CN114524850A - Organic electroluminescent material and device thereof - Google Patents
Organic electroluminescent material and device thereof Download PDFInfo
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- CN114524850A CN114524850A CN202111036660.1A CN202111036660A CN114524850A CN 114524850 A CN114524850 A CN 114524850A CN 202111036660 A CN202111036660 A CN 202111036660A CN 114524850 A CN114524850 A CN 114524850A
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- 239000000463 material Substances 0.000 title abstract description 42
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 229910052751 metal Inorganic materials 0.000 claims abstract description 34
- 239000002184 metal Substances 0.000 claims abstract description 34
- 239000003446 ligand Substances 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 287
- -1 phosphino groups Chemical group 0.000 claims description 134
- 239000010410 layer Substances 0.000 claims description 80
- 125000001424 substituent group Chemical group 0.000 claims description 76
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 229910052805 deuterium Inorganic materials 0.000 claims description 38
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 23
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000005104 aryl silyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000006413 ring segment Chemical group 0.000 claims description 17
- 238000006467 substitution reaction Methods 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 13
- 125000004185 ester group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 229910052741 iridium Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002739 metals 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 4
- 229960005544 indolocarbazole Drugs 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 150000002148 esters Chemical class 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
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003636 chemical group Chemical group 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 abstract description 6
- 230000006872 improvement Effects 0.000 abstract description 5
- 238000004020 luminiscence type Methods 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 3
- 230000009467 reduction Effects 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000003111 delayed effect Effects 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 238000005538 encapsulation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 229940093475 2-ethoxyethanol Drugs 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 125000000477 aza group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-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
- 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
- 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
- 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 group 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 group 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
- 239000004305 biphenyl Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group 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
- 239000010703 silicon Chemical group 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- HWIATMHDQVGMFQ-UHFFFAOYSA-N 1,3-azaborinine Chemical compound B1=CC=CN=C1 HWIATMHDQVGMFQ-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
- OBUDOIAYABJUHQ-UHFFFAOYSA-N 1,4-azaborinine Chemical compound B1=CC=NC=C1 OBUDOIAYABJUHQ-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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Abstract
Disclosed are an organic electroluminescent material and a device thereof. The organic electroluminescent material comprises L with a structure of formula 1aMetal complexes of ligands by reaction at LaFluorine substituents are introduced into specific positions of the ligands, and the novel compounds can provide more saturated luminescence and better device performance when being applied to electroluminescent devices, such as improvement of device efficiency and reduction of device voltage. Also disclosed are an electroluminescent device comprising the metal complex and a compound composition comprising the metal complex.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a composition comprising L having the structure of formula 1aMetal complexes of ligands, and organic electroluminescent devices and compound combinations comprising the metal complexes.
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (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 plasma light emitting devices.
In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer 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). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise 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. Since OLEDs are a self-emissive solid state device, it offers 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 the fabrication of flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through 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 are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.
Various OLED manufacturing methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing and nozzle printing. Small molecule OLEDs can also be made by solution processes if the material can be dissolved or dispersed in a solvent.
The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have the problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full-color OLED displays typically employ a hybrid strategy, using either blue fluorescence and phosphorescent yellow, or red and green. At present, the rapid decrease in efficiency of phosphorescent OLEDs at high luminance is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
Cyano substitution is not often introduced into phosphorescent metal complexes, such as iridium complexes. The application US20200251666a1, which was filed earlier by the applicant of the present application, discloses metal complexes with cyano-substituted ligands, which can be applied to organic electroluminescent devices to improve device performance and color saturation, although reaching the higher level in the industry, there is still room for improvement.
Disclosure of Invention
The present invention aims to provide a series of L containing structures having formula 1aMetal complexes of ligands to solve at least part of the above problems. The metal complexes can be used as light-emitting materials in electroluminescent devices. The novel compounds can be applied to electroluminescent devices to provide more saturated luminescence and better device performance, such as improvement of device efficiency and reduction of device voltage.
According to one embodiment of the present invention, a metal complex comprising a metal M, and a ligand L coordinated to the metal M is disclosedaWherein L isaHas a structure represented by formula 1:
in the formula 1, the first and second groups,
the metal M is selected from metals having a relative atomic mass greater than 40;
z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;
X1-X8selected from C, CR, identically or differently at each occurrencexOr N;
Y1-Y4selected from CR, identically or differently at each occurrenceyOr N;
R，Rx，Ryeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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;
X1-X8at least one of which is CRxAnd said R isxIs cyano;
Y2and Y3At least one of which is CRyAnd said R isyIs F;
adjacent substituents R, RxAnd RyCan optionally be linked to form a ring.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device, including:
an anode, a cathode, an anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the metal complex of the previous embodiments.
According to another embodiment of the present invention, a combination of compounds is also disclosed, comprising the metal complex of the preceding embodiments.
The invention discloses a series of L containing structures with formula 1aMetal complexation of ligandsThrough the reaction of LaFluorine substituents are introduced into specific positions of the ligands, and the novel compounds can provide more saturated luminescence and better device performance when being applied to electroluminescent devices, such as improvement of device efficiency and reduction of device voltage.
Drawings
FIG. 1 is a schematic representation of an organic light emitting device that can contain the metal complexes and compound combinations disclosed herein.
FIG. 2 is a schematic representation of another organic light emitting device that may contain combinations of the metal complexes and compounds disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures 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, an emissive 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 described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. 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 at a molar ratio of 50:14TCNQ m-MTDATA 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. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. patent No. incorporated by reference in its entiretyExamples of cathodes are disclosed in U.S. Pat. Nos. 5,703,436 and 5,707,745, which include composite cathodes having a thin layer of a metal, such as Mg: Ag, with an overlying layer of transparent, conductive, sputter-deposited ITO. 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 injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may 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 via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some 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 sub-layers. 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, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against 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 a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, which is incorporated herein by reference in its entirety.
Devices manufactured according to embodiments of the present invention may be incorporated into various 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, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "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 "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but that the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate the 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 retardation component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ ES-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).
Definitions for substituent terms
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-as used herein, includes both 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, comprises a cyclic alkyl group. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl are preferable. In addition, the cycloalkyl group may be optionally substituted.
Heteroalkyl-as used herein, heteroalkyl comprises a alkyl chain wherein one or more carbons are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxyethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. In addition, heteroalkyl groups may be optionally substituted.
Alkenyl-as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 3-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group, a 3-phenyl-1-butenyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cycloheptenyl group, a cycloheptatrienyl group, a cyclooctenyl group, a cyclooctatetraenyl group and a norbornenyl group. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight chain alkynyl groups are 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 include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Of the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 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 aryl groups 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, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-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-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 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-quaterphenyl. In addition, the aryl group may be optionally substituted.
Heterocyclyl or heterocyclic-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 a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuryl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. 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 a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom. 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, oxatriazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzoselenophenepyridyl, selenophene bipyridine, selenobenzodipyridine, selenium benzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group 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 those 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 the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy groups may be optionally substituted.
Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of the aryl and heteroaryl groups are the same as those 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 the aryloxy group include a phenoxy group and a biphenyloxy group. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl-substituted alkyl groups. 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 the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 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-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable. In addition, the aralkyl group may be optionally substituted.
Alkylsilyl-as used herein, alkyl substituted silyl is contemplated. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethylisopropylsilyl group, tri-tert-butylsilyl group, triisobutylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. Additionally, the alkylsilyl group may be optionally substituted.
Arylsilyl-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 the arylsilyl group include triphenylsilyl group, phenylbiphenylsilyl group, diphenylbiphenylsilyl group, phenyldiethylsilyl group, diphenylethylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, phenyldiisopropylsilyl group, diphenylisopropylsilyl group, diphenylbutylsilyl group, diphenylisobutylsilyl group, diphenyltert-butylsilyl group, tri-tert-butylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. In addition, the arylsilyl group may be optionally substituted.
The term "aza" in azabenzofuran, azabenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic moiety 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 may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in 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 phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which may be substituted with one or more substituents selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on 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 to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom 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 it enhances the efficiency and stability of the device.
In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. 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 carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as 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 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:
further, 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 two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at a position to which a hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
according to one embodiment of the present invention, a metal complex is disclosed comprising a metal M, and a ligand L coordinated to the metal MaWherein L isaHas a structure represented by formula 1:
in the formula 1, the first and second groups,
the metal M is selected from metals having a relative atomic mass greater than 40;
z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;
X1-X8selected from C, CR, identically or differently at each occurrencexOr N;
Y1-Y4selected from CR, identically or differently at each occurrenceyOr N;
R，Rx，Ryeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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;
X1-X8at least one of which is CRxAnd said R isxIs cyano;
Y2and Y3At least one of which is CRyAnd said R isyIs F;
adjacent substituents R, RxAnd RyCan optionally be linked to form a ring.
As used herein, the "adjacent substituents R, Rx，RyCan optionally be linked to form a ring ", is intended to denote a group in which adjacent substituents are present, for example, between two substituents R, two substituents RxIn between, two substituents RyIn between, two substituents RyAnd RxIn between, two substituents R and RxAnd any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to an embodiment of the invention, wherein LaHas a structure represented by one of formulas 1a-1 e:
z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;
in the formulae 1a and 1c, X3-X8Selected from CR, identically or differently at each occurrencexOr N;
in formula 1b, X1And X4-X8Selected from CR, identically or differently at each occurrencexOr N;
in formula 1d and formula 1e, X1-X2And X5-X8Selected from CR, identically or differently at each occurrencexOr N;
Y1-Y4selected from CR, identically or differently at each occurrenceyOr N;
R，Rx，Ryeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilane 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;
in formula 1a, X3-X8At least one of which isCRxAnd said R isxIs cyano;
in formula 1b, X1And X4-X8At least one of which is CRxAnd said R isxIs cyano;
in the formulae 1c and 1d, X1-X2And X5-X8At least one of which is CRxAnd said R isxIs cyano;
Y2and Y3At least one of which is CRyAnd said R isyIs F;
adjacent substituents R, Rx，RyCan optionally be linked to form a ring.
According to one embodiment of the invention, wherein the metal complex has M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein,
the metal M is selected from metals having a relative atomic mass greater than 40; preferably, M is selected, identically or differently on each occurrence, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; more preferably, M is selected, identically or differently on each occurrence, from Pt or Ir;
La、Lband LcAre respectively a first, a second and a third ligand coordinated to the metal M, and LcAnd said LaOr LbAre the same or different; wherein L isa、LbAnd LcOptionally linked to form a multidentate ligand; for example, La、LbAnd LcAny two of which can be linked to form a tetradentate ligand; also for example, La、LbAnd LcCan be connected with each other to form a hexadentate ligand; or also for example La、Lb、LcAre not linked so as not to form a multidentate ligand;
m1, 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 2 or more, a plurality of LaThe same or different; when n is equal to 2, two LbThe same or different; when q is equal to 2, two LcThe same or different;
Lband LcA structure, which is the same or different at each occurrence, selected from any one of the group consisting of:
wherein,
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1，CRC1RC2；
Ra，Rb，Rc，RN1，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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;
adjacent substituents Ra，Rb，Rc，RN1，RC1And RC2Can optionally be linked to form a ring.
As used herein, the "adjacent substituent Ra，Rb，Rc，RN1，RC1And RC2Can optionally be linked to form a ring ", is intended to denote a group of adjacent substituents therein, e.g. two substituents RaIn between, two substituents RbIn between, two substituents RcOf a substituent RaAnd RbOf a substituent RaAnd RcOf a substituent RbAnd RcOf a substituent RaAnd RN1Of a substituent RbAnd RN1Of a substituent RaAnd RC1Of R is a substituentaAnd RC2Of a substituent RbAnd RC1Of a substituent RbAnd RC2And R isC1And RC2And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the present invention, wherein the metal complex has a structure represented by formula 2:
wherein,
m is selected from 1,2 or 3; when m is 1, two LbThe same or different; when m is 2 or 3, a plurality of LaThe same or different;
z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;
X3-X8selected from CR, identically or differently at each occurrencexOr N;
Y1-Y4selected from CR, identically or differently at each occurrenceyOr N;
R，Rx，Ry，R1-R8each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or notA substituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0-20 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;
X3-X8at least one of which is CRxAnd said R isxIs cyano;
Y2and Y3At least one of which is CRyAnd said R isyIs F;
adjacent substituents R, Rx，Ry，R1-R8Can optionally be linked to form a ring.
In this example, the "adjacent substituents R, Rx，Ry，R1-R8Can optionally be linked to form a ring ", is intended to denote a group in which adjacent substituents are present, for example, between two substituents R, two substituents RxIn between, two substituents RyR is1-R8In the above formula (b), any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the invention, wherein Z is selected from O and S.
According to one embodiment of the invention, wherein Z is O.
According to one embodiment of the inventionWherein Y is1-Y4Selected from CR, identically or differently at each occurrenceyAnd Y is2And Y3At least one of which is CRyAnd said R isyIs F.
According to an embodiment of the invention, wherein Y1-Y4Selected from CR, identically or differently at each occurrenceyOr N, and Y2And Y3At least one of which is CRyAnd said R isyIs F.
According to one embodiment of the present invention, wherein Y2And Y3At least one of which is CRyAnd said R isyIs F; y is1-Y4The others of (A) and (B) are selected from CRyWhen R isyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
As used herein, "Y" or "Y" is defined as1-Y4The remainder of (1) refers to the following: when Y is2Is CRyAnd said R isyWhen is F, "Y1-Y4The rest of (1) are Y1And Y3-Y4(ii) a When Y is3Is CRyAnd said R isyWhen is F, "Y1-Y4In the rest of Ry"then refers to Y4And Y1-Y2(ii) a When Y is2And Y3Are all CRyAnd said R isyWhen is F, "Y1-Y4In the rest of Ry"then refers to Y1And Y4。
According to one embodiment of the present invention, wherein Y2And Y3At least one of which is CRyAnd said R isyIs F; y is1-Y4The others of (A) and (B) are selected from CRyWhen R isyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted compounds having 1 to 20 carbon atomsSubstituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.
According to an embodiment of the invention, wherein Y2And Y3At least one of which is CRyAnd said R isyIs F; y is1-Y4The others of (A) and (B) are selected from CRyWhen R isySelected from hydrogen, deuterium, methyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, isopentyl, neopentyl, tert-pentyl, or combinations thereof; optionally, the hydrogens in the above groups are partially or fully deuterated.
According to an embodiment of the invention, wherein Y2And Y3At least one of which is CRyAnd said R isyIs F; y is1-Y4At least one further one of (A) is selected from CRyAnd at least one RyIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, and combinations thereof.
According to an embodiment of the invention, wherein Y2Is CRyAnd said R isyIs fluorine; y is3Is CRy，RySelected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, and combinations thereof.
According to an embodiment of the invention, wherein Y3Is CRyAnd said R isyIs fluorine; y is2Is CRy，RySelected from the group consisting of: deuterium, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 15 carbon atoms, and groups thereofAnd (6) mixing.
According to an embodiment of the invention, wherein X1-X8Selected from C or CR, identically or differently at each occurrencex。
According to an embodiment of the invention, wherein X1-X8At least two of which are CRxAnd said one RxIs cyano, and additionally at least one RxIs selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino groups having from 0 to 20 carbon atoms, and combinations thereof.
According to an embodiment of the invention, wherein X1-X8At least two of which are CRxAnd said one RxIs cyano, and additionally at least one RxIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, hydroxyl groups, mercapto groups, and combinations thereof.
According to an embodiment of the invention, wherein X1-X8At least two of which are CRxAnd said one RxIs cyano, and additionally at least one RxIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, and combinations thereof.
According to an embodiment of the invention, wherein X7And X8All are selected from CRxAnd said one RxIs cyano, another one of said RxIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, and combinations thereof.
According to an embodiment of the invention, wherein X5-X8In (1), at least one is CRxAnd said R isxIs cyano.
According to an embodiment of the invention, wherein X7Is CRxAnd said R isxIs cyano.
According to an embodiment of the invention, wherein X8Is CRxAnd said R isxIs cyano.
According to one embodiment of the invention, wherein R2，R3，R6，R7At least one or at least two or at least three or all selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R2，R3，R6，R7At least one or at least two or at least three or all selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R2，R3，R6，R7At least one or at least two or at least three or all selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, the hydrogens in the above groups are partially or fully deuterated.
According to one embodiment of the invention, wherein R is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.
According to one embodiment of the invention, wherein R is methyl or deuterated methyl.
According to an embodiment of the invention, wherein LaEach occurrence being selected identically or differently from La1-La766Group of wherein La1-La766The specific structure of (a) is as defined in claim 14.
According to an embodiment of the invention, wherein LbEach occurrence being selected identically or differently from Lb1-Lb78Group of wherein Lb1-Lb78The specific structure of (A) is as defined in claim 15.
According to an embodiment of the invention, wherein LbEach occurrence being selected identically or differently from Lb1-Lb80Group of wherein Lb1-Lb80The concrete structure of (3) is as described in claim 15.
According to one embodiment of the invention, wherein the metal complex has Ir (L)a)2(Lb) Structure of (1), LaEach occurrence, identically or differently, of a group selected from La1To La766Any one or any two of the group consisting of,Lbis selected from the group consisting of Lb1To Lb78Any one of the group consisting of wherein La1-La766According to claim 14, Lb1-Lb78The concrete structure of (3) is as described in claim 15.
According to one embodiment of the invention, wherein the metal complex has Ir (L)a)2(Lb) Structure of (1), LaEach occurrence being selected identically or differently from La1To La766Any one or any two of the group consisting of, LbIs selected from the group consisting of Lb1To Lb80Any one of the group consisting of wherein La1-La766According to claim 14, Lb1-Lb80The specific structure of (A) is as defined in claim 15.
According to one embodiment of the invention, wherein the metal complex has Ir (L)a)(Lb)2Structure of (1), LaIs selected from the group consisting of La1To La766Any one of the group consisting of LbEach occurrence being selected identically or differently from Lb1To Lb78Any one or any two of the group consisting of, wherein La1-La766According to claim 14, Lb1-Lb78The specific structure of (A) is as defined in claim 15.
According to one embodiment of the invention, the metal complex has Ir (L)a)(Lb)2Structure of (1), LaIs selected from the group consisting of La1To La766Any one of the group consisting of LbEach occurrence being selected identically or differently from Lb1To Lb80Any one or any two of the group consisting of, wherein La1-La766According to claim 14, Lb1-Lb80The specific structure of (A) is as defined in claim 15.
According to one embodiment of the invention, wherein the metal complex has Ir (L)a)3Structure of (1), LaEach occurrence, identically or differently, of a group selected from La1To La766Any of the groupOne or any two or any three, wherein La1-La766The specific structure of (a) is as defined in claim 14.
According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 360, wherein the specific structures of metal complex 1 to metal complex 360 are described in claim 16.
According to an embodiment of the present invention, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 390, wherein the specific structures of metal complex 1 to metal complex 390 are as defined in claim 16.
According to one embodiment of the present invention, there is disclosed an electroluminescent device, including:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising a metal complex according to any of the preceding embodiments.
According to an embodiment of the present invention, wherein the organic layer including the metal complex in the electroluminescent device is a light-emitting layer.
According to an embodiment of the invention, wherein said light emitting layer of said electroluminescent device is emitting green light.
According to one embodiment of the present invention, wherein at least one first host compound is comprised in the light emitting layer of the electroluminescent device.
According to one embodiment of the present invention, wherein the light emitting layer of the electroluminescent device further comprises at least two host compounds.
According to an embodiment of the invention, wherein at least one of the host compounds in the electroluminescent device comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
According to an embodiment of the present invention, wherein the first host compound in the electroluminescent device has a structure represented by formula 3:
wherein,
Lxeach occurrence 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 on each occurrence, from C, CRvOr N, and at least one of V is C, and with LxConnecting;
u is selected, identically or differently on each occurrence, from C, CRuOr N, and at least one of U is C, and with LxConnecting;
Rvand RuEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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,an ester group, a cyano group, an isocyano group, a hydroxy group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Ar1each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents RvAnd RuCan optionally be linked to form a ring.
In this embodiment, the "adjacent substituents RvAnd RuCan optionally be linked to form a ring ", is intended to denote a group of adjacent substituents therein, e.g. two substituents RvIn between, two substituents RuIn between, two substituents RvAnd RuAnd any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the present invention, wherein the second host compound in the electroluminescent device has a structure represented by formula 3-a to
A structure represented by one of formulas 3-j:
according to one embodiment of the present invention, in the electroluminescent device, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1% to 30% of the total weight of the light-emitting layer.
According to one embodiment of the present invention, in the electroluminescent device, the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 3% -13% of the total weight of the light-emitting layer.
According to another embodiment of the present invention, a combination of compounds is disclosed, the combination of compounds comprising a metal complex according to any one of the preceding embodiments.
In combination with other materials
The materials described herein for use in particular 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 Ser. No. 0161 (paragraph 0132-0161) of US2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced 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 being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the light emitting dopants disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced 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 unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's 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, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.
Materials synthesis example:
the preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limited to, and the synthetic route and the preparation method thereof are as follows:
synthesis example 1: synthesis of Metal Complex 4
A dry 250mL round bottom flask was charged with intermediate 1(2.2g, 7.2mmol), iridium complex 1(3.5g, 5.2mmol), 2-ethoxyethanol (30mL) and DMF (30mL), N in that order2Heating to react for 120h at 110 ℃ under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 4(0.94g, 22.4% yield) as a yellow solid. The product was identified as the target product and had a molecular weight of 805.2.
Synthesis example 2: synthesis of Metal Complex 14
A dry 250mL round bottom flask was charged with intermediate 2(1.5g, 4.9mmol), iridium complex 1(2.9g, 4.0mmol), 2-ethoxyethanol (30mL) and DMF (30mL), N in that order2The reaction is heated at 90 ℃ for 144h under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 14(0.70g, 21.8% yield) as a yellow solid. The product is determined as target product, and has molecular weight805.2。
Synthetic example 3: synthesis of Metal Complex 44
A dry 250mL round bottom flask was charged with intermediate 2(1.6g, 5.2mmol), iridium complex 2(3.1g, 4.0mmol), 2-ethoxyethanol (25mL) and DMF (25mL), N in that order2The reaction is heated for 144h at 90 ℃ under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 44(0.58g, 17.5% yield) as a yellow solid. The product structure is determined as the target product and has the molecular weight of 833.2.
Synthetic example 4: synthesis of Metal Complex 103
A dry 250mL round bottom flask was charged with intermediate 3(1.2g, 3.9mmol), iridium complex 3(2.5g, 3.2mmol), 2-ethoxyethanol (20mL) and DMF (20mL), N in that order2The reaction is heated at 90 ℃ for 144h under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 103(0.85g, 30.9% yield) as a yellow solid. The product structure is determined as the target product and has the molecular weight of 861.2.
Synthesis example 5: synthesis of Metal Complex 389
A dry 250mL round bottom flask was charged with intermediate 4(1.6g, 4.2mmol), iridium complex 4(2.6g, 3.2mmol), 2-ethoxyethanol (25mL) and DMF (25mL) in that order,N2the reaction is heated at 90 ℃ for 144h under protection. After the reaction was cooled, the celite was filtered. Methanol and n-hexane were washed 2 times, respectively, and the yellow solid above the celite was dissolved with dichloromethane, and the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give metal complex 389(0.48g, 15.1% yield) as a yellow solid. The product structure is determined as the target product and has the molecular weight of 993.3.
It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.
Device example 1
First, a glass substrate, having an Indium Tin Oxide (ITO) anode 80nm thick, was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees-8In the case of torr, the evaporation was carried out on the ITO anode in turn by thermal vacuum evaporation at a rate of 0.2-2 a/s. Compound HI was used as Hole Injection Layer (HIL). The compound HT is used as a Hole Transport Layer (HTL). Compound H1 was used as Electron Blocking Layer (EBL). The metal complex 4 of the present invention is then doped in a compound H1 and a compound H2 and co-deposited as a light-emitting layer (EML). On EML, compound H3 acts as a Hole Blocking Layer (HBL). On HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) was evaporated to a thickness of 1nm as an electron injection layer, and 120nm of aluminum as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid and moisture absorber to complete the device.
Device example 2
Device example 2 was carried out in the same manner as in device example 1, except that the metal complex 14 of the present invention was used in place of the metal complex 4 of the present invention in the light-emitting layer (EML).
Device example 3
Device example 3 was carried out in the same manner as in device example 1 except that the metal complex 44 of the present invention was used in place of the metal complex 4 of the present invention in the light-emitting layer (EML).
Device example 4
Device example 4 was implemented in the same manner as in device example 1 except that the metal complex 389 of the present invention was used in the light-emitting layer (EML) instead of the metal complex 4 of the present invention.
Device comparative example 1
Device comparative example 1 was conducted in the same manner as in device example 1 except that the metal complex 4 of the present invention was replaced with the compound GD1 in the light-emitting layer (EML).
Device comparative example 2
Device comparative example 1 was conducted in the same manner as in device example 1 except that the metal complex 4 of the present invention was replaced with the compound GD2 in the light-emitting layer (EML).
Device comparative example 3
Device comparative example 1 was conducted in the same manner as in device example 1 except that the metal complex 4 of the present invention was replaced with the compound GD3 in the light-emitting layer (EML).
The detailed device layer structure and thickness are shown in table 1 below. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
Table 1 device structure of device embodiments
The material structure used in the device is as follows:
the IVL characteristics of the device were measured. At 1000cd/m2The CIE data of the devices, the maximum emission wavelength lambda, were measuredmaxFull width at half maximum (FWHM), voltage (V) and External Quantum Efficiency (EQE). These data are recorded and presented in table 2.
TABLE 2 device data
Discussion:
table 2 shows the device properties of the examples and comparative examples. From the data in Table 2 we find thataIn comparison with comparative example 1 in which the ligand is not substituted, examples 1 and 2 have emission wavelengths blue-shifted by 4 to 5nm and have more saturated green emission. Moreover, the EQE of the devices of example 1 and example 2 reached 24.37% and 24.65%, respectively, which are both higher than 23.39% of comparative example 1, and further improved based on the fact that comparative example 1 is already in the field. In addition, the device voltages of example 1 and example 2 were both reduced by about 0.35V compared to comparative example 1.
At LaY of the ligand2And Y3The spectrum of comparative example 3, in which all the positions are substituted with deuterated methyl groups, is similar to that of examples 1 and 2, but the EQE of comparative example 3 is reduced to a different extent than that of examples 1 and 2, and the device voltage is also higher than that of examples 1 and 2.
At LaY of the ligand1The maximum emission wavelength of comparative example 2 having fluorine substitution at the position was red-shifted by approximately 20nm as compared with examples 1 and 2, and the half-peak widths were respectively widened by 18.5nm and 23.9nm, so that the emission color of comparative example 2 was not saturated. In addition, the EQE of comparative example 2 is somewhat lower than both example 1 and example 2, and the device voltage of comparative example 2 is also slightly higher than that of example 1 and example 2.
The above results show that the metal complexes of the invention with ligands substituted at a specific position F are compared to LaMetal complexation without substitution or substitution of other alkyl or fluorine at the same position of ligand improves device performance, especially reduces voltage and EQEAnd the improvement of the light emitting color saturation.
Examples 3 and 4 are both greatly enhanced, both exhibiting higher EQE, and lower driving voltage, compared to comparative examples 1-3. Among them, the driving voltage of example 3 was reduced by 0.5V, 0.22V and 0.21V, respectively, compared to comparative examples 1 to 3. Example 4 the EQE using a metal complex featuring the present invention reached 26.52%, which is about 13.4%, 15.2% and 14.6% higher than comparative examples 1 to 3, respectively, while the half-peak width of example 4 is much narrower, only 32.3nm, which is at a very high level in the industry.
The results show that compared with metal complexes with fluorine substitution at other positions of the ligand, the metal complex with the F-substituted ligand at a specific position of the invention also improves the device performance, especially improves the luminescent color saturation, narrows the half-peak width, improves the EQE and reduces the voltage.
It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.
Claims (23)
1. A metal complex comprising a metal M, and a ligand L coordinated to the metal MaWherein L isaHas a structure represented by formula 1:
in the formula 1, the first and second groups,
the metal M is selected from metals having a relative atomic mass greater than 40;
z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;
X1-X8selected from C, CR, identically or differently at each occurrencexOr N;
Y1-Y4selected from CR, identically or differently at each occurrenceyOr N;
R，Rx，Ryeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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;
X1-X8at least one of which is CRxAnd said R isxIs cyano;
Y2and Y3At least one of which is CRyAnd said R isyIs F;
adjacent substituents R, RxAnd RyCan optionally be linked to form a ring.
2. The metal complex of claim 1, wherein LaHas a structure represented by one of formulas 1a-1 e:
z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;
X1-X8selected from CR, identically or differently at each occurrencexOr N;
Y1-Y4selected from CR, identically or differently at each occurrenceyOr N;
R，Rx，Ryeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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;
X1-X8at least one of which is CRxAnd said R isxIs cyano;
Y2and Y3At least one of which is CRyAnd said R isyIs F;
adjacent substituents R, RxAnd RyCan optionally be linked to form a ring.
3. The metal complex as claimed in claim 1 or 2, wherein the metal complex has M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein,
the metal M is selected from metals having a relative atomic mass greater than 40; preferably, M is selected, identically or differently on each occurrence, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; more preferably, M is selected, identically or differently on each occurrence, from Pt or Ir;
La、Lband LcAre respectively a first, a second and a third ligand coordinated to the metal M, and LcAnd said LaOr LbAre the same or different; wherein L isa、LbAnd LcOptionally linked to form a multidentate ligand;
m1, 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 2 or more, a plurality of LaThe same or different; when n is equal to 2, two LbThe same or different; when q is equal to 2, two LcThe same or different;
Lband LcA structure, which is the same or different at each occurrence, selected from any one of the group consisting of:
wherein,
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1，CRC1RC2；
Ra，Rb，Rc，RN1，RC1And RC2Each occurrence, the same or different, is 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 hetero having 1 to 20 carbon atomsAn alkyl group, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents Ra，Rb，Rc，RN1，RC1And RC2Can optionally be linked to form a ring.
4. The metal complex according to any one of claims 1 to 3, wherein the metal complex has a structure represented by formula 2:
wherein,
m is selected from 1,2 or 3; when m is 1, two LbThe same or different; when m is 2 or 3, a plurality of LaThe same or different;
z is selected from the group consisting of O, S, Se, NR, CRR and SiRR; when both R are present, both R are the same or different;
X3-X8selected from CR, identically or differently at each occurrencexOr N;
Y1-Y4selected from CR, identically or differently at each occurrenceyOr N;
R，Rx，Ry，R1-R8each occurrence, the same or different, is selected from the group consisting of: hydrogen, the presence 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
X3-X8at least one of which is CRxAnd said R isxIs cyano;
Y2and Y3At least one of which is CRyAnd said R isyIs F;
adjacent substituents R, Rx，Ry，R1-R8Can optionally be linked to form a ring.
5. The metal complex of any one of claims 1 to 4, wherein Z is selected from O and S; preferably, Z is O.
6. A metal complex as claimed in any one of claims 1 to 5, wherein Y is1-Y4Selected from CR, identically or differently at each occurrenceyAnd Y is2And Y3At least one of which is CRyAnd said R isyIs F.
7. The metal complex as claimed in any one of claims 1 to 6, wherein Y is2And Y3At least one of which is CRyAnd said R isyIs F; when Y is1-Y4The remainder of (B) are selected from CRyWhen R isyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;
preferably, when Y is1-Y4The others of (A) and (B) are selected from CRyWhen R isyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
more preferably, when Y is1-Y4The others of (A) and (B) are selected from CRyWhen R isySelected from hydrogen, deuterium, methyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, pentyl, isopentyl, neopentyl, tert-pentyl, or combinations thereof; optionally, the hydrogens in the above groups are partially or fully deuterated.
8. The metal complex as claimed in any one of claims 1 to 6, wherein Y is2And Y3At least one of which is CRyAnd said R isyIs F; y is1-Y4At least one further one of (A) is selected from CRyAnd at least one RyIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, and combinations thereof.
9. The metal complex as claimed in any one of claims 1 to 6, wherein Y is2Is CRyAnd said R isyIs fluorine; and Y is3Is CRySaid R isySelected from the group consisting of: deuterium, substituted or unsubstituted with 1-10A carbon atom alkyl group, a substituted or unsubstituted cycloalkyl group having from 3 to 10 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 15 carbon atoms, and combinations thereof;
or, Y3Is CRyAnd said R isyIs fluorine; and Y is2Is CRySaid R isySelected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, and combinations thereof.
10. The metal complex of claim 1, wherein X1-X8Selected from C or CR, identically or differently at each occurrencex。
11. A metal complex according to claim 1, wherein X1-X8At least two of which are CRxAnd said one RxIs cyano, and additionally at least one RxIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfo groups having from 0 to 20 carbon atomsAcyl, phosphino, and combinations thereof;
preferably, X1-X8At least two of which are CRxAnd said one RxIs cyano, and additionally at least one RxIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, hydroxyl groups, mercapto groups, and combinations thereof;
more preferably, X1-X8At least two of which are CRxAnd said one RxIs cyano, and additionally at least one RxIs selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, and combinations thereof.
12. A metal complex according to any one of claims 1 to 11, wherein X5-X8In (1), at least one is CRxAnd said R isxIs cyano;
preferably, X7Is CRxAnd said R isxIs cyano, or X8Is CRxAnd said R isxIs cyano.
13. A metal complex according to claim 4, wherein R2，R3，R6，R7At least one or at least two or at least three or all are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstitutedSubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;
preferably, R2，R3，R6，R7At least one or at least two or at least three or all are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
more preferably, R2，R3，R6，R7At least one or at least two or at least three or all are selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof; optionally, the hydrogens in the above groups are partially or fully deuterated.
14. A metal complex as claimed in any one of claims 1 to 3, wherein LaEach occurrence being the same or different and selected from any one of the group consisting of:
15. a metal complex as claimed in claim 3 or 14 wherein LbEach occurrence, the same or different, is selected from the group consisting of:
16. the metal complex of claim 15, wherein the metal complex has Ir (L)a)2(Lb) Or Ir (L)a)(Lb)2Or Ir (L)a)3In which L isaEach occurrence being selected identically or differently from La1To La766Any one or any two or any three of the group consisting of, LbIs selected from the group consisting of Lb1To Lb80Any one or two of the group consisting of;
preferably, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 390, wherein metal complex 1 to metal complex 390 has IrLa(Lb)2Wherein two L arebSame wherein LaAnd LbRespectively corresponding to the structures indicated in the following table:
17. an electroluminescent device, comprising:
an anode, a cathode, an anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the metal complex of any one of claims 1 to 16.
18. The electroluminescent device of claim 17, wherein the organic layer comprising the metal complex is a light emitting layer.
19. The electroluminescent device of claim 18 wherein the light emitting layer is green emitting.
20. The electroluminescent device of claim 18 wherein the light-emitting layer comprises at least one first host compound;
preferably, the light-emitting layer further comprises at least two host compounds;
more preferably, at least one of the host compounds comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
21. The electroluminescent device of claim 20, wherein the first host compound has a structure represented by formula 3:
wherein,
Lxeach occurrence of a phaseOr different 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 on each occurrence, from C, CRvOr N, and at least one of V is C, and with LxConnecting;
u is selected, identically or differently on each occurrence, from C, CRuOr N, and at least one of U is C, and with LxConnecting;
Rvand RuEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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;
Ar1each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents RvAnd RuCan optionally be linked to form a ring;
preferably, wherein the second host compound has a structure represented by one of formulae 3-a to 3-j:
22. the electroluminescent device as claimed in claim 20, wherein a metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1-30% of the total weight of the light-emitting layer;
preferably, the weight of the metal complex accounts for 3% -13% of the total weight of the light-emitting layer.
23. A combination of compounds comprising the metal complex of any one of claims 1-16.
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| KR1020210161319A KR20220071124A (en) | 2020-11-23 | 2021-11-22 | Organic electroluminescent material and device thereof |
| JP2021189331A JP2022082519A (en) | 2020-11-23 | 2021-11-22 | Organic electroluminescence materials and their devices |
| DE102021130608.6A DE102021130608B4 (en) | 2020-11-23 | 2021-11-23 | Organic electroluminescent material and device made therefrom |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115448958A (en) * | 2022-11-09 | 2022-12-09 | 吉林奥来德光电材料股份有限公司 | Organic metal compound, organic electroluminescent device containing organic metal compound and application of organic metal compound |
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| CN111518139A (en) * | 2019-02-01 | 2020-08-11 | 北京夏禾科技有限公司 | Organic luminescent material containing cyano-substituted ligand |
| CN111808142A (en) * | 2020-07-09 | 2020-10-23 | 奥来德(上海)光电材料科技有限公司 | Organic phosphorus luminescent compound and preparation method and application thereof |
| CN111825724A (en) * | 2020-07-28 | 2020-10-27 | 奥来德(长春)光电材料科技有限公司 | Phosphorescent iridium complex, preparation method thereof and electroluminescent device |
| CN111875640A (en) * | 2020-07-29 | 2020-11-03 | 奥来德(上海)光电材料科技有限公司 | Organic phosphorus optical compound, preparation method thereof and photoelectric device |
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| CN111518139A (en) * | 2019-02-01 | 2020-08-11 | 北京夏禾科技有限公司 | Organic luminescent material containing cyano-substituted ligand |
| CN111808142A (en) * | 2020-07-09 | 2020-10-23 | 奥来德(上海)光电材料科技有限公司 | Organic phosphorus luminescent compound and preparation method and application thereof |
| CN111825724A (en) * | 2020-07-28 | 2020-10-27 | 奥来德(长春)光电材料科技有限公司 | Phosphorescent iridium complex, preparation method thereof and electroluminescent device |
| CN111875640A (en) * | 2020-07-29 | 2020-11-03 | 奥来德(上海)光电材料科技有限公司 | Organic phosphorus optical compound, preparation method thereof and photoelectric device |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115448958A (en) * | 2022-11-09 | 2022-12-09 | 吉林奥来德光电材料股份有限公司 | Organic metal compound, organic electroluminescent device containing organic metal compound and application of organic metal compound |
| WO2024098677A1 (en) * | 2022-11-09 | 2024-05-16 | 吉林奥来德光电材料股份有限公司 | Organic metal compound, organic electroluminescent device containing same and use |
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