compositions comprising formula 1L of A Structure a Ligand and L of structure 1B b 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, L b The ligand has a substituent of the structure of formula 2 in a specific position. The novel compounds can be applied to electroluminescent devices to obtain very excellent device performances, such as half-peak width, current efficiency, power efficiency, external quantum efficiency and device life, and can comprehensively improve the performances of the devices in various aspects, and finally the comprehensive performances of the devices are greatly improved.
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 m-MTDATA of TCNQ, as disclosed in U.S. patent application publication No. 2003/0230980, incorporated by reference in its entiretyAs disclosed in the number. 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, fluorene, pyrene,perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl,biphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl-yl, 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-quaternion. 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 having M (L a ) m (L b ) n (L c ) q Is represented by the general formula (I),
wherein,
L a 、L b and L c A first ligand, a second ligand and a third ligand which are coordinated with the metal M, respectively, and the third ligand L c Capable of binding to the first ligand L a Or a second ligand L b Selected from the same or different structures; wherein L is a 、L b And L c Can optionally be linked to form a multidentate ligand;
the metal M is selected from metals with relative atomic mass of more than 40;
m is selected from 1 or 2; n is selected from 1 or 2; q is selected from 0 or 1; when m=2, two L a The same or different; when n=2, two L b The same or different;
L a each occurrence of which is the same or different having the structure of formula 1A; l (L) b Each occurrence of which is the same or different having the structure of formula 1B;
wherein,
the ring Cy is, identically or differently, selected at each occurrence from an aromatic ring having 6-30 ring atoms, a heteroaromatic ring having 5-30 ring atoms, or a combination thereof;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
z is selected from the group consisting of O, S, se, CR 'R', siR 'R' and GeR 'R'; when two R's are present simultaneously, 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; and X is 1 -X 4 One of which is selected from C and is linked to a ring Cy;
X 1 ，X 2 ，X 3 or X 4 Coordination to the metal M via a metal-carbon bond or a metal-nitrogen bond;
a is selected from 0 or 1;
W 1 -W 3 is selected from CR, identically or differently at each occurrence w Or N;
U 1 -U 4 is selected from CR, identically or differently at each occurrence u 、NR u O, S or N, and U 1 -U 4 At most one of which is selected from N;
ar has a structure represented by formula 2:
in formula 2, "" represents the position of attachment of formula 2;
R A and R is B Each occurrence, identically or differently, represents mono-, poly-or unsubstituted;
Ring a and ring B are identically or differently selected from carbocycles having 3 to 30 ring atoms, or heterocycles having 3 to 30 ring atoms;
l is selected from the group consisting of: single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", ger" R ", BR", PR ", P (O) R", R "c=cr", substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, and combinations thereof;
R，R’，R”，R x ，R u ，R w ，R A and R is B 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, carbonyl having 0 to 20 carbon atoms, Sulfonyl, phosphino, and combinations thereof;
L c the same or different at each occurrence is selected from monoanionic bidentate ligands;
adjacent substituents R', R x R can optionally be linked to form a ring;
adjacent substituents R ", R A ，R B Can optionally be linked to form a ring;
adjacent substituents R u Can optionally be linked to form a ring;
adjacent substituents R u And R is w Can optionally be linked to form a ring.
Herein, "adjacent substituents R', R x R can optionally be linked to form a ring ", intended to mean groups of substituents adjacent thereto, for example, between two substituents R', between two substituents R x Between, substituents R' and R x Between, substituents R and R x 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.
Herein, "adjacent substituents R", R A ，R B Can optionally be linked to form a ring ", intended to mean groups of substituents adjacent thereto, e.g. between two substituents R", two substituents R A Between two substituents R B Between, substituent R A And R' between, substituent R B And R ", 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.
Herein, "adjacent substituent R u Can optionally be linked to form a ring ", intended to mean any two adjacent substituents R therein u Any one or more of the groups may be joined to form a ring. Obviously, these substituents may not all be linked to form a ring.
Herein, "adjacent substituent R u And R is w Can optionally be linked to form a ring ", intended to mean groups of substituents adjacent thereto, e.gSubstituent R u And R is w 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. For example, when a is selected from 0, and U 3 Selected from CR u ，W 1 Selected from CR w When in use, R is u And said R w Can be linked to form a ring; when a is selected from 1, and U 4 Selected from CR u ，W 1 Selected from CR w When in use, R is u And said R w May be joined to form a ring.
Herein, when a is 0, it means U 4 Is not present, L b The ligand has the following structure:at this time U 1 -U 3 Is selected from CR, identically or differently at each occurrence u 、NR u O, S or N, and U 1 -U 3 At most one of them is selected from N (i.e. U 1 -U 3 One of which is selected from N, or U 1 -U 3 Selected from CR u 、NR u O or S); when a is 1, it indicates U 4 Exist at this time L b The ligand has the following structure: / >At this time U 1 -U 4 Is selected from CR, identically or differently at each occurrence u Or N, and U 1 -U 4 At most one of them is selected from N (i.e. U 1 -U 4 One of which is selected from N, or U 1 -U 4 Selected from CR u )。
Herein, "ring a and ring B are identically or differently selected from carbocycles having 3 to 30 ring atoms, or heterocycles having 3 to 30 ring atoms", which carbocycles and heterocycles may be aromatic or non-aromatic, i.e., carbocycles include aromatic or alicyclic rings, heterocycles include heteroaromatic or heteroalicyclic rings, wherein both of the alicyclic and heteroalicyclic rings may contain at least one unsaturated bond, and at least one or more of the atoms including but not limited to O, S, se, N, si, P, ge and B may be included therein.
According to one embodiment of the invention, adjacent substituents R w Are not connected to form a ring.
According to one embodiment of the invention, wherein the ring Cy is, for each occurrence, identically or differently selected 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;
Adjacent substituents R can optionally be joined to form a ring;
wherein "#" represents a bond to metal MThe position of the joint is that,representation and X 1 ，X 2 ，X 3 Or X 4 The location of the connection.
Herein, "adjacent substituents R can optionally be linked to form a ring" is intended to mean that any one or more of the group consisting of any two adjacent substituents R can 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 L b And is selected, identically or differently, on each occurrence, from the group consisting of:
R u and R is w Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
R u and R is w 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 alkenyl having 3 to 20 carbon atoms Unsubstituted aryl silyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl germanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents R u Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein L c And is selected, identically or differently, on each occurrence, from the group consisting of:
/>
wherein,
R a and R is b Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;
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 ，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 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 aryl 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 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 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. 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 invention, wherein U 1 -U 4 The same or different at each occurrence is selected from CR u 。
According to one embodiment of the invention, wherein U 1 -U 4 Is selected from CR, identically or differently at each occurrence u Or N, and one of them is N.
According to one embodiment of the invention, wherein U 1 -U 3 The same or different at each occurrence is selected from CR u 。
According to one embodiment of the invention, wherein U 1 -U 3 Is selected from CR, identically or differently at each occurrence u Or N, and one of them is N.
According to one embodiment of the invention, wherein W 1 -W 3 Is selected from CR, identically or differently at each occurrence w Or N, and at least one of them is N. For example W 1 -W 3 One of which is selected from N or two of which are selected from N.
According to one embodiment of the invention, wherein W 1 -W 3 The same or different at each occurrence is selected from CR w 。
According to one embodiment of the invention, wherein R u And R is w And is selected identically or differently on each occurrence 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, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein R u And R is w And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, cyanoAnd combinations thereof.
According to one embodiment of the invention, wherein R u And R is w And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R u And R is w And is selected identically or differently on each occurrence 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, and combinations thereof.
According to one embodiment of the invention, wherein the metal complex has Ir (L a ) m (L b ) 3-m And is represented by formula 3:
wherein,
m is selected from 1,2; when m=1, two L b The same or different; when m=2, two L a The same or different;
z is selected from the group consisting of O, S, se, 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 is selected from CR, identically or differently at each occurrence y Or N;
X 3 -X 8 is selected from CR, identically or differently at each occurrence x Or N;
ar has a structure represented by formula 2:
wherein, in the formula 2,
R A and R is B Each occurrence, identically or differently, represents mono-, poly-or unsubstituted;
ring a and ring B are identically or differently selected from carbocycles having 3 to 30 ring atoms, or heterocycles having 3 to 30 ring atoms;
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", ger" R ", BR", PR ", P (O) R", R "c=cr", 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 heterocyclylene group having 3 to 20 ring atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R’，R”，R x ，R y ，R 1 -R 7 ，R A And R is B 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 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 alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted germanium having 6 to 20 carbon atoms, substituted or unsubstituted germanium having 0 to 20 carbon atomsAmino groups, 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;
"onium" represents the attachment position of formula 2;
adjacent substituents R', R x ，R y Can optionally be linked to form a ring;
adjacent substituents R ", R A ，R B Can optionally be linked to form a ring;
adjacent substituents R 4 -R 7 Can optionally be linked to form a ring.
Herein, "adjacent substituents R', R x ，R y Can optionally be linked to form a ring ", is intended to mean groups of substituents adjacent thereto, for example, between two substituents R', two substituents R y Between two substituents R x Between, substituents R' and R x Between, substituent R y And R is x 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.
Herein, "adjacent R 4 -R 7 Can optionally be linked to form a ring "is intended to mean R 4 -R 7 Any one or more of the groups of any two adjacent substituents 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 a is selected from 1.
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 3 -X 8 Two of which are selected from N.
According to one embodiment of the inventionWherein X is 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 Is selected from CR, identically or differently at each occurrence 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 Is selected from CR, identically or differently at each occurrence y 。
According to one embodiment of the invention, wherein Y 1 -Y 4 Is selected from CR, identically or differently at each occurrence y 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 y And is selected identically or differently on each occurrence 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 y And is selected identically or differently on each occurrence 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 the inventionWherein R is x And R is y And is selected identically or differently on each occurrence 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, pyridinyl, trimethylsilyl, trimethylgermanium, and combinations thereof.
According to one embodiment of the invention, wherein at least one R y 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 one embodiment of the invention, wherein at least one R y 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 one embodiment of the invention, wherein at least one R y 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 groups.
According to one embodiment of the invention, wherein X 7 Selected from CR x The substituent R x Selected from fluorine.
According to one embodiment of the invention, wherein X 3 -X 8 At least two of them are selected from CR x One of said R x Selected from cyano or fluoro, the other of said R x Selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted silyl groups having 3 to 20 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein X 5 -X 8 At least two of them are selected from CR x One of said R x Selected from cyano or fluoro, the other of said R x 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 6-18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein X 7 And X 8 Selected from CR x One of said R x Selected from cyano or fluoro, another of said substituents R x Selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and combinations thereof.
According to one embodiment of the invention, ring A, ring B are selected identically or differently on each occurrence from carbocycles having 6 to 18 ring atoms, or heterocycles having 5 to 18 ring atoms.
According to one embodiment of the invention, ring A, ring B are selected identically or differently on each occurrence from aromatic rings having 6 to 18 ring atoms or heteroaromatic rings having 5 to 18 ring atoms.
According to one embodiment of the invention, ring A, ring B are selected identically or differently on each occurrence from aromatic rings having 6 to 12 ring atoms or heteroaromatic rings having 5 to 12 ring atoms.
According to one embodiment of the invention, ring a, ring B are selected identically or differently on each occurrence from aromatic or heteroaromatic rings having 6 ring atoms.
According to one embodiment of the present invention, wherein Ar has a structure represented by formula 4:
A 1 -A 4 is selected from CR, identically or differently at each occurrence A Or N;
B 1 -B 4 is selected from CR, identically or differently at each occurrence B Or N;
l is selected from the group consisting of: single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", ger" R ", BR", PR, P (O) R ", R" c=cr ", alkylene having 1 to 20 carbon atoms, heteroalkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms, heterocyclylene having 3 to 20 ring atoms, arylene having 6 to 30 carbon atoms, heteroarylene having 3 to 30 carbon atoms, and combinations thereof;
R A 、R B 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, 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, substitutedOr an unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group having from 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 ", R A ，R B Can optionally be linked to form a ring;
"onium" means the position of the linkage of formula 4.
According to one embodiment of the invention, wherein A 1 -A 4 Is selected from CR, identically or differently at each occurrence A 。
According to one embodiment of the invention, wherein A 1 -A 4 Is selected from CR, identically or differently at each occurrence A Or N, and A 1 -A 4 At least one of which is selected from N. For example A 1 -A 4 One or both of which are selected from N.
According to one embodiment of the invention, wherein B 1 -B 4 Is selected from CR, identically or differently at each occurrence B 。
According to one embodiment of the invention, wherein B 1 -B 4 Is selected from CR, identically or differently at each occurrence B Or N, and B 1 -B 4 At least one of which is selected from N. For example B 1 -B 4 One or both of which are selected from N.
According to one embodiment of the invention, wherein R A And R is B 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 alkyl having 3 to 20 ring carbon atomsSubstituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted 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.
According to one embodiment of the invention, wherein R A And R is B And is selected identically or differently on each occurrence 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 alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 6 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein R A And R is B And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, neopentyl, isopentyl, cyclopentyl, cyclohexyl, phenyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated neopentyl, deuterated isopentyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, and combinations thereof.
According to one embodiment of the invention, wherein L is selected from the group consisting of: a single bond, O, S, se, NR ", siR" R ", geR" R ", BR", PR ", P (O) R", a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted heterocyclylene group having 3 to 10 ring atoms, a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 10 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein L is selected from single bond, O, S, substituted or unsubstituted alkylene having 1-2 carbon atoms, phenylene.
According to one embodiment of the invention, wherein L is selected from single bonds.
According to one embodiment of the invention, wherein Ar is selected identically or differently for each occurrence from the group consisting of Ar 1 To Ar 102 A group consisting of Ar 1 To Ar 102 Is specified in claim 15.
According to one embodiment of the invention, wherein Ar 1 To Ar 57 And Ar is a group 61 To Ar 102 The hydrogen in (a) can be partially or completely replaced by deuterium.
According to one embodiment of the invention, wherein R 1 -R 7 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 3 And/or R 4 -R 7 The sum of the number of carbon atoms of (2) is at least 4.
According to one embodiment of the invention, wherein R 4 -R 7 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 4 -R 7 The sum of the number of carbon atoms of (2) is at least 4.
According to one embodiment of the invention, wherein R 2 ，R 5 ，R 6 At least one or at least two or all of which are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R 2 ，R 5 ，R 6 At least one or at least two or all of which are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstitutedCycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R 2 ，R 5 ，R 6 At least one or at least two or all of which are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, hydrogen in the above groups is partially or fully deuterated.
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 R' is selected, identically or differently, for each occurrence, from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring 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, and combinations thereof.
According to one embodiment of the invention, wherein L a Is selected identically or differently on each occurrence from the group consisting of L a1-1 -L a1-58 、L a2-1 -L a2-61 And L a3-1 -L a3-152 A group consisting of L a1-1 -L a1-58 、L a2-1 -L a2-61 And L a3-1 -L a3-152 The specific structure of which is shown in claim 20.
According to one embodiment of the invention, wherein L a1-1 -L a1-58 、L a2-1 -L a2-61 And L a3-1 -L a3-152 The hydrogen atoms of (a) can be partially or completely substituted 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 b595 A group consisting of L b1 To L b595 Is shown in the specific structure of (a)The method of claim 19.
According to one embodiment of the invention, wherein L b1 To L b595 The hydrogen atoms of (a) can be partially or completely substituted 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:
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According to one embodiment of the invention, wherein the metal complex has Ir (L a ) 2 L b Or IrL a (L b ) 2 Or Ir (L) a )(L b )(L c ) Wherein L is a Is selected identically or differently on each occurrence from the group consisting of L a1-1 -L a1-58 、L a2-1 -L a2-61 And L a3-1 -L a3-152 Group of L b Is selected identically or differently on each occurrence from the group consisting of L b1 To L b595 Group of L c Is selected identically or differently on each occurrence from the group consisting of L c1 To L c147 A group of; wherein L is a1-1 -L a1-58 、L a2-1 -L a2-61 And L a3-1 -L a3-152 The specific structure of (C) is shown in claim 20, L b1 To L b595 The specific structure of (a) is shown in claim 19, L c1 To L c147 The specific structure of (2) is shown above.
According to one embodiment of the invention, the metal complex has the group consisting of metal complex 1 to metal complex 1008, wherein the specific structure of metal complex 1 to metal complex 1008 is shown in claim 21.
According to one embodiment of the present invention, wherein the metal complex has hydrogen energy in metal complex 1 through metal complex 1008 partially or completely substituted with deuterium.
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, wherein at least one of the host compounds 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 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 amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, 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.
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 amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, 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 is selected from the group consisting of O, S, se, N, NR, the same or different at each occurrence 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 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 amine 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;
". 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 1
Step 1:
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to a dried 250mL round bottom flask was added in order intermediate 1 (12.2 g,53.3 mmol), carbazole (12.0 g,71.9 mmol), dimethyl sulfoxide 150mL and cesium carbonate (43.2 g,132.5 mmol), nitrogen was replaced three times and nitrogen protected, and the reaction was heated at 190℃for 12h. After the reaction was cooled, celite was filtered, washed with dichloromethane, the organic phase was collected, extracted with dichloromethane, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Purification by column chromatography eluting with Dichloromethane (DCM) afforded intermediate 2 (13.5 g,67.3% yield) as a solid.
Step 2:
to a dry 500mL round bottom flask was added in sequence intermediate 2 (7.0 g,18.6 mmol), iridium trichloride trihydrate (2.6 g,7.4 mmol), 150mL of 2-ethoxyethanol, 50mL of water, three nitrogen substitutions and nitrogen protection, and the reaction was heated with stirring at 130℃for 24h. After cooling, filtration, washing with methanol and n-hexane three times, respectively, and filtration under reduced pressure gave intermediate 3 as a yellow solid 6.5g (89.7% yield).
Step 3:
to a dry 500mL round bottom flask was added in sequence intermediate 3 (6.5 g,3.3 mmol), anhydrous dichloromethane 200mL, methanol 15mL, silver triflate (1.8 g,7.2 mmol), nitrogen sparged three times and nitrogen blanket, and stirred overnight at room temperature. The celite was filtered and dichloromethane washed 2 times and the lower organic phase was collected and concentrated under reduced pressure to afford intermediate 4,7.2g (94% yield).
Step 4:
to a dry 250mL round bottom flask was added in sequence intermediate 4 (2.5 g,2.2 mmol), intermediate 5 (1.1 g,4.3 mmol), 2-ethoxyethanol and N, N-dimethylformamide each 50mL, nitrogen replaced three times and nitrogen blanket, and the reaction was heated at 100deg.C for 96h. After the reaction cooled, the celite was filtered. Methanol, n-hexane were washed 2 times respectively, and the yellow solid above celite was dissolved with methylene chloride, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give the yellow solid product, metal complex 1 (0.2 g,7.6% yield). The product was identified as the target product and had a molecular weight of 1187.4.
Synthesis example 2: synthesis of Metal Complex 121
Step 1:
to a dry 250mL round bottom flask was added in sequence intermediate 4 (5.9 g,5.2 mmol), intermediate 6 (2.4 g,8.3 mmol), 2-ethoxyethanol and N, N-dimethylformamide each 50mL, nitrogen replaced three times and nitrogen blanket, and the reaction was heated at 100deg.C for 96h. After the reaction cooled, the celite was filtered. Methanol, n-hexane were washed 2 times respectively, and the yellow solid above celite was dissolved with methylene chloride, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give the metal complex 121 (0.4 g,6% yield) as a yellow solid product. The product was identified as the target product and had a molecular weight of 1213.4.
Synthesis example 3: synthesis of Metal Complex 157
Step 1:
to a dried 250mL round bottom flask was added in sequence intermediate 4 (3.1 g,2.7 mmol), intermediate 7 (1.8 g,5.4 mmol), 2-ethoxyethanol and N, N-dimethylformamide 30mL each, nitrogen replaced three times and nitrogen blanket, and the reaction was heated at 100deg.C for 96h. After the reaction cooled, the celite was filtered. Methanol, n-hexane were washed 2 times respectively, and the yellow solid above celite was dissolved with methylene chloride, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give the yellow solid product metal complex 157 (0.25 g,7.2% yield). The product was identified as the target product and had a molecular weight of 1283.5.
Those skilled in the art will recognize that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other compound structures of the present invention.
Device embodiment
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 complexes 1 are then used as dopants for the co-deposition with the compounds PH-23 and H-40 as generatorsOptical 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 was then transferred back to the glove box and packaged with a glass lid to complete the device.
Device comparative example 1
The embodiment of device comparative example 1 is the same as device example 1 except that the metal complex 1 of the present invention is replaced with the metal complex GD1 in the light-emitting layer (EML).
The detailed partial structure and thickness of the device layer are shown in table 1 below. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
Table 1 partial device structures of example 1 and comparative example 1
The material structure used in the device is as follows:
the IVL characteristics of the device were measured. At 1000 cd/m 2 The CIE data of the device, the maximum emission wavelength lambda, are measured max Full Width Half Maximum (FWHM), voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE); lifetime (LT 97) data was at 80 mA/cm 2 The test was performed at constant current. These data are recorded and shown in table 2.
Table 2 device data for device example 1 and comparative example 1
Discussion:
example 1 and comparative example 1 used the metal complex 1 of the present invention and the metal complex GD1 of the non-present invention, respectively, in an organic electroluminescent device. The metal complex 1 and GD1 have the same L of the structure of formula 1B of the present invention b Ligands differing only in L therein a Ligand-different, L in example 1 a The ligand is a ligand of the present invention having the structure of formula 1A, and L in comparative example 1 a The ligand is a phenylpyridine ligand not of the present invention. From the above device results, it can be seen that example 1 has a half-width narrower than comparative example 1 by 5nm, a drive voltage reduced by 0.12V, and CE, PE and EQE increased by 34.3%, 53.2% and 23.7%, respectively, and especially a device lifetime increased by a factor of 11.9. The above shows that L of the present invention comprising the structure of formula 1A a Ligand and L of structure 1B b Metal complexes of ligands, in contrast to having phenylpyridine ligands and L of the invention b The comparative metal complex of the ligand can obtain various performance improvements such as half-width, service life and efficiency (CE, PE and EQE) of the device, and the comprehensive performance of the device can be remarkably improved.
Device example 2
The embodiment of device example 2 is the same as device example 1 except that the inventive metal complex 121 is substituted for the inventive metal complex 1 in the light-emitting layer.
Device example 3
The embodiment of device example 3 is the same as device example 1 except that the inventive metal complex 157 is substituted for the inventive metal complex 1 in the light-emitting layer.
Device comparative example 2
The embodiment of device comparative example 2 is the same as device example 1 except that the metal complex 1 of the present invention is replaced with the metal complex GD2 in the light-emitting layer (EML).
The detailed partial structure and thickness of the device layer are shown in table 3 below. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
TABLE 3 partial device structures of examples 2-3 and comparative example 2
The structure of the materials newly used in the device is as follows:
the IVL characteristics of the device were measured. At 1000cd/m 2 The CIE data of the device, the maximum emission wavelength lambda, are measured max Full Width Half Maximum (FWHM), voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE); lifetime (LT 97) data was at 80mA/cm 2 The test was performed at constant current. These data are recorded and shown in table 4.
Table 4 device data for device examples 2 to 3 and comparative example 2
Discussion:
example 2 and comparative example 2 used the metal complex 121 of the present invention and the metal complex GD2 of the non-present invention, respectively, in an organic electroluminescent device. The metal complex 121 and GD2 have the same L having the structure of formula 1A of the present invention a Ligands differing only in L therein b The substitution positions of the substituents of formula 2 in the ligands are different. As can be seen from the data in table 4, completely unexpected results were obtained. Example 2 is comparable to comparative example 2 in drive voltage, 23.1nm narrower in half-width, and 43.4%, 45.1% and 50.7% increases in CE, PE and EQE, respectively, and an even more 80.9% increase in device lifetime. The above shows that L of the present invention comprising the structure of formula 1A a Ligand and L of formula 1B having substituent of formula 2 in specific position b Metal complexes of ligands, compared toL of substituents of formula 2 in different substitution positions b Ligands and L having the invention a The comparative metal complex of the ligand can obtain various performance improvements such as half-peak width, device service life, efficiency CE, PE and EQE) and the like, and can remarkably improve the comprehensive performance of the device.
Example 3 further on L based on example 2 a The ligand has alkyl substituent. On the basis of the great improvement in device performance of example 2 compared with comparative example 2, example 3 achieves performance equivalent to or better than that of example 2 in terms of device lifetime and efficiency. Indicating that the present invention comprises L having the structure of formula 1A a Ligand and L of structure 1B b The metal complexes of the ligand framework can all obtain excellent device performance.
Device comparative example 3
The embodiment of device comparative example 3 is the same as device example 1 except that the metal complex 1 of the present invention is replaced with a metal complex GD3 in the light-emitting layer (EML).
The detailed device layer partial structure and thickness are shown in table 5 below. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
TABLE 5 partial device structure of comparative example 3
The structure of the materials newly used in the device is as follows:
the IVL characteristics of the device were measured. At 1000cd/m 2 The CIE data of the device, the maximum emission wavelength lambda, are measured max Full Width Half Maximum (FWHM), voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE); these data are recorded and shown in table 6.
TABLE 6 device data for example 2 and comparative examples 2-3
Discussion:
comparative examples 2 and 3 use of non-inventive metal complexes GD2 and GD3, respectively, in an organic electroluminescent device, both of the metal complexes GD2 and GD3 comprising the same L having the structure of formula 1A of the present invention a Ligands differing only in L therein b Whether the ligand has a substituent of formula 2. As can be seen from the data in table 6, comparative example 2 has a comparable driving voltage to comparative example 3, but has a half-width of 8.4nm, and the CE, PE and EQE efficiencies are significantly reduced by 28.8%, 29.9% and 31.2%, respectively.
However, unlike example 2 and comparative example 3, the device performance was greatly improved. Example 2 and comparative example 3 respectively using the metal complex 121 of the present invention and the metal complex GD3 not of the present invention for use in an organic electroluminescent device, the metal complex 121 and GD3 comprise the same L having the structure of formula 1A of the present invention a Ligands differing only in L therein b Whether the ligand has a substituent of formula 2 at a specific position. As can be seen from the data in table 6, example 2 is comparable to or slightly improved in driving voltage, CE and PE compared to comparative example 3, but the half-width is 14.7nm narrower and the EQE is improved by 3.7%.
As can be seen from a comparison of the two sets of data of comparative example 2 and comparative example 3, L having the same structure of formula 1A a In the case of ligands, the different positions have substituted L of formula 2 b Ligand (comparative example 2 and example 2) versus L not containing substitution of formula 2 b The metal complex of (comparative example 3) achieved diametrically opposite device performance changes. L showing the structure of formula 1A of the present invention a Ligand and L of formula 1B having substituent of formula 2 in specific position b The metal complex of the ligand can obtain half-width, improve the performance of the device in multiple aspects such as CE, PE and EQE, and can obviously improve the deviceIs a combination of the properties of (a) and (b).
The results of the above examples 1-3 and comparative examples 1-3 are taken together to demonstrate that the L of the present invention comprising the structure of formula 1A a Ligand and L of formula 1B having substituent of formula 2 in specific position b The metal complex of the ligand can obtain the improvement of the service life, efficiency (CE, PE, EQE) and other properties of the device, and can obviously improve the comprehensive properties of the device. By using these metal complexes, more saturated green luminescence, higher device efficiency, narrower half-width, longer device lifetime, etc. of the device can be provided.
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 (26)
1. A metal complex having M (L a ) m (L b ) n (L c ) q Is represented by the general formula (I),
wherein,
L a 、L b and L c A first ligand, a second ligand and a third ligand which are coordinated with the metal M, respectively, and the third ligand L c Capable of binding to the first ligand L a Or a second ligand L b Selected from the same or different structures; wherein L is a 、L b And L c Can optionally be linked to form a multidentate ligand;
the metal M is selected from metals with relative atomic mass of more than 40;
m is selected from 1 or 2; n is selected from 1 or 2; q is selected from 0 or 1; when m=2, two L a The same or different; when n=2, two L b The same or different;
L a each occurrence of which is the same or different having the structure of formula 1A; l (L) b Each timeThe same or different at the occurrence of having the structure of formula 1B;
Wherein,
the ring Cy is, identically or differently, selected at each occurrence from an aromatic ring having 6-30 ring atoms, a heteroaromatic ring having 5-30 ring atoms, or a combination thereof;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
z is selected from the group consisting of O, S, se, CR 'R', siR 'R' and GeR 'R'; when two R's are present simultaneously, 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; and X is 1 -X 4 One of which is selected from C and is linked to a ring Cy;
X 1 ，X 2 ，X 3 or X 4 Coordination to the metal M via a metal-carbon bond or a metal-nitrogen bond;
a is selected from 0 or 1;
W 1 -W 3 is selected from CR, identically or differently at each occurrence w Or N;
U 1 -U 4 is selected from CR, identically or differently at each occurrence u 、NR u O, S or N, and U 1 -U 4 At most one of which is selected from N;
ar has a structure represented by formula 2:
in formula 2, "" represents the position of attachment of formula 2;
R A and R is B Each occurrence, identically or differently, represents mono-, poly-or unsubstituted;
ring a and ring B are identically or differently selected from carbocycles having 3 to 30 ring atoms, or heterocycles having 3 to 30 ring atoms;
l is selected from the group consisting of: single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", ger" R ", BR", PR ", P (O) R", R "c=cr", substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclylene having 3 to 20 ring atoms, substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, and combinations thereof;
R，R’，R”，R x ，R u ，R w ，R A And R is B 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;
L c The same or different at each occurrence is selected from monoanionic bidentate ligands;
adjacent to each otherSubstituents R', R x R can optionally be linked to form a ring;
adjacent substituents R ", R A ，R B Can optionally be linked to form a ring;
adjacent substituents R u Can optionally be linked to form a ring;
adjacent substituents R u And R is w Can optionally be linked to form a ring.
2. The metal complex of claim 1, wherein the ring Cy is, identically or differently, selected at 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;
Adjacent substituents R can optionally be joined to form a ring;
wherein, "#" indicates the position of connection with the metal M,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, M is selected, identically or differently, for each occurrence, from Pt or Ir.
4. The metal complex as defined in claim 1, U 1 -U 4 The same or different at each occurrence is selected from CR u The method comprises the steps of carrying out a first treatment on the surface of the And/or W 1 -W 3 The same or different at each occurrence is selected from CR w ；R u And R is w And is selected identically or differently on each occurrence 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, cyano groups, and combinations thereof;
preferably, R u And R is w And is selected identically or differently on each occurrence 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, cyano groups, and combinations thereof;
More preferably, R u And R is w Each time go outAnd wherein the times are 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, and combinations thereof.
5. The metal complex according to claim 1, wherein the metal complex has an Ir (L a ) m (L b ) 3-m And is represented by formula 3:
wherein,
m is selected from 1,2; when m=1, two L b The same or different; when m=2, two L a The same or different;
z is selected from the group consisting of O, S, se, 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 is selected from CR, identically or differently at each occurrence y Or N;
X 3 -X 8 is selected from CR, identically or differently at each occurrence x Or N;
ar has a structure represented by formula 2:
wherein, in the formula 2,
R A and R is B Each occurrence, identically or differently, represents mono-, poly-or unsubstituted;
ring a and ring B are identically or differently selected from carbocycles having 3 to 30 ring atoms, or heterocycles having 3 to 30 ring atoms;
L is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", ger" R ", BR", PR ", P (O) R", R "c=cr", 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 heterocyclylene group having 3 to 20 ring atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R’，R”，R x ，R y ，R 1 -R 7 ，R A and R is B 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;
"onium" represents the attachment position of formula 2;
adjacent substituents R', R x ，R y Can optionally be linked to form a ring;
adjacent substitutionRadicals R ", R A ，R B Can optionally be linked to form a ring;
adjacent substituents R 4 -R 7 Can optionally be linked to form a ring.
6. The metal complex as claimed in claim 1 or 5, Z is selected from O or S.
7. The metal complex as defined in claim 1 or 5, wherein X 3 -X 8 Is selected from CR, identically or differently at each occurrence x And/or Y 1 -Y 4 Is selected from CR, identically or differently at each occurrence y ；R x And R is y And is selected identically or differently on each occurrence 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 silyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkyl germanium groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof;
preferably, R x And R is y And is selected identically or differently on each occurrence 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 y And is selected identically or differently on each occurrence 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.
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 defined in claim 1,5 or 7, wherein X 3 -X 8 At least one of them is selected from CR x The substituent R x Selected from cyano or fluoro;
preferably X 5 -X 8 At least one of them is selected from CR x The substituent R x Selected from cyano or fluoro;
more preferably X 7 Or X 8 Selected from CR x The R is x Selected from cyano; or X 7 Selected from CR x The substituent R x Selected from fluorine.
10. The metal complex as defined in claim 1,5 or 7, wherein X 3 -X 8 At least two of them are selected from CR x One of said R x Selected from cyano or fluoro, the other of said R x Selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted silyl groups having 3 to 20 carbon atoms, and combinations thereof;
preferably X 5 -X 8 At least two of them are selected from CR x One of said R x Selected from cyano or fluoro, the other of said R x Selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substitutionOr unsubstituted heteroaryl groups having 3 to 18 carbon atoms, and combinations thereof;
more preferably X 7 And X 8 Selected from CR x One of said R x Selected from cyano or fluoro, another of said substituents R x Selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and combinations thereof.
11. The metal complex of claim 1 or 5, wherein ring a, ring B are, identically or differently, selected at each occurrence from a carbocycle having 6-18 ring atoms, or a heterocycle having 5-18 ring atoms;
Preferably, ring A, ring B are, identically or differently, selected for each occurrence from aromatic rings having 6 to 18 ring atoms, or heteroaromatic rings having 5 to 18 ring atoms.
12. The metal complex according to claim 1 or 5, wherein Ar has a structure represented by formula 4:
A 1 -A 4 is selected from CR, identically or differently at each occurrence A Or N;
B 1 -B 4 is selected from CR, identically or differently at each occurrence B Or N;
l is selected from the group consisting of: single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", ger" R ", BR", PR, P (O) R ", R" c=cr ", alkylene having 1 to 20 carbon atoms, heteroalkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms, heterocyclylene having 3 to 20 ring atoms, arylene having 6 to 30 carbon atoms, heteroarylene having 3 to 30 carbon atoms, and combinations thereof;
R A 、R B and R' is selected identically or differently on each occurrence from the group consisting ofThe group: 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;
Adjacent substituents R ", R A ，R B Can optionally be linked to form a ring;
"onium" means the position of the linkage of formula 4.
13. The metal complex of claim 12, wherein a 1 -A 4 Is selected from CR, identically or differently at each occurrence A And/or B 1 -B 4 Is selected from CR, identically or differently at each occurrence B ；R A And R is B And is selected identically or differently on each occurrence 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 silyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkyl germanium groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof;
preferably, R A And R is B And is selected identically or differently on each occurrence 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 6 carbon atoms, substituted or unsubstituted alkyl germanium groups having 3 to 6 carbon atoms, cyano groups, and combinations thereof;
More preferably, R A And R is B And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, neopentyl, isopentyl, cyclopentyl, cyclohexyl, phenyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated neopentyl, deuterated isopentyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, and combinations thereof.
14. The metal complex of claim 1, 5 or 12, wherein L is selected from the group consisting of: a single bond, O, S, se, NR, siR "R", ger "R", BR ", PR", P (O) R ", a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, a substituted or unsubstituted heterocyclylene group having 3 to 10 ring atoms, a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 10 carbon atoms, and combinations thereof;
preferably, L is selected from single bond, O, S, substituted or unsubstituted alkylene having 1-2 carbon atoms, phenylene;
More preferably, L is selected from single bonds.
15. The metal complex of claim 1, wherein Ar is selected identically or differently at each occurrence from the group consisting of:
optionally, the Ar 1 To Ar 57 And Ar is a group 61 To Ar 102 The hydrogen in (a) can be partially or completely replaced by deuterium.
16. The metal complex according to claim 5, wherein Y 1 -Y 4 Each occurrence is identical or different CR y Or N, and Y 1 -Y 4 At least one of them is selected from CR y And said R y 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 y 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.
17. The metal complex according to claim 5, wherein R 1 -R 7 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 a combination thereofCombining; and all of the R 1 -R 3 And/or R 4 -R 7 Is at least 4;
preferably, R 4 -R 7 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 4 -R 7 The sum of the number of carbon atoms of (2) is at least 4.
18. The metal complex according to claim 5, wherein R 2 ，R 5 ，R 6 At least one or at least two or all of which are selected from the group consisting of: deuterium, 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, R 2 ，R 5 ，R 6 At least one or at least two or all of which are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
More preferably, R 2 ，R 5 ，R 6 At least one or at least two or all of which are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, hydrogen in the above groups is partially or fully deuterated.
19. The metal complex as defined in claim 1 or 5, wherein L b Is selected identically or differently on each occurrence from the group consisting of L b1 To L b595 Group of L b1 To L b595 The specific structure of (2) is as follows:
the L is b1 To L b595 The structure is as follows:wherein R is 1 -R 7 Ar is selected from the atoms or groups in the following table:
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wherein t-Bu represents tert-butyl; neo-pent represents neopentyl; TMS represents trimethylsilyl.
20. The metal complex as claimed in claim 1,5 or 19, wherein L a And is selected identically or differently on each occurrence from the group consisting of:
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optionally, said L a1-1 -L a1-58 、L a2-1 -L a2-61 And L a3-1 -L a3-152 The hydrogen atoms of (a) can be partially or completely substituted by deuterium.
21. The metal complex of claim 1 or 20, wherein the metal complex has IrL a (L b ) 2 Two L' s b The same or different; l (L) a Selected from L a1-1 -L a1-58 、L a2-1 -L a2-61 And L a3-1 -L a3-152 Group of L b Is selected from L, identically or differently for each occurrence b1 -L b595 A group of;
preferably, the metal complex is selected from the group consisting of metal complex 1 to metal complex 1008, wherein metal complex 1 to metal complex 1008 have IrL a (L b ) 2 Two L' s b Identical, L a And L b Respectively corresponding to the structures indicated in the following table:
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optionally, hydrogen energy in the metal complexes 1 to 1008 is partially or fully substituted with deuterium.
22. 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 1-21.
23. The organic electroluminescent device of claim 22, wherein the organic layer comprising the metal complex is a light emitting layer.
24. The organic electroluminescent device of claim 23, 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.
25. The organic electroluminescent device of claim 24, 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.
26. A compound composition comprising the metal complex of any one of claims 1-21.
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