CN114456155B - Compound with azabenzene as core and application thereof - Google Patents
Compound with azabenzene as core and application thereof Download PDFInfo
- Publication number
- CN114456155B CN114456155B CN202111284332.3A CN202111284332A CN114456155B CN 114456155 B CN114456155 B CN 114456155B CN 202111284332 A CN202111284332 A CN 202111284332A CN 114456155 B CN114456155 B CN 114456155B
- Authority
- CN
- China
- Prior art keywords
- compound
- general formula
- azabenzene
- substituted
- unsubstituted
- Prior art date
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Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 40
- 239000010410 layer Substances 0.000 claims description 58
- 239000002346 layers by function Substances 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- -1 dibenzofuranyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims 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 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 230000009477 glass transition Effects 0.000 abstract description 4
- 238000004220 aggregation Methods 0.000 abstract description 2
- 230000002776 aggregation Effects 0.000 abstract description 2
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 238000005457 optimization Methods 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 239000002994 raw material Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000006757 chemical reactions by type Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a compound taking azabenzene as a core and application thereof, and belongs to the technical field of semiconductors. The compound has the structure shown in the general formula (1), has the characteristics of strong rigidity, difficult crystallization, difficult aggregation among molecules, good film forming property and high glass transition temperature and thermal stability, and can keep the stability of a film layer formed by a material and prolong the service life of an OLED device when being applied to the OLED device. Through device structure optimization, the photoelectric performance of the OLED device and the service life of the OLED device can be effectively improved.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a compound taking azabenzene as a core and application thereof.
Background
The organic electroluminescent device includes an anode, a cathode, and an organic functional layer including a light emitting layer disposed between the anode and the cathode, wherein the organic functional layer is a generic term for each layer between the cathode and the anode. In addition, a hole transport region may exist between the anode and the light emitting layer, and an electron transport region may exist between the light emitting layer and the cathode. Holes from the anode may migrate through the hole transport region to the light emitting layer and electrons from the cathode may migrate through the electron transport region to the light emitting layer. Carriers (e.g., holes and electrons) recombine in the light emitting layer and generate excitons. According to the quantum mechanics principle, the organic metal compound material can be used as a doping material to realize 100% internal quantum yield.
Nevertheless, there is still a need for improved device voltage, current efficiency and lifetime for triplet emissive phosphorescent OLEDs. In particular, higher demands are placed on the host and the doping materials in the light-emitting layer. The properties of the host material generally affect the above-mentioned key properties of the organic electroluminescent device to a large extent.
According to the prior art, carbazole-based derivatives are generally used as hole-type host materials doped with phosphorescence, and triazine-based derivatives are generally used as electron-type host materials doped with phosphorescence. The performance of the electronic host material can have a significant influence on the key performance of the organic electroluminescent device, and the existing electronic host material has improved requirements on device voltage and efficiency, especially device service life. The present invention provides an electronic type body substitute material having a low voltage, high efficiency, and especially a longer life.
For phosphorescent OLEDs, the use of a single host for the emissive layer typically results in hole and electron imbalance, severe roll-off of device efficiency at high current densities, and reduced lifetime. The invention also provides a combination of two main body materials, which can effectively solve the defects of the single main body device.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides an azabenzene-based compound and its use. The compound has an azabenzene and fluorene structure, and can effectively improve the photoelectric property of an OLED device and prolong the service life of the OLED device through device structure optimization.
The technical scheme of the invention is as follows:
a compound with azabenzene as a core has a structure shown in a general formula (1):
in the general formula (1), R 1 Represented as one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azaphenyl group, a substituted or unsubstituted azadibenzofuranyl group, a substituted or unsubstituted azacarbazolyl group;
l represents a single bond, substituted or unsubstituted C 6 -C 30 Arylene groups;
Z 1 -Z 3 each independently represents N or CH; and Z is 1 -Z 3 The number represented as N is 2 or 3;
x is O or S;
* 1. The site indicated by x 2 passes L 1 -L 4 Any two adjacent sites are connected in parallel; the dotted line indicates the presence or absence of a single bond;
R 3 represented by the general formula (3) or the general formula (4);
R a 、R b 、R c 、R d represented independently of each other as hydrogen atom, C 1 -C 10 Alkyl or C of (2) 6 -C 30 An aryl group;
the substituents mentioned for "substituted or unsubstituted" are optionally selected from deuterium, tritium, halogen atoms, cyano groups, C 1 -C 20 Alkyl, C of (2) 6 -C 20 Aryl, C having one or more hetero atoms 2 -C 20 One or more of heteroaryl;
the heteroatoms in the heteroaryl group are selected from nitrogen, oxygen or sulfur.
Preferably, the structure of the compound is shown as any one of the general formula (2-1) -general formula (2-6):
Z 1 -Z 3 、R 1 、R 3 the meanings of L, X and dashed lines are as defined above.
Preferably, the L represents a single bond or phenylene; r is R a 、R b 、R c 、R d Independently of each other, is represented by a hydrogen atom, methyl, ethyl, isopropyl, tert-butyl, phenyl or biphenyl;
the "substituted or unsubstituted" substituents are optionally selected from one or more of deuterium, tritium, fluorine atom, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, hexyl, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl or pyridyl.
Preferably, the specific structure of the compound is any one of the following structures:
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an organic electroluminescent device comprises a cathode, an anode and a functional layer, wherein the functional layer is positioned between the cathode and the anode, and at least one functional layer in the organic electroluminescent device contains the compound taking azabenzene as a core.
Preferably, the functional layer comprises a light-emitting layer, and the light-emitting layer contains the compound taking the azabenzene as a core.
Preferably, the functional layer comprises a light-emitting layer, the light-emitting layer comprises a host material and a guest material, and the host material contains the compound taking the azabenzene as a core.
A lighting or display element comprising said organic electroluminescent device.
Compared with the prior art, the invention has the beneficial technical effects that:
(1) The LUMO distribution of the compound is sufficiently separated from the domain due to pi conjugation effect and a rigid plane, so that the compound has strong electron transmission capability, high radiation transition rate and good excitation state stability; the high electron transmission rate can reduce the initial voltage of the device, and the high radiation transition rate and the good excited state stability are beneficial to improving the efficiency and the service life of the device;
(2) The introduction of fluorene groups increases the asymmetry of molecules and can reduce the crystallinity of the molecules;
(3) The compound provided by the invention has deep HOMO and LUMO energy levels and high electron mobility, and the higher T1 energy level can ensure the energy transfer efficiency between a host and a guest, so that the compound can be used as an electronic luminescent main material;
(4) The compound has the characteristics of high rigidity, difficult crystallization, difficult aggregation among molecules, good film forming property and high glass transition temperature and thermal stability, so that the compound can keep the stability of a film layer formed by a material and prolong the service life of an OLED device when being applied to the OLED device. After the compound is used as an organic electroluminescent functional layer material to be applied to an OLED device, the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the OLED light-emitting device is obviously prolonged, and the OLED light-emitting device has a good application effect and good industrialization prospect.
Drawings
FIG. 1 is a schematic diagram of the structure of an OLED device using the materials of the present invention;
wherein 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a CPL layer.
Detailed Description
C as used herein 6 -C 30 Aryl refers to a monovalent group comprising a carbocyclic aromatic system having from 6 to 30 carbon atoms as ring-forming atoms, C as used herein 6 -C 30 Arylene refers to a divalent group comprising a carbocyclic aromatic system having 6 to 30 carbon atoms as ring forming atoms. C (C) 6 -C 30 Non-limiting examples of aryl groups may include phenyl, biphenyl, phenanthryl, terphenyl, naphthyl, and the like. C (C) 6 -C 30 Non-limiting examples of arylene groups may includePhenylene, biphenylene, phenanthrylene, biphenylene, naphthylene, and the like. When C 6 -C 30 Aryl and/or C 6 -C 30 Where the arylene group includes two or more rings, the rings may be fused to each other.
Herein, C is used 6 -C 20 Aryl refers to a monovalent group comprising a carbocyclic aromatic system having from 6 to 20 carbon atoms as ring-forming atoms. C (C) 6 -C 20 Non-limiting examples of aryl groups may include phenyl, biphenyl, phenanthryl, terphenyl, naphthyl, and the like. When C 6 -C 20 Where the aryl group includes two or more rings, the rings may be fused to each other.
In this context, C is used 2 -C 20 Heteroaryl refers to a monovalent group comprising a carbocyclic aromatic system having at least one heteroatom selected from N, O and S and 2 to 20 carbon atoms as ring forming atoms. C (C) 2 -C 20 Non-limiting examples of heteroaryl groups can include pyridyl, oxadiazolyl, triazinyl, pyrimidinyl, furyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, dibenzooxazolyl, carbazolyl, N-phenylcarbazolyl, and the like. When C 2 -C 20 Where the heteroaryl group includes two or more rings, the rings may be fused to each other.
Herein, C 1 -C 20 Alkyl refers to a group of a saturated aliphatic hydrocarbon having 1 to 20 carbon atoms and which may be branched or straight chain. C (C) 1 -C 20 Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1, 2-dimethylpropyl, hexyl, and the like. Of these alkyl groups, C is particularly preferred 1 -C 4 An alkyl group.
The raw materials involved in the synthetic embodiment of the invention are purchased from medium energy conservation Wanchun stock Co.
EXAMPLE 1 Synthesis of Compound 2
In a flask, starting material A1 (20 mmol), starting material B1 (24 mmol), pd (PPh) 3 ) 4 (1.0 mmol) and K 2 CO 3 (55 mmol) dissolved in toluene, ethanol and H 2 After addition of the mixture of O, the mixture was refluxed at 120℃for 24 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, dried and separated by column chromatography to give compound 2 (yield: 45.3%).
The preparation method of the raw material A1 comprises the following steps:
in a three-necked flask, under the protection of nitrogen gas, 0.012mol of raw material a1,0.01mol of raw material b1 and 150ml of toluene were added and mixed with stirring, and then 5X 10 was added -5 mol Pd 2 (dba) 3 ，5×10 -5 Reflux reaction is carried out for 12 hours on 0.03mol of sodium tert-butoxide by mol of tri-tert-butyl phosphorus, a sampling point plate is adopted, no amino compound remains, and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column (silica gel 100-200 mesh, eluent is chloroform: n-hexane=30:70 (volume ratio)) to obtain intermediate c1; elemental analysis structure (C) 21 H 13 BrN 4 ) The method comprises the steps of carrying out a first treatment on the surface of the Test value: c,62.88; h,3.27; br,19.90; n,13.96.MS (m+): 400.14.
0.02mol of intermediate c1, 0.024mol of pinacol bisborate, 0.6mmol of 1,1' -bis (diphenylphosphine) -ferrocene-palladium (II) dichloride dichloromethane complex, 60mmol of potassium acetate and 79ml of toluene are reacted for 16 hours under reflux, cooled, 26ml of water are added, stirring is carried out for 30 minutes, the organic phase is separated, filtration is carried out through celite, the organic solvent is subsequently distilled off, the crude product obtained is recrystallized in heptane/toluene to obtain raw material A1, purity 99.83% and yield 81.4%; elemental analysis structure (C) 27 H 25 BN 4 O 2 )；MS(M+)：448.21。
The preparation method of the raw material A8 comprises the following steps:
under argon atmosphere, 0.015mol of a material a8, 0.015mol of a material b8, 0.3mmol of tetra (triphenylphosphine) palladium, 43ml of toluene and 21ml of sodium carbonate aqueous solution (2M) are added into a flask, reflux reaction is carried out for 8 hours, cooling is carried out to room temperature, toluene extraction is carried out, an organic phase is washed by saturated saline solution, and after the organic phase is dried, column chromatography is carried out for purification, thus obtaining an intermediate c8; elemental analysis structure (C) 39 H 25 BrN 4 ) The method comprises the steps of carrying out a first treatment on the surface of the Test value: c,74.40; h,4.00; br,12.70; n,8.95.MS (m+): 628.41.
0.02mol of intermediate c8, 0.024mol of pinacol bisborate, 0.6mmol of 1,1' -bis (diphenylphosphine) -ferrocene-palladium (II) dichloride dichloromethane complex, 60mmol of potassium acetate and 79ml of toluene are reacted for 16 hours under reflux, cooled, 26ml of water are added, stirring is carried out for 30 minutes, the organic phase is separated off, filtration is carried out through celite, the organic solvent is subsequently distilled off, and the crude product obtained is recrystallized in heptane/toluene to give raw material A8 with a purity of 99.90% and a yield of 80.3%. Elemental analysis structure (C) 45 H 37 BN 4 O 2 )；MS(M+)：676.44。
The preparation of starting material A for the preparation of the compounds according to the invention is similar to that of starting materials A1 and A8.
The preparation method of the raw material B1 comprises the following steps:
to a round bottom flask was added 95mmol of raw material n1, 112mmol of 1-bromo-2-iodobenzene and 320ml of toluene to dissolve, then 117ml of an aqueous solution in which 141.5mmol of potassium carbonate was dissolved and stirred, 0.95mmol of tetraphenylphosphine palladium was added thereto and the mixture was stirred under reflux under nitrogen atmosphere for 12 hours. After the reaction was completed, extraction was performed with ethyl acetate, the extract was dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography on silica gel using n-hexane/dichloromethane (9:1 by volume) to give intermediate s1.
In a round-bottomed flask, 70mmol of intermediate s1 was added, 200ml of anhydrous diethyl ether was added to dissolve it, cooled to-78 ℃, stirred under nitrogen atmosphere, 31ml (78 mmol) of a 2.5M n-butyllithium n-hexane solution was slowly added thereto, then stirred under nitrogen atmosphere at-78 ℃ for 2 hours, 70mmol of benzophenone dissolved in 100ml of anhydrous tetrahydrofuran was slowly added thereto, then stirred under room temperature and nitrogen atmosphere for 8 hours, the reaction solution was cooled to 0 ℃, 250ml of a 1.0M ammonium chloride aqueous solution was added thereto, extracted with diethyl ether, the organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography eluting with 10% ethyl acetate/n-hexane solution to give intermediate p1.
60mmol of intermediate p1 was added to a round-bottomed flask, dissolved by adding 236ml of anhydrous methylene chloride, cooled to 0℃and stirred under nitrogen atmosphere, 57.4mmol of boron trifluoride diethyl ether was slowly added thereto, and then stirred under nitrogen atmosphere at room temperature for 4 hours. The reaction solution was cooled to 0 ℃, a small amount of distilled water was added to terminate the reaction, then 60ml of 1.0m aqueous sodium bicarbonate solution was added, extracted with dichloromethane, the extract was dried over magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by column chromatography on silica gel using n-hexane/dichloromethane (9:1 by volume) to give starting material B1 as the target compound.
The preparation method of the raw material B2 comprises the following steps:
the reaction type involved is the same as that of the preparation of the starting material B1.
The preparation method of the raw material B3 comprises the following steps:
the reaction type involved is the same as that of the preparation of the starting material B1.
The preparation method of the raw material B4 comprises the following steps:
the reaction type involved is the same as that of the preparation of the starting material B1.
The preparation of other starting materials B involves the starting materials shown in table 1 below:
TABLE 1
The following preparation examples 2 to 18 refer to the same reaction type as in preparation example 1, and the occurrence of the same reactant in different preparation examples is indicated by different code numbers, and the test results of the raw materials A and B and the prepared compounds referred to in preparation examples 1 to 18 are shown in Table 2.
TABLE 2
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The compound of the invention is used in a light-emitting device and can be used as a light-emitting layer material. The compounds prepared in the above examples of the present invention were subjected to physical and chemical properties, and the test results are shown in table 3:
TABLE 3 Table 3
Note that: triplet energy level T1 is tested by a fluorescent-3 series fluorescence spectrometer of Horiba, and the test condition of the material is 2 x 10 -5 A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter) at a heating rate of 10 ℃/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy measurement system (IPS-3), tested as an atmospheric environment; eg was tested by a two-beam uv-vis spectrophotometer (model: TU-1901), lumo=homo+eg.
As can be seen from the data in the table, the organic compound has high glass transition temperature, can be applied to improving the phase stability of a material film, and further improves the service life of a device; the organic compound provided by the invention has proper HOMO and LUMO energy levels, so that the problem of carrier injection can be solved, and the device voltage can be reduced. The organic compound has higher T1 energy level, and can ensure the energy transfer efficiency between the main body and the guest body as a main body material. Therefore, after the organic material is applied to the light-emitting layer of the OLED device, the voltage of the device can be effectively reduced, and the service life of the device can be prolonged.
The effect of the OLED materials synthesized according to the present invention in the application to devices will be described in detail below with reference to device examples 1 to 36 and device comparative examples 1 to 8. The device examples 2 to 36 and the device comparative examples 1 to 8 of the present invention were identical in the manufacturing process of the device as compared with the device example 1, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept uniform, except that the light-emitting layer material in the device was replaced.
Device example 1
As shown in fig. 1, the transparent substrate layer 1 is a transparent PI film, and the anode layer 2 (ITO (15 nm)/Ag (150 nm)/ITO (15 nm)) is washed, that is, sequentially washed with a cleaning agent (SemiClean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, the film thickness was 10nm, and the mass ratio of HT-1 and P-1 was 97:3. Next, HT-1 was evaporated as a hole transport layer 4, with a thickness of 130nm. EB-1 was then evaporated as an electron blocking layer 5, 40nm thick. After the evaporation of the electron blocking layer material is completed, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises a compound 2 used by the OLED light emitting layer 6 as a main material, GD-1 as a doping material, the doping proportion of the doping material is 6% (mass ratio), and the film thickness of the light emitting layer is 40nm. After the light-emitting layer 6 was deposited, vacuum deposition of HB-1 was continued to give a film thickness of 5nm, and this layer was a hole blocking layer 7. After the hole blocking layer 7, vacuum evaporation is continued to carry out on ET-1 and Liq, the mass ratio of ET-1 to Liq is 1:1, the film thickness is 35nm, and the electron transport layer 8 is formed. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, mg having a film thickness of 15nm was produced by a vacuum vapor deposition apparatus: the mass ratio of Mg to Ag in the Ag electrode layer is 1:9, and the Ag electrode layer is used as the cathode layer 10. On the cathode layer 10, a CPL layer 11 was formed by vacuum deposition of CP-1, and the thickness was 70nm. The organic electroluminescent device 1 is obtained.
Device examples 2 to 18 and device comparative examples 1 to 4 were prepared in the same manner as device example 1, except that the compounds in Table 1 were used as host materials; device examples 19 to 36 and device comparative examples 5 to 8 were prepared in the same manner as in device example 1, except that the compounds in table 1 and GH2 were used as host materials, GD-1 was used as dopant material, and the mass ratio of the three was the compounds in table 1: GH2: GD-1=47:47:6 (mass ratio).
The molecular structural formula of the related material is shown as follows:
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after completing the OLED light emitting device as described above, the anode and cathode were connected by a well-known driving circuit, and the voltage, current efficiency, light emission spectrum, and life of the device were measured. Examples of devices prepared in the same manner and comparative examples are shown in table 4; the voltage, current efficiency, color and 20mA/cm of the resulting device 2 The test results of the LT95 lifetime are shown in table 5.
TABLE 4 Table 4
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TABLE 5
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Note that: the voltage, current efficiency and color coordinates are at a current density of 10mA/cm 2 Tested under conditions, an IVL (current-voltage-brightness) test system (fexostat scientific instruments, su); the life test system is an EAS-62C OLED device life tester of Japanese system technical research company; LT95 means at 20mA/cm 2 The time taken for the brightness of the device to decay to 95% is now described.
As can be seen from the device data results of table 5, the organic light emitting device of the present invention achieves a greater improvement in both device efficiency and device lifetime compared to the OLED devices of known materials, as compared to device comparative examples 1-8. Meanwhile, the organic light emitting device of the present invention has a reduced voltage compared to OLED devices of known materials.
In summary, the above embodiments are only preferred embodiments of the present invention, and are not intended to limit the present invention, but any modifications, equivalent substitutions, improvements, etc. within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (7)
1. A compound taking azabenzene as a core is characterized in that the structure of the compound is shown as a general formula (1):
in the general formula (1), R 1 Represented as one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, and a substituted or unsubstituted azaphenyl group;
l represents a single bond or phenylene;
Z 1 -Z 3 each independently represents N or CH; and Z is 1 -Z 3 The number represented as N is 2 or 3;
x is O or S;
* 1. The site indicated by x 2 passes L 1 -L 2 ，L 3 -L 4 Two sites are connected in parallel; the dotted line indicates the presence or absence of a single bond;
R 3 represented by the general formula (3) or the general formula (4);
R a 、R b 、R c 、R d each independently represents a hydrogen atom, a phenyl group or a biphenyl group;
the "substituted or unsubstituted" substituents are optionally selected from one or more of deuterium, cyano, phenyl, naphthyl, naphthyridinyl, biphenyl, terphenyl, or pyridyl.
2. The compound according to claim 1, wherein the compound has a structure represented by any one of the general formula (2-1) -general formula (2-6):
Z 1 -Z 3 、R 1 、R 3 the meanings of L, X and dashed lines are as defined in claim 1.
3. The compound according to claim 1, wherein the specific structure of the compound is any one of the following structures:
4. an organic electroluminescent device comprising a cathode, an anode and a functional layer, wherein the functional layer is located between the cathode and the anode, characterized in that at least one functional layer in the organic electroluminescent device comprises the azabenzene-based compound according to any one of claims 1 to 3.
5. The organic electroluminescent device according to claim 4, wherein the functional layer comprises a light-emitting layer, wherein the light-emitting layer contains the azabenzene-based compound according to any one of claims 1 to 3.
6. The organic electroluminescent device according to claim 4, wherein the functional layer comprises a light-emitting layer, wherein the light-emitting layer comprises a host material and a guest material, and the host material contains the azabenzene-based core compound according to any one of claims 1 to 3.
7. A lighting or display element, characterized in that it comprises an organic electroluminescent device as claimed in any one of claims 4 to 6.
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Country or region after: China Address after: B312-194, No. 2 Fengwei Road, Huizhi Enterprise Center, Xishan Economic and Technological Development Zone, Xishan District, Wuxi City, Jiangsu Province, 214101 Applicant after: Jiangsu March Technology Co.,Ltd. Address before: 214112 No.210 Xinzhou Road, Wuxi City, Jiangsu Province Applicant before: Jiangsu March Technology Co.,Ltd. Country or region before: China |
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| GR01 | Patent grant | ||
| GR01 | Patent grant |