CN115260201A - Iridium complex based on nitrogen heterocyclic aromatic ring modified indolo [3,2,1-jk ] carbazole main ligand and application thereof - Google Patents
Iridium complex based on nitrogen heterocyclic aromatic ring modified indolo [3,2,1-jk ] carbazole main ligand and application thereof Download PDFInfo
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- CN115260201A CN115260201A CN202210822420.2A CN202210822420A CN115260201A CN 115260201 A CN115260201 A CN 115260201A CN 202210822420 A CN202210822420 A CN 202210822420A CN 115260201 A CN115260201 A CN 115260201A
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- China
- Prior art keywords
- derivative
- carbazole
- iridium complex
- indolo
- irn
- Prior art date
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- Pending
Links
- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 37
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 239000003446 ligand Substances 0.000 title claims abstract description 18
- SZLNOBJKCVERBJ-UHFFFAOYSA-N 1-azapentacyclo[10.6.1.02,7.08,19.013,18]nonadeca-2,4,6,8(19),9,11,13,15,17-nonaene Chemical class C12=CC=CC=C2N2C3=CC=CC=C3C3=CC=CC1=C32 SZLNOBJKCVERBJ-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 12
- 239000000463 material Substances 0.000 claims abstract description 32
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims abstract description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- -1 triphenylsilyl groups Chemical group 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- VGNCCWXNNWGQQA-UHFFFAOYSA-N 2-(triazol-2-yl)pyridine Chemical compound N1=CC=NN1C1=CC=CC=N1 VGNCCWXNNWGQQA-UHFFFAOYSA-N 0.000 claims description 2
- HUVURCFUCALLDM-UHFFFAOYSA-N OP(O)=O.C1=CC=NC=C1 Chemical compound OP(O)=O.C1=CC=NC=C1 HUVURCFUCALLDM-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 229940081066 picolinic acid Drugs 0.000 claims description 2
- MBVGZSSYNIBAKI-UHFFFAOYSA-N pyridine-2-carbothioic s-acid Chemical compound OC(=S)C1=CC=CC=N1 MBVGZSSYNIBAKI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 4
- 238000005286 illumination Methods 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract description 3
- 230000005281 excited state Effects 0.000 abstract description 2
- 238000005424 photoluminescence Methods 0.000 abstract description 2
- 238000006862 quantum yield reaction Methods 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 238000009825 accumulation Methods 0.000 abstract 1
- 230000007704 transition Effects 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 144
- 238000005160 1H NMR spectroscopy Methods 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002503 iridium Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- UFWDOFZYKRDHPB-UHFFFAOYSA-N 9-[3-[6-(3-carbazol-9-ylphenyl)pyridin-2-yl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(N=2)C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 UFWDOFZYKRDHPB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- 229910006400 μ-Cl Inorganic materials 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical class FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
- QLRKALMVPCQTMU-UHFFFAOYSA-N 2-bromo-1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C(Br)=C1 QLRKALMVPCQTMU-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- HNACKJNPFWWEKI-UHFFFAOYSA-N 3,6-dimethyl-9h-carbazole Chemical compound C1=C(C)C=C2C3=CC(C)=CC=C3NC2=C1 HNACKJNPFWWEKI-UHFFFAOYSA-N 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The invention belongs to the technical field of electroluminescent materials, and relates to a nitrogen-mixed aromatic ring derivative introduced to the 9 th position of indolo [3,2,1-jk ] carbazole and a novel iridium complex using the nitrogen-mixed aromatic ring derivative as a main ligand. According to the invention, the 9 th site of indolo [3,2,1-jk ] carbazole and derivatives thereof is introduced into aza aryl groups such as pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, isoquinolyl or quinazolinyl and the like to obtain a main ligand structure, so that the rigidity of the ligand and the complex is increased, the luminescent color and efficiency of the complex are regulated and controlled, the steric hindrance is realized, the molecular accumulation is reduced, and the non-radiative transition process of the molecule is inhibited. The iridium complex of the invention has high photoluminescence quantum yield and short excited state life, and has the characteristic of narrow-band emission. The device prepared by the iridium complex has excellent performance, high external quantum efficiency and low efficiency roll-off characteristics, and has potential application value in the fields of OLED display and illumination.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent devices (OLED), in particular to an iridium complex of an indolo [3,2,1-jk ] carbazole derivative with a nitrogen-heteroaromatic ring modified main ligand and application of the iridium complex as a phosphorescent material in an OLED device.
Background
The electro-optic conversion technology of the OLED has wide application in the fields of panel display and illumination, and the luminescent material is the core part of the OLED, especially the phosphorescent metal complex, wherein the trivalent iridium complex has the advantages of easy modification of chemical structure, flexible control of photophysical properties, high luminous efficiency, short excitation life, good device performance and the like. It is noteworthy that heteroligand-based iridium complexes are the most studied ones, since the color and properties of iridium complexes can be tuned by a combination of various cyclometallated primary and secondary ligands. However, in order to satisfy high-quality display applications, a light-emitting material having good color purity and narrow-band emission characteristics is highly desirable to contribute to the improvement of device performance.
Carbazolyl is a good chromophore with high hole transmission capacity and triplet state energy, and its derivative has been widely used in hole transmission material, main body material and luminescent material. The carbazole compound has a plurality of active reaction sites, and is easy to modify by combining with a functional unit to form an organic ligand of a luminescent material and a phosphorescent complex. In addition, the electron-donating ability of different positions on the carbazole unit can affect the energy level of the luminescent material, so that the functionalization of different substituted positions can effectively adjust the luminescent color and the luminescent efficiency of the complex. Among them, the iridium complex ligand containing indole [3,2,1-jk ] carbazole unit has high hole transport capability, narrow light-emitting band and good device performance, and has attracted much attention in recent years.
Disclosure of Invention
Aiming at the defects of the prior art, the invention designs a class of aza-aromatic ring main ligand derivatives and iridium complexes introduced into the 9-position of indole [3,2,1-jk ] carbazole, and applies the materials to OLED devices, thereby providing a novel high-efficiency narrow-band luminescent material.
The specific technical scheme of the invention is as follows:
an azaaromatic ring modified indolo [3,2,1-jk ] carbazole having the structure:
r1 represents a substituted or unsubstituted aromatic heterocyclic group, preferably a pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, isoquinolyl or quinazolinyl group substituted at any position by one or more of H, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, C1-C10 alkylsilyl, a silyl substituted by 1 to 3 phenyl groups, more preferably one or more substituted by H, methyl, methoxy, trifluoromethyl, trimethylsilyl, triphenylsilyl
R2 and R3 are the same or different and are independently selected from C1-C10 alkyl, preferably C1-C6 alkyl, more preferably methyl, ethyl, propyl, isopropyl, tert-butyl, isobutyl or isoamyl;
x represents C or N.
The invention also aims to provide an iridium complex, wherein the indole [3,2,1-jk ] carbazole modified by the nitrogen heterocyclic aromatic ring is used as a main ligand, and picolinic acid or a derivative thereof, pyridine phosphonic acid or a derivative thereof, tetraphenyl phosphonimide or a derivative thereof, thiotetraphenyl phosphonimide or a derivative thereof, thiopicolinic acid or a derivative thereof, amidine derivatives, 2- (5-phenyl-1, 3, 4-oxadiazole-2-) phenol or a derivative thereof, 2-phenylpyridine or a derivative thereof, 2- (2-pyridyl) -triazole or a derivative thereof, 8- (2-pyridyl) benzofuran [2,3-b ] pyridine or a derivative thereof and the like are used as auxiliary ligands.
In a specific embodiment of the present invention, the iridium complex has the following structural formula:
r1 represents a substituted or unsubstituted aromatic heterocyclic group, preferably a pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, isoquinolinyl or quinazolinyl group substituted at any position by one or more of H, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, C1-C10 alkylsilyl, silyl substituted by 1 to 3 phenyl groups, more preferably one or more substituted by H, methyl, methoxy, trifluoromethyl, trimethylsilyl, triphenylsilyl
R2-R5 are the same or different and are independently selected from C1-C10 alkyl, preferably C1-C6 alkyl, more preferably methyl, ethyl, propyl, isopropyl, tert-butyl, isobutyl or isoamyl;
x represents C or N.
Preferably, the iridium complex is selected from the following structures:
the indole [3,2,1-jk ] carbazole modified by the nitrogen-heterocyclic aromatic ring can be obtained by reacting a 2-bromo-1-fluoro-benzene derivative with a carbazole/carboline derivative to obtain an o-bromobenzene-substituted carbazole/carboline derivative, then carrying out a ring-closing reaction on bromobenzene and carbazole/carboline to obtain an indole [3,2,1-jk ] carbazole/carboline precursor, and further carrying out bromination on the 9 th position and carrying out a coupling reaction with boric acid of the nitrogen-heterocyclic aromatic ring.
The iridium complexes of the invention may be prepared by conventional methods, for example by reacting a primary ligand with IrCl3Refluxing in a mixed solution of ethoxyethanol and water for 2 hours according to the proportion of 2; then refluxing the iridium chlorine-bridge complex and the beta-diketone auxiliary ligand with a corresponding structure in ethoxyethanol for 2 hours to obtain a crude product of the iridium complex, performing column chromatography to obtain a pure product, and further performing sublimation purification under a vacuum condition to obtain the luminescent material meeting the requirements of preparing the OLED device.
The invention also aims to provide the nitrogen heteroaromatic ring modified indolo [3,2,1-jk ] carbazole or the iridium complex as a phosphorescent material for preparing an organic electroluminescent device.
The iridium complex can be used for preparing OLED devices, for example, organic electroluminescent devices comprise a substrate, an anode, a hole injection material, a hole transport layer, an organic light-emitting layer, an electron transport layer, an electron injection material and a cathode. The substrate is glass, the anode is Indium Tin Oxide (ITO), the hole injection layer is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN), the hole layer is 4,4' -cyclohexyl di [ N, N-di (4-methylphenyl) aniline (TAPC), the electron transport layer is 1,3, 5-tri [ (3-pyridyl) -3-phenyl ] benzene (TmPyPb), the electron injection material is LiF, and the cathode is metal Al; the organic light-emitting layer comprises a host material and a light-emitting material, wherein the host material is 2, 6-bis ((9H-carbazole-9-yl) -3, 1-phenylene) pyridine (2, 6 DCzPPy), and the light-emitting material is the iridium complex.
The invention has the beneficial effects that: the indole [3,2,1-jk ] carbazole 9-position introduced nitrogen heteroaromatic ring derivative provided by the invention has the effects of regulating and controlling the luminescent color, efficiency and electron transmission performance of the material on an iridium complex, increasing the stability of the material, improving the efficiency of a device and reducing the efficiency roll-off. The iridium complex has the characteristics of high photoluminescence quantum yield, short excited state life and narrow band emission. The device prepared by the iridium complex has excellent performance, has the characteristics of low starting voltage, high external quantum efficiency, low efficiency roll-off and narrow-band emission, and has potential application value in the field of OLED illumination and display.
Drawings
FIG. 1 shows the absorption and emission spectra of an iridium complex Ir01 according to the invention.
FIG. 2 shows the luminance vs. voltage (a) and the external quantum efficiency vs. luminance curve (b) of an OLED of iridium complex Ir01 according to the invention.
Fig. 3 is an absorption and emission spectrum of the iridium complex Ir57 of the present invention.
Fig. 4 is an OLED luminance-voltage (a) and external quantum efficiency-luminance curve (b) of the iridium complex Ir57 of the present invention.
Detailed Description
The terms used in the present invention have meanings generally understood by those of ordinary skill in the art unless otherwise specified.
The present invention is described in further detail below with reference to specific examples and with reference to the data. It will be understood that this example is intended to illustrate the invention and not to limit the scope of the invention in any way.
In the following examples, various procedures and methods not described in detail are conventional methods well known in the art.
Example 1 preparation of an Iridium Complex according to the present invention
Synthetic routes to ligands and iridium complexes. (1):tBuONa,DMF,130℃,(2):Pd(OAc)2,Cs2CO3,(tBu)3P,TEBAC, DMAc,140℃,(3):Br2,HOAc,75℃,(4):n-BuLi,B(OMe)3,THF,-78℃；HCl,H2O,rt,(5):Pd(dppf)2Cl2, Cs2CO3,1,4-dioxane&water,100℃,(6):IrCl3,1,4-dioxane&water,100℃,(7)Na-acac,2-ethoxyethanol, 110℃。
preparation of compound 1 in the above route: 2-bromo-1-fluoro-4-methylbenzene (2.43g, 12.89mmol), 3, 6-dimethyl-9H-carbazole (2.10g, 10.74mmol), sodium tert-butoxide (1.80g, 16.11mmol) and 20mL of DMF were weighed separately in a 50mL three-necked flask, evacuated with nitrogen and stirred at 130 ℃ overnight. When the reaction was completed, the reaction was cooled to room temperature, dichloromethane was added, DMF was removed by washing with saturated brine several times, and the solution was rotary evaporated under reduced pressure to obtain a solid, which was further purified by silica gel column chromatography (petroleum ether/dichloromethane =20/1 as eluent) to obtain 2.50g of 1 as a white solid with a yield of 70%.
Preparation of compound 2 in the above route: compound 1 (6.69 mmol), DME (6.69 mmol), cs under nitrogen2CO3(13.38mmol)、Pd(OAc)2(0.80mmol)、P(tBu)3The mixed solution (1.60 mmol) and benzyltributylammonium chloride (6.69 mmol) was refluxed at 140 ℃ for 5 hours. After cooling to room temperature, dichloromethane was added, followed by multiple washes with saturated brine to remove DME, and the solution was rotary evaporated under reduced pressure to give a solid which was further purified by silica gel column chromatography (petroleum ether as eluent) to give 2.01g of white solid 2 in 75% yield.
Preparation of compound 3 in the above route: product 2 (5.44 mmol) was dissolved in acetic acid and heated to 75 ℃ and Br dissolved in acetic acid2(4.90 mmol) was added dropwise to the solution. After the dropwise addition, the solution was stirred at 75 ℃ for 1 hour and then cooled to room temperature. DCM was added to the solution, water and saturated NaHCO3The solution was washed several times to remove acetic acid. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using pure PE as an eluent to obtain a crude product. The crude product was used in the subsequent reaction without further purification.
Preparation of compound 4 in the above route: n-BuLi (3.80mL, 9.50mmol) was added dropwise to a solution of product 3 (7.84 mmol) in anhydrous THF (50 mL) at-78 deg.C to give a light yellow solution. After stirring for 1 hour, trimethyl borate (11.8 mmol) was added to the solution. The resulting solution was stirred at-78 ℃ for 40 minutes and allowed to warm to room temperature with stirring overnight. Then 60mL of water were added to the solution and the pH was adjusted to 7 using dilute hydrochloric acid. The organic layer was extracted with ether and concentrated under reduced pressure to give a white solid for subsequent reaction without further purification.
Preparation of ligand L1 in the above route: mixing Pd (dppf)2Cl2(0.24mmol)、Cs2CO3(7.29 mmol), product 4 (4.86 mmol) and 2-bromopyridine (7.29 mmol) were added to a three-necked flask under a nitrogen atmosphere. A mixed solvent of 1, 4-dioxane and water was added thereto, and stirred at 100 ℃ overnight. After cooling, extract with EA and water and concentrate the organic layer. The residue was purified by silica gel column chromatography (eluent PE/DCM =2/1,v/v) to give 0.43g of white solid L1 in 22% yield.
Preparation of the chloro-bridged complexes of Iridium in the above route [ Ir (L)2(μ-Cl)]2: irCl is reacted with3(1 mmol) and L1 (2.2 mmol) are added into a reaction bottle, and a mixed solution of ethylene glycol diethyl ether/water (20 mL/5 mL) is added under the condition of introducing nitrogen. Refluxing is carried out for 2 hours at 130 ℃, after the reaction is finished, the temperature is reduced to room temperature, and the chlorine bridge is obtained by filtration with the yield of 85 percent.
Preparation of iridium complex Ir01 in the above route: mixing the above iridium chloro-bridged complex [ Ir (L)2(μ-Cl)]2(0.25 mmol) and the sodium salt of the ancillary ligand acetylacetone (Na-acac) (0.60 mmol) were dissolved in ethylene glycol ethyl ether (15 mL) and stirred under a nitrogen atmosphere at 110 ℃ for 6h. After cooling, the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (PE/DCM =8/1,v/v) to obtain Ir01 as a solid.
Ir01：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 2H), 8.00-8.16 (m, 4H), 7.55-7.86 (m, 4H), 7.33-7.53 (m, 4H), 6.90-7.00 (m, 2H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.05-2.03 (m, 6H), MS (ESI): calculated value C57H46IrN4O2[M]1011.33, the experimental value is 1011.24.
Other complexes Ir02-Ir72 was synthesized in the same manner.
Ir02：1H NMR(400MHz,CDCl3) δ 8.56-8.66 (m, 2H), 7.45-7.56 (m, 4H), 7.35-7.43 (m, 2H), 7.28-7.35 (m, 6H), 6.88-7.05 (m, 6H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.04-1.26 (m, 18H), MS (ESI): calculated value C63H58IrN4O2[M]1095.42, test value 1095.29.
Ir03：1H NMR(400MHz,CDCl3) δ 8.49-8.62 (m, 2H), 7.56-7.83 (m, 4H), 7.45-7.53 (m, 4H), 7.31-7.53 (m, 4H), 6.96-7.18 (m, 6H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.68-1.75 (m, 3H), 1.32-1.39 (m, 36H), 1.24-1.31 (m, 3H), MS (ESI): calculated value C69H70IrN4O2[M]1179.51 and 1079.48.
Ir04：1H NMR(400MHz,CDCl3) δ 8.52-8.61 (m, 2H), 7.54-7.66 (m, 6H), 7.30-7.52 (m, 6H), 6.90-7.15 (m, 6H), 5.71 (s, 1H), 2.31-2.43 (m, 6H), 1.29-1.36 (m, 36H), 1.05-1.30 (m, 18H), MS (ESI): calculated value C75H82IrN4O2[M]1263.61, and 1263.58.
Ir05：1H NMR(400MHz,CDCl3)δ8.46-8.66(m,2H),7.50-7.66(m,2H) 7.25-7.46 (m, 8H), 6.93-7.13 (m, 2H), 6.70-6.89 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.15-1.93 (m, 6H), MS (ESI): calculated value C59H44F6IrN4O2[M]1147.30, experimental value 1147.27.
Ir06：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 2H), 7.50-7.66 (m, 2H), 7.28-7.43 (m, 8H), 6.80-7.23 (m, 6H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 0.96-1.35 (m, 18H), MS (ESI): calculated value C65H56F6IrN4O2[M]1231.37, experimental value 1231.35.
Ir07：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 2H), 7.50-7.66 (m, 6H), 7.28-7.43 (m, 4H), 6.90-7.23 (m, 6H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C71H68F6IrN4O2[M]1315.49, and the experimental value is 1315.46.
Ir08：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 2H), 7.50-7.66 (m, 6H), 7.28-7.43 (m, 4H), 6.90-7.23 (m, 6H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.52 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C77H80F6IrN4O2[M]1399.58 and 1399.56.
Ir09：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 2H), 7.55-7.86 (m, 2H), 7.35-7.43 (m, 6H), 7.20-7.33 (m, 4H), 6.80-6.96 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.15-1.93 (m, 6H), -0.05-0.52 (m, 18H), MS (ESI): calculated value C63H62IrN4O2Si2[M]1155.40 and 1155.39.
Ir10：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 2H), 7.55-7.86 (m, 2H), 7.20-7.43 (m, 10H), 6.80-6.96 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 0.96-1.35 (m, 18H) -0.05-0.52 (m, 18H), MS (ESI): calculated value C69H74IrN4O2Si2[M]1239.50, experimental value 1239.49.
Ir11：1H NMR(400MHz,CDCl3)δ8.46-8.66(m,2H),7.55-7.86(m,6H),7.20-7.43(m,6H), 6.90-7.16 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H) -0.05-0.52 (m, 18H), MS (ESI): calculated value C75H86IrN4O2Si2[M]1323.59, and 1323.58.
Ir12：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 2H), 7.55-7.86 (m, 6H), 7.20-7.43 (m, 6H), 6.90-7.16 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.52 (m, 36H), 1.05-1.28 (m, 18H), -0.05-0.52 (m, 18H), MS (ESI): calculated value C81H98IrN4O2Si2[M]1407.69, experimental value 1407.68.
Ir13：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.68-7.79 (m, 2H), 7.43-7.62 (m, 6H), 7.30-7.41 (m, 2H), 6.82-7.16 (m, 6H), 5.75 (s, 1H), 2.31-2.53 (m, 12H), 1.55-2.03 (m, 6H), MS (ESI): calculated value C53H40IrN6O2[M]985.28 and the experimental value is 985.26.
Ir14：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.68-7.79 (m, 2H), 7.43-7.62 (m, 6H), 7.30-7.41 (m, 4H), 6.82-7.16 (m, 6H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 0.96-1.35 (m, 18H) MS (ESI): calculated value C59H52IrN6O2[M]1069.38 and 1069.34, the experimental value.
Ir15：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.43-7.76 (m, 10H), 6.90-7.20 (m, 6H), 5.75 (s, 1H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C65H64IrN6O2[M]1153.47 and 1153.44.
Ir16：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.43-7.76 (m, 10H), 6.90-7.20 (m, 6H), 5.75 (s, 1H), 1.31-1.52 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C71H76IrN6O2[M]1237.57, experimental value 1237.54.
Ir17：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.55-7.76 (m, 2H), 7.32-7.52 (m, 6H), 6.80-7.13 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 3H), MS (ESI): calculated value C57H42F6IrN6O2[M]1149.29, and the experimental value is 1149.24.
Ir18：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.55-7.76 (m, 2H), 7.32-7.52 (m, 6H), 6.80-7.13 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.02-1.29 (m, 18H), MS (ESI): calculated value C63H54F6IrN6O2[M]1233.38, experimental value 1233.34.
Ir19：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.55-7.76 (m, 4H), 7.38-7.52 (m, 4H), 6.90-7.13 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C69H66F6IrN6O2[M]1317.48, and the experimental value is 1317.44.
Ir20：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.55-7.76 (m, 4H), 7.38-7.52 (m, 4H), 6.90-7.13 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.52 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C75H78F6IrN6O2[M]1401.57 and 1401.53 as experimental value.
Ir21：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.55-7.86 (m, 4H), 7.05-7.43 (m, 6H), 6.80-7.00 (m, 2H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 3H), -0.05-0.52 (m, 18H), MS (ESI): calculated value C61H60IrN6O2Si2[M]1157.39 and the experimental value is 1157.34.
Ir22：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.55-7.86 (m, 4H), 7.05-7.43 (m, 6H), 6.80-7.00 (m, 2H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.02-1.29 (m, 18H), -0.05-0.52 (m, 18H), MS (ESI): calculated value C67H72IrN6O2Si2[M]1241.49, experimental value 1241.44.
Ir23：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.55-7.86 (m, 6H), 7.05-7.43 (m, 6H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), -0.05-0.52 (m, 18H), MS (ESI): calculated value C73H84IrN6O2Si2[M]1235.58, experimental value 1235.54.
Ir24：1H NMR(400MHz,CDCl3) δ 8.46-8.66 (m, 4H), 7.55-7.86 (m, 6H), 7.05-7.43 (m, 6H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.52 (m, 36H), 1.05-1.28 (m, 18H), -0.05-0.52 (m, 18H), MS (ESI): calculated value C79H96IrN6O2Si2[M]1409.68 and 1409.64 as an experimental value.
Ir25：1H NMR(400MHz,CDCl3) δ 8.66-8.82 (m, 2H), 8.40-8.56 (m, 2H), 7.18-7.39 (m, 8H), 6.80-7.08 (m, 6H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.15-1.93 (m, 6H), MS (ESI): calculated value C55H44IrN6O2[M]1013.32, and 1013.34.
Ir26：1H NMR(400MHz,CDCl3) δ 8.66-8.82 (m, 2H), 8.40-8.56 (m, 2H), 7.18-7.39 (m, 8H), 6.80-7.08 (m, 6H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 0.96-1.35 (m, 18H), MS (ESI): calculated value C61H56IrN6O2[M]1097.41, experimental value 1097.44.
Ir27：1H NMR(400MHz,CDCl3) δ 8.66-8.82 (m, 2H), 8.40-8.56 (m, 2H), 7.55-7.68 (m, 4H), 7.28-7.43 (m, 4H), 6.90-7.18 (m, 6H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C67H68IrN6O2[M]1181.50, experimental value 1181.52.
Ir28：1H NMR(400MHz,CDCl3) δ 8.66-8.82 (m, 2H), 8.40-8.56 (m, 2H), 7.55-7.68 (m, 4H), 7.28-7.43 (m, 4H), 6.90-7.18 (m, 6H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C73H80IrN6O2[M]1265.60, test value 1265.62.
Ir29：1H NMR(400MHz,CDCl3) δ 8.73-8.86 (m, 2H), 8.40-8.66 (m, 4H), 7.55-7.79 (m, 2H), 7.20-7.42 (m, 4H), 6.86-7.00 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 3H), MS (ESI): calculated value C53H42IrN8O2[M]1015.31 as the experimental value, 1015.34.
Ir30：1H NMR(400MHz,CDCl3) δ 8.73-8.86 (m, 2H), 8.40-8.66 (m, 4H), 7.55-7.79 (m, 2H), 7.20-7.42 (m, 4H), 6.86-7.00 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.04-1.49 (m, 18H), MS (ESI): calculated value C59H54IrN8O2[M]1099.40, and 1099.42.
Ir31：1H NMR(400MHz,CDCl3) δ 8.73-8.86 (m, 2H), 8.40-8.66 (m, 4H), 7.55-7.79 (m, 4H), 6.90-7.32 (m, 6H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C65H66IrN8O2[M]1183.49, and 1183.46.
Ir32：1H NMR(400MHz,CDCl3) δ 8.73-8.86 (m, 2H), 8.40-8.66 (m, 4H), 7.55-7.79 (m, 4H), 6.90-7.32 (m, 6H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C71H78IrN8O2[M]1267.59, and 1267.56.
Ir33：1H NMR(400MHz,CDCl3) δ 8.54-8.73 (m, 6H), 7.08-7.46 (m, 8H), 6.80-7.00 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.15-1.93 (m, 6H), MS (ESI): calculated value C55H44IrN6O2[M]1013.32, and 1013.34 experimental value.
Ir34：1H NMR(400MHz,CDCl3) δ 8.54-8.73 (m, 6H), 7.08-7.46 (m, 8H), 6.80-7.00 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 0.96-1.35 (m, 18H) MS (ESI): calculated value C61H56IrN6O2[M]1097.41, and the experimental value is 1097.45.
Ir35：1H NMR(400MHz,CDCl3) δ 8.54-8.73 (m, 6H), 7.55-7.76 (m, 4H), 7.08-7.35 (m, 8H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C67H68IrN6O2[M]1185.50, and the experimental value is 1185.52.
Ir36：1H NMR(400MHz,CDCl3)δ8.54-8.73(m,6H),7.55-7.76(m,4H),7.08-7.35(m,8H), 5.75(s,1H),2.33-2.53(m,6H),1.31-1.43(m,36H),1.05-1.28(m,18H) MS (ESI): calculated value C73H80IrN6O2[M]1265.60, test value 1265.64.
Ir37：1H NMR(400MHz,CDCl3) δ 8.46-8.76 (m, 8H), 7.51-7.86 (m, 2H), 7.03-7.43 (m, 4H), 6.80-7.00 (m, 2H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 3H), MS (ESI): calculated value C53H42IrN8O2[M]1015.31 as shown in the specification, and the experimental value is 1015.33.
Ir38：1H NMR(400MHz,CDCl3) δ 8.46-8.76 (m, 8H), 7.51-7.86 (m, 2H), 7.03-7.43 (m, 4H), 6.80-7.00 (m, 2H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.28-1.49 (m, 18H), MS (ESI): calculated value C59H54IrN8O2[M]1099.40, and 1099.42.
Ir39：1H NMR(400MHz,CDCl3) δ 8.46-8.76 (m, 8H), 7.51-7.86 (m, 4H), 7.03-7.43 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C65H66IrN8O2[M]1183.49, experimental value 1183.43.
Ir40：1H NMR(400MHz,CDCl3) δ 8.46-8.76 (m, 8H), 7.51-7.86 (m, 4H), 7.03-7.43 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C71H78IrN8O2[M]1267.59 and 1267.54.
Ir41：1H NMR(400MHz,CDCl3) δ 9.13-9.34 (m, 2H), 8.46-8.66 (m, 2H), 7.45-7.66 (m, 2H), 7.19-7.38 (m, 8H), 6.90-7.00 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.15-1.93 (m, 6H), MS (ESI): calculated value C55H44IrN6O2[M]1013.31, and 1013.32 as experimental value.
Ir42：1H NMR(400MHz,CDCl3) δ 9.13-9.34 (m, 2H), 8.46-8.66 (m, 2H), 7.45-7.66 (m, 2H), 7.19-7.38 (m, 8H), 6.90-7.00 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 0.96-1.35 (m, 18H) MS (ESI): calculated value C61H56IrN6O2[M]1097.41, experimental value 1097.39.
Ir43：1H NMR(400MHz,CDCl3) δ 9.13-9.34 (m, 2H), 8.46-8.66 (m, 2H), 7.45-7.76 (m, 6H), 7.09-7.38 (m, 8H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C67H68IrN6O2[M]1181.50, and 1181.48.
Ir44：1H NMR(400MHz,CDCl3) δ 9.13-9.34 (m, 2H), 8.46-8.66 (m, 2H), 7.45-7.76 (m, 6H), 7.09-7.38 (m, 8H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C73H80IrN6O2[M]1265.60 and 1265.59.
Ir45：1H NMR(400MHz,CDCl3) δ 9.13-9.34 (m, 2H), 8.46-8.66 (m, 4H), 7.45-7.76 (m, 4H), 7.13-7.38 (m, 4H), 6.54-6.93 (m, 2H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 3H), MS (ESI): calculated value C53H42IrN8O2[M]1015.31 and the experimental value is 1015.26.
Ir46：1H NMR(400MHz,CDCl3) δ 9.13-9.34 (m, 2H), 8.46-8.66 (m, 4H), 7.45-7.76 (m, 4H), 7.13-7.38 (m, 4H), 6.54-6.93 (m, 2H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.28-1.49 (m, 18H), MS (ESI): calculated value C59H54IrN8O2[M]1099.40, experimental value 1099.36.
Ir47：1H NMR(400MHz,CDCl3) δ 9.13-9.34 (m, 2H), 8.46-8.66 (m, 4H), 7.45-7.76 (m, 6H), 7.03-7.38 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C65H66IrN8O2[M]1183.49, and 1183.47 as an experimental value.
Ir48：1H NMR(400MHz,CDCl3) δ 9.13-9.34 (m, 2H), 8.46-8.66 (m, 4H), 7.45-7.76 (m, 6H), 7.03-7.38 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C71H78IrN8O2[M]1267.59 and 1267.56.
Ir49：1H NMR(400MHz,CDCl3)δ8.76-8.96(m,2H),7.65-7.86(m,2H),7.13-7.43(m,10H) 6.54-6.93 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.15-1.93 (m, 6H), MS (ESI): calculated value C55H44IrN6O2[M]1013.31, and 1013.29 as experimental value.
Ir50：1H NMR(400MHz,CDCl3) δ 8.76-8.96 (m, 2H), 7.65-7.86 (m, 2H), 7.13-7.43 (m, 10H), 6.54-6.93 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 0.96-1.35 (m, 18H) MS (ESI): calculated value C61H56IrN6O2[M]1097.40, test value 1097.38.
Ir51：1H NMR(400MHz,CDCl3) δ 8.76-8.96 (m, 2H), 7.55-7.86 (m, 6H), 7.03-7.43 (m, 10H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C67H68IrN6O2[M]1181.50, experimental value 1181.45.
Ir52：1H NMR(400MHz,CDCl3) δ 8.76-8.96 (m, 2H), 7.55-7.86 (m, 6H), 7.03-7.43 (m, 10H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C73H80IrN6O2[M]1265.60 and 1265.59.
Ir53：1H NMR(400MHz,CDCl3) δ 8.56-8.94 (m, 4H), 7.58-7.82 (m, 4H), 7.03-7.39 (m, 6H), 6.54-6.93 (m, 2H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 3H) MS (ESI): calculated value C53H42IrN8O2[M]1015.31, experimental value 1015.30.
Ir54：1H NMR(400MHz,CDCl3) δ 8.56-8.94 (m, 4H), 7.58-7.82 (m, 4H), 7.03-7.39 (m, 6H), 6.54-6.93 (m, 2H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.28-1.49 (m, 18H), MS (ESI): calculated value C59H54IrN8O2[M]1099.40, experimental value 1099.38.
Ir55：1H NMR(400MHz,CDCl3) δ 8.46-8.94 (m, 4H), 7.58-7.85 (m, 6H), 7.03-7.33 (m, 6H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C65H66IrN8O2[M]1183.49, and 1183.47 as an experimental value.
Ir56：1H NMR(400MHz,CDCl3) δ 8.46-8.94 (m, 4H), 7.58-7.85 (m, 6H), 7.03-7.33 (m, 6H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C71H78IrN8O2[M]1267.59 and 1267.57.
Ir57：1H NMR(400MHz,CDCl3) δ 8.36-8.63 (m, 2H), 7.68-8.08 (m, 4H), 7.40-7.63 (m, 6H), 7.05-7.38 (m, 8H), 6.54-6.93 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.15-1.93 (m, 6H), (MS (ESI): calculated value C65H50IrN4O2[M]1111.34, 1111.32.
Ir58：1H NMR(400MHz,CDCl3) δ 8.36-8.63 (m, 2H), 7.68-8.08 (m, 4H), 7.40-7.63 (m, 6H), 7.05-7.38 (m, 8H), 6.54-6.93 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 0.96-1.35 (m, 18H) MS (ESI): calculated value C71H62IrN4O2[M]1195.45, and 1195.42.
Ir59：1H NMR(400MHz,CDCl3) δ 8.36-8.63 (m, 2H), 7.68-8.08 (m, 4H), 7.40-7.63 (m, 10H), 6.92-7.38 (m, 8H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C77H74IrN4O2[M]1279.54 and 1279.52.
Ir60：1H NMR(400MHz,CDCl3) δ 8.36-8.63 (m, 2H), 7.68-8.08 (m, 4H), 7.40-7.63 (m, 10H), 6.92-7.38 (m, 8H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C83H86IrN4O2[M]1363.64 as Experimental value 1363.62.
Ir61：1H NMR(400MHz,CDCl3) δ 8.36-8.63 (m, 4H), 7.58-8.18 (m, 8H), 7.33-7.53 (m, 6H), 6.72-7.20 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 3H), MS (ESI): calculated value C63H47IrN6O2[M]1112.34 and 1112.32 as experimental value.
Ir62：1H NMR(400MHz,CDCl3)δ8.36-8.63(m,4H),7.58-8.18(m,8H),7.33-7.53(m,6H) 6.72-7.20 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 1.28-1.49 (m, 18H), MS (ESI): calculated value C69H59IrN6O2[M]1196.43, experimental value 1196.41.
Ir63：1H NMR(400MHz,CDCl3) δ 8.36-8.63 (m, 4H), 7.88-8.06 (m, 2H), 7.65-7.82 (m, 2H), 7.33-7.63 (m, 8H), 6.90-7.20 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C75H71IrN6O2[M]1280.53, and 1280.50 as an experimental value.
Ir64：1H NMR(400MHz,CDCl3) δ 8.36-8.63 (m, 4H), 7.88-8.06 (m, 2H), 7.65-7.82 (m, 2H), 7.33-7.63 (m, 8H), 6.90-7.20 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.43 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C81H83IrN6O2[M]+:1364.62 and the experimental value: 1364.60.
Ir65：1H NMR(400MHz,CDCl3) 9.16-9.33 (m, 2H), 8.00-8.16 (m, 2H), 7.55-7.86 (m, 6H), 7.26-7.43 (m, 8H), 6.70-7.00 (m, 4H), 5.75 (s, 1H), 2.33-2.53 (m, 18H), 1.15-1.93 (m, 6H), MS (ESI): calculated value C63H47IrN6O2[M]1112.34 and 1112.32 as experimental value.
Ir66：1H NMR(400MHz,CDCl3) δ 9.16-9.33 (m, 2H), 8.00-8.16 (m, 2H), 7.55-7.86 (m, 6H), 7.26-7.43 (m, 8H), 6.70-7.00 (m, 4H), 5.75 (s, 1H), 2.28-2.53 (m, 18H), 0.96-1.35 (m, 18H), MS (ESI): calculated value C69H59IrN6O2[M]1196.43, experimental value 1196.42.
Ir67：1H NMR(400MHz,CDCl3) δ 9.16-9.33 (m, 2H), 8.00-8.16 (m, 2H), 7.55-7.86 (m, 10H), 7.26-7.43 (m, 4H), 6.90-7.22 (m, 4H), 5.76 (s, 1H), 2.28-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C75H71IrN6O2[M]1280.53, and 1280.54 as an experimental value.
Ir68：1H NMR(400MHz,CDCl3)δ9.16-9.33(m,2H),8.00-8.16(m,2H),7.55-7.86(m,10H), 7.26-7.43(m,4H),6.90-7.20(m,4H),5.76(s,1H),2.33-2.53(m,6H),1.31-1.39(m,36H) 1.05-1.28 (m, 18H), MS (ESI): calculated value C81H83IrN6O2[M]1364.62 and 1364.64 as the experimental value.
Ir69：1H NMR(400MHz,CDCl3) δ 9.14-9.33 (m, 2H), 8.43-8.63 (m, 2H), 7.96-8.17 (m, 2H), 7.55-7.86 (m, 8H), 7.28-7.43 (m, 4H), 6.82-6.95 (m, 2H), 5.73 (s, 1H), 2.28-2.53 (m, 18H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 3H), MS (ESI): calculated value C61H44IrN8O2[M]1113.32, experimental value of 1113.30.
Ir70：1H NMR(400MHz,CDCl3) δ 9.17-9.32 (m, 2H), 8.43-8.56 (m, 2H), 8.00-8.17 (m, 2H), 7.55-7.86 (m, 8H), 7.28-7.43 (m, 4H), 6.82-6.95 (m, 2H), 5.73 (s, 1H), 2.28-2.53 (m, 18H), 1.28-1.49 (m, 18H), MS (ESI): calculated value C67H56IrN8O2[M]1197.42, experimental value 1197.40.
Ir71：1H NMR(400MHz,CDCl3) δ 9.15-9.34 (m, 2H), 8.43-8.56 (m, 2H), 8.00-8.17 (m, 2H), 7.55-7.86 (m, 10H), 7.28-7.43 (m, 2H), 6.90-7.15 (m, 2H), 5.73 (s, 1H), 2.33-2.53 (m, 6H), 1.69-1.75 (m, 3H), 1.28-1.49 (m, 39H), MS (ESI): calculated value C73H68IrN8O2[M]1281.51, experimental value 1281.49.
Ir72：1H NMR(400MHz,CDCl3) δ 9.16-9.33 (m, 2H), 8.43-8.56 (m, 2H), 8.00-8.17 (m, 2H), 7.55-7.86 (m, 10H), 7.28-7.43 (m, 2H), 6.90-7.15 (m, 2H), 5.73 (s, 1H), 2.33-2.53 (m, 6H), 1.31-1.52 (m, 36H), 1.05-1.28 (m, 18H), MS (ESI): calculated value C79H80IrN8O2[M]1365.60 and 1365.61.
Example 2 preparation of Iridium Complex Ir01 organic electroluminescent device
The structure of the OLEDs device includes: a substrate, an anode, a hole injection material, a hole transport layer, an organic light emitting layer, an electron transport layer, an electron injection material, and a cathode. The substrate is glass, the anode is indium tin oxide, the hole injection layer is 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN, 5 nm), and the evaporation rate is 0.05nm/s; the hole layer adopts 4,4' -cyclohexyl di [ N, N-di (4-methylphenyl) aniline (TAPC, 50 nm), and the evaporation rate is 0.05nm/s; the electron transport layer adopts 1,3, 5-tri [ (3-pyridyl) -3-phenyl ] benzene (TmPyPb, 50 nm), and the evaporation rate is 0.05nm/s; the electron injection material is LiF (1 nm), and the evaporation rate is 0.01nm/s; the cathode is metal Al (100 nm), and the evaporation rate is 0.2nm/s; the organic light-emitting layer adopts a doping structure, is 10nm thick, and comprises a main material and a light-emitting material, wherein the main material is 2, 6-bis ((9H-carbazole-9-yl) -3, 1-phenylene) pyridine (2, 6 DCzPPy), the light-emitting material is an iridium complex Ir01, and the mass fraction of the iridium complex is 5wt%.
The iridium complexes Ir02 to Ir72 were used to prepare corresponding organic electroluminescent devices in accordance with the method described above. The properties are shown in Table 1.
TABLE 1 Performance parameters of devices prepared from the iridium complexes of the invention
The iridium complex provided by the invention can be used as a luminescent material to be applied to a luminescent layer of OLEDs, and the invention achieves the purpose of regulating and controlling the efficiency and the service life of a device by designing and optimizing the structure of a compound. As can be seen from the results of table 1 below, the iridium complex of the present invention is excellent in device performance.
While the foregoing is directed to embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow.
Claims (9)
1. An azaaromatic ring modified indolo [3,2,1-jk ] carbazole characterized by the following structure:
r1 represents a substituted or unsubstituted aromatic heterocyclic group;
r2 and R3 are the same or different and are independently selected from C1-C10 alkyl;
x represents C or N.
2. The azaaromatic ring modified indolo [3,2,1-jk ] carbazole according to claim 1, characterized in that R1 represents a pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, isoquinolyl or quinazolinyl group substituted in any position by one or more of H, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkyl, C1-C10 alkylsilyl, silyl substituted by 1-3 phenyl groups;
r2 and R3 are the same or different and are independently selected from methyl, ethyl, propyl, isopropyl, tertiary butyl, isobutyl or isoamyl.
3. The nitrogen heteroaryl ring modified indolo [3,2,1-jk ] of claim 2]Carbazole, characterized in that R1 represents a substituent substituted in any position by one or more H, methyl, methoxy, trifluoromethyl, trimethylsilyl or triphenylsilyl groups
4. An Easyplex characterized in that the azaaromatic ring-modified indolo [3,2,1-jk ] carbazole described in any one of claims 1 to 3 is used as a main ligand, and picolinic acid or a derivative thereof, pyridine phosphonic acid or a derivative thereof, tetraphenyl phosphonimide or a derivative thereof, thiotetraphenyl phosphonimide or a derivative thereof, thiopicolinic acid or a derivative thereof, amidine derivatives, 2- (5-phenyl-1, 3, 4-oxadiazole-2-) phenol or a derivative thereof, 2-phenylpyridine or a derivative thereof, 2- (2-pyridyl) -triazole or a derivative thereof, and 8- (2-pyridyl) benzofuran [2,3-b ] pyridine or a derivative thereof are used as auxiliary ligands.
5. The iridium complex according to claim 4, having the following general structural formula:
wherein R2-R5 are the same or different and are independently selected from C1-C10 alkyl.
6. The complex according to claim 5, wherein R2 to R5, which are the same or different, are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, tert-butyl, isobutyl and isopentyl.
7. An iridium complex according to claim 4, wherein the iridium complex is selected from the group consisting of:
8. use of a nitrogen heteroaromatic ring modified indolo [3,2,1-jk ] carbazole according to any of claims 1 to 3 or an iridium complex according to any of claims 4 to 7 for the preparation of phosphorescent materials.
9. Use according to claim 8, characterized in that the phosphorescent material is used for the preparation of an organic electroluminescent device.
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| JP2017092276A (en) * | 2015-11-11 | 2017-05-25 | コニカミノルタ株式会社 | Organic electroluminescent element, display device, illuminating device and aromatic heterocyclic derivative |
| CN112341500A (en) * | 2020-11-12 | 2021-02-09 | 马鞍山南大高新技术研究院有限公司 | Iridium complex with main ligand containing carbazolyl and application |
| CN114716483A (en) * | 2022-04-20 | 2022-07-08 | 季华恒烨(佛山)电子材料有限公司 | Phosphorescent iridium complex, light-emitting layer, organic electroluminescent device, and electronic apparatus |
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2022
- 2022-07-12 CN CN202210822420.2A patent/CN115260201A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017092276A (en) * | 2015-11-11 | 2017-05-25 | コニカミノルタ株式会社 | Organic electroluminescent element, display device, illuminating device and aromatic heterocyclic derivative |
| CN112341500A (en) * | 2020-11-12 | 2021-02-09 | 马鞍山南大高新技术研究院有限公司 | Iridium complex with main ligand containing carbazolyl and application |
| CN114716483A (en) * | 2022-04-20 | 2022-07-08 | 季华恒烨(佛山)电子材料有限公司 | Phosphorescent iridium complex, light-emitting layer, organic electroluminescent device, and electronic apparatus |
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