CN117263986A - Organic electroluminescent material and device - Google Patents
Organic electroluminescent material and device Download PDFInfo
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- CN117263986A CN117263986A CN202310724107.XA CN202310724107A CN117263986A CN 117263986 A CN117263986 A CN 117263986A CN 202310724107 A CN202310724107 A CN 202310724107A CN 117263986 A CN117263986 A CN 117263986A
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- 239000000463 material Substances 0.000 title abstract description 116
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 239000003446 ligand Substances 0.000 claims abstract description 86
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 49
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 48
- 229910052751 metal Inorganic materials 0.000 claims abstract description 44
- 239000002184 metal Substances 0.000 claims abstract description 44
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 39
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 22
- 125000001424 substituent group Chemical group 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 238000006467 substitution reaction Methods 0.000 claims description 50
- -1 phosphino, hydroxy, seleno Chemical group 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 28
- 229910052805 deuterium Inorganic materials 0.000 claims description 28
- 239000012044 organic layer Substances 0.000 claims description 28
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 20
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 229910052796 boron Inorganic materials 0.000 claims description 16
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 16
- 150000002825 nitriles Chemical class 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 15
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 14
- 150000002527 isonitriles Chemical class 0.000 claims description 14
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- OBFQBDOLCADBTP-UHFFFAOYSA-N aminosilicon Chemical compound [Si]N OBFQBDOLCADBTP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052711 selenium Inorganic materials 0.000 claims description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 11
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 229910052732 germanium Inorganic materials 0.000 claims description 8
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 6
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 5
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 5
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
- 229910052738 indium Inorganic materials 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 25
- 238000009472 formulation Methods 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 125
- 125000006575 electron-withdrawing group Chemical group 0.000 description 55
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- 239000002019 doping agent Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 125000004429 atom Chemical group 0.000 description 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 230000004888 barrier function Effects 0.000 description 15
- 230000007704 transition Effects 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 230000032258 transport Effects 0.000 description 14
- 229910052698 phosphorus Inorganic materials 0.000 description 13
- 125000003367 polycyclic group Chemical group 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 11
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 11
- 150000003384 small molecules Chemical class 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 9
- 150000004696 coordination complex Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 239000002105 nanoparticle Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000005580 triphenylene group Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 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 description 7
- 229960005544 indolocarbazole Drugs 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 6
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 4
- 230000005693 optoelectronics Effects 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 3
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 3
- OLGGLCIDAMICTA-UHFFFAOYSA-N 2-pyridin-2-yl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=N1 OLGGLCIDAMICTA-UHFFFAOYSA-N 0.000 description 3
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
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- KBBSSGXNXGXONI-UHFFFAOYSA-N phenanthro[9,10-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 KBBSSGXNXGXONI-UHFFFAOYSA-N 0.000 description 1
- RIYPENPUNLHEBK-UHFFFAOYSA-N phenanthro[9,10-b]pyridine Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 RIYPENPUNLHEBK-UHFFFAOYSA-N 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- 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 System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/006—Palladium compounds
-
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Abstract
The present application relates to organic electroluminescent materials and devices. The present disclosure provides a method ofA compound comprising formula IIs a first ligand L of (2) A Wherein X is 1 To X 4 Is C and is fused with a structure selected from the group consisting of: II (II)Formula IIIAnd IVAt ligand L A Wherein X is 1 To X 4 And Z to Z 2 Each of which is C or N; part B is a fused ring system comprising two or more rings; y is Y 1 And Y 2 Each of which is a bridging moiety; k is selected from the group consisting of: direct bond, O, S, N (R) α )、P(R α )、B(R α )、C(R α )、C(R α )(R β ) And Si (R) α )(R β ) The method comprises the steps of carrying out a first treatment on the surface of the Each R, R', R α 、R β 、R A 、R B And R is C Is hydrogen or a general substituent; and L is A Coordinated to a metal M having an atomic mass of at least 40. The present disclosure also provides formulations, OLEDs and consumer products containing the compounds.
Description
Cross reference to related applications
The present application claims priority from U.S. c. ≡119 (e) to U.S. provisional application No. 63/433,171 filed on day 12, month 16 of 2022 and U.S. provisional application No. 63/353,785 filed on day 20 of 2022, the entire contents of which are incorporated herein by reference.
Technical Field
The present disclosure relates generally to organometallic compounds and formulations and various uses thereof, including as emitters in devices such as organic light emitting diodes and related electronic devices.
Background
Optoelectronic devices utilizing organic materials are becoming increasingly popular for a variety of reasons. Many of the materials used to fabricate the devices are relatively inexpensive, so organic photovoltaic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials (e.g., their flexibility) may make them more suitable for specific applications, such as fabrication on flexible substrates. Examples of organic optoelectronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, organic materials can have performance advantages over conventional materials.
OLEDs utilize organic thin films that emit light when a voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, lighting and backlighting.
One application of phosphorescent emissive molecules is in full color displays. Industry standards for such displays require pixels adapted to emit a particular color (referred to as a "saturated" color). In particular, these standards require saturated red, green and blue pixels. Alternatively, the OLED may be designed to emit white light. In conventional liquid crystal displays, the emission from a white backlight is filtered using an absorbing filter to produce red, green and blue emissions. The same technique can also be used for OLEDs. The white OLED may be a single emissive layer (EML) device or a stacked structure. The colors may be measured using CIE coordinates well known in the art.
Disclosure of Invention
In one aspect, the present disclosure provides a compound comprising a first ligand L of formula I A ,Wherein X is 1 To X 4 Is C and is fused with a structure selected from the group consisting of: formula II->Formula III->Formula IV->
In formulas I, II, III and IV: x is X 1 、X 2 、X 3 And X 4 Each of which is independently C or N;
part B is a fused ring system comprising two or more rings, wherein each of the two or more rings is independently a 5-or 6-membered carbocyclic or heterocyclic ring;
Y 1 and Y 2 Independently selected from the group consisting of: o, S, se, CRR ', siRR', geRR ', NR, BR and BRR';
Z、Z 1 and Z 2 Each of which is independently C or N;
k is selected from the group consisting of: direct bond, O, S, N (R) α )、P(R α )、B(R α )、C(R α )、C(R α )(R β ) And Si (R) α )(R β );
R A Represents a di-substitution to the maximum allowable substitution;
R B and R is C Independently represents mono-substitution to maximum allowable substitution, or no substitution;
each R, R', R α 、R β 、R A 、R B And R is C Independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silicon, germanium, boron, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, hydroxy, seleno, and combinations thereof;
L A Coordinated to a metal M having an atomic mass of at least 40;
m may be coordinated to other ligands;
L A can be conjugated with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands; and is also provided with
Any two substituents may be joined or fused to form a ring, provided that if Z 1 And Z 2 Each is C, then Y 1 And Y 2 Not both are S.
In another aspect, the present disclosure provides a formulation comprising a first ligand L comprising formula I as described herein A Is a compound of (a).
In yet another aspect, the present disclosure provides an OLED having an organic layer,the organic layer comprises a first ligand L comprising formula I as described herein A Is a compound of (a).
In yet another aspect, the present disclosure provides a consumer product comprising an OLED having an organic layer comprising a first ligand L comprising formula I as described herein A Is a compound of (a).
Drawings
Fig. 1 shows an organic light emitting device.
Fig. 2 shows an inverted organic light emitting device without a separate electron transport layer.
Fig. 3 shows photoluminescence spectra of an example of the invention measured in PMMA.
Detailed Description
A. Terminology
Unless otherwise specified, the following terms used herein are defined as follows:
As used herein, the term "organic" includes polymeric materials and small molecule organic materials that can be used to fabricate organic optoelectronic devices. "Small molecule" refers to any organic material that is not a polymer, and may be substantial in nature. In some cases, the small molecule may include a repeating unit. For example, the use of long chain alkyl groups as substituents does not remove a molecule from the "small molecule" class. Small molecules may also be incorporated into the polymer, for example as pendant groups on the polymer backbone or as part of the backbone. Small molecules can also act as the core of a dendrimer, which consists of a series of chemical shells built on the core. The core moiety of the dendrimer may be a fluorescent or phosphorescent small molecule emitter. Dendrimers may be "small molecules" and all dendrimers currently used in the OLED field are considered small molecules.
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" over "a second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed over" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photosensitive" when it is believed that the ligand contributes directly to the photosensitive properties of the emissive material. When the ligand is considered not to contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary", but the ancillary ligand may alter the properties of the photosensitive ligand.
As used herein, and as will be generally understood by those of skill in the art, if the first energy level is closer to the vacuum energy level, then the first "highest occupied molecular orbital" (Highest Occupied Molecular Orbital, HOMO) or "lowest unoccupied molecular orbital" (Lowest Unoccupied Molecular Orbital, LUMO) energy level is "greater than" or "higher than" the second HOMO or LUMO energy level. Since Ionization Potential (IP) is measured as a negative energy relative to the vacuum level, a higher HOMO level corresponds to an IP with a smaller absolute value (less negative). Similarly, a higher LUMO energy level corresponds to an Electron Affinity (EA) with a smaller absolute value (less negative EA). On a conventional energy level diagram with vacuum energy level on top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. The "higher" HOMO or LUMO energy level appears closer to the top of this figure than the "lower" HOMO or LUMO energy level.
As used herein, and as will be generally understood by those of skill in the art, a first work function is "greater than" or "higher than" a second work function if the first work function has a higher absolute value. Since work function is typically measured as a negative number relative to the vacuum level, this means that the "higher" work function is more negative (more negative). On a conventional energy level diagram with the vacuum energy level on top, a "higher" work function is illustrated as being farther from the vacuum energy level in a downward direction. Thus, the definition of HOMO and LUMO energy levels follows a different rule than work function.
The terms "halo", "halogen" and "halo" are used interchangeably and refer to fluoro, chloro, bromo and iodo.
The term "acyl" refers to a substituted carbonyl (C (O) -R s )。
The term "ester" refers to a substituted oxycarbonyl (-O-C (O) -R) s or-C (O) -O-R s ) A group.
The term "ether" means-OR s A group.
The terms "thio" or "thioether" are used interchangeably and refer to-SR s A group.
The term "seleno" refers to-SeR s A group.
The term "sulfinyl" refers to-S (O) -R s A group.
The term "sulfonyl" refers to-SO 2 -R s A group.
The term "phosphino" refers to-P (R s ) 3 A group wherein each R s May be the same or different.
The term "silicon-based" refers to-Si (R s ) 3 Groups, where each R s May be the same or different.
The term "germanium group" refers to-Ge (R) s ) 3 Groups, where each R s May be the same or different.
The term "boron group" means-B (R s ) 2 A group or Lewis addition product-B (R) s ) 3 A group, wherein R is s May be the same or different.
In each of the above, R s May be hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silicon based, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combinations thereof. Preferred R s Selected from the group consisting of: alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
The term "alkyl" refers to and includes straight and branched chain alkyl groups. Preferred alkyl groups are those containing from one to fifteen carbon atoms and include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2-dimethylpropyl, and the like. In addition, alkyl groups may be optionally substituted.
The term "cycloalkyl" refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms and include cyclopropyl, cyclopentyl, cyclohexyl, bicyclo [3.1.1] heptyl, spiro [4.5] decyl, spiro [5.5] undecyl, adamantyl, and the like. In addition, cycloalkyl groups may be optionally substituted.
The term "heteroalkyl" or "heterocycloalkyl" refers to an alkyl or cycloalkyl group, respectively, having at least one carbon atom replaced with a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, si and Se, preferably O, S or N. In addition, heteroalkyl or heterocycloalkyl groups may be optionally substituted.
The term "alkenyl" refers to and includes both straight and branched alkenyl groups. Alkenyl is essentially an alkyl group comprising at least one carbon-carbon double bond in the alkyl chain. Cycloalkenyl is essentially cycloalkyl including at least one carbon-carbon double bond in the cycloalkyl ring. The term "heteroalkenyl" as used herein refers to an alkenyl group having at least one carbon atom replaced with a heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, si and Se, preferably O, S or N. Preferred alkenyl, cycloalkenyl or heteroalkenyl groups are those containing from two to fifteen carbon atoms. In addition, alkenyl, cycloalkenyl, or heteroalkenyl groups may be optionally substituted.
The term "alkynyl" refers to and includes both straight and branched chain alkynyl groups. Alkynyl is essentially an alkyl group that includes at least one carbon-carbon triple bond in the alkyl chain. Preferred alkynyl groups are those containing from two to fifteen carbon atoms. In addition, alkynyl groups may be optionally substituted.
The term "aralkyl" or "arylalkyl" is used interchangeably and refers to an alkyl group substituted with an aryl group. In addition, aralkyl groups may be optionally substituted.
The term "heterocyclyl" refers to and includes aromatic and non-aromatic cyclic groups containing at least one heteroatom. Optionally, the at least one heteroatom is selected from O, S, N, P, B, si and Se, preferably O, S or N. Aromatic heterocyclic groups may be used interchangeably with heteroaryl. Preferred non-aromatic heterocyclic groups are heterocyclic groups containing 3 to 7 ring atoms including at least one heteroatom and include cyclic amines such as morpholinyl, piperidinyl, pyrrolidinyl, and the like, and cyclic ethers/sulfides such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. In addition, the heterocyclic group may be optionally substituted.
The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. The polycyclic ring may have two or more rings in common in which two carbons are two adjoining rings (the rings being "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. Preferred aryl groups are those containing from six to thirty carbon atoms, preferably from six to twenty carbon atoms, more preferably from six to twelve carbon atoms. Particularly preferred are aryl groups having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, triphenylene, fluorene and naphthalene. In addition, aryl groups may be optionally substituted.
The term "heteroaryl" refers to and includes monocyclic aromatic groups and polycyclic aromatic ring systems that include at least one heteroatom. Heteroatoms include, but are not limited to O, S, N, P, B, si and Se. In many cases O, S or N are preferred heteroatoms. The monocyclic heteroaromatic system is preferably a monocyclic ring having 5 or 6 ring atoms, and the ring may have one to six heteroatoms. The heteropolycyclic ring system may have two or more rings in which two atoms are common to two adjoining rings (the rings being "fused"), wherein at least one of the rings is heteroaryl, e.g., the other rings may be cycloalkyl, cycloalkenyl, aryl, heterocyclic, and/or heteroaryl. The heteropolycyclic aromatic ring system may have one to six heteroatoms in each ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing from three to thirty carbon atoms, preferably from three to twenty carbon atoms, more preferably from three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, diazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene (xanthene), acridine, phenazine, phenothiazine, phenoxazine, benzofurandipyridine, benzothiophene pyridine, thienodipyridine, benzoselenophene dipyridine, dibenzofuran, dibenzoselenium, carbazole, indolocarbazole, benzimidazole, triazine, 1, 2-borazine, 1-boron-nitrogen, 1-nitrogen, 4-boron-nitrogen, boron-nitrogen-like compounds, and the like. In addition, heteroaryl groups may be optionally substituted.
Of the aryl and heteroaryl groups listed above, triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and their respective corresponding aza analogues, are of particular interest.
The terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclyl, aryl, and heteroaryl as used herein are independently unsubstituted or independently substituted with one or more common substituents.
In many cases, the typical substituents are selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silicon, germanium, boron, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, seleno, sulfinyl, sulfonyl, phosphino, hydroxyl, and combinations thereof.
In some cases, preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silicon, germanium, boron, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, hydroxy, and combinations thereof.
In some cases, more preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silicon-based, aryl, heteroaryl, thio, and combinations thereof.
In other cases, the most preferred general substituents are selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
The terms "substituted" and "substituted" refer to substituents other than H bonded to the relevant position, such as carbon or nitrogen. For example, when R 1 When single substitution is represented, then one R 1 It must not be H (i.e., substitution). Similarly, when R 1 When two are substituted, two R 1 It must not be H. Similarly, when R 1 R represents zero or no substitution 1 For example, it may be hydrogen of available valence of the ring atoms, such as carbon atoms of benzene and nitrogen atoms in pyrrole, or for ring atoms having a fully saturated valence, it may simply represent none, such as nitrogen atoms in pyridine. The maximum number of substitutions possible in the ring structure will depend on the total number of available valences in the ring atom.
As used herein, "combination thereof" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, alkyl and deuterium can combine to form a partially or fully deuterated alkyl group; halogen and alkyl may combine to form a haloalkyl substituent; and halogen, alkyl and aryl may combine to form a haloaralkyl. In one example, the term substitution includes a combination of two to four of the listed groups. In another example, the term substitution includes a combination of two to three groups. In yet another example, the term substitution includes a combination of two groups. Preferred combinations of substituents are combinations containing up to fifty atoms other than hydrogen or deuterium, or combinations comprising up to forty atoms other than hydrogen or deuterium, or combinations comprising up to thirty atoms other than hydrogen or deuterium. In many cases, a preferred combination of substituents will include up to twenty atoms that are not hydrogen or deuterium.
The term "aza" in the fragments described herein, i.e., aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic ring may be replaced with a nitrogen atom, for example and without limitation, aza-triphenylene encompasses dibenzo [ f, H ] quinoxaline and dibenzo [ f, H ] quinoline. Other nitrogen analogs of the aza-derivatives described above can be readily envisioned by those of ordinary skill in the art, and all such analogs are intended to be encompassed by the terms as set forth herein.
As used herein, "deuterium" refers to an isotope of hydrogen. Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. patent No. 8,557,400, patent publication No. WO 2006/095951, and U.S. patent application publication No. US 2011/0037057 (which are incorporated herein by reference in their entirety) describe the preparation of deuterium-substituted organometallic complexes. Further reference is made to Yan Ming (Ming Yan) et al, tetrahedron 2015,71,1425-30 and Azrote (Atzrodt) et al, germany application chemistry (Angew. Chem. Int. Ed.) (reviewed) 2007,46,7744-65, which is incorporated by reference in its entirety, describes the deuteration of methylene hydrogen in benzylamine and the efficient pathway of replacement of aromatic ring hydrogen with deuterium, respectively.
It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or as if it were an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of naming substituents or linking fragments are considered equivalent.
In some cases, a pair of adjacent substituents may optionally be joined or fused into a ring. Preferred rings are five-, six-, or seven-membered carbocycles or heterocycles, including both cases where a portion of the ring formed by the pair of substituents is saturated and a portion of the ring formed by the pair of substituents is unsaturated. As used herein, "adjacent" means that the two substituents involved can be next to each other on the same ring, or on two adjacent rings having two nearest available substitutable positions (e.g., the 2, 2' positions in biphenyl or the 1, 8 positions in naphthalene) so long as they can form a stable fused ring system.
B. Compounds of the present disclosure
In one aspect, the present disclosure provides a compound comprising a first ligand L of formula I A ,
Wherein X is 1 To X 4 Is C and is fused with a structure selected from the group consisting of: formula II->Formula III->And formula IV->
In formulas I, II, III and IV: x is X 1 、X 2 、X 3 And X 4 Each of which is independently C or N;
part B is a fused ring system comprising two or more rings, wherein each of the two or more rings is independently a 5-or 6-membered carbocyclic or heterocyclic ring;
Y 1 and Y 2 Independently selected from the group consisting of: o (O),S, se, CRR ', siRR', geRR ', NR, BR and BRR';
Z、Z 1 and Z 2 Each of which is independently C or N;
k is selected from the group consisting of: direct bond, O, S, N (R) α )、P(R α )、B(R α )、C(R α )、C(R α )(R β ) And Si (R) α )(R β );
R A Represents a di-substitution to the maximum allowable substitution;
R B and R is C Independently represents mono-substitution to maximum allowable substitution, or no substitution;
each R, R', R α 、R β 、R A 、R B And R is C Independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein;
L A coordinated to a metal M having an atomic mass of at least 40;
m may be coordinated to other ligands;
L A can be conjugated with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands; and is also provided with
Any two substituents may be joined or fused to form a ring, provided that if Z 1 And Z 2 Each is C, then Y 1 And Y 2 Not both are S.
In the inclusion of a first ligand L as described herein A Of the compounds of (3), L A Is joined to the metal M by a dashed line, and the structures of formulae II, III and IV are joined to X by a dashed line 1 To X 4 Is engaged.
In some embodiments, each R, R', R A 、R B And R is C Independently hydrogen or a substituent selected from the group consisting of the preferred general substituents described herein. In some embodiments, each R, R', R A 、R B And R is C Independently hydrogen or a substituent selected from the group consisting of the more preferred general substituents described herein. In some embodiments, each R, R', R A 、R B And R is C Independently hydrogen or a substituent selected from the group consisting of the most preferred general substituents described herein.
In some embodiments, the metal M is selected from the group consisting of: ir, rh, re, ru, os, pt, pd, ag, au and Cu. In some embodiments, the metal M is Ir. In some embodiments, the metal M is Pt or Pd.
In some embodiments, Z is C. In some embodiments, Z is N.
In some embodiments, X 1 To X 4 Each of which is C.
In some embodiments, X 1 To X 4 At least one of which is N. In some embodiments, X 1 To X 4 Exactly one of (2) is N.
In some embodiments, moiety B is a fused ring system comprising two or more rings, wherein each ring is independently a 5-or 6-membered aromatic or heteroaromatic ring.
In some embodiments, part B is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, benzoxazole, benzothiophene, benzothiazole, benzoselenophene, indene, indole, benzimidazole, carbazole, dibenzofuran, dibenzothiophene, quinoxaline, phthalazine, phenanthrene, phenanthridine, and fluorene. In some embodiments, part B is naphthalene.
In some embodiments, two R B Joined to form a 5-or 6-membered aromatic or heteroaromatic ring. In some embodiments, the 5-or 6-membered aromatic or heteroaromatic ring may be benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, or thiazole.
In some embodiments, moiety B is a polycyclic fused ring structure. In some embodiments, moiety B is a polycyclic fused ring structure comprising at least three fused rings. In some embodiments, the polycyclic fused ring structure has two 6 membered rings and one 5 membered ring. In some such embodiments, the 5-membered ring is fused to the ring coordinated to metal M, and the second 6-membered ring is fused to the 5-membered ring. In some embodiments, part B is selected from the group consisting of: dibenzofuran, dibenzothiophene, dibenzoselenophene, and aza variants thereof. In some such embodiments, moiety B may be further substituted at the ortho or meta position of the O, S or Se atom independently with a substituent selected from the group consisting of: deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In some such embodiments, the aza variant contains exactly one N atom at the 6 position (O, S or ortho to Se) and a substituent at the 7 position (O, S or meta to Se).
In some embodiments, moiety B is a polycyclic fused ring structure comprising at least four fused rings. In some embodiments, the polycyclic fused ring structure comprises three 6 membered rings and one 5 membered ring. In some such embodiments, the 5-membered ring is fused to a ring coordinated to the metal M, the second 6-membered ring is fused to the 5-membered ring, and the third 6-membered ring is fused to the second 6-membered ring. In some such embodiments, the third 6-membered ring is further substituted with a substituent selected from the group consisting of: deuterium, fluorine, nitrile, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
In some embodiments, moiety B is a polycyclic fused ring structure comprising at least five fused rings. In some embodiments, the polycyclic fused ring structure comprises four 6-membered rings and one 5-membered ring or three 6-membered rings and two 5-membered rings. In some embodiments comprising two 5-membered rings, the 5-membered rings are fused together. In some embodiments comprising two 5-membered rings, the 5-membered rings are separated by at least one 6-membered ring. In some embodiments having one 5-membered ring, the 5-membered ring is fused to a ring coordinated to metal M, the second 6-membered ring is fused to the 5-membered ring, the third 6-membered ring is fused to the second 6-membered ring, and the fourth 6-membered ring is fused to the third 6-membered ring.
In some embodiments, part B is an aza form of the polycyclic fused ring described above. In some such embodiments, moiety B contains exactly one aza N atom. In some such embodiments, moiety B contains exactly two aza N atoms, which may be in one ring or in two different rings. In some such embodiments, the ring having the aza N atom is separated from the metal M atom by at least two other rings. In some such embodiments, the ring with the aza N atom is separated from the metal M atom by at least three other rings. In some such embodiments, each ortho position to the aza N atom is substituted.
In some embodiments, X 1 And X 2 Is C and is bonded by a dashed line to a structure selected from the group consisting of formula II, formula III and formula IV.
In some embodiments, X 2 And X 3 Is C and is bonded by a dashed line to a structure selected from the group consisting of formula II, formula III and formula IV.
In some embodiments, X 3 And X 4 Is C and is bonded by a dashed line to a structure selected from the group consisting of formula II, formula III and formula IV.
In some embodiments, formula IIBy dotted line and X 1 To X 4 Is bonded to the adjacent two of the substrate.
In some embodiments, formula III By dotted line and X 1 To X 4 Is bonded to the adjacent two of the substrate.
In some embodiments, formula IVBy dotted line and X 1 To X 4 Is bonded to the adjacent two of the substrate.
In some embodiments, Y 1 Is O, S or Se. In some embodiments, Y 1 Is O or S. In some embodiments, Y 1 Is O. In some embodiments, Y 1 Is S.
In some embodiments, Y 1 Selected from the group consisting of: CRR ', siRR', geRR ', and BRR'.
In some embodiments, Y 1 Is NR or BR.
In some embodiments, Y 2 Is O, S or Se. In some embodiments, Y 2 Is O or S. In some embodiments, Y 2 Is O. At the position ofIn some embodiments, Y 2 Is S.
In some embodiments, Y 2 Selected from the group consisting of: CRR ', siRR', geRR ', and BRR'.
In some embodiments, Y 2 Is NR or BR.
In some embodiments, Y 1 Is S and Y 2 Is O. In some embodiments, Y 1 And Y 2 Is not Se. In some embodiments, Y 1 And Y 2 Neither Se.
In some embodiments, one of R or R' (if present) and one R B Joined to form a loop. In some embodiments, one R (if present) and one R B Joined to form a loop. In some embodiments, one R' (if present) and one R B Joined to form a loop.
In some embodiments, Z 1 And Z 2 Is C. In some embodiments, Z 1 Is C and Z 2 Is N. In some embodiments, Z 1 Is N, and Z 2 Is C.
In some embodiments, at least one R C Not hydrogen or deuterium.
In some embodiments, at least one R C Selected from the group consisting of: alkyl groups, silicon groups, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof. In some embodiments, at least one R C Is an alkyl group containing at least 3 carbon atoms which may be partially or fully fluorinated or partially or fully deuterated.
In some embodiments, at least one R that is not part of formula II, formula III, or formula IV A Not hydrogen or deuterium.
In some embodiments, at least one R B Not hydrogen or deuterium.
In some embodiments of the compounds, R A 、R B Or R is C Is an electron withdrawing group in list EWG 1 as defined herein. In some embodiments of the compounds, R A 、R B Or R is C At least one of (a)And are electron withdrawing groups in the list EWG 2 as defined herein. In some embodiments of the compounds, R A 、R B Or R is C Is an electron withdrawing group in list EWG 3 as defined herein. In some embodiments of the compounds, R A 、R B Or R is C Is an electron withdrawing group in the list EWG 4 as defined herein. In some embodiments of the compounds, R A 、R B Or R is C Is an electron withdrawing group in a list Pi-EWG as defined herein.
In some embodiments of the compound, one R A Is an electron withdrawing group in list EWG 1 as defined herein. In some embodiments of the compound, one R A Is an electron withdrawing group in list EWG 2 as defined herein. In some embodiments of the compound, one R A Is an electron withdrawing group in list EWG 3 as defined herein. In some embodiments of the compound, one R A Is an electron withdrawing group in list EWG 4 as defined herein. In some embodiments of the compound, one R A Is an electron withdrawing group in a list Pi-EWG as defined herein.
In some embodiments of the compound, one R B Is an electron withdrawing group in list EWG 1 as defined herein. In some embodiments of the compound, one R B Is an electron withdrawing group in list EWG 2 as defined herein. In some embodiments of the compound, one R B Is an electron withdrawing group in list EWG 3 as defined herein. In some embodiments of the compound, one R B Is an electron withdrawing group in list EWG 4 as defined herein. In some embodiments of the compound, one R B Is an electron withdrawing group in a list Pi-EWG as defined herein.
In some embodiments of the compound, one R C Is an electron withdrawing group in list EWG 1 as defined herein. In some embodiments of the compound, one R C Is an electron withdrawing group in list EWG 2 as defined herein. In some embodiments of the compoundsOne R C Is an electron withdrawing group in list EWG 3 as defined herein. In some embodiments of the compound, one R C Is an electron withdrawing group in list EWG 4 as defined herein. In some embodiments of the compound, one R C Is an electron withdrawing group in a list Pi-EWG as defined herein.
In some embodiments of the compounds, ligand L A Comprising electron withdrawing groups in the list EWG 1 as defined herein. In some embodiments of the compounds, ligand L A Comprising electron withdrawing groups in the list EWG 2 as defined herein. In some embodiments of the compounds, ligand L A Comprising electron withdrawing groups in the list EWG 3 as defined herein. In some embodiments of the compounds, ligand L A Comprising electron withdrawing groups in the list EWG 4 as defined herein. In some embodiments of the compounds, ligand L A Comprising electron withdrawing groups in a list Pi-EWG as defined herein.
In some embodiments of the compounds, the compounds comprise electron withdrawing groups in the list EWG 1 as defined herein. In some embodiments of the compounds, the compounds comprise electron withdrawing groups in the list EWG 2 as defined herein. In some embodiments of the compounds, the compounds comprise electron withdrawing groups in the list EWG 3 as defined herein. In some embodiments of the compounds, the compounds comprise electron withdrawing groups in the list EWG 4 as defined herein. In some embodiments of the compounds, the compounds comprise electron withdrawing groups in the list Pi-EWG as defined herein.
In some embodiments, the electron withdrawing group generally comprises one or more highly electronegative elements including, but not limited to, fluorine, oxygen, sulfur, nitrogen, chlorine, and bromine.
In some embodiments of the compounds, the electron withdrawing group has a Hammett constant (Hammett constant) greater than 0. In some embodiments, the Hammett constant of the electron withdrawing group is equal to or greater than 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, or 1.1.
In some embodiments, the electron withdrawing group is selected from the following structuresGroup (list EWG 1): F. CF (compact flash) 3 、CN、COCH 3 、CHO、COCF 3 、COOMe、COOCF 3 、NO 2 、SF 3 、SiF 3 、PF 4 、SF 5 、OCF 3 、SCF 3 、SeCF 3 、SOCF 3 、SeOCF 3 、SO 2 F、SO 2 CF 3 、SeO 2 CF 3 、OSeO 2 CF 3 、OCN、SCN、SeCN、NC、 + N(R k2 ) 3 、(R k2 ) 2 CCN、(R k2 ) 2 CCF 3 、CNC(CF 3 ) 2 、BR k3 R k2 Substituted or unsubstituted dibenzoborole, 1-substituted carbazole, 1, 9-substituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridoxine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketone, carboxylic acid, ester, nitrile, isonitrile, sulfinyl, sulfonyl, partially and fully fluorinated alkyl, partially and fully fluorinated aryl, partially and fully fluorinated heteroaryl, cyano-containing alkyl, cyano-containing aryl, cyano-containing heteroaryl, isocyanate,
Wherein Y is G Selected from the group consisting of: BR (BR) e 、NR e 、PR e 、O、S、Se、C=O、S=O、SO 2 、CR e R f 、SiR e R f And GeR e R f The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with
R k1 Each independently represents mono-substitution to maximum permissible substitution, or no substitution;
Wherein R is k1 、R k2 、R k3 、R e And R is f Independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein.
In some embodiments, the electron withdrawing group is selected from the group consisting of the following structures (list EWG 2):/>
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in some embodiments, the electron withdrawing group is selected from the group consisting of the following structures (list EWG 3):
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in some embodiments, the electron withdrawing group is selected from the group consisting of the following structures (list EWG 4):
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in some embodiments, the electron withdrawing group is a pi electron deficient electron withdrawing group. In some embodiments, the Pi electron-deficient electron withdrawing group is selected from the group consisting of the following structures (list Pi-EWG): CN, COCH 3 、CHO、COCF 3 、COOMe、COOCF 3 、NO 2 、SF 3 、SiF 3 、PF 4 、SF 5 、OCF 3 、SCF 3 、SeCF 3 、SOCF 3 、SeOCF 3 、SO 2 F、SO 2 CF 3 、SeO 2 CF 3 、OSeO 2 CF 3 、OCN、SCN、SeCN、NC、 + N(R k1 ) 3 、BR k1 R k2 Substituted or unsubstituted dibenzoboroles, 1-substituted carbazole, 1, 9-substituted carbazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyridazine, substituted or unsubstituted triazine, substituted or unsubstituted oxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted thiazole, substituted or unsubstituted benzothiazole, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, ketone, carboxylic acid, ester, nitrile, isonitrile, sulfinyl, sulfonyl, partially and fully fluorinated aryl, partially and fully fluorinated heteroaryl, cyano-containing aryl, cyano-containing heteroaryl, isocyanate,
Wherein the variables are the same as previously defined.
In some embodiments, ligand L A Selected from the group consisting of the structures of table 1 below:
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wherein Z is 1 '、Z 2 '、Z 3 ' and Z 4 Each of' is independently C or N; w is selected from the group consisting of: BR, BRR ', NR, PR, P (O) R, O, S, se, C = O, C = S, C =se, c=nr, c=crr', s= O, SO 2 CR, CRR ', siRR ', and GeRR '; each R is CC Independently represents mono-substitution to maximum permissible substitution, or no substitution; each R is CC Independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; the remaining variables are the same as previously defined; and is also provided with
Any two substituents may be joined or fused to form a ring.
In some embodiments, ligand L A Selected from the group consisting of the structures of the following list 2:
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wherein:
Y 3 selected from the group consisting of: o, S, se, CRR ', siRR', geRR ', NR, BR and BRR';
Z 3 and Z 4 Each of which is independently C or N;
R BB represents mono-substitution to maximum allowable substitution, or no substitution; and is also provided with
Each R is BB Independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein.
In some embodiments, ligand L A Selected from L Ai-w-m Wherein i is an integer of 1 to 4320, and w is 1 to 35, and m is an integer from 1 to 52;
wherein L is Ai-w-1 To L Ai-w-52 Is defined in the following table 3:
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wherein for each w in 1 to 35Y 1 And Y 2 Defined in the following table 4:
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wherein for L A1 To L A4320 Each L of (a) Ai ,R E 、R F And G is defined in the following table 5:
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wherein R is 1 To R 72 Has the structure defined in the following table 6:
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and is also provided with
Wherein G is 1 To G 20 Has the following Table 7Is characterized by comprising the following structure:
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in some embodiments, the compound has the formula M (L A ) p (L B ) q (L C ) r Wherein L is B And L C Each is a bidentate ligand; and wherein p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and p+q+r is the oxidation state of the metal M.
In some embodiments, the compound has a formula selected from the group consisting of: ir (L) A ) 3 、Ir(L A )(L B ) 2 、Ir(L A ) 2 (L B )、Ir(L A ) 2 (L C ) And Ir (L) A )(L B )(L C ) The method comprises the steps of carrying out a first treatment on the surface of the And wherein L is A 、L B And L C Different from each other.
In some embodiments, L B Is a substituted or unsubstituted phenylpyridine, and L C Is a substituted or unsubstituted acetylacetonate.
In some embodiments, the compound has the formula Pt (L A )(L B ) The method comprises the steps of carrying out a first treatment on the surface of the And wherein L is A And L B May be the same or different. In some embodiments, L A And L B To form a tetradentate ligand.
In some embodiments, L B And L C Each independently selected from the group consisting of the structures of the following list 8:
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wherein T is selected from the group consisting of B, al, ga, and In;
Wherein K is 1 ' is a direct bond or is selected from NR e 、PR e O, S and Se;
wherein each Y 1 To Y 13 Independently selected from the group consisting of carbon and nitrogen;
wherein Y' is selected from the group consisting of: b R e 、N R e 、P R e 、O、S、Se、C=O、S=O、SO 2 、CR e R f 、SiR e R f And GeR e R f ;
Wherein R is e And R is f Can be fused or joined to form a ring;
wherein each R is a 、R b 、R c And R is d May independently represent monosubstituted to the largest possible number of substitutions, or unsubstituted;
wherein each R is a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d 、R e And R is f Independently hydrogen or a substituent selected from the group consisting of the general substituents defined herein; and is also provided with
Wherein R is a1 、R b1 、R c1 、R d1 、R a 、R b 、R c And R is d Any two substituents of (a) may be fused or joined to form a ring or to form a multidentate ligand.
In some embodiments, L B And L C Each independently selected from the group consisting of the structures of the following list 9:
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wherein R is a '、R b '、R c '、R d ' and R e ' each independently represents zero substitution, mono substitution, or up to maximum permissible substitution for its associated ring;
wherein R is a1 、R b1 、R c1 、R a '、R b '、R c '、R d ' and R e ' each independently is hydrogen or a substituent selected from the group consisting of the general substituents as defined herein; and is also provided with
Wherein R is a '、R b '、R c '、R d ' and R e Any two substituents in' may be fused or joined to form a ring or to form a multidentate ligand.
In some embodiments, the compound may have the formula Ir (L A ) 3 Ir (L) A )(L Bk ) 2 Ir (L) A ) 2 (L Bk ) Ir (L) Ai-w-m )(L B ) 2 Ir (L) Ai-w-m ) 2 (L B ) Ir (L) A ) 2 (L Cj-I ) Ir (L) A ) 2 (L Cj-II ) Ir (L) A )(L Bk )(L Cj-I ) Ir (L) A )(L Bk )(L Cj-II ) Ir (L) Ai-w-m )(L Bk )(L Cj-I ) Or Ir (L) Ai-w-m )(L Bk )(L Cj-II ) Wherein L is A Are ligands as defined herein for formula I; l (L) Bk Defined herein; and L is Cj-I And L Cj-II Each is defined herein.
In some embodiments, L A Can be selected from L Ai-w-m Wherein i is an integer from 1 to 4320; w is an integer of 1 to 35, m is an integer of 1 to 52; and L is B Can be selected from L Bk Wherein k is an integer from 1 to 474; and L is C Can be selected from L Cj-I Or L Cj-II Wherein j Is an integer from 1 to 1416;
wherein:
when the compound has the formula Ir (L Ai-w-m ) 3 In the case of a compound selected from Ir (L) A1-1-1 ) 3 To Ir (L) A4320-35-52 ) 3 A group of groups;
when the compound has the formula Ir (L Ai-w-m )(L Bk ) 2 In the case of a compound selected from Ir (L) A1-1-1 )(L B1 ) 2 To Ir (L) A4320-35-52 )(L B474 ) 2 A group of groups;
when the compound has the formula Ir (L Ai-w-m ) 2 (L Bk ) In the case of a compound selected from Ir (L) A1-1-1 ) 2 (L B1 ) To Ir (L) A4320-35-52 ) 2 (L B474 ) A group of groups;
when the compound has the formula Ir (L Ai-w-m ) 2 (L Cj-I ) In the case of a compound selected from Ir (L) A1-1-1 ) 2 (L C1-I ) To Ir (L) A43320-35-52 ) 2 (L C1416-I ) A group of groups; and is also provided with
When the compound has the formula Ir (L Ai-w-m ) 2 (L Cj-II ) In the case of a compound selected from Ir (L) A1-1-1 ) 2 (L C1-II ) To Ir (L) A4320-35-52 ) 2 (L C1416-II ) A group of groups;
wherein each L Bk Having the structure defined in the following list 10:
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wherein each L Cj-I With the basisIs of the structure of (a)The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with
Each L Cj-II With the basisWherein for L Cj-I And L Cj-II Each L of (a) Cj ,R 201 And R is 202 Each independently defined in the following list 11:
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Wherein R is D1 To R D246 Having the structure defined in the following table 12:
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in some embodiments, the compound is selected from only L thereof Bk A group consisting of those compounds corresponding to one of: l (L) B1 、L B2 、L B18 、L B28 、L B38 、L B108 、L B118 、L B122 、L B124 、L B126 、L B128 、L B130 、L B132 、L B134 、L B136 、L B138 、L B140 、L B142 、L B144 、L B156 、L B158 、L B160 、L B162 、L B164 、L B168 、L B172 、L B175 、L B204 、L B206 、L B214 、L B216 、L B218 、L B220 、L B222 、L B231 、L B233 、L B235 、L B237 、L B240 、L B242 、L B244 、L B246 、L B248 、L B250 、L B252 、L B254 、L B256 、L B258 、L B260 、L B262 、L B264 、L B265 、L B266 、L B267 、L B268 、L B269 And L B270 。
In some embodiments, the compound is selected from only L thereof Bk A group consisting of those compounds corresponding to one of: l (L) B1 、L B2 、L B18 、L B28 、L B38 、L B108 、L B118 、L B122 、L B126 、L B128 、L B132 、L B136 、L B138 、L B142 、L B156 、L B162 、L B204 、L B206 、L B214 、L B216 、L B218 、L B220 、L B231 、L B233 、L B237 、L B264 、L B265 、L B266 、L B267 、L B268 、L B269 And L B270 。
In some embodiments, the compound is selected from the group consisting of having L Cj-I Or L Cj-II Those of the ligands, the corresponding R of the ligands 201 And R is 202 Is defined as one of the following structures: r is R D1 、R D3 、R D4 、R D5 、R D9 、R D10 、R D17 、R D18 、R D20 、R D22 、R D37 、R D40 、R D41 、R D42 、R D43 、R D48 、R D49 、R D50 、R D54 、R D55 、R D58 、R D59 、R D78 、R D79 、R D81 、R D87 、R D88 、R D89 、R D93 、R D116 、R D117 、R D118 、R D119 、R D120 、R D133 、R D134 、R D135 、R D136 、R D143 、R D144 、R D145 、R D146 、R D147 、R D149 、R D151 、R D154 、R D155 、R D161 、R D175 、R D190 、R D193 、R D200 、R D201 、R D206 、R D210 、R D214 、R D215 、R D216 、R D218 、R D219 、R D220 、R D227 、R D237 、R D241 、R D242 、R D245 And R is D246 。
In some embodiments, the compound is selected from the group consisting of having L Cj-I Or L Cj-II Those of the ligands, the corresponding R of the ligands 201 And R is 202 Is defined as one selected from the following structures: r is R D1 、R D3 、R D4 、R D5 、R D9 、R D10 、R D17 、R D22 、R D43 、R D50 、R D78 、R D116 、R D118 、R D133 、R D134 、R D135 、R D136 、R D143 、R D144 、R D145 、R D146 、R D149 、R D151 、R D154 、R D155 、R D190 、R D193 、R D200 、R D201 、R D206 、R D210 、R D214 、R D215 、R D216 、R D218 、R D219 、R D220 、R D227 、R D237 、R D241 、R D242 、R D245 And R is D246 。
In some embodiments, the compound is selected from the group consisting of Cj-I The ligands have the group consisting of those compounds of one of the structures of the following list 13:/>
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in some embodiments, the compound is selected from the group consisting of the compounds of table 14 below:
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in some embodiments, the compound has formula V:
wherein:
M 1 is Pd or Pt;
moieties E and F are each independently a single or multiple ring structure comprising 5-and/or 6-membered carbocycles or heterocycles;
Z 1a And Z 2a Each independently is C or N;
K 1 and K 2 Each independently selected from the group consisting of a direct bond, O and S, wherein K 1 And K 2 At least two of which are direct bonds;
L 1 、L 2 and L 3 Each independently selected from the group consisting of: direct bond, BR, BRR ', NR, PR, P (O) R, O, S, se, C = O, C = S, C =se, c=nr, c=crr', s= O, SO 2 CR, CRR ', siRR ', geRR ', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof, wherein L 1 And L 2 At least one of which is present;
R E and R is F Each independently represents zero substitution, a single substitution, or up to a maximum allowable number of substitutions to its associated ring;
R、R'、R E and R is F Independently hydrogen or a substituent selected from the group consisting of preferred general substituents defined herein; and is also provided with
Where chemically feasible, two adjacent R' s A 、R B 、R C 、R E And R is F May be joined or fused together to form a ring.
In some embodiments of formula V, both moieties E and F are 6 membered aromatic rings.
In some embodiments of formula V, moiety F is a 5-or 6-membered heteroaromatic ring.
In some embodiments of formula V, L 1 Is O or CRR'.
In some embodiments of formula V, Z 2a Is N and Z 1a Is C. In some embodiments of formula V, Z 2a Is C and Z 1a Is N.
In some embodiments of formula V, L 2 Is a direct bond. In some embodiments of formula V, L 2 Is NR.
In some embodiments of formula V, K, K 1 And K 2 Are direct keys. In some embodiments of formula V, K, K 1 And K 2 One of which is O.
In some embodiments of the compound, one R E Is an electron withdrawing group in list EWG 1 as defined herein. In some embodiments of the compound, one R E Is an electron withdrawing group in list EWG 2 as defined herein. In some embodiments of the compound, one R E Is an electron withdrawing group in list EWG 3 as defined herein. In some embodiments of the compound, one R E Is an electron withdrawing group in list EWG 4 as defined herein. In some embodiments of the compound, one R E Is an electron withdrawing group in a list Pi-EWG as defined herein.
In some embodiments of the compound, one R F Is an electron withdrawing group in list EWG 1 as defined herein. In some embodiments of the compound, one R F Is an electron withdrawing group in list EWG 2 as defined herein. In some embodiments of the compound, one R F Is an electron withdrawing group in list EWG 3 as defined herein. In some embodiments of the compound, one R F Is an electron withdrawing group in list EWG 4 as defined herein. In some embodiments of the compound, one R F Is an electron withdrawing group in a list Pi-EWG as defined herein.
In some embodiments of the compounds, the compounds of formula V comprise electron withdrawing groups in the list EWG 1 as defined herein. In some embodiments of the compounds, the compounds of formula V comprise an electron withdrawing group in the list EWG 2 as defined herein. In some embodiments of the compounds, the compounds of formula V comprise an electron withdrawing group in the list EWG 3 as defined herein. In some embodiments of the compounds, the compounds of formula V comprise an electron withdrawing group in the list EWG 4 as defined herein. In some embodiments of the compounds, the compounds of formula V comprise electron withdrawing groups in the list Pi-EWG as defined herein.
In some embodiments, the compound is selected from the group consisting of compounds having the formula Pt (L A' ) A group consisting of compounds of (Ly):
wherein L is A' Having a structure selected from the group consisting of the structures of the following list 15:
wherein L is y Selected from the group consisting of the structures of the following list 16:
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wherein X is Z Each occurrence is independently BR, BRR ', NR, PR, P (O) R, O, S, se, C = O, C = S, C =se, c=nr, c=crr', s= O, SO 2 CR, CRR ', sir ' or GeRR '; and is also provided with
Wherein each R is N Independently hydrogen or a substituent selected from the group consisting of preferred general substituents.
In some embodiments, the compound is selected from the group consisting of compounds having the formula Pt (L A' ) A group consisting of compounds of (Ly):
wherein L is A' Selected from the group consisting of L A'p (R E )(R F ) (W) wherein p is an integer from 1 to 12, each of E and F is independently an integer from 1 to 72, and W is an integer from 1 to 35, wherein L A'1 (R1) (R1) (1) to L A'18 Each of (R72) (35) has a structure defined in the following list 17:
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wherein L is Y Selected from the group consisting of L Yq (R E )(R F ) A group consisting of q is an integer from 1 to 3, and each of E and F is independently an integer from 1 to 72; wherein L is Y1 (R1) (R1) to L Y3 (R72) each has a structure defined in the following list 18:
wherein for each W of 1 to 35, Y 1 And Y 2 Defined in the following table 4:
wherein R is 1 To R 72 With the structure in list 6 disclosed herein.
In some embodiments, the compound is selected from the group consisting of the structures in the following list 19:
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in some embodiments, a first ligand L described herein having formula I A May be at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated. As used herein, deuterated percentages have their ordinary meaning and include percentages of possible hydrogen atoms (e.g., positions of hydrogen or deuterium) replaced by deuterium atoms.
In the presence of a catalyst having the formula M (L A ) p (L B ) q (L C ) r In some embodiments of the heteroleptic compounds of (2), ligand L A Having a first substituent R I Wherein the first substituent R I a-I at ligand L A Is furthest from metal M among all atoms of (a). In addition, ligand L B Having a second substituent R, if present II Wherein the second substituent R II a-II at ligand L B Is furthest from metal M among all atoms of (a). In addition, ligand L C Having a third substituent R, if present III Wherein the third substituent R III The first atom a-III in the ligand L C Is furthest from metal M among all atoms of (a).
In such heteroleptic compounds, the vector V can be defined D1 、V D2 And V D3 It is defined as follows. V (V) D1 Represents the direction from the metal M to the first atom a-I, and the vector V D1 Value D of (2) 1 Represents a metal M and a first substituent R I a-I, the first atom a-I of the group. V (V) D2 Represents the direction from the metal M to the first atom a-II and the vector V D2 Value D of (2) 2 Represents a metal M and a second substituent R II a-II, the first atom a-II. V (V) D3 Representing the transition from metal M to firstThe direction of atoms a-III, and vector V D3 Value D of (2) 3 Represents a metal M and a third substituent R III a-III, and a linear distance between the first atoms a-III.
In such heteroleptic compounds, spheres are defined having a radius R centered at the metal M and the radius R is that which allows the spheres to enclose compounds in which not substituents R I 、R II And R is III A minimum radius of all atoms of a portion of (a); and wherein D 1 、D 2 And D 3 At least one of which is larger than the radius r by at leastIn some embodiments, D 1 、D 2 And D 3 At least 2.9, 3.0, 4.3, 4.4, 5.2, 5.9, 7.3, 8.8, 10.3, 13.1, 17.6 or +.>
In some embodiments of such heteroleptic compounds, the compound has a transition dipole moment axis, and the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 The angle between the transition dipole moment axis and the vector V is determined D1 、V D2 And V D3 At least one angle therebetween is less than 40 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 30 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 20. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 15 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least one angle therebetween is less than 10 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least two angles therebetween being less than 20. In some embodiments, the transition dipole moment axisAnd vector V D1 、V D2 And V D3 At least two angles therebetween being less than 15. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 At least two angles therebetween being less than 10.
In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 All three angles in between are less than 20 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 All three angles in between are less than 15 °. In some embodiments, the transition dipole moment axis is aligned with vector V D1 、V D2 And V D3 All three angles in between are less than 10 °.
In some embodiments of such heteroleptic compounds, the compounds have a Vertical Dipole Ratio (VDR) of 0.33 or less. In some embodiments of such heteroleptic compounds, the compounds have a VDR of 0.30 or less. In some embodiments of such heteroleptic compounds, the compounds have a VDR of 0.25 or less. In some embodiments of such heteroleptic compounds, the compounds have a VDR of 0.20 or less. In some embodiments of such heteroleptic compounds, the compounds have a VDR of 0.15 or less.
The meaning of the term transition dipole moment axis of a compound and the perpendicular dipole ratio of the compound will be readily understood by those of ordinary skill in the art. However, the meaning of these terms can be found in U.S. patent No. 10,672,997, the disclosure of which is incorporated herein by reference in its entirety. In U.S. patent No. 10,672,997, the Horizontal Dipole Ratio (HDR) of a compound is discussed, rather than VDR. However, one skilled in the art will readily understand vdr=1-HDR.
C. OLED and device of the present disclosure
In another aspect, the present disclosure also provides an OLED device comprising a first organic layer containing a compound as disclosed in the above compound section of the present disclosure.
In some embodiments, an OLED comprises: an anode; a cathode; and an organic layer disposed between the anode and the cathode,wherein the organic layer comprises a first ligand L comprising formula I as described herein A Is a compound of (a).
In some embodiments, the organic layer may be an emissive layer and the compound as described herein may be an emissive dopant or a non-emissive dopant.
In some embodiments, the emissive layer includes one or more quantum dots.
In some embodiments, the organic layer may further comprise a host, wherein the host comprises a triphenylene comprising a benzofused thiophene or benzofused furan, wherein any substituent in the host is a non-fused substituent independently selected from the group consisting of: c (C) n H 2n+1 、OC n H 2n+1 、OAr 1 、N(C n H 2n+1 ) 2 、N(Ar 1 )(Ar 2 )、CH=CH-C n H 2n+1 、C≡CC n H 2n+1 、Ar 1 、Ar 1 -Ar 2 、C n H 2n -Ar 1 Or no substituent, wherein n is an integer from 1 to 10; and wherein Ar is 1 And Ar is a group 2 Independently selected from the group consisting of: benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
In some embodiments, the organic layer may further comprise a host, wherein the host comprises at least one chemical group selected from the group consisting of: triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ2-benzo [ d ] benzo [4,5] imidazo [3,2-a ] imidazole, 5, 9-dioxa-13 b-boronaphtho [3,2,1-de ] anthracene, triazine, boron, silicon, azatriphenylene, azacarbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo [ d ] benzo [4,5] imidazo [3,2-a ] imidazole, and aza- (5, 9-dioxa-13 b-boronaphtho [3,2,1-de ] anthracene).
In some embodiments, the subject may be selected from the group consisting of:
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and combinations thereof.
In some embodiments, the subject may be selected from the group consisting of structures in the following subject group:
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wherein:
X 1 to X 24 Each of which is independently C or N;
l' is a direct bond or an organic linking group;
each Y A Independently selected from the group consisting of: absence, bond, O, S, se, CRR ', siRR', geRR ', NR, BR, BRR';
R A '、R B '、R C '、R D '、R E '、R F ' and R G Each of' independently represents a single substitution, up to a maximum substitution, or no substitution;
Each R, R', R A '、R B '、R C '、R D '、R E '、R F ' and R G ' independently is hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silicon-based, germanium-based, seleno, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, boron-based, hydroxyl, and combinations thereof;
R A '、R B '、R C '、R D '、R E '、R F ' and R G Adjacent two of the' are optionally joined or fused to form a ring.
In some embodiments, the organic layer may further comprise a host, wherein the host comprises a metal complex.
In some embodiments, the emissive layer may include two hosts: a first body and a second body. In some embodiments, the first body is a hole transporting body and the second body is an electron transporting body. In some embodiments, the first host and the second host may form an exciplex.
In some embodiments, a compound as described herein may be a sensitizer; wherein the device may further comprise a recipient; and wherein the receptor may be selected from the group consisting of: fluorescent emitters, delayed fluorescent emitters, and combinations thereof.
In yet another aspect, the OLED of the present disclosure may further comprise an emissive region containing a compound as disclosed in the above compound portion of the present disclosure.
In some embodiments, the emission region can comprise a first ligand L comprising formula I as described herein A Is a compound of (a).
In some embodiments, at least one of the anode, cathode, or new layer disposed over the organic emissive layer serves as the enhancement layer. The enhancement layer includes a plasmonic material exhibiting surface plasmon resonance, the plasmonic material non-radiatively coupled to the emitter material and transferring excited state energy from the emitter material to a non-radiative mode of surface plasmon polaritons. The enhancement layer is disposed no further than a threshold distance from the organic emissive layer, wherein the emitter material has a total non-radiative decay rate constant and a total radiative decay rate constant due to the presence of the enhancement layer, and the threshold distance is where the total non-radiative decay rate constant is equal to the total radiative decay rate constant. In some embodiments, the OLED further comprises an outcoupling layer. In some embodiments, the outcoupling layer is disposed on the enhancement layer on an opposite side of the organic emissive layer. In some embodiments, the outcoupling layer is disposed on the opposite side of the emission layer from the enhancement layer, but is still able to outcouple energy from the surface plasmon mode of the enhancement layer. The outcoupling layer scatters energy from the surface plasmon polaritons. In some embodiments, this energy is scattered into free space as photons. In other embodiments, energy is scattered from surface plasmon modes of the device into other modes, such as, but not limited to, an organic waveguide mode, a substrate mode, or another waveguide mode. If the energy is scattered to the non-free space mode of the OLED, other outcoupling schemes may be incorporated to extract the energy into free space. In some embodiments, one or more intervening layers may be disposed between the enhancement layer and the outcoupling layer. Examples of intervening layers may be dielectric materials, including organic, inorganic, perovskite, oxides, and may include stacks and/or mixtures of these materials.
The enhancement layer alters the effective properties of the medium in which the emitter material resides, causing any or all of the following: reduced emissivity, altered emission linearity, altered emission intensity with angle, altered emitter material stability, altered OLED efficiency, and reduced OLED device roll-off efficiency. Placing the enhancement layer on the cathode side, the anode side, or both sides creates an OLED device that takes advantage of any of the effects described above. In addition to the specific functional layers mentioned herein and illustrated in the various OLED examples shown in the figures, an OLED according to the present disclosure may also include any other functional layers common in OLEDs.
The enhancement layer may comprise a plasmonic material, an optically active super-structured material or a hyperbolic super-structured material. As used herein, a plasmonic material is a material in which the real part of the dielectric constant crosses zero in the visible or ultraviolet region of the electromagnetic spectrum. In some embodiments, the plasmonic material comprises at least one metal. In such embodiments, the metal may include at least one of the following: ag. Al, au, ir, pt, ni, cu, W, ta, fe, cr, mg, ga, rh, ti, ru, pd, in, bi, ca, alloys or mixtures of these materials, and stacks of these materials. Generally, a metamaterial is a medium composed of different materials, wherein the overall effect of the medium is different from the sum of its material portions. In particular, we define an optically active super-structured material as a material having both negative permittivity and negative permeability. On the other hand, hyperbolic metamaterials are anisotropic media in which the permittivity or permeability has different signs for different spatial directions. Optically active and hyperbolic metamaterials are very different from many other photonic structures, such as distributed Bragg reflectors (Distributed Bragg Reflector, "DBRs"), because the medium should exhibit uniformity in the direction of propagation over the length scale of the wavelength of light. Using terms that will be understood by those skilled in the art: the dielectric constant of a metamaterial in the propagation direction can be described by an effective dielectric approximation. Plasmonic and super-structured materials provide a method for controlling light propagation that can enhance OLED performance in a variety of ways.
In some embodiments, the enhancement layer is provided as a planar layer. In other embodiments, the enhancement layer has wavelength-sized features that are periodically, quasi-periodically, or randomly arranged, or sub-wavelength-sized features that are periodically, quasi-periodically, or randomly arranged. In some embodiments, the wavelength-sized features and the sub-wavelength-sized features have sharp edges.
In some embodiments, the outcoupling layer has wavelength-sized features that are periodically, quasi-periodically, or randomly arranged, or sub-wavelength-sized features that are periodically, quasi-periodically, or randomly arranged. In some embodiments, the outcoupling layer may be composed of a plurality of nanoparticles, and in other embodiments, the outcoupling layer is composed of a plurality of nanoparticles disposed over the material. In these embodiments, the outcoupling may be adjusted by at least one of the following means: changing the size of the plurality of nanoparticles, changing the shape of the plurality of nanoparticles, changing the material of the plurality of nanoparticles, adjusting the thickness of the material, changing the refractive index of the material or an additional layer disposed on the plurality of nanoparticles, changing the thickness of the reinforcing layer, and/or changing the material of the reinforcing layer. The plurality of nanoparticles of the device may be formed from at least one of: a metal, a dielectric material, a semiconductor material, a metal alloy, a mixture of dielectric materials, a stack or layering of one or more materials and/or a core of one type of material and a shell coated with another type of material. In some embodiments, the outcoupling layer is composed of at least metal nanoparticles, wherein the metal is selected from the group consisting of: ag. Al, au, ir, pt, ni, cu, W, ta, fe, cr, mg, ga, rh, ti, ru, pd, in, bi, ca, alloys or mixtures of these materials, and stacks of these materials. The plurality of nanoparticles may have additional layers disposed over them. In some embodiments, the polarization of the emission may be adjusted using an outcoupling layer. Changing the size and periodicity of the outcoupling layer may select the type of polarization that preferentially outcouples to air. In some embodiments, the outcoupling layer also serves as an electrode of the device.
In yet another aspect, the present disclosure also provides a consumer product comprising an Organic Light Emitting Device (OLED) having an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a compound as disclosed in the above compound section of the disclosure.
In some embodiments, the consumer product comprises an OLED having: an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a first ligand L comprising formula I as described herein A Is a compound of (a).
In some embodiments, the consumer product may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
In general, an OLED includes at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer. The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and a hole are localized on the same molecule, an "exciton" is formed, which is a localized electron-hole pair having an excited energy state. Light is emitted when the exciton relaxes through a light emission mechanism. In some cases, excitons may be localized on an excimer or exciplex. Non-radiative mechanisms (such as thermal relaxation) may also occur, but are generally considered undesirable.
Several OLED materials and configurations are described in U.S. patent nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
Initial OLEDs used emissive molecules that emitted light ("fluorescence") from a singlet state, as disclosed, for example, in U.S. patent No. 4,769,292, which is incorporated by reference in its entirety. Fluorescence emission typically occurs in time frames less than 10 nanoseconds.
Recently, OLEDs have been demonstrated that have emissive materials that emit light from a triplet state ("phosphorescence"). Baldo et al, "efficient phosphorescent emission from organic electroluminescent devices (Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices)", nature, vol.395, 151-154,1998 ("Baldo-I"); and Bardo et al, "Very efficient green organic light emitting device based on electrophosphorescence (Very high-efficiency green organic light-emitting devices based on electrophosphorescence)", applied physical fast report (appl. Phys. Lett.), vol.75, stages 3,4-6 (1999) ("Bardo-II"), incorporated by reference in its entirety. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704, columns 5-6, which is incorporated by reference.
Fig. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. The device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a blocking layer 170. Cathode 160 is a composite cathode having a first conductive layer 162 and a second conductive layer 164. The device 100 may be fabricated by depositing the layers in sequence. The nature and function of these various layers and example materials are described in more detail in U.S. Pat. No. 7,279,704 at columns 6-10, which is incorporated by reference.
Further examples of each of these layers are available. 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 entiretyIncorporated in the manner used. An example of a p-doped hole transport layer is doped with F in a 50:1 molar ratio 4 m-MTDATA of TCNQ, as disclosed in U.S. patent application publication No. 2003/0239980, which is incorporated by reference in its entirety. Examples of luminescent and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of cathodes are disclosed in U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, that include composite cathodes having a thin layer of metal (e.g., mg: ag) containing an overlying transparent, electrically conductive, sputter-deposited ITO layer. The theory and use of barrier layers is 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 implanted layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
Fig. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. The device 200 may be fabricated by depositing the layers in sequence. Because the most common OLED configuration has a cathode disposed above an anode, and the device 200 has a cathode 215 disposed below an anode 230, the device 200 may be referred to as an "inverted" OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. Fig. 2 provides one example of how some layers may be omitted from the structure of the apparatus 100.
The simple layered structure illustrated in fig. 1 and 2 is provided by way of non-limiting example, and it should be understood that embodiments of the present disclosure may be used in conjunction with a variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be obtained by combining the various layers described in different ways, or the layers may be omitted entirely based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe the various layers as comprising a single material, it should be understood that combinations of materials may be used, such as mixtures of host and dopant, or more generally, mixtures. Further, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to fig. 1 and 2.
Structures and materials not specifically described, such as OLEDs (PLEDs) comprising polymeric materials, such as disclosed in frank (Friend) et al, U.S. patent No. 5,247,190, which is incorporated by reference in its entirety, may also be used. By way of another example, an OLED with a single organic layer may be used. The OLEDs can be stacked, for example, as described in U.S. patent No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in fig. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Furster et al, and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Boolean et al, which are incorporated by reference in their entirety.
Any of the layers of the various embodiments may be deposited by any suitable method unless otherwise specified. Preferred methods for the organic layer include thermal evaporation, ink jet (as described in U.S. Pat. nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entirety), organic vapor deposition (OVPD) (as described in U.S. Pat. No. 6,337,102, which is incorporated by reference in its entirety), and deposition by organic vapor jet printing (OVJP, also known as Organic Vapor Jet Deposition (OVJD)), as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin-coating and other solution-based processes. The solution-based process is preferably carried out under nitrogen or an inert atmosphere. For other layers, the preferred method includes thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding (as described in U.S. patent nos. 6,294,398 and 6,468,819, incorporated by reference in their entirety), and patterning associated with some of the deposition methods such as inkjet and Organic Vapor Jet Printing (OVJP). Other methods may also be used. The material to be deposited may be modified to suit the particular deposition method. For example, substituents such as alkyl and aryl groups that are branched or unbranched and preferably contain at least 3 carbons can be used in small molecules to enhance their ability to withstand solution processing. Substituents having 20 carbons or more may be used, and 3 to 20 carbons are a preferred range. A material with an asymmetric structure may have better solution processibility than a material with a symmetric structure because an asymmetric material may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.
Devices fabricated according to embodiments of the present disclosure may further optionally include a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from harmful substances exposed to the environment including moisture, vapors and/or gases, etc. The barrier layer may be deposited on the substrate, electrode, under or beside the substrate, electrode, or on any other portion of the device, including the edge. The barrier layer may comprise a single layer or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include a composition having a single phase and a composition having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate inorganic compounds or organic compounds or both. Preferred barrier layers comprise a mixture of polymeric and non-polymeric materials, as described in U.S. patent No. 7,968,146, PCT patent application No. PCT/US2007/023098, and PCT/US2009/042829, which are incorporated herein by reference in their entirety. To be considered as a "mixture", the aforementioned polymeric and non-polymeric materials that make up the barrier layer should be deposited under the same reaction conditions and/or simultaneously. The weight ratio of polymeric material to non-polymeric material may be in the range of 95:5 to 5:95. The polymeric material and the non-polymeric material may be produced from the same precursor material. In one example, the mixture of polymeric and non-polymeric materials consists essentially of polymeric silicon and inorganic silicon.
Devices manufactured in accordance with embodiments of the present disclosure may be incorporated into a wide variety of electronic component modules (or units), which may be incorporated into a wide variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices (e.g., discrete light source devices or lighting panels), etc., that may be utilized by end user product manufacturers. The electronics assembly module may optionally include drive electronics and/or a power source. Devices manufactured in accordance with embodiments of the present disclosure may be incorporated into a wide variety of consumer products having one or more electronic component modules (or units) incorporated therein. Disclosed is a consumer product comprising an OLED comprising a compound of the present disclosure in an organic layer in the OLED. The consumer product should include any kind of product that contains one or more light sources and/or one or more of some type of visual display. Some examples of such consumer products include flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, cellular telephones, tablet computers, tablet phones, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays (displays with a diagonal of less than 2 inches), 3-D displays, virtual or augmented reality displays, vehicles, video walls including a plurality of tiled displays, theatre or gym screens, phototherapy devices, and signs. Various control mechanisms may be used to control devices manufactured in accordance with the present disclosure, including passive matrices and active matrices. Many of the devices are intended to be used in a temperature range that is comfortable for humans, such as 18 ℃ to 30 ℃, and more preferably at room temperature (20-25 ℃), but can be used outside this temperature range (e.g., -40 ℃ to +80 ℃).
Further details regarding OLEDs and the definitions described above can be found in U.S. patent No. 7,279,704, which is incorporated herein by reference in its entirety.
The materials and structures described herein may be applied in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices such as organic transistors may employ the materials and structures.
In some embodiments, the OLED has one or more features selected from the group consisting of: flexible, crimpable, collapsible, stretchable and bendable. In some embodiments, the OLED is transparent or translucent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.
In some embodiments, the OLED further comprises a layer comprising a delayed fluorescent emitter. In some embodiments, the OLED includes an RGB pixel arrangement or a white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a handheld device, or a wearable device. In some embodiments, the OLED is a display panel having a diagonal of less than 10 inches or an area of less than 50 square inches. In some embodiments, the OLED is a display panel having a diagonal of at least 10 inches or an area of at least 50 square inches. In some embodiments, the OLED is an illumination panel.
In some embodiments, the compound may be an emissive dopant. In some embodiments, the compounds may produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence (i.e., TADF, also known as delayed fluorescence of type E, see, e.g., U.S. application No. 15/700,352, which is incorporated herein by reference in its entirety), triplet-triplet annihilation, or combinations of these processes. In some embodiments, the emissive dopant may be a racemic mixture, or may be enriched in one enantiomer. In some embodiments, the compounds may be homoleptic (identical for each ligand). In some embodiments, the compounds may be compounded (at least one ligand is different from the others). In some embodiments, when there is more than one ligand coordinated to the metal, the ligands may all be the same. In some other embodiments, at least one ligand is different from the other ligands. In some embodiments, each ligand may be different from each other. This is also true in embodiments where the ligand coordinated to the metal may be linked to other ligands coordinated to the metal to form a tridentate, tetradentate, pentadentate or hexadentate ligand. Thus, where the coordinating ligands are linked together, in some embodiments all of the ligands may be the same, and in some other embodiments at least one of the linking ligands may be different from the other ligand(s).
In some embodiments, the compounds may be used as a phosphor-photosensitizing agent in an OLED, where one or more layers in the OLED contain receptors in the form of one or more fluorescent and/or delayed fluorescent emitters. In some embodiments, the compound may be used as a component of an exciplex to be used as a sensitizer. As a phosphorus photosensitizer, the compound must be able to transfer energy to the acceptor and the acceptor will emit energy or further transfer energy to the final emitter. The receptor concentration may be in the range of 0.001% to 100%. The acceptor may be in the same layer as the phosphorus photosensitizer or in one or more different layers. In some embodiments, the receptor is a TADF emitter. In some embodiments, the acceptor is a fluorescent emitter. In some embodiments, the emission may be produced by any or all of the sensitizer, acceptor, and final emitter.
According to another aspect, a formulation comprising a compound described herein is also disclosed.
The OLEDs disclosed herein can be incorporated into one or more of consumer products, electronics assembly modules, and lighting panels. The organic layer may be an emissive layer, and the compound may be an emissive dopant in some embodiments, and the compound may be a non-emissive dopant in other embodiments.
In yet another aspect of the invention, a formulation comprising the novel compounds disclosed herein is described. The formulation may comprise one or more components disclosed herein selected from the group consisting of: a solvent, a host, a hole injection material, a hole transport material, an electron blocking material, a hole blocking material, and an electron transport material.
The present disclosure encompasses any chemical structure comprising the novel compounds of the present disclosure or monovalent or multivalent variants thereof. In other words, the compounds of the invention or monovalent or multivalent variants thereof may be part of a larger chemical structure. Such chemical structures may be selected from the group consisting of: monomers, polymers, macromolecules and supramolecules (also known as supramolecules). As used herein, "monovalent variant of a compound" refers to the same moiety as the compound but with one hydrogen removed and replaced with a bond to the rest of the chemical structure. As used herein, "multivalent variant of a compound" refers to a moiety that is identical to the compound but where more than one hydrogen has been removed and replaced with one or more bonds to the rest of the chemical structure. In the case of supramolecules, the compounds of the present invention may also be incorporated into supramolecular complexes without covalent bonds.
D. Combinations of compounds of the present disclosure with other materials
Materials described herein as suitable for use in particular layers in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the emissive dopants disclosed herein can be used in combination with a wide variety of hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. The materials described or mentioned below are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one of ordinary skill in the art may readily review the literature to identify other materials that may be used in combination.
a) Conductive dopants:
the charge transport layer may be doped with a conductive dopant to substantially change its charge carrier density, which in turn will change its conductivity. Conductivity is increased by the generation of charge carriers in the host material and, depending on the type of dopant, a change in Fermi level (Fermi level) of the semiconductor can also be achieved. The hole transport layer may be doped with a p-type conductivity dopant, and an n-type conductivity dopant is used in the electron transport layer.
Non-limiting examples of conductive dopants that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references disclosing those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804, US20150123047 and US2012146012.
b)HIL/HTL:
The hole injection/transport material used in the present disclosure is not particularly limited, and any compound may be used as long as the compound is generally used as a hole injection/transport material. Examples of materials include (but are not limited to): phthalocyanines or porphyrin derivatives; aromatic amine derivatives; indolocarbazole derivatives; a fluorocarbon-containing polymer; a polymer having a conductive dopant; conductive polymers such as PEDOT/PSS; self-assembled monomers derived from compounds such as phosphonic acids and silane derivatives; metal oxide derivatives, e.g. MoO x The method comprises the steps of carrying out a first treatment on the surface of the p-type semiconducting organic compounds such as 1,4,5,8,9, 12-hexaazatriphenylene hexacarbonitrile; a metal complex; a crosslinkable compound.
Examples of aromatic amine derivatives for the HIL or HTL include, but are not limited to, the following general structures:
Ar 1 to Ar 9 Is selected from: a group consisting of, for example, the following aromatic hydrocarbon cyclic compounds: benzene, biphenyl, triphenylene, naphthalene, anthracene, benzene, phenanthrene, fluorene, pyrene, and the like,Perylene and azulene; a group consisting of aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranpyridine, furandipyridine, benzothiophenopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and a group consisting of 2 to 10 cyclic structural units which are the same type or different types of groups selected from an aromatic hydrocarbon ring group and an aromatic heterocyclic group and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group. Each Ar may be unsubstituted or may be substituted with a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In one aspect, ar 1 To Ar 9 Independently selected from the group consisting of:
wherein k is an integer of 1 to 20; x is X 101 To X 108 Is C (including CH) or N; z is Z 101 Is NAr 1 O or S; ar (Ar) 1 Having the same groups as defined above.
Examples of metal complexes used in the HIL or HTL include, but are not limited to, the following general formula:
wherein Met is a metal that may have an atomic weight greater than 40; (Y) 101 -Y 102 ) Is a bidentate ligand, Y 101 And Y 102 Independently selected from C, N, O, P and S; l (L) 101 Is an auxiliary ligand; k' is an integer value of 1 to the maximum number of ligands that can be attached to the metal; and k' +k "is the maximum number of ligands that can be attached to the metal.
In one aspect, (Y) 101 -Y 102 ) Is a 2-phenylpyridine derivative. In another aspect, (Y) 101 -Y 102 ) Is a carbene ligand. In another aspect, met is selected from Ir, pt, os, and Zn. In another aspect, the metal complex has a chemical structure as compared to an Fc + The minimum oxidation potential in solution of less than about 0.6V for Fc coupling.
Non-limiting examples of HIL and HTL materials that can be used in an OLED in combination with the materials disclosed herein are exemplified with references disclosing those materials as follows: CN, DE, EP EP, JP07-, JP EP, EP JP07-, JP US, US US, WO US, US WO, WO.
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c)EBL:
An Electron Blocking Layer (EBL) may be used to reduce the number of electrons and/or excitons that leave the emissive layer. The presence of such a barrier layer in a device may result in substantially higher efficiency and/or longer lifetime than a similar device lacking such a barrier layer. Furthermore, a blocking layer may be used to limit the emission to a desired area of the OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to vacuum level) and/or higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in the EBL contains the same molecule or the same functional group as used in one of the hosts described below.
d) A main body:
the light-emitting layer of the organic EL device of the present disclosure preferably contains at least a metal complex as a light-emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complex or organic compound may be used as long as the triplet energy of the host is greater than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria are met.
Examples of metal complexes used as hosts preferably have the general formula:
wherein Met is a metal; (Y) 103 -Y 104 ) Is a bidentate ligand, Y 103 And Y 104 Independently selected from C, N, O, P and S; l (L) 101 Is another ligand; k' is an integer value of 1 to the maximum number of ligands that can be attached to the metal; and k' +k "is the maximum number of ligands that can be attached to the metal.
In one aspect, the metal complex is:
wherein (O-N) is a bidentate ligand having a metal coordinated to the O and N atoms.
In another aspect, met is selected from Ir and Pt. In another aspect, (Y) 103 -Y 104 ) Is a carbene ligand.
In one aspect, the host compound contains at least one selected from the group consisting of: a group consisting of, for example, the following aromatic hydrocarbon cyclic compounds: benzene, biphenyl, triphenylene, tetramethylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,Perylene and azulene; a group consisting of aromatic heterocyclic compounds such as: dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuranpyridine, furandipyridine, benzothiophenopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and a group consisting of 2 to 10 cyclic structural units which are the same type or different types of groups selected from an aromatic hydrocarbon ring group and an aromatic heterocyclic group and are bonded to each other directly or via at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit, and an aliphatic ring group. Each option in each group may be unsubstituted or may be substituted with a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, ammonia A group, silicon-based, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In one aspect, the host compound contains in the molecule at least one of the following groups:
wherein R is 101 Selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silicon-based, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has a similar definition as Ar mentioned above. k is an integer from 0 to 20 or from 1 to 20. X is X 101 To X 108 Independently selected from C (including CH) or N. Z is Z 101 And Z 102 Independently selected from NR 101 O or S.
Non-limiting examples of host materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references disclosing those materials: US, WO WO, WO-based US, WO WO, US, US and US,
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e) Other emitters:
one or more other emitter dopants may be used in combination with the compounds of the present invention. Examples of other emitter dopants are not particularly limited, and any compound may be used as long as the compound is generally used as an emitter material. Examples of suitable emitter materials include, but are not limited to, compounds that can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence (i.e., TADF, also known as E-delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.
Non-limiting examples of emitter materials that can be used in OLEDs in combination with the materials disclosed herein are exemplified below along with references disclosing those materials: CN, EB, EP1239526, EP, JP, KR TW, US20010019782, US TW, US20010019782, US US, US US, WO US, US US, WO.
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f)HBL:
A Hole Blocking Layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a barrier layer in a device may result in substantially higher efficiency and/or longer lifetime than a similar device lacking the barrier layer. Furthermore, a blocking layer may be used to limit the emission to a desired area of the OLED. In some embodiments, the HBL material has a lower HOMO (farther from the vacuum level) and/or higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (farther from the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the HBL interface.
In one aspect, the compound used in the HBL contains the same molecules or the same functional groups as used in the host described above.
In another aspect, the compound used in the HBL contains in the molecule at least one of the following groups:
wherein k is an integer from 1 to 20; l (L) 101 Is another ligand, and k' is an integer from 1 to 3.
g)ETL:
An Electron Transport Layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complex or organic compound may be used as long as it is generally used to transport electrons.
In one aspect, the compounds used in ETL contain in the molecule at least one of the following groups:
wherein R is 101 Selected from the group consisting of: hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silicon-based, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof, when aryl or heteroaryl, having similar definitions as for Ar described above. Ar (Ar) 1 To Ar 3 Has a similar definition to Ar mentioned above. k is an integer of 1 to 20. X is X 101 To X 108 Selected from C (including CH) or N.
In another aspect, the metal complex used in ETL contains (but is not limited to) the following formula:
wherein (O-N) or (N-N) is a bidentate ligand having a metal coordinated to atom O, N or N, N; l (L) 101 Is another ligand; k' is an integer value from 1 to the maximum number of ligands that can be attached to the metal.
Non-limiting examples of ETL materials that can be used in an OLED in combination with the materials disclosed herein are exemplified below along with references disclosing those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, US6656612, US8415031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,
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h) Charge Generation Layer (CGL)
In tandem or stacked OLEDs, CGL plays a fundamental role in performance, consisting of n-doped and p-doped layers for injecting electrons and holes, respectively. Electrons and holes are supplied by the CGL and the electrode. Electrons and holes consumed in the CGL are refilled with electrons and holes injected from the cathode and anode, respectively; subsequently, the bipolar current gradually reaches a steady state. Typical CGL materials include n and p conductivity dopants used in the transport layer.
In any of the above mentioned compounds used in each layer of the OLED device, the hydrogen atoms may be partially or fully deuterated. The minimum amount of deuterated hydrogen in the compound is selected from the group consisting of: 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99% and 100%. Thus, any of the specifically listed substituents, such as (but not limited to) methyl, phenyl, pyridyl, and the like, can be in their non-deuterated, partially deuterated, and fully deuterated forms. Similarly, substituent classes (e.g., without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc.) can also be in their non-deuterated, partially deuterated, and fully deuterated forms.
It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. The invention as claimed may thus include variations of the specific examples and preferred embodiments described herein, as will be apparent to those skilled in the art. It should be understood that the various theories as to why the present invention works are not intended to be limiting.
E. Experimental data
To a 500mL round bottom flask equipped with a septum and a stirring bar was added 4-bromothiophene-2-carboxylic acid (21.5 g,104 mmol), HBTU (41.4 g,109 mmol) and 100mL DMF. It was cooled in an ice bath over 20 minutes. A solution of 2, 2-dimethoxyethane-1-amine (12.01 g,114 mmol) and DIPEA (20.74 g,160.46 mmol) in DMF (20 mL) was then added dropwise via an addition funnel at 0deg.C. The reaction was allowed to warm to room temperature and stirred for 3 hours. LCMS analysis showed complete conversion. Citric acid solution (20.55 g in 350mL of water) was slowly added and stirred for 2 hours. The two phases were separated and the aqueous phase was additionally extracted with EtOAc (2X 90 mL). The combined organics were washed with brine and dried over anhydrous MgSO 4 Briefly dried, filtered and concentrated under vacuum at up to 55 ℃ to give a yellow oil. This oil underwent SiO 2 Column chromatography (eluent: heptane to EtOAc/heptane (30%) afforded the product as a white solid (21 g, 68% yield).
A250 mL round bottom flask equipped with a septum and a stir bar was charged with 5-bromo-N- (2, 2-dimethoxyethyl) thiophene-2-carboxamide (20.14 g,68.5 mmol). Trifluoromethanesulfonic acid (60.8 ml,685 mmol) was added and the reaction mixture was heated at 98 ℃ (oil bath temperature) for 7 hours. LCMS analysis showed complete conversion. The reaction was cooled to room temperature and quenched with saturated sodium bicarbonate solution (100 mL). After sedimentation of the flue gas, saturated sodium bicarbonate solution (300 mL) was added. Followed by filtration and rinsing with water (100 mL). The brown solid was stirred in MeOH (120 mL) for 30 min. Subsequent filtration and washing with MeOH (50 mL) and drying in air afforded the product as a brown solid (9.2 g, 58% yield).
Into a 250mL round bottom flask equipped with a septum and a stir bar was placed 3-bromothieno [2,3-c ] pyridin-7-ol (10.00 g,43.46 mmol). Phosphorus tribromide (100.0 g,34.84ml,369.4 mmol) was added and the reaction mixture was heated at 160 ℃ (oil bath temperature) for 16 hours. LCMS analysis showed complete conversion. The reaction was cooled to room temperature and quenched with ice water. After sedimentation of the flue gas, saturated sodium bicarbonate solution (300 mL) was added. The aqueous solution was extracted with EtOAc (3×100 mL) to give the product as a yellow solid (6 g, 47% yield).
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A500 mL dry round bottom flask equipped with a septum and a stir bar was charged with 3, 7-dibromothieno [2,3-c]Pyridine (6.200 g,21.16 mmol). 1, 4-dioxane (120.000 mL) and water (40.00 mL) were added. Subsequently, 2- (4- (tert-butyl) naphthalen-2-yl) -4, 5-tetramethyl-1, 3, 2-dioxaborolan (6.040 g,19.47 mmol) was added and the mixture was bubbled with nitrogen for 30 minutes. Potassium carbonate (5.849 g,42.32 mmol) and tetrakis (triphenylphosphine) palladium (0) (611.4 mg, 529.0. Mu. Mol) were then added and the mixture was bubbled with nitrogen for an additional 10 minutes. A nitrogen balloon was attached. The reaction mixture was vigorously stirred at 80 ℃ (preheated oil bath temperature) for 16 hours. Water and its preparation methodThe phase was additionally extracted with EtOAc (2X 60 mL). The combined organics were washed with brine and dried over anhydrous MgSO 4 Briefly dried, filtered and concentrated under vacuum at up to 40 ℃ to give a yellow solid. The solid undergoes SiO 2 Column chromatography (eluent: heptane to DCM/heptane (40%) afforded the product as a white solid (7 g, 83% yield).
A500 mL dry round bottom flask equipped with a septum and a stir bar was charged with 3-bromo-7- (4- (tert-butyl) naphthalen-2-yl) thieno [2,3-c]Pyridine (6.890 g,17.38 mmol). THF (120.0 mL) was added via syringe and stirred for 10 minutes. The reaction flask was cooled to-78 ℃ (internal temperature) and held for 30 minutes. Lithium diisopropylamide solution (2.235 g,10.43ml,2.000 moles, 20.86 mmol) was added dropwise over 20 minutes using a dropping funnel. The reaction mixture was then stirred at-78 ℃ for 2 hours. Iodine-containing (6.618 g,4.045mL,1.5Eq,26.08 mmol) THF (50 mL) was added dropwise over 60 min using a dropping funnel and stirred at-78℃for 1.5 h. The cold bath was removed and allowed to slowly warm to room temperature. After 1 hour, 200mL of saturated sodium thiosulfate solution was added and stirred for 16 hours. The two phases were separated and the aqueous phase was additionally extracted with EtOAc (2×80 mL). The combined organics were dried over anhydrous MgSO 4 Briefly dried, filtered and concentrated under vacuum at up to 40 ℃ to give a yellow solid. The solid undergoes SiO 2 Column chromatography (eluent: heptane to DCM/heptane (60%)) afforded a white solid (4.11 g, 46% yield).
A500 mL dry round bottom flask equipped with a septum and a stir bar was charged with 3-bromo-7- (4- (tert-butyl) naphthalen-2-yl) -2-iodothieno [2,3-c]Pyridine (4.110 g, 7.87mmol). Triethylamine (120.000 mL) was added. The mixture was bubbled with nitrogen for 20 minutes. Bis- (triphenylphosphine) -palladium chloride (552.4 mg,787.0 μm) was addedol) and copper (I) iodide (74.94 mg, 393.5. Mu. Mol) and bubbled with nitrogen for 10 minutes. T-butylacetylene (840.5 mg,10.23 mmol) was added via syringe. A nitrogen balloon was attached. The reaction mixture was vigorously stirred at 50℃for 16 hours. The two phases were separated and the aqueous phase was additionally extracted with EtOAc (2X 60 mL). The combined organics were washed with brine and dried over anhydrous Na 2 SO 4 Dried, filtered and concentrated under vacuum at up to 40 ℃ to give a brown solid. The solid undergoes SiO 2 Column chromatography (eluent: heptane to DCM/heptane (60%)) afforded a yellow solid (3.8 g, 87% yield).
A500 mL dry round bottom flask equipped with a septum and a stir bar was charged with 3-bromo-7- (4- (tert-butyl) naphthalen-2-yl) -2- (3, 3-dimethylbut-1-yn-1-yl) thieno [2,3-c ]Pyridine (3.800 g,7.975 mmol). 1, 4-dioxane (150.000 mL) (forming a clear yellow solution) and water (50.00 mL) were added. The mixture was bubbled with nitrogen for 20 minutes. Potassium hydroxide (1.579 g,85% Wt,23.93 mmol), tBuXPhos (338.7 mg, 797.5. Mu. Mol) and tris (dibenzylideneacetone) dipalladium (365.2 mg, 398.8. Mu. Mol) [ Pd2 (dba) 3 were added]And bubbling with nitrogen for 10 minutes. The reaction mixture was vigorously stirred at 97deg.C (pre-heated oil bath temperature) for 3.5 hours. The reaction was cooled to room temperature, then water (80 mL) and EtOAc (80 mL) were added to the reaction mixture. The two phases were separated and the aqueous phase was additionally extracted with EtOAc (2X 60 mL). The combined organics were washed with brine and dried over anhydrous MgSO 4 Dried, filtered and concentrated under vacuum at up to 50 ℃ to give a brown solid. The solid undergoes SiO 2 Column chromatography (eluent: heptane to DCM/heptane (60%)) afforded the product as a yellow solid (2.1 g, 75% yield).
To 2-ethoxyethanol (30 mL) and water (10 mL) was added 2- (tert-butyl) -5- (4- (tert-butyl)Radical) naphthalen-2-yl) furo [2',3':4,5]Thieno [2,3-c]Pyridine (1.0 g,2.44 mmol) and IrCl 3 (0.43 g,1.22 mmol). The mixture was heated to reflux and left overnight. The red solid was collected by filtration and used directly in the next step.
To THF (10 mL) was added Ir dimer from previous reaction (0.52 g,0.25 mmol) and potassium 3, 7-diethyl-6-oxononan-4-ate (0.18, 0.74 mmol). The mixture was heated at 40 ℃ overnight. The residue was purified by silica gel using a heptane/DCM mixture to give the product.
Photoluminescence (PL) spectra of the compounds of the invention were measured in PMMA films and are shown in fig. 3. The compound exhibited a red emission with a peak wavelength at 606 nm. The inventive examples exhibited a smaller shoulder and a FWHM of 33 nm. When the compounds of the present invention are used as emissive dopants in organic electroluminescent devices, it would be desirable to emit saturated red light to improve device performance, such as high electroluminescent efficiency and lower power consumption.
Claims (15)
1. A compound comprising a first ligand L of formula I A ,
Wherein:
X 1 、X 2 、X 3 and X 4 Each of which is independently C or N;
part B is a fused ring system comprising two or more rings, wherein each of the two or more rings is independently a 5-or 6-membered carbocyclic or heterocyclic ring;
X 1 to X 4 Is C and is fused with a structure selected from the group consisting of: II (II)Formula III->And formula IV->
Y 1 And Y 2 Independently selected from the group consisting of: o, S, se, CRR ', siRR', geRR ', NR, BR and BRR';
Z、Z 1 And Z 2 Each of which is independently C or N;
k is selected from the group consisting of: direct bond, O, S, N (R) α )、P(R α )、B(R α )、C(R α )、C(R α )(R β ) And Si (R) α )(R β );
R A Represents a di-substitution to the maximum allowable substitution;
R B and R is C Independently represents mono-substitution to maximum allowable substitution, or no substitution;
each R, R', R α 、R β 、R A 、R B And R is C Independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silicon, germanium, boron, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, hydroxy, seleno, and combinations thereof;
L A coordinated to a metal M having an atomic mass of at least 40;
m is capable of coordinating with other ligands;
L A can be conjugated with other ligands to form tridentate, tetradentate, pentadentate or hexadentate ligands; and is also provided with
Any two substituents can be joined or fused to form a ring, provided that if Z 1 And Z 2 Each is C, thatY (what is) 1 And Y 2 Not both are S.
2. The compound of claim 1, wherein part B is selected from the group consisting of: naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, benzoxazole, benzothiophene, benzothiazole, benzoselenophene, indene, indole, benzimidazole, carbazole, dibenzofuran, dibenzothiophene, quinoxaline, phthalazine, phenanthrene, phenanthridine, and fluorene;
Wherein Y is 1 Is O, S, NR, siRR' or Se; and/or
Wherein Y is 2 O, S, NR, CRR ', siRR' or Se; and/or
Wherein at least one R C Selected from the group consisting of: alkyl, silicon-based, partially or fully fluorinated variants thereof, partially or fully deuterated variants thereof, and combinations thereof; and/or
Wherein Z is 1 And Z 2 Is C; or (b)
Wherein Z is 1 Is C and Z 2 Is N; or (b)
Wherein Z is 1 Is N, and Z 2 Is C; and/or
Wherein X is 1 To X 4 Each of (2) is C; or (b)
Wherein X is 1 To X 4 At least one of which is N.
3. The compound according to claim 1, wherein X 1 And X 2 Is C and is bonded by a dashed line to a structure selected from the group consisting of formula II, formula III and formula IV.
4. The compound according to claim 1, wherein X 2 And X 3 Is C and is bonded by a dashed line to a structure selected from the group consisting of formula II, formula III and formula IV.
5. The compound of claim 1, wherein the ligand L A Selected from the group consisting of:
6. the compound of claim 1, wherein the ligand L A Selected from the group consisting of:
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wherein:
Y 3 selected from the group consisting of: o, S, se, CRR ', siRR', geRR ', NR, BR and BRR';
Z 3 and Z 4 Each of which is independently C or N;
R BB Represents mono-substitution to maximum allowable substitution, or no substitution; and is also provided with
Each R is BB Independently hydrogen or a substituent selected from the group consisting of: deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, amino, silicon, germanium, boron, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, seleno, and combinations thereof.
7. The compound of claim 1, wherein the ligand L A Selected from L Ai-w-m Wherein i is an integer from 1 to 4320, w is an integer from 1 to 35, and m is an integer from 1 to 24;
wherein L is Ai-w-1 To L Ai-w-24 Is defined as follows:
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wherein for each w in 1 to 35Y 1 And Y 2 The definition is as follows:
wherein for L A1 To L A4320 Each L of (a) Ai ,R E 、R F And G is defined as follows:
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wherein R is 1 To R 72 The structure is as follows:
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and is also provided with
Wherein G is 1 To G 20 The structure is as follows:
8. the compound of claim 1, wherein the compound has the formula M (L A ) p (L B ) q (L C ) r Wherein L is B And L C Each is a bidentate ligand; and wherein p is 1, 2 or 3; q is 0, 1 or 2; r is 0, 1 or 2; and is also provided with
p+q+r is the oxidation state of the metal M.
9. The compound of claim 8, wherein the compound has a formula selected from the group consisting of: ir (L) A ) 3 、Ir(L A )(L B ) 2 、Ir(L A ) 2 (L B )、Ir(L A ) 2 (L C ) And Ir (L) A )(L B )(L C ) The method comprises the steps of carrying out a first treatment on the surface of the And wherein L is A 、L B And L C Are different from each other; or wherein the compound has the formula Pt (L A )(L B ) The method comprises the steps of carrying out a first treatment on the surface of the And wherein L is A And L is equal to B May be the same or different.
10. The compound of claim 8, wherein L B And L C Each independently selected from the group consisting of:
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wherein:
t is selected from the group consisting of: B. al, ga and In;
Y 1 to Y 13 Independently selected from the group consisting of carbon and nitrogen;
y' is selected from the group consisting of: BR (BR) e 、BR e R f 、NR e 、PR e 、P(O)R e 、O、S、Se、C=O、
C=S、C=Se、C=NR e 、C=CR e R f 、S=O、SO 2 、CR e R f 、SiR e R f And GeR e R f ;
R e And R is f Can be fused or joined to form a ring;
each R is a 、R b 、R c And R is d Independently represents zero substitution, a single substitution, or up to a maximum allowable number of substitutions to its associated ring;
R a1 、R b1 、R c1 、R d1 、R a 、R b 、R c 、R d 、R e and R is f Independently hydrogen or a substituent selected from the group consisting of: deuterium, halo, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silicon, germanium, boron, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, seleno, sulfinyl, sulfonyl, phosphino, and combinations thereof; general substituents as defined herein; and is also provided with
Any two adjacent R a 、R b 、R c 、R d 、R e And R is f Can be fused or joined to form a ring or to form a multidentate ligand.
11. The compound of claim 8, wherein L A Can be selected from L Ai-w-m Wherein i is an integer from 1 to 4320; w is an integer of 1 to 35, m is an integer of 1 to 52; and L is B Can be selected from L Bk Wherein k is an integer from 1 to 474; and L is C Can be selected from L Cj-I Or L Cj-II Wherein j Is an integer from 1 to 1416;
wherein:
when the compound has the formula Ir (L Ai-w-m ) 3 When the compound is selected from Ir (L) A1-1-1 ) 3 To Ir (L) A4320-35-52 ) 3 A group of groups;
when the compound has the formula Ir (L Ai-w-m )(L Bk ) 2 When the compound is selected from Ir (L) A1-1-1 )(L B1 ) 2 To Ir (L) A4320-35-52 )(L B474 ) 2 A group of groups;
when the compound has the formula Ir (L Ai-w-m ) 2 (L Bk ) When the compound is selected from Ir (L) A1-1-1 ) 2 (L B1 ) To Ir (L) A4320-35-52 ) 2 (L B474 ) A group of groups;
when the compound has the formula Ir (L Ai-w-m ) 2 (L Cj-I ) When the compound is selected from Ir (L) A1-1-1 ) 2 (L C1-I ) To Ir (L) A43320-35-52 ) 2 (L C1416-I ) A group of groups; and is also provided with
When the compound has the formula Ir (L Ai-w-m ) 2 (L Cj-II ) When the compound is selected from Ir (L) A1-1-1 ) 2 (L C1-II ) To Ir (L) A4320-35-52 ) 2 (L C1416-II ) A group of groups;
wherein each L Bk Has a structure defined as follows:
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wherein each L Cj-I With the basisIs of a structure of (2); and is also provided with
Each L Cj-II With the basisWherein for L Cj-I And L Cj-II Each L of (a) Cj ,R 201 And R is 202 Each independently defined as follows:
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wherein R is D1 To R D246 The structure is as follows:
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12. the compound of claim 1, wherein the compound is selected from the group consisting of:
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13. The compound of claim 8, wherein the compound has formula V:
wherein:
M 1 is Pd or Pt;
moieties E and F are each independently a single or multiple ring structure comprising 5-and/or 6-membered carbocycles or heterocycles;
Z 1a and Z 2a Each independently is C or N;
K 1 and K 2 Each independently selected from the group consisting of a direct bond, O, and S, wherein at least two are direct bonds;
L 1 、L 2 and L 3 Each independently selected from the group consisting of: direct bond, BR, BRR', NR,
PR、P(O)R、O、S、Se、C=O、C=S、C=Se、C=NR、C=CRR'、S=O、SO 2 、CR、
CRR ', siRR ', geRR ', alkylene, cycloalkyl, aryl, cycloalkylene, arylene, heteroarylene, and combinations thereof, wherein L 1 And L 2 At least one of which is present;
R E and R is F Each independently represents zero substitution, a single substitution, or up to a maximum allowable number of substitutions to its associated ring;
R、R'、R E and R is F Independently hydrogen or a substituent selected from the group consisting of: deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silicon, boron, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, thio, and combinations thereof; and is also provided with
Where chemically feasible, two adjacent R' s A 、R B 、R C 、R E And R is F Can be joined or fused together to form a ring.
14. An organic light emitting device, comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1.
15. A consumer product comprising an organic light emitting device, the organic light emitting device comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1.
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US18/326,729 US20230422595A1 (en) | 2022-06-20 | 2023-05-31 | Organic electroluminescent materials and devices |
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