US20230354692A1 - Organic electroluminescent materials and devices - Google Patents
Organic electroluminescent materials and devices Download PDFInfo
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- US20230354692A1 US20230354692A1 US18/345,758 US202318345758A US2023354692A1 US 20230354692 A1 US20230354692 A1 US 20230354692A1 US 202318345758 A US202318345758 A US 202318345758A US 2023354692 A1 US2023354692 A1 US 2023354692A1
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- 239000000463 material Substances 0.000 title description 83
- 239000003446 ligand Substances 0.000 claims abstract description 150
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000003118 aryl group Chemical group 0.000 claims abstract description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 41
- 125000001424 substituent group Chemical group 0.000 claims abstract description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 35
- 229910052751 metal Inorganic materials 0.000 claims abstract description 33
- 239000002184 metal Substances 0.000 claims abstract description 33
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 18
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 1528
- 239000010410 layer Substances 0.000 claims description 89
- -1 amino, silyl Chemical group 0.000 claims description 56
- 239000002019 doping agent Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
- 229910052805 deuterium Inorganic materials 0.000 claims description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
- 150000002527 isonitriles Chemical class 0.000 claims description 17
- 150000002825 nitriles Chemical class 0.000 claims description 17
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 16
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 15
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 150000001735 carboxylic acids Chemical class 0.000 claims description 13
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 238000006467 substitution reaction Methods 0.000 claims description 13
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- 150000004820 halides Chemical class 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000005580 triphenylene group Chemical group 0.000 claims description 9
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- 150000004696 coordination complex Chemical class 0.000 claims description 7
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 239000013522 chelant Substances 0.000 claims description 5
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
- 238000005286 illumination Methods 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 2
- 230000003190 augmentative effect Effects 0.000 claims description 2
- 125000003636 chemical group Chemical group 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 238000001126 phototherapy Methods 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 230000011664 signaling Effects 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 230000000903 blocking effect Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000004888 barrier function Effects 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 10
- SKRSSNLRBLWLCE-UHFFFAOYSA-N 6-bromo-1-methoxynaphthalene Chemical compound BrC1=CC=C2C(OC)=CC=CC2=C1 SKRSSNLRBLWLCE-UHFFFAOYSA-N 0.000 description 9
- LQRPJZVXEIBBNI-UHFFFAOYSA-N FC(S(=O)(=O)OC1=CC=CC2=CC3=C(OC4=C3C=CC=C4)C=C12)(F)F Chemical compound FC(S(=O)(=O)OC1=CC=CC2=CC3=C(OC4=C3C=CC=C4)C=C12)(F)F LQRPJZVXEIBBNI-UHFFFAOYSA-N 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- YHEKYRZCJRSPFY-UHFFFAOYSA-N C1=CC=CC2=C1C1=C(O2)C=C2C(=CC=CC2=C1)O Chemical compound C1=CC=CC2=C1C1=C(O2)C=C2C(=CC=CC2=C1)O YHEKYRZCJRSPFY-UHFFFAOYSA-N 0.000 description 7
- NIWAHZWJXKRHHA-UHFFFAOYSA-N COC1=CC=CC2=CC3=C(OC4=C3C=CC=C4)C=C12 Chemical compound COC1=CC=CC2=CC3=C(OC4=C3C=CC=C4)C=C12 NIWAHZWJXKRHHA-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 229960005544 indolocarbazole Drugs 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 230000005693 optoelectronics Effects 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- RFYLFKPVMAIRAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-naphtho[7,6-b][1]benzofuran-7-yl-1,3,2-dioxaborolane Chemical compound CC1(OB(OC1(C)C)C1=CC=CC2=CC3=C(OC4=C3C=CC=C4)C=C12)C RFYLFKPVMAIRAH-UHFFFAOYSA-N 0.000 description 4
- ZDQCEUGLIDNPHB-UHFFFAOYSA-N CC=1C=NC(=NC=1)C1=CC=CC2=CC3=C(OC4=C3C=CC=C4)C=C12 Chemical compound CC=1C=NC(=NC=1)C1=CC=CC2=CC3=C(OC4=C3C=CC=C4)C=C12 ZDQCEUGLIDNPHB-UHFFFAOYSA-N 0.000 description 4
- YMQHQQWOZIFHMO-UHFFFAOYSA-N COC1=C2C=CC(=CC2=CC=C1)C1=C(C=CC=C1)O Chemical compound COC1=C2C=CC(=CC2=CC=C1)C1=C(C=CC=C1)O YMQHQQWOZIFHMO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-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
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-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
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 3
- GWJFDOLFGKVCLF-UHFFFAOYSA-N 5-methyl-2-naphthalen-1-ylpyrimidine Chemical compound CC1=CN=C(N=C1)C1=CC=CC2=C1C=CC=C2 GWJFDOLFGKVCLF-UHFFFAOYSA-N 0.000 description 3
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 3
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 3
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Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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Definitions
- the present invention relates to compounds for use as emitters, and devices, such as organic light emitting diodes, including the same.
- Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
- OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
- phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels.
- the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs.
- the white OLED can be either a single EML device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art.
- a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy) 3 , which has the following structure:
- organic includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices.
- Small molecule refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the “small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety.
- the core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter.
- a dendrimer may be a “small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
- top means furthest away from the substrate, while “bottom” means closest to the substrate.
- first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is “in contact with” the second layer.
- a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
- solution processable means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
- a ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material.
- a ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
- a first “Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or “higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level.
- IP ionization potentials
- a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative).
- a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative).
- the LUMO energy level of a material is higher than the HOMO energy level of the same material.
- a “higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a “lower” HOMO or LUMO energy level.
- a first work function is “greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a “higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
- a compound comprising a first ligand L A having the Formula selected from the group consisting of
- Formula IC is provided.
- Formulae IA, IB, and IC are provided.
- ring B and C are each independently a 5-membered or 6-membered aromatic or heteroaromatic ring;
- R A , R B , R C , and R D each independently represent mono to the maximum possible number of substituents, or no substituent;
- Z 1 and Z 2 are each independently selected from the group consisting of C and N;
- X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are each independently selected from the group consisting of C and N;
- X 1 , X 2 , X 3 , or X 4 is C when it forms a direct bond to Z 2 ;
- Y is selected from the group consisting of CRR′, NR′, O, S, and Se;
- R, R′, R A , R B , R C , and R D are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- any two substituents are optionally joined or fused into a ring
- the ligand L A is coordinated to a metal M by the dashed lines to form a 5-membered chelate ring;
- M does not form a direct bond to X 1 in Formula IB; wherein M does not form a direct bond to X 4 in Formula IC;
- the metal M can be coordinated to other ligands
- the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
- an organic light emitting device can include an anode; a cathode; and an organic layer, disposed between the anode and the cathode, where the organic layer includes a compound comprising a first ligand L A of Formula IA, Formula IB, or Formula IC, as described herein.
- a consumer product comprising the OLED is also disclosed.
- FIG. 1 shows an organic light emitting device
- FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.
- an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode.
- the anode injects holes and the cathode injects electrons into the organic layer(s).
- the injected holes and electrons each migrate toward the oppositely charged electrode.
- an “exciton,” which is a localized electron-hole pair having an excited energy state is formed.
- Light is emitted when the exciton relaxes via a photoemissive mechanism.
- the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
- the initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
- FIG. 1 shows an organic light emitting device 100 .
- 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 barrier layer 170 .
- Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164 .
- Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.
- each of these layers are available.
- a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety.
- An example of a p-doped hole transport layer is m-MTDATA doped with F 4 -TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety.
- Examples of emissive 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 at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety.
- the theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No.
- 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 .
- Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230 , 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 device 100 .
- FIGS. 1 and 2 The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide 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 achieved by combining the various layers described in different ways, or 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 various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers.
- 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.
- 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 FIGS. 1 and 2 .
- OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety.
- PLEDs polymeric materials
- OLEDs having a single organic layer may be used.
- OLEDs may be stacked, for example as described in U.S. Pat. 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 FIGS. 1 and 2 .
- 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 Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.
- any of the layers of the various embodiments may be deposited by any suitable method.
- preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety.
- OVPD organic vapor phase deposition
- OJP organic vapor jet printing
- Other suitable deposition methods include spin coating and other solution based processes.
- Solution based processes are preferably carried out in nitrogen or an inert atmosphere.
- preferred methods include thermal evaporation.
- Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and organic vapor jet printing (OVJP). Other methods may also be used.
- the materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing.
- Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processability than those having symmetric structures, because asymmetric materials 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 in accordance with embodiments of the present invention may further optionally comprise a barrier layer.
- a barrier layer One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc.
- the barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an 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 compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer.
- the barrier layer may incorporate an inorganic or an organic compound or both.
- the preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties.
- the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time.
- the weight ratio of polymeric 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 created from the same precursor material.
- the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.
- Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices such as discrete light source devices or lighting panels, etc. that can be utilized by the end-user product manufacturers. Such electronic component modules can optionally include the driving electronics and/or power source(s). Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein.
- a consumer product comprising an OLED that includes the compound of the present disclosure in the organic layer in the OLED is disclosed.
- Such consumer products would include any kind of products that include one or more light source(s) and/or one or more of some type of visual displays.
- 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, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, micro-displays (displays that are less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, a light therapy device, and a sign.
- control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.), but could be used outside this temperature range, for example, from ⁇ 40 degree C. to +80 degree C.
- the materials and structures described herein may have applications in devices other than OLEDs.
- other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures.
- organic devices such as organic transistors, may employ the materials and structures.
- halo halogen
- halide halogen
- fluorine chlorine, bromine, and iodine
- acyl refers to a substituted carbonyl radical (C(O)—R s ).
- esters refers to a substituted oxycarbonyl (—O—C(O)—R s or —C(O)—O—R s ) radical.
- ether refers to an —OR s radical.
- sulfanyl or “thio-ether” are used interchangeably and refer to a —SR s radical.
- sulfinyl refers to a —S(O)—R s radical.
- sulfonyl refers to a —SO 2 —R s radical.
- phosphino refers to a —P(R s ) 3 radical, wherein each R s can be same or different.
- sil refers to a —Si(R s ) 3 radical, wherein each R s can be same or different.
- R s can be hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combination thereof.
- Preferred R s is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combination thereof.
- alkyl refers to and includes both straight and branched chain alkyl radicals.
- Preferred alkyl groups are those containing from one to fifteen carbon atoms and includes methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, the alkyl group is optionally substituted.
- cycloalkyl refers to and includes monocyclic, polycyclic, and spiro alkyl radicals.
- Preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Additionally, the cycloalkyl group is optionally substituted.
- heteroalkyl or “heterocycloalkyl” refer to an alkyl or a cycloalkyl radical, respectively, having at least one carbon atom replaced by a heteroatom.
- the at least one heteroatom is selected from O, S, N, P, B, Si and Se, preferably, O, S or N.
- the heteroalkyl or heterocycloalkyl group is optionally substituted.
- alkenyl refers to and includes both straight and branched chain alkene radicals.
- Alkenyl groups are essentially alkyl groups that include at least one carbon-carbon double bond in the alkyl chain.
- Cycloalkenyl groups are essentially cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalkyl ring.
- heteroalkenyl refers to an alkenyl radical having at least one carbon atom replaced by a heteroatom.
- 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 two to fifteen carbon atoms. Additionally, the alkenyl, cycloalkenyl, or heteroalkenyl group is optionally substituted.
- alkynyl refers to and includes both straight and branched chain alkyne radicals. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group is optionally substituted.
- aralkyl or “arylalkyl” are used interchangeably and refer to an alkyl group that is substituted with an aryl group. Additionally, the aralkyl group is optionally substituted.
- heterocyclic group refers to and includes aromatic and non-aromatic cyclic radicals containing at least one heteroatom.
- the at least one heteroatom is selected from O, S, N, P, B, Si, and Se, preferably, O, S, or N.
- Hetero-aromatic cyclic radicals may be used interchangeably with heteroaryl.
- Preferred hetero-non-aromatic cyclic groups are those containing 3 to 7 ring atoms which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperidino, pyrrolidino, and the like, and cyclic ethers/thio-ethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. Additionally, the heterocyclic group may be optionally substituted.
- aryl refers to and includes both single-ring aromatic hydrocarbyl groups and polycyclic aromatic ring systems.
- the polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is an aromatic hydrocarbyl group, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls.
- Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Especially preferred is an aryl group having six carbons, ten carbons or twelve carbons.
- Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group is optionally substituted.
- heteroaryl refers to and includes both single-ring aromatic groups and polycyclic aromatic ring systems that include at least one heteroatom.
- the heteroatoms include, but are not limited to O, S, N, P, B, Si, and Se. In many instances, O, S, or N are the preferred heteroatoms.
- Hetero-single ring aromatic systems are preferably single rings with 5 or 6 ring atoms, and the ring can have from one to six heteroatoms.
- the hetero-polycyclic ring systems can have two or more rings in which two atoms are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls.
- the hetero-polycyclic aromatic ring systems can have from one to six heteroatoms per ring of the polycyclic aromatic ring system.
- Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably 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, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, qui
- aryl and heteroaryl groups listed above the groups of triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and the respective aza-analogs of each thereof are of particular interest.
- alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl, as used herein, are independently unsubstituted, or independently substituted, with one or more general substituents.
- the general substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
- the preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
- the preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, and combinations thereof.
- the more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
- substituted refers to a substituent other than H that is bonded to the relevant position, e.g., a carbon.
- R 1 represents mono-substituted
- R 1 represents di-substituted
- R 1 is hydrogen for all available positions.
- the maximum number of substitutions possible in a structure will depend on the number of atoms with available valencies.
- substitution includes a combination of two to four of the listed groups.
- substitution includes a combination of two to three groups.
- substitution includes a combination of two groups.
- Preferred combinations of substituent groups are those that contain up to fifty atoms that are not hydrogen or deuterium, or those which include up to forty atoms that are not hydrogen or deuterium, or those that include up to thirty atoms that are not hydrogen or deuterium. In many instances, a preferred combination of substituent groups will include up to twenty atoms that are not hydrogen or deuterium.
- aza-dibenzofuran i.e. aza-dibenzofuran, aza-dibenzothiophene, etc.
- azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline.
- deuterium refers to an isotope of hydrogen.
- Deuterated compounds can be readily prepared using methods known in the art. For example, U.S. Pat. No. 8,557,400, Patent Pub. No. WO 2006/095951, and U.S. Pat. Application Pub. No. US 2011/0037057, which are hereby incorporated by reference in their entireties, describe the making of deuterium-substituted organometallic complexes. Further reference is made to Ming Yan, et al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Reviews) 2007, 46, 7744-65, which are incorporated by reference in their entireties, describe the deuteration of the methylene hydrogens in benzyl amines and efficient pathways to replace aromatic ring hydrogens with deuterium, respectively.
- a compound comprising a first ligand L A having the Formula selected from the group consisting of
- Formula IC is provided.
- Formulae IA, IB, and IC are provided.
- ring B and C are each independently a 5-membered or 6-membered aromatic or heteroaromatic ring;
- R A , R B , R C , and R D each independently represent mono to the maximum possible number of substituents, or no substituent;
- Z 1 and Z 2 are each independently selected from the group consisting of C and N;
- X 1 , X 2 , X 3 , X 4 , X 5 , and X 6 are each independently selected from the group consisting of C and N;
- X 1 , X 2 , X 3 , or X 4 is C when it forms a direct bond to Z 2 ;
- Y is selected from the group consisting of CRR′, NR′, O, S, and Se;
- R, R′, R A , R B , R C , and R D are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- any two substituents are optionally joined or fused into a ring
- the ligand L A is coordinated to a metal M by the dashed lines to form a 5-membered chelate ring;
- M does not form a direct bond to X 1 in Formula IB; wherein M does not form a direct bond to X 4 in Formula IC;
- the metal M can be coordinated to other ligands
- the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
- ring B can be a ring system comprising two fused rings, such as naphthalene, benzimidazole, etc.
- the maximum substitutions for R B could be hexa- or penta-substitutions, respectively.
- metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Au, and Cu. In some embodiments, metal M is Ir or Pt.
- R, R′, R A , R B , R C , and R D are each independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
- the compound is homoleptic. In some embodiments, the compound is heteroleptic.
- Y is O.
- X 1 through X 6 are each independently C. In some embodiments, X 1 through X 4 are each independently CR.
- ring C is a fused benzene ring.
- ring B is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, benzene imidazole, pyrazole, triazole, pyrrole, oxazole, thiazole, and imidazole derived carbene.
- ring A is benezene and ring B is pyridine with Z 1 as N.
- ring A is pyridine with N coordinated to metal, and ring B is benezene.
- the first ligand L A is selected from the group consisting of:
- Ra is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alk ynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
- the first ligand L A is selected from the group consisting of L A1 through L A4560 , wherein L A1 through L A4780 have a structure of Formula II:
- R 1 , R 2 , X and Y are defined as:
- R 2 , R 3 and Y are defined as provided below:
- R 2 , R 4 , Y, and X are defined as provided below:
- R 1 , R 2 , X, and Y are defined as provided below:
- R 2 , R 3 , and Y are defined as provided below:
- R 2 , R 4 , and Y are defined as provided below:
- R 1 , R 2 , and X are defined as provided below:
- R 2 , R 3 , and Y are defined as provided below:
- R 2 , R 4 , Y, and Z are defined as provided below:
- R 1 , R 2 , and Y are defined as provided below:
- R 2 , R 3 , and Y are defined as provided below:
- R 2 , R 4 , Y, and Z are defined as provided below:
- R 1 , R 5 , X, and Y are defined as provided below:
- R 3 , R 5 , and Y are defined as provided below:
- R 4 , R 5 , Y, and Z are defined as provided below:
- R 1 , R 5 , X, and Y are defined as provided below:
- R 3 , R 5 , and Y are defined as provided below:
- R 4 , R 5 , Y, and Z are defined as provided below:
- R 1 , R 5 , Y, and X are defined as provided below:
- R 3 , R 5 , and Y are defined as provided below:
- R 4 , R 5 , Y, and Z are defined as provided below:
- R 1 , R 5 , X, and Y are defined as provided below:
- R 3 , R 5 , and Y are defined as provided below:
- R 4 , R 5 , Y, and Z are defined as provided below:
- R 1 , R 5 , X, and Y are defined as provided below:
- R 3 , R 5 , and Y are defined as provided below:
- R 4 , R 5 , Y, and Z are defined as provided below:
- R 1 , R 5 , X, and Y are defined as provided below:
- R 3 , R 5 , and Y are defined as provided below:
- R 4 , R 5 , Y, and Z are defined as provided below:
- R 1 , R 2 , R 3 , and Y are defined as provided below:
- R A1 to R A52 have the following structures:
- the compound has a formula of M(L A ) x (L B ) y (L C ) z where L B and L C are each a bidentate ligand; x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.
- 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 ); and ligands L A , L B , and L C are different from each other.
- the compound has a formula of Pt(L A )(L B ), where L A and L B can be the same or different.
- L A and L B are connected to form a tetradentate ligand.
- L A and L B are connected at two places to form a macrocyclic tetradentate ligand.
- ligands L B and L C are each independently selected from the group consisting of
- each Y 1 to Y 13 is independently selected from the group consisting of carbon and nitrogen;
- R 1 and R 2 are optionally fused or joined to form a ring
- each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- R 1 , R 2 , R a , R b , R c , and R d are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
- any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.
- ligands L B and L C are each independently selected from the group consisting of
- L C1 through L C1260 are based on a structure of Formula X,
- R 1 , R 2 , and R 3 are defined as:
- an organic light emitting device can include an anode; a cathode; and an organic layer, disposed between the anode and the cathode, where the organic layer includes a compound comprising a first ligand L A of Formula IA, Formula IB, or Formula IC, as described herein.
- a consumer product comprising an OLED as described herein is described.
- the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved. In some embodiments, the OLED is transparent or semi-transparent. In some embodiments, the OLED further comprises a layer comprising carbon nanotubes.
- the OLED further comprises a layer comprising a delayed fluorescent emitter.
- the OLED comprises a RGB pixel arrangement or white plus color filter pixel arrangement.
- the OLED is a mobile device, a hand held device, or a wearable device.
- the OLED is a display panel having less than 10 inch diagonal or 50 square inch area.
- the OLED is a display panel having at least 10 inch diagonal or 50 square inch area.
- the OLED is a lighting panel.
- an emissive region in an OLED e.g., the organic layer described herein
- the emissive region comprises a compound comprising a first ligand L A of Formula IA, Formula IB, or Formula IC, as described herein.
- the compound can be an emissive dopant.
- the compound can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence; see, e.g., U.S. application Ser. No. 15/700,352, which is hereby incorporated by reference in its entirety), triplet-triplet annihilation, or combinations of these processes.
- TADF also referred to as E-type delayed fluorescence
- a formulation comprising the compound described herein is also disclosed.
- the OLED disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel.
- the organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.
- the organic layer can also include a host.
- a host In some embodiments, two or more hosts are preferred.
- the hosts used maybe a) bipolar, b) electron transporting, c) hole transporting or d) wide band gap materials that play little role in charge transport.
- the host can include a metal complex.
- the host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan.
- Any substituent in the host can be an unfused substituent independently selected from the group consisting of 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 ⁇ C—C n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , and C n H 2n —Ar 1 , or the host has no substitutions.
- n can range from 1 to 10; and Ar 1 and Ar 2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.
- the host can be an inorganic compound.
- a Zn containing inorganic material e.g. ZnS.
- the host can be a compound comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
- the host can include a metal complex.
- the host can be, but is not limited to, a specific compound selected from the group consisting of:
- a formulation that comprises the novel compound disclosed herein is described.
- the formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, electron blocking material, hole blocking material, and an electron transport material, disclosed herein.
- the materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device.
- emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present.
- the materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
- a charge transport layer can be doped with conductivity dopants to substantially alter its density of charge carriers, which will in turn alter its conductivity.
- the conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor may also be achieved.
- Hole-transporting layer can be doped by p-type conductivity dopants and n-type conductivity dopants are used in the electron-transporting layer.
- Non-limiting examples of the conductivity dopants that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804,
- a hole injecting/transporting material to be used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material.
- the material include, but are not limited to: a phthalocyanine or porphyrin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and silane derivatives; a metal oxide derivative, such as MoO x ; a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.
- aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:
- Each of Ar 1 to Ar 9 is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the 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, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine
- Each Ar may be unsubstituted or may be substituted by a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
- a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkeny
- Ar 1 to Ar 9 is independently selected from the group consisting of:
- k is an integer from 1 to 20;
- X 101 to X 108 is C (including CH) or N;
- Z 101 is NAr 1 , O, or S;
- Ar 1 has the same group defined above.
- metal complexes used in HIL or HTL include, but are not limited to the following general formula:
- Met is a metal, which can have an atomic weight greater than 40;
- (Y 101 -Y 102 ) is a bidentate ligand, Y 101 and Y 102 are independently selected from C, N, O, P, and S;
- L 101 is an ancillary ligand;
- k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and
- k′+k′′ is the maximum number of ligands that may be attached to the metal.
- (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 a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc + /Fc couple less than about 0.6 V.
- Non-limiting examples of the HIL and HTL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473, TW201139402, U.S. Ser.
- An electron blocking layer may be used to reduce the number of electrons and/or excitons that leave the emissive layer.
- the presence of such a blocking layer in a device may result in substantially higher efficiencies, and/or longer lifetime, as compared to a similar device lacking a blocking layer.
- a blocking layer may be used to confine emission to a desired region of an OLED.
- 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.
- the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the EBL interface.
- the compound used in EBL contains the same molecule or the same functional groups used as one of the hosts described below.
- the light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material.
- the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria is satisfied.
- metal complexes used as host are preferred to have the following general formula:
- Met is a metal
- (Y 103 -Y 104 ) is a bidentate ligand, Y 103 and Y 104 are independently selected from C, N, O, P, and S
- L 101 is an another ligand
- k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal
- k′+k′′ is the maximum number of ligands that may be attached to the metal.
- the metal complexes are:
- (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.
- Met is selected from Ir and Pt.
- (Y 103 -Y 104 ) is a carbene ligand.
- organic compounds used as host are selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the 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, oxatriazole, dioxazole, thiadiazole, pyridine
- Each option within each group may be unsubstituted or may be substituted by a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
- the host compound contains at least one of the following groups in the molecule:
- R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above.
- k is an integer from 0 to 20 or 1 to 20.
- X 101 to X 108 are independently selected from C (including CH) or N.
- Z 101 and Z 102 are independently selected from NR 101 , O, or S.
- Non-limiting examples of the host materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, U.S.
- One or more additional emitter dopants may be used in conjunction with the compound of the present disclosure.
- the additional emitter dopants are not particularly limited, and any compounds may be used as long as the compounds are typically used as emitter materials.
- suitable emitter materials include, but are not limited to, compounds which can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.
- Non-limiting examples of the emitter materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, U.S. Ser. No. 06/699,599, U.S. Ser. No.
- a hole blocking layer may be used to reduce the number of holes and/or excitons that leave the emissive layer.
- the presence of such a blocking layer in a device may result in substantially higher efficiencies and/or longer lifetime as compared to a similar device lacking a blocking layer.
- a blocking layer may be used to confine emission to a desired region of an OLED.
- the HBL material has a lower HOMO (further from the vacuum level) and/or higher triplet energy than the emitter closest to the HBL interface.
- the HBL material has a lower HOMO (further from the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the HBL interface.
- compound used in HBL contains the same molecule or the same functional groups used as host described above.
- compound used in HBL contains at least one of the following groups in the molecule:
- Electron transport layer may include a material capable of transporting electrons. 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 complexes or organic compounds may be used as long as they are typically used to transport electrons.
- compound used in ETL contains at least one of the following groups in the molecule:
- R 101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above.
- Ar 1 to Ar 3 has the similar definition as Ar's mentioned above.
- k is an integer from 1 to 20.
- X 101 to X 108 is selected from C (including CH) or N.
- the metal complexes used in ETL contains, but not limit to the following general formula:
- (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L 101 is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.
- Non-limiting examples of the ETL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose 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, U.S.
- the CGL plays an essential role in the performance, which is composed of an n-doped layer and a p-doped layer for injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the bipolar currents reach a steady state gradually.
- Typical CGL materials include n and p conductivity dopants used in the transport layers.
- the hydrogen atoms can be partially or fully deuterated.
- any specifically listed substituent such as, without limitation, methyl, phenyl, pyridyl, etc. may be undeuterated, partially deuterated, and fully deuterated versions thereof.
- classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also may be undeuterated, partially deuterated, and fully deuterated versions thereof.
- 6-Bromonaphthalen-1-ol (compound 1, 10 g, 44.8 mmol) was dissolved in dry acetone (180 mL) under a room temperature ( ⁇ 22° C.) atmosphere in a 500 mL, 3-necked round bottomed flask topped with a reflux condenser. Then, potassium carbonate (12.39 g, 90 mmol) and methyl iodide (5.61 ml, 90 mmol) were added and the reaction mixture was stirred at 65° C. for 18 hours. The reaction was cooled to room temperature ( ⁇ 22° C.), causing a white solid to precipitate from the reaction mixture. The precipitate was then was filtered off and the filtrate was concentrated under vacuum.
- reaction mixture was then poured into water-ice and extracted with dichloromethane (3 ⁇ 100 mL), with 10 mL of acetone to facilitate solubility, dried over MgSO 4 , and the solvents removed. A red solid was obtained which was further triturated with iso-hexane to afford compound 6 of Scheme I as an off-white solid (14.42 g, 60.9 mmol, 95% yield).
- Step 6 Synthesis of 4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-7-yl)-1,3,2-dioxaborolane (8)
- Dopant A was synthesized according to the reaction below.
- Dopant B 5-methyl-2-(naphthalen-1-yl)pyrimnidine
- Dopant B was synthesized according to the equation below.
- All example devices were fabricated by high vacuum ( ⁇ 10-7 Torr) thermal evaporation.
- the anode electrode was 1150 ⁇ of indium tin oxide (ITO).
- the cathode consisted of 10 ⁇ of Liq (8-hydroxyquinoline lithium) followed by 1,000 ⁇ of Al. All devices were encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box ( ⁇ 1 ppm of H 2 O and O 2 ) immediately after fabrication, and a moisture getter was incorporated inside the package.
- the organic stack of the device examples consisted of sequentially, from the ITO surface, 100 k of HATCN as the hole injection layer (HIL); 450 ⁇ of HTL-1 as the hole transporting layer (HTL); 400 ⁇ of an emissive layer (EML) comprising Host-1 as a host, SD-1 as a stability dopant (18%), and Dopant A or Dopant B as the emitter (3%); 350 ⁇ of Liq doped with 35% of ETM-1 as the ETL; and 10 ⁇ of Liq as the electron injection layer (EIL).
- the stability dopant was added to the electron-transporting host to help transport positive charge in the emissive layer.
- the electroluminescence (EL) and current density-voltage-luminance (JVL) performance of the devices was measured. The device lifetimes were evaluated at a current density of 80 mA/cm 2 .
- Table I The results are summarized in Table I and compare the performance of Dopant A in Example 1 vs. Dopant B in Comparative Example 2. Both dopants afford devices with identical voltages and external quantum efficiencies. However, Dopant A provides narrower line width (full width at half maximum, FWHM) and significantly longer device lifetime than Dopant B.
- the emission wavelength of Dopant A is also red-shifted versus Dopant B, which is desirable for application of the dopants of the present invention as red emissive materials in OLED devices.
Abstract
A compound comprising a first ligand LA having a Formula selected from:is disclosed. In the Formulas rings B and C are 5-membered or 6-membered aromatic or heteroaromatic ring; Z1, Z2, X1, X2, X3, X4, X5, and X6 are each C or N, but X1, X2, X3, or X4 is C when it forms a direct bond to Z2; Y is selected from CRR′, NR′, O, S, and Se; R, R′, RA, RB, RC, and RD are each selected from a variety of substituents; the ligand LA is coordinated to a metal M by the dashed lines, and optionally to other ligands. Organic light emitting devices and consumer products containing the compounds are also disclosed.
Description
- This application is a continuation of copending U.S. patent application Ser. No. 16/113,587, filed Aug. 27, 2018, which claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Application No. 62/560,902, filed Sep. 20, 2017, the entire contents of which are incorporated herein by reference.
- The present invention relates to compounds for use as emitters, and devices, such as organic light emitting diodes, including the same.
- Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.
- OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.
- One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Alternatively the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can be either a single EML device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art.
- One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy)3, which has the following structure:
- In this, and later figures herein, we depict the dative bond from nitrogen to metal (here, Ir) as a straight line.
- As used herein, the term “organic” includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. “Small molecule” refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the “small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.
- As used herein, “top” means furthest away from the substrate, while “bottom” means closest to the substrate. Where a first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is “in contact with” the second layer. For example, a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.
- As used herein, “solution processable” means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.
- A ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.
- As used herein, and as would be generally understood by one skilled in the art, a first “Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or “higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). On a conventional energy level diagram, with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A “higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a “lower” HOMO or LUMO energy level.
- As used herein, and as would be generally understood by one skilled 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. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a “higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.
- More details on OLEDs, and the definitions described above, can be found in U.S. Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.
- According to an aspect of the present disclosure, a compound comprising a first ligand LA having the Formula selected from the group consisting of
- Formula IC, is provided. In Formulae IA, IB, and IC:
- ring B and C are each independently a 5-membered or 6-membered aromatic or heteroaromatic ring;
- RA, RB, RC, and RD each independently represent mono to the maximum possible number of substituents, or no substituent;
- Z1 and Z2 are each independently selected from the group consisting of C and N;
- X1, X2, X3, X4, X5, and X6 are each independently selected from the group consisting of C and N;
- X1, X2, X3, or X4 is C when it forms a direct bond to Z2;
- Y is selected from the group consisting of CRR′, NR′, O, S, and Se;
- R, R′, RA, RB, RC, and RD are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- any two substituents are optionally joined or fused into a ring;
- the ligand LA is coordinated to a metal M by the dashed lines to form a 5-membered chelate ring;
- wherein M does not form a direct bond to X1 in Formula IB;
wherein M does not form a direct bond to X4 in Formula IC; - the metal M can be coordinated to other ligands; and
- the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
- In some embodiments, an organic light emitting device (OLED) is described. The OLED can include an anode; a cathode; and an organic layer, disposed between the anode and the cathode, where the organic layer includes a compound comprising a first ligand LA of Formula IA, Formula IB, or Formula IC, as described herein.
- A consumer product comprising the OLED is also disclosed.
-
FIG. 1 shows an organic light emitting device. -
FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer. - Generally, an OLED comprises 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(s). The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an “exciton,” which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.
- The initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.
- More recently, OLEDs having emissive materials that emit light from triplet states (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, vol. 395, 151-154, 1998; (“Baldo-I”) and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”), are incorporated by reference in their entireties. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704 at cols. 5-6, which are incorporated by reference.
-
FIG. 1 shows an organiclight emitting device 100. The figures are not necessarily drawn to scale.Device 100 may include asubstrate 110, ananode 115, ahole injection layer 120, ahole transport layer 125, anelectron blocking layer 130, anemissive layer 135, ahole blocking layer 140, anelectron transport layer 145, anelectron injection layer 150, aprotective layer 155, acathode 160, and abarrier layer 170.Cathode 160 is a compound cathode having a firstconductive layer 162 and a secondconductive layer 164.Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference. - More examples for 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 entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive 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 at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.
-
FIG. 2 shows aninverted OLED 200. The device includes asubstrate 210, acathode 215, anemissive layer 220, ahole transport layer 225, and ananode 230.Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, anddevice 200 hascathode 215 disposed underanode 230,device 200 may be referred to as an “inverted” OLED. Materials similar to those described with respect todevice 100 may be used in the corresponding layers ofdevice 200.FIG. 2 provides one example of how some layers may be omitted from the structure ofdevice 100. - The simple layered structure illustrated in
FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide 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 achieved by combining the various layers described in different ways, or 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 various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, indevice 200,hole transport layer 225 transports holes and injects holes intoemissive 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 toFIGS. 1 and 2 . - Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example as described in U.S. Pat. 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
FIGS. 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 Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties. - Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such 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. Solution based processes are preferably carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and organic vapor jet printing (OVJP). Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processability than those having symmetric structures, because asymmetric materials 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 in accordance with embodiments of the present invention may further optionally comprise a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc. The barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an 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 compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic or an organic compound or both. The preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties. To be considered a “mixture”, the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time. The weight ratio of polymeric 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 created from the same precursor material. In one example, the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.
- Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices such as discrete light source devices or lighting panels, etc. that can be utilized by the end-user product manufacturers. Such electronic component modules can optionally include the driving electronics and/or power source(s). Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein. A consumer product comprising an OLED that includes the compound of the present disclosure in the organic layer in the OLED is disclosed. Such consumer products would include any kind of products that include one or more light source(s) and/or one or more of some type of visual displays. 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, mobile phones, tablets, phablets, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, micro-displays (displays that are less than 2 inches diagonal), 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising multiple displays tiled together, theater or stadium screen, a light therapy device, and a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.), but could be used outside this temperature range, for example, from −40 degree C. to +80 degree C.
- The materials and structures described herein may have applications 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.
- The terms “halo,” “halogen,” and “halide” are used interchangeably and refer to fluorine, chlorine, bromine, and iodine.
- The term “acyl” refers to a substituted carbonyl radical (C(O)—Rs).
- The term “ester” refers to a substituted oxycarbonyl (—O—C(O)—Rs or —C(O)—O—Rs) radical.
- The term “ether” refers to an —ORs radical.
- The terms “sulfanyl” or “thio-ether” are used interchangeably and refer to a —SRs radical.
- The term “sulfinyl” refers to a —S(O)—Rs radical.
- The term “sulfonyl” refers to a —SO2—Rs radical.
- The term “phosphino” refers to a —P(Rs)3 radical, wherein each Rs can be same or different.
- The term “silyl” refers to a —Si(Rs)3 radical, wherein each Rs can be same or different.
- In each of the above, Rs can be hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, and combination thereof. Preferred Rs is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and combination thereof.
- The term “alkyl” refers to and includes both straight and branched chain alkyl radicals. Preferred alkyl groups are those containing from one to fifteen carbon atoms and includes methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, the alkyl group is optionally substituted.
- The term “cycloalkyl” refers to and includes monocyclic, polycyclic, and spiro alkyl radicals. Preferred cycloalkyl groups are those containing 3 to 12 ring carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and the like. Additionally, the cycloalkyl group is optionally substituted.
- The terms “heteroalkyl” or “heterocycloalkyl” refer to an alkyl or a cycloalkyl radical, respectively, having at least one carbon atom replaced by a heteroatom. Optionally the at least one heteroatom is selected from O, S, N, P, B, Si and Se, preferably, O, S or N. Additionally, the heteroalkyl or heterocycloalkyl group is optionally substituted.
- The term “alkenyl” refers to and includes both straight and branched chain alkene radicals. Alkenyl groups are essentially alkyl groups that include at least one carbon-carbon double bond in the alkyl chain. Cycloalkenyl groups are essentially cycloalkyl groups that include at least one carbon-carbon double bond in the cycloalkyl ring. The term “heteroalkenyl” as used herein refers to an alkenyl radical having at least one carbon atom replaced by 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 two to fifteen carbon atoms. Additionally, the alkenyl, cycloalkenyl, or heteroalkenyl group is optionally substituted.
- The term “alkynyl” refers to and includes both straight and branched chain alkyne radicals. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group is optionally substituted.
- The terms “aralkyl” or “arylalkyl” are used interchangeably and refer to an alkyl group that is substituted with an aryl group. Additionally, the aralkyl group is optionally substituted.
- The term “heterocyclic group” refers to and includes aromatic and non-aromatic cyclic radicals 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. Hetero-aromatic cyclic radicals may be used interchangeably with heteroaryl. Preferred hetero-non-aromatic cyclic groups are those containing 3 to 7 ring atoms which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperidino, pyrrolidino, and the like, and cyclic ethers/thio-ethers, such as tetrahydrofuran, tetrahydropyran, tetrahydrothiophene, and the like. Additionally, the heterocyclic group may be optionally substituted.
- The term “aryl” refers to and includes both single-ring aromatic hydrocarbyl groups and polycyclic aromatic ring systems. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is an aromatic hydrocarbyl group, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Especially preferred is an aryl group having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group is optionally substituted.
- The term “heteroaryl” refers to and includes both single-ring aromatic groups and polycyclic aromatic ring systems that include at least one heteroatom. The heteroatoms include, but are not limited to O, S, N, P, B, Si, and Se. In many instances, O, S, or N are the preferred heteroatoms. Hetero-single ring aromatic systems are preferably single rings with 5 or 6 ring atoms, and the ring can have from one to six heteroatoms. The hetero-polycyclic ring systems can have two or more rings in which two atoms are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. The hetero-polycyclic aromatic ring systems can have from one to six heteroatoms per ring of the polycyclic aromatic ring system. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably 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, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof. Additionally, the heteroaryl group is optionally substituted.
- Of the aryl and heteroaryl groups listed above, the groups of triphenylene, naphthalene, anthracene, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, pyrazine, pyrimidine, triazine, and benzimidazole, and the respective aza-analogs of each thereof are of particular interest.
- The terms alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl, as used herein, are independently unsubstituted, or independently substituted, with one or more general substituents.
- In many instances, the general substituents are selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
- In some instances, the preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
- In some instances, the preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, sulfanyl, and combinations thereof.
- In yet other instances, the more preferred general substituents are selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof.
- The term “substituted” refers to a substituent other than H that is bonded to the relevant position, e.g., a carbon. For example, where R1 represents mono-substituted, then one R1 must be other than H. Similarly, where R1 represents di-substituted, then two of R1 must be other than H. Similarly, where R1 is unsubstituted, R1 is hydrogen for all available positions. The maximum number of substitutions possible in a structure (for example, a particular ring or fused ring system) will depend on the number of atoms with available valencies.
- As used herein, “combinations thereof” indicates 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 envision from the applicable list. For example, an alkyl and deuterium can be combined to form a partial or fully deuterated alkyl group; a halogen and alkyl can be combined to form a halogenated alkyl substituent; and a halogen, alkyl, and aryl can be combined to form a halogenated arylalkyl. In one instance, the term substitution includes a combination of two to four of the listed groups. In another instance, the term substitution includes a combination of two to three groups. In yet another instance, the term substitution includes a combination of two groups. Preferred combinations of substituent groups are those that contain up to fifty atoms that are not hydrogen or deuterium, or those which include up to forty atoms that are not hydrogen or deuterium, or those that include up to thirty atoms that are not hydrogen or deuterium. In many instances, a preferred combination of substituent groups will include up to twenty atoms that are not hydrogen or deuterium.
- The “aza” designation in the fragments described herein, i.e. aza-dibenzofuran, aza-dibenzothiophene, etc. means that one or more of the C—H groups in the respective fragment can be replaced by a nitrogen atom, for example, and without any limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, 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. Pat. No. 8,557,400, Patent Pub. No. WO 2006/095951, and U.S. Pat. Application Pub. No. US 2011/0037057, which are hereby incorporated by reference in their entireties, describe the making of deuterium-substituted organometallic complexes. Further reference is made to Ming Yan, et al., Tetrahedron 2015, 71, 1425-30 and Atzrodt et al., Angew. Chem. Int. Ed. (Reviews) 2007, 46, 7744-65, which are incorporated by reference in their entireties, describe the deuteration of the methylene hydrogens in benzyl amines and efficient pathways to replace aromatic ring hydrogens with deuterium, respectively.
- It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.
- According to an aspect of the present disclosure, a compound comprising a first ligand LA having the Formula selected from the group consisting of
- Formula IC, is provided. In Formulae IA, IB, and IC:
- ring B and C are each independently a 5-membered or 6-membered aromatic or heteroaromatic ring;
- RA, RB, RC, and RD each independently represent mono to the maximum possible number of substituents, or no substituent;
- Z1 and Z2 are each independently selected from the group consisting of C and N;
- X1, X2, X3, X4, X5, and X6 are each independently selected from the group consisting of C and N;
- X1, X2, X3, or X4 is C when it forms a direct bond to Z2;
- Y is selected from the group consisting of CRR′, NR′, O, S, and Se;
- R, R′, RA, RB, RC, and RD are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
- any two substituents are optionally joined or fused into a ring;
- the ligand LA is coordinated to a metal M by the dashed lines to form a 5-membered chelate ring;
- wherein M does not form a direct bond to X1 in Formula IB;
wherein M does not form a direct bond to X4 in Formula IC; - the metal M can be coordinated to other ligands; and
- the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
- In some embodiments, ring B can be a ring system comprising two fused rings, such as naphthalene, benzimidazole, etc. In such instances, the maximum substitutions for RB could be hexa- or penta-substitutions, respectively.
- In some embodiments, metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Au, and Cu. In some embodiments, metal M is Ir or Pt.
- In some embodiments, R, R′, RA, RB, RC, and RD are each independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
- In some embodiments, the compound is homoleptic. In some embodiments, the compound is heteroleptic.
- In some embodiments, Y is O.
- In some embodiments, X1 through X6 are each independently C. In some embodiments, X1 through X4 are each independently CR.
- In some embodiments, ring C is a fused benzene ring.
- In some embodiments, ring B is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, benzene imidazole, pyrazole, triazole, pyrrole, oxazole, thiazole, and imidazole derived carbene. In some embodiments, ring A is benezene and ring B is pyridine with Z1 as N. In some embodiments, ring A is pyridine with N coordinated to metal, and ring B is benezene.
- In some embodiments, the first ligand LA is selected from the group consisting of:
- and aza variants thereof; and
- wherein Ra is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alk ynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
- In some embodiments, the first ligand LA is selected from the group consisting of LA1 through LA4560, wherein LA1 through LA4780 have a structure of Formula II:
- wherein R1, R2, X and Y are defined as:
-
Ligand R1 R2 X Y LA1 H H C S LA2 RB1 H C S LA3 RB3 H C S LA4 RB4 H C S LA5 RB7 H C S LA6 RB10 H C S LA7 RA3 H C S LA8 RA34 H C S LA9 H H C O LA10 RB1 H C O LA11 RB3 H C O LA12 RB4 H C O LA13 RB7 H C O LA14 RB10 H C O LA15 RA3 H C O LA16 RA34 H C O LA17 H H C NCH3 LA18 RB1 H C NCH3 LA19 RB3 H C NCH3 LA20 RB4 H C NCH3 LA21 RB7 H C NCH3 LA22 RB10 H C NCH3 LA23 RA3 H C NCH3 LA24 RA34 H C NCH3 LA25 H H C C(CH3)2 LA26 RB1 H C C(CH3)2 LA27 RB3 H C C(CH3)2 LA28 RB4 H C C(CH3)2 LA29 RB7 H C C(CH3)2 LA30 RB10 H C C(CH3)2 LA31 RA3 H C C(CH3)2 LA32 RA34 H C C(CH3)2 LA33 H H C Si(CH3)2 LA34 RB1 H C Si(CH3)2 LA35 RB3 H C Si(CH3)2 LA36 RB4 H C Si(CH3)2 LA37 RB7 H C Si(CH3)2 LA38 RB10 H C Si(CH3)2 LA39 RA3 H C Si(CH3)2 LA40 RA34 H C Si(CH3)2 LA41 H RB1 C S LA42 RB1 RB1 C S LA43 RB3 RB1 C S LA44 RB4 RB1 C S LA45 RB7 RB1 C S LA46 RB10 RB1 C S LA47 RA3 RB1 C S LA48 RA34 RB1 C S LA49 H RB1 C O LA50 RB1 RB1 C O LA51 RB3 RB1 C O LA52 RB4 RB1 C O LA53 RB7 RB1 C O LA54 RB10 RB1 C O LA55 RA3 RB1 C O LA56 RA34 RB1 C O LA57 H RB1 C NCH3 LA58 RB1 RB1 C NCH3 LA59 RB3 RB1 C NCH3 LA60 RB4 RB1 C NCH3 LA61 RB7 RB1 C NCH3 LA62 RB10 RB1 C NCH3 LA63 RA3 RB1 C NCH3 LA64 RA34 RB1 C NCH3 LA65 H RB1 C C(CH3)2 LA66 RB1 RB1 C C(CH3)2 LA67 RB3 RB1 C C(CH3)2 LA68 RB4 RB1 C C(CH3)2 LA69 RB7 RB1 C C(CH3)2 LA70 RB10 RB1 C C(CH3)2 LA71 RA3 RB1 C C(CH3)2 LA72 RA34 RB1 C C(CH3)2 LA73 H RB1 C Si(CH3)2 LA74 RB1 RB1 C Si(CH3)2 LA75 RB3 RB1 C Si(CH3)2 LA76 RB4 RB1 C Si(CH3)2 LA77 RB7 RB1 C Si(CH3)2 LA78 RB10 RB1 C Si(CH3)2 LA79 RA3 RB1 C Si(CH3)2 LA80 RA34 RB1 C Si(CH3)2 LA81 H RB2 C S LA82 RB1 RB2 C S LA83 RB3 RB2 C S LA84 RB4 RB2 C S LA85 RB7 RB2 C S LA86 RB10 RB2 C S LA87 RA3 RB2 C S LA88 RA34 RB2 C S LA89 H RB2 C O LA90 RB1 RB2 C O LA91 RB3 RB2 C O LA92 RB4 RB2 C O LA93 RB7 RB2 C O LA94 RB10 RB2 C O LA95 RA3 RB2 C O LA96 RA34 RB2 C O LA97 H RB2 C NCH3 LA98 RB1 RB2 C NCH3 LA99 RB3 RB2 C NCH3 LA100 RB4 RB2 C NCH3 LA101 RB7 RB2 C NCH3 LA102 RB10 RB2 C NCH3 LA103 RA3 RB2 C NCH3 LA104 RA34 RB2 C NCH3 LA105 H RB2 C C(CH3)2 LA106 RB1 RB2 C C(CH3)2 LA107 RB3 RB2 C C(CH3)2 LA108 RB4 RB2 C C(CH3)2 LA109 RB7 RB2 C C(CH3)2 LA110 RB10 RB2 C C(CH3)2 LA111 RA3 RB2 C C(CH3)2 LA112 RA34 RB2 C C(CH3)2 LA113 H RB2 C Si(CH3)2 LA114 RB1 RB2 C Si(CH3)2 LA115 RB3 RB2 C Si(CH3)2 LA116 RB4 RB2 C Si(CH3)2 LA117 RB7 RB2 C Si(CH3)2 LA118 RB10 RB2 C Si(CH3)2 LA119 RA3 RB2 C Si(CH3)2 LA120 RA34 RB2 C Si(CH3)2 LA121 H H N S LA122 RB1 H N S LA123 RB3 H N S LA124 RB4 H N S LA125 RB7 H N S LA126 RB10 H N S LA127 RA3 H N S LA128 RA34 H N S LA129 H H N O LA130 RB1 H N O LA131 RB3 H N O LA132 RB4 H N O LA133 RB7 H N O LA134 RB10 H N O LA135 RA3 H N O LA136 RA34 H N O LA137 H H N NCH3 LA138 RB1 H N NCH3 LA139 RB3 H N NCH3 LA140 RB4 H N NCH3 LA141 RB7 H N NCH3 LA142 RB10 H N NCH3 LA143 RA3 H N NCH3 LA144 RA34 H N NCH3 LA145 H H N C(CH3)2 LA146 RB1 H N C(CH3)2 LA147 RB3 H N C(CH3)2 LA148 RB4 H N C(CH3)2 LA149 RB7 H N C(CH3)2 LA150 RB10 H N C(CH3)2 LA151 RA3 H N C(CH3)2 LA152 RA34 H N C(CH3)2 LA153 H H N Si(CH3)2 LA154 RB1 H N Si(CH3)2 LA155 RB3 H N Si(CH3)2 LA156 RB4 H N Si(CH3)2 LA157 RB7 H N Si(CH3)2 LA158 RB10 H N Si(CH3)2 LA159 RA3 H N Si(CH3)2 LA160 RA34 H N Si(CH3)2 LA161 H RB1 N S LA162 RB1 RB1 N S LA163 RB3 RB1 N S LA164 RB4 RB1 N S LA165 RB7 RB1 N S LA166 RB10 RB1 N S LA167 RA3 RB1 N S LA168 RA34 RB1 N S LA169 H RB1 N O LA170 RB1 RB1 N O LA171 RB3 RB1 N O LA172 RB4 RB1 N O LA173 RB7 RB1 N O LA174 RB10 RB1 N O LA175 RA3 RB1 N O LA176 RA34 RB1 N O LA177 H RB1 N NCH3 LA178 RB1 RB1 N NCH3 LA179 RB3 RB1 N NCH3 LA180 RB4 RB1 N NCH3 LA181 RB7 RB1 N NCH3 LA182 RB10 RB1 N NCH3 LA183 RA3 RB1 N NCH3 LA184 RA34 RB1 N NCH3 LA185 H RB1 N C(CH3)2 LA186 RB1 RB1 N C(CH3)2 LA187 RB3 RB1 N C(CH3)2 LA188 RB4 RB1 N C(CH3)2 LA189 RB7 RB1 N C(CH3)2 LA190 RB10 RB1 N C(CH3)2 LA191 RA3 RB1 N C(CH3)2 LA192 RA34 RB1 N C(CH3)2 LA193 H RB1 N Si(CH3)2 LA194 RB1 RB1 N Si(CH3)2 LA195 RB3 RB1 N Si(CH3)2 LA196 RB4 RB1 N Si(CH3)2 LA197 RB7 RB1 N Si(CH3)2 LA198 RB10 RB1 N Si(CH3)2 LA199 RA3 RB1 N Si(CH3)2 LA200 RA34 RB1 N Si(CH3)2 LA201 H RB2 N S LA202 RB1 RB2 N S LA203 RB3 RB2 N S LA204 RB4 RB2 N S LA205 RB7 RB2 N S LA206 RB10 RB2 N S LA207 RA3 RB2 N S LA208 RA34 RB2 N S LA209 H RB2 N O LA210 RB1 RB2 N O LA211 RB3 RB2 N O LA212 RB4 RB2 N O LA213 RB7 RB2 N O LA214 RB10 RB2 N O LA215 RA3 RB2 N O LA216 RA34 RB2 N O LA217 H RB2 N NCH3 LA218 RB1 RB2 N NCH3 LA219 RB3 RB2 N NCH3 LA220 RB4 RB2 N NCH3 LA221 RB7 RB2 N NCH3 LA222 RB10 RB2 N NCH3 LA223 RA3 RB2 N NCH3 LA224 RA34 RB2 N NCH3 LA225 H RB2 N C(CH3)2 LA226 RB1 RB2 N C(CH3)2 LA227 RB3 RB2 N C(CH3)2 LA228 RB4 RB2 N C(CH3)2 LA229 RB7 RB2 N C(CH3)2 LA230 RB10 RB2 N C(CH3)2 LA231 RA3 RB2 N C(CH3)2 LA232 RA34 RB2 N C(CH3)2 LA233 H RB2 N Si(CH3)2 LA234 RB1 RB2 N Si(CH3)2 LA235 RB3 RB2 N Si(CH3)2 LA236 RB4 RB2 N Si(CH3)2 LA237 RB7 RB2 N Si(CH3)2 LA238 RB10 RB2 N Si(CH3)2 LA239 RA3 RB2 N Si(CH3)2 LA240 RA34 RB2 N Si(CH3)2
wherein LA241 through LA360 have a structure of Formula III: - wherein R2, R3 and Y are defined as provided below:
-
Ligand R2 R3 Y LA241 H H S LA242 H RB1 S LA243 H RB2 S LA244 H RB3 S LA245 H RB4 S LA246 H RB5 S LA247 H RA34 S LA248 H RA52 S LA249 H H O LA250 H RB1 O LA251 H RB2 O LA252 H RB3 O LA253 H RB4 O LA254 H RB5 O LA255 H RA34 O LA256 H RA52 O LA257 H H NCH3 LA258 H RB1 NCH3 LA259 H RB2 NCH3 LA260 H RB3 NCH3 LA261 H RB4 NCH3 LA262 H RB5 NCH3 LA263 H RA34 NCH3 LA264 H RA52 NCH3 LA265 H H C(CH3)2 LA266 H RB1 C(CH3)2 LA267 H RB2 C(CH3)2 LA268 H RB3 C(CH3)2 LA269 H RB4 C(CH3)2 LA270 H RB5 C(CH3)2 LA271 H RA34 C(CH3)2 LA272 H RA52 C(CH3)2 LA273 H H Si(CH3)2 LA274 H RB1 Si(CH3)2 LA275 H RB2 Si(CH3)2 LA276 H RB3 Si(CH3)2 LA277 H RB4 Si(CH3)2 LA278 H RB5 Si(CH3)2 LA279 H RA34 Si(CH3)2 LA280 H RA52 Si(CH3)2 LA281 RB1 H S LA282 RB1 RB1 S LA283 RB1 RB2 S LA284 RB1 RB3 S LA285 RB1 RB4 S LA286 RB1 RB5 S LA287 RB1 RA34 S LA288 RB1 RA52 S LA289 RB1 H O LA290 RB1 RB1 O LA291 RB1 RB2 O LA292 RB1 RB3 O LA293 RB1 RB4 O LA294 RB1 RB5 O LA295 RB1 RA34 O LA296 RB1 RA52 O LA297 RB1 H NCH3 LA298 RB1 RB1 NCH3 LA299 RB1 RB2 NCH3 LA300 RB1 RB3 NCH3 LA301 RB1 RB4 NCH3 LA302 RB1 RB5 NCH3 LA303 RB1 RA34 NCH3 LA304 RB1 RA52 NCH3 LA305 RB1 H C(CH3)2 LA306 RB1 RB1 C(CH3)2 LA307 RB1 RB2 C(CH3)2 LA308 RB1 RB3 C(CH3)2 LA309 RB1 RB4 C(CH3)2 LA310 RB1 RB5 C(CH3)2 LA311 RB1 RA34 C(CH3)2 LA312 RB1 RA52 C(CH3)2 LA313 RB1 H Si(CH3)2 LA314 RB1 RB1 Si(CH3)2 LA315 RB1 RB2 Si(CH3)2 LA316 RB1 RB3 Si(CH3)2 LA317 RB1 RB4 Si(CH3)2 LA318 RB1 RB5 Si(CH3)2 LA319 RB1 RA34 Si(CH3)2 LA320 RB1 RA52 Si(CH3)2 LA321 RB2 H S LA322 RB2 RB1 S LA323 RB2 RB2 S LA324 RB2 RB3 S LA325 RB2 RB4 S LA326 RB2 RB5 S LA327 RB2 RA34 S LA328 RB2 RA52 S LA329 RB2 H O LA330 RB2 RB1 O LA331 RB2 RB2 O LA332 RB2 RB3 O LA333 RB2 RB4 O LA334 RB2 RB5 O LA335 RB2 RA34 O LA336 RB2 RA52 O LA337 RB2 H NCH3 LA338 RB2 RB1 NCH3 LA339 RB2 RB2 NCH3 LA340 RB2 RB3 NCH3 LA341 RB2 RB4 NCH3 LA342 RB2 RB5 NCH3 LA343 RB2 RA34 NCH3 LA344 RB2 RA52 NCH3 LA345 RB2 H C(CH3)2 LA346 RB2 RB1 C(CH3)2 LA347 RB2 RB2 C(CH3)2 LA348 RB2 RB3 C(CH3)2 LA349 RB2 RB4 C(CH3)2 LA350 RB2 RB5 C(CH3)2 LA351 RB2 RA34 C(CH3)2 LA352 RB2 RA52 C(CH3)2 LA353 RB2 H Si(CH3)2 LA354 RB2 RB1 Si(CH3)2 LA355 RB2 RB2 Si(CH3)2 LA356 RB2 RB3 Si(CH3)2 LA357 RB2 RB4 Si(CH3)2 LA358 RB2 RB5 Si(CH3)2 LA359 RB2 RA34 Si(CH3)2 LA360 RB2 RA52 Si(CH3)2
wherien LA361 through LA456 have a structure of Formula IV, - wherein R2, R4, Y, and X are defined as provided below:
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Ligand R2 R4 Y Z LA361 H H S S LA362 H RB1 S S LA363 H RB3 S S LA364 H RB4 S S LA365 H RB7 S S LA366 H RB10 S S LA367 H RA3 S S LA368 H RA34 S S LA369 H H S O LA370 H RB1 S O LA371 H RB3 S O LA372 H RB4 S O LA373 H RB7 S O LA374 H RB10 S O LA375 H RA3 S O LA376 H RA34 S O LA377 H H S NCH3 LA378 H RB1 S NCH3 LA379 H RB3 S NCH3 LA380 H RB4 S NCH3 LA381 H RB7 S NCH3 LA382 H RB10 S NCH3 LA383 H RA3 S NCH3 LA384 H RA34 S NCH3 LA385 H H O S LA386 H RB1 O S LA387 H RB3 O S LA388 H RB4 O S LA389 H RB7 O S LA390 H RB10 O S LA391 H RA3 O S LA392 H RA34 O S LA393 H H O O LA394 H RB1 O O LA395 H RB3 O O LA396 H RB4 O O LA397 H RB7 O O LA398 H RB10 O O LA399 H RA3 O O LA400 H RA34 O O LA401 H H O NCH3 LA402 H RB1 O NCH3 LA403 H RB3 O NCH3 LA404 H RB4 O NCH3 LA405 H RB7 O NCH3 LA406 H RB10 O NCH3 LA407 H RA3 O NCH3 LA408 H RA34 O NCH3 LA409 RB1 H S S LA410 RB1 RB1 S S LA411 RB1 RB3 S S LA412 RB1 RB4 S S LA413 RB1 RB7 S S LA414 RB1 RB10 S S LA415 RB1 RA3 S S LA416 RB1 RA34 S S LA417 RB1 H S O LA418 RB1 RB1 S O LA419 RB1 RB3 S O LA420 RB1 RB4 S O LA421 RB1 RB7 S O LA422 RB1 RB10 S O LA423 RB1 RA3 S O LA424 RB1 RA34 S O LA425 RB1 H S NCH3 LA426 RB1 RB1 S NCH3 LA427 RB1 RB3 S NCH3 LA428 RB1 RB4 S NCH3 LA429 RB1 RB7 S NCH3 LA430 RB1 RB10 S NCH3 LA431 RB1 RA3 S NCH3 LA432 RB1 RA34 S NCH3 LA433 RB1 H O S LA434 RB1 RB1 O S LA435 RB1 RB3 O S LA436 RB1 RB4 O S LA437 RB1 RB7 O S LA438 RB1 RB10 O S LA439 RB1 RA3 O S LA440 RB1 RA34 O S LA441 RB1 H O O LA442 RB1 RB1 O O LA443 RB1 RB3 O O LA444 RB1 RB4 O O LA445 RB1 RB7 O O LA446 RB1 RB10 O O LA447 RB1 RA3 O O LA448 RB1 RA34 O O LA449 RB1 H O NCH3 LA450 RB1 RB1 O NCH3 LA451 RB1 RB3 O NCH3 LA452 RB1 RB4 O NCH3 LA453 RB1 RB7 O NCH3 LA454 RB1 RB10 O NCH3 LA455 RB1 RA3 O NCH3 LA456 RB1 RA34 O NCH3
wherein LA457 through LA696 have a structure of Formula V: - wherein R1, R2, X, and Y are defined as provided below:
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Ligand R1 R2 X Y LA457 H H C S LA458 RB1 H C S LA459 RB3 H C S LA460 RB4 H C S LA461 RB7 H C S LA462 RB10 H C S LA463 RA3 H C S LA464 RA34 H C S LA465 H H C O LA466 RB1 H C O LA467 RB3 H C O LA468 RB4 H C O LA469 RB7 H C O LA470 RB10 H C O LA471 RA3 H C O LA472 RA34 H C O LA473 H H C NCH3 LA474 RB1 H C NCH3 LA475 RB3 H C NCH3 LA476 RB4 H C NCH3 LA477 RB7 H C NCH3 LA478 RB10 H C NCH3 LA479 RA3 H C NCH3 LA480 RA34 H C NCH3 LA481 H H C C(CH3)2 LA482 RB1 H C C(CH3)2 LA483 RB3 H C C(CH3)2 LA484 RB4 H C C(CH3)2 LA485 RB7 H C C(CH3)2 LA486 RB10 H C C(CH3)2 LA487 RA3 H C C(CH3)2 LA488 RA34 H C C(CH3)2 LA489 H H C Si(CH3)2 LA490 RB1 H C Si(CH3)2 LA491 RB3 H C Si(CH3)2 LA492 RB4 H C Si(CH3)2 LA493 RB7 H C Si(CH3)2 LA494 RB10 H C Si(CH3)2 LA495 RA3 H C Si(CH3)2 LA496 RA34 H C Si(CH3)2 LA497 H RB1 C S LA498 RB1 RB1 C S LA499 RB3 RB1 C S LA500 RB4 RB1 C S LA501 RB7 RB1 C S LA502 RB10 RB1 C S LA503 RA3 RB1 C S LA504 RA34 RB1 C S LA505 H RB1 C O LA506 RB1 RB1 C O LA507 RB3 RB1 C O LA508 RB4 RB1 C O LA509 RB7 RB1 C O LA510 RB10 RB1 C O LA511 RA3 RB1 C O LA512 RA34 RB1 C O LA513 H RB1 C NCH3 LA514 RB1 RB1 C NCH3 LA515 RB3 RB1 C NCH3 LA516 RB4 RB1 C NCH3 LA517 RB7 RB1 C NCH3 LA518 RB10 RB1 C NCH3 LA519 RA3 RB1 C NCH3 LA520 RA34 RB1 C NCH3 LA521 H RB1 C C(CH3)2 LA522 RB1 RB1 C C(CH3)2 LA523 RB3 RB1 C C(CH3)2 LA524 RB4 RB1 C C(CH3)2 LA525 RB7 RB1 C C(CH3)2 LA526 RB10 RB1 C C(CH3)2 LA527 RA3 RB1 C C(CH3)2 LA528 RA34 RB1 C C(CH3)2 LA529 H RB1 C Si(CH3)2 LA530 RB1 RB1 C Si(CH3)2 LA531 RB3 RB1 C Si(CH3)2 LA532 RB4 RB1 C Si(CH3)2 LA533 RB7 RB1 C Si(CH3)2 LA534 RB10 RB1 C Si(CH3)2 LA535 RA3 RB1 C Si(CH3)2 LA536 RA34 RB1 C Si(CH3)2 LA537 H RB2 C S LA538 RB1 RB2 C S LA539 RB3 RB2 C S LA540 RB4 RB2 C S LA541 RB7 RB2 C S LA542 RB10 RB2 C S LA543 RA3 RB2 C S LA544 RA34 RB2 C S LA545 H RB2 C O LA546 RB1 RB2 C O LA547 RB3 RB2 C O LA548 RB4 RB2 C O LA549 RB7 RB2 C O LA550 RB10 RB2 C O LA551 RA3 RB2 C O LA552 RA34 RB2 C O LA553 H RB2 C NCH3 LA554 RB1 RB2 C NCH3 LA555 RB3 RB2 C NCH3 LA556 RB4 RB2 C NCH3 LA557 RB7 RB2 C NCH3 LA558 RB10 RB2 C NCH3 LA559 RA3 RB2 C NCH3 LA560 RA34 RB2 C NCH3 LA561 H RB2 C C(CH3)2 LA562 RB1 RB2 C C(CH3)2 LA563 RB3 RB2 C C(CH3)2 LA564 RB4 RB2 C C(CH3)2 LA565 RB7 RB2 C C(CH3)2 LA566 RB10 RB2 C C(CH3)2 LA567 RA3 RB2 C C(CH3)2 LA568 RA34 RB2 C C(CH3)2 LA569 H RB2 C Si(CH3)2 LA570 RB1 RB2 C Si(CH3)2 LA571 RB3 RB2 C Si(CH3)2 LA572 RB4 RB2 C Si(CH3)2 LA573 RB7 RB2 C Si(CH3)2 LA574 RB10 RB2 C Si(CH3)2 LA575 RA3 RB2 C Si(CH3)2 LA576 RA34 RB2 C Si(CH3)2 LA577 H H N S LA578 RB1 H N S LA579 RB3 H N S LA580 RB4 H N S LA581 RB7 H N S LA582 RB10 H N S LA583 RA3 H N S LA584 RA34 H N S LA585 H H N O LA586 RB1 H N O LA587 RB3 H N O LA588 RB4 H N O LA589 RB7 H N O LA590 RB10 H N O LA591 RA3 H N O LA592 RA34 H N O LA593 H H N NCH3 LA594 RB1 H N NCH3 LA595 RB3 H N NCH3 LA596 RB4 H N NCH3 LA597 RB7 H N NCH3 LA598 RB10 H N NCH3 LA599 RA3 H N NCH3 LA600 RA34 H N NCH3 LA601 H H N C(CH3)2 LA602 RB1 H N C(CH3)2 LA603 RB3 H N C(CH3)2 LA604 RB4 H N C(CH3)2 LA605 RB7 H N C(CH3)2 LA606 RB10 H N C(CH3)2 LA607 RA3 H N C(CH3)2 LA608 RA34 H N C(CH3)2 LA609 H H N Si(CH3)2 LA610 RB1 H N Si(CH3)2 LA611 RB3 H N Si(CH3)2 LA612 RB4 H N Si(CH3)2 LA613 RB7 H N Si(CH3)2 LA614 RB10 H N Si(CH3)2 LA615 RA3 H N Si(CH3)2 LA616 RA34 H N Si(CH3)2 LA617 H RB1 N S LA618 RB1 RB1 N S LA619 RB3 RB1 N S LA620 RB4 RB1 N S LA621 RB7 RB1 N S LA622 RB10 RB1 N S LA623 RA3 RB1 N S LA624 RA34 RB1 N S LA625 H RB1 N O LA626 RB1 RB1 N O LA627 RB3 RB1 N O LA628 RB4 RB1 N O LA629 RB7 RB1 N O LA630 RB10 RB1 N O LA631 RA3 RB1 N O LA632 RA34 RB1 N O LA633 H RB1 N NCH3 LA634 RB1 RB1 N NCH3 LA635 RB3 RB1 N NCH3 LA636 RB4 RB1 N NCH3 LA637 RB7 RB1 N NCH3 LA638 RB10 RB1 N NCH3 LA639 RA3 RB1 N NCH3 LA640 RA34 RB1 N NCH3 LA641 H RB1 N C(CH3)2 LA642 RB1 RB1 N C(CH3)2 LA643 RB3 RB1 N C(CH3)2 LA644 RB4 RB1 N C(CH3)2 LA645 RB7 RB1 N C(CH3)2 LA646 RB10 RB1 N C(CH3)2 LA647 RA3 RB1 N C(CH3)2 LA648 RA34 RB1 N C(CH3)2 LA649 H RB1 N Si(CH3)2 LA650 RB1 RB1 N Si(CH3)2 LA651 RB3 RB1 N Si(CH3)2 LA652 RB4 RB1 N Si(CH3)2 LA653 RB7 RB1 N Si(CH3)2 LA654 RB10 RB1 N Si(CH3)2 LA655 RA3 RB1 N Si(CH3)2 LA656 RA34 RB1 N Si(CH3)2 LA657 H RB2 N S LA658 RB1 RB2 N S LA659 RB3 RB2 N S LA660 RB4 RB2 N S LA661 RB7 RB2 N S LA662 RB10 RB2 N S LA663 RA3 RB2 N S LA664 RA34 RB2 N S LA665 H RB2 N O LA666 RB1 RB2 N O LA667 RB3 RB2 N O LA668 RB4 RB2 N O LA669 RB7 RB2 N O LA670 RB10 RB2 N O LA671 RA3 RB2 N O LA672 RA34 RB2 N O LA673 H RB2 N NCH3 LA674 RB1 RB2 N NCH3 LA675 RB3 RB2 N NCH3 LA676 RB4 RB2 N NCH3 LA677 RB7 RB2 N NCH3 LA678 RB10 RB2 N NCH3 LA679 RA3 RB2 N NCH3 LA680 RA34 RB2 N NCH3 LA681 H RB2 N C(CH3)2 LA682 RB1 RB2 N C(CH3)2 LA683 RB3 RB2 N C(CH3)2 LA684 RB4 RB2 N C(CH3)2 LA685 RB7 RB2 N C(CH3)2 LA686 RB10 RB2 N C(CH3)2 LA687 RA3 RB2 N C(CH3)2 LA688 RA34 RB2 N C(CH3)2 LA689 H RB2 N Si(CH3)2 LA690 RB1 RB2 N Si(CH3)2 LA691 RB3 RB2 N Si(CH3)2 LA692 RB4 RB2 N Si(CH3)2 LA693 RB7 RB2 N Si(CH3)2 LA694 RB10 RB2 N Si(CH3)2 LA695 RA3 RB2 N Si(CH3)2 LA696 RA34 RB2 N Si(CH3)2
wherein LA697 through LA816 have a structure of Formula VI: - wherein R2, R3, and Y are defined as provided below:
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Ligand R2 R3 Y Ligand R1 R2 R14 LA697 H H S LA757 RB1 RB4 NCH3 LA698 H RB1 S LA758 RB1 RB5 NCH3 LA699 H RB2 S LA759 RB1 RA34 NCH3 LA700 H RB3 S LA760 RB1 RA52 NCH3 LA701 H RB4 S LA761 RB1 H C(CH3)2 LA702 H RB5 S LA762 RB1 RB1 C(CH3)2 LA703 H RA34 S LA763 RB1 RB2 C(CH3)2 LA704 H RA52 S LA764 RB1 RB3 C(CH3)2 LA705 H H O LA765 RB1 RB4 C(CH3)2 LA706 H RB1 O LA766 RB1 RB5 C(CH3)2 LA707 H RB2 O LA767 RB1 RA34 C(CH3)2 LA708 H RB3 O LA768 RB1 RA52 C(CH3)2 LA709 H RB4 O LA769 RB1 H Si(CH3)2 LA710 H RB5 O LA770 RB1 RB1 Si(CH3)2 LA711 H RA34 O LA771 RB1 RB2 Si(CH3)2 LA712 H RA52 O LA772 RB1 RB3 Si(CH3)2 LA713 H H NCH3 LA773 RB1 RB4 Si(CH3)2 LA714 H RB1 NCH3 LA774 RB1 RB5 Si(CH3)2 LA715 H RB2 NCH3 LA775 RB1 RA34 Si(CH3)2 LA716 H RB3 NCH3 LA776 RB1 RA52 Si(CH3)2 LA717 H RB4 NCH3 LA777 RB2 H S LA718 H RB5 NCH3 LA778 RB2 RB1 S LA719 H RA34 NCH3 LA779 RB2 RB2 S LA720 H RA52 NCH3 LA780 RB2 RB3 S LA721 H H C(CH3)2 LA781 RB2 RB4 S LA722 H RB1 C(CH3)2 LA782 RB2 RB5 S LA723 H RB2 C(CH3)2 LA783 RB2 RA34 S LA724 H RB3 C(CH3)2 LA784 RB2 RA52 S LA725 H RB4 C(CH3)2 LA785 RB2 H O LA726 H RB5 C(CH3)2 LA786 RB2 RB1 O LA727 H RA34 C(CH3)2 LA787 RB2 RB2 O LA728 H RA52 C(CH3)2 LA788 RB2 RB3 O LA729 H H Si(CH3)2 LA789 RB2 RB4 O LA730 H RB1 Si(CH3)2 LA790 RB2 RB5 O LA731 H RB2 Si(CH3)2 LA791 RB2 RA34 O LA732 H RB3 Si(CH3)2 LA792 RB2 RA52 O LA733 H RB4 Si(CH3)2 LA793 RB2 H NCH3 LA734 H RB5 Si(CH3)2 LA794 RB2 RB1 NCH3 LA735 H RA34 Si(CH3)2 LA795 RB2 RB2 NCH3 LA736 H RA52 Si(CH3)2 LA796 RB2 RB3 NCH3 LA737 RB1 H S LA797 RB2 RB4 NCH3 LA738 RB1 RB1 S LA798 RB2 RB5 NCH3 LA739 RB1 RB2 S LA799 RB2 RA34 NCH3 LA740 RB1 RB3 S LA800 RB2 RA52 NCH3 LA741 RB1 RB4 S LA801 RB2 H C(CH3)2 LA742 RB1 RB5 S LA802 RB2 RB1 C(CH3)2 LA743 RB1 RA34 S LA803 RB2 RB2 C(CH3)2 LA744 RB1 RA52 S LA804 RB2 RB3 C(CH3)2 LA745 RB1 H O LA805 RB2 RB4 C(CH3)2 LA746 RB1 RB1 O LA806 RB2 RB5 C(CH3)2 LA747 RB1 RB2 O LA807 RB2 RA34 C(CH3)2 LA748 RB1 RB3 O LA808 RB2 RA52 C(CH3)2 LA749 RB1 RB4 O LA809 RB2 H Si(CH3)2 LA750 RB1 RB5 O LA810 RB2 RB1 Si(CH3)2 LA751 RB1 RA34 O LA811 RB2 RB2 Si(CH3)2 LA752 RB1 RA52 O LA812 RB2 RB3 Si(CH3)2 LA753 RB1 H NCH3 LA813 RB2 RB4 Si(CH3)2 LA754 RB1 RB1 NCH3 LA814 RB2 RB5 Si(CH3)2 LA755 RB1 RB2 NCH3 LA815 RB2 RA34 Si(CH3)2 LA756 RB1 RB3 NCH3 LA816 RB2 RA52 Si(CH3)2
wherein LA817 through LA912 have a structure of Formula VII: - wherein R2, R4, and Y are defined as provided below:
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Ligand R2 R4 Y Z LA817 H H S S LA818 H RB1 S S LA819 H RB3 S S LA820 H RB4 S S LA821 H RB7 S S LA822 H RB10 S S LA823 H RA3 S S LA824 H RA34 S S LA825 H H S O LA826 H RB1 S O LA827 H RB3 S O LA828 H RB4 S O LA829 H RB7 S O LA830 H RB10 S O LA831 H RA3 S O LA832 H RA34 S O LA833 H H S NCH3 LA834 H RB1 S NCH3 LA835 H RB3 S NCH3 LA836 H RB4 S NCH3 LA837 H RB7 S NCH3 LA838 H RB10 S NCH3 LA839 H RA3 S NCH3 LA840 H RA34 S NCH3 LA841 H H O S LA842 H RB1 O S LA843 H RB3 O S LA844 H RB4 O S LA845 H RB7 O S LA846 H RB10 O S LA847 H RA3 O S LA848 H RA34 O S LA849 H H O O LA850 H RB1 O O LA851 H RB3 O O LA852 H RB4 O O LA853 H RB7 O O LA854 H RB10 O O LA855 H RA3 O O LA856 H RA34 O O LA857 H H O NCH3 LA858 H RB1 O NCH3 LA859 H RB3 O NCH3 LA860 H RB4 O NCH3 LA861 H RB7 O NCH3 LA862 H RB10 O NCH3 LA863 H RA3 O NCH3 LA864 H RA34 O NCH3 LA865 RB1 H S S LA866 RB1 RB1 S S LA867 RB1 RB3 S S LA868 RB1 RB4 S S LA869 RB1 RB7 S S LA870 RB1 RB10 S S LA871 RB1 RA3 S S LA872 RB1 RA34 S S LA873 RB1 H S O LA874 RB1 RB1 S O LA875 RB1 RB3 S O LA876 RB1 RB4 S O LA877 RB1 RB7 S O LA878 RB1 RB10 S O LA879 RB1 RA3 S O LA880 RB1 RA34 S O LA881 RB1 H S NCH3 LA882 RB1 RB1 S NCH3 LA883 RB1 RB3 S NCH3 LA884 RB1 RB4 S NCH3 LA885 RB1 RB7 S NCH3 LA886 RB1 RB10 S NCH3 LA887 RB1 RA3 S NCH3 LA888 RB1 RA34 S NCH3 LA889 RB1 H O S LA890 RB1 RB1 O S LA891 RB1 RB3 O S LA892 RB1 RB4 O S LA893 RB1 RB7 O S LA894 RB1 RB10 O S LA895 RB1 RA3 O S LA896 RB1 RA34 O S LA897 RB1 H O O LA898 RB1 RB1 O O LA899 RB1 RB3 O O LA900 RB1 RB4 O O LA901 RB1 RB7 O O LA902 RB1 RB10 O O LA903 RB1 RA3 O O LA904 RB1 RA34 O O LA905 RB1 H O NCH3 LA906 RB1 RB1 O NCH3 LA907 RB1 RB3 O NCH3 LA908 RB1 RB4 O NCH3 LA909 RB1 RB7 O NCH3 LA910 RB1 RB10 O NCH3 LA911 RB1 RA3 O NCH3 LA912 RB1 RA34 O NCH3
wherein LA913 through LA1152 have a structure of Formula VIII: - wherein R1, R2, and X are defined as provided below:
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Ligand R1 R2 X Y LA913 H H C S LA914 RB1 H C S LA915 RB3 H C S LA916 RB4 H C S LA917 RB7 H C S LA918 RB10 H C S LA919 RA3 H C S LA920 RA34 H C S LA921 H H C O LA922 RB1 H C O LA923 RB3 H C O LA924 RB4 H C O LA925 RB7 H C O LA926 RB10 H C O LA927 RA3 H C O LA928 RA34 H C O LA929 H H C NCH3 LA930 RB1 H C NCH3 LA931 RB3 H C NCH3 LA932 RB4 H C NCH3 LA933 RB7 H C NCH3 LA934 RB10 H C NCH3 LA935 RA3 H C NCH3 LA936 RA34 H C NCH3 LA937 H H C C(CH3)2 LA938 RB1 H C C(CH3)2 LA939 RB3 H C C(CH3)2 LA940 RB4 H C C(CH3)2 LA941 RB7 H C C(CH3)2 LA942 RB10 H C C(CH3)2 LA943 RA3 H C C(CH3)2 LA944 RA34 H C C(CH3)2 LA945 H H C Si(CH3)2 LA946 RB1 H C Si(CH3)2 LA947 RB3 H C Si(CH3)2 LA948 RB4 H C Si(CH3)2 LA949 RB7 H C Si(CH3)2 LA950 RB10 H C Si(CH3)2 LA951 RA3 H C Si(CH3)2 LA952 RA34 H C Si(CH3)2 LA953 H RB1 C S LA954 RB1 RB1 C S LA955 RB3 RB1 C S LA956 RB4 RB1 C S LA957 RB7 RB1 C S LA958 RB10 RB1 C S LA959 RA3 RB1 C S LA960 RA34 RB1 C S LA961 H RB1 C O LA962 RB1 RB1 C O LA963 RB3 RB1 C O LA964 RB4 RB1 C O LA965 RB7 RB1 C O LA966 RB10 RB1 C O LA967 RA3 RB1 C O LA968 RA34 RB1 C O LA969 H RB1 C NCH3 LA970 RB1 RB1 C NCH3 LA971 RB3 RB1 C NCH3 LA972 RB4 RB1 C NCH3 LA973 RB7 RB1 C NCH3 LA974 RB10 RB1 C NCH3 LA975 RA3 RB1 C NCH3 LA976 RA34 RB1 C NCH3 LA977 H RB1 C C(CH3)2 LA978 RB1 RB1 C C(CH3)2 LA979 RB3 RB1 C C(CH3)2 LA980 RB4 RB1 C C(CH3)2 LA981 RB7 RB1 C C(CH3)2 LA982 RB10 RB1 C C(CH3)2 LA983 RA3 RB1 C C(CH3)2 LA984 RA34 RB1 C C(CH3)2 LA985 H RB1 C Si(CH3)2 LA986 RB1 RB1 C Si(CH3)2 LA987 RB3 RB1 C Si(CH3)2 LA988 RB4 RB1 C Si(CH3)2 LA989 RB7 RB1 C Si(CH3)2 LA990 RB10 RB1 C Si(CH3)2 LA991 RA3 RB1 C Si(CH3)2 LA992 RA34 RB1 C Si(CH3)2 LA993 H RB2 C S LA994 RB1 RB2 C S LA995 RB3 RB2 C S LA996 RB4 RB2 C S LA997 RB7 RB2 C S LA998 RB10 RB2 C S LA999 RA3 RB2 C S LA1000 RA34 RB2 C S LA100l H RB2 C O LA1002 RB1 RB2 C O LA1003 RB3 RB2 C O LA1004 RB4 RB2 C O LA1005 RB7 RB2 C O LA1006 RB10 RB2 C O LA1007 RA3 RB2 C O LA1008 RA34 RB2 C O LA1009 H RB2 C NCH3 LA1010 RB1 RB2 C NCH3 LA1011 RB3 RB2 C NCH3 LA1012 RB4 RB2 C NCH3 LA1013 RB7 RB2 C NCH3 LA1014 RB10 RB2 C NCH3 LA1015 RA3 RB2 C NCH3 LA1016 RA34 RB2 C NCH3 LA1017 H RB2 C C(CH3)2 LA1018 RB1 RB2 C C(CH3)2 LA1019 RB3 RB2 C C(CH3)2 LA1020 RB4 RB2 C C(CH3)2 LA1021 RB7 RB2 C C(CH3)2 LA1022 RB10 RB2 C C(CH3)2 LA1023 RA3 RB2 C C(CH3)2 LA1024 RA34 RB2 C C(CH3)2 LA1025 H RB2 C Si(CH3)2 LA1026 RB1 RB2 C Si(CH3)2 LA1027 RB3 RB2 C Si(CH3)2 LA1028 RB4 RB2 C Si(CH3)2 LA1029 RB7 RB2 C Si(CH3)2 LA1030 RB10 RB2 C Si(CH3)2 LA1031 RA3 RB2 C Si(CH3)2 LA1032 RA34 RB2 C Si(CH3)2 LA1033 H H N S LA1034 RB1 H N S LA1035 RB3 H N S LA1036 RB4 H N S LA1037 RB7 H N S LA1038 RB10 H N S LA1039 RA3 H N S LA1040 RA34 H N S LA1041 H H N O LA1042 RB1 H N O LA1043 RB3 H N O LA1044 RB4 H N O LA1045 RB7 H N O LA1046 RB10 H N O LA1047 RA3 H N O LA1048 RA34 H N O LA1049 H H N NCH3 LA1050 RB1 H N NCH3 LA1051 RB3 H N NCH3 LA1052 RB4 H N NCH3 LA1053 RB7 H N NCH3 LA1054 RB10 H N NCH3 LA1055 RA3 H N NCH3 LA1056 RA34 H N NCH3 LA1057 H H N C(CH3)2 LA1058 RB1 H N C(CH3)2 LA1059 RB3 H N C(CH3)2 LA1060 RB4 H N C(CH3)2 LA1061 RB7 H N C(CH3)2 LA1062 RB10 H N C(CH3)2 LA1063 RA3 H N C(CH3)2 LA1064 RA34 H N C(CH3)2 LA1065 H H N Si(CH3)2 LA1066 RB1 H N Si(CH3)2 LA1067 RB3 H N Si(CH3)2 LA1068 RB4 H N Si(CH3)2 LA1069 RB7 H N Si(CH3)2 LA1070 RB10 H N Si(CH3)2 LA1071 RA3 H N Si(CH3)2 LA1072 RA34 H N Si(CH3)2 LA1073 H RB1 N S LA1074 RB1 RB1 N S LA1075 RB3 RB1 N S LA1076 RB4 RB1 N S LA1077 RB7 RB1 N S LA1078 RB10 RB1 N S LA1079 RA3 RB1 N S LA1080 RA34 RB1 N S LA1081 H RB1 N O LA1082 RB1 RB1 N O LA1083 RB3 RB1 N O LA1084 RB4 RB1 N O LA1085 RB7 RB1 N O LA1086 RB10 RB1 N O LA1087 RA3 RB1 N O LA1088 RA34 RB1 N O LA1089 H RB1 N NCH3 LA1090 RB1 RB1 N NCH3 LA1091 RB3 RB1 N NCH3 LA1092 RB4 RB1 N NCH3 LA1093 RB7 RB1 N NCH3 LA1094 RB10 RB1 N NCH3 LA1095 RA3 RB1 N NCH3 LA1096 RA34 RB1 N NCH3 LA1097 H RB1 N C(CH3)2 LA1098 RB1 RB1 N C(CH3)2 LA1099 RB3 RB1 N C(CH3)2 LA1100 RB4 RB1 N C(CH3)2 LA1101 RB7 RB1 N C(CH3)2 LA1102 RB10 RB1 N C(CH3)2 LA1103 RA3 RB1 N C(CH3)2 LA1104 RA34 RB1 N C(CH3)2 LA1105 H RB1 N Si(CH3)2 LA1106 RB1 RB1 N Si(CH3)2 LA1107 RB3 RB1 N Si(CH3)2 LA1108 RB4 RB1 N Si(CH3)2 LA1109 RB7 RB1 N Si(CH3)2 LA1110 RB10 RB1 N Si(CH3)2 LA1111 RA3 RB1 N Si(CH3)2 LA1112 RA34 RB1 N Si(CH3)2 LA1113 H RB2 N S LA1114 RB1 RB2 N S LA1115 RB3 RB2 N S LA1116 RB4 RB2 N S LA1117 RB7 RB2 N S LA1118 RB10 RB2 N S LA1119 RA3 RB2 N S LA1120 RA34 RB2 N S LA1121 H RB2 N O LA1122 RB1 RB2 N O LA1123 RB3 RB2 N O LA1124 RB4 RB2 N O LA1125 RB7 RB2 N O LA1126 RB10 RB2 N O LA1127 RA3 RB2 N O LA1128 RA34 RB2 N O LA1129 H RB2 N NCH3 LA1130 RB1 RB2 N NCH3 LA1131 RB3 RB2 N NCH3 LA1132 RB4 RB2 N NCH3 LA1133 RB7 RB2 N NCH3 LA1134 RB10 RB2 N NCH3 LA1135 RA3 RB2 N NCH3 LA1136 RA34 RB2 N NCH3 LA1137 H RB2 N C(CH3)2 LA1138 RB1 RB2 N C(CH3)2 LA1139 RB3 RB2 N C(CH3)2 LA1140 RB4 RB2 N C(CH3)2 LA1141 RB7 RB2 N C(CH3)2 LA1142 RB10 RB2 N C(CH3)2 LA1143 RA3 RB2 N C(CH3)2 LA1144 RA34 RB2 N C(CH3)2 LA1145 H RB2 N Si(CH3)2 LA1146 RB1 RB2 N Si(CH3)2 LA1147 RB3 RB2 N Si(CH3)2 LA1148 RB4 RB2 N Si(CH3)2 LA1149 RB7 RB2 N Si(CH3)2 LA1150 RB10 RB2 N Si(CH3)2 LA1151 RA3 RB2 N Si(CH3)2 LA1152 RA34 RB2 N Si(CH3)2
wherein LA1153 through LA1272 have a structure of Formula IX: - wherein R2, R3, and Y are defined as provided below:
-
Ligand R2 R3 Y LA1153 H H S LA1154 H RB1 S LA1155 H RB2 S LA1156 H RB3 S LA1157 H RB4 S LA1158 H RB5 S LA1159 H RA34 S LA1160 H RA52 S LA1161 H H O LA1162 H RB1 O LA1163 H RB2 O LA1164 H RB3 O LA1165 H RB4 O LA1166 H RB5 O LA1167 H RA34 O LA1168 H RA52 O LA1169 H H NCH3 LA1170 H RB1 NCH3 LA1171 H RB2 NCH3 LA1172 H RB3 NCH3 LA1173 H RB4 NCH3 LA1174 H RB5 NCH3 LA1175 H RA34 NCH3 LA1176 H RA52 NCH3 LA1177 H H C(CH3)2 LA1178 H RB1 C(CH3)2 LA1179 H RB2 C(CH3)2 LA1180 H RB3 C(CH3)2 LA1181 H RB4 C(CH3)2 LA1182 H RB5 C(CH3)2 LA1183 H RA34 C(CH3)2 LA1184 H RA52 C(CH3)2 LA1185 H H Si(CH3)2 LA1186 H RB1 Si(CH3)2 LA1187 H RB2 Si(CH3)2 LA1188 H RB3 Si(CH3)2 LA1189 H RB4 Si(CH3)2 LA1190 H RB5 Si(CH3)2 LA1191 H RA34 Si(CH3)2 LA1192 H RA52 Si(CH3)2 LA1193 RB1 H S LA1194 RB1 RB1 S LA1195 RB1 RB2 S LA1196 RB1 RB3 S LA1197 RB1 RB4 S LA1198 RB1 RB5 S LA1199 RB1 RA34 S LA1200 RB1 RA52 S LA1201 RB1 H O LA1202 RB1 RB1 O LA1203 RB1 RB2 O LA1204 RB1 RB3 O LA1205 RB1 RB4 O LA1206 RB1 RB5 O LA1207 RB1 RA34 O LA1208 RB1 RA52 O LA1209 RB1 H NCH3 LA1210 RB1 RB1 NCH3 LA1211 RB1 RB2 NCH3 LA1212 RB1 RB3 NCH3 LA1213 RB1 RB4 NCH3 LA1214 RB1 RB5 NCH3 LA1215 RB1 RA34 NCH3 LA1216 RB1 RA52 NCH3 LA1217 RB1 H C(CH3)2 LA1218 RB1 RB1 C(CH3)2 LA1219 RB1 RB2 C(CH3)2 LA1220 RB1 RB3 C(CH3)2 LA1221 RB1 RB4 C(CH3)2 LA1222 RB1 RB5 C(CH3)2 LA1223 RB1 RA34 C(CH3)2 LA1224 RB1 RA52 C(CH3)2 LA1225 RB1 H Si(CH3)2 LA1226 RB1 RB1 Si(CH3)2 LA1227 RB1 RB2 Si(CH3)2 LA1228 RB1 RB3 Si(CH3)2 LA1229 RB1 RB4 Si(CH3)2 LA1230 RB1 RB5 Si(CH3)2 LA1231 RB1 RA34 Si(CH3)2 LA1232 RB1 RA52 Si(CH3)2 LA1233 RB2 H S LA1234 RB2 RB1 S LA1235 RB2 RB2 S LA1236 RB2 RB3 S LA1237 RB2 RB4 S LA1238 RB2 RB5 S LA1239 RB2 RA34 S LA1240 RB2 RA52 S LA1241 RB2 H O LA1242 RB2 RB1 O LA1243 RB2 RB2 O LA1244 RB2 RB3 O LA1245 RB2 RB4 O LA1246 RB2 RB5 O LA1247 RB2 RA34 O LA1248 RB2 RA52 O LA1249 RB2 H NCH3 LA1250 RB2 RB1 NCH3 LA1251 RB2 RB2 NCH3 LA1252 RB2 RB3 NCH3 LA1253 RB2 RB4 NCH3 LA1254 RB2 RB5 NCH3 LA1255 RB2 RA34 NCH3 LA1256 RB2 RA52 NCH3 LA1257 RB2 H C(CH3)2 LA1258 RB2 RB1 C(CH3)2 LA1259 RB2 RB2 C(CH3)2 LA1260 RB2 RB3 C(CH3)2 LA1261 RB2 RB4 C(CH3)2 LA1262 RB2 RB5 C(CH3)2 LA1263 RB2 RA34 C(CH3)2 LA1264 RB2 RA52 C(CH3)2 LA1265 RB2 H Si(CH3)2 LA1266 RB2 RB1 Si(CH3)2 LA1267 RB2 RB2 Si(CH3)2 LA1268 RB2 RB3 Si(CH3)2 LA1269 RB2 RB4 Si(CH3)2 LA1270 RB2 RB5 Si(CH3)2 LA1271 RB2 RA34 Si(CH3)2 LA1272 RB2 RA52 Si(CH3)2
wherein LA1273 through LA1368 have a structure of Formula X: - wherein R2, R4, Y, and Z are defined as provided below:
-
Ligand R2 R4 Y Z LA1273 H H S S LA1274 H RB1 S S LA1275 H RB3 S S LA1276 H RB4 S S LA1277 H RB7 S S LA1278 H RB10 S S LA1279 H RA3 S S LA1280 H RA34 S S LA1281 H H S O LA1282 H RB1 S O LA1283 H RB3 S O LA1284 H RB4 S O LA1285 H RB7 S O LA1286 H RB10 S O LA1287 H RA3 S O LA1288 H RA34 S O LA1289 H H S NCH3 LA1290 H RB1 S NCH3 LA1291 H RB3 S NCH3 LA1292 H RB4 S NCH3 LA1293 H RB7 S NCH3 LA1294 H RB10 S NCH3 LA1295 H RA3 S NCH3 LA1296 H RA34 S NCH3 LA1297 H H O S LA1298 H RB1 O S LA1299 H RB3 O S LA1300 H RB4 O S LA1301 H RB7 O S LA1302 H RB10 O S LA1303 H RA3 O S LA1304 H RA34 O S LA1305 H H O O LA1306 H RB1 O O LA1307 H RB3 O O LA1308 H RB4 O O LA1309 H RB7 O O LA1310 H RB10 O O LA1311 H RA3 O O LA1312 H RA34 O O LA1313 H H O NCH3 LA1314 H RB1 O NCH3 LA1315 H RB3 O NCH3 LA1316 H RB4 O NCH3 LA1317 H RB7 O NCH3 LA1318 H RB10 O NCH3 LA1319 H RA3 O NCH3 LA1320 H RA34 O NCH3 LA1321 RB1 H S S LA1322 RB1 RB1 S S LA1323 RB1 RB3 S S LA1324 RB1 RB4 S S LA1325 RB1 RB7 S S LA1326 RB1 RB10 S S LA1327 RB1 RA3 S S LA1328 RB1 RA34 S S LA1329 RB1 H S O LA1330 RB1 RB1 S O LA1331 RB1 RB3 S O LA1332 RB1 RB4 S O LA1333 RB1 RB7 S O LA1334 RB1 RB10 S O LA1335 RB1 RA3 S O LA1336 RB1 RA34 S O LA1337 RB1 H S NCH3 LA1338 RB1 RB1 S NCH3 LA1339 RB1 RB3 S NCH3 LA1340 RB1 RB4 S NCH3 LA1341 RB1 RB7 S NCH3 LA1342 RB1 RB10 S NCH3 LA1343 RB1 RA3 S NCH3 LA1344 RB1 RA34 S NCH3 LA1345 RB1 H O S LA1346 RB1 RB1 O S LA1347 RB1 RB3 O S LA1348 RB1 RB4 O S LA1349 RB1 RB7 O S LA1350 RB1 RB10 O S LA1351 RB1 RA3 O S LA1352 RB1 RA34 O S LA1353 RB1 H O O LA1354 RB1 RB1 O O LA1355 RB1 RB3 O O LA1356 RB1 RB4 O O LA1357 RB1 RB7 O O LA1358 RB1 RB10 O O LA1359 RB1 RA3 O O LA1360 RB1 RA34 O O LA1361 RB1 H O NCH3 LA1362 RB1 RB1 O NCH3 LA1363 RB1 RB3 O NCH3 LA1364 RB1 RB4 O NCH3 LA1365 RB1 RB7 O NCH3 LA1366 RB1 RB10 O NCH3 LA1367 RB1 RA3 O NCH3 LA1368 RB1 RA34 O NCH3
wherein LA1369 through LA1608 have a structure of Formula XI: - wherein R1, R2, and Y are defined as provided below:
-
Ligand R1 R2 X Y LA1369 H H C S LA1370 RB1 H C S LA1371 RB3 H C S LA1372 RB4 H C S LA1373 RB7 H C S LA1374 RB10 H C S LA1375 RA3 H C S LA1376 RA34 H C S LA1377 H H C O LA1378 RB1 H C O LA1379 RB3 H C O LA1380 RB4 H C O LA1381 RB7 H C O LA1382 RB10 H C O LA1383 RA3 H C O LA1384 RA34 H C O LA1385 H H C NCH3 LA1386 RB1 H C NCH3 LA1387 RB3 H C NCH3 LA1388 RB4 H C NCH3 LA1389 RB7 H C NCH3 LA1390 RB10 H C NCH3 LA1391 RA3 H C NCH3 LA1392 RA34 H C NCH3 LA1393 H H C C(CH3)2 LA1394 RB1 H C C(CH3)2 LA1395 RB3 H C C(CH3)2 LA1396 RB4 H C C(CH3)2 LA1397 RB7 H C C(CH3)2 LA1398 RB10 H C C(CH3)2 LA1399 RA3 H C C(CH3)2 LA1400 RA34 H C C(CH3)2 LA1401 H H C Si(CH3)2 LA1402 RB1 H C Si(CH3)2 LA1403 RB3 H C Si(CH3)2 LA1404 RB4 H C Si(CH3)2 LA1405 RB7 H C Si(CH3)2 LA1406 RB10 H C Si(CH3)2 LA1407 RA3 H C Si(CH3)2 LA1408 RA34 H C Si(CH3)2 LA1409 H RB1 C S LA1410 RB1 RB1 C S LA1411 RB3 RB1 C S LA1412 RB4 RB1 C S LA1413 RB7 RB1 C S LA1414 RB10 RB1 C S LA1415 RA3 RB1 C S LA1416 RA34 RB1 C S LA1417 H RB1 C O LA1418 RB1 RB1 C O LA1419 RB3 RB1 C O LA1420 RB4 RB1 C O LA1421 RB7 RB1 C O LA1422 RB10 RB1 C O LA1423 RA3 RB1 C O LA1424 RA34 RB1 C O LA1425 H RB1 C NCH3 LA1426 RB1 RB1 C NCH3 LA1427 RB3 RB1 C NCH3 LA1428 RB4 RB1 C NCH3 LA1429 RB7 RB1 C NCH3 LA1430 RB10 RB1 C NCH3 LA1431 RA3 RB1 C NCH3 LA1432 RA34 RB1 C NCH3 LA1433 H RB1 C C(CH3)2 LA1434 RB1 RB1 C C(CH3)2 LA1435 RB3 RB1 C C(CH3)2 LA1436 RB4 RB1 C C(CH3)2 LA1437 RB7 RB1 C C(CH3)2 LA1438 RB10 RB1 C C(CH3)2 LA1439 RA3 RB1 C C(CH3)2 LA1440 RA34 RB1 C C(CH3)2 LA1441 H RB1 C Si(CH3)2 LA1442 RB1 RB1 C Si(CH3)2 LA1443 RB3 RB1 C Si(CH3)2 LA1444 RB4 RB1 C Si(CH3)2 LA1445 RB7 RB1 C Si(CH3)2 LA1446 RB10 RB1 C Si(CH3)2 LA1447 RA3 RB1 C Si(CH3)2 LA1448 RA34 RB1 C Si(CH3)2 LA1449 H RB2 C S LA1450 RB1 RB2 C S LA1451 RB3 RB2 C S LA1452 RB4 RB2 C S LA1453 RB7 RB2 C S LA1454 RB10 RB2 C S LA1455 RA3 RB2 C S LA1456 RA34 RB2 C S LA1457 H RB2 C O LA1458 RB1 RB2 C O LA1459 RB3 RB2 C O LA1460 RB4 RB2 C O LA1461 RB7 RB2 C O LA1462 RB10 RB2 C O LA1463 RA3 RB2 C O LA1464 RA34 RB2 C O LA1465 H RB2 C NCH3 LA1466 RB1 RB2 C NCH3 LA1467 RB3 RB2 C NCH3 LA1468 RB4 RB2 C NCH3 LA1469 RB7 RB2 C NCH3 LA1470 RB10 RB2 C NCH3 LA1471 RA3 RB2 C NCH3 LA1472 RA34 RB2 C NCH3 LA1473 H RB2 C C(CH3)2 LA1474 RB1 RB2 C C(CH3)2 LA1475 RB3 RB2 C C(CH3)2 LA1476 RB4 RB2 C C(CH3)2 LA1477 RB7 RB2 C C(CH3)2 LA1478 RB10 RB2 C C(CH3)2 LA1479 RA3 RB2 C C(CH3)2 LA1480 RA34 RB2 C C(CH3)2 LA1481 H RB2 C Si(CH3)2 LA1482 RB1 RB2 C Si(CH3)2 LA1483 RB3 RB2 C Si(CH3)2 LA1484 RB4 RB2 C Si(CH3)2 LA1485 RB7 RB2 C Si(CH3)2 LA1486 RB10 RB2 C Si(CH3)2 LA1487 RA3 RB2 C Si(CH3)2 LA1488 RA34 RB2 C Si(CH3)2 LA1489 H H N S LA1490 RB1 H N S LA1491 RB3 H N S LA1492 RB4 H N S LA1493 RB7 H N S LA1494 RB10 H N S LA1495 RA3 H N S LA1496 RA34 H N S LA1497 H H N O LA1498 RB1 H N O LA1499 RB3 H N O LA1500 RB4 H N O LA1501 RB7 H N O LA1502 RB10 H N O LA1503 RA3 H N O LA1504 RA34 H N O LA1505 H H N NCH3 LA1506 RB1 H N NCH3 LA1507 RB3 H N NCH3 LA1508 RB4 H N NCH3 LA1509 RB7 H N NCH3 LA1510 RB10 H N NCH3 LA1511 RA3 H N NCH3 LA1512 RA34 H N NCH3 LA1513 H H N C(CH3)2 LA1514 RB1 H N C(CH3)2 LA1515 RB3 H N C(CH3)2 LA1516 RB4 H N C(CH3)2 LA1517 RB7 H N C(CH3)2 LA1518 RB10 H N C(CH3)2 LA1519 RA3 H N C(CH3)2 LA1520 RA34 H N C(CH3)2 LA1521 H H N Si(CH3)2 LA1522 RB1 H N Si(CH3)2 LA1523 RB3 H N Si(CH3)2 LA1524 RB4 H N Si(CH3)2 LA1525 RB7 H N Si(CH3)2 LA1526 RB10 H N Si(CH3)2 LA1527 RA3 H N Si(CH3)2 LA1528 RA34 H N Si(CH3)2 LA1529 H RB1 N S LA1530 RB1 RB1 N S LA1531 RB3 RB1 N S LA1532 RB4 RB1 N S LA1533 RB7 RB1 N S LA1534 RB10 RB1 N S LA1535 RA3 RB1 N S LA1536 RA34 RB1 N S LA1537 H RB1 N O LA1538 RB1 RB1 N O LA1539 RB3 RB1 N O LA1540 RB4 RB1 N O LA1541 RB7 RB1 N O LA1542 RB10 RB1 N O LA1543 RA3 RB1 N O LA1544 RA34 RB1 N O LA1545 H RB1 N NCH3 LA1546 RB1 RB1 N NCH3 LA1547 RB3 RB1 N NCH3 LA1548 RB4 RB1 N NCH3 LA1549 RB7 RB1 N NCH3 LA1550 RB10 RB1 N NCH3 LA1551 RA3 RB1 N NCH3 LA1552 RA34 RB1 N NCH3 LA1553 H RB1 N C(CH3)2 LA1554 RB1 RB1 N C(CH3)2 LA1555 RB3 RB1 N C(CH3)2 LA1556 RB4 RB1 N C(CH3)2 LA1557 RB7 RB1 N C(CH3)2 LA1558 RB10 RB1 N C(CH3)2 LA1559 RA3 RB1 N C(CH3)2 LA1560 RA34 RB1 N C(CH3)2 LA1561 H RB1 N Si(CH3)2 LA1562 RB1 RB1 N Si(CH3)2 LA1563 RB3 RB1 N Si(CH3)2 LA1564 RB4 RB1 N Si(CH3)2 LA1565 RB7 RB1 N Si(CH3)2 LA1566 RB10 RB1 N Si(CH3)2 LA1567 RA3 RB1 N Si(CH3)2 LA1568 RA34 RB1 N Si(CH3)2 LA1569 H RB2 N S LA1570 RB1 RB2 N S LA1571 RB3 RB2 N S LA1572 RB4 RB2 N S LA1573 RB7 RB2 N S LA1574 RB10 RB2 N S LA1575 RA3 RB2 N S LA1576 RA34 RB2 N S LA1577 H RB2 N O LA1578 RB1 RB2 N O LA1579 RB3 RB2 N O LA1580 RB4 RB2 N O LA1581 RB7 RB2 N O LA1582 RB10 RB2 N O LA1583 RA3 RB2 N O LA1584 RA34 RB2 N O LA1585 H RB2 N NCH3 LA1586 RB1 RB2 N NCH3 LA1587 RB3 RB2 N NCH3 LA1588 RB4 RB2 N NCH3 LA1589 RB7 RB2 N NCH3 LA1590 RB10 RB2 N NCH3 LA1591 RA3 RB2 N NCH3 LA1592 RA34 RB2 N NCH3 LA1593 H RB2 N C(CH3)2 LA1594 RB1 RB2 N C(CH3)2 LA1595 RB3 RB2 N C(CH3)2 LA1596 RB4 RB2 N C(CH3)2 LA1597 RB7 RB2 N C(CH3)2 LA1598 RB10 RB2 N C(CH3)2 LA1599 RA3 RB2 N C(CH3)2 LA1600 RA34 RB2 N C(CH3)2 LA1601 H RB2 N Si(CH3)2 LA1602 RB1 RB2 N Si(CH3)2 LA1603 RB3 RB2 N Si(CH3)2 LA1604 RB4 RB2 N Si(CH3)2 LA1605 RB7 RB2 N Si(CH3)2 LA1606 RB10 RB2 N Si(CH3)2 LA1607 RA3 RB2 N Si(CH3)2 LA1608 RA34 RB2 N Si(CH3)2
wherein LA1609 through LA1728 have a structure of Formula XII: - wherein R2, R3, and Y are defined as provided below:
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Ligand R2 R3 Y LA1609 H H S LA1610 H RB1 S LA1611 H RB2 S LA1612 H RB3 S LA1613 H RB4 S LA1614 H RB5 S LA1615 H RA34 S LA1616 H RA52 S LA1617 H H O LA1618 H RB1 O LA1619 H RB2 O LA1620 H RB3 O LA1621 H RB4 O LA1622 H RB5 O LA1623 H RA34 O LA1624 H RA52 O LA1625 H H NCH3 LA1626 H RB1 NCH3 LA1627 H RB2 NCH3 LA1628 H RB3 NCH3 LA1629 H RB4 NCH3 LA1630 H RB5 NCH3 LA1631 H RA34 NCH3 LA1632 H RA52 NCH3 LA1633 H H C(CH3)2 LA1634 H RB1 C(CH3)2 LA1635 H RB2 C(CH3)2 LA1636 H RB3 C(CH3)2 LA1637 H RB4 C(CH3)2 LA1638 H RB5 C(CH3)2 LA1639 H RA34 C(CH3)2 LA1640 H RA52 C(CH3)2 LA1641 H H Si(CH3)2 LA1642 H RB1 Si(CH3)2 LA1643 H RB2 Si(CH3)2 LA1644 H RB3 Si(CH3)2 LA1645 H RB4 Si(CH3)2 LA1646 H RB5 Si(CH3)2 LA1647 H RA34 Si(CH3)2 LA1648 H RA52 Si(CH3)2 LA1649 RB1 H S LA1650 RB1 RB1 S LA1651 RB1 RB2 S LA1652 RB1 RB3 S LA1653 RB1 RB4 S LA1654 RB1 RB5 S LA1655 RB1 RA34 S LA1656 RB1 RA52 S LA1657 RB1 H O LA1658 RB1 RB1 O LA1659 RB1 RB2 O LA1660 RB1 RB3 O LA1661 RB1 RB4 O LA1662 RB1 RB5 O LA1663 RB1 RA34 O LA1664 RB1 RA52 O LA1665 RB1 H NCH3 LA1666 RB1 RB1 NCH3 LA1667 RB1 RB2 NCH3 LA1668 RB1 RB3 NCH3 LA1669 RB1 RB4 NCH3 LA1670 RB1 RB5 NCH3 LA1671 RB1 RA34 NCH3 LA1672 RB1 RA52 NCH3 LA1673 RB1 H C(CH3)2 LA1674 RB1 RB1 C(CH3)2 LA1675 RB1 RB2 C(CH3)2 LA1676 RB1 RB3 C(CH3)2 LA1677 RB1 RB4 C(CH3)2 LA1678 RB1 RB5 C(CH3)2 LA1679 RB1 RA34 C(CH3)2 LA1680 RB1 RA52 C(CH3)2 LA1681 RB1 H Si(CH3)2 LA1682 RB1 RB1 Si(CH3)2 LA1683 RB1 RB2 Si(CH3)2 LA1684 RB1 RB3 Si(CH3)2 LA1685 RB1 RB4 Si(CH3)2 LA1686 RB1 RB5 Si(CH3)2 LA1687 RB1 RA34 Si(CH3)2 LA1688 RB1 RA52 Si(CH3)2 LA1689 RB2 H S LA1690 RB2 RB1 S LA1691 RB2 RB2 S LA1692 RB2 RB3 S LA1693 RB2 RB4 S LA1694 RB2 RB5 S LA1695 RB2 RA34 S LA1696 RB2 RA52 S LA1697 RB2 H O LA1698 RB2 RB1 O LA1699 RB2 RB2 O LA1700 RB2 RB3 O LA1701 RB2 RB4 O LA1702 RB2 RB5 O LA1703 RB2 RA34 O LA1704 RB2 RA52 O LA1705 RB2 H NCH3 LA1706 RB2 RB1 NCH3 LA1707 RB2 RB2 NCH3 LA1708 RB2 RB3 NCH3 LA1709 RB2 RB4 NCH3 LA1710 RB2 RB5 NCH3 LA1711 RB2 RA34 NCH3 LA1712 RB2 RA52 NCH3 LA1713 RB2 H C(CH3)2 LA1714 RB2 RB1 C(CH3)2 LA1715 RB2 RB2 C(CH3)2 LA1716 RB2 RB3 C(CH3)2 LA1717 RB2 RB4 C(CH3)2 LA1718 RB2 RB5 C(CH3)2 LA1719 RB2 RA34 C(CH3)2 LA1720 RB2 RA52 C(CH3)2 LA1721 RB2 H Si(CH3)2 LA1722 RB2 RB1 Si(CH3)2 LA1723 RB2 RB2 Si(CH3)2 LA1724 RB2 RB3 Si(CH3)2 LA1725 RB2 RB4 Si(CH3)2 LA1726 RB2 RB5 Si(CH3)2 LA1727 RB2 RA34 Si(CH3)2 LA1728 RB2 RA52 Si(CH3)2
wherein LA1729 through LA1824 have a structure of Formula XIII: - wherein R2, R4, Y, and Z are defined as provided below:
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Ligand R2 R4 Y Z LA1729 H H S S LA1730 H RB1 S S LA1731 H RB3 S S LA1732 H RB4 S S LA1733 H RB7 S S LA1734 H RB10 S S LA1735 H RA3 S S LA1736 H RA34 S S LA1737 H H S O LA1738 H RB1 S O LA1739 H RB3 S O LA1740 H RB4 S O LA1741 H RB7 S O LA1742 H RB10 S O LA1743 H RA3 S O LA1744 H RA34 S O LA1745 H H S NCH3 LA1746 H RB1 S NCH3 LA1747 H RB3 S NCH3 LA1748 H RB4 S NCH3 LA1749 H RB7 S NCH3 LA1750 H RB10 S NCH3 LA1751 H RA3 S NCH3 LA1752 H RA34 S NCH3 LA1753 H H O S LA1754 H RB1 O S LA1755 H RB3 O S LA1756 H RB4 O S LA1757 H RB7 O S LA1758 H RB10 O S LA1759 H RA3 O S LA1760 H RA34 O S LA1761 H H O O LA1762 H RB1 O O LA1763 H RB3 O O LA1764 H RB4 O O LA1765 H RB7 O O LA1766 H RB10 O O LA1767 H RA3 O O LA1768 H RA34 O O LA1769 H H O NCH3 LA1770 H RB1 O NCH3 LA1771 H RB3 O NCH3 LA1772 H RB4 O NCH3 LA1773 H RB7 O NCH3 LA1774 H RB10 O NCH3 LA1775 H RA3 O NCH3 LA1776 H RA34 O NCH3 LA1777 RB1 H S S LA1778 RB1 RB1 S S LA1779 RB1 RB3 S S LA1780 RB1 RB4 S S LA1781 RB1 RB7 S S LA1782 RB1 RB10 S S LA1783 RB1 RA3 S S LA1784 RB1 RA34 S S LA1785 RB1 H S O LA1786 RB1 RB1 S O LA1787 RB1 RB3 S O LA1788 RB1 RB4 S O LA1789 RB1 RB7 S O LA1790 RB1 RB10 S O LA1791 RB1 RA3 S O LA1792 RB1 RA34 S O LA1793 RB1 H S NCH3 LA1794 RB1 RB1 S NCH3 LA1795 RB1 RB3 S NCH3 LA1796 RB1 RB4 S NCH3 LA1797 RB1 RB7 S NCH3 LA1798 RB1 RB10 S NCH3 LA1799 RB1 RA3 S NCH3 LA1800 RB1 RA34 S NCH3 LA1801 RB1 H O S LA1802 RB1 RB1 O S LA1803 RB1 RB3 O S LA1804 RB1 RB4 O S LA1805 RB1 RB7 O S LA1806 RB1 RB10 O S LA1807 RB1 RA3 O S LA1808 RB1 RA34 O S LA1809 RB1 H O O LA1810 RB1 RB1 O O LA1811 RB1 RB3 O O LA1812 RB1 RB4 O O LA1813 RB1 RB7 O O LA1814 RB1 RB10 O O LA1815 RB1 RA3 O O LA1816 RB1 RA34 O O LA1817 RB1 H O NCH3 LA1818 RB1 RB1 O NCH3 LA1819 RB1 RB3 O NCH3 LA1820 RB1 RB4 O NCH3 LA1821 RB1 RB7 O NCH3 LA1822 RB1 RB10 O NCH3 LA1823 RB1 RA3 O NCH3 LA1824 RB1 RA34 O NCH3
wherein LA1825 through LA2064 have a structure of Formula XIV: - wherein R1, R5, X, and Y are defined as provided below:
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Ligand R1 R5 X Y LA1825 H H C S LA1826 RB1 H C S LA1827 RB3 H C S LA1828 RB4 H C S LA1829 RB7 H C S LA1830 RB10 H C S LA1831 RA3 H C S LA1832 RA34 H C S LA1833 H H C O LA1834 RB1 H C O LA1835 RB3 H C O LA1836 RB4 H C O LA1837 RB7 H C O LA1838 RB10 H C O LA1839 RA3 H C O LA1840 RA34 H C O LA1841 H H C NCH3 LA1842 RB1 H C NCH3 LA1843 RB3 H C NCH3 LA1844 RB4 H C NCH3 LA1845 RB7 H C NCH3 LA1846 RB10 H C NCH3 LA1847 RA3 H C NCH3 LA1848 RA34 H C NCH3 LA1849 H H C C(CH3)2 LA1850 RB1 H C C(CH3)2 LA1851 RB3 H C C(CH3)2 LA1852 RB4 H C C(CH3)2 LA1853 RB7 H C C(CH3)2 LA1854 RB10 H C C(CH3)2 LA1855 RA3 H C C(CH3)2 LA1856 RA34 H C C(CH3)2 LA1857 H H C Si(CH3)2 LA1858 RB1 H C Si(CH3)2 LA1859 RB3 H C Si(CH3)2 LA1860 RB4 H C Si(CH3)2 LA1861 RB7 H C Si(CH3)2 LA1862 RB10 H C Si(CH3)2 LA1863 RA3 H C Si(CH3)2 LA1864 RA34 H C Si(CH3)2 LA1865 H RB1 C S LA1866 RB1 RB1 C S LA1867 RB3 RB1 C S LA1868 RB4 RB1 C S LA1869 RB7 RB1 C S LA1870 RB10 RB1 C S LA1871 RA3 RB1 C S LA1872 RA34 RB1 C S LA1873 H RB1 C O LA1874 RB1 RB1 C O LA1875 RB3 RB1 C O LA1876 RB4 RB1 C O LA1877 RB7 RB1 C O LA1878 RB10 RB1 C O LA1879 RA3 RB1 C O LA1880 RA34 RB1 C O LA1881 H RB1 C NCH3 LA1882 RB1 RB1 C NCH3 LA1883 RB3 RB1 C NCH3 LA1884 RB4 RB1 C NCH3 LA1885 RB7 RB1 C NCH3 LA1886 RB10 RB1 C NCH3 LA1887 RA3 RB1 C NCH3 LA1888 RA34 RB1 C NCH3 LA1889 H RB1 C C(CH3)2 LA1890 RB1 RB1 C C(CH3)2 LA1891 RB3 RB1 C C(CH3)2 LA1892 RB4 RB1 C C(CH3)2 LA1893 RB7 RB1 C C(CH3)2 LA1894 RB10 RB1 C C(CH3)2 LA1895 RA3 RB1 C C(CH3)2 LA1896 RA34 RB1 C C(CH3)2 LA1897 H RB1 C Si(CH3)2 LA1898 RB1 RB1 C Si(CH3)2 LA1899 RB3 RB1 C Si(CH3)2 LA1900 RB4 RB1 C Si(CH3)2 LA1901 RB7 RB1 C Si(CH3)2 LA1902 RB10 RB1 C Si(CH3)2 LA1903 RA3 RB1 C Si(CH3)2 LA1904 RA34 RB1 C Si(CH3)2 LA1905 H RB6 C S LA1906 RB1 RB6 C S LA1907 RB3 RB6 C S LA1908 RB4 RB6 C S LA1909 RB7 RB6 C S LA1910 RB10 RB6 C S LA1911 RA3 RB6 C S LA1912 RA34 RB6 C S LA1913 H RB6 C O LA1914 RB1 RB6 C O LA1915 RB3 RB6 C O LA1916 RB4 RB6 C O LA1917 RB7 RB6 C O LA1918 RB10 RB6 C O LA1919 RA3 RB6 C O LA1920 RA34 RB6 C O LA1921 H RB6 C NCH3 LA1922 RB1 RB6 C NCH3 LA1923 RB3 RB6 C NCH3 LA1924 RB4 RB6 C NCH3 LA1925 RB7 RB6 C NCH3 LA1926 RB10 RB6 C NCH3 LA1927 RA3 RB6 C NCH3 LA1928 RA34 RB6 C NCH3 LA1929 H RB6 C C(CH3)2 LA1930 RB1 RB6 C C(CH3)2 LA1931 RB3 RB6 C C(CH3)2 LA1932 RB4 RB6 C C(CH3)2 LA1933 RB7 RB6 C C(CH3)2 LA1934 RB10 RB6 C C(CH3)2 LA1935 RA3 RB6 C C(CH3)2 LA1936 RA34 RB6 C C(CH3)2 LA1937 H RB6 C Si(CH3)2 LA1938 RB1 RB6 C Si(CH3)2 LA1939 RB3 RB6 C Si(CH3)2 LA1940 RB4 RB6 C Si(CH3)2 LA1941 RB7 RB6 C Si(CH3)2 LA1942 RB10 RB6 C Si(CH3)2 LA1943 RA3 RB6 C Si(CH3)2 LA1944 RA34 RB6 C Si(CH3)2 LA1945 H H N S LA1946 RB1 H N S LA1947 RB3 H N S LA1948 RB4 H N S LA1949 RB7 H N S LA1950 RB10 H N S LA1951 RA3 H N S LA1952 RA34 H N S LA1953 H H N O LA1954 RB1 H N O LA1955 RB3 H N O LA1956 RB4 H N O LA1957 RB7 H N O LA1958 RB10 H N O LA1959 RA3 H N O LA1960 RA34 H N O LA1961 H H N NCH3 LA1962 RB1 H N NCH3 LA1963 RB3 H N NCH3 LA1964 RB4 H N NCH3 LA1965 RB7 H N NCH3 LA1966 RB10 H N NCH3 LA1967 RA3 H N NCH3 LA1968 RA34 H N NCH3 LA1969 H H N C(CH3)2 LA1970 RB1 H N C(CH3)2 LA1971 RB3 H N C(CH3)2 LA1972 RB4 H N C(CH3)2 LA1973 RB7 H N C(CH3)2 LA1974 RB10 H N C(CH3)2 LA1975 RA3 H N C(CH3)2 LA1976 RA34 H N C(CH3)2 LA1977 H H N Si(CH3)2 LA1978 RB1 H N Si(CH3)2 LA1979 RB3 H N Si(CH3)2 LA1980 RB4 H N Si(CH3)2 LA1981 RB7 H N Si(CH3)2 LA1982 RB10 H N Si(CH3)2 LA1983 RA3 H N Si(CH3)2 LA1984 RA34 H N Si(CH3)2 LA1985 H RB1 N S LA1986 RB1 RB1 N S LA1987 RB3 RB1 N S LA1988 RB4 RB1 N S LA1989 RB7 RB1 N S LA1990 RB10 RB1 N S LA1991 RA3 RB1 N S LA1992 RA34 RB1 N S LA1993 H RB1 N O LA1994 RB1 RB1 N O LA1995 RB3 RB1 N O LA1996 RB4 RB1 N O LA1997 RB7 RB1 N O LA1998 RB10 RB1 N O LA1999 RA3 RB1 N O LA2000 RA34 RB1 N O LA2001 H RB1 N NCH3 LA2002 RB1 RB1 N NCH3 LA2003 RB3 RB1 N NCH3 LA2004 RB4 RB1 N NCH3 LA2005 RB7 RB1 N NCH3 LA2006 RB10 RB1 N NCH3 LA2007 RA3 RB1 N NCH3 LA2008 RA34 RB1 N NCH3 LA2009 H RB1 N C(CH3)2 LA2010 RB1 RB1 N C(CH3)2 LA2011 RB3 RB1 N C(CH3)2 LA2012 RB4 RB1 N C(CH3)2 LA2013 RB7 RB1 N C(CH3)2 LA2014 RB10 RB1 N C(CH3)2 LA2015 RA3 RB1 N C(CH3)2 LA2016 RA34 RB1 N C(CH3)2 LA2017 H RB1 N Si(CH3)2 LA2018 RB1 RB1 N Si(CH3)2 LA2019 RB3 RB1 N Si(CH3)2 LA2020 RB4 RB1 N Si(CH3)2 LA2021 RB7 RB1 N Si(CH3)2 LA2022 RB10 RB1 N Si(CH3)2 LA2023 RA3 RB1 N Si(CH3)2 LA2024 RA34 RB1 N Si(CH3)2 LA2025 H RB6 N S LA2026 RB1 RB6 N S LA2027 RB3 RB6 N S LA2028 RB4 RB6 N S LA2029 RB7 RB6 N S LA2030 RB10 RB6 N S LA2031 RA3 RB6 N S LA2032 RA34 RB6 N S LA2033 H RB6 N O LA2034 RB1 RB6 N O LA2035 RB3 RB6 N O LA2036 RB4 RB6 N O LA2037 RB7 RB6 N O LA2038 RB10 RB6 N O LA2039 RA3 RB6 N O LA2040 RA34 RB6 N O LA2041 H RB6 N NCH3 LA2042 RB1 RB6 N NCH3 LA2043 RB3 RB6 N NCH3 LA2044 RB4 RB6 N NCH3 LA2045 RB7 RB6 N NCH3 LA2046 RB10 RB6 N NCH3 LA2047 RA3 RB6 N NCH3 LA2048 RA34 RB6 N NCH3 LA2049 H RB6 N C(CH3)2 LA2050 RB1 RB6 N C(CH3)2 LA2051 RB3 RB6 N C(CH3)2 LA2052 RB4 RB6 N C(CH3)2 LA2053 RB7 RB6 N C(CH3)2 LA2054 RB10 RB6 N C(CH3)2 LA2055 RA3 RB6 N C(CH3)2 LA2056 RA34 RB6 N C(CH3)2 LA2057 H RB6 N Si(CH3)2 LA2058 RB1 RB6 N Si(CH3)2 LA2059 RB3 RB6 N Si(CH3)2 LA2060 RB4 RB6 N Si(CH3)2 LA2061 RB7 RB6 N Si(CH3)2 LA2062 RB10 RB6 N Si(CH3)2 LA2063 RA3 RB6 N Si(CH3)2 LA2064 RA34 RB6 N Si(CH3)2
wherein LA2065 through LA2184 have a structure of Formula XV: - wherein R3, R5, and Y are defined as provided below:
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Ligand R5 R3 Y Ligand R5 R3 R14 LA2065 H H S LA2125 RB1 RB4 NCH3 LA2066 H RB1 S LA2126 RB1 RB5 NCH3 LA2067 H RB2 S LA2127 RB1 RA34 NCH3 LA2068 H RB3 S LA2128 RB1 RA52 NCH3 LA2069 H RB4 S LA2129 RB1 H C(CH3)2 LA2070 H RB5 S LA2130 RB1 RB1 C(CH3)2 LA2071 H RA34 S LA2131 RB1 RB2 C(CH3)2 LA2072 H RA52 S LA2132 RB1 RB3 C(CH3)2 LA2073 H H O LA2133 RB1 RB4 C(CH3)2 LA2074 H RB1 O LA2134 RB1 RB5 C(CH3)2 LA2075 H RB2 O LA2135 RB1 RA34 C(CH3)2 LA2076 H RB3 O LA2136 RB1 RA52 C(CH3)2 LA2077 H RB4 O LA2137 RB1 H Si(CH3)2 LA2078 H RB5 O LA2138 RB1 RB1 Si(CH3)2 LA2079 H RA34 O LA2139 RB1 RB2 Si(CH3)2 LA2080 H RA52 O LA2140 RB1 RB3 Si(CH3)2 LA2081 H H NCH3 LA2141 RB1 RB4 Si(CH3)2 LA2082 H RB1 NCH3 LA2142 RB1 RB5 Si(CH3)2 LA2083 H RB2 NCH3 LA2143 RB1 RA34 Si(CH3)2 LA2084 H RB3 NCH3 LA2144 RB1 RA52 Si(CH3)2 LA2085 H RB4 NCH3 LA2145 RB6 H S LA2086 H RB5 NCH3 LA2146 RB6 RB1 S LA2087 H RA34 NCH3 LA2147 RB6 RB2 S LA2088 H RA52 NCH3 LA2148 RB6 RB3 S LA2089 H H C(CH3)2 LA2149 RB6 RB4 S LA2090 H RB1 C(CH3)2 LA2150 RB6 RB5 S LA2091 H RB2 C(CH3)2 LA2151 RB6 RA34 S LA2092 H RB3 C(CH3)2 LA2152 RB6 RA52 S LA2093 H RB4 C(CH3)2 LA2153 RB6 H O LA2094 H RB5 C(CH3)2 LA2154 RB6 RB1 O LA2095 H RA34 C(CH3)2 LA2155 RB6 RB2 O LA2096 H RA52 C(CH3)2 LA2156 RB6 RB3 O LA2097 H H Si(CH3)2 LA2157 RB6 RB4 O LA2098 H RB1 Si(CH3)2 LA2158 RB6 RB5 O LA2099 H RB2 Si(CH3)2 LA2159 RB6 RA34 O LA2100 H RB3 Si(CH3)2 LA2160 RB6 RA52 O LA2101 H RB4 Si(CH3)2 LA2161 RB6 H NCH3 LA2102 H RB5 Si(CH3)2 LA2162 RB6 RB1 NCH3 LA2103 H RA34 Si(CH3)2 LA2163 RB6 RB2 NCH3 LA2104 H RA52 Si(CH3)2 LA2164 RB6 RB3 NCH3 LA2105 RB1 H S LA2165 RB6 RB4 NCH3 LA2106 RB1 RB1 S LA2166 RB6 RB5 NCH3 LA2107 RB1 RB2 S LA2167 RB6 RA34 NCH3 LA2108 RB1 RB3 S LA2168 RB6 RA52 NCH3 LA2109 RB1 RB4 S LA2169 RB6 H C(CH3)2 LA2110 RB1 RB5 S LA2170 RB6 RB1 C(CH3)2 LA2111 RB1 RA34 S LA2171 RB6 RB2 C(CH3)2 LA2112 RB1 RA52 S LA2172 RB6 RB3 C(CH3)2 LA2113 RB1 H O LA2173 RB6 RB4 C(CH3)2 LA2114 RB1 RB1 O LA2174 RB6 RB5 C(CH3)2 LA2115 RB1 RB2 O LA2175 RB6 RA34 C(CH3)2 LA2116 RB1 RB3 O LA2176 RB6 RA52 C(CH3)2 LA2117 RB1 RB4 O LA2177 RB6 H Si(CH3)2 LA2118 RB1 RB5 O LA2178 RB6 RB1 Si(CH3)2 LA2119 RB1 RA34 O LA2179 RB6 RB2 Si(CH3)2 LA2120 RB1 RA52 O LA2180 RB6 RB3 Si(CH3)2 LA2121 RB1 H NCH3 LA2181 RB6 RB4 Si(CH3)2 LA2122 RB1 RB1 NCH3 LA2182 RB6 RB5 Si(CH3)2 LA2123 RB1 RB2 NCH3 LA2183 RB6 RA34 Si(CH3)2 LA2124 RB1 RB3 NCH3 LA2184 RB6 RA52 Si(CH3)2
wherein LA2185 through LA2280 have a structure of Formula XVI: - wherein R4, R5, Y, and Z are defined as provided below:
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Ligand R5 R4 Y Z LA2185 H H S S LA2186 H RB1 S S LA2187 H RB3 S S LA2188 H RB4 S S LA2189 H RB7 S S LA2190 H RB10 S S LA2191 H RA3 S S LA2192 H RA34 S S LA2193 H H S O LA2194 H RB1 S O LA2195 H RB3 S O LA2196 H RB4 S O LA2197 H RB7 S O LA2198 H RB10 S O LA2199 H RA3 S O LA2200 H RA34 S O LA2201 H H S NCH3 LA2202 H RB1 S NCH3 LA2203 H RB3 S NCH3 LA2204 H RB4 S NCH3 LA2205 H RB7 S NCH3 LA2206 H RB10 S NCH3 LA2207 H RA3 S NCH3 LA2208 H RA34 S NCH3 LA2209 H H O S LA2210 H RB1 O S LA2211 H RB3 O S LA2212 H RB4 O S LA2213 H RB7 O S LA2214 H RB10 O S LA2215 H RA3 O S LA2216 H RA34 O S LA2217 H H O O LA2218 H RB1 O O LA2219 H RB3 O O LA2220 H RB4 O O LA2221 H RB7 O O LA2222 H RB10 O O LA2223 H RA3 O O LA2224 H RA34 O O LA2225 H H O NCH3 LA2226 H RB1 O NCH3 LA2227 H RB3 O NCH3 LA2228 H RB4 O NCH3 LA2229 H RB7 O NCH3 LA2230 H RB10 O NCH3 LA2231 H RA3 O NCH3 LA2232 H RA34 O NCH3 LA2233 RB6 H S S LA2234 RB6 RB1 S S LA2235 RB6 RB3 S S LA2236 RB6 RB4 S S LA2237 RB6 RB7 S S LA2238 RB6 RB10 S S LA2239 RB6 RA3 S S LA2240 RB6 RA34 S S LA2241 RB6 H S O LA2242 RB6 RB1 S O LA2243 RB6 RB3 S O LA2244 RB6 RB4 S O LA2245 RB6 RB7 S O LA2246 RB6 RB10 S O LA2247 RB6 RA3 S O LA2248 RB6 RA34 S O LA2249 RB6 H S NCH3 LA2250 RB6 RB1 S NCH3 LA2251 RB6 RB3 S NCH3 LA2252 RB6 RB4 S NCH3 LA2253 RB6 RB7 S NCH3 LA2254 RB6 RB10 S NCH3 LA2255 RB6 RA3 S NCH3 LA2256 RB6 RA34 S NCH3 LA2257 RB6 H O S LA2258 RB6 RB1 O S LA2259 RB6 RB3 O S LA2260 RB6 RB4 O S LA2261 RB6 RB7 O S LA2262 RB6 RB10 O S LA2263 RB6 RA3 O S LA2264 RB6 RA34 O S LA2265 RB6 H O O LA2266 RB6 RB1 O O LA2267 RB6 RB3 O O LA2268 RB6 RB4 O O LA2269 RB6 RB7 O O LA2270 RB6 RB10 O O LA2271 RB6 RA3 O O LA2272 RB6 RA34 O O LA2273 RB6 H O NCH3 LA2274 RB6 RB1 O NCH3 LA2275 RB6 RB3 O NCH3 LA2276 RB6 RB4 O NCH3 LA2277 RB6 RB7 O NCH3 LA2278 RB6 RB10 O NCH3 LA2279 RB6 RA3 O NCH3 LA2280 RB6 RA34 O NCH3
wheein LA2281 through LA2520 have a structure of Formula XVII: - wherein R1, R5, X, and Y are defined as provided below:
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Ligand R1 R5 X Y LA2281 H H C S LA2282 RB1 H C S LA2283 RB3 H C S LA2284 RB4 H C S LA2285 RB7 H C S LA2286 RB10 H C S LA2287 RA3 H C S LA2288 RA34 H C S LA2289 H H C O LA2290 RB1 H C O LA2291 RB3 H C O LA2292 RB4 H C O LA2293 RB7 H C O LA2294 RB10 H C O LA2295 RA3 H C O LA2296 RA34 H C O LA2297 H H C NCH3 LA2298 RB1 H C NCH3 LA2299 RB3 H C NCH3 LA2300 RB4 H C NCH3 LA2301 RB7 H C NCH3 LA2302 RB10 H C NCH3 LA2303 RA3 H C NCH3 LA2304 RA34 H C NCH3 LA2305 H H C C(CH3)2 LA2306 RB1 H C C(CH3)2 LA2307 RB3 H C C(CH3)2 LA2308 RB4 H C C(CH3)2 LA2309 RB7 H C C(CH3)2 LA2310 RB10 H C C(CH3)2 LA2311 RA3 H C C(CH3)2 LA2312 RA34 H C C(CH3)2 LA2313 H H C Si(CH3)2 LA2314 RB1 H C Si(CH3)2 LA2315 RB3 H C Si(CH3)2 LA2316 RB4 H C Si(CH3)2 LA2317 RB7 H C Si(CH3)2 LA2318 RB10 H C Si(CH3)2 LA2319 RA3 H C Si(CH3)2 LA2320 RA34 H C Si(CH3)2 LA2321 H RB1 C S LA2322 RB1 RB1 C S LA2323 RB3 RB1 C S LA2324 RB4 RB1 C S LA2325 RB7 RB1 C S LA2326 RB10 RB1 C S LA2327 RA3 RB1 C S LA2328 RA34 RB1 C S LA2329 H RB1 C O LA2330 RB1 RB1 C O LA2331 RB3 RB1 C O LA2332 RB4 RB1 C O LA2333 RB7 RB1 C O LA2334 RB10 RB1 C O LA2335 RA3 RB1 C O LA2336 RA34 RB1 C O LA2337 H RB1 C NCH3 LA2338 RB1 RB1 C NCH3 LA2339 RB3 RB1 C NCH3 LA2340 RB4 RB1 C NCH3 LA2341 RB7 RB1 C NCH3 LA2342 RB10 RB1 C NCH3 LA2343 RA3 RB1 C NCH3 LA2344 RA34 RB1 C NCH3 LA2345 H RB1 C C(CH3)2 LA2346 RB1 RB1 C C(CH3)2 LA2347 RB3 RB1 C C(CH3)2 LA2348 RB4 RB1 C C(CH3)2 LA2349 RB7 RB1 C C(CH3)2 LA2350 RB10 RB1 C C(CH3)2 LA2351 RA3 RB1 C C(CH3)2 LA2352 RA34 RB1 C C(CH3)2 LA2353 H RB1 C Si(CH3)2 LA2354 RB1 RB1 C Si(CH3)2 LA2355 RB3 RB1 C Si(CH3)2 LA2356 RB4 RB1 C Si(CH3)2 LA2357 RB7 RB1 C Si(CH3)2 LA2358 RB10 RB1 C Si(CH3)2 LA2359 RA3 RB1 C Si(CH3)2 LA2360 RA34 RB1 C Si(CH3)2 LA2361 H RB6 C S LA2362 RB1 RB6 C S LA2363 RB3 RB6 C S LA2364 RB4 RB6 C S LA2365 RB7 RB6 C S LA2366 RB10 RB6 C S LA2367 RA3 RB6 C S LA2368 RA34 RB6 C S LA2369 H RB6 C O LA2370 RB1 RB6 C O LA2371 RB3 RB6 C O LA2372 RB4 RB6 C O LA2373 RB7 RB6 C O LA2374 RB10 RB6 C O LA2375 RA3 RB6 C O LA2376 RA34 RB6 C O LA2377 H RB6 C NCH3 LA2378 RB1 RB6 C NCH3 LA2379 RB3 RB6 C NCH3 LA2380 RB4 RB6 C NCH3 LA2381 RB7 RB6 C NCH3 LA2382 RB10 RB6 C NCH3 LA2383 RA3 RB6 C NCH3 LA2384 RA34 RB6 C NCH3 LA2385 H RB6 C C(CH3)2 LA2386 RB1 RB6 C C(CH3)2 LA2387 RB3 RB6 C C(CH3)2 LA2388 RB4 RB6 C C(CH3)2 LA2389 RB7 RB6 C C(CH3)2 LA2390 RB10 RB6 C C(CH3)2 LA2391 RA3 RB6 C C(CH3)2 LA2392 RA34 RB6 C C(CH3)2 LA2393 H RB6 C Si(CH3)2 LA2394 RB1 RB6 C Si(CH3)2 LA2395 RB3 RB6 C Si(CH3)2 LA2396 RB4 RB6 C Si(CH3)2 LA2397 RB7 RB6 C Si(CH3)2 LA2398 RB10 RB6 C Si(CH3)2 LA2399 RA3 RB6 C Si(CH3)2 LA2400 RA34 RB6 C Si(CH3)2 LA2401 H H N S LA2402 RB1 H N S LA2403 RB3 H N S LA2404 RB4 H N S LA2405 RB7 H N S LA2406 RB10 H N S LA2407 RA3 H N S LA2408 RA34 H N S LA2409 H H N O LA2410 RB1 H N O LA2411 RB3 H N O LA2412 RB4 H N O LA2413 RB7 H N O LA2414 RB10 H N O LA2415 RA3 H N O LA2416 RA34 H N O LA2417 H H N NCH3 LA2418 RB1 H N NCH3 LA2419 RB3 H N NCH3 LA2420 RB4 H N NCH3 LA2421 RB7 H N NCH3 LA2422 RB10 H N NCH3 LA2423 RA3 H N NCH3 LA2424 RA34 H N NCH3 LA2425 H H N C(CH3)2 LA2426 RB1 H N C(CH3)2 LA2427 RB3 H N C(CH3)2 LA2428 RB4 H N C(CH3)2 LA2429 RB7 H N C(CH3)2 LA2430 RB10 H N C(CH3)2 LA2431 RA3 H N C(CH3)2 LA2432 RA34 H N C(CH3)2 LA2433 H H N Si(CH3)2 LA2434 RB1 H N Si(CH3)2 LA2435 RB3 H N Si(CH3)2 LA2436 RB4 H N Si(CH3)2 LA2437 RB7 H N Si(CH3)2 LA2438 RB10 H N Si(CH3)2 LA2439 RA3 H N Si(CH3)2 LA2440 RA34 H N Si(CH3)2 LA2441 H RB1 N S LA2442 RB1 RB1 N S LA2443 RB3 RB1 N S LA2444 RB4 RB1 N S LA2445 RB7 RB1 N S LA2446 RB10 RB1 N S LA2447 RA3 RB1 N S LA2448 RA34 RB1 N S LA2449 H RB1 N O LA2450 RB1 RB1 N O LA2451 RB3 RB1 N O LA2452 RB4 RB1 N O LA2453 RB7 RB1 N O LA2454 RB10 RB1 N O LA2455 RA3 RB1 N O LA2456 RA34 RB1 N O LA2457 H RB1 N NCH3 LA2458 RB1 RB1 N NCH3 LA2459 RB3 RB1 N NCH3 LA2460 RB4 RB1 N NCH3 LA2461 RB7 RB1 N NCH3 LA2462 RB10 RB1 N NCH3 LA2463 RA3 RB1 N NCH3 LA2464 RA34 RB1 N NCH3 LA2465 H RB1 N C(CH3)2 LA2466 RB1 RB1 N C(CH3)2 LA2467 RB3 RB1 N C(CH3)2 LA2468 RB4 RB1 N C(CH3)2 LA2469 RB7 RB1 N C(CH3)2 LA2470 RB10 RB1 N C(CH3)2 LA2471 RA3 RB1 N C(CH3)2 LA2472 RA34 RB1 N C(CH3)2 LA2473 H RB1 N Si(CH3)2 LA2474 RB1 RB1 N Si(CH3)2 LA2475 RB3 RB1 N Si(CH3)2 LA2476 RB4 RB1 N Si(CH3)2 LA2477 RB7 RB1 N Si(CH3)2 LA2478 RB10 RB1 N Si(CH3)2 LA2479 RA3 RB1 N Si(CH3)2 LA2480 RA34 RB1 N Si(CH3)2 LA2481 H RB6 N S LA2482 RB1 RB6 N S LA2483 RB3 RB6 N S LA2484 RB4 RB6 N S LA2485 RB7 RB6 N S LA2486 RB10 RB6 N S LA2487 RA3 RB6 N S LA2488 RA34 RB6 N S LA2489 H RB6 N O LA2490 RB1 RB6 N O LA2491 RB3 RB6 N O LA2492 RB4 RB6 N O LA2493 RB7 RB6 N O LA2494 RB10 RB6 N O LA2495 RA3 RB6 N O LA2496 RA34 RB6 N O LA2497 H RB6 N NCH3 LA2498 RB1 RB6 N NCH3 LA2499 RB3 RB6 N NCH3 LA2500 RB4 RB6 N NCH3 LA2501 RB7 RB6 N NCH3 LA2502 RB10 RB6 N NCH3 LA2503 RA3 RB6 N NCH3 LA2504 RA34 RB6 N NCH3 LA2505 H RB6 N C(CH3)2 LA2506 RB1 RB6 N C(CH3)2 LA2507 RB3 RB6 N C(CH3)2 LA2508 RB4 RB6 N C(CH3)2 LA2509 RB7 RB6 N C(CH3)2 LA2510 RB10 RB6 N C(CH3)2 LA2511 RA3 RB6 N C(CH3)2 LA2512 RA34 RB6 N C(CH3)2 LA2513 H RB6 N Si(CH3)2 LA2514 RB1 RB6 N Si(CH3)2 LA2515 RB3 RB6 N Si(CH3)2 LA2516 RB4 RB6 N Si(CH3)2 LA2517 RB7 RB6 N Si(CH3)2 LA2518 RB10 RB6 N Si(CH3)2 LA2519 RA3 RB6 N Si(CH3)2 LA2520 RA34 RB6 N Si(CH3)2
wherein LA2521 through LA2640 have a structure of Formula XVIII: - wherein R3, R5, and Y are defined as provided below:
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Ligand R5 R3 Y Ligand R5 R3 Y LA2521 H H S LA2581 RB1 RB4 NCH3 LA2522 H RB1 S LA2582 RB1 RB5 NCH3 LA2523 H RB2 S LA2583 RB1 RA34 NCH3 LA2524 H RB3 S LA2584 RB1 RA52 NCH3 LA2525 H RB4 S LA2585 RB1 H C(CH3)2 LA2526 H RB5 S LA2586 RB1 RB1 C(CH3)2 LA2527 H RA34 S LA2587 RB1 RB2 C(CH3)2 LA2528 H RA52 S LA2588 RB1 RB3 C(CH3)2 LA2529 H H O LA2589 RB1 RB4 C(CH3)2 LA2530 H RB1 O LA2590 RB1 RB5 C(CH3)2 LA2531 H RB2 O LA2591 RB1 RA34 C(CH3)2 LA2532 H RB3 O LA2592 RB1 RA52 C(CH3)2 LA2533 H RB4 O LA2593 RB1 H Si(CH3)2 LA2534 H RB5 O LA2594 RB1 RB1 Si(CH3)2 LA2535 H RA34 O LA2595 RB1 RB2 Si(CH3)2 LA2536 H RA52 O LA2596 RB1 RB3 Si(CH3)2 LA2537 H H NCH3 LA2597 RB1 RB4 Si(CH3)2 LA2538 H RB1 NCH3 LA2598 RB1 RB5 Si(CH3)2 LA2539 H RB2 NCH3 LA2599 RB1 RA34 Si(CH3)2 LA2540 H RB3 NCH3 LA2600 RB1 RA52 Si(CH3)2 LA2541 H RB4 NCH3 LA2601 RB6 H S LA2542 H RB5 NCH3 LA2602 RB6 RB1 S LA2543 H RA34 NCH3 LA2603 RB6 RB2 S LA2544 H RA52 NCH3 LA2604 RB6 RB3 S LA2545 H H C(CH3)2 LA2605 RB6 RB4 S LA2546 H RB1 C(CH3)2 LA2606 RB6 RB5 S LA2547 H RB2 C(CH3)2 LA2607 RB6 RA34 S LA2548 H RB3 C(CH3)2 LA2608 RB6 RA52 S LA2549 H RB4 C(CH3)2 LA2609 RB6 H O LA2550 H RB5 C(CH3)2 LA2610 RB6 RB1 O LA2551 H RA34 C(CH3)2 LA2611 RB6 RB2 O LA2552 H RA52 C(CH3)2 LA2612 RB6 RB3 O LA2553 H H Si(CH3)2 LA2613 RB6 RB4 O LA2554 H RB1 Si(CH3)2 LA2614 RB6 RB5 O LA2555 H RB2 Si(CH3)2 LA2615 RB6 RA34 O LA2556 H RB3 Si(CH3)2 LA2616 RB6 RA52 O LA2557 H RB4 Si(CH3)2 LA2617 RB6 H NCH3 LA2558 H RB5 Si(CH3)2 LA2618 RB6 RB1 NCH3 LA2559 H RA34 Si(CH3)2 LA2619 RB6 RB2 NCH3 LA2560 H RA52 Si(CH3)2 LA2620 RB6 RB3 NCH3 LA2561 RB1 H S LA2621 RB6 RB4 NCH3 LA2562 RB1 RB1 S LA2622 RB6 RB5 NCH3 LA2563 RB1 RB2 S LA2623 RB6 RA34 NCH3 LA2564 RB1 RB3 S LA2624 RB6 RA52 NCH3 LA2565 RB1 RB4 S LA2625 RB6 H C(CH3)2 LA2566 RB1 RB5 S LA2626 RB6 RB1 C(CH3)2 LA2567 RB1 RA34 S LA2627 RB6 RB2 C(CH3)2 LA2568 RB1 RA52 S LA2628 RB6 RB3 C(CH3)2 LA2569 RB1 H O LA2629 RB6 RB4 C(CH3)2 LA2570 RB1 RB1 O LA2630 RB6 RB5 C(CH3)2 LA2571 RB1 RB2 O LA2631 RB6 RA34 C(CH3)2 LA2572 RB1 RB3 O LA2632 RB6 RA52 C(CH3)2 LA2573 RB1 RB4 O LA2633 RB6 H Si(CH3)2 LA2574 RB1 RB5 O LA2634 RB6 RB1 Si(CH3)2 LA2575 RB1 RA34 O LA2635 RB6 RB2 Si(CH3)2 LA2576 RB1 RA52 O LA2636 RB6 RB3 Si(CH3)2 LA2577 RB1 H NCH3 LA2637 RB6 RB4 Si(CH3)2 LA2578 RB1 RB1 NCH3 LA2638 RB6 RB5 Si(CH3)2 LA2579 RB1 RB2 NCH3 LA2639 RB6 RA34 Si(CH3)2 LA2580 RB1 RB3 NCH3 LA2640 RB6 RA52 Si(CH3)2
wherein LA2641 through LA2736 have a structure of Formula XIX: - wherein R4, R5, Y, and Z are defined as provided below:
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Ligand R5 R4 Y Z Ligand R5 R4 Y Z LA2641 H H S S LA2689 RB6 H S S LA2642 H RB1 S S LA2690 RB6 RB1 S S LA2643 H RB3 S S LA2691 RB6 RB3 S S LA2644 H RB4 S S LA2692 RB6 RB4 S S LA2645 H RB7 S S LA2693 RB6 RB7 S S LA2646 H RB10 S S LA2694 RB6 RB10 S S LA2647 H RA3 S S LA2695 RB6 RA3 S S LA2648 H RA34 S S LA2696 RB6 RA34 S S LA2649 H H S O LA2697 RB6 H S O LA2650 H RB1 S O LA2698 RB6 RB1 S O LA2651 H RB3 S O LA2699 RB6 RB3 S O LA2652 H RB4 S O LA2700 RB6 RB4 S O LA2653 H RB7 S O LA2701 RB6 RB7 S O LA2654 H RB10 S O LA2702 RB6 RB10 S O LA2655 H RA3 S O LA2703 RB6 RA3 S O LA2656 H RA34 S O LA2704 RB6 RA34 S O LA2657 H H S NCH3 LA2705 RB6 H S NCH3 LA2658 H RB1 S NCH3 LA2706 RB6 RB1 S NCH3 LA2659 H RB3 S NCH3 LA2707 RB6 RB3 S NCH3 LA2660 H RB4 S NCH3 LA2708 RB6 RB4 S NCH3 LA2661 H RB7 S NCH3 LA2709 RB6 RB7 S NCH3 LA2662 H RB10 S NCH3 LA2710 RB6 RB10 S NCH3 LA2663 H RA3 S NCH3 LA2711 RB6 RA3 S NCH3 LA2664 H RA34 S NCH3 LA2712 RB6 RA34 S NCH3 LA2665 H H O S LA2713 RB6 H O S LA2666 H RB1 O S LA2714 RB6 RB1 O S LA2667 H RB3 O S LA2715 RB6 RB3 O S LA2668 H RB4 O S LA2716 RB6 RB4 O S LA2669 H RB7 O S LA2717 RB6 RB7 O S LA2670 H RB10 O S LA2718 RB6 RB10 O S LA2671 H RA3 O S LA2719 RB6 RA3 O S LA2672 H RA34 O S LA2720 RB6 RA34 O S LA2673 H H O O LA2721 RB6 H O O LA2674 H RB1 O O LA2722 RB6 RB1 O O LA2675 H RB3 O O LA2723 RB6 RB3 O O LA2676 H RB4 O O LA2724 RB6 RB4 O O LA2677 H RB7 O O LA2725 RB6 RB7 O O LA2678 H RB10 O O LA2726 RB6 RB10 O O LA2679 H RA3 O O LA2727 RB6 RA3 O O LA2680 H RA34 O O LA2728 RB6 RA34 O O LA2681 H H O NCH3 LA2729 RB6 H O NCH3 LA2682 H RB1 O NCH3 LA2730 RB6 RB1 O NCH3 LA2683 H RB3 O NCH3 LA2731 RB6 RB3 O NCH3 LA2684 H RB4 O NCH3 LA2732 RB6 RB4 O NCH3 LA2685 H RB7 O NCH3 LA2733 RB6 RB7 O NCH3 LA2686 H RB10 O NCH3 LA2734 RB6 RB10 O NCH3 LA2687 H RA3 O NCH3 LA2735 RB6 RA3 O NCH3 LA2688 H RA34 O NCH3 LA2736 RB6 RA34 O NCH3
wherein LA2737 through LA2976 have a structure of Formula XX: - wherein R1, R5, Y, and X are defined as provided below:
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Ligand R1 R5 X Y Ligand R1 R5 X Y LA2737 H H C S LA2857 H H N S LA2738 RB1 H C S LA2858 RB1 H N S LA2739 RB3 H C S LA2859 RB3 H N S LA2740 RB4 H C S LA2860 RB4 H N S LA2741 RB7 H C S LA2861 RB7 H N S LA2742 RB10 H C S LA2862 RB10 H N S LA2743 RA3 H C S LA2863 RA3 H N S LA2744 RA34 H C S LA2864 RA34 H N S LA2745 H H C O LA2865 H H N O LA2746 RB1 H C O LA2866 RB1 H N O LA2747 RB3 H C O LA2867 RB3 H N O LA2748 RB4 H C O LA2868 RB4 H N O LA2749 RB7 H C O LA2869 RB7 H N O LA2750 RB10 H C O LA2870 RB10 H N O LA2751 RA3 H C O LA2871 RA3 H N O LA2752 RA34 H C O LA2872 RA34 H N O LA2753 H H C NCH3 LA2873 H H N NCH3 LA2754 RB1 H C NCH3 LA2874 RB1 H N NCH3 LA2755 RB3 H C NCH3 LA2875 RB3 H N NCH3 LA2756 RB4 H C NCH3 LA2876 RB4 H N NCH3 LA2757 RB7 H C NCH3 LA2877 RB7 H N NCH3 LA2758 RB10 H C NCH3 LA2878 RB10 H N NCH3 LA2759 RA3 H C NCH3 LA2879 RA3 H N NCH3 LA2760 RA34 H C NCH3 LA2880 RA34 H N NCH3 LA2761 H H C C(CH3)2 LA2881 H H N C(CH3)2 LA2762 RB1 H C C(CH3)2 LA2882 RB1 H N C(CH3)2 LA2763 RB3 H C C(CH3)2 LA2883 RB3 H N C(CH3)2 LA2764 RB4 H C C(CH3)2 LA2884 RB4 H N C(CH3)2 LA2765 RB7 H C C(CH3)2 LA2885 RB7 H N C(CH3)2 LA2766 RB10 H C C(CH3)2 LA2886 RB10 H N C(CH3)2 LA2767 RA3 H C C(CH3)2 LA2887 RA3 H N C(CH3)2 LA2768 RA34 H C C(CH3)2 LA2888 RA34 H N C(CH3)2 LA2769 H H C Si(CH3)2 LA2889 H H N Si(CH3)2 LA2770 RB1 H C Si(CH3)2 LA2890 RB1 H N Si(CH3)2 LA2771 RB3 H C Si(CH3)2 LA2891 RB3 H N Si(CH3)2 LA2772 RB4 H C Si(CH3)2 LA2892 RB4 H N Si(CH3)2 LA2773 RB7 H C Si(CH3)2 LA2893 RB7 H N Si(CH3)2 LA2774 RB10 H C Si(CH3)2 LA2894 RB10 H N Si(CH3)2 LA2775 RA3 H C Si(CH3)2 LA2895 RA3 H N Si(CH3)2 LA2776 RA34 H C Si(CH3)2 LA2896 RA34 H N Si(CH3)2 LA2777 H RB1 C S LA2897 H RB1 N S LA2778 RB1 RB1 C S LA2898 RB1 RB1 N S LA2779 RB3 RB1 C S LA2899 RB3 RB1 N S LA2780 RB4 RB1 C S LA2900 RB4 RB1 N S LA2781 RB7 RB1 C S LA2901 RB7 RB1 N S LA2782 RB10 RB1 C S LA2902 RB10 RB1 N S LA2783 RA3 RB1 C S LA2903 RA3 RB1 N S LA2784 RA34 RB1 C S LA2904 RA34 RB1 N S LA2785 H RB1 C O LA2905 H RB1 N O LA2786 RB1 RB1 C O LA2906 RB1 RB1 N O LA2787 RB3 RB1 C O LA2907 RB3 RB1 N O LA2788 RB4 RB1 C O LA2908 RB4 RB1 N O LA2789 RB7 RB1 C O LA2909 RB7 RB1 N O LA2790 RB10 RB1 C O LA2910 RB10 RB1 N O LA2791 RA3 RB1 C O LA2911 RA3 RB1 N O LA2792 RA34 RB1 C O LA2912 RA34 RB1 N O LA2793 H RB1 C NCH3 LA2913 H RB1 N NCH3 LA2794 RB1 RB1 C NCH3 LA2914 RB1 RB1 N NCH3 LA2795 RB3 RB1 C NCH3 LA2915 RB3 RB1 N NCH3 LA2796 RB4 RB1 C NCH3 LA2916 RB4 RB1 N NCH3 LA2797 RB7 RB1 C NCH3 LA2917 RB7 RB1 N NCH3 LA2798 RB10 RB1 C NCH3 LA2918 RB10 RB1 N NCH3 LA2799 RA3 RB1 C NCH3 LA2919 RA3 RB1 N NCH3 LA2800 RA34 RB1 C NCH3 LA2920 RA34 RB1 N NCH3 LA2801 H RB1 C C(CH3)2 LA2921 H RB1 N C(CH3)2 LA2802 RB1 RB1 C C(CH3)2 LA2922 RB1 RB1 N C(CH3)2 LA2803 RB3 RB1 C C(CH3)2 LA2923 RB3 RB1 N C(CH3)2 LA2804 RB4 RB1 C C(CH3)2 LA2924 RB4 RB1 N C(CH3)2 LA2805 RB7 RB1 C C(CH3)2 LA2925 RB7 RB1 N C(CH3)2 LA2806 RB10 RB1 C C(CH3)2 LA2926 RB10 RB1 N C(CH3)2 LA2807 RA3 RB1 C C(CH3)2 LA2927 RA3 RB1 N C(CH3)2 LA2808 RA34 RB1 C C(CH3)2 LA2928 RA34 RB1 N C(CH3)2 LA2809 H RB1 C Si(CH3)2 LA2929 H RB1 N Si(CH3)2 LA2810 RB1 RB1 C Si(CH3)2 LA2930 RB1 RB1 N Si(CH3)2 LA2811 RB3 RB1 C Si(CH3)2 LA2931 RB3 RB1 N Si(CH3)2 LA2812 RB4 RB1 C Si(CH3)2 LA2932 RB4 RB1 N Si(CH3)2 LA2813 RB7 RB1 C Si(CH3)2 LA2933 RB7 RB1 N Si(CH3)2 LA2814 RB10 RB1 C Si(CH3)2 LA2934 RB10 RB1 N Si(CH3)2 LA2815 RA3 RB1 C Si(CH3)2 LA2935 RA3 RB1 N Si(CH3)2 LA2816 RA34 RB1 C Si(CH3)2 LA2936 RA34 RB1 N Si(CH3)2 LA2817 H RB6 C S LA2937 H RB6 N S LA2818 RB1 RB6 C S LA2938 RB1 RB6 N S LA2819 RB3 RB6 C S LA2939 RB3 RB6 N S LA2820 RB4 RB6 C S LA2940 RB4 RB6 N S LA2821 RB7 RB6 C S LA2941 RB7 RB6 N S LA2822 RB10 RB6 C S LA2942 RB10 RB6 N S LA2823 RA3 RB6 C S LA2943 RA3 RB6 N S LA2824 RA34 RB6 C S LA2944 RA34 RB6 N S LA2825 H RB6 C O LA2945 H RB6 N O LA2826 RB1 RB6 C O LA2946 RB1 RB6 N O LA2827 RB3 RB6 C O LA2947 RB3 RB6 N O LA2828 RB4 RB6 C O LA2948 RB4 RB6 N O LA2829 RB7 RB6 C O LA2949 RB7 RB6 N O LA2830 RB10 RB6 C O LA2950 RB10 RB6 N O LA2831 RA3 RB6 C O LA2951 RA3 RB6 N O LA2832 RA34 RB6 C O LA2952 RA34 RB6 N O LA2833 H RB6 C NCH3 LA2953 H RB6 N NCH3 LA2834 RB1 RB6 C NCH3 LA2954 RB1 RB6 N NCH3 LA2835 RB3 RB6 C NCH3 LA2955 RB3 RB6 N NCH3 LA2836 RB4 RB6 C NCH3 LA2956 RB4 RB6 N NCH3 LA2837 RB7 RB6 C NCH3 LA2957 RB7 RB6 N NCH3 LA2838 RB10 RB6 C NCH3 LA2958 RB10 RB6 N NCH3 LA2839 RA3 RB6 C NCH3 LA2959 RA3 RB6 N NCH3 LA2840 RA34 RB6 C NCH3 LA2960 RA34 RB6 N NCH3 LA2841 H RB6 C C(CH3)2 LA2961 H RB6 N C(CH3)2 LA2842 RB1 RB6 C C(CH3)2 LA2962 RB1 RB6 N C(CH3)2 LA2843 RB3 RB6 C C(CH3)2 LA2963 RB3 RB6 N C(CH3)2 LA2844 RB4 RB6 C C(CH3)2 LA2964 RB4 RB6 N C(CH3)2 LA2845 RB7 RB6 C C(CH3)2 LA2965 RB7 RB6 N C(CH3)2 LA2846 RB10 RB6 C C(CH3)2 LA2966 RB10 RB6 N C(CH3)2 LA2847 RA3 RB6 C C(CH3)2 LA2967 RA3 RB6 N C(CH3)2 LA2848 RA34 RB6 C C(CH3)2 LA2968 RA34 RB6 N C(CH3)2 LA2849 H RB6 C Si(CH3)2 LA2969 H RB6 N Si(CH3)2 LA2850 RB1 RB6 C Si(CH3)2 LA2970 RB1 RB6 N Si(CH3)2 LA2851 RB3 RB6 C Si(CH3)2 LA2971 RB3 RB6 N Si(CH3)2 LA2852 RB4 RB6 C Si(CH3)2 LA2972 RB4 RB6 N Si(CH3)2 LA2853 RB7 RB6 C Si(CH3)2 LA2973 RB7 RB6 N Si(CH3)2 LA2854 RB10 RB6 C Si(CH3)2 LA2974 RB10 RB6 N Si(CH3)2 LA2855 RA3 RB6 C Si(CH3)2 LA2975 RA3 RB6 N Si(CH3)2 LA2856 RA34 RB6 C Si(CH3)2 LA2976 RA34 RB6 N Si(CH3)2
wherein LA2977 through LA3096 have a structure of Formula XXI: - wherein R3, R5, and Y are defined as provided below:
-
Ligand R5 R3 Y Ligand R5 R3 Y LA2977 H H S LA3037 RB1 RB4 NCH3 LA2978 H RB1 S LA3038 RB1 RB5 NCH3 LA2979 H RB2 S LA3039 RB1 RA34 NCH3 LA2980 H RB3 S LA3040 RB1 RA52 NCH3 LA2981 H RB4 S LA3041 RB1 H C(CH3)2 LA2982 H RB5 S LA3042 RB1 RB1 C(CH3)2 LA2983 H RA34 S LA3043 RB1 RB2 C(CH3)2 LA2984 H RA52 S LA3044 RB1 RB3 C(CH3)2 LA2985 H H O LA3045 RB1 RB4 C(CH3)2 LA2986 H RB1 O LA3046 RB1 RB5 C(CH3)2 LA2987 H RB2 O LA3047 RB1 RA34 C(CH3)2 LA2988 H RB3 O LA3048 RB1 RA52 C(CH3)2 LA2989 H RB4 O LA3049 RB1 H Si(CH3)2 LA2990 H RB5 O LA3050 RB1 RB1 Si(CH3)2 LA2991 H RA34 O LA3051 RB1 RB2 Si(CH3)2 LA2992 H RA52 O LA3052 RB1 RB3 Si(CH3)2 LA2993 H H NCH3 LA3053 RB1 RB4 Si(CH3)2 LA2994 H RB1 NCH3 LA3054 RB1 RB5 Si(CH3)2 LA2995 H RB2 NCH3 LA3055 RB1 RA34 Si(CH3)2 LA2996 H RB3 NCH3 LA3056 RB1 RA52 Si(CH3)2 LA2997 H RB4 NCH3 LA3057 RB6 H S LA2998 H RB5 NCH3 LA3058 RB6 RB1 S LA2999 H RA34 NCH3 LA3059 RB6 RB2 S LA3000 H RA52 NCH3 LA3060 RB6 RB3 S LA3001 H H C(CH3)2 LA3061 RB6 RB4 S LA3002 H RB1 C(CH3)2 LA3062 RB6 RB5 S LA3003 H RB2 C(CH3)2 LA3063 RB6 RA34 S LA3004 H RB3 C(CH3)2 LA3064 RB6 RA52 S LA3005 H RB4 C(CH3)2 LA3065 RB6 H O LA3006 H RB5 C(CH3)2 LA3066 RB6 RB1 O LA3007 H RA34 C(CH3)2 LA3067 RB6 RB2 O LA3008 H RA52 C(CH3)2 LA3068 RB6 RB3 O LA3009 H H Si(CH3)2 LA3069 RB6 RB4 O LA3010 H RB1 Si(CH3)2 LA3070 RB6 RB5 O LA3011 H RB2 Si(CH3)2 LA3071 RB6 RA34 O LA3012 H RB3 Si(CH3)2 LA3072 RB6 RA52 O LA3013 H RB4 Si(CH3)2 LA3073 RB6 H NCH3 LA3014 H RB5 Si(CH3)2 LA3074 RB6 RB1 NCH3 LA3015 H RA34 Si(CH3)2 LA3075 RB6 RB2 NCH3 LA3016 H RA52 Si(CH3)2 LA3076 RB6 RB3 NCH3 LA3017 RB1 H S LA3077 RB6 RB4 NCH3 LA3018 RB1 RB1 S LA3078 RB6 RB5 NCH3 LA3019 RB1 RB2 S LA3079 RB6 RA34 NCH3 LA3020 RB1 RB3 S LA3080 RB6 RA52 NCH3 LA3021 RB1 RB4 S LA3081 RB6 H C(CH3)2 LA3022 RB1 RB5 S LA3082 RB6 RB1 C(CH3)2 LA3023 RB1 RA34 S LA3083 RB6 RB2 C(CH3)2 LA3024 RB1 RA52 S LA3084 RB6 RB3 C(CH3)2 LA3025 RB1 H O LA3085 RB6 RB4 C(CH3)2 LA3026 RB1 RB1 O LA3086 RB6 RB5 C(CH3)2 LA3027 RB1 RB2 O LA3087 RB6 RA34 C(CH3)2 LA3028 RB1 RB3 O LA3088 RB6 RA52 C(CH3)2 LA3029 RB1 RB4 O LA3089 RB6 H Si(CH3)2 LA3030 RB1 RB5 O LA3090 RB6 RB1 Si(CH3)2 LA3031 RB1 RA34 O LA3091 RB6 RB2 Si(CH3)2 LA3032 RB1 RA52 O LA3092 RB6 RB3 Si(CH3)2 LA3033 RB1 H NCH3 LA3093 RB6 RB4 Si(CH3)2 LA3034 RB1 RB1 NCH3 LA3094 RB6 RB5 Si(CH3)2 LA3035 RB1 RB2 NCH3 LA3095 RB6 RA34 Si(CH3)2 LA3036 RB1 RB3 NCH3 LA3096 RB6 RA52 Si(CH3)2
wherein LA3097 through LA3192 have a structure of Formula XXII: - wherein R4, R5, Y, and Z are defined as provided below:
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Ligand R5 R4 Y Z Ligand R5 R4 Y Z LA3097 H H S S LA3145 RB6 H S S LA3098 H RB1 S S LA3146 RB6 RB1 S S LA3099 H RB3 S S LA3147 RB6 RB3 S S LA3100 H RB4 S S LA3148 RB6 RB4 S S LA3101 H RB7 S S LA3149 RB6 RB7 S S LA3102 H RB10 S S LA3150 RB6 RB10 S S LA3103 H RA3 S S LA3151 RB6 RA3 S S LA3104 H RA34 S S LA3152 RB6 RA34 S S LA3105 H H S O LA3153 RB6 H S O LA3106 H RB1 S O LA3154 RB6 RB1 S O LA3107 H RB3 S O LA3155 RB6 RB3 S O LA3108 H RB4 S O LA3156 RB6 RB4 S O LA3109 H RB7 S O LA3157 RB6 RB7 S O LA3110 H RB10 S O LA3158 RB6 RB10 S O LA3111 H RA3 S O LA3159 RB6 RA3 S O LA3112 H RA34 S O LA3160 RB6 RA34 S O LA3113 H H S NCH3 LA3161 RB6 H S NCH3 LA3114 H RB1 S NCH3 LA3162 RB6 RB1 S NCH3 LA3115 H RB3 S NCH3 LA3163 RB6 RB3 S NCH3 LA3116 H RB4 S NCH3 LA3164 RB6 RB4 S NCH3 LA3117 H RB7 S NCH3 LA3165 RB6 RB7 S NCH3 LA3118 H RB10 S NCH3 LA3166 RB6 RB10 S NCH3 LA3119 H RA3 S NCH3 LA3167 RB6 RA3 S NCH3 LA3120 H RA34 S NCH3 LA3168 RB6 RA34 S NCH3 LA3121 H H O S LA3169 RB6 H O S LA3122 H RB1 O S LA3170 RB6 RB1 O S LA3123 H RB3 O S LA3171 RB6 RB3 O S LA3124 H RB4 O S LA3172 RB6 RB4 O S LA3125 H RB7 O S LA3173 RB6 RB7 O S LA3126 H RB10 O S LA3174 RB6 RB10 O S LA3127 H RA3 O S LA3175 RB6 RA3 O S LA3128 H RA34 O S LA3176 RB6 RA34 O S LA3129 H H O O LA3177 RB6 H O O LA3130 H RB1 O O LA3178 RB6 RB1 O O LA3131 H RB3 O O LA3179 RB6 RB3 O O LA3132 H RB4 O O LA3180 RB6 RB4 O O LA3133 H RB7 O O LA3181 RB6 RB7 O O LA3134 H RB10 O O LA3182 RB6 RB10 O O LA3135 H RA3 O O LA3183 RB6 RA3 O O LA3136 H RA34 O O LA3184 RB6 RA34 O O LA3137 H H O NCH3 LA3185 RB6 H O NCH3 LA3138 H RB1 O NCH3 LA3186 RB6 RB1 O NCH3 LA3139 H RB3 O NCH3 LA3187 RB6 RB3 O NCH3 LA3140 H RB4 O NCH3 LA3188 RB6 RB4 O NCH3 LA3141 H RB7 O NCH3 LA3189 RB6 RB7 O NCH3 LA3142 H RB10 O NCH3 LA3190 RB6 RB10 O NCH3 LA3143 H RA3 O NCH3 LA3191 RB6 RA3 O NCH3 LA3144 H RA34 O NCH3 LA3192 RB6 RA34 O NCH3
wherein LA3193 through LA3432 have a structure of Formula XXIII: - wherein R1, R5, X, and Y are defined as provided below:
-
Ligand R1 R5 X Y Ligand R1 R5 X Y LA3193 H H C S LA3313 H H N S LA3194 RB1 H C S LA3314 RB1 H N S LA3195 RB3 H C S LA3315 RB3 H N S LA3196 RB4 H C S LA3316 RB4 H N S LA3197 RB7 H C S LA3317 RB7 H N S LA3198 RB10 H C S LA3318 RB10 H N S LA3199 RA3 H C S LA3319 RA3 H N S LA3200 RA34 H C S LA3320 RA34 H N S LA3201 H H C O LA3321 H H N O LA3202 RB1 H C O LA3322 RB1 H N O LA3203 RB3 H C O LA3323 RB3 H N O LA3204 RB4 H C O LA3324 RB4 H N O LA3205 RB7 H C O LA3325 RB7 H N O LA3206 RB10 H C O LA3326 RB10 H N O LA3207 RA3 H C O LA3327 RA3 H N O LA3208 RA34 H C O LA3328 RA34 H N O LA3209 H H C NCH3 LA3329 H H N NCH3 LA3210 RB1 H C NCH3 LA3330 RB1 H N NCH3 LA3211 RB3 H C NCH3 LA3331 RB3 H N NCH3 LA3212 RB4 H C NCH3 LA3332 RB4 H N NCH3 LA3213 RB7 H C NCH3 LA3333 RB7 H N NCH3 LA3214 RB10 H C NCH3 LA3334 RB10 H N NCH3 LA3215 RA3 H C NCH3 LA3335 RA3 H N NCH3 LA3216 RA34 H C NCH3 LA3336 RA34 H N NCH3 LA3217 H H C C(CH3)2 LA3337 H H N C(CH3)2 LA3218 RB1 H C C(CH3)2 LA3338 RB1 H N C(CH3)2 LA3219 RB3 H C C(CH3)2 LA3339 RB3 H N C(CH3)2 LA3220 RB4 H C C(CH3)2 LA3340 RB4 H N C(CH3)2 LA3221 RB7 H C C(CH3)2 LA3341 RB7 H N C(CH3)2 LA3222 RB10 H C C(CH3)2 LA3342 RB10 H N C(CH3)2 LA3223 RA3 H C C(CH3)2 LA3343 RA3 H N C(CH3)2 LA3224 RA34 H C C(CH3)2 LA3344 RA34 H N C(CH3)2 LA3225 H H C Si(CH3)2 LA3345 H H N Si(CH3)2 LA3226 RB1 H C Si(CH3)2 LA3346 RB1 H N Si(CH3)2 LA3227 RB3 H C Si(CH3)2 LA3347 RB3 H N Si(CH3)2 LA3228 RB4 H C Si(CH3)2 LA3348 RB4 H N Si(CH3)2 LA3229 RB7 H C Si(CH3)2 LA3349 RB7 H N Si(CH3)2 LA3230 RB10 H C Si(CH3)2 LA3350 RB10 H N Si(CH3)2 LA3231 RA3 H C Si(CH3)2 LA3351 RA3 H N Si(CH3)2 LA3232 RA34 H C Si(CH3)2 LA3352 RA34 H N Si(CH3)2 LA3233 H RB1 C S LA3353 H RB1 N S LA3234 RB1 RB1 C S LA3354 RB1 RB1 N S LA3235 RB3 RB1 C S LA3355 RB3 RB1 N S LA3236 RB4 RB1 C S LA3356 RB4 RB1 N S LA3237 RB7 RB1 C S LA3357 RB7 RB1 N S LA3238 RB10 RB1 C S LA3358 RB10 RB1 N S LA3239 RA3 RB1 C S LA3359 RA3 RB1 N S LA3240 RA34 RB1 C S LA3360 RA34 RB1 N S LA3241 H RB1 C O LA3361 H RB1 N O LA3242 RB1 RB1 C O LA3362 RB1 RB1 N O LA3243 RB3 RB1 C O LA3363 RB3 RB1 N O LA3244 RB4 RB1 C O LA3364 RB4 RB1 N O LA3245 RB7 RB1 C O LA3365 RB7 RB1 N O LA3246 RB10 RB1 C O LA3366 RB10 RB1 N O LA3247 RA3 RB1 C O LA3367 RA3 RB1 N O LA3248 RA34 RB1 C O LA3368 RA34 RB1 N O LA3249 H RB1 C NCH3 LA3369 H RB1 N NCH3 LA3250 RB1 RB1 C NCH3 LA3370 RB1 RB1 N NCH3 LA3251 RB3 RB1 C NCH3 LA3371 RB3 RB1 N NCH3 LA3252 RB4 RB1 C NCH3 LA3372 RB4 RB1 N NCH3 LA3253 RB7 RB1 C NCH3 LA3373 RB7 RB1 N NCH3 LA3254 RB10 RB1 C NCH3 LA3374 RB10 RB1 N NCH3 LA3255 RA3 RB1 C NCH3 LA3375 RA3 RB1 N NCH3 LA3256 RA34 RB1 C NCH3 LA3376 RA34 RB1 N NCH3 LA3257 H RB1 C C(CH3)2 LA3377 H RB1 N C(CH3)2 LA3258 RB1 RB1 C C(CH3)2 LA3378 RB1 RB1 N C(CH3)2 LA3259 RB3 RB1 C C(CH3)2 LA3379 RB3 RB1 N C(CH3)2 LA3260 RB4 RB1 C C(CH3)2 LA3380 RB4 RB1 N C(CH3)2 LA3261 RB7 RB1 C C(CH3)2 LA3381 RB7 RB1 N C(CH3)2 LA3262 RB10 RB1 C C(CH3)2 LA3382 RB10 RB1 N C(CH3)2 LA3263 RA3 RB1 C C(CH3)2 LA3383 RA3 RB1 N C(CH3)2 LA3264 RA34 RB1 C C(CH3)2 LA3384 RA34 RB1 N C(CH3)2 LA3265 H RB1 C Si(CH3)2 LA3385 H RB1 N Si(CH3)2 LA3266 RB1 RB1 C Si(CH3)2 LA3386 RB1 RB1 N Si(CH3)2 LA3267 RB3 RB1 C Si(CH3)2 LA3387 RB3 RB1 N Si(CH3)2 LA3268 RB4 RB1 C Si(CH3)2 LA3388 RB4 RB1 N Si(CH3)2 LA3269 RB7 RB1 C Si(CH3)2 LA3389 RB7 RB1 N Si(CH3)2 LA3270 RB10 RB1 C Si(CH3)2 LA3390 RB10 RB1 N Si(CH3)2 LA3271 RA3 RB1 C Si(CH3)2 LA3391 RA3 RB1 N Si(CH3)2 LA3272 RA34 RB1 C Si(CH3)2 LA3392 RA34 RB1 N Si(CH3)2 LA3273 H RB6 C S LA3393 H RB6 N S LA3274 RB1 RB6 C S LA3394 RB1 RB6 N S LA3275 RB3 RB6 C S LA3395 RB3 RB6 N S LA3276 RB4 RB6 C S LA3396 RB4 RB6 N S LA3277 RB7 RB6 C S LA3397 RB7 RB6 N S LA3278 RB10 RB6 C S LA3398 RB10 RB6 N S LA3279 RA3 RB6 C S LA3399 RA3 RB6 N S LA3280 RA34 RB6 C S LA3400 RA34 RB6 N S LA3281 H RB6 C O LA3401 H RB6 N O LA3282 RB1 RB6 C O LA3402 RB1 RB6 N O LA3283 RB3 RB6 C O LA3403 RB3 RB6 N O LA3284 RB4 RB6 C O LA3404 RB4 RB6 N O LA3285 RB7 RB6 C O LA3405 RB7 RB6 N O LA3286 RB10 RB6 C O LA3406 RB10 RB6 N O LA3287 RA3 RB6 C O LA3407 RA3 RB6 N O LA3288 RA34 RB6 C O LA3408 RA34 RB6 N O LA3289 H RB6 C NCH3 LA3409 H RB6 N NCH3 LA3290 RB1 RB6 C NCH3 LA3410 RB1 RB6 N NCH3 LA3291 RB3 RB6 C NCH3 LA3411 RB3 RB6 N NCH3 LA3292 RB4 RB6 C NCH3 LA3412 RB4 RB6 N NCH3 LA3293 RB7 RB6 C NCH3 LA3413 RB7 RB6 N NCH3 LA3294 RB10 RB6 C NCH3 LA3414 RB10 RB6 N NCH3 LA3295 RA3 RB6 C NCH3 LA3415 RA3 RB6 N NCH3 LA3296 RA34 RB6 C NCH3 LA3416 RA34 RB6 N NCH3 LA3297 H RB6 C C(CH3)2 LA3417 H RB6 N C(CH3)2 LA3298 RB1 RB6 C C(CH3)2 LA3418 RB1 RB6 N C(CH3)2 LA3299 RB3 RB6 C C(CH3)2 LA3419 RB3 RB6 N C(CH3)2 LA3300 RB4 RB6 C C(CH3)2 LA3420 RB4 RB6 N C(CH3)2 LA3301 RB7 RB6 C C(CH3)2 LA3421 RB7 RB6 N C(CH3)2 LA3302 RB10 RB6 C C(CH3)2 LA3422 RB10 RB6 N C(CH3)2 LA3303 RA3 RB6 C C(CH3)2 LA3423 RA3 RB6 N C(CH3)2 LA3304 RA34 RB6 C C(CH3)2 LA3424 RA34 RB6 N C(CH3)2 LA3305 H RB6 C Si(CH3)2 LA3425 H RB6 N Si(CH3)2 LA3306 RB1 RB6 C Si(CH3)2 LA3426 RB1 RB6 N Si(CH3)2 LA3307 RB3 RB6 C Si(CH3)2 LA3427 RB3 RB6 N Si(CH3)2 LA3308 RB4 RB6 C Si(CH3)2 LA3428 RB4 RB6 N Si(CH3)2 LA3309 RB7 RB6 C Si(CH3)2 LA3429 RB7 RB6 N Si(CH3)2 LA3310 RB10 RB6 C Si(CH3)2 LA3430 RB10 RB6 N Si(CH3)2 LA3311 RA3 RB6 C Si(CH3)2 LA3431 RA3 RB6 N Si(CH3)2 LA3312 RA34 RB6 C Si(CH3)2 LA3432 RA34 RB6 N
wherein LA3433 through LA3552 have a structure of Formula XXIV: - wherein R3, R5, and Y are defined as provided below:
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Ligand R5 R3 Y LA3433 H H S LA3434 H RB1 S LA3435 H RB2 S LA3436 H RB3 S LA3437 H RB4 S LA3438 H RB5 S LA3439 H RA34 S LA3440 H RA52 S LA3441 H H O LA3442 H RB1 O LA3443 H RB2 O LA3444 H RB3 O LA3445 H RB4 O LA3446 H RB5 O LA3447 H RA34 O LA3448 H RA52 O LA3449 H H NCH3 LA3450 H RB1 NCH3 LA3451 H RB2 NCH3 LA3452 H RB3 NCH3 LA3453 H RB4 NCH3 LA3454 H RB5 NCH3 LA3455 H RA34 NCH3 LA3456 H RA52 NCH3 LA3457 H H C(CH3)2 LA3458 H RB1 C(CH3)2 LA3459 H RB2 C(CH3)2 LA3460 H RB3 C(CH3)2 LA3461 H RB4 C(CH3)2 LA3462 H RB5 C(CH3)2 LA3463 H RA34 C(CH3)2 LA3464 H RA52 C(CH3)2 LA3465 H H Si(CH3)2 LA3466 H RB1 Si(CH3)2 LA3467 H RB2 Si(CH3)2 LA3468 H RB3 Si(CH3)2 LA3469 H RB4 Si(CH3)2 LA3470 H RB5 Si(CH3)2 LA3471 H RA34 Si(CH3)2 LA3472 H RA52 Si(CH3)2 LA3473 RB1 H S LA3474 RB1 RB1 S LA3475 RB1 RB2 S LA3476 RB1 RB3 S LA3477 RB1 RB4 S LA3478 RB1 RB5 S LA3479 RB1 RA34 S LA3480 RB1 RA52 S LA3481 RB1 H O LA3482 RB1 RB1 O LA3483 RB1 RB2 O LA3484 RB1 RB3 O LA3485 RB1 RB4 O LA3486 RB1 RB5 O LA3487 RB1 RA34 O LA3488 RB1 RA52 O LA3489 RB1 H NCH3 LA3490 RB1 RB1 NCH3 LA3491 RB1 RB2 NCH3 LA3492 RB1 RB3 NCH3 LA3493 RB1 RB4 NCH3 LA3494 RB1 RB5 NCH3 LA3495 RB1 RA34 NCH3 LA3496 RB1 RA52 NCH3 LA3497 RB1 H C(CH3)2 LA3498 RB1 RB1 C(CH3)2 LA3499 RB1 RB2 C(CH3)2 LA3500 RB1 RB3 C(CH3)2 LA3501 RB1 RB4 C(CH3)2 LA3502 RB1 RB5 C(CH3)2 LA3503 RB1 RA34 C(CH3)2 LA3504 RB1 RA52 C(CH3)2 LA3505 RB1 H Si(CH3)2 LA3506 RB1 RB1 Si(CH3)2 LA3507 RB1 RB2 Si(CH3)2 LA3508 RB1 RB3 Si(CH3)2 LA3509 RB1 RB4 Si(CH3)2 LA3510 RB1 RB5 Si(CH3)2 LA3511 RB1 RA34 Si(CH3)2 LA3512 RB1 RA52 Si(CH3)2 LA3513 RB6 H S LA3514 RB6 RB1 S LA3515 RB6 RB2 S LA3516 RB6 RB3 S LA3517 RB6 RB4 S LA3518 RB6 RB5 S LA3519 RB6 RA34 S LA3520 RB6 RA52 S LA3521 RB6 H O LA3522 RB6 RB1 O LA3523 RB6 RB2 O LA3524 RB6 RB3 O LA3525 RB6 RB4 O LA3526 RB6 RB5 O LA3527 RB6 RA34 O LA3528 RB6 RA52 O LA3529 RB6 H NCH3 LA3530 RB6 RB1 NCH3 LA3531 RB6 RB2 NCH3 LA3532 RB6 RB3 NCH3 LA3533 RB6 RB4 NCH3 LA3534 RB6 RB5 NCH3 LA3535 RB6 RA34 NCH3 LA3536 RB6 RA52 NCH3 LA3537 RB6 H C(CH3)2 LA3538 RB6 RB1 C(CH3)2 LA3539 RB6 RB2 C(CH3)2 LA3540 RB6 RB3 C(CH3)2 LA3541 RB6 RB4 C(CH3)2 LA3542 RB6 RB5 C(CH3)2 LA3543 RB6 RA34 C(CH3)2 LA3544 RB6 RA52 C(CH3)2 LA3545 RB6 H Si(CH3)2 LA3546 RB6 RB1 Si(CH3)2 LA3547 RB6 RB2 Si(CH3)2 LA3548 RB6 RB3 Si(CH3)2 LA3549 RB6 RB4 Si(CH3)2 LA3550 RB6 RB5 Si(CH3)2 LA3551 RB6 RA34 Si(CH3)2 LA3552 RB6 RA52 Si(CH3)2
wherein LA3553 through LA3648 have a structure of Formula XXV: - wherein R4, R5, Y, and Z are defined as provided below:
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Ligand R5 R4 Y Z LA3553 H H S S LA3554 H RB1 S S LA3555 H RB3 S S LA3556 H RB4 S S LA3557 H RB7 S S LA3558 H RB10 S S LA3559 H RA3 S S LA3560 H RA34 S S LA3561 H H S O LA3562 H RB1 S O LA3563 H RB3 S O LA3564 H RB4 S O LA3565 H RB7 S O LA3566 H RB10 S O LA3567 H RA3 S O LA3568 H RA34 S O LA3569 H H S NCH3 LA3570 H RB1 S NCH3 LA3571 H RB3 S NCH3 LA3572 H RB4 S NCH3 LA3573 H RB7 S NCH3 LA3574 H RB10 S NCH3 LA3575 H RA3 S NCH3 LA3576 H RA34 S NCH3 LA3577 H H O S LA3578 H RB1 O S LA3579 H RB3 O S LA3580 H RB4 O S LA3581 H RB7 O S LA3582 H RB10 O S LA3583 H RA3 O S LA3584 H RA34 O S LA3585 H H O O LA3586 H RB1 O O LA3587 H RB3 O O LA3588 H RB4 O O LA3589 H RB7 O O LA3590 H RB10 O O LA3591 H RA3 O O LA3592 H RA34 O O LA3593 H H O NCH3 LA3594 H RB1 O NCH3 LA3595 H RB3 O NCH3 LA3596 H RB4 O NCH3 LA3597 H RB7 O NCH3 LA3598 H RB10 O NCH3 LA3599 H RA3 O NCH3 LA3600 H RA34 O NCH3 LA3601 RB6 H S S LA3602 RB6 RB1 S S LA3603 RB6 RB3 S S LA3604 RB6 RB4 S S LA3605 RB6 RB7 S S LA3606 RB6 RB10 S S LA3607 RB6 RA3 S S LA3608 RB6 RA34 S S LA3609 RB6 H S O LA3610 RB6 RB1 S O LA3611 RB6 RB3 S O LA3612 RB6 RB4 S O LA3613 RB6 RB7 S O LA3614 RB6 RB10 S O LA3615 RB6 RA3 S O LA3616 RB6 RA34 S O LA3617 RB6 H S NCH3 LA3618 RB6 RB1 S NCH3 LA3619 RB6 RB3 S NCH3 LA3620 RB6 RB4 S NCH3 LA3621 RB6 RB7 S NCH3 LA3622 RB6 RB10 S NCH3 LA3623 RB6 RA3 S NCH3 LA3624 RB6 RA34 S NCH3 LA3625 RB6 H O S LA3626 RB6 RB1 O S LA3627 RB6 RB3 O S LA3628 RB6 RB4 O S LA3629 RB6 RB7 O S LA3630 RB6 RB10 O S LA3631 RB6 RA3 O S LA3632 RB6 RA34 O S LA3633 RB6 H O O LA3634 RB6 RB1 O O LA3635 RB6 RB3 O O LA3636 RB6 RB4 O O LA3637 RB6 RB7 O O LA3638 RB6 RB10 O O LA3639 RB6 RA3 O O LA3640 RB6 RA34 O O LA3641 RB6 H O NCH3 LA3642 RB6 RB1 O NCH3 LA3643 RB6 RB3 O NCH3 LA3644 RB6 RB4 O NCH3 LA3645 RB6 RB7 O NCH3 LA3646 RB6 RB10 O NCH3 LA3647 RB6 RA3 O NCH3 LA3648 RB6 RA34 O NCH3
wherein LA3649 through LA3888 have a structure of Formula XXVI: - wherein R1, R5, X, and Y are defined as provided below:
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Ligand R1 R5 X Y LA3649 H H C S LA3650 RB1 H C S LA3651 RB3 H C S LA3652 RB4 H C S LA3653 RB7 H C S LA3654 RB10 H C S LA3655 RA3 H C S LA3656 RA34 H C S LA3657 H H C O LA3658 RB1 H C O LA3659 RB3 H C O LA3660 RB4 H C O LA3661 RB7 H C O LA3662 RB10 H C O LA3663 RA3 H C O LA3664 RA34 H C O LA3665 H H C NCH3 LA3666 RB1 H C NCH3 LA3667 RB3 H C NCH3 LA3668 RB4 H C NCH3 LA3669 RB7 H C NCH3 LA3670 RB10 H C NCH3 LA3671 RA3 H C NCH3 LA3672 RA34 H C NCH3 LA3673 H H C C(CH3)2 LA3674 RB1 H C C(CH3)2 LA3675 RB3 H C C(CH3)2 LA3676 RB4 H C C(CH3)2 LA3677 RB7 H C C(CH3)2 LA3678 RB10 H C C(CH3)2 LA3679 RA3 H C C(CH3)2 LA3680 RA34 H C C(CH3)2 LA3681 H H C Si(CH3)2 LA3682 RB1 H C Si(CH3)2 LA3683 RB3 H C Si(CH3)2 LA3684 RB4 H C Si(CH3)2 LA3685 RB7 H C Si(CH3)2 LA3686 RB10 H C Si(CH3)2 LA3687 RA3 H C Si(CH3)2 LA3688 RA34 H C Si(CH3)2 LA3689 H RB1 C S LA3690 RB1 RB1 C S LA3691 RB3 RB1 C S LA3692 RB4 RB1 C S LA3693 RB7 RB1 C S LA3694 RB10 RB1 C S LA3695 RA3 RB1 C S LA3696 RA34 RB1 C S LA3697 H RB1 C O LA3698 RB1 RB1 C O LA3699 RB3 RB1 C O LA3700 RB4 RB1 C O LA3701 RB7 RB1 C O LA3702 RB10 RB1 C O LA3703 RA3 RB1 C O LA3704 RA34 RB1 C O LA3705 H RB1 C NCH3 LA3706 RB1 RB1 C NCH3 LA3707 RB3 RB1 C NCH3 LA3708 RB4 RB1 C NCH3 LA3709 RB7 RB1 C NCH3 LA3710 RB10 RB1 C NCH3 LA3711 RA3 RB1 C NCH3 LA3712 RA34 RB1 C NCH3 LA3713 H RB1 C C(CH3)2 LA3714 RB1 RB1 C C(CH3)2 LA3715 RB3 RB1 C C(CH3)2 LA3716 RB4 RB1 C C(CH3)2 LA3717 RB7 RB1 C C(CH3)2 LA3718 RB10 RB1 C C(CH3)2 LA3719 RA3 RB1 C C(CH3)2 LA3720 RA34 RB1 C C(CH3)2 LA3721 H RB1 C Si(CH3)2 LA3722 RB1 RB1 C Si(CH3)2 LA3723 RB3 RB1 C Si(CH3)2 LA3724 RB4 RB1 C Si(CH3)2 LA3725 RB7 RB1 C Si(CH3)2 LA3726 RB10 RB1 C Si(CH3)2 LA3727 RA3 RB1 C Si(CH3)2 LA3728 RA34 RB1 C Si(CH3)2 LA3729 H RB6 C S LA3730 RB1 RB6 C S LA3731 RB3 RB6 C S LA3732 RB4 RB6 C S LA3733 RB7 RB6 C S LA3734 RB10 RB6 C S LA3735 RA3 RB6 C S LA3736 RA34 RB6 C S LA3737 H RB6 C O LA3738 RB1 RB6 C O LA3739 RB3 RB6 C O LA3740 RB4 RB6 C O LA3741 RB7 RB6 C O LA3742 RB10 RB6 C O LA3743 RA3 RB6 C O LA3744 RA34 RB6 C O LA3745 H RB6 C NCH3 LA3746 RB1 RB6 C NCH3 LA3747 RB3 RB6 C NCH3 LA3748 RB4 RB6 C NCH3 LA3749 RB7 RB6 C NCH3 LA3750 RB10 RB6 C NCH3 LA3751 RA3 RB6 C NCH3 LA3752 RA34 RB6 C NCH3 LA3753 H RB6 C C(CH3)2 LA3754 RB1 RB6 C C(CH3)2 LA3755 RB3 RB6 C C(CH3)2 LA3756 RB4 RB6 C C(CH3)2 LA3757 RB7 RB6 C C(CH3)2 LA3758 RB10 RB6 C C(CH3)2 LA3759 RA3 RB6 C C(CH3)2 LA3760 RA34 RB6 C C(CH3)2 LA3761 H RB6 C Si(CH3)2 LA3762 RB1 RB6 C Si(CH3)2 LA3763 RB3 RB6 C Si(CH3)2 LA3764 RB4 RB6 C Si(CH3)2 LA3765 RB7 RB6 C Si(CH3)2 LA3766 RB10 RB6 C Si(CH3)2 LA3767 RA3 RB6 C Si(CH3)2 LA3768 RA34 RB6 C Si(CH3)2 LA3769 H H N S LA3770 RB1 H N S LA3771 RB3 H N S LA3772 RB4 H N S LA3773 RB7 H N S LA3774 RB10 H N S LA3775 RA3 H N S LA3776 RA34 H N S LA3777 H H N O LA3778 RB1 H N O LA3779 RB3 H N O LA3780 RB4 H N O LA3781 RB7 H N O LA3782 RB10 H N O LA3783 RA3 H N O LA3784 RA34 H N O LA3785 H H N NCH3 LA3786 RB1 H N NCH3 LA3787 RB3 H N NCH3 LA3788 RB4 H N NCH3 LA3789 RB7 H N NCH3 LA3790 RB10 H N NCH3 LA3791 RA3 H N NCH3 LA3792 RA34 H N NCH3 LA3793 H H N C(CH3)2 LA3794 RB1 H N C(CH3)2 LA3795 RB3 H N C(CH3)2 LA3796 RB4 H N C(CH3)2 LA3797 RB7 H N C(CH3)2 LA3798 RB10 H N C(CH3)2 LA3799 RA3 H N C(CH3)2 LA3800 RA34 H N C(CH3)2 LA3801 H H N Si(CH3)2 LA3802 RB1 H N Si(CH3)2 LA3803 RB3 H N Si(CH3)2 LA3804 RB4 H N Si(CH3)2 LA3805 RB7 H N Si(CH3)2 LA3806 RB10 H N Si(CH3)2 LA3807 RA3 H N Si(CH3)2 LA3808 RA34 H N Si(CH3)2 LA3809 H RB1 N S LA3810 RB1 RB1 N S LA3811 RB3 RB1 N S LA3812 RB4 RB1 N S LA3813 RB7 RB1 N S LA3814 RB10 RB1 N S LA3815 RA3 RB1 N S LA3816 RA34 RB1 N S LA3817 H RB1 N O LA3818 RB1 RB1 N O LA3819 RB3 RB1 N O LA3820 RB4 RB1 N O LA3821 RB7 RB1 N O LA3822 RB10 RB1 N O LA3823 RA3 RB1 N O LA3824 RA34 RB1 N O LA3825 H RB1 N NCH3 LA3826 RB1 RB1 N NCH3 LA3827 RB3 RB1 N NCH3 LA3828 RB4 RB1 N NCH3 LA3829 RB7 RB1 N NCH3 LA3830 RB10 RB1 N NCH3 LA3831 RA3 RB1 N NCH3 LA3832 RA34 RB1 N NCH3 LA3833 H RB1 N C(CH3)2 LA3834 RB1 RB1 N C(CH3)2 LA3835 RB3 RB1 N C(CH3)2 LA3836 RB4 RB1 N C(CH3)2 LA3837 RB7 RB1 N C(CH3)2 LA3838 RB10 RB1 N C(CH3)2 LA3839 RA3 RB1 N C(CH3)2 LA3840 RA34 RB1 N C(CH3)2 LA3841 H RB1 N Si(CH3)2 LA3842 RB1 RB1 N Si(CH3)2 LA3843 RB3 RB1 N Si(CH3)2 LA3844 RB4 RB1 N Si(CH3)2 LA3845 RB7 RB1 N Si(CH3)2 LA3846 RB10 RB1 N Si(CH3)2 LA3847 RA3 RB1 N Si(CH3)2 LA3848 RA34 RB1 N Si(CH3)2 LA3849 H RB6 N S LA3850 RB1 RB6 N S LA3851 RB3 RB6 N S LA3852 RB4 RB6 N S LA3853 RB7 RB6 N S LA3854 RB10 RB6 N S LA3855 RA3 RB6 N S LA3856 RA34 RB6 N S LA3857 H RB6 N O LA3858 RB1 RB6 N O LA3859 RB3 RB6 N O LA3860 RB4 RB6 N O LA3861 RB7 RB6 N O LA3862 RB10 RB6 N O LA3863 RA3 RB6 N O LA3864 RA34 RB6 N O LA3865 H RB6 N NCH3 LA3866 RB1 RB6 N NCH3 LA3867 RB3 RB6 N NCH3 LA3868 RB4 RB6 N NCH3 LA3869 RB7 RB6 N NCH3 LA3870 RB10 RB6 N NCH3 LA3871 RA3 RB6 N NCH3 LA3872 RA34 RB6 N NCH3 LA3873 H RB6 N C(CH3)2 LA3874 RB1 RB6 N C(CH3)2 LA3875 RB3 RB6 N C(CH3)2 LA3876 RB4 RB6 N C(CH3)2 LA3877 RB7 RB6 N C(CH3)2 LA3878 RB10 RB6 N C(CH3)2 LA3879 RA3 RB6 N C(CH3)2 LA3880 RA34 RB6 N C(CH3)2 LA3881 H RB6 N Si(CH3)2 LA3882 RB1 RB6 N Si(CH3)2 LA3883 RB3 RB6 N Si(CH3)2 LA3884 RB4 RB6 N Si(CH3)2 LA3885 RB7 RB6 N Si(CH3)2 LA3886 RB10 RB6 N Si(CH3)2 LA3887 RA3 RB6 N Si(CH3)2 LA3888 RA34 RB6 N Si(CH3)2
wherein LA3889 through LA4008 have a structure of Formula XXVII - wherein R3, R5, and Y are defined as provided below:
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Ligand R5 R3 Y LA3889 H H S LA3890 H RB1 S LA3891 H RB2 S LA3892 H RB3 S LA3893 H RB4 S LA3894 H RB5 S LA3895 H RA34 S LA3896 H RA52 S LA3897 H H O LA3898 H RB1 O LA3899 H RB2 O LA3900 H RB3 O LA3901 H RB4 O LA3902 H RB5 O LA3903 H RA34 O LA3904 H RA52 O LA3905 H H NCH3 LA3906 H RB1 NCH3 LA3907 H RB2 NCH3 LA3908 H RB3 NCH3 LA3909 H RB4 NCH3 LA3910 H RB5 NCH3 LA3911 H RA34 NCH3 LA3912 H RA52 NCH3 LA3913 H H C(CH3)2 LA3914 H RB1 C(CH3)2 LA3915 H RB2 C(CH3)2 LA3916 H RB3 C(CH3)2 LA3917 H RB4 C(CH3)2 LA3918 H RB5 C(CH3)2 LA3919 H RA34 C(CH3)2 LA3920 H RA52 C(CH3)2 LA3921 H H Si(CH3)2 LA3922 H RB1 Si(CH3)2 LA3923 H RB2 Si(CH3)2 LA3924 H RB3 Si(CH3)2 LA3925 H RB4 Si(CH3)2 LA3926 H RB5 Si(CH3)2 LA3927 H RA34 Si(CH3)2 LA3928 H RA52 Si(CH3)2 LA3929 RB1 H S LA3930 RB1 RB1 S LA3931 RB1 RB2 S LA3932 RB1 RB3 S LA3933 RB1 RB4 S LA3934 RB1 RB5 S LA3935 RB1 RA34 S LA3936 RB1 RA52 S LA3937 RB1 H O LA3938 RB1 RB1 O LA3939 RB1 RB2 O LA3940 RB1 RB3 O LA3941 RB1 RB4 O LA3942 RB1 RB5 O LA3943 RB1 RA34 O LA3944 RB1 RA52 O LA3945 RB1 H NCH3 LA3946 RB1 RB1 NCH3 LA3947 RB1 RB2 NCH3 LA3948 RB1 RB3 NCH3 LA3949 RB1 RB4 NCH3 LA3950 RB1 RB5 NCH3 LA3951 RB1 RA34 NCH3 LA3952 RB1 RA52 NCH3 LA3953 RB1 H C(CH3)2 LA3954 RB1 RB1 C(CH3)2 LA3955 RB1 RB2 C(CH3)2 LA3956 RB1 RB3 C(CH3)2 LA3957 RB1 RB4 C(CH3)2 LA3958 RB1 RB5 C(CH3)2 LA3959 RB1 RA34 C(CH3)2 LA3960 RB1 RA52 C(CH3)2 LA3961 RB1 H Si(CH3)2 LA3962 RB1 RB1 Si(CH3)2 LA3963 RB1 RB2 Si(CH3)2 LA3964 RB1 RB3 Si(CH3)2 LA3965 RB1 RB4 Si(CH3)2 LA3966 RB1 RB5 Si(CH3)2 LA3967 RB1 RA34 Si(CH3)2 LA3968 RB1 RA52 Si(CH3)2 LA3969 RB6 H S LA3970 RB6 RB1 S LA3971 RB6 RB2 S LA3972 RB6 RB3 S LA3973 RB6 RB4 S LA3974 RB6 RB5 S LA3975 RB6 RA34 S LA3976 RB6 RA52 S LA3977 RB6 H O LA3978 RB6 RB1 O LA3979 RB6 RB2 O LA3980 RB6 RB3 O LA3981 RB6 RB4 O LA3982 RB6 RB5 O LA3983 RB6 RA34 O LA3984 RB6 RA52 O LA3985 RB6 H NCH3 LA3986 RB6 RB1 NCH3 LA3987 RB6 RB2 NCH3 LA3988 RB6 RB3 NCH3 LA3989 RB6 RB4 NCH3 LA3990 RB6 RB5 NCH3 LA3991 RB6 RA34 NCH3 LA3992 RB6 RA52 NCH3 LA3993 RB6 H C(CH3)2 LA3994 RB6 RB1 C(CH3)2 LA3995 RB6 RB2 C(CH3)2 LA3996 RB6 RB3 C(CH3)2 LA3997 RB6 RB4 C(CH3)2 LA3998 RB6 RB5 C(CH3)2 LA3999 RB6 RA34 C(CH3)2 LA4000 RB6 RA52 C(CH3)2 LA4001 RB6 H Si(CH3)2 LA4002 RB6 RB1 Si(CH3)2 LA4003 RB6 RB2 Si(CH3)2 LA4004 RB6 RB3 Si(CH3)2 LA4005 RB6 RB4 Si(CH3)2 LA4006 RB6 RB5 Si(CH3)2 LA4007 RB6 RA34 Si(CH3)2 LA4008 RB6 RA52 Si(CH3)2
wherein LA4009 through LA4104 have a structure of Formula XXVII: - wherein R4, R5, Y, and Z are defined as provided below:
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Ligand R5 R4 Y Z LA4009 H H S S LA4010 H RB1 S S LA4011 H RB3 S S LA4012 H RB4 S S LA4013 H RB7 S S LA4014 H RB10 S S LA4015 H RA3 S S LA4016 H RA34 S S LA4017 H H S O LA4018 H RB1 S O LA4019 H RB3 S O LA4020 H RB4 S O LA4021 H RB7 S O LA4022 H RB10 S O LA4023 H RA3 S O LA4024 H RA34 S O LA4025 H H S NCH3 LA4026 H RB1 S NCH3 LA4027 H RB3 S NCH3 LA4028 H RB4 S NCH3 LA4029 H RB7 S NCH3 LA4030 H RB10 S NCH3 LA4031 H RA3 S NCH3 LA4032 H RA34 S NCH3 LA4033 H H O S LA4034 H RB1 O S LA4035 H RB3 O S LA4036 H RB4 O S LA4037 H RB7 O S LA4038 H RB10 O S LA4039 H RA3 O S LA4040 H RA34 O S LA4041 H H O O LA4042 H RB1 O O LA4043 H RB3 O O LA4044 H RB4 O O LA4045 H RB7 O O LA4046 H RB10 O O LA4047 H RA3 O O LA4048 H RA34 O O LA4049 H H O NCH3 LA4050 H RB1 O NCH3 LA4051 H RB3 O NCH3 LA4052 H RB4 O NCH3 LA4053 H RB7 O NCH3 LA4054 H RB10 O NCH3 LA4055 H RA3 O NCH3 LA4056 H RA34 O NCH3 LA4057 RB6 H S S LA4058 RB6 RB1 S S LA4059 RB6 RB3 S S LA4060 RB6 RB4 S S LA4061 RB6 RB7 S S LA4062 RB6 RB10 S S LA4063 RB6 RA3 S S LA4064 RB6 RA34 S S LA4065 RB6 H S O LA4066 RB6 RB1 S O LA4067 RB6 RB3 S O LA4068 RB6 RB4 S O LA4069 RB6 RB7 S O LA4070 RB6 RB10 S O LA4071 RB6 RA3 S O LA4072 RB6 RA34 S O LA4073 RB6 H S NCH3 LA4074 RB6 RB1 S NCH3 LA4075 RB6 RB3 S NCH3 LA4076 RB6 RB4 S NCH3 LA4077 RB6 RB7 S NCH3 LA4078 RB6 RB10 S NCH3 LA4079 RB6 RA3 S NCH3 LA4080 RB6 RA34 S NCH3 LA4081 RB6 H O S LA4082 RB6 RB1 O S LA4083 RB6 RB3 O S LA4084 RB6 RB4 O S LA4085 RB6 RB7 O S LA4086 RB6 RB10 O S LA4087 RB6 RA3 O S LA4088 RB6 RA34 O S LA4089 RB6 H O O LA4090 RB6 RB1 O O LA4091 RB6 RB3 O O LA4092 RB6 RB4 O O LA4093 RB6 RB7 O O LA4094 RB6 RB10 O O LA4095 RB6 RA3 O O LA4096 RB6 RA34 O O LA4097 RB6 H O NCH3 LA4098 RB6 RB1 O NCH3 LA4099 RB6 RB3 O NCH3 LA4100 RB6 RB4 O NCH3 LA4101 RB6 RB7 O NCH3 LA4102 RB6 RB10 O NCH3 LA4103 RB6 RA3 O NCH3 LA4104 RB6 RA34 O NCH3
wherein LA4105 through LA4344 have a structure of Formula XXIX: - wherein R1, R5, X, and Y are defined as provided below:
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Ligand R1 R5 X Y LA4105 H H C S LA4106 RB1 H C S LA4107 RB3 H C S LA4108 RB4 H C S LA4109 RB7 H C S LA4110 RB10 H C S LA4111 RA3 H C S LA4112 RA34 H C S LA4113 H H C O LA4114 RB1 H C O LA4115 RB3 H C O LA4116 RB4 H C O LA4117 RB7 H C O LA4118 RB10 H C O LA4119 RA3 H C O LA4120 RA34 H C O LA4121 H H C NCH3 LA4122 RB1 H C NCH3 LA4123 RB3 H C NCH3 LA4124 RB4 H C NCH3 LA4125 RB7 H C NCH3 LA4126 RB10 H C NCH3 LA4127 RA3 H C NCH3 LA4128 RA34 H C NCH3 LA4129 H H C C(CH3)2 LA4130 RB1 H C C(CH3)2 LA4131 RB3 H C C(CH3)2 LA4132 RB4 H C C(CH3)2 LA4133 RB7 H C C(CH3)2 LA4134 RB10 H C C(CH3)2 LA4135 RA3 H C C(CH3)2 LA4136 RA34 H C C(CH3)2 LA4137 H H C Si(CH3)2 LA4138 RB1 H C Si(CH3)2 LA4139 RB3 H C Si(CH3)2 LA4140 RB4 H C Si(CH3)2 LA4141 RB7 H C Si(CH3)2 LA4142 RB10 H C Si(CH3)2 LA4143 RA3 H C Si(CH3)2 LA4144 RA34 H C Si(CH3)2 LA4145 H RB1 C S LA4146 RB1 RB1 C S LA4147 RB3 RB1 C S LA4148 RB4 RB1 C S LA4149 RB7 RB1 C S LA4150 RB10 RB1 C S LA4151 RA3 RB1 C S LA4152 RA34 RB1 C S LA4153 H RB1 C O LA4154 RB1 RB1 C O LA4155 RB3 RB1 C O LA4156 RB4 RB1 C O LA4157 RB7 RB1 C O LA4158 RB10 RB1 C O LA4159 RA3 RB1 C O LA4160 RA34 RB1 C O LA4161 H RB1 C NCH3 LA4162 RB1 RB1 C NCH3 LA4163 RB3 RB1 C NCH3 LA4164 RB4 RB1 C NCH3 LA4165 RB7 RB1 C NCH3 LA4166 RB10 RB1 C NCH3 LA4167 RA3 RB1 C NCH3 LA4168 RA34 RB1 C NCH3 LA4169 H RB1 C C(CH3)2 LA4170 RB1 RB1 C C(CH3)2 LA4171 RB3 RB1 C C(CH3)2 LA4172 RB4 RB1 C C(CH3)2 LA4173 RB7 RB1 C C(CH3)2 LA4174 RB10 RB1 C C(CH3)2 LA4175 RA3 RB1 C C(CH3)2 LA4176 RA34 RB1 C C(CH3)2 LA4177 H RB1 C Si(CH3)2 LA4178 RB1 RB1 C Si(CH3)2 LA4179 RB3 RB1 C Si(CH3)2 LA4180 RB4 RB1 C Si(CH3)2 LA4181 RB7 RB1 C Si(CH3)2 LA4182 RB10 RB1 C Si(CH3)2 LA4183 RA3 RB1 C Si(CH3)2 LA4184 RA34 RB1 C Si(CH3)2 LA4185 H RB6 C S LA4186 RB1 RB6 C S LA4187 RB3 RB6 C S LA4188 RB4 RB6 C S LA4189 RB7 RB6 C S LA4190 RB10 RB6 C S LA4191 RA3 RB6 C S LA4192 RA34 RB6 C S LA4193 H RB6 C O LA4194 RB1 RB6 C O LA4195 RB3 RB6 C O LA4196 RB4 RB6 C O LA4197 RB7 RB6 C O LA4198 RB10 RB6 C O LA4199 RA3 RB6 C O LA4200 RA34 RB6 C O LA4201 H RB6 C NCH3 LA4202 RB1 RB6 C NCH3 LA4203 RB3 RB6 C NCH3 LA4204 RB4 RB6 C NCH3 LA4205 RB7 RB6 C NCH3 LA4206 RB10 RB6 C NCH3 LA4207 RA3 RB6 C NCH3 LA4208 RA34 RB6 C NCH3 LA4209 H RB6 C C(CH3)2 LA4210 RB1 RB6 C C(CH3)2 LA4211 RB3 RB6 C C(CH3)2 LA4212 RB4 RB6 C C(CH3)2 LA4213 RB7 RB6 C C(CH3)2 LA4214 RB10 RB6 C C(CH3)2 LA4215 RA3 RB6 C C(CH3)2 LA4216 RA34 RB6 C C(CH3)2 LA4217 H RB6 C Si(CH3)2 LA4218 RB1 RB6 C Si(CH3)2 LA4219 RB3 RB6 C Si(CH3)2 LA4220 RB4 RB6 C Si(CH3)2 LA4221 RB7 RB6 C Si(CH3)2 LA4222 RB10 RB6 C Si(CH3)2 LA4223 RA3 RB6 C Si(CH3)2 LA4224 RA34 RB6 C Si(CH3)2 LA4225 H H N S LA4226 RB1 H N S LA4227 RB3 H N S LA4228 RB4 H N S LA4229 RB7 H N S LA4230 RB10 H N S LA4231 RA3 H N S LA4232 RA34 H N S LA4233 H H N O LA4234 RB1 H N O LA4235 RB3 H N O LA4236 RB4 H N O LA4237 RB7 H N O LA4238 RB10 H N O LA4239 RA3 H N O LA4240 RA34 H N O LA4241 H H N NCH3 LA4242 RB1 H N NCH3 LA4243 RB3 H N NCH3 LA4244 RB4 H N NCH3 LA4245 RB7 H N NCH3 LA4246 RB10 H N NCH3 LA4247 RA3 H N NCH3 LA4248 RA34 H N NCH3 LA4249 H H N C(CH3)2 LA4250 RB1 H N C(CH3)2 LA4251 RB3 H N C(CH3)2 LA4252 RB4 H N C(CH3)2 LA4253 RB7 H N C(CH3)2 LA4254 RB10 H N C(CH3)2 LA4255 RA3 H N C(CH3)2 LA4256 RA34 H N C(CH3)2 LA4257 H H N Si(CH3)2 LA4258 RB1 H N Si(CH3)2 LA4259 RB3 H N Si(CH3)2 LA4260 RB4 H N Si(CH3)2 LA4261 RB7 H N Si(CH3)2 LA4262 RB10 H N Si(CH3)2 LA4263 RA3 H N Si(CH3)2 LA4264 RA34 H N Si(CH3)2 LA4265 H RB1 N S LA4266 RB1 RB1 N S LA4267 RB3 RB1 N S LA4268 RB4 RB1 N S LA4269 RB7 RB1 N S LA4270 RB10 RB1 N S LA4271 RA3 RB1 N S LA4272 RA34 RB1 N S LA4273 H RB1 N O LA4274 RB1 RB1 N O LA4275 RB3 RB1 N O LA4276 RB4 RB1 N O LA4277 RB7 RB1 N O LA4278 RB10 RB1 N O LA4279 RA3 RB1 N O LA4280 RA34 RB1 N O LA4281 H RB1 N NCH3 LA4282 RB1 RB1 N NCH3 LA4283 RB3 RB1 N NCH3 LA4284 RB4 RB1 N NCH3 LA4285 RB7 RB1 N NCH3 LA4286 RB10 RB1 N NCH3 LA4287 RA3 RB1 N NCH3 LA4288 RA34 RB1 N NCH3 LA4289 H RB1 N C(CH3)2 LA4290 RB1 RB1 N C(CH3)2 LA4291 RB3 RB1 N C(CH3)2 LA4292 RB4 RB1 N C(CH3)2 LA4293 RB7 RB1 N C(CH3)2 LA4294 RB10 RB1 N C(CH3)2 LA4295 RA3 RB1 N C(CH3)2 LA4296 RA34 RB1 N C(CH3)2 LA4297 H RB1 N Si(CH3)2 LA4298 RB1 RB1 N Si(CH3)2 LA4299 RB3 RB1 N Si(CH3)2 LA4300 RB4 RB1 N Si(CH3)2 LA4301 RB7 RB1 N Si(CH3)2 LA4302 RB10 RB1 N Si(CH3)2 LA4303 RA3 RB1 N Si(CH3)2 LA4304 RA34 RB1 N Si(CH3)2 LA4305 H RB6 N S LA4306 RB1 RB6 N S LA4307 RB3 RB6 N S LA4308 RB4 RB6 N S LA4309 RB7 RB6 N S LA4310 RB10 RB6 N S LA4311 RA3 RB6 N S LA4312 RA34 RB6 N S LA4313 H RB6 N O LA4314 RB1 RB6 N O LA4315 RB3 RB6 N O LA4316 RB4 RB6 N O LA4317 RB7 RB6 N O LA4318 RB10 RB6 N O LA4319 RA3 RB6 N O LA4320 RA34 RB6 N O LA4321 H RB6 N NCH3 LA4322 RB1 RB6 N NCH3 LA4323 RB3 RB6 N NCH3 LA4324 RB4 RB6 N NCH3 LA4325 RB7 RB6 N NCH3 LA4326 RB10 RB6 N NCH3 LA4327 RA3 RB6 N NCH3 LA4328 RA34 RB6 N NCH3 LA4329 H RB6 N C(CH3)2 LA4330 RB1 RB6 N C(CH3)2 LA4331 RB3 RB6 N C(CH3)2 LA4332 RB4 RB6 N C(CH3)2 LA4333 RB7 RB6 N C(CH3)2 LA4334 RB10 RB6 N C(CH3)2 LA4335 RA3 RB6 N C(CH3)2 LA4336 RA34 RB6 N C(CH3)2 LA4337 H RB6 N Si(CH3)2 LA4338 RB1 RB6 N Si(CH3)2 LA4339 RB3 RB6 N Si(CH3)2 LA4340 RB4 RB6 N Si(CH3)2 LA4341 RB7 RB6 N Si(CH3)2 LA4342 RB10 RB6 N Si(CH3)2 LA4343 RA3 RB6 N Si(CH3)2 LA4344 RA34 RB6 N Si(CH3)2
wherein LA4345 through LA4464 have a structure of Formula XXX: - wherein R3, R5, and Y are defined as provided below:
-
Ligand R5 R3 Y LA4345 H H S LA4346 H RB1 S LA4347 H RB2 S LA4348 H RB3 S LA4349 H RB4 S LA4350 H RB5 S LA4351 H RA34 S LA4352 H RA52 S LA4353 H H O LA4354 H RB1 O LA4355 H RB2 O LA4356 H RB3 O LA4357 H RB4 O LA4358 H RB5 O LA4359 H RA34 O LA4360 H RA52 O LA4361 H H NCH3 LA4362 H RB1 NCH3 LA4363 H RB2 NCH3 LA4364 H RB3 NCH3 LA4365 H RB4 NCH3 LA4366 H RB5 NCH3 LA4367 H RA34 NCH3 LA4368 H RA52 NCH3 LA4369 H H C(CH3)2 LA4370 H RB1 C(CH3)2 LA4371 H RB2 C(CH3)2 LA4372 H RB3 C(CH3)2 LA4373 H RB4 C(CH3)2 LA4374 H RB5 C(CH3)2 LA4375 H RA34 C(CH3)2 LA4376 H RA52 C(CH3)2 LA4377 H H Si(CH3)2 LA4378 H RB1 Si(CH3)2 LA4379 H RB2 Si(CH3)2 LA4380 H RB3 Si(CH3)2 LA4381 H RB4 Si(CH3)2 LA4382 H RB5 Si(CH3)2 LA4383 H RA34 Si(CH3)2 LA4384 H RA52 Si(CH3)2 LA4385 RB1 H S LA4386 RB1 RB1 S LA4387 RB1 RB2 S LA4388 RB1 RB3 S LA4389 RB1 RB4 S LA4390 RB1 RB5 S LA4391 RB1 RA34 S LA4392 RB1 RA52 S LA4393 RB1 H O LA4394 RB1 RB1 O LA4395 RB1 RB2 O LA4396 RB1 RB3 O LA4397 RB1 RB4 O LA4398 RB1 RB5 O LA4399 RB1 RA34 O LA4400 RB1 RA52 O LA4401 RB1 H NCH3 LA4402 RB1 RB1 NCH3 LA4403 RB1 RB2 NCH3 LA4404 RB1 RB3 NCH3 LA4405 RB1 RB4 NCH3 LA4406 RB1 RB5 NCH3 LA4407 RB1 RA34 NCH3 LA4408 RB1 RA52 NCH3 LA4409 RB1 H C(CH3)2 LA4410 RB1 RB1 C(CH3)2 LA4411 RB1 RB2 C(CH3)2 LA4412 RB1 RB3 C(CH3)2 LA4413 RB1 RB4 C(CH3)2 LA4414 RB1 RB5 C(CH3)2 LA4415 RB1 RA34 C(CH3)2 LA4416 RB1 RA52 C(CH3)2 LA4417 RB1 H Si(CH3)2 LA4418 RB1 RB1 Si(CH3)2 LA4419 RB1 RB2 Si(CH3)2 LA4420 RB1 RB3 Si(CH3)2 LA4421 RB1 RB4 Si(CH3)2 LA4422 RB1 RB5 Si(CH3)2 LA4423 RB1 RA34 Si(CH3)2 LA4424 RB1 RA52 Si(CH3)2 LA4425 RB6 H S LA4426 RB6 RB1 S LA4427 RB6 RB2 S LA4428 RB6 RB3 S LA4429 RB6 RB4 S LA4430 RB6 RB5 S LA4431 RB6 RA34 S LA4432 RB6 RA52 S LA4433 RB6 H O LA4434 RB6 RB1 O LA4435 RB6 RB2 O LA4436 RB6 RB3 O LA4437 RB6 RB4 O LA4438 RB6 RB5 O LA4439 RB6 RA34 O LA4440 RB6 RA52 O LA4441 RB6 H NCH3 LA4442 RB6 RB1 NCH3 LA4443 RB6 RB2 NCH3 LA4444 RB6 RB3 NCH3 LA4445 RB6 RB4 NCH3 LA4446 RB6 RB5 NCH3 LA4447 RB6 RA34 NCH3 LA4448 RB6 RA52 NCH3 LA4449 RB6 H C(CH3)2 LA4450 RB6 RB1 C(CH3)2 LA4451 RB6 RB2 C(CH3)2 LA4452 RB6 RB3 C(CH3)2 LA4453 RB6 RB4 C(CH3)2 LA4454 RB6 RB5 C(CH3)2 LA4455 RB6 RA34 C(CH3)2 LA4456 RB6 RA52 C(CH3)2 LA4457 RB6 H Si(CH3)2 LA4458 RB6 RB1 Si(CH3)2 LA4459 RB6 RB2 Si(CH3)2 LA4460 RB6 RB3 Si(CH3)2 LA4461 RB6 RB4 Si(CH3)2 LA4462 RB6 RB5 Si(CH3)2 LA4463 RB6 RA34 Si(CH3)2 LA4464 RB6 RA52 Si(CH3)2
wherein LA4465 through LA4560 have a structure of Formula XXXI: - wherein R4, R5, Y, and Z are defined as provided below:
-
Ligand R5 R4 Y Z LA4465 H H S S LA4466 H RB1 S S LA4467 H RB3 S S LA4468 H RB4 S S LA4469 H RB7 S S LA4470 H RB10 S S LA4471 H RA3 S S LA4472 H RA34 S S LA4473 H H S O LA4474 H RB1 S O LA4475 H RB3 S O LA4476 H RB4 S O LA4477 H RB7 S O LA4478 H RB10 S O LA4479 H RA3 S O LA4480 H RA34 S O LA4481 H H S NCH3 LA4482 H RB1 S NCH3 LA4483 H RB3 S NCH3 LA4484 H RB4 S NCH3 LA4485 H RB7 S NCH3 LA4486 H RB10 S NCH3 LA4487 H RA3 S NCH3 LA4488 H RA34 S NCH3 LA4489 H H O S LA4490 H RB1 O S LA4491 H RB3 O S LA4492 H RB4 O S LA4493 H RB7 O S LA4494 H RB10 O S LA4495 H RA3 O S LA4496 H RA34 O S LA4497 H H O O LA4498 H RB1 O O LA4499 H RB3 O O LA4500 H RB4 O O LA4501 H RB7 O O LA4502 H RB10 O O LA4503 H RA3 O O LA4504 H RA34 O O LA4505 H H O NCH3 LA4506 H RB1 O NCH3 LA4507 H RB3 O NCH3 LA4508 H RB4 O NCH3 LA4509 H RB7 O NCH3 LA4510 H RB10 O NCH3 LA4511 H RA3 O NCH3 LA4512 H RA34 O NCH3 LA4513 RB6 H S S LA4514 RB6 RB1 S S LA4515 RB6 RB3 S S LA4516 RB6 RB4 S S LA4517 RB6 RB7 S S LA4518 RB6 RB10 S S LA4519 RB6 RA3 S S LA4520 RB6 RA34 S S LA4521 RB6 H S O LA4522 RB6 RB1 S O LA4523 RB6 RB3 S O LA4524 RB6 RB4 S O LA4525 RB6 RB7 S O LA4526 RB6 RB10 S O LA4527 RB6 RA3 S O LA4528 RB6 RA34 S O LA4529 RB6 H S NCH3 LA4530 RB6 RB1 S NCH3 LA4531 RB6 RB3 S NCH3 LA4532 RB6 RB4 S NCH3 LA4533 RB6 RB7 S NCH3 LA4534 RB6 RB10 S NCH3 LA4535 RB6 RA3 S NCH3 LA4536 RB6 RA34 S NCH3 LA4537 RB6 H O S LA4538 RB6 RB1 O S LA4539 RB6 RB3 O S LA4540 RB6 RB4 O S LA4541 RB6 RB7 O S LA4542 RB6 RB10 O S LA4543 RB6 RA3 O S LA4544 RB6 RA34 O S LA4545 RB6 H O O LA4546 RB6 RB1 O O LA4547 RB6 RB3 O O LA4548 RB6 RB4 O O LA4549 RB6 RB7 O O LA4550 RB6 RB10 O O LA4551 RB6 RA3 O O LA4552 RB6 RA34 O O LA4553 RB6 H O NCH3 LA4554 RB6 RB1 O NCH3 LA4555 RB6 RB3 O NCH3 LA4556 RB6 RB4 O NCH3 LA4557 RB6 RB7 O NCH3 LA4558 RB6 RB10 O NCH3 LA4559 RB6 RA3 O NCH3 LA4560 RB6 RA34 O NCH3
wherein LA4561 through LA4780 have a structure of Formula XXXII: - wherein R1, R2, R3, and Y are defined as provided below:
-
Ligand R1 R3 R2 Y LA4561 H H H O LA4562 RB1 RB1 H O LA4563 RB3 RB3 H O LA4564 RB4 RB4 H O LA4565 RB7 RB7 H O LA4566 RB10 RB10 H O LA4567 RA3 RA3 H O LA4568 RA34 RA34 H O LA4569 RB1 H H O LA4570 RB3 H H O LA4571 RB4 H H O LA4572 RB7 H H O LA4573 RB10 H H O LA4574 RA3 H H O LA4575 RA34 H H O LA4576 H RB1 H O LA4577 H RB3 H O LA4578 H RB4 H O LA4579 H RB7 H O LA4580 H RB10 H O LA4581 H RA3 H O LA4582 H RA34 H O LA4583 H H H S LA4584 RB1 RB1 H S LA4585 RB3 RB3 H S LA4586 RB4 RB4 H S LA4587 RB7 RB7 H S LA4588 RB10 RB10 H S LA4589 RA3 RA3 H S LA4590 RA34 RA34 H S LA4591 RB1 H H S LA4592 RB3 H H S LA4593 RB4 H H S LA4594 RB7 H H S LA4595 RB10 H H S LA4596 RA3 H H S LA4597 RA34 H H S LA4598 H RB1 H S LA4599 H RB3 H S LA4600 H RB4 H S LA4601 H RB7 H S LA4602 H RB10 H S LA4603 H RA3 H S LA4604 H RA34 H S LA4605 H H H NCH3 LA4606 RB1 RB1 H NCH3 LA4607 RB3 RB3 H NCH3 LA4608 RB4 RB4 H NCH3 LA4609 RB7 RB7 H NCH3 LA4610 RB10 RB10 H NCH3 LA4611 RA3 RA3 H NCH3 LA4612 RA34 RA34 H NCH3 LA4613 RB1 H H NCH3 LA4614 RB3 H H NCH3 LA4615 RB4 H H NCH3 LA4616 RB7 H H NCH3 LA4617 RB10 H H NCH3 LA4618 RA3 H H NCH3 LA4619 RA34 H H NCH3 LA4620 H RB1 H NCH3 LA4621 H RB3 H NCH3 LA4622 H RB4 H NCH3 LA4623 H RB7 H NCH3 LA4624 H RB10 H NCH3 LA4625 H RA3 H NCH3 LA4626 H RA34 H NCH3 LA4627 H H H C(CH3)2 LA4628 RB1 RB1 H C(CH3)2 LA4629 RB3 RB3 H C(CH3)2 LA4630 RB4 RB4 H C(CH3)2 LA4631 RB7 RB7 H C(CH3)2 LA4632 RB10 RB10 H C(CH3)2 LA4633 RA3 RA3 H C(CH3)2 LA4634 RA34 RA34 H C(CH3)2 LA4635 RB1 H H C(CH3)2 LA4636 RB3 H H C(CH3)2 LA4637 RB4 H H C(CH3)2 LA4638 RB7 H H C(CH3)2 LA4639 RB10 H H C(CH3)2 LA4640 RA3 H H C(CH3)2 LA4641 RA34 H H C(CH3)2 LA4642 H RB1 H C(CH3)2 LA4643 H RB3 H C(CH3)2 LA4644 H RB4 H C(CH3)2 LA4645 H RB7 H C(CH3)2 LA4646 H RB10 H C(CH3)2 LA4647 H RA3 H C(CH3)2 LA4648 H RA34 H C(CH3)2 LA4649 H H H Si(CH3)2 LA4650 RB1 RB1 H Si(CH3)2 LA4651 RB3 RB3 H Si(CH3)2 LA4652 RB4 RB4 H Si(CH3)2 LA4653 RB7 RB7 H Si(CH3)2 LA4654 RB10 RB10 H Si(CH3)2 LA4655 RA3 RA3 H Si(CH3)2 LA4656 RA34 RA34 H Si(CH3)2 LA4657 RB1 H H Si(CH3)2 LA4658 RB3 H H Si(CH3)2 LA4659 RB4 H H Si(CH3)2 LA4660 RB7 H H Si(CH3)2 LA4661 RB10 H H Si(CH3)2 LA4662 RA3 H H Si(CH3)2 LA4663 RA34 H H Si(CH3)2 LA4664 H RB1 H Si(CH3)2 LA4665 H RB3 H Si(CH3)2 LA4666 H RB4 H Si(CH3)2 LA4667 H RB7 H Si(CH3)2 LA4668 H RB10 H Si(CH3)2 LA4669 H RA3 H Si(CH3)2 LA4670 H RA34 H Si(CH3)2 LA4671 H H RB1 O LA4672 RB1 RB1 RB1 O LA4673 RB3 RB3 RB1 O LA4674 RB4 RB4 RB1 O LA4675 RB7 RB7 RB1 O LA4676 RB10 RB10 RB1 O LA4677 RA3 RA3 RB1 O LA4678 RA34 RA34 RB1 O LA4679 RB1 H RB1 O LA4680 RB3 H RB1 O LA4681 RB4 H RB1 O LA4682 RB7 H RB1 O LA4683 RB10 H RB1 O LA4684 RA3 H RB1 O LA4685 RA34 H RB1 O LA4686 H RB1 RB1 O LA4687 H RB3 RB1 O LA4688 H RB4 RB1 O LA4689 H RB7 RB1 O LA4690 H RB10 RB1 O LA4691 H RA3 RB1 O LA4692 H RA34 RB1 O LA4693 H H RB1 S LA4694 RB1 RB1 RB1 S LA4695 RB3 RB3 RB1 S LA4696 RB4 RB4 RB1 S LA4697 RB7 RB7 RB1 S LA4698 RB10 RB10 RB1 S LA4699 RA3 RA3 RB1 S LA4700 RA34 RA34 RB1 S LA4701 RB1 H RB1 S LA4702 RB3 H RB1 S LA4703 RB4 H RB1 S LA4704 RB7 H RB1 S LA4705 RB10 H RB1 S LA4706 RA3 H RB1 S LA4707 RA34 H RB1 S LA4708 H RB1 RB1 S LA4709 H RB3 RB1 S LA4710 H RB4 RB1 S LA4711 H RB7 RB1 S LA4712 H RB10 RB1 S LA4713 H RA3 RB1 S LA4714 H RA34 RB1 S LA4715 H H RB1 NCH3 LA4716 RB1 RB1 RB1 NCH3 LA4717 RB3 RB3 RB1 NCH3 LA4718 RB4 RB4 RB1 NCH3 LA4719 RB7 RB7 RB1 NCH3 LA4720 RB10 RB10 RB1 NCH3 LA4721 RA3 RA3 RB1 NCH3 LA4722 RA34 RA34 RB1 NCH3 LA4723 RB1 H RB1 NCH3 LA4724 RB3 H RB1 NCH3 LA4725 RB4 H RB1 NCH3 LA4726 RB7 H RB1 NCH3 LA4727 RB10 H RB1 NCH3 LA4728 RA3 H RB1 NCH3 LA4729 RA34 H RB1 NCH3 LA4730 H RB1 RB1 NCH3 LA4731 H RB3 RB1 NCH3 LA4732 H RB4 RB1 NCH3 LA4733 H RB7 RB1 NCH3 LA4734 H RB10 RB1 NCH3 LA4735 H RA3 RB1 NCH3 LA4736 H RA34 RB1 NCH3 LA4737 H H RB1 C(CH3)2 LA4738 RB1 RB1 RB1 C(CH3)2 LA4739 RB3 RB3 RB1 C(CH3)2 LA4740 RB4 RB4 RB1 C(CH3)2 LA4741 RB7 RB7 RB1 C(CH3)2 LA4742 RB10 RB10 RB1 C(CH3)2 LA4743 RA3 RA3 RB1 C(CH3)2 LA4744 RA34 RA34 RB1 C(CH3)2 LA4745 RB1 H RB1 C(CH3)2 LA4746 RB3 H RB1 C(CH3)2 LA4747 RB4 H RB1 C(CH3)2 LA4748 RB7 H RB1 C(CH3)2 LA4749 RB10 H RB1 C(CH3)2 LA4750 RA3 H RB1 C(CH3)2 LA4751 RA34 H RB1 C(CH3)2 LA4752 H RB1 RB1 C(CH3)2 LA4753 H RB3 RB1 C(CH3)2 LA4754 H RB4 RB1 C(CH3)2 LA4755 H RB7 RB1 C(CH3)2 LA4756 H RB10 RB1 C(CH3)2 LA4757 H RA3 RB1 C(CH3)2 LA4758 H RA34 RB1 C(CH3)2 LA4759 H H RB1 Si(CH3)2 LA4760 RB1 RB1 RB1 Si(CH3)2 LA4761 RB3 RB3 RB1 Si(CH3)2 LA4762 RB4 RB4 RB1 Si(CH3)2 LA4763 RB7 RB7 RB1 Si(CH3)2 LA4764 RB10 RB10 RB1 Si(CH3)2 LA4765 RA3 RA3 RB1 Si(CH3)2 LA4766 RA34 RA34 RB1 Si(CH3)2 LA4767 RB1 H RB1 Si(CH3)2 LA4768 RB3 H RB1 Si(CH3)2 LA4769 RB4 H RB1 Si(CH3)2 LA4770 RB7 H RB1 Si(CH3)2 LA4771 RB10 H RB1 Si(CH3)2 LA4772 RA3 H RB1 Si(CH3)2 LA4773 RA34 H RB1 Si(CH3)2 LA4774 H RB1 RB1 Si(CH3)2 LA4775 H RB3 RB1 Si(CH3)2 LA4776 H RB4 RB1 Si(CH3)2 LA4777 H RB7 RB1 Si(CH3)2 LA4778 H RB10 RB1 Si(CH3)2 LA4779 H RA3 RB1 Si(CH3)2 LA4780 H RA34 RB1 Si(CH3)2,
wherein RB1 to RB23 have the following structures: - and
wherein RA1 to RA52 have the following structures: - In some embodiments, the compound has a formula of M(LA)x(LB)y(LC)z where LB and LC are each a bidentate ligand; x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.
- In some embodiments, the compound has a formula selected from the group consisting of Ir(LA)3, Ir(LA)(LB)2, Ir(LA)2(LB), Ir(LA)2(LC), and Ir(LA)(LB)(LC); and ligands LA, LB, and LC are different from each other.
- In some embodiments, the compound has a formula of Pt(LA)(LB), where LA and LB can be the same or different. In some such embodiments, LA and LB are connected to form a tetradentate ligand. In some such embodiments, LA and LB are connected at two places to form a macrocyclic tetradentate ligand.
- In some embodiments where the compound has the formula M(LA)x(LB)y(LC)z, ligands LB and LC are each independently selected from the group consisting of
- where:
- each Y1 to Y13 is independently selected from the group consisting of carbon and nitrogen;
- X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S=0, SO2, CR1R2, SiR1R2, and GeR1R2;
- R1 and R2 are optionally fused or joined to form a ring;
- each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
- R1, R2, Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
- any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.
- In some such embodiments where the compound has the formula M(LA)x(LB)y(LC)z, ligands LB and LC are each independently selected from the group consisting of
- In some embodiments, the compound is Compound Ax having the formula Ir(LAi)3; where x=i; i is an integer from 1 to 4780, and LA1 to LA4780 are defined as set forth above.
- In some embodiments, the compound is Compound By having the formula Ir(LAi)(LBk)2; where y=468i+k-468; i is an integer from 1 to 4780, and k is an integer from 1 to 468; and ligand LBk has the following structures
- In some embodiments, the compound is the Compound Cz having the formula Ir(LAi)2(LC,); where z=1260i+j-1260; i is an integer from 1 to 4780; j is an integer from 1 to 1260; and ligand LC is selected from the group consisting of the following structures:
- LC1 through LC1260 are based on a structure of Formula X,
- in which R1, R2, and R3 are defined as:
-
Ligand R1 R2 R3 LC1 RD1 RD1 H LC2 RD2 RD2 H LC3 RD3 RD3 H LC4 RD4 RD4 H LC5 RD5 RD5 H LC6 RD6 RD6 H LC7 RD7 RD7 H LC8 RD8 RD8 H LC9 RD9 RD9 H LC10 RD10 RD10 H LC11 RD11 RD11 H LC12 RD12 RD12 H LC13 RD13 RD13 H LC14 RD14 RD14 H LC15 RD15 RD15 H LC16 RD16 RD16 H LC17 RD17 RD17 H LC18 RD18 RD18 H LC19 RD19 RD19 H LC20 RD20 RD20 H LC21 RD21 RD21 H LC22 RD22 RD22 H LC23 RD23 RD23 H LC24 RD24 RD24 H LC25 RD25 RD25 H LC26 RD26 RD26 H LC27 RD27 RD27 H LC28 RD28 RD28 H LC29 RD29 RD29 H LC30 RD30 RD30 H LC31 RD31 RD31 H LC32 RD32 RD32 H LC33 RD33 RD33 H LC34 RD34 RD34 H LC35 RD35 RD35 H LC36 RD40 RD40 H LC37 RD41 RD41 H LC38 RD42 RD42 H LC39 RD64 RD64 H LC40 RD66 RD66 H LC41 RD68 RD68 H LC42 RD76 RD76 H LC43 RD1 RD2 H LC44 RD1 RD3 H LC45 RD1 RD4 H LC46 RD1 RD5 H LC47 RD1 RD6 H LC48 RD1 RD7 H LC49 RD1 RD8 H LC50 RD1 RD9 H LC51 RD1 RD10 H LC52 RD1 RD11 H LC53 RD1 RD12 H LC54 RD1 RD13 H LC55 RD1 RD14 H LC56 RD1 RD15 H LC57 RD1 RD16 H LC58 RD1 RD17 H LC59 RD1 RD18 H LC60 RD1 RD19 H LC61 RD1 RD20 H LC62 RD1 RD21 H LC63 RD1 RD22 H LC64 RD1 RD23 H LC65 RD1 RD24 H LC66 RD1 RD25 H LC67 RD1 RD26 H LC68 RD1 RD27 H LC69 RD1 RD28 H LC70 RD1 RD29 H LC71 RD1 RD30 H LC72 RD1 RD31 H LC73 RD1 RD32 H LC74 RD1 RD33 H LC75 RD1 RD34 H LC76 RD1 RD35 H LC77 RD1 RD40 H LC78 RD1 RD41 H LC79 RD1 RD42 H LC80 RD1 RD64 H LC81 RD1 RD66 H LC82 RD1 RD68 H LC83 RD1 RD76 H LC84 RD2 RD1 H LC85 RD2 RD3 H LC86 RD2 RD4 H LC87 RD2 RD5 H LC88 RD2 RD6 H LC89 RD2 RD7 H LC90 RD2 RD8 H LC91 RD2 RD9 H LC92 RD2 RD10 H LC93 RD2 RD11 H LC94 RD2 RD12 H LC95 RD2 RD13 H LC96 RD2 RD14 H LC97 RD2 RD15 H LC98 RD2 RD16 H LC99 RD2 RD17 H LC100 RD2 RD18 H LC101 RD2 RD19 H LC102 RD2 RD20 H LC103 RD2 RD21 H LC104 RD2 RD22 H LC105 RD2 RD23 H LC106 RD2 RD24 H LC107 RD2 RD25 H LC108 RD2 RD26 H LC109 RD2 RD27 H LC110 RD2 RD28 H LC111 RD2 RD29 H LC112 RD2 RD30 H LC113 RD2 RD31 H LC114 RD2 RD32 H LC115 RD2 RD33 H LC116 RD2 RD34 H LC117 RD2 RD35 H LC118 RD2 RD40 H LC119 RD2 RD41 H LC120 RD2 RD42 H LC121 RD2 RD64 H LC122 RD2 RD66 H LC123 RD2 RD68 H LC124 RD2 RD76 H LC125 RD3 RD4 H LC126 RD3 RD5 H LC127 RD3 RD6 H LC128 RD3 RD7 H LC129 RD3 RD8 H LC130 RD3 RD9 H LC131 RD3 RD10 H LC132 RD3 RD11 H LC133 RD3 RD12 H LC134 RD3 RD13 H LC135 RD3 RD14 H LC136 RD3 RD15 H LC137 RD3 RD16 H LC138 RD3 RD17 H LC139 RD3 RD18 H LC140 RD3 RD19 H LC141 RD3 RD20 H LC142 RD3 RD21 H LC143 RD3 RD22 H LC144 RD3 RD23 H LC145 RD3 RD24 H LC146 RD3 RD25 H LC147 RD3 RD26 H LC148 RD3 RD27 H LC149 RD3 RD28 H LC150 RD3 RD29 H LC151 RD3 RD30 H LC152 RD3 RD31 H LC153 RD3 RD32 H LC154 RD3 RD33 H LC155 RD3 RD34 H LC156 RD3 RD35 H LC157 RD3 RD40 H LC158 RD3 RD41 H LC159 RD3 RD42 H LC160 RD3 RD64 H LC161 RD3 RD66 H LC162 RD3 RD68 H LC163 RD3 RD76 H LC164 RD4 RD5 H LC165 RD4 RD6 H LC166 RD4 RD7 H LC167 RD4 RD8 H LC168 RD4 RD9 H LC169 RD4 RD10 H LC170 RD4 RD11 H LC171 RD4 RD12 H LC172 RD4 RD13 H LC173 RD4 RD14 H LC174 RD4 RD15 H LC175 RD4 RD16 H LD176 RD4 RD17 H LC177 RD4 RD18 H LC178 RD4 RD19 H LC179 RD4 RD20 H LC180 RD4 RD21 H LC181 RD4 RD22 H LC182 RD4 RD23 H LC183 RD4 RD24 H LC184 RD4 RD25 H LC185 RD4 RD26 H LC186 RD4 RD27 H LC187 RD4 RD28 H LC188 RD4 RD29 H LC189 RD4 RD30 H LC190 RD4 RD31 H LC191 RD4 RD32 H LC192 RD4 RD33 H LC193 RD4 RD34 H LC194 RD4 RD35 H LC195 RD4 RD40 H LC196 RD4 RD41 H LC197 RD4 RD42 H LC198 RD4 RD64 H LC199 RD4 RD66 H LC200 RD4 RD68 H LC201 RD4 RD76 H LC202 RD4 RD1 H LC203 RD7 RD5 H LC204 RD7 RD6 H LC205 RD7 RD8 H LC206 RD7 RD9 H LC207 RD7 RD10 H LC208 RD7 RD11 H LC209 RD7 RD12 H LC210 RD7 RD13 H LC211 RD7 RD14 H LC212 RD7 RD15 H LC213 RD7 RD16 H LC214 RD7 RD17 H LC215 RD7 RD18 H LC216 RD7 RD19 H LC217 RD7 RD20 H LC218 RD7 RD21 H LC219 RD7 RD22 H LC220 RD7 RD23 H LC221 RD7 RD24 H LC222 RD7 RD25 H LC223 RD7 RD26 H LC224 RD7 RD27 H LC225 RD7 RD28 H LC226 RD7 RD29 H LC227 RD7 RD30 H LC228 RD7 RD31 H LC229 RD7 RD32 H LC230 RD7 RD33 H LC231 RD7 RD34 H LC232 RD7 RD35 H LC233 RD7 RD40 H LC234 RD7 RD41 H LC235 RD7 RD42 H LC236 RD7 RD64 H LC237 RD7 RD66 H LC238 RD7 RD68 H LC239 RD7 RD76 H LC240 RD8 RD5 H LC241 RD8 RD6 H LC242 RD8 RD9 H LC243 RD8 RD10 H LC244 RD8 RD11 H LC245 RD8 RD12 H LC246 RD8 RD13 H LC247 RD8 RD14 H LC248 RD8 RD15 H LC249 RD8 RD16 H LC250 RD8 RD17 H LC251 RD8 RD18 H LC252 RD8 RD19 H LC253 RD8 RD20 H LC254 RD8 RD21 H LC255 RD8 RD22 H LC256 RD8 RD23 H LC257 RD8 RD24 H LC258 RD8 RD25 H LC259 RD8 RD26 H LC260 RD8 RD27 H LC261 RD8 RD28 H LC262 RD8 RD29 H LC263 RD8 RD30 H LC264 RD8 RD31 H LC265 RD8 RD32 H LC266 RD8 RD33 H LC267 RD8 RD34 H LC268 RD8 RD35 H LC269 RD8 RD40 H LC270 RD8 RD41 H LC271 RD8 RD42 H LC272 RD8 RD64 H LC273 RD8 RD66 H LC274 RD8 RD68 H LC275 RD8 RD76 H LC276 RD11 RD5 H LC277 RD11 RD6 H LC278 RD11 RD9 H LC279 RD11 RD10 H LC280 RD11 RD12 H LC281 RD11 RD13 H LC282 RD11 RD14 H LC283 RD11 RD15 H LC284 RD11 RD16 H LC285 RD11 RD17 H LC286 RD11 RD18 H LC287 RD11 RD19 H LC288 RD11 RD20 H LC289 RD11 RD21 H LC290 RD11 RD22 H LC291 RD11 RD23 H LC292 RD11 RD24 H LC293 RD11 RD25 H LC294 RD11 RD26 H LC295 RD11 RD27 H LC296 RD11 RD28 H LC297 RD11 RD29 H LC298 RD11 RD30 H LC299 RD11 RD31 H LC300 RD11 RD32 H LC301 RD11 RD33 H LC302 RD11 RD34 H LC303 RD11 RD35 H LC304 RD11 RD40 H LC305 RD11 RD41 H LC306 RD11 RD42 H LC307 RD11 RD64 H LC308 RD11 RD66 H LC309 RD11 RD68 H LC310 RD11 RD76 H LC311 RD13 RD5 H LC312 RD13 RD6 H LC313 RD13 RD9 H LC314 RD13 RD10 H LC315 RD13 RD12 H LC316 RD13 RD14 H LC317 RD13 RD15 H LC318 RD13 RD16 H LC319 RD13 RD17 H LC320 RD13 RD18 H LC321 RD13 RD19 H LC322 RD13 RD20 H LC323 RD13 RD21 H LC324 RD13 RD22 H LC325 RD13 RD23 H LC326 RD13 RD24 H LC327 RD13 RD25 H LC328 RD13 RD26 H LC329 RD13 RD27 H LC330 RD13 RD28 H LC331 RD13 RD29 H LC332 RD13 RD30 H LC333 RD13 RD31 H LC334 RD13 RD32 H LC335 RD13 RD33 H LC336 RD13 RD34 H LC337 RD13 RD35 H LC338 RD13 RD40 H LC339 RD13 RD41 H LC340 RD13 RD42 H LC341 RD13 RD64 H LC342 RD13 RD66 H LC343 RD13 RD68 H LC344 RD13 RD76 H LC345 RD14 RD5 H LC346 RD14 RD6 H LC347 RD14 RD9 H LC348 RD14 RD10 H LC349 RD14 RD12 H LC350 RD14 RD15 H LC351 RD14 RD16 H LC352 RD14 RD17 H LC353 RD14 RD18 H LC354 RD14 RD19 H LC355 RD14 RD20 H LC356 RD14 RD21 H LC357 RD14 RD22 H LC358 RD14 RD23 H LC359 RD14 RD24 H LC360 RD14 RD25 H LC361 RD14 RD26 H LC362 RD14 RD27 H LC363 RD14 RD28 H LC364 RD14 RD29 H LC365 RD14 RD30 H LC366 RD14 RD31 H LC367 RD14 RD32 H LC368 RD14 RD33 H LC369 RD14 RD34 H LC370 RD14 RD35 H LC371 RD14 RD40 H LC372 RD14 RD41 H LC373 RD14 RD42 H LC374 RD14 RD64 H LC375 RD14 RD66 H LC376 RD14 RD68 H LC377 RD14 RD76 H LC378 RD22 RD5 H LC379 RD22 RD6 H LC380 RD22 RD9 H LC381 RD22 RD10 H LC382 RD22 RD12 H LC383 RD22 RD15 H LC384 RD22 RD16 H LC385 RD22 RD17 H LC386 RD22 RD18 H LC387 RD22 RD19 H LC388 RD22 RD20 H LC389 RD22 RD21 H LC390 RD22 RD23 H LC391 RD22 RD24 H LC392 RD22 RD25 H LC393 RD22 RD26 H LC394 RD22 RD27 H LC395 RD22 RD28 H LC396 RD22 RD29 H LC397 RD22 RD30 H LC398 RD22 RD31 H LC399 RD22 RD32 H LC400 RD22 RD33 H LC401 RD22 RD34 H LC402 RD22 RD35 H LC403 RD22 RD40 H LC404 RD22 RD41 H LC405 RD22 RD42 H LC406 RD22 RD64 H LC407 RD22 RD66 H LC408 RD22 RD68 H LC409 RD22 RD76 H LC410 RD26 RD5 H LC411 RD26 RD6 H LC412 RD26 RD9 H LC413 RD26 RD10 H LC414 RD26 RD12 H LC415 RD26 RD15 H LC416 RD26 RD16 H LC417 RD26 RD17 H LC418 RD26 RD18 H LC419 RD26 RD19 H LC420 RD26 RD20 H LC421 RD26 RD21 H LC422 RD26 RD23 H LC423 RD26 RD24 H LC424 RD26 RD25 H LC425 RD26 RD27 H LC426 RD26 RD28 H LC427 RD26 RD29 H LC428 RD26 RD30 H LC429 RD26 RD31 H LC430 RD26 RD32 H LC431 RD26 RD33 H LC432 RD26 RD34 H LC433 RD26 RD35 H LC434 RD26 RD40 H LC435 RD26 RD41 H LC436 RD26 RD42 H LC437 RD26 RD64 H LC438 RD26 RD66 H LC439 RD26 RD68 H LC440 RD26 RD76 H LC441 RD35 RD5 H LC442 RD35 RD6 H LC443 RD35 RD9 H LC444 RD35 RD10 H LC445 RD35 RD12 H LC446 RD35 RD15 H LC447 RD35 RD16 H LC448 RD35 RD17 H LC449 RD35 RD18 H LC450 RD35 RD19 H LC451 RD35 RD20 H LC452 RD35 RD21 H LC453 RD35 RD23 H LC454 RD35 RD24 H LC455 RD35 RD25 H LC456 RD35 RD27 H LC457 RD35 RD28 H LC458 RD35 RD29 H LC459 RD35 RD30 H LC460 RD35 RD31 H LC461 RD35 RD32 H LC462 RD35 RD33 H LC463 RD35 RD34 H LC464 RD35 RD40 H LC465 RD35 RD41 H LC466 RD35 RD42 H LC467 RD35 RD64 H LC468 RD35 RD66 H LC469 RD35 RD68 H LC470 RD35 RD76 H LC471 RD40 RD5 H LC472 RD40 RD6 H LC473 RD40 RD9 H LC474 RD40 RD10 H LC475 RD40 RD12 H LC476 RD40 RD15 H LC477 RD40 RD16 H LC478 RD40 RD17 H LC479 RD40 RD18 H LC480 RD40 RD19 H LC481 RD40 RD20 H LC482 RD40 RD21 H LC483 RD40 RD23 H LC484 RD40 RD24 H LC485 RD40 RD25 H LC486 RD40 RD27 H LC487 RD40 RD28 H LC488 RD40 RD29 H LC489 RD40 RD30 H LC490 RD40 RD31 H LC491 RD40 RD32 H LC492 RD40 RD33 H LC493 RD40 RD34 H LC494 RD40 RD41 H LC495 RD40 RD42 H LC496 RD40 RD64 H LC497 RD40 RD66 H LC498 RD40 RD68 H LC499 RD40 RD76 H LC500 RD41 RD5 H LC501 RD41 RD6 H LC502 RD41 RD9 H LC503 RD41 RD10 H LC504 RD41 RD12 H LC505 RD41 RD15 H LC506 RD41 RD16 H LC507 RD41 RD17 H LC508 RD41 RD18 H LC509 RD41 RD19 H LC510 RD41 RD20 H LC511 RD41 RD21 H LC512 RD41 RD23 H LC513 RD41 RD24 H LC514 RD41 RD25 H LC515 RD41 RD27 H LC516 RD41 RD28 H LC517 RD41 RD29 H LC518 RD41 RD30 H LC519 RD41 RD31 H LC520 RD41 RD32 H LC521 RD41 RD33 H LC522 RD41 RD34 H LC523 RD41 RD42 H LC524 RD41 RD64 H LC525 RD41 RD66 H LC526 RD41 RD68 H LC527 RD41 RD76 H LC528 RD64 RD5 H LC529 RD64 RD6 H LC530 RD64 RD9 H LC531 RD64 RD10 H LC532 RD64 RD12 H LC533 RD64 RD15 H LC534 RD64 RD16 H LC535 RD64 RD17 H LC536 RD64 RD18 H LC537 RD64 RD19 H LC538 RD64 RD20 H LC539 RD64 RD21 H LC540 RD64 RD23 H LC541 RD64 RD24 H LC542 RD64 RD25 H LC543 RD64 RD27 H LC544 RD64 RD28 H LC545 RD64 RD29 H LC546 RD64 RD30 H LC547 RD64 RD31 H LC548 RD64 RD32 H LC549 RD64 RD33 H LC550 RD54 RD34 H LC551 RD64 RD42 H LC552 RD64 RD64 H LC553 RD64 RD66 H LC554 RD64 RD68 H LC555 RD64 RD76 H LC556 RD66 RD5 H LC557 RD66 RD6 H LC558 RD66 RD9 H LC559 RD66 RD10 H LC560 RD66 RD12 H LC561 RD66 RD15 H LC562 RD66 RD16 H LC563 RD66 RD17 H LC564 RD66 RD18 H LC565 RD66 RD19 H LC566 RD66 RD20 H LC567 RD66 RD21 H LC568 RD66 RD23 H LC569 RD66 RD24 H LC570 RD66 RD25 H LC571 RD66 RD27 H LC572 RD66 RD28 H LC573 RD66 RD29 H LC574 RD66 RD30 H LC575 RD66 RD31 H LC576 RD66 RD32 H LC577 RD66 RD33 H LC578 RD66 RD34 H LC579 RD66 RD42 H LC580 RD66 RD68 H LC581 RD66 RD76 H LC582 RD68 RD5 H LC583 RD68 RD6 H LC584 RD68 RD9 H LC585 RD68 RD10 H LC586 RD68 RD12 H LC587 RD68 RD15 H LC588 RD68 RD16 H LC589 RD68 RD17 H LC590 RD68 RD18 H LC591 RD68 RD19 H LC592 RD68 RD20 H LC593 RD68 RD21 H LC594 RD68 RD23 H LC595 RD68 RD24 H LC596 RD68 RD25 H LC597 RD68 RD27 H LC598 RD68 RD28 H LC599 RD68 RD29 H LC600 RD68 RD30 H LC601 RD68 RD31 H LC602 RD68 RD32 H LC603 RD68 RD33 H LC604 RD68 RD34 H LC605 RD68 RD42 H LC606 RD68 RD76 H LC607 RD76 RD5 H LC608 RD76 RD6 H LC609 RD76 RD9 H LC610 RD76 RD10 H LC611 RD76 RD12 H LC612 RD76 RD15 H LC613 RD76 RD16 H LC614 RD76 RD17 H LC615 RD76 RD18 H LC616 RD76 RD19 H LC617 RD76 RD20 H LC618 RD76 RD21 H LC619 RD76 RD23 H LC620 RD76 RD24 H LC621 RD76 RD25 H LC622 RD76 RD27 H LC623 RD76 RD28 H LC624 RD76 RD29 H LC625 RD76 RD30 H LC626 RD76 RD31 H LC627 RD76 RD32 H LC628 RD76 RD33 H LC629 RD76 RD34 H LC630 RD76 RD42 H LC631 RD1 RD1 RD1 LC632 RD2 RD2 RD1 LC633 RD3 RD3 RD1 LC634 RD4 RD4 RD1 LC635 RD5 RD5 RD1 LC636 RD6 RD6 RD1 LC637 RD7 RD7 RD1 LC638 RD8 RD8 RD1 LC639 RD9 RD9 RD1 LC640 RD10 RD10 RD1 LC641 RD11 RD11 RD1 LC642 RD12 RD12 RD1 LC643 RD13 RD13 RD1 LC644 RD14 RD14 RD1 LC645 RD15 RD15 RD1 LC646 RD16 RD16 RD1 LC647 RD17 RD17 RD1 LC648 RD18 RD18 RD1 LC649 RD19 RD19 RD1 LC650 RD20 RD20 RD1 LC651 RD21 RD21 RD1 LC652 RD22 RD22 RD1 LC653 RD23 RD23 RD1 LC654 RD24 RD24 RD1 LC655 RD25 RD25 RD1 LC656 RD26 RD26 RD1 LC657 RD27 RD27 RD1 LC658 RD28 RD28 RD1 LC659 RD29 RD29 RD1 LC660 RD30 RD30 RD1 LC661 RD31 RD31 RD1 LC662 RD32 RD32 RD1 LC663 RD33 RD33 RD1 LC664 RD34 RD34 RD1 LC665 RD35 RD35 RD1 LC666 RD40 RD40 RD1 LC667 RD41 RD41 RD1 LC668 RD42 RD42 RD1 LC669 RD64 RD64 RD1 LC670 RD66 RD66 RD1 LC671 RD68 RD68 RD1 LC672 RD76 RD76 RD1 LC673 RD1 RD2 RD1 LC674 RD1 RD3 RD1 LC675 RD1 RD4 RD1 LC676 RD1 RD5 RD1 LC677 RD1 RD6 RD1 LC678 RD1 RD7 RD1 LC679 RD1 RD8 RD1 LC680 RD1 RD9 RD1 LC681 RD1 RD10 RD1 LC682 RD1 RD11 RD1 LC683 RD1 RD12 RD1 LC684 RD1 RD13 RD1 LC685 RD1 RD14 RD1 LC686 RD1 RD15 RD1 LC687 RD1 RD16 RD1 LC688 RD1 RD17 RD1 LC689 RD1 RD18 RD1 LC690 RD1 RD19 RD1 LC691 RD1 RD20 RD1 LC692 RD1 RD21 RD1 LC693 RD1 RD22 RD1 LC694 RD1 RD23 RD1 LC695 RD1 RD24 RD1 LC696 RD1 RD25 RD1 LC697 RD1 RD26 RD1 LC698 RD1 RD27 RD1 LC699 RD1 RD28 RD1 L1700 RD1 RD29 RD1 LC701 RD1 RD30 RD1 LC702 RD1 RD31 RD1 LC703 RD1 RD32 RD1 LC704 RD1 RD33 RD1 LC705 RD1 RD34 RD1 LC706 RD1 RD35 RD1 LC707 RD1 RD40 RD1 LC708 RD1 RD41 RD1 LC709 RD1 RD42 RD1 LC710 RD1 RD64 RD1 LC711 RD1 RD66 RD1 LC712 RD1 RD68 RD1 LC713 RD1 RD76 RD1 LC714 RD2 RD1 RD1 LC715 RD2 RD3 RD1 LC716 RD2 RD4 RD1 LC717 RD2 RD5 RD1 LC718 RD2 RD6 RD1 LC719 RD2 RD7 RD1 LC720 RD2 RD8 RD1 LC721 RD2 RD9 RD1 LC722 RD2 RD10 RD1 LC723 RD2 RD11 RD1 LC724 RD2 RD12 RD1 LC725 RD2 RD13 RD1 LC726 RD2 RD14 RD1 LC727 RD2 RD15 RD1 LC728 RD2 RD16 RD1 LC729 RD2 RD17 RD1 LC730 RD2 RD18 RD1 LC731 RD2 RD19 RD1 LC732 RD2 RD20 RD1 LC733 RD2 RD21 RD1 LC734 RD2 RD22 RD1 LC735 RD2 RD23 RD1 LC736 RD2 RD24 RD1 LC737 RD2 RD25 RD1 LC738 RD2 RD26 RD1 LC739 RD2 RD27 RD1 LC740 RD2 RD28 RD1 LC741 RD2 RD29 RD1 LC742 RD2 RD30 RD1 LC743 RD2 RD31 RD1 LC744 RD2 RD32 RD1 LC745 RD2 RD33 RD1 LC746 RD2 RD34 RD1 LC747 RD2 RD35 RD1 LC748 RD2 RD40 RD1 LC749 RD2 RD41 RD1 LC750 RD2 RD42 RD1 LC751 RD2 RD64 RD1 LC752 RD2 RD66 RD1 LC753 RD2 RD68 RD1 LC754 RD2 RD76 RD1 LC755 RD3 RD4 RD1 LC756 RD3 RD5 RD1 LC757 RD3 RD6 RD1 LC758 RD3 RD7 RD1 LC759 RD3 RD8 RD1 LC760 RD3 RD9 RD1 LC761 RD3 RD10 RD1 LC762 RD3 RD11 RD1 LC763 RD3 RD12 RD1 LC764 RD3 RD13 RD1 LC765 RD3 RD14 RD1 LC766 RD3 RD15 RD1 LC767 RD3 RD16 RD1 LC768 RD3 RD17 RD1 LC769 RD3 RD18 RD1 LC770 RD3 RD19 RD1 LC771 RD3 RD20 RD1 LC772 RD3 RD21 RD1 LC773 RD3 RD22 RD1 LC774 RD3 RD23 RD1 LC775 RD3 RD24 RD1 LC776 RD3 RD25 RD1 LC777 RD3 RD26 RD1 LC778 RD3 RD27 RD1 LC779 RD3 RD28 RD1 LC780 RD3 RD29 RD1 LC781 RD3 RD30 RD1 LC782 RD3 RD31 RD1 LC783 RD3 RD32 RD1 LC784 RD3 RD33 RD1 LC785 RD3 RD34 RD1 LC786 RD3 RD35 RD1 LC787 RD3 RD40 RD1 LC788 RD3 RD41 RD1 LC789 RD3 RD42 RD1 LC790 RD3 RD64 RD1 LC791 RD3 RD66 RD1 LC792 RD3 RD68 RD1 LC793 RD3 RD76 RD1 LC794 RD4 RD5 RD1 LC795 RD4 RD6 RD1 LC796 RD4 RD7 RD1 LC797 RD4 RD8 RD1 LC798 RD4 RD9 RD1 LC799 RD4 RD10 RD1 LC800 RD4 RD11 RD1 LC801 RD4 RD12 RD1 LC802 RD4 RD13 RD1 LC803 RD4 RD14 RD1 LC804 RD4 RD15 RD1 LC805 RD4 RD16 RD1 LC806 RD4 RD17 RD1 LC807 RD4 RD18 RD1 LC808 RD4 RD19 RD1 LC809 RD4 RD20 RD1 LC810 RD4 RD21 RD1 LC811 RD4 RD22 RD1 LC812 RD4 RD23 RD1 LC813 RD4 RD24 RD1 LC814 RD4 RD25 RD1 LC815 RD4 RD26 RD1 LC816 RD4 RD27 RD1 LC817 RD4 RD28 RD1 LC818 RD4 RD29 RD1 LC819 RD4 RD30 RD1 LC820 RD4 RD31 RD1 LC821 RD4 RD32 RD1 LC822 RD4 RD33 RD1 LC823 RD4 RD34 RD1 LC824 RD4 RD35 RD1 LC825 RD4 RD40 RD1 LC826 RD4 RD41 RD1 LC827 RD4 RD42 RD1 LC828 RD4 RD64 RD1 LC829 RD4 RD66 RD1 LC830 RD4 RD68 RD1 LC831 RD4 RD76 RD1 LC832 RD4 RD1 RD1 LC833 RD7 RD5 RD1 LC834 RD7 RD6 RD1 LC835 RD7 RD8 RD1 LC836 RD7 RD9 RD1 LC837 RD7 RD10 RD1 LC838 RD7 RD11 RD1 LC839 RD7 RD12 RD1 LC840 RD7 RD13 RD1 LC841 RD7 RD14 RD1 LC842 RD7 RD15 RD1 LC843 RD7 RD16 RD1 LC844 RD7 RD17 RD1 LC845 RD7 RD18 RD1 LC846 RD7 RD19 RD1 LC847 RD7 RD20 RD1 LC848 RD7 RD21 RD1 LC849 RD7 RD22 RD1 LC850 RD7 RD23 RD1 LC851 RD7 RD24 RD1 LC852 RD7 RD25 RD1 LC853 RD7 RD26 RD1 LC854 RD7 RD27 RD1 LC855 RD7 RD28 RD1 LC856 RD7 RD29 RD1 LC857 RD7 RD30 RD1 LC858 RD7 RD31 RD1 LC859 RD7 RD32 RD1 LC860 RD7 RD33 RD1 LC861 RD7 RD34 RD1 LC862 RD7 RD35 RD1 LC863 RD7 RD40 RD1 LC864 RD7 RD41 RD1 LC865 RD7 RD42 RD1 LC866 RD7 RD64 RD1 LC867 RD7 RD66 RD1 LC868 RD7 RD68 RD1 LC869 RD7 RD76 RD1 LC870 RD8 RD5 RD1 LC871 RD8 RD6 RD1 LC872 RD8 RD9 RD1 LC873 RD8 RD10 RD1 LC874 RD8 RD11 RD1 LC875 RD8 RD12 RD1 LC876 RD8 RD13 RD1 LC877 RD8 RD14 RD1 LC878 RD8 RD15 RD1 LC879 RD8 RD16 RD1 LC880 RD8 RD17 RD1 LC881 RD8 RD18 RD1 LC882 RD8 RD19 RD1 LC883 RD8 RD20 RD1 LC884 RD8 RD21 RD1 LC885 RD8 RD22 RD1 LC886 RD8 RD23 RD1 LC887 RD8 RD24 RD1 LC888 RD8 RD25 RD1 LC889 RD8 RD26 RD1 LC890 RD8 RD27 RD1 LC891 RD8 RD28 RD1 LC892 RD8 RD29 RD1 LC893 RD8 RD30 RD1 LC894 RD8 RD31 RD1 LC895 RD8 RD32 RD1 LC896 RD8 RD33 RD1 LC897 RD8 RD34 RD1 LC898 RD8 RD35 RD1 LC899 RD8 RD40 RD1 LC900 RD8 RD41 RD1 LC901 RD8 RD42 RD1 LC902 RD8 RD64 RD1 LC903 RD8 RD66 RD1 LC904 RD8 RD68 RD1 LC905 RD8 RD76 RD1 LC906 RD11 RD5 RD1 LC907 RD11 RD6 RD1 LC908 RD11 RD9 RD1 LC909 RD11 RD10 RD1 LC910 RD11 RD12 RD1 LC911 RD11 RD13 RD1 LC912 RD11 RD14 RD1 LC913 RD11 RD15 RD1 LC914 RD11 RD16 RD1 LC915 RD11 RD17 RD1 LC916 RD11 RD18 RD1 LC917 RD11 RD19 RD1 LC918 RD11 RD20 RD1 LC919 RD11 RD21 RD1 LC920 RD11 RD22 RD1 LC921 RD11 RD23 RD1 LC922 RD11 RD24 RD1 LC923 RD11 RD25 RD1 LC924 RD11 RD26 RD1 LC925 RD11 RD27 RD1 LC926 RD11 RD28 RD1 LC927 RD11 RD29 RD1 LC928 RD11 RD30 RD1 LC929 RD11 RD31 RD1 LC930 RD11 RD32 RD1 LC931 RD11 RD33 RD1 LC932 RD11 RD34 RD1 LC933 RD11 RD35 RD1 LC934 RD11 RD40 RD1 LC935 RD11 RD41 RD1 LC936 RD11 RD42 RD1 LC937 RD11 RD64 RD1 LC938 RD11 RD66 RD1 LC939 RD11 RD68 RD1 LC940 RD11 RD76 RD1 LC941 RD13 RD5 RD1 LC942 RD13 RD6 RD1 LC943 RD13 RD9 RD1 LC944 RD13 RD10 RD1 LC945 RD13 RD12 RD1 LC946 RD13 RD14 RD1 LC947 RD13 RD15 RD1 LC948 RD13 RD16 RD1 LC949 RD13 RD17 RD1 LC950 RD13 RD18 RD1 LC951 RD13 RD19 RD1 LC952 RD13 RD20 RD1 LC953 RD13 RD21 RD1 LC954 RD13 RD22 RD1 LC955 RD13 RD23 RD1 LC956 RD13 RD24 RD1 LC957 RD13 RD25 RD1 LC958 RD13 RD26 RD1 LC959 RD13 RD27 RD1 LC960 RD13 RD28 RD1 LC961 RD13 RD29 RD1 LC962 RD13 RD30 RD1 LC963 RD13 RD31 RD1 LC964 RD13 RD32 RD1 LC965 RD13 RD33 RD1 LC966 RD13 RD34 RD1 LC967 RD13 RD35 RD1 LC968 RD13 RD40 RD1 LC969 RD13 RD41 RD1 LC970 RD13 RD42 RD1 LC971 RD13 RD64 RD1 LC972 RD13 RD66 RD1 LC973 RD13 RD68 RD1 LC974 RD13 RD76 RD1 LC975 RD14 RD5 RD1 LC976 RD14 RD6 RD1 LC977 RD14 RD9 RD1 LC978 RD14 RD10 RD1 LC979 RD14 RD12 RD1 LC980 RD14 RD15 RD1 LC981 RD14 RD11 RD1 LC982 RD14 RD17 RD1 LC983 RD14 RD18 RD1 LC984 RD14 RD19 RD1 LC985 RD14 RD20 RD1 LC986 RD14 RD21 RD1 LC987 RD14 RD22 RD1 LC988 RD14 RD23 RD1 LC989 RD14 RD24 RD1 LC990 RD14 RD25 RD1 LC991 RD14 RD26 RD1 LC992 RD14 RD27 RD1 LC993 RD14 RD28 RD1 LC994 RD14 RD29 RD1 LC995 RD14 RD30 RD1 LC996 RD14 RD31 RD1 LC997 RD14 RD32 RD1 LC998 RD14 RD33 RD1 LC999 RD14 RD34 RD1 LC1000 RD14 RD35 RD1 LC1001 RD14 RD40 RD1 LC1002 RD14 RD41 RD1 LC1003 RD14 RD42 RD1 LC1004 RD14 RD64 RD1 LC1005 RD14 RD66 RD1 LC1006 RD14 RD68 RD1 LC1007 RD14 RD76 RD1 LC1008 RD22 RD5 RD1 LC1009 RD22 RD6 RD1 LC1010 RD22 RD9 RD1 LC1011 RD22 RD10 RD1 LC1012 RD22 RD12 RD1 LC1013 RD22 RD15 RD1 LC1014 RD22 RD16 RD1 LC1015 RD22 RD17 RD1 LC1016 RD22 RD18 RD1 LC1017 RD22 RD19 RD1 LC1018 RD22 RD20 RD1 LC1019 RD22 RD21 RD1 LC1020 RD22 RD23 RD1 LC1021 RD22 RD24 RD1 LC1022 RD22 RD25 RD1 LC1023 RD22 RD26 RD1 LC1024 RD22 RD27 RD1 LC1025 RD22 RD28 RD1 LC1026 RD22 RD29 RD1 LC1027 RD22 RD30 RD1 LC1028 RD22 RD31 RD1 LC1029 RD22 RD32 RD1 LC1030 RD22 RD33 RD1 LC1031 RD22 RD34 RD1 LC1032 RD22 RD35 RD1 LC1033 RD22 RD40 RD1 LC1034 RD22 RD41 RD1 LC1035 RD22 RD42 RD1 LC1036 RD22 RD64 RD1 LC1037 RD22 RD66 RD1 LC1038 RD22 RD68 RD1 LC1039 RD22 RD76 RD1 LC1040 RD26 RD5 RD1 LC1041 RD26 RD6 RD1 LC1042 RD26 RD9 RD1 LC1043 RD26 RD10 RD1 LC1044 RD26 RD12 RD1 LC1045 RD26 RD15 RD1 LC1046 RD26 RD16 RD1 LC1047 RD26 RD17 RD1 LC1048 RD26 RD18 RD1 LC1049 RD26 RD19 RD1 LC1050 RD26 RD20 RD1 LC1051 RD26 RD21 RD1 LC1052 RD26 RD23 RD1 LC1053 RD26 RD24 RD1 LC1054 RD26 RD25 RD1 LC1055 RD26 RD27 RD1 LC1056 RD26 RD28 RD1 LC1057 RD26 RD29 RD1 LC1058 RD26 RD30 RD1 LC1059 RD26 RD31 RD1 LC1060 RD26 RD32 RD1 LC1061 RD26 RD33 RD1 LC1062 RD26 RD34 RD1 LC1063 RD26 RD35 RD1 LC1064 RD26 RD40 RD1 LC1065 RD26 RD41 RD1 LC1066 RD26 RD42 RD1 LC1067 RD26 RD64 RD1 LC1068 RD26 RD66 RD1 LC1069 RD26 RD68 RD1 LC1070 RD26 RD76 RD1 LC1071 RD35 RD5 RD1 LC1072 RD35 RD6 RD1 LC1073 RD35 RD9 RD1 LC1074 RD35 RD10 RD1 LC1075 RD35 RD12 RD1 LC1076 RD35 RD15 RD1 LC1077 RD35 RD16 RD1 LC1078 RD35 RD17 RD1 LC1079 RD35 RD18 RD1 LC1080 RD35 RD19 RD1 LC1081 RD35 RD20 RD1 LC1082 RD35 RD21 RD1 LC1083 RD35 RD23 RD1 LC1084 RD35 RD24 RD1 LC1085 RD35 RD25 RD1 LC1086 RD35 RD27 RD1 LC1087 RD35 RD28 RD1 LC1088 RD35 RD29 RD1 LC1089 RD35 RD30 RD1 LC1090 RD35 RD31 RD1 LC1091 RD35 RD32 RD1 LC1092 RD35 RD33 RD1 LC1093 RD35 RD34 RD1 LC1094 RD35 RD40 RD1 LC1095 RD35 RD41 RD1 LC1096 RD35 RD42 RD1 LC1097 RD35 RD64 RD1 LC1098 RD35 RD66 RD1 LC1099 RD35 RD68 RD1 LC1100 RD35 RD76 RD1 LC1101 RD40 RD5 RD1 LC1102 RD40 RD6 RD1 LC1103 RD40 RD9 RD1 LC1104 RD40 RD10 RD1 LC1105 RD40 RD12 RD1 LC1106 RD40 RD15 RD1 LC1107 RD40 RD16 RD1 LC1108 RD40 RD17 RD1 LC1109 RD40 RD18 RD1 LC1110 RD40 RD19 RD1 LC1111 RD40 RD20 RD1 LC1112 RD40 RD21 RD1 LC1113 RD40 RD23 RD1 LC1114 RD40 RD24 RD1 LC1115 RD40 RD25 RD1 LC1116 RD40 RD27 RD1 LC1117 RD40 RD28 RD1 LC1118 RD40 RD29 RD1 LC1119 RD40 RD30 RD1 LC1120 RD40 RD31 RD1 LC1121 RD40 RD32 RD1 LC1122 RD40 RD33 RD1 LC1123 RD40 RD34 RD1 LC1124 RD40 RD41 RD1 LC1125 RD40 RD42 RD1 LC1126 RD40 RD64 RD1 LC1127 RD40 RD66 RD1 LC1128 RD40 RD68 RD1 LC1129 RD40 RD76 RD1 LC1130 RD41 RD5 RD1 LC1131 RD41 RD6 RD1 LC1132 RD41 RD9 RD1 LC1133 RD41 RD10 RD1 LC1134 RD41 RD12 RD1 LC1135 RD41 RD15 RD1 LC1136 RD41 RD16 RD1 LC1137 RD41 RD17 RD1 LC1138 RD41 RD18 RD1 LC1139 RD41 RD19 RD1 LC1140 RD41 RD20 RD1 LC1141 RD41 RD21 RD1 LC1142 RD41 RD23 RD1 LC1143 RD41 RD24 RD1 LC1144 RD41 RD25 RD1 LC1145 RD41 RD27 RD1 LC1146 RD41 RD28 RD1 LC1147 RD41 RD29 RD1 LC1148 RD41 RD30 RD1 LC1149 RD41 RD31 RD1 LC1150 RD41 RD32 RD1 LC1151 RD41 RD33 RD1 LC1152 RD41 RD34 RD1 LC153 RD41 RD42 RD1 LC1154 RD41 RD64 RD1 LC1155 RD41 RD66 RD1 LC1156 RD41 RD68 RD1 LC1157 RD41 RD76 RD1 LC1158 RD64 RD5 RD1 LC1159 RD64 RD6 RD1 LC1160 RD64 RD9 RD1 LC1161 RD64 RD10 RD1 LC1162 RD64 RD12 RD1 LC1163 RD64 RD15 RD1 LC1164 RD64 RD16 RD1 LC1165 RD64 RD17 RD1 LC1166 RD64 RD18 RD1 LC1167 RD64 RD19 RD1 LC1168 RD64 RD20 RD1 LC1169 RD64 RD21 RD1 LC1170 RD64 RD23 RD1 LC1171 RD64 RD24 RD1 LC1172 RD64 RD25 RD1 LC1173 RD64 RD27 RD1 LC1174 RD64 RD28 RD1 LC1175 RD64 RD29 RD1 LC1176 RD64 RD30 RD1 LC1177 RD64 RD31 RD1 LC1178 RD64 RD32 RD1 LC1179 RD64 RD33 RD1 LC1180 RD64 RD34 RD1 LC1181 RD64 RD42 RD1 LC1182 RD64 RD64 RD1 LC1183 RD64 RD66 RD1 LC1184 RD64 RD68 RD1 LC1185 RD64 RD76 RD1 LC1186 RD66 RD5 RD1 LC1187 RD66 RD6 RD1 LC1188 RD66 RD9 RD1 LC1189 RD66 RD10 RD1 LC1190 RD66 RD12 RD1 LC1191 RD66 RD15 RD1 LC1192 RD66 RD16 RD1 LC1193 RD66 RD17 RD1 LC1194 RD66 RD18 RD1 LC1195 RD66 RD19 RD1 LC1196 RD66 RD20 RD1 LC1197 RD66 RD21 RD1 LC1198 RD66 RD23 RD1 LC1199 RD66 RD24 RD1 LC1200 RD66 RD25 RD1 LC1201 RD66 RD27 RD1 LC1202 RD66 RD28 RD1 LC1203 RD66 RD29 RD1 LC1204 RD66 RD30 RD1 LC1205 RD66 RD31 RD1 LC1206 RD66 RD32 RD1 LC1207 RD66 RD33 RD1 LC1208 RD66 RD34 RD1 LC1209 RD66 RD42 RD1 LC1210 RD66 RD68 RD1 LC1211 RD66 RD76 RD1 LC1212 RD68 RD5 RD1 LC1213 RD68 RD6 RD1 LC1214 RD68 RD9 RD1 LC1215 RD68 RD10 RD1 LC1216 RD68 RD12 RD1 LC1217 RD68 RD15 RD1 LC1218 RD68 RD16 RD1 LC1219 RD68 RD17 RD1 LC1220 RD68 RD18 RD1 LC1221 RD68 RD19 RD1 LC1222 RD68 RD20 RD1 LC1223 RD68 RD21 RD1 LC1224 RD68 RD23 RD1 LC1225 RD68 RD24 RD1 LC1226 RD68 RD25 RD1 LC1227 RD68 RD27 RD1 LC1228 RD68 RD28 RD1 LC1229 RD68 RD29 RD1 LC1230 RD68 RD30 RD1 LC1231 RD68 RD31 RD1 LC1232 RD68 RD32 RD1 LC1233 RD68 RD33 RD1 LC1234 RD68 RD34 RD1 LC1235 RD68 RD42 RD1 LC1236 RD68 RD76 RD1 LC1237 RD76 RD5 RD1 LC1238 RD76 RD6 RD1 LC1239 RD76 RD9 RD1 LC1240 RD76 RD10 RD1 LC1241 RD76 RD12 RD1 LC1242 RD76 RD15 RD1 LC1243 RD76 RD16 RD1 LC1244 RD76 RD17 RD1 LC1245 RD76 RD18 RD1 LC1246 RD76 RD19 RD1 LC1247 RD76 RD20 RD1 LC1248 RD76 RD21 RD1 LC1249 RD76 RD23 RD1 LC1250 RD76 RD24 RD1 LC1251 RD76 RD25 RD1 LC1252 RD76 RD27 RD1 LC1253 RD76 RD28 RD1 LC1254 RD76 RD29 RD1 LC1255 RD76 RD30 RD1 LC1256 RD76 RD31 RD1 LC1257 RD76 RD32 RD1 LC1258 RD76 RD33 RD1 LC1259 RD76 RD34 RD1 LC1260 RD76 RD42 RD1
and
wherein RD1 to RD81 has the following structures: - In some embodiments, an organic light emitting device (OLED) is described. The OLED can include an anode; a cathode; and an organic layer, disposed between the anode and the cathode, where the organic layer includes a compound comprising a first ligand LA of Formula IA, Formula IB, or Formula IC, as described herein.
- In some embodiments, a consumer product comprising an OLED as described herein is described.
- In some embodiments, the OLED has one or more characteristics selected from the group consisting of being flexible, being rollable, being foldable, being stretchable, and being curved. In some embodiments, the OLED is transparent or semi-transparent. 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 comprises a RGB pixel arrangement or white plus color filter pixel arrangement. In some embodiments, the OLED is a mobile device, a hand held device, or a wearable device. In some embodiments, the OLED is a display panel having less than 10 inch diagonal or 50 square inch area. In some embodiments, the OLED is a display panel having at least 10 inch diagonal or 50 square inch area. In some embodiments, the OLED is a lighting panel.
- According to another aspect, an emissive region in an OLED (e.g., the organic layer described herein) is disclosed. The emissive region comprises a compound comprising a first ligand LA of Formula IA, Formula IB, or Formula IC, as described herein.
- In some embodiments, the compound can be an emissive dopant. In some embodiments, the compound can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence; see, e.g., U.S. application Ser. No. 15/700,352, which is hereby incorporated by reference in its entirety), triplet-triplet annihilation, or combinations of these processes.
- According to another aspect, a formulation comprising the compound described herein is also disclosed.
- The OLED disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.
- The organic layer can also include a host. In some embodiments, two or more hosts are preferred. In some embodiments, the hosts used maybe a) bipolar, b) electron transporting, c) hole transporting or d) wide band gap materials that play little role in charge transport. In some embodiments, the host can include a metal complex. The host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan. Any substituent in the host can be an unfused substituent independently selected from the group consisting of CnH2n+1, OCnH2n+1, OAr1, N(CnH2n+1)2, N(Ar1)(Ar2), CH═CH—CnH2n+1, C≡C—CnH2n+1, Ar1, Ar1—Ar2, and CnH2n—Ar1, or the host has no substitutions. In the preceding substituents n can range from 1 to 10; and Ar1 and Ar2 can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. The host can be an inorganic compound. For example a Zn containing inorganic material e.g. ZnS.
- The host can be a compound comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene. The host can include a metal complex. The host can be, but is not limited to, a specific compound selected from the group consisting of:
- and combinations thereof.
Additional information on possible hosts is provided below. - In yet another aspect of the present disclosure, a formulation that comprises the novel compound disclosed herein is described. The formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, electron blocking material, hole blocking material, and an electron transport material, disclosed herein.
- Combination with Other Materials
- The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.
- A charge transport layer can be doped with conductivity dopants to substantially alter its density of charge carriers, which will in turn alter its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor may also be achieved. Hole-transporting layer can be doped by p-type conductivity dopants and n-type conductivity dopants are used in the electron-transporting layer.
- Non-limiting examples of the conductivity dopants that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140, US2015060804,
- A hole injecting/transporting material to be used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of the material include, but are not limited to: a phthalocyanine or porphyrin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and silane derivatives; a metal oxide derivative, such as MoOx; a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.
- Examples of aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:
- Each of Ar1 to Ar9 is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the 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, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each Ar may be unsubstituted or may be substituted by a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
- In one aspect, Ar1 to Ar9 is independently selected from the group consisting of:
- wherein k is an integer from 1 to 20; X101 to X108 is C (including CH) or N; Z101 is NAr1, O, or S; Ar1 has the same group defined above.
- Examples of metal complexes used in HIL or HTL include, but are not limited to the following general formula:
- wherein Met is a metal, which can have an atomic weight greater than 40; (Y101-Y102) is a bidentate ligand, Y101 and Y102 are independently selected from C, N, O, P, and S; L101 is an ancillary ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.
- In one aspect, (Y101-Y102) is a 2-phenylpyridine derivative. In another aspect, (Y101-Y102) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc+/Fc couple less than about 0.6 V.
- Non-limiting examples of the HIL and HTL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473, TW201139402, U.S. Ser. No. 06/517,957, US20020158242, US20030162053, US20050123751, US20060182993, US20060240279, US20070145888, US20070181874, US20070278938, US20080014464, US20080091025, US20080106190, US20080124572, US20080145707, US20080220265, US20080233434, US20080303417, US2008107919, US20090115320, US20090167161, US2009066235, US2011007385, US20110163302, US2011240968, US2011278551, US2012205642, US2013241401, US20140117329, US2014183517, U.S. Pat. Nos. 5,061,569, 5,639,914, WO05075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO2013087142, WO2013118812, WO2013120577, WO2013157367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921, WO2014034791, WO2014104514, WO2014157018.
- 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 blocking layer in a device may result in substantially higher efficiencies, and/or longer lifetime, as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an 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 the 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 EBL contains the same molecule or the same functional groups used as one of the hosts described below.
- The light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as 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 complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria is satisfied.
- Examples of metal complexes used as host are preferred to have the following general formula:
- wherein Met is a metal; (Y103-Y104) is a bidentate ligand, Y103 and Y104 are independently selected from C, N, O, P, and S; L101 is an another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.
- In one aspect, the metal complexes are:
- wherein (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.
- In another aspect, Met is selected from Ir and Pt. In a further aspect, (Y103-Y104) is a carbene ligand.
- Examples of other organic compounds used as host are selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the 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, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each option within each group may be unsubstituted or may be substituted by a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
- In one aspect, the host compound contains at least one of the following groups in the molecule:
- wherein R101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. k is an integer from 0 to 20 or 1 to 20. X101 to X108 are independently selected from C (including CH) or N. Z101 and Z102 are independently selected from NR101, O, or S.
- Non-limiting examples of the host materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, U.S. Pat. No. 7,154,114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431, WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472, US20170263869, US20160163995, U.S. Pat. No. 9,466,803,
- One or more additional emitter dopants may be used in conjunction with the compound of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compounds may be used as long as the compounds are typically used as emitter materials. Examples of suitable emitter materials include, but are not limited to, compounds which can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.
- Non-limiting examples of the emitter materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554, EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980, U.S. Ser. No. 06/699,599, U.S. Ser. No. 06/916,554, US20010019782, US20020034656, US20030068526, US20030072964, US20030138657, US20050123788, US20050244673, US2005123791, US2005260449, US20060008670, US20060065890, US20060127696, US20060134459, US20060134462, US20060202194, US20060251923, US20070034863, US20070087321, US20070103060, US20070111026, US20070190359, US20070231600, US2007034863, US2007104979, US2007104980, US2007138437, US2007224450, US2007278936, US20080020237, US20080233410, US20080261076, US20080297033, US200805851, US2008161567, US2008210930, US20090039776, US20090108737, US20090115322, US20090179555, US2009085476, US2009104472, US20100090591, US20100148663, US20100244004, US20100295032, US2010102716, US2010105902, US2010244004, US2010270916, US20110057559, US20110108822, US20110204333, US2011215710, US2011227049, US2011285275, US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US2014103305, U.S. Pat. Nos. 6,303,238, 6,413,656, 6,653,654, 6,670,645, 6,687,266, 6,835,469, 6,921,915, 7,279,704, 7,332,232, 7,378,162, 7,534,505, 7,675,228, 7,728,137, 7,740,957, 7,759,489, 7,951,947, 8,067,099, 8,592,586, 8,871,361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450.
- dHBL:
- 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 blocking layer in a device may result in substantially higher efficiencies and/or longer lifetime as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the HBL material has a lower HOMO (further 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 (further from the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the HBL interface.
- In one aspect, compound used in HBL contains the same molecule or the same functional groups used as host described above.
- In another aspect, compound used in HBL contains at least one of the following groups in the molecule:
- wherein k is an integer from 1 to 20; L101 is an another ligand, k′ is an integer from 1 to 3.
- Electron transport layer (ETL) may include a material capable of transporting electrons. 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 complexes or organic compounds may be used as long as they are typically used to transport electrons.
- In one aspect, compound used in ETL contains at least one of the following groups in the molecule:
- wherein R101 is selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acids, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. Ar1 to Ar3 has the similar definition as Ar's mentioned above. k is an integer from 1 to 20. X101 to X108 is selected from C (including CH) or N.
- In another aspect, the metal complexes used in ETL contains, but not limit to the following general formula:
- wherein (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L101 is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.
- Non-limiting examples of the ETL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose 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, U.S. Pat. Nos. 6,656,612, 8,415,031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535
- In tandem or stacked OLEDs, the CGL plays an essential role in the performance, which is composed of an n-doped layer and a p-doped layer for injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively; then, the bipolar currents reach a steady state gradually. Typical CGL materials include n and p conductivity dopants used in the transport layers.
- In any above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any specifically listed substituent, such as, without limitation, methyl, phenyl, pyridyl, etc. may be undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also may be undeuterated, partially deuterated, and fully deuterated versions thereof.
- Dopant Synthesis
- Compound 10, the ligand used to synthesize Dopant A, was prepared in seven steps according to Scheme I.
- 6-Bromonaphthalen-1-ol (compound 1, 10 g, 44.8 mmol) was dissolved in dry acetone (180 mL) under a room temperature (˜22° C.) atmosphere in a 500 mL, 3-necked round bottomed flask topped with a reflux condenser. Then, potassium carbonate (12.39 g, 90 mmol) and methyl iodide (5.61 ml, 90 mmol) were added and the reaction mixture was stirred at 65° C. for 18 hours. The reaction was cooled to room temperature (˜22° C.), causing a white solid to precipitate from the reaction mixture. The precipitate was then was filtered off and the filtrate was concentrated under vacuum. The reaction mixture was partitioned between EtOAc and brine (200 mL) and the organics were separated and washed with brine (2×50 mL), dried over MgSO4, and the solvents removed to afford an orange oil. Recrystallization from iso-hexane afforded compound 2 of Scheme I as a white solid (8.0 g, 33.7 mmol, 75% yield).
- Potassium carbonate (9.97 g, 72.1 mmol), 6-bromo-1-methoxynaphthalene (5.7 g, 24.04 mmol) and (2-hydroxyphenyl)boronic acid (compound 3, 4.97 g, 36.1 mmol) were dissolved in a 4.5:1 mixture of dioxane:water (300 mL) in a 500 mL three-necked round bottomed flask topped with a reflux condenser. The mixture was sparged with N2 for 15 min, and then tetrakis(triphenylphosphine)palladium(0) (1.389 g, 1.202 mmol) was added, and the mixture was sparged with N2 for additional 5 min. The reaction was stirred for 18 h at 80° C. The reaction mixture was taken to pH 7 using HCl 2N and partitioned between EtOAc and brine. The organics were separated and washed with brine (2×200 mL), dried over MgSO4, and the solvents removed. The crude was purified by flash chromatography using mixtures of iso-hexane/dichloromethane to afford compound 4 of Scheme I as a yellow solid (5.50 g, 21.75 mmol, 90% yield).
- Palladium(II) acetate (0.484 g, 2.157 mmol) and 3-nitropyridine (0.268 g, 2.157 mmol) were placed in a 500 mL high-pressure ACE brand reaction vessel topped with a rubber septum and evacuated/backfilled with N2 three times. Then 2-(5-methoxynaphthalen-2-yl)phenol (5.40 g, 21.57 mmol) dissolved in dry 1,2-dimethoxyethane (150.0 ml) was added under N2 via canula followed by tert-butyl peroxybenzoate (8.14 ml, 43.1 mmol). The ACE reaction vessel was sealed and the reaction mixture stirred at 120° C. for 40 min. The reaction mixture was allowed to cool to room temperature (˜22° C.), then filtered through a plug of Celite*(diatomaceous earth) eluting with dichloromethane. Solvents were removed in vacuo to afford a brown solid. The crude was purified by flash chromatography using mixtures of iso-hexane/acetone to afford compound 5 of Scheme I as a white solid (1.8 g, 7.25 mmol, 33% yield).
- 7-methoxynaphtho[2,3-b]benzofuran (16.0 g, 64.4 mmol) was dissolved in dry dichloromethane (120.0 ml) under N2 in a 250 mL three-necked round bottomed flask fitted with an addition funnel. The mixture was cooled down to −78° C. before tribromoborane (1M in dichloromethane, 97 ml, 97 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature (˜22° C.) and stirred for two hours. The reaction mixture was then poured into water-ice and extracted with dichloromethane (3×100 mL), with 10 mL of acetone to facilitate solubility, dried over MgSO4, and the solvents removed. A red solid was obtained which was further triturated with iso-hexane to afford compound 6 of Scheme I as an off-white solid (14.42 g, 60.9 mmol, 95% yield).
- Naphtho[2,3-b]benzofuran-7-ol (14.4 g, 61.5 mmol) and pyridine (7.46 ml, 92 mmol) were dissolved in dry dichloromethane (300 mL) under N2 in a 3-necked round bottomed flask fitted with an addition funnel. The mixture was cooled down to 0° C. and trifluoromethanesulfonic anhydride (12.46 ml, 73.8 mmol) was added dropwise. The reaction mixture was slowly allowed to warm to room temperature (˜22° C.) and stirred for an additional 16 h. The reaction mixture was partitioned between dichlormethane (100 mL) and saturated aqueous NaHCO3 (200 mL), the organics were then separated, dried over MgSO4 and the solvents removed to afford a brown solid that further triturated with iso-hexane to afford compound 7 of Scheme I as an off-white solid (18.63 g, 50.3 mmol, 82% yield).
- Bis(pinacolato)diboron (15.34 g, 60.4 mmol), naphtho[2,3-b]benzofuran-7-yl trifluoromethanesulfonate (18.44 g, 50.3 mmol), potassium acetate (9.88 g, 101 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)dichloride dichloromethane complex (1.23 g, 1.51 mmol) were dissolved in dry dioxane (200 mL) in a 3-necked round bottomed flask fitted with a reflux condenser. The mixture was sparged with nitrogen for 15 min then the reaction was stirred for 18 h at 100° C. The reaction mixture was partitioned between ethyl acetate (EtOAc) (200 mL) and brine (200 mL), the organics were separated, washed with brine (2×200 mL), dried over MgSO4 and the solvents removed. The crude was purified by flash chromatography using mixtures of iso-hexane/dichloromethane to afford compound 8 of Scheme I as a yellow solid (12.0 g, 34.7 mmol, 68.9%).
- A mixture of 4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-7-yl)-1,3,2-dioxaborolane (2.02 g, 5.9 mmol), 5-methyl-2-chloropyrimidine (compound 9, 0.93 g, 7.2 mmol), 2 M aq. potassium carbonate (6 mL, 12 mmol) and ethanol (30 mL) were sparged with nitrogen for 10 min. Siliacat DPP-Pd silica-based catalyst (0.404 g, 0.12 mmol) was added and the reaction mixture heated at 76° C. for 18 h. The solvent was removed under reduced pressure. The residue was dry-loaded onto silica gel and purified on an Interchim automated system (80 g column) eluting with 0-30% ethyl acetate in heptanes. The product containing fractions were concentrated under reduced pressure and the solid dried in a vacuum oven for 4 hours to afford compound 10 of Scheme I (5-methyl-2-(naphtho[2,3-b]benzofuran-7-yl)-pyrimidine) (1.33 g, 99.3% UPLC purity) as an off-white solid.
- Dopant A was synthesized according to the reaction below.
- A solution of 5-methyl-2-(naphtho[2,3-b]benzofuran-7-yl)pyrimidine (1.48 g, 4.75 mmol, 1.76 equiv) in ethanol (75 mL) was sparged with nitrogen for 10 min. [Ir(2-phenyl-6-methyl-pyridin-2-yl(-1H))2-(MeOH)2](trifluoromethanesulfonate) (2.0 g, 2.7 mmol, 1.0 equiv) was added and the reaction mixture was heated 78° C. for 36 h. The mixture was cooled to room temperature (˜22° C.), filtered, the solids washed with methanol (2×25 mL), and air dried. The crude material was chromatographed on silica gel (135 g) layered with basic alumina (43 g), eluting with 20% hexanes in dichloromethane. Product containing fractions were concentrated under reduced pressure and the solid dried in a vacuum oven for 9 h to afford Dopant A (1.8 g, 82% yield 99.3% HPLC purity) as an orange solid.
- The ligand used to synthesize Dopant B, 5-methyl-2-(naphthalen-1-yl)pyrimnidine, was prepared according to the synthesis scheme below.
- A mixture of naphthalen-1-ylboronic acid (15 g, 96 mmol), 2-chloro-5-methylpyrimidine (9 g. 70 mmol), 2 M aq. potassium carbonate (58 mL, 116 mmol) and ethanol (300 mL) was sparged with nitrogen for 15 min. Siliacat DPP-Pd silica-based catalyst (3.87 g, 1.16 nmol, 0.17 equiv) was added and the reaction mixture heated at 78° C. for 48 h. The reaction mixture was colled to room temperature (˜22° C.) filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with 0-20% ethyl acetate in heptanes to afford 5-methyl-2-(naphthalen-1-yl)pyrimidine (12.65 g, 82% yield 99.8% UPLC purity) as a white solid.
- Dopant B was synthesized according to the equation below.
- A solution of 5-methyl-2-(naphthalen-1-yl)pyrimidine (1.19 g, 5.39 mmol) in ethanol (75 mL) was sparged with nitrogen for 15 minutes, then Ir(2-phenyl-6-methylpyridin-2-yl(-1H))2-(MeOH)2](trifluoromethanesulfonate) (1.0 g, 2.7 mmol) was added and the reaction mixture heated at 78° C. for 30 h. The mixture was cooled to room temperature (˜22° C.), filtered and the solids dissolved in a minimum amount of dichloromethane (traces of insoluble material remained). The crude material was chromatographed on silica gel (100 g) layered with basic alumina (30 g), eluting with 20% hexanes in dichloromethane. Product containing fractions were concentrated under reduced pressure and the solid dried in a vacuum oven for 14 h to afford bis[((2-phenyl-2′-yl)-6-methylpyridin)-1-yl]-((5-methyl-2-(naphthalen-1-yl)-2-′yl)pyrimidin-1-yl) iridium(III) (1.52 g, 75% yield, 99.2% HPLC purity) as an orange solid.
-
- All example devices were fabricated by high vacuum (<10-7 Torr) thermal evaporation. The anode electrode was 1150 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of Liq (8-hydroxyquinoline lithium) followed by 1,000 Å of Al. All devices were encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box (<1 ppm of H2O and O2) immediately after fabrication, and a moisture getter was incorporated inside the package. The organic stack of the device examples consisted of sequentially, from the ITO surface, 100 k of HATCN as the hole injection layer (HIL); 450 Å of HTL-1 as the hole transporting layer (HTL); 400 Å of an emissive layer (EML) comprising Host-1 as a host, SD-1 as a stability dopant (18%), and Dopant A or Dopant B as the emitter (3%); 350 Å of Liq doped with 35% of ETM-1 as the ETL; and 10 Å of Liq as the electron injection layer (EIL). The stability dopant was added to the electron-transporting host to help transport positive charge in the emissive layer.
- Upon fabrication, the electroluminescence (EL) and current density-voltage-luminance (JVL) performance of the devices was measured. The device lifetimes were evaluated at a current density of 80 mA/cm2. The results are summarized in Table I and compare the performance of Dopant A in Example 1 vs. Dopant B in Comparative Example 2. Both dopants afford devices with identical voltages and external quantum efficiencies. However, Dopant A provides narrower line width (full width at half maximum, FWHM) and significantly longer device lifetime than Dopant B. The emission wavelength of Dopant A is also red-shifted versus Dopant B, which is desirable for application of the dopants of the present invention as red emissive materials in OLED devices.
-
TABLE 1 At At 10 mA/cm2 80 mA/ Device λ Vol- cm2 Exam- 1931 CIE max FWHM tage EQE LT95% ple Emitter x y [nm] [au] [au] [au] [au] Inven- Dopant 0.550 0.448 580 0.91 1.00 1.00 1.62 tive A Exam- ple 1 Compar- Dopant 0.518 0.479 567 1.00 1.00 1.00 1.00 ative B Exam- ple 2 au = normalized units - It is 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 deviating from the spirit of the invention. The present invention as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting.
Claims (20)
1. A compound comprising a first ligand LA having the Formula selected from the group consisting of:
wherein ring B and C are each independently a 5-membered or 6-membered aromatic or heteroaromatic ring;
wherein RA, RB, RC, and RD each independently represent mono to the maximum possible number of substituents, or no substituent;
wherein Z1 and Z2 are each independently selected from the group consisting of C and N;
wherein X1, X2, X3, X4, X5, and X6 are each independently selected from the group consisting of C and N;
wherein X1, X2, X3, or X4 is C when it forms a direct bond to Z2;
wherein Y is selected from the group consisting of CRR′, NR′, O, S, SiRR′, and Se;
wherein R, R′, RA, RB, RC, and RD are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two substituents are optionally joined or fused into a ring;
wherein the ligand LA is coordinated to a metal M by the dashed lines to form a 5-membered chelate ring;
wherein M does not form a direct bond to X1 in Formula IB;
wherein M does not form a direct bond to X4 in Formula IC;
wherein the metal M can be coordinated to other ligands; and
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
2. The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Au, and Cu.
3. The compound of claim 1 , wherein M is Ir or Pt.
4. The compound of claim 1 , wherein R, R′, RA, RB, RC, and RD are each independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
5. The compound of claim 1 , wherein Y is O.
6. The compound of claim 1 , wherein X1—X6 are each independently C.
7. The compound of claim 1 , wherein ring C is a fused benzene ring.
8. The compound of claim 1 , wherein ring B is selected from the group consisting of pyridine, pyrimidine, pyrazine, pyridazine, benzene, imidazole, pyrazole, triazole, pyrrole, oxazole, thiazole, and imidazole derived carbene.
9. The compound of claim 1 , wherein the first ligand LA is selected from the group consisting of:
and aza variants thereof; and
wherein Ra is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.
10. The compound of claim 1 , wherein the first ligand LA is selected from the group consisting of LA1 through LA4780, wherein LA1 through LA240 have a structure of Formula II:
wherein LA241 through LA360 have a structure of Formula III:
wherein LA361 through LA456 have a structure of Formula IV,
wherein R2, R4, Y, and X are defined as provided below:
wherein LA457 through LA696 have a structure of Formula V:
wherein LA697 through LA816 have a structure of Formula VI:
wherien LA817 through LA912 have a structure of Formula VII:
wherein R2, R4, and Y are defined as provided below:
wherein LA913 through LA1152 have a structure of Formula VIII:
wherein LA1153 through LA1272 have a structure of Formula IX:
wherein LA1273 through LA1368 have a structure of Formula X:
wherein LA1369 through LA160 have a structure of Formula XI:
wherein LA1609 through LA1728 have a structure of Formula XII:
wherein LA1729 through LA1824 have a structure of Formula XIII:
wherein LA1825 through LA2064 have a structure of Formula XIV:
wherein R1, R5, X, and Y are defined as provided below:
wherein LA2065 through LA2184 have a structure of Formula XV:
wherein LA2185 through LA2280 have a structure of Formula XVI:
wherein LA2281 through LA2520 have a structure of Formula XVII:
wherein LA2521 through LA2640 have a structure of Formula XVIII:
wherein LA641 through LA736 have a structure of Formula XIX:
wherein LA2737 through LA2976 have a structure of Formula XX:
wherein LA2977 through LA3096 have a structure of Formula XXI:
wherein LA3097 through LA3192 have a structure of Formula XXII:
wherein LA3193 through LA3432 have a structure of Formula XXIII:
wherein LA3433 through LA3552 have a structure of Formula XXIV:
wherein LA3553 through LA3648 have a structure of Formula XXV:
wherein LA3649 through LA3888 have a structure of Formula XXVI:
wherein LA3889 through LA4008 have a structure of Formula XXVII:
wherein LA4009 through LA4104 have a structure of Formula XXVII:
wherein LA4105 through LA4344 have a structure of Formula XXIX:
wherein LA4345 through LA4464 have a structure of Formula XXX:
wherein LA4465 through LA4560 have a structure of Formula XXXI:
wherein LA4561 through LA4780 have a structure of Formula XXXII:
wherein RB1 to RB23 have the following structures:
and
wherein RA1 to RA52 have the following structures:
11. The compound of claim 1 , wherein the compound has a formula of M(LA)x(LB)y(LC)z wherein LB and LC are each a bidentate ligand; and wherein x is 1, 2, or 3; y is 0, 1, or 2; z is 0, 1, or 2; and x+y+z is the oxidation state of the metal M.
12. The compound of claim 11 , wherein the compound has a formula selected from the group consisting of Ir(LA)3, Ir(LA)(LB)2, Ir(LA)2(LB), Ir(LA)2(LC), and Ir(LA)(LB)(LC); and wherein LA, LB, and LC are different from each other.
13. The compound of claim 11 , wherein LB and LC are each independently selected from the group consisting of:
wherein each Y1 to Y13 is independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO2, CR1R2, SiR1R2, and GeR1R2;
wherein R1 and R2 are optionally fused or joined to form a ring;
wherein each Ra, Rb, Rc, and Rd may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R1, R2, Ra, Rb, Rc, and Rd are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of Ra, Rb, Rc, and Rd are optionally fused or joined to form a ring or form a multidentate ligand.
14. The compound of claim 12 , wherein the compound is selected from the group consisting of Compound Ax having the formula Ir(LAi)3, Compound By having the formula Ir(LAi)(LBk)2; and Compound Cz having the formula Ir(LAi)2(LCj); wherein x=i, y=468i+k-468, and z=1260i+j-1260; wherein i is an integer from 1 to 4780; wherein k is an integer from 1 to 468; wherein j is an integer from 1 to 1260;
wherein LBk has the following structures:
wherein LC is selected from the group consisting of the following structures:
LC1 through LC1260 are based on a structure of Formula X,
in which R1, R2, and R3 are defined as:
and wherein RD1 to RD81 has the following structures:
15. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound comprising a first ligand LA having the Formula selected from the group consisting of:
wherein ring B and C are each independently a 5-membered or 6-membered aromatic or heteroaromatic ring;
wherein RA, RB, RC, and RD each independently represent mono to the maximum possible number of substituents, or no substituent;
wherein Z1 and Z2 are each independently selected from the group consisting of C and N;
wherein X1, X2, X3, X4, X5, and X6 are each independently selected from the group consisting of C or N;
wherein X1, X2, X3, or X4 is C when it forms a direct bond to Z2;
wherein Y is selected from the group consisting of CRR′, NR′, O, S, SiRR′, and Se;
wherein R, R′, RA, RB, RC, and RD are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two substituents are optionally joined or fused into a ring;
wherein the ligand LA is coordinated to a metal M by the dashed lines to form a 5-membered chelate ring;
wherein M does not form a direct bond to X1 in Formula IB;
wherein M does not form a direct bond to X4 in Formula IC;
wherein the metal M can be coordinated to other ligands; and
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
16. The OLED of claim 15 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
17. The OLED of claim 15 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of a metal complex, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
19. A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound comprising a first ligand LA having the Formula selected from the group consisting of:
wherein ring B and C are each independently a 5-membered or 6-membered aromatic or heteroaromatic ring;
wherein RA, RB, RC, and RD each independently represent mono to the maximum possible number of substituents, or no substituent;
wherein Z1 and Z2 are each independently selected from the group consisting of C and N;
wherein X1, X2, X3, X4, X5, and X6 are each independently selected from the group consisting of C or N;
wherein X1, X2, X3, or X4 is C when it forms a direct bond to Z2;
wherein Y is selected from the group consisting of CRR′, NR′, O, S, SiRR′, and Se;
wherein R, R′, RA, RB, RC, and RD are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any two substituents are optionally joined or fused into a ring;
wherein the ligand LA is coordinated to a metal M by the dashed lines to form a 5-membered chelate ring;
wherein M does not form a direct bond to X1 in Formula IB;
wherein M does not form a direct bond to X4 in Formula IC;
wherein the metal M can be coordinated to other ligands;
wherein the ligand LA is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand; and
wherein the consumer product is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, or a sign.
20. A formulation comprising the compound of claim 1 .
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2018
- 2018-08-27 US US16/113,587 patent/US11778897B2/en active Active
- 2018-09-20 KR KR1020180112961A patent/KR102557601B1/en active IP Right Grant
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