CN117177597A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
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- CN117177597A CN117177597A CN202311129860.0A CN202311129860A CN117177597A CN 117177597 A CN117177597 A CN 117177597A CN 202311129860 A CN202311129860 A CN 202311129860A CN 117177597 A CN117177597 A CN 117177597A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- 239000003446 ligand Substances 0.000 claims abstract description 64
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 26
- 239000012044 organic layer Substances 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 612
- -1 cyano, isocyano, hydroxy, mercapto, sulfonyl Chemical group 0.000 claims description 168
- 125000001424 substituent group Chemical group 0.000 claims description 161
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 239000010410 layer Substances 0.000 claims description 93
- 125000001072 heteroaryl group Chemical group 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 239000000463 material Substances 0.000 claims description 66
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 65
- 229910052799 carbon Inorganic materials 0.000 claims description 61
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 55
- 229910052805 deuterium Inorganic materials 0.000 claims description 55
- 238000006467 substitution reaction Methods 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 47
- 125000003342 alkenyl group Chemical group 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000004104 aryloxy group Chemical group 0.000 claims description 42
- 125000006413 ring segment Chemical group 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000002252 acyl group Chemical group 0.000 claims description 35
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 30
- 239000002184 metal Substances 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000005104 aryl silyl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 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
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 125000006267 biphenyl group Chemical group 0.000 claims description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 7
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 7
- 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 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
- 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 6
- 229960005544 indolocarbazole Drugs 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
- 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
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003636 chemical group 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
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 150000002739 metals Chemical group 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 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
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 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
- 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
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 10
- 229910052770 Uranium Inorganic materials 0.000 claims 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 230000006872 improvement Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 41
- 239000002019 doping agent Substances 0.000 description 27
- 150000001735 carboxylic acids Chemical class 0.000 description 19
- 230000003111 delayed effect Effects 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 150000003384 small molecules Chemical class 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 230000000670 limiting effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 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
- 229910052796 boron Chemical group 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
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 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
- 239000000126 substance Substances 0.000 description 3
- 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
- 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
- 125000004429 atom Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 238000012552 review Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000010703 silicon Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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Abstract
An organic electroluminescent device is disclosed. The organic electroluminescent device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a first metal complex having a ligand structure of formula 1 and a first host compound having a structure of formula 2. The organic electroluminescent device of the invention has obvious improvement on the device performance, such as the service life of the device. An electronic device comprising the organic electroluminescent device is also disclosed.
Description
Technical Field
The present invention relates to an organic electroluminescent device. And more particularly, to an organic electroluminescent device comprising a metal complex having a ligand of the structure of formula 1 and a first host compound having a structure of formula 2, and an electronic apparatus 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.
US20200127213A1 discloses an organic optoelectronic device, the light-emitting layer of which comprises a light-emitting layer consisting ofA first body represented by +.>A second body is shown. While this application exemplifies some phosphorescent dopants, it does not address the use of complex doping containing cyano-substituted fused ring type (hetero) aryl structure ligands in such host materials, nor does it disclose and teach that better performance can be obtained for devices having cyano-substituted fused ring type (hetero) aryl pyridine structures doped in such host materials.
WO2019017618A1 discloses an organic optoelectronic device whose light-emitting layer comprises a light-emitting layer consisting ofA first body represented by +.>A second body formed by bonding and a first body formed by bonding +.>The phosphorescent dopant is shown. However, this application does not address the use of complexes containing cyano-substituted fused ring (hetero) aryl structure ligands for doping such host materials, nor does it address the use of compounds having a dicarbazole backbone in devices, nor does it disclose or teach that better performance can be obtained by doping such host materials with complexes having cyano-substituted fused ring (hetero) aryl structure ligands.
US20170186965A1 discloses a device withStructuring ofA compound, and an electroluminescent device comprising said compound, the organic electroluminescent device further comprising a phosphorescent dopant, but the application only relates in embodiments to phenylpyridine-based Ir and Pt complexes as phosphorescent dopants. However, this application does not address the use of complex doping with cyano-substituted fused ring (hetero) aryl structural ligands in such host materials, nor does it disclose or teach that better performance can be obtained by doping a device with a cyano-substituted fused ring (hetero) aryl structural ligand in such host materials.
US20150340618A1 discloses a device withA compound of structure, and an electroluminescent device comprising said compound, the organic electroluminescent device further comprising a dopant, but the application only relates in embodiments to phenylpyridine-based Ir complexes as luminescent dopants. This application does not address the fact that better performance of the device can be obtained when complexes of ligands of condensed ring type (hetero) aryl structures bearing cyano groups are used in such host materials.
The present inventors have found through intensive studies that the combination properties of an organic electroluminescent device using a metal complex-based dopant material having a ligand of the structure of formula 1 and a first host compound having a specific structure can be significantly improved.
Disclosure of Invention
The present invention aims to solve at least some of the above problems by providing a series of organic electroluminescent devices comprising a metal complex-based dopant material having a ligand of the structure of formula 1 and a first host compound having a structure of formula 2.
According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes:
an anode is provided with a cathode,
a cathode electrode, which is arranged on the surface of the cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first metal complex and a first host compound;
Wherein, the firstA metal complex comprising a metal M and a ligand L coordinated to the metal M a Ligand L a Has a structure represented by formula 1:
wherein,
the metal M is selected from metals with relative atomic mass of more than 40;
cy is, identically or differently, selected for each occurrence from a substituted or unsubstituted aryl group having 5 to 24 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 24 ring atoms; the Cy is connected with the metal M through a metal-carbon bond or a metal-nitrogen bond;
z is selected identically or differently at each occurrence from the group consisting of O, S, se, NR 1 ，CR 1 R 1 And SiR 1 R 1 A group of; when two R's are simultaneously present 1 When two R 1 May be the same or different;
X 1 -X 8 is selected identically or differently on each occurrence from C, CR x Or N, and X 1 -X 4 At least one of which is C and is linked to said Cy;
X 1 、X 2 、X 3 or X 4 Is connected with the metal M through a metal-carbon bond or a metal-nitrogen bond;
R x and R is 1 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 aryl having 3 to 30 carbon atoms Substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
X 1 -X 8 at least one of them is CR x And said R is x Is cyano;
adjacent substituents R 1 ，R x Can optionally be linked to form a ring;
wherein the first host compound has a structure represented by formula 2:
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 connected with at least one of the formula A, the formula B, the formula C or the formula D;
wherein in formula A, formula B, formula C and formula D,
A 1 and A 2 The same or different at each occurrence is selected from the group consisting of O, S, se, NR n ，CR n R n And SiR n R n A group of; when two R's are simultaneously present n When two R n May be the same or different;
l 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;
W 1 And W is 8 Is selected from CR, identically or differently at each occurrence w1 Or N;
W 2 -W 7 is selected from CR, identically or differently at each occurrence w2 Or N;
Z 1 -Z 8 is selected identically or differently on each occurrence from C, CR z Or N, and Z 1 -Z 8 At least one of which is C and is connected with L;
Y 1 -Y 15 is selected identically or differently on each occurrence from C, CR y Or N; y in C 1 -Y 8 At least one of which is C and is connected with L; in the formula D, Y 1 -Y 7 At least one of them is C, Y 8 -Y 11 At least one of them is C, and all are connected with L;
R w1 and is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, substituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
R z And R is w2 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 unsubstitutedAralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R e ，R n 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 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;
* Represents the connection position of formula A, formula B, formula C or formula D with formula 2;
adjacent substituents R e ，R n ，R w2 ，R y ，R z Can optionally be linked into a ring.
According to another embodiment of the present invention, an electronic device is also disclosed, which includes the organic electroluminescent device described in the above embodiment.
The invention discloses an organic electroluminescent device comprising a metal complex dopant material having a ligand of formula 1 and a first host compound having a structure of formula 2. By selecting a specific combination of the host compound and the dopant compound, proper energy level matching of the luminescent layer material can be obtained, and the concentration of carriers in the luminescent layer can be effectively regulated and controlled to reach the desired balance.
Drawings
Fig. 1 is a schematic diagram of an organic electroluminescent device as disclosed herein.
Fig. 2 is a schematic view of another organic electroluminescent device disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically illustrates, without limitation, an organic light-emitting device 100. The drawings are not necessarily to scale, and some of the layer structures in the drawings may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the layers described. The nature and function of the layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F in a 50:1 molar ratio 4 m-MTDATA of TCNQ as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is at a 1:1 molar ratioBPhen doped with Li at the molar ratio as disclosed in U.S. patent application publication No. 2003/0230980, 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 (iric) rate is sufficiently fast 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. In addition, the alkyl group may be optionally substituted. 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 include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, t-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. 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. In addition, aryl groups may be optionally substituted. 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-tetrabiphenyl. In addition, aryl groups may be optionally substituted.
Heterocyclyl or heterocycle-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms including at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thietaneyl, azepanyl and tetrahydrosilol. In addition, the heterocyclic group may be optionally substituted.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furodipyridine, benzothiophene, thienodipyridine, benzoselenophene, selenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-boron, 1, 3-aza-boron, 1-aza-boron-4-aza, boron-doped compounds, and the like. In addition, heteroaryl groups may be optionally substituted.
Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.
Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenoxy. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl-substituted alkyl. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthyl-ethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthyl-ethyl, 2- β -naphthyl-ethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, cyano, o-cyanobenzyl, o-chlorobenzyl, 1-chlorophenyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. In addition, aralkyl groups may be optionally substituted.
Alkyl-as used herein, alkyl-substituted silicon groups are contemplated. The silyl group may be a silyl group having 3 to 20 carbon atoms, preferably a silyl group having 3 to 10 carbon atoms. Examples of the alkyl silicon group include trimethyl silicon group, triethyl silicon group, methyldiethyl silicon group, ethyldimethyl silicon group, tripropyl silicon group, tributyl silicon group, triisopropyl silicon group, methyldiisopropyl silicon group, dimethylisopropyl silicon group, tri-t-butyl silicon group, triisobutyl silicon group, dimethyl-t-butyl silicon group, and methyldi-t-butyl silicon group. In addition, the alkyl silicon group may be optionally substituted.
Arylsilane-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenyl silyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl, tri-tert-butylsilyl, dimethyl tert-butylsilyl, methyldi-tert-butylsilyl. In addition, arylsilane groups may be optionally substituted.
The term "aza" in azadibenzofurans, azadibenzothiophenes and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.
In the present disclosure, when any one of the terms from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphinyl, refers to alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphino groups, any one of which may be substituted with one or more groups selected from deuterium, halogen, unsubstituted alkyl having from 1 to 20 carbon atoms, unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having from 1 to 20 carbon atoms, unsubstituted heterocyclic group having from 3 to 20 carbon atoms, unsubstituted aryl having from 7 to 20 carbon atoms, unsubstituted alkoxy having from 7 to 30 carbon atoms, unsubstituted alkenyl having from 3 to 20 carbon atoms, unsubstituted alkoxy having from 3 to 30 carbon atoms, unsubstituted alkenyl having from 3 to 20 carbon atoms, unsubstituted alkenyl having from 3 to 30 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, 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 may be monocyclic or polycyclic, 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:
furthermore, the expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to carbon atoms directly bonded to each other 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 an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes:
an anode is provided with a cathode,
a cathode electrode, which is arranged on the surface of the cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first metal complex and a first host compound;
wherein the first metal complex comprises a metal M and a ligand L coordinated with the metal M a Ligand L a Has a structure represented by formula 1:
wherein,
the metal M is selected from metals with relative atomic mass of more than 40;
cy is, identically or differently, selected for each occurrence from a substituted or unsubstituted aryl group having 5 to 24 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 24 ring atoms; the Cy is connected with the metal M through a metal-carbon bond or a metal-nitrogen bond;
Z is selected identically or differently at each occurrence from the group consisting of O, S, se, NR 1 ，CR 1 R 1 And SiR 1 R 1 A group of; when two R's are simultaneously present 1 When two R 1 May be the same or different;
X 1 -X 8 is selected identically or differently on each occurrence from C, CR x Or N, and X 1 -X 4 At least one of which is C and is linked to said Cy;
X 1 、X 2 、X 3 or X 4 Is connected with the metal M through a metal-carbon bond or a metal-nitrogen bond;
R x and R is 1 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;
X 1 -X 8 At least one of them is CR x And said R is x Is cyano;
adjacent substituents R 1 ，R x Can optionally be linked to form a ring;
wherein the first host compound has a structure represented by formula 2:
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 connected with at least one of the formula A, the formula B, the formula C or the formula D;
wherein in formula A, formula B, formula C and formula D,
A 1 and A 2 The same or different at each occurrence is selected from the group consisting of O, S, se, NR n ，CR n R n And SiR n R n A group of; when two R's are simultaneously present n When two R n May be the same or different;
l 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;
W 1 and W is 8 Is selected from CR, identically or differently at each occurrence w1 Or N;
W 2 -W 7 is selected from CR, identically or differently at each occurrence w2 Or N;
Z 1 -Z 8 each timeAre identically or differently selected from C, CR z Or N, and Z 1 -Z 8 At least one of which is C and is connected with L;
Y 1 -Y 15 Is selected identically or differently on each occurrence from C, CR y Or N; y in C 1 -Y 8 At least one of which is C and is connected with L; in the formula D, Y 1 -Y 7 At least one of them is C, Y 8 -Y 11 At least one of them is C, and all are connected with L;
R w1 and is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, substituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
R z and R is w2 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 20 carbon atoms An atomic alkylsilyl group, a substituted or unsubstituted arylsilyl 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;
R e ，R n 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 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;
* Represents the connection position of formula A, formula B, formula C or formula D with formula 2;
adjacent substituents R e ，R n ，R w2 ，R y ，R z Can optionally be linked into a ring.
In this embodiment, "adjacent substituent R 1 ，R x Can optionally be linked to form a ring "comprising any one or more of the following: adjacent substituents R x Can be linked to form a ring; adjacent substituents R 1 May be joined to form a ring. In addition, adjacent substituents R 1 And R is x May be joined to form a ring. Another case is an adjacent substituent R 1 ，R x None of them are connected to form a ring.
In this embodiment, "adjacent substituent R e ，R n ，R w2 ，R y ，R z Can optionally be linked in a ring "comprising any one or more of the following: adjacent substituents R e Can be linked to form a ring; adjacent substituents R n Can be linked to form a ring; adjacent substituents R w2 Can be linked to form a ring; adjacent substituents R y Can be linked to form a ring; adjacent substituents R z May be joined to form a ring. In addition, adjacent substituents R n And R is y Can be connected to form a ring; adjacent substituents R e And R is y Can be connected to form a ring; adjacent substituents R e And R is w2 Can be connected to form a ring; adjacent substituents R e And R is z Can be connected to form a ring; adjacent substituents R n And R is z Can be connected to form a ring. Another case is an adjacent substituent R e ，R n ，R w2 ，R y ，R z None of them are connected to form a ring.
In this embodiment, "E 1 -E 6 At least one of which is C and which is attached to at least one of formula A, formula B, formula C or formula D "comprises one or more of the following: when E is 1 -E 6 When one of them is C, this one C may be linked to any one of the formulae A, B, C or D; when E is 1 -E 6 Where at least two of these are C, these two C's may be linked to any two of formulas A, B, C or D, respectively (including two structures of the same formula, e.g., linked to two B's, respectively), e.g., at least E 1 And E is 3 And C, and respectively connecting with the formula A and the formula B to obtain the structure shown as the formula 2C:for example E 1 And E is 3 In the case of C, are respectively connected with two formulas B, wherein A of one formula B 1 Selected from NR n The structure of formula 2b is obtained:
according to one embodiment of the invention, wherein E 1 -E 6 Is selected identically or differently on each occurrence from C, CR e Or N, and E 1 -E 6 Wherein three are N, E 1 -E 6 At least one is CR e And said R e And is selected identically or differently on each occurrence from the group consisting of: 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 a combination thereof.
According to one embodiment of the invention, wherein E 1 -E 6 Is selected identically or differently on each occurrence from C, CR e Or N, and E 1 -E 6 Wherein three are N, E 1 -E 6 At least one of C and CR e The method comprises the steps of carrying out a first treatment on the surface of the When E is 1 -E 6 Wherein at least one or two of them are C, each of them is independently linked to the above formula A, formula B, formula C or formula D; when E is 1 -E 6 At least one is CR e And said R e Each occurrence is identically or differently selected from a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, a substituted or substituted biphenyl group, or a combination thereof.
According to one embodiment of the invention, wherein E 1 -E 6 Is selected identically or differently on each occurrence from C, CR e Or N, and E 1 -E 6 Wherein three are N, E 1 -E 6 At least two of which are C and are each independently linked to formula A, formula B, formula C or formula D.
Herein, "E 1 -E 6 At least two of which are C and are each independently of the other connected to formula A, formula B, formula C or formula D "are intended to mean that when E 1 -E 6 Where at least two of these are selected from C, these two C's may be linked to any two of formula A, formula B, formula C or formula D respectively (including two structures of the same formula, e.g., linked to two B's respectively). For example E 1 And E is 3 And C, and respectively connecting with the formula A and the formula B to obtain the structure shown as the formula 2C: For example E 1 And E is 3 In the case of C, are respectively connected with two formulas B, wherein A of one formula B 1 Selected from NR n The structure of formula 2b is obtained:
According to one embodiment of the invention, wherein W 1 And W is 8 Is selected from CR, identically or differently at each occurrence w1 ；W 2 -W 7 Is selected from CR, identically or differently at each occurrence w2 ；Z 1 -Z 8 Is selected identically or differently on each occurrence from C or CR z ；Y 1 -Y 15 Is selected identically or differently on each occurrence from C or CR y ；
Adjacent substituents R w2 ，R z ，R y Can optionally be linked into a ring.
In this embodiment, "adjacent substituent R w2 ，R z ，R y Can optionally be linked in a ring "comprising any one or more of the following: adjacent substituents R y Can be linked to form a ring; adjacent substituents R w2 Can be linked to form a ring; adjacent substituents R z May be joined to form a ring. Another case is an adjacent substituent R w2 ，R z ，R y None of them are connected to form a ring.
According to one embodiment of the invention, wherein said R w1 ，R w2 ，R y At least one member selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted silyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, hydroxyl groups, and combinations thereof.
According to one embodiment of the invention, whereinThe R is w1 ，R w2 ，R y At least two of which are selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted silyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, hydroxyl groups, and combinations thereof.
According to one embodiment of the invention, wherein said R w1 ，R w2 ，R y At least one selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein said R w1 ，R w2 ，R y Selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein said R z At least one of which is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
According to one embodiment of the present invention, wherein the first host compound has a structure represented by one of formulas 2a to 2 f:
Wherein, in the formulas 2a to 2f,
A 1 、A 2 the same or different at each occurrence is selected from the group consisting of O, S, se, NR n ，CR n R n And SiR n R n A group of; when two R's are simultaneously present n When two R n May be the same or different;
l 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;
ar is selected, identically or differently, for each occurrence, from 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, or a combination thereof;
W 1 and W is 8 Is selected from CR, identically or differently at each occurrence w1 Or N;
W 2 -W 7 is selected from CR, identically or differently at each occurrence w2 Or N;
Z 1 -Z 8 is selected identically or differently on each occurrence from C, CR z Or N, and Z 1 -Z 8 At least one of which is C and is connected with L;
Y 1 -Y 15 is selected identically or differently on each occurrence from C, CR y Or N; y in C 1 -Y 8 At least one of which is C and is connected with L; in the formula D, Y 1 -Y 7 At least one of them is C, Y 8 -Y 11 At least one of them is C, and all are connected with L;
R w1 And is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, substituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof;
R z and R is w2 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;
R n 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 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;
adjacent substituents R n ，R y Can optionally be linked into a ring.
According to one embodiment of the present invention, wherein L is selected, identically or differently, for each occurrence from the group consisting of a single bond, a substituted or unsubstituted alkylene group having from 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkylene group having from 3 to 6 carbon atoms, a substituted or unsubstituted arylene group having from 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having from 3 to 12 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein L is selected, identically or differently, for each occurrence, from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group.
According to one embodiment of the invention, wherein L is selected, identically or differently, for each occurrence, from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group.
According to one embodiment of the invention, wherein Ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 18 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein Ar is identically or differently selected from a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein Ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, a substituted or substituted biphenyl group, or a combination thereof.
According to one embodiment of the present invention, wherein the first host compound has a structure represented by formula 2 a.
According to an embodiment of the invention, wherein the first host compound is selected from the group consisting of compounds 2a-1 to 2a-45, wherein the specific structure of compounds 2a-1 to 2a-45 is shown in claim 8.
According to one embodiment of the invention, wherein the first host compound has a structure represented by formula 2 b.
According to an embodiment of the invention, wherein the first host compound is selected from the group consisting of compounds 2b-1 to 2b-63, wherein the specific structure of compounds 2b-1 to 2b-63 is shown in claim 8.
According to one embodiment of the invention, wherein the first host compound has a structure represented by formula 2 c.
According to an embodiment of the invention, wherein the first host compound is selected from the group consisting of compounds 2c-1 to 2c-90, wherein the specific structure of compounds 2c-1 to 2c-80 is shown in claim 8.
According to one embodiment of the invention, wherein the first host compound has a structure represented by formula 2 d.
According to an embodiment of the invention, wherein the first host compound is selected from the group consisting of compounds 2d-1 to 2d-27, wherein the specific structure of compounds 2d-1 to 2d-27 is shown in claim 8.
According to one embodiment of the present invention, wherein the first host compound has a structure represented by formula 2 e.
According to an embodiment of the invention, wherein the first host compound is selected from the group consisting of compounds 2e-1 to 2e-27, wherein the specific structure of compounds 2e-1 to 2e-27 is shown in claim 8.
According to one embodiment of the invention, wherein the first host compound has a structure represented by formula 2 f.
According to an embodiment of the invention, wherein the first host compound is selected from the group consisting of compounds 2f-1 to 2f-21, wherein the specific structure of compounds 2f-1 to 2f-21 is shown in claim 8.
According to one embodiment of the invention, wherein the first host compoundThe product has a structure represented by formula 2c, Z 5 -Z 8 At least one of them is CR z And said R z Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
According to one embodiment of the present invention, wherein the first host compound has a structure represented by formula 2c, W 1 And W is 8 Is selected from CR, identically or differently at each occurrence w1 ，W 2 -W 7 Is selected from CR, identically or differently at each occurrence w2 ，Z 1 -Z 8 Is selected identically or differently on each occurrence from C or CR z And Z is 1 -Z 4 At least one of which is C and is connected with L;
Z 1 -Z 8 at least one of them is CR z And at least one R z Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
According to one embodiment of the present invention, wherein the first host compound has a structure represented by formula 2c, wherein the substituent R w1 And R is w2 At least one or two of which is optionally substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted silyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilane having 6 to 20 carbon atoms, and combinations thereof.
According to one embodiment of the present invention, wherein in formula 1, cy is any one structure selected from the group consisting of:
wherein,
r represents identically or differently for each occurrence a single substitution, multiple substitution or no substitution;
r is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, phosphino, sulfinyl, sulfonyl, and combinations thereof;
Adjacent substituents R can optionally be joined to form a ring;
wherein, '#' indicates the position of connection with the metal M;
' represents X in formula 1 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 when a plurality of substituents R are present, any adjacent substituents R can be linked to form a ring. To be used forFor example, when two adjacent substituents R are present, i.e. +.>Multiple substituents R in the formula can then be linked to form a ring +.>Obviously, when multiple substituents are presentR is not necessarily a ring, and any adjacent substituents R may not be bonded.
According to one embodiment of the invention, wherein Cy is selected from
Wherein,
r represents identically or differently for each occurrence a single substitution, multiple substitution or no substitution;
r is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, phosphino, sulfinyl, sulfonyl, and combinations thereof;
Adjacent substituents R can optionally be joined to form a ring;
wherein, '#' indicates the position of connection with the metal M;
' represents X in formula 1 1 ，X 2 ，X 3 Or X 4 The location of the connection.
According to one embodiment of the present invention, wherein in formula 1, X 1 -X 8 At least one of which is selected from N.
According to one embodiment of the present invention, wherein in formula 1, X 1 -X 8 Is selected identically or differently on each occurrence from C or CR x 。
According to one embodiment of the invention, ligand L a Has a structure represented by formula 1 a:
wherein,
z is selected identically or differently at each occurrence from the group consisting of O, S, se, NR 1 ，CR 1 R 1 And SiR 1 R 1 A group of; when two R's are simultaneously present 1 When two R 1 May be the same or different;
X 3 -X 8 each occurrence is identically or differently selected from CR x Or N;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R x r and R 1 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;
X 3 -X 8 At least one of them is CR x And said R x Is cyano;
adjacent substitutionRadical R x ，R 1 R can optionally be linked to form a ring.
Herein, "adjacent substituent R x ，R 1 R can optionally be linked to form a ring "including any one or more of the following: adjacent substituents R can be connected to form a ring; adjacent substituents R 1 Can be connected to form a ring; adjacent substituents R x Can be connected to form a ring. In addition, adjacent substituents R 1 And R is x Can be connected to form a ring, and adjacent substituent groups R and R 1 Can be connected to form a ring, and adjacent substituent groups R and R x Can be connected to form a ring. Another case is the adjacent substituents R, R 1 ，R x None of them are connected to form a ring.
According to one embodiment of the invention, wherein the ligand L a And is selected, identically or differently, on each occurrence, from any one of the group consisting of:
wherein,
z is selected identically or differently at each occurrence from the group consisting of O, S, se, NR 1 ，CR 1 R 1 And SiR 1 R 1 A group of; when two R's are simultaneously present 1 When two R 1 May be the same or different;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R x each occurrence, identically or differently, represents mono-or poly-substitution;
R，R x And R is 1 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;
at least one R x Is cyano;
adjacent substituents R, R x And R is 1 Can optionally be linked to form a ring;
preferably, at least one R is also present in the above structure x And 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, cyano groups, and combinations thereof.
According to one embodiment of the inventionEmbodiments, wherein in formula 1, X 1 -X 8 At least two of them are selected from CR x And one of R x Is cyano, another 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, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein the ligand L a Each occurrence is identically or differently selected from any one of the following structures:
wherein,
z is selected identically or differently for each occurrence from O, S, se;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R x Each occurrence, identically or differently, represents mono-or poly-substitution;
R，R x and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl 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;
At least one R x Is cyano;
adjacent substituents R, R x Can optionally be linked to form a ring;
preferably, at least one R is also present in the above structure x And 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, cyano groups, and combinations thereof.
In this embodiment, "adjacent substituents R, R x Can optionally be linked to form a ring "comprising any one or more of the following: adjacent substituents R can be connected to form a ring; adjacent substituents R x Can be connected to form a ring. In addition, adjacent substituents R and R x May be joined to form a ring. Another case is the adjacent substituents R, R x None of them are connected to form a ring.
According to one embodiment of the invention, ligand L a At least two R's are present x And one of R x Is cyano, another R x Selected 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.
According to one embodiment of the invention, wherein L a At least two R's are present x And wherein at least one R x Is cyano, another R x Selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to one embodiment of the invention, ligand L a Selected from the following structures:
wherein,
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R 3 -R 8 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, 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, sulfinyl, phosphinyl, and combinations thereof;
R 3 -R 8 At least one of which is cyano; adjacent substituents can optionally be linked to form a ring;
preferably, R 5 -R 8 At least one of which is cyano;
more preferably, R 7 Or R is 8 Is cyano.
According to one embodiment of the invention, ligand L a Is selected identically or differently on each occurrence from the group consisting of L a1 -L a83 A group consisting of L a1 -L a83 The specific structure of which is shown in claim 19.
According to one embodiment of the invention, wherein the first metal complex has M (L a ) m (L b ) n (L c ) q Is of the general formula (I);
wherein,
the metal M is selected from metals with relative atomic mass of more than 40;
the ligand L a ，L b And L c Can optionally be linked to form a multidentate ligand;
m=1, 2 or 3, n=0, 1 or 2, q=0, 1 or 2, m+n+q being equal to the oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L a May be the same or different; when n is equal to 2, two L b May be the same or different; when q is equal to 2, two L c May be the same or different.
In this embodiment, "the ligand L a ，L b And L c The "capable of being optionally linked to form a multidentate ligand" includes any one or more of the following: l (L) a ，L b And L c Any two of which may be linked to form a tetradentate ligand; l (L) a ，L b And L c Can be linked to each other to form a hexadentate ligand. Another case is ligand L a ，L b And L c None are linked so that a multidentate ligand is not formed.
According to one embodiment of the invention, wherein the metal M is selected identically or differently on each occurrence from the group consisting of Cu, ag, au, ru, rh, pd, os, ir and Pt;
according to one embodiment of the invention, wherein the metal M is chosen identically or differently for each occurrence from Pt or Ir.
According to one embodiment of the invention, ligand L b And L c A structure shown at each occurrence as being the same or different selected from any one of the group consisting of:
wherein,
R a ，R b and R is c 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 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;
Ligand L b And L c Adjacent substituents can optionally be linked to form a ring.
In this example, "ligand L b And L c In which adjacent substituents can optionally be linked to form a ring "comprise any one or more of the following: adjacent substituents R a Can be connected to form a ring; adjacent substituents R b Can be connected to form a ring; adjacent substituents R c Can be connected to form a ring; adjacent substituents R a And R is b Can be connected to form a ring; adjacent substituents R a And R is c Can be connected to form a ring; adjacent substituents R b And R is c Can be connected to form a ring; adjacent substituents R C1 And R is C2 Can be connected to form a ring; adjacent substituents R b And R is C1 Can be connected to form a ring; adjacent substituents R a And R is C1 Can be connected to form a ring; adjacent substituents R c And R is C1 Can be connected to form a ring; adjacent substituents R b And R is C2 Can be connected to form a ring; adjacent substituents R a And R is C2 Can be connected to form a ring; adjacent substituents R c And R is C2 Can be connected to form a ring; adjacent substituents R b And R is N1 Can be connected to form a ring; adjacent substituents R a And R is N1 Can be connected to form a ring; adjacent substituents R c And R is N1 Can be connected to form a ring; . Alternatively, none of the adjacent substitutions are joined to form a ring.
According to one embodiment of the invention, ligand L b And L c Is selected identically or differently on each occurrence from the group consisting of L b1 -L b195 A group consisting of L b1 -L b195 The specific structure of which is shown in claim 21.
According to one embodiment of the present invention, wherein the first metal complex has a structure represented by formula 1 b:
wherein,
m is 1,2 or 3;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R 3 -R 16 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 atomsA group, a substituted or 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 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;
R 3 -R 8 At least one of which is cyano;
preferably, R 7 Or R is 8 Is cyano;
adjacent substituents can optionally be joined to form a ring.
In this embodiment, "adjacent substituents can optionally be linked to form a ring" includes one or more of the following: adjacent substituents R may be linked to form a ring, adjacent substituents R 3 And R is 4 Can be connected to form a ring, and adjacent substituent groups R 5 And R is 4 Can be connected to form a ring, and adjacent substituent groups R 5 And R is 6 Can be connected to form a ring, and adjacent substituent groups R 6 And R is 7 Can be connected to form a ring, and adjacent substituent groups R 7 And R is 8 Can be connected to form a ring, and adjacent substituent groups R 9 And R is 10 Can be connected to form a ring, and adjacent substituent groups R 10 And R is 11 Can be connected to form a ring, and adjacent substituent groups R 11 And R is 12 Can be connected to form a ring, and adjacent substituent groups R 12 And R is 13 Can be connected to form a ring, and adjacent substituent groups R 13 And R is 14 Can be connected to form a ring, and adjacent substituent groups R 14 And R is 15 Can be connected to form a ring, and adjacent substituent groups R 15 And R is 16 Can be connected to form a ring. In addition, adjacent substituents R and R 3 -R 16 Can be connected to form a ring. Another case is adjacentNone of the substituents are linked to form a ring.
According to one embodiment of the invention, wherein the substituents R 3 -R 8 At least one of which is cyano and the substituents R 3 -R 8 At least one of the remainder selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted 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, sulfinyl, phosphino, and combinations thereof.
According to one embodiment of the invention, wherein the substituents R 3 -R 8 At least one of which is cyano and the substituents R 3 -R 8 At least one of the remainder 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, cyano groups, and combinations thereof.
Herein, "substituent R 3 -R 8 At least one of which is cyano and the substituents R 3 -R 8 The remainder "in (2) means: for example when the substituents R 3 In the case of cyano, then the substituent R 3 -R 8 The remainder of (B) refers to the substituent R 4 -R 8 The method comprises the steps of carrying out a first treatment on the surface of the When the substituent R 7 In the case of cyano, and takeSubstituent R 3 -R 8 The remainder of (B) refers to the substituent R 3 -R 6 And R is 8 The method comprises the steps of carrying out a first treatment on the surface of the When the substituent R 8 In the case of cyano, and substituents R 3 -R 8 The remainder of (A) being substituents R 3 -R 7 The method comprises the steps of carrying out a first treatment on the surface of the Similarly, other situations may be similarly considered.
According to one embodiment of the invention, wherein the substituents R 9 -R 16 At least one selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted 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, sulfinyl, phosphino, and combinations thereof.
According to one embodiment of the invention, wherein the substituents R 9 -R 16 At least one 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, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein the substituents R 10 ，R 11 ，R 15 At least one selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atomsCycloalkyl groups of ring carbon atoms, substituted or unsubstituted aryl groups of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein the substituents R 10 ，R 11 ，R 15 At least one selected from the group consisting of: substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein the substituents R 10 ，R 11 ，R 15 At least two of which are selected from the group consisting of: deuterium, fluorine, 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 the substituents R 10 ，R 11 ，R 15 At least two of which are selected from the group consisting of: substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, and combinations thereof.
According to an embodiment of the invention, wherein the first metal complex is selected from the group consisting of compounds GD1 to GD82, the specific structure of compounds GD1 to GD82 is shown in claim 25.
According to one embodiment of the invention, wherein the organic layer further comprises a second host compound comprising 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 an embodiment of the invention, wherein the organic layer further comprises at least one second host compound, the second host material comprises at least one chemical group selected from the group consisting of: benzene, carbazole, indolocarbazole, fluorene, silafluorene, and combinations thereof.
According to one embodiment of the invention, wherein the second host compound has a structure represented by formula X:
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;
v is selected, identically or differently, for each occurrence, from C, CR v Or N, and at least one of V is C, and is with L x Connecting;
u is selected, identically or differently, from C, CR for each occurrence u Or N, and at least one of U is C and is with L x Connecting;
R v and R is u 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 silyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 3 to 20 carbon atoms Arylsilane groups of 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
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 v And R is u Can optionally be linked to form a ring.
Herein, "adjacent substituent R v And R is u Can optionally be linked to form a ring "comprising any one or more of the following: adjacent substituents R v Optionally linked to form a ring; adjacent substituents R u Optionally linked to form a ring. In addition, adjacent substituents R v And R is u Optionally linked to form a ring. Another case is an adjacent substituent R v And R is u None of them are connected to form a ring.
According to one embodiment of the invention, wherein the second host compound has a structure represented by one of formulas X-a to X-j:
v is selected, identically or differently, for each occurrence, from C, CR v Or N, and at least one of V is C, and is with L x Connecting;
U is selected, identically or differently, from C, CR for each occurrence u Or N, and at least one of U is C and is with L x Connecting;
R v and R is u And is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstitutedSubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 ring atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, phosphonyl, 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 v And R is u Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein said V is selected identically or differently on each occurrence from C or CR v U is selected identically or differently from C or CR for each occurrence u Wherein R is u And R is v And are selected identically or differently on each occurrence from 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 arylsilyl groups having 6 to 20 carbon atoms.
According to one embodiment of the invention, wherein said V is selected identically or differently on each occurrence from C or CR v U is selected identically or differently from C or CR for each occurrence u Wherein R is u And R is v And is selected identically or differently on each occurrence from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms.
According to one embodiment of the invention, wherein said V is selected identically or differently on each occurrence from C or CR v U is selected identically or differently from C or CR for each occurrence u Wherein R is u And R is v And is selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof, identically or differently for each occurrence.
According to one embodiment of the invention, wherein Ar is 1 The same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 24 carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein Ar is 1 And is selected identically or differently on each occurrence from the group consisting of: phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
According to one embodiment of the invention, wherein said L x The groups are selected, identically or differently, on each occurrence from single bonds, substituted or unsubstituted arylene groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein said L x And is selected, identically or differently, for each occurrence from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group.
According to one embodiment of the invention, wherein said L x Is a single bond, phenyl or biphenyl.
According to one embodiment of the invention, wherein the second host compound has a structure represented by formula X-h.
According to an embodiment of the invention, wherein the second host compound is selected from the group consisting of compounds X-1 to X-126, wherein the specific structure of compounds X-1 to X-126 is shown in claim 32.
According to one embodiment of the present invention, the organic layer is a light emitting layer, and the organic layer light emitting layer includes a first metal complex, a first host compound and a second host compound, wherein the total weight of the first metal complex is 1% to 30% of the weight of the light emitting layer.
According to one embodiment of the present invention, the organic layer is a light emitting layer, and the organic layer light emitting layer includes a first metal complex, a first host compound and a second host compound, wherein the total weight of the first metal complex is 3% -13% of the weight of the light emitting layer.
According to an embodiment of the present invention, an electronic device is also disclosed, which includes the organic electroluminescent device according to any of the foregoing 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.
Device embodiment
The method of manufacturing the organic electroluminescent device is not limited, and the method of manufacturing the following examples is only one example and should not be construed as limiting. Those skilled in the art will be able to make reasonable modifications to the preparation methods of the following examples in light of the prior art. The proportions of the various materials in the light-emitting layer are not particularly limited, and those skilled in the art can reasonably select a certain range according to the prior art, for example, 10% -90% of the first host compound, 10% -90% of the second host compound, and 1% -60% of the dopant compound, based on the total weight of the materials in the light-emitting layer; or preferably, the dopant compound comprises 3% -30%. More preferably, the first host compound comprises 20% to 65%, the second host compound comprises 20% to 65%, and the dopant compound comprises 3% to 30%. The characteristics of the light emitting device prepared in the examples were tested using equipment conventional in the art, 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. The first metal complex, the first host compound, the second host compound, and the like used in the present invention are all easily available to those skilled in the art, and may be obtained, for example, commercially, by referring to a preparation method in the prior art, or may be obtained by referring to a preparation method in chinese application CN2019100770790 or US20200127213A1, and will not be described herein.
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 The deposition was performed sequentially on the ITO anode by thermal vacuum deposition at a rate of 0.2 to 2 a/s in the case of a tray. The compound HI is used as a Hole Injection Layer (HIL). The compound HT serves as a Hole Transport Layer (HTL). Compound X-4 was used as an Electron Blocking Layer (EBL). Then, the compound GD59 was doped in the first and second hosts 2c-31 and X-4, and co-evaporation was used as an emission layer (EML), with a ratio of the first and second hosts 2c-31 and X-4 of 1:1. Compound H1 was used as a Hole Blocking Layer (HBL). On the hole blocking layer, the compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated 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 encapsulated with a glass cover and a moisture absorbent to complete the device.
Example 2
The preparation of example 2 was the same as in example 1, except that compound 2c-3 was used in place of compound 2c-31 in the light-emitting layer (EML).
Comparative example 1
Comparative example 1 was prepared as in example 1, except that compound H1 was used in place of compound 2c-31 in the light-emitting layer (EML).
The detailed device portion layering and thicknesses are shown in the following table. Wherein more than one of the materials used is obtained by doping different compounds in the weight ratio described.
Table 1 partial device structures of example 1, example 2 and comparative example 1
The material structure used in the device is as follows:
table 2 shows the results at 15mA/cm 2 CIE data and current efficiency measured under constant current; at 80mA/cm 2 Device lifetime measured at constant current (LT 95).
Table 2 device data for example 1, example 2 and comparative example 1
Discussion:
in examples 1 to 2 and comparative example 1, the current efficiency of the device was comparable to or improved as compared with the case of using H1 as the first host, but the device lifetime was improved by about 78.2% and 33.0%, respectively, when the first host compounds 2c-31, 2c-3 of the present invention were doped with the Ir complex-based phosphorescent dopant GD59 containing the cyano-substituted dibenzofuranylpyridine ligand of the present invention.
Example 3
The preparation of example 3 was the same as example 1, except that compound GD2 was used in place of compound GD59 in the light-emitting layer (EML).
Comparative example 2
Comparative example 2 was prepared as in example 3, except that compound H1 was used in place of compound 2c-31 in the light-emitting layer (EML).
The detailed device portion layering and thicknesses are shown in the following table. Wherein more than one of the materials used is obtained by doping different compounds in the weight ratio described.
TABLE 3 partial device structures of example 3 and comparative example 2
The structure of the materials newly used in the device is as follows:
table 4 shows the results at 15mA/cm 2 CIE data and current efficiency measured under constant current; at 80mA/cm 2 Device lifetime measured at constant current (LT 95).
Table 4 device data for example 3 and comparative example 2
Discussion:
in example 3 and comparative example 2, the current efficiency of the device was the same as that of comparative example when the first host compound 2c-31 of the present invention was doped with the Ir complex-based phosphorescent dopant GD2 containing the cyano-substituted dibenzofuranylpyridine ligand of the present invention, but the device lifetime was improved by about 40.4% as compared with the case when H1 was used as the first host.
Example 4
Example 4 was prepared the same as example 1 except that compound 2d-1 was used in place of compound 2c-31 in the light emitting layer (EML).
Example 5
The preparation of example 5 was the same as in example 1, except that compound GD60 was used instead of compound GD59 and compound 2d-1 was used instead of compound 2c-31 in the light-emitting layer (EML).
Comparative example 3
Comparative example 3 was prepared as in example 5, except that compound H1 was used in place of compound 2d-1 in the light emitting layer (EML).
The detailed device portion layering and thicknesses are shown in the following table. Wherein more than one of the materials used is obtained by doping different compounds in the weight ratio described.
Table 5 partial device structures of example 4, example 5 and comparative example 3
The structure of the materials newly used in the device is as follows:
table 6 shows the results at 15mA/cm 2 CIE data and current efficiency measured under constant current; at 80mA/cm 2 Device lifetime measured at constant current (LT 95).
Table 6 device data for example 4, example 5 and comparative examples 1, 3
Discussion:
the first host compound H1 is a currently commercially available host material, and in example 4 and comparative example 1, when the first host material 2d-1 of the present invention is doped with the Ir complex-based phosphorescent dopant GD59 containing the cyano-substituted dibenzofuranylpyridine ligand of the present invention, the current efficiency of the device is comparable to that in the case of using the commercially available material H1 as the first host, and the lifetime of the device is improved.
In example 5 and comparative example 3, the current efficiency and lifetime of the device were improved when the first host material 2d-1 of the present invention was doped with the Ir complex-based phosphorescent dopant GD60 containing the cyano-substituted dibenzofuranylpyridine ligand of the present invention, as compared with the case of using the commercial material H1 as the first host.
The above results indicate that the first host compound 2d-1 can achieve device performance comparable to that of commercial host material H1, even with a slight improvement.
Example 6
The preparation of example 6 was the same as in example 1, except that compound GD12 was used in place of compound GD59 in the light-emitting layer (EML).
Comparative example 4
Comparative example 4 was prepared as in example 6, except that compound H1 was used in place of compound 2c-31 in the light-emitting layer (EML).
Example 7
The preparation of example 7 was the same as in example 1, except that compound GD18 was used in place of compound GD59 in the light-emitting layer (EML).
Example 8
Example 8 was prepared the same as example 7 except that compound 2c-3 was used in place of compound 2c-31 in the light emitting layer (EML).
Comparative example 5
Comparative example 5 was prepared the same as example 7 except that compound H1 was used in place of compound 2c-31 in the light emitting layer (EML).
The detailed device portion layering and thicknesses are shown in the following table. Wherein more than one of the materials used is obtained by doping different compounds in the weight ratio described.
Table 7 partial device structures of examples 6 to 8 and comparative examples 4 to 5
The structure of the materials newly used in the device is as follows:
table 8 shows the results at 15mA/cm 2 CIE data and current efficiency measured under constant current; at 80mA/cm 2 Device lifetime measured at constant current (LT 95).
Table 8 device data for examples 6 to 8 and comparative examples 4 to 5
Discussion:
in example 6 and comparative example 4, when the first host compound 2c-31 of the present invention was doped with the Ir complex phosphorescent dopant GD12 containing the cyano-substituted dibenzofuranylpyridine ligand of the present invention, the current efficiency of the device was slightly lower than that of the comparative example, but the device lifetime was improved by about 41.6% as compared with the case of using H1 as the first host.
In examples 7 to 8 and comparative example 5, for the Ir complex-based phosphorescent dopant GD18 containing the cyano-substituted dibenzofuranylpyridine ligand of the present invention, the current efficiency of the device was slightly improved as compared with the comparative example when the first host compounds 2c-31, 2c-3 of the present invention were doped, but the device lifetime was improved by about 35% and 22%, respectively, as compared with the case when H1 was used as the first host.
Example 9
The preparation of example 9 was the same as in example 1, except that compound GD43 was used in place of compound GD59 in the light-emitting layer (EML).
Comparative example 6
Comparative example 6 was prepared the same as example 9 except that compound H1 was used in place of compound 2c-31 in the light emitting layer (EML).
Comparative example 7
Comparative example 7 was prepared as in example 9, except that compound a was used in place of compound GD43 in the light-emitting layer (EML).
Comparative example 8
Comparative example 8 was prepared the same as comparative example 7 except that compound H1 was used in place of compound 2c-31 in the light emitting layer (EML).
The detailed device portion layering and thicknesses are shown in the following table. Wherein more than one of the materials used is obtained by doping different compounds in the weight ratio described.
Table 9 partial device structures of example 9 and comparative examples 6 to 8
The structure of the materials newly used in the device is as follows:
table 10 shows the results at 15mA/cm 2 CIE data and current efficiency measured under constant current; at 80mA/cm 2 Device lifetime measured at constant current (LT 95).
Table 10 device data for example 9 and comparative examples 6 to 8
Discussion:
as can be seen from example 9 and comparative example 6, the doping of the first host compound 2c-31 according to the present invention with the Ir complex-based phosphorescent dopant GD43 containing the cyano-substituted dibenzofuranylpyridine ligand according to the present invention improves the current efficiency and lifetime of the device compared to the case of using H1 as the first host, and particularly, the device lifetime is improved by 54.3% when using the first host compound 2c-31.
As can be seen from example 9 and comparative example 7, when the Ir complex-based phosphorescent dopant GD43 containing the cyano-substituted dibenzofuranyl pyridine ligand of the present invention was used, the current efficiency and lifetime were both improved, particularly, the lifetime was improved by about 64.8%, as compared to the Ir complex-based phosphorescent dopant compound a not containing the cyano-substituted dibenzofuranyl pyridine ligand.
Comparative example 7 has a lifetime enhancement of only 25.8% when the first host material 2c-31 of the present invention is doped using the phosphorescent dopant compound a having no cyano substituent as compared with comparative example 8, compared with the case of using H1 as the first host, compared with the lifetime enhancement (54.3%) of the Ir complex phosphorescent dopant GD43 having a cyano-substituted dibenzofuranylpyridine ligand of the present invention, and the lifetime enhancement is reduced by 110%. Therefore, the Ir complex phosphorescent dopant containing cyano-substituted dibenzofuran pyridine ligand and the first main compound have particularly excellent effect on prolonging the service life of the device, and the device can achieve very high service life.
In summary, when the metal complex-based dopant having the cyano-substituted ligand structure of formula 1 and the first host compound having a specific structure of the present invention are used in an organic layer, the device performance is improved compared to other devices, wherein the current efficiency of the device is comparable to or improved over that of the comparative example, the lifetime of the device is improved, and a portion of the lifetime of the device is significantly improved. This provides the industry with a combination of excellent luminescent layer materials.
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 (34)
1. 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, the organic layer comprising at least a first metal complex and a first host compound;
wherein the first metal complex comprises a metal M and a ligand L coordinated with the metal M a Ligand L a Has a structure represented by formula 1:
wherein,
the metal M is selected from metals with relative atomic mass of more than 40;
cy is, identically or differently, selected for each occurrence from a substituted or unsubstituted aryl group having 5 to 24 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 24 ring atoms; the Cy is connected with the metal M through a metal-carbon bond or a metal-nitrogen bond;
Z is selected identically or differently at each occurrence from the group consisting of O, S, se, NR 1 ，CR 1 R 1 And SiR 1 R 1 A group of; when two R's are simultaneously present 1 When two R 1 May be the same or different;
X 1 -X 8 is selected identically or differently on each occurrence from C, CR x Or N, and X 1 -X 4 At least one of which is C and is linked to said Cy;
X 1 、X 2 、X 3 or X 4 Is connected with the metal M through a metal-carbon bond or a metal-nitrogen bond;
R x and R is 1 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;
X 1 -X 8 At least one of them is CR x And said R is x Is cyano;
adjacent substituents R 1 ，R x Can optionally be linked to form a ring;
wherein the first host compound has a structure represented by formula 2:
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 connected with at least one of the formula A, the formula B, the formula C or the formula D;
wherein in formula A, formula B, formula C and formula D,
A 1 and A 2 The same or different at each occurrence is selected from the group consisting of O, S, se, NR n ，CR n R n And SiR n R n A group of; when two R's are simultaneously present n When two R n May be the same or different;
l 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;
W 1 and W is 8 Is selected from CR, identically or differently at each occurrence w1 Or N;
W 2 -W 7 is selected from CR, identically or differently at each occurrence w2 Or N;
Z 1 -Z 8 is selected identically or differently on each occurrence from C, CR z Or N, and Z 1 -Z 8 At least one of which is C and is connected with L;
Y 1 -Y 15 Is selected identically or differently on each occurrence from C, CR y Or N; y in C 1 -Y 8 At least one of which is C and is connected with L; in the formula D, Y 1 -Y 7 At least one of them is C, Y 8 -Y 11 At least one of them is C, and all are connected with L;
R w1 and is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, substituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 20 carbon atomsSubstituted or unsubstituted aryloxy groups having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, and combinations thereof;
R z and R is w2 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;
R e ，R n 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 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 atomsAryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
* Represents the connection position of formula A, formula B, formula C or formula D with formula 2;
Adjacent substituents R e ，R n ，R w2 ，R y ，R z Can optionally be linked into a ring.
2. The organic electroluminescent device of claim 1, wherein E 1 -E 6 Is selected identically or differently on each occurrence from C, CR e Or N, and E 1 -E 6 Wherein three are N, E 1 -E 6 At least one is CR e And said R e And is selected identically or differently on each occurrence from the group consisting of: 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, or a combination thereof;
preferably, said R e Each occurrence is identically or differently selected from a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenyl group, a substituted or substituted biphenyl group, or a combination thereof.
3. The organic electroluminescent device as claimed in claim 1 or 2, wherein E 1 -E 6 Is selected identically or differently on each occurrence from C, CR e Or N, and E 1 -E 6 Wherein three are N, E 1 -E 6 At least two are selected from C and are each independently linked to formula A, formula B, formula C or formula D.
4. An organic electroluminescent device as claimed in any one of claims 1 to 3Wherein W is 1 And W is 8 Is selected from CR, identically or differently at each occurrence w1 ；W 2 -W 7 Is selected from CR, identically or differently at each occurrence w2 ；Z 1 -Z 8 Is selected identically or differently on each occurrence from C or CR z ；Y 1 -Y 15 Is selected identically or differently on each occurrence from C or CR y ；
Adjacent substituents R z ，R w2 ，R y Can optionally be linked into a ring.
5. The organic electroluminescent device according to claim 1, wherein the first host compound has a structure represented by one of formulae 2a to 2 f:
wherein, in the formulas 2a to 2f,
A 1 、A 2 、L、Z 1 -Z 8 、W 1 -W 8 y is as follows 1 -Y 15 Having the same definition as claim 1;
ar is selected, identically or differently, for each occurrence, from 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, or a combination thereof.
6. The organic electroluminescent device as claimed in any one of claims 1 to 5, wherein the R w1 ，R w2 ，R y At least one or two selected from the group consisting of 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, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atomsA substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a hydroxyl group, and combinations thereof;
preferably, said R w1 ，R w2 ，R y At least one or two selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, and combinations thereof.
7. The organic electroluminescent device of any of claims 1-6, wherein L is selected, identically or differently, at each occurrence from a single bond, a substituted or unsubstituted alkylene group having 1-6 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-6 carbon atoms, a substituted or unsubstituted arylene group having 6-12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-12 carbon atoms, or a combination thereof;
preferably, L is selected, identically or differently, for each occurrence, from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group;
more preferably, L is selected, identically or differently, for each occurrence, from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group.
8. The organic electroluminescent device of claim 1, wherein the first host compound is selected from the group consisting of:
9. As claimed inThe organic electroluminescent device according to claim 6, wherein the first host compound has a structure represented by formula 2c, Z 5 -Z 8 At least one of them is CR z And said R is z Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
10. The organic electroluminescent device according to claim 6, wherein the first host compound has a structure represented by formula 2c, W 1 And W is 8 Is selected from CR, identically or differently at each occurrence w1 ，W 2 -W 7 Is selected from CR, identically or differently at each occurrence w2 ，Z 1 -Z 8 Is selected identically or differently on each occurrence from C or CR z And Z is 1 -Z 4 At least one of which is C and is connected with L;
Z 1 -Z 8 at least one of them is CR z And at least one R z Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
11. The organic electroluminescent device according to any one of claims 1 to 10, wherein in formula 1, cy is any one structure selected from the group consisting of:
wherein,
r represents identically or differently for each occurrence a single substitution, multiple substitution or no substitution;
r is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, phosphino, sulfinyl, sulfonyl, and combinations thereof;
Adjacent substituents R can optionally be joined to form a ring;
preferably, cy is
Wherein, '#' indicates the position of connection with the metal M;
' represents X in formula 1 1 ，X 2 ，X 3 Or X 4 The location of the connection.
12. The organic electroluminescent device as claimed in any one of claims 1 to 11, wherein in formula 1, X 1 -X 8 At least one of which is selected from N.
13. The organic electroluminescent device as claimed in any one of claims 1 to 11, wherein in formula 1, X 1 -X 8 Is selected identically or differently on each occurrence from C or CR x 。
14. The organic electroluminescent device as claimed in any one of claims 1 to 11, wherein the ligand L a Has a structure represented by formula 1 a:
wherein,
z is selected identically or differently at each occurrence from the group consisting of O, S, se, NR 1 ，CR 1 R 1 And SiR 1 R 1 A group of; when two R's are simultaneously present 1 When two R 1 May be the same or different;
X 3 -X 8 each occurrence is identically or differently selected from CR x Or N;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R x r and R 1 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;
X 3 -X 8 At least one of them is CR x And said R x Is cyano;
adjacent substituents R x ，R 1 R can optionally be linked to form a ring.
15. The organic electroluminescent device as claimed in any one of claims 1 to 11, wherein the ligand L a And is selected, identically or differently, on each occurrence, from any one of the group consisting of:
wherein,
z is selected identically or differently at each occurrence from the group consisting of O, S, se, NR 1 ，CR 1 R 1 And SiR 1 R 1 A group of; when two R's are simultaneously present 1 When two R 1 May be the same or different;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R x each occurrence, identically or differently, represents mono-or poly-substitution;
R，R x and R is 1 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 Substituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkyl silicon groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl silicon groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
at least one R x Is cyano;
adjacent substituents R, R x And R is 1 Can optionally be linked to form a ring;
preferably, at least one R is also present in the above structure x And 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, cyano groups, and combinations thereof.
16. The organic electroluminescent device as claimed in any one of claims 1 to 11, 14 and 15, wherein the ligand L a Each occurrence is identically or differently selected from any one of the following structures:
wherein,
z is selected identically or differently for each occurrence from O, S, se;
R represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R x each occurrence, identically or differently, represents mono-or poly-substitution;
R，R x and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstitutedSubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
At least one R x Is cyano;
adjacent substituents R, R x Can optionally be linked to form a ring;
preferably, at least one R is also present in the above structure x And 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, cyano groups, and combinations thereof.
17. The organic electroluminescent device as claimed in any one of claims 1 to 16, wherein the ligand L a At least two R's are present x And one of R x Is cyano, another R x Selected 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, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
18. The organic electroluminescent device as claimed in any one of claims 1 to 11, 14 and 15, wherein the ligand L a Selected from the following structures:
wherein,
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R 3 -R 8 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, 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, sulfinyl, phosphinyl, and combinations thereof;
R 3 -R 8 at least one of which is cyano; adjacent substituents can optionally be linked to form a ring;
Preferably, R 5 -R 8 At least one of which is cyano;
more preferably, R 7 Or R is 8 Is cyano.
19. The organic electroluminescent device as claimed in any one of claims 1 to 11, wherein the ligand L a And is selected, identically or differently, on each occurrence, from any one of the group consisting of:
20. the organic electroluminescent device as claimed in any one of claims 1 to 19, wherein the first metal complex has M (L a ) m (L b ) n (L c ) q Is of the general formula (I);
wherein,
the metal M is selected, identically or differently, for 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;
the ligand L a ，L b And L c Can optionally be linked to form a multidentate ligand;
m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L a May be the same or different; when n is equal to 2, two L b May be the same or different; when q is equal to 2, two L c May be the same or different;
preferably, wherein ligand L b And L c A structure shown at each occurrence as being the same or different selected from any one of the group consisting of:
wherein,
R a ，R b and R is c 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 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;
Ligand L b And L c Adjacent substituents can optionally be linked to form a ring.
21. The organic electroluminescent device as claimed in claim 20, wherein the ligand L b And L c And is selected identically or differently on each occurrence from the group consisting of:
22. the organic electroluminescent device as claimed in any one of claims 1 to 21, wherein the first metal complex has a structure represented by formula 1 b:
wherein,
m is 1,2 or 3;
r represents identically or differently for each occurrence a single substitution, multiple substitution, or no substitution;
R 3 -R 16 and R is identical or different at each occurrenceSelected 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;
R 3 -R 8 At least one of which is cyano;
adjacent substituents can optionally be linked to form a ring;
preferably, R 7 Or R is 8 Is cyano.
23. The organic electroluminescent device as claimed in claim 22, wherein the substituent R 3 -R 8 At least one of which is cyano and the substituents R 3 -R 8 At least one of the remainder of (B) and a substituent R 9 -R 16 At least one selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstitutedAryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Preferably, the substituent R 3 -R 8 At least one of which is cyano and the substituents R 3 -R 8 At least one of the remainder of (B) and a substituent R 9 -R 16 At least one 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, cyano groups, and combinations thereof.
24. The organic electroluminescent device as claimed in claim 22 or 23, wherein the substituent R 10 ，R 11 ，R 15 At least one or both of which is selected from the group consisting of: deuterium, fluorine, 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, the substituent R 10 ，R 11 ，R 15 At least one or both of which is selected from the group consisting of: substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, and combinations thereof.
25. The organic electroluminescent device of claim 1 or 20, wherein the first metal complex is selected from the group consisting of:
26. The organic electroluminescent device of any one of claims 1-25, wherein the organic layer further comprises a second host compound comprising 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;
preferably, the second host material comprises at least one chemical group selected from the group consisting of: benzene, carbazole, indolocarbazole, fluorene, silafluorene, and combinations thereof.
27. The organic electroluminescent device of claim 26, wherein the second host compound has a structure represented by formula X:
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;
V is selected, identically or differently, for each occurrence, from C, CR v Or N, and at least one of V is C, and is with L x Connecting;
u is selected, identically or differently, from C, CR for each occurrence u Or N, and at least one of U is C and is with L x Connecting;
R v and R is u 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 unsubstitutedSubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
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 v And R is u Can optionally be linked to form a ring.
28. The organic electroluminescent device of claim 27, wherein the second host compound has a structure represented by one of formulae X-a to X-j:
wherein, in the formulas X-a to X-j,
therein, V, L x U and Ar 1 Having the same definition as claim 27.
29. The organic electroluminescent device of claim 27 or 28, wherein V is selected identically or differently at each occurrence from C or CR v U is selected identically or differently from C or CR for each occurrence u Wherein R is u And R is v And is selected identically or differently on each occurrence from 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 cycloalkyl having 6-An aryl group of 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms;
Preferably, wherein R u And R is v Each occurrence is identically or differently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms;
more preferably, wherein R u And R is v And is selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof, identically or differently for each occurrence.
30. The organic electroluminescent device of any one of claims 27-29, wherein the Ar 1 The same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 24 carbon atoms, or combinations thereof;
preferably, wherein said Ar 1 And is selected identically or differently on each occurrence from the group consisting of: phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
31. The organic electroluminescent device of any one of claims 27-30, wherein the L x Each occurrence is identically or differently selected from a single bond, 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;
preferably, wherein said L x Each occurrence of which is identically or differently selected from a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted diphenyl groupAnd thienyl;
more preferably, wherein said L x Is a single bond, phenyl or biphenyl.
32. The organic electroluminescent device of any one of claims 26-28, wherein the second host compound is selected from the group consisting of:
33. the organic electroluminescent device of claim 1, wherein the organic layer is a light-emitting layer comprising a first metal complex, the first host compound and a second host compound, the total weight of the first metal complex being 1% to 30% by weight of the light-emitting layer;
preferably, the total weight of the first metal complex accounts for 3% -13% of the total weight of the light-emitting layer.
34. An electronic device comprising the organic electroluminescent device of claims 1-33.
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