CN116903600A - Condensed ring compound and organic electroluminescent device thereof - Google Patents
Condensed ring compound and organic electroluminescent device thereof Download PDFInfo
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- CN116903600A CN116903600A CN202310797451.1A CN202310797451A CN116903600A CN 116903600 A CN116903600 A CN 116903600A CN 202310797451 A CN202310797451 A CN 202310797451A CN 116903600 A CN116903600 A CN 116903600A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 205
- 239000010410 layer Substances 0.000 claims abstract description 101
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 44
- 229910052805 deuterium Inorganic materials 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
- 239000012044 organic layer Substances 0.000 claims description 25
- 229910052705 radium Inorganic materials 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 54
- 230000005540 biological transmission Effects 0.000 abstract description 11
- 230000002035 prolonged effect Effects 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 230000004888 barrier function Effects 0.000 abstract description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 3
- 239000002346 layers by function Substances 0.000 abstract description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 3
- -1 alkenyl radical Chemical class 0.000 description 303
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 109
- 230000015572 biosynthetic process Effects 0.000 description 98
- 238000003786 synthesis reaction Methods 0.000 description 96
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 84
- 238000002360 preparation method Methods 0.000 description 58
- 238000004128 high performance liquid chromatography Methods 0.000 description 56
- 238000001819 mass spectrum Methods 0.000 description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 48
- 239000004305 biphenyl Substances 0.000 description 42
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 41
- 235000010290 biphenyl Nutrition 0.000 description 40
- 125000001624 naphthyl group Chemical group 0.000 description 31
- 229940125904 compound 1 Drugs 0.000 description 30
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 29
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 26
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 26
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 20
- 230000000903 blocking effect Effects 0.000 description 20
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- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 description 18
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
- 125000005561 phenanthryl group Chemical group 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 16
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 16
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 16
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 15
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 13
- 125000004076 pyridyl group Chemical group 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 125000002541 furyl group Chemical group 0.000 description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 11
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 125000000335 thiazolyl group Chemical group 0.000 description 11
- 125000001544 thienyl group Chemical group 0.000 description 11
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 125000002883 imidazolyl group Chemical group 0.000 description 10
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 10
- 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 10
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 10
- 125000002971 oxazolyl group Chemical group 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 125000003373 pyrazinyl group Chemical group 0.000 description 9
- 125000002098 pyridazinyl group Chemical group 0.000 description 9
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 9
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 8
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 7
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229940127113 compound 57 Drugs 0.000 description 7
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 7
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 5
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
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- 238000001953 recrystallisation Methods 0.000 description 5
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 4
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- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 3
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
The invention provides a condensed ring compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials. The fused ring compound provided by the invention has proper HOMO and LUMO energy levels, can be matched with the energy levels of adjacent functional layers, can reduce the transmission barrier of electrons, and reduces the driving voltage of an organic electroluminescent device; the organic electroluminescent device has good electron transmission performance, can balance hole and electron transmission, enables excitons to be effectively recombined, and improves the driving voltage of the organic electroluminescent device; the electron transport layer can also prevent holes from migrating to one side of the electron transport layer, so that excitons are prevented from being recombined at an interface to cause efficiency roll-off and service life is shortened; meanwhile, the fused ring compound has good thermal stability and chemical stability, and the film has excellent stability, so that the service life of the device can be prolonged.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a condensed-cyclic compound and an organic electroluminescent device thereof.
Background
An Organic Light-Emitting Diode (OLED) has the characteristics of high brightness, wide material selection range, low driving voltage, active Light emission and the like, and has the advantages of high definition, wide viewing angle, high response speed and the like, and is a popular research field in recent decades.
An organic electroluminescent device is a device that changes electric energy into light by applying electricity to an organic electroluminescent material. Organic electroluminescent devices currently include an anode, a cathode, and a structure of an organic layer between the anode and the cathode. The organic layer of the OLED may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer (which includes a host and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. Applying voltage to the OLED, injecting holes into the light-emitting layer from the anode, injecting electrons into the light-emitting layer from the cathode, combining the holes and the electrons in the organic layer to form excitons, releasing energy, simultaneously transmitting the energy to organic luminescent material molecules to enable the organic luminescent material molecules to transition from a ground state to an excited state, and generating a luminescent phenomenon by the excited molecules after radiation transition from the excited state to the ground state due to unstable excited states.
The most important factor determining the luminous efficiency in an OLED is the luminescent material. The light-emitting material is required to have high quantum efficiency, high electron mobility, high hole mobility, and other characteristics, and uniformity and stability in vapor deposition film formation. The luminescent material can be further divided into a host and a dopant material according to its function, the host material plays a vital role in the luminescent material, and on the one hand, the host material needs to act as a solid solvent and an energy transfer agent, which requires the host material to have a high purity and a suitable molecular weight for vacuum deposition; in addition, the host material needs to have a high glass transition temperature and a high thermal decomposition temperature to achieve thermal stability, and needs to have high chemical, electrical stability to achieve long service life. Therefore, development of a light-emitting host material having excellent characteristics is urgently required, and further, the light-emitting efficiency and the lifetime of the OLED are improved.
Whether or not the carrier transport in an OLED is balanced is also an important factor affecting the luminous efficiency. Because of the great difference between the hole mobility and the electron mobility, the hole and electron transmission in the OLED are difficult to balance, so that excitons are combined at the edge of the light-emitting layer, the light-emitting efficiency of the OLED is reduced, and the development of the OLED is severely restricted, therefore, development of materials with excellent performance is urgently needed, the hole and electron transmission of the materials are balanced, the driving voltage of the OLED is reduced, the light-emitting efficiency of the OLED is improved, and the service life of the OLED is prolonged.
Disclosure of Invention
In order to solve the above problems, the present invention is directed to a condensed-cyclic compound and an organic electroluminescent device thereof, which can reduce the driving voltage of an OLED, improve the luminous efficiency of the OLED, and prolong the service life.
The specific scheme is as follows:
the invention provides a fused ring compound selected from the structures represented by formula I:
in the formula I, Y is selected from any one of O atom, S atom, C (Ra) (Rb) and N (Rc);
the ring E is selected from any one of the groups represented by the formulas II-1 to II-7:
in formulas II-1 to II-7, any two adjacent "×" represent bonding sites;
The R is 1 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or said R 1 Can be combined with L 0 Direct bonding;
said n 1 Selected from 0, 1 or 2;
q is independently selected from CH or N atoms, and L 0 Q at the junction is selected from a C atom, and at most two Q in each of the structures of formulas II-1 to II-7 are selected from an N atom;
the R is 2 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
said n 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said n 3 Selected from 0, 1, 2, 3, 4, 5 or 6, said n 4 Selected from 0, 1, 2, 3 or 4; having two or more R' s 2 When present, two or more R' s 2 Identical or different from each other, or adjacent two R' s 2 Form a substituted or unsubstituted ring;
the Ra and Rb are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or Ra, rb form a substituted or unsubstituted ring;
the Rc is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the X is independently selected from C (R 0 ) Or an N atom; and up to three X are selected from N atoms, and L 0 、L 1 、L 2 X at the junction is selected from C atoms;
the R is 0 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or adjacent R 0 Form a substituted or unsubstituted ring;
the Ar is as follows 1 、Ar 2 At least one of the groups represented by formula III, and the rest is any one selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
in formula III, the Z 1 Independently selected from C (R) 3 ) Or N atom, with L 1 、L 2 Z at the junction 1 Selected from the group consisting of C atoms;
the ring M is selected from a group represented by a formula III-1 or a formula III-2, and two adjacent ". Times. -bonds represent condensed sites;
the Z is 2 Independently selected from C (R) 3 ) Or an N atom, and one or two Z's in formula III-1 2 Selected from N atoms, and L 1 、L 2 Z at the junction 2 Selected from C atoms；
The Z is 3 Independently selected from C (R) 4 ) Or N atom, with L 1 、L 2 Z at the junction 3 Selected from the group consisting of C atoms; the Y is 1 Independently selected from any one of O atom, S atom, C (RdRe) and N (Rf);
the R is 3 、R 4 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R 3 Form a substituted or unsubstituted ring;
the Rd and Re are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or Ra, rb form a substituted or unsubstituted ring;
the Rf is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the L is 0 、L 1 、L 2 Independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted heteroarylene.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises at least one or more than one condensed-cyclic compound.
Advantageous effects
The fused ring compound provided by the invention has proper HOMO and LUMO energy levels, can be matched with the energy levels of adjacent functional layers, can reduce the transmission barrier of electrons, and reduces the driving voltage of an organic electroluminescent device; the condensed ring compound also has better electron transmission property, can reach balance with hole transmission, and enables excitons to be effectively recombined; meanwhile, the organic electroluminescent device has a higher triplet state energy level, can block holes from migrating to one side of the electron transport layer, and simultaneously assists the electron transport layer to regulate electron transport, so that excitons are prevented from being recombined at an interface of the luminescent layer, efficiency roll-off is avoided, driving voltage of the organic electroluminescent device is further reduced, luminous efficiency is improved, and service life is prolonged.
Meanwhile, the fused ring compound provided by the invention has high glass transition temperature, good thermal stability and chemical stability, and after vapor deposition film formation, the film has good stability and is not easy to crystallize, and when the fused ring compound is applied to an organic electroluminescent device, the service life of the device can be prolonged.
Detailed Description
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. Modifications of the invention which are obvious to those skilled in the art are intended to fall within the scope of the invention.
In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance.
In the specification, "-" means a moiety attached to another substituent. "-" may be attached at any optional position of the attached group/fragment. For exampleRepresentation->And so on.
In the present invention, when the position of the substituent on the ring is not fixedMeaning that it can be attached to any of the corresponding selectable positions of the loop. For example, the number of the cells to be processed,can indicate->Can representCan represent And so on.
Examples of the halogen atom according to the present invention may include fluorine, chlorine, bromine and iodine.
The alkyl group according to the present invention is a monovalent group of an alkane molecule from which one hydrogen atom is removed, and may be a straight chain alkyl group or a branched chain alkyl group, and preferably has 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples may include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, and the like.
Alkenyl in the context of the present invention means a monovalent radical of an olefin molecule from which one hydrogen atom has been removed, which may be a straight-chain alkenyl or branched alkenyl radical, preferably having from 2 to 15 carbon atoms, more preferably from 2 to 12 carbon atoms, particularly preferably from 2 to 6 carbon atoms. Specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthalen-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, styryl, and the like, but are not limited thereto.
Cycloalkyl according to the invention is understood to mean a monovalent radical of a cyclic alkane molecule from which one hydrogen atom has been removed, preferably having 3 to 12 carbon atoms, more preferably having 3 to 10 carbon atoms, particularly preferably having 3 to 6 carbon atoms. Examples may include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, and the like.
Silyl groups according to the invention can be prepared from-SiH 3 The radicals mentioned are indicated; the substituted silyl group according to the present invention may be represented by a group described as-Si (Rs) (Rs) (Rs), rs may be one, two or three, and Rs is hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group described above, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group or the like, and is not hydrogen at the same time; the plurality of Rs in Si (Rs) (Rs) (Rs) may be the same or different; preferably having 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 1 to 22 carbon atoms, and most preferably 1 to 18 carbon atoms, examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethylt-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, terphenylsilyl, tripyridylsilyl, and the like, but are not limited thereto.
Aryl as used herein refers to a monovalent radical of an aromatic hydrocarbon molecule with one hydrogen removed from the aromatic nucleus carbon and may be a monocyclic, polycyclic or fused ring aryl group, preferably having from 6 to 60 carbon atoms, more preferably from 6 to 30 carbon atoms, particularly preferably from 6 to 18 carbon atoms, and most preferably from 6 to 12 carbon atoms. Examples may include phenyl, biphenyl, terphenyl, tetrabiphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, triphenylenyl, perylene, phenylnaphthyl, phenylphenanthryl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9' -spirobifluorenyl, benzofluorenyl, and the like, but are not limited thereto.
Heteroaryl according to the present invention refers to a monovalent group obtained by substituting one or more aromatic nucleus carbon atoms in an aromatic hydrocarbon molecule with heteroatoms including, but not limited to, oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, most preferably 2 to 12 carbon atoms. Examples may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, N-heterobenzothienyl, N-heterobenzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, N-heterodibenzofuranyl, benzodibenzofuranyl, dibenzofuranyl, dibenzothienyl, dibenzothiazyl, carbazolyl, N-heterocarbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, spirofluorenyl, spirofluorene, and the like, but are not limited thereto.
Arylene as used herein refers to an aryl group having 2 binding sites, i.e., a divalent group. These are not only divalent groups but also aryl groups as described above.
Heteroaryl ene in the sense of the present invention means that there are 2 binding sites, i.e. divalent groups, on the heteroaryl group. They may be applied to the above description of heteroaryl groups, in addition to the divalent groups, respectively.
The aliphatic ring according to the present invention is a cyclic hydrocarbon and its derivative formed by intramolecular condensation of a chain hydrocarbon and its derivative, and may be a cycloalkane, cycloalkene, cycloalkyne, or the like, preferably 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, particularly preferably 3 to 10 carbon atoms, and most preferably 3 to 7 carbon atoms, and specific examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclohexanol, cyclohexanone, or the like, but are not limited thereto.
"substituted … …" as used herein, such as "substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene" refers to an independent mono-or poly-substitution with: deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C1-C12 alkylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, and the like, but are not limited thereto, and when two or more substituents are present, adjacent substituents may be linked to form a ring. Preferably mono-or polysubstituted by: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuteromethyl, ethyl, isopropyl, t-butyl, deuterated t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, deuterophenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, anthracenyl, phenanthryl, triphenylene, perylenyl, pyrenyl, benzyl, t-butyl substituted phenyl, adamantyl substituted phenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9' -spirobifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazinyl, carbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophenyl, phenoxazinyl, and the like, but not limited thereto.
The term "link-forming ring" as used herein means that two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:
in the present invention, the ring formed by the connection may be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of both, and the ring formed by the connection may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentaacene, cyclohexene, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
"Spiro" as used herein refers to structures in which two carbocycles share one carbon atom, and preferably have 15 to 60 carbon atoms, more preferably 15 to 30 carbon atoms. In particular, the spiro structure may include any of the substituted or unsubstituted groups of the following structural formula:
the invention provides a fused ring compound selected from the structures represented by formula I:
in the formula I, Y is selected from any one of O atom, S atom, C (Ra) (Rb) and N (Rc);
the ring E is selected from any one of the groups represented by the formulas II-1 to II-7:
In formulas II-1 to II-7, any two adjacent "×" represent bonding sites;
the R is 1 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or said R 1 Can be combined with L 0 Direct bonding;
said n 1 Selected from 0, 1 or 2;
q is independently selected from CH or N atoms, and L 0 Q at the junction is selected from a C atom, and at most two Q in each of the structures of formulas II-1 to II-7 are selected from an N atom;
the R is 2 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
said n 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said n 3 Selected from 0, 1, 2, 3, 4, 5 or 6, said n 4 Selected from 0, 1, 2, 3 or 4; having two or more R' s 2 When present, two or more R' s 2 Identical or different from each other, or adjacent two R' s 2 Form a substituted or unsubstituted ring;
the Ra and Rb are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or Ra, rb form a substituted or unsubstituted ring;
the Rc is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the X is independently selected from C (R 0 ) Or an N atom; and up to three X are selected from N atoms, and L 0 、L 1 、L 2 X at the junction is selected from C atoms;
the R is 0 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or adjacent R 0 Form a substituted or unsubstituted ring;
the Ar is as follows 1 、Ar 2 At least one of the groups represented by formula III, and the rest is any one selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
in formula III, the Z 1 Independently selected from C (R) 3 ) Or N atom, with L 1 、L 2 Z at the junction 1 Selected from the group consisting of C atoms;
the ring M is selected from a group represented by a formula III-1 or a formula III-2, and two adjacent ". Times. -bonds represent condensed sites;
the Z is 2 Independently selected from C (R) 3 ) Or an N atom, and one or two Z's in formula III-1 2 Selected from N atoms, and L 1 、L 2 Z at the junction 2 Selected from the group consisting of C atoms;
the Z is 3 Independently selected from C (R) 4 ) Or N atom, with L 1 、L 2 Z at the junction 3 Selected from the group consisting of C atoms; the Y is 1 Independently selected from any one of O atom, S atom, C (RdRe) and N (Rf);
the R is 3 、R 4 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R 3 Form a substituted or unsubstituted ring;
the Rd and Re are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or Ra, rb form a substituted or unsubstituted ring;
the Rf is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the L is 0 、L 1 、L 2 Independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted heteroarylene.
Preferably, the ""up to three X's are selected from the group consisting of N atoms; further preferred, said->"up to two X's are selected from the group consisting of N atoms; also preferably, the->"at most one X is selected from the group consisting of N atoms.
Preferably, the ""any one selected from the following groups:
the m is 1 Independently selected from 0, 1, 2 or 3, said m 2 Independently selected from 0, 1 or 2.
Preferably, the condensed-cyclic compound is selected from any one of structures represented by the following formulas IV-1 to IV-6:
the Y, ring E, R 1 、R 0 、L 0 、L 1 、L 2 、Ar 1 、Ar 2 、n 1 Is as defined in formula I;
the m is 1 Independently selected from 0, 1, 2 or 3, said m 2 Independently selected from 0, 1 or 2.
Preferably, the formula IV-1 is selected from any one of the structures shown below:
preferably, the formula IV-2 is selected from any one of the structures shown below:
preferably, the formula IV-3 is selected from any one of the structures shown below:
preferably, the formula IV-4 is selected from any one of the structures shown below:
preferably, said R 0 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo9, 9-dimethylfluorenyl, benzo9, 9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, Deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylenyl, deuterated pyridinyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted naphthyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted biphenyl ethyl substituted naphthyl, isopropyl substituted phenyl, isopropyl substituted biphenyl, isopropyl substituted naphthyl, tert-butyl substituted adamantyl, tert-butyl substituted phenyl, tert-butyl substituted biphenyl, tert-butyl substituted naphthyl, tert-butyl substituted phenanthryl, tert-butyl substituted 9, 9-dimethylfluorenyl, tert-butyl substituted 9, 9-diphenylfluorenyl, tert-butyl substituted 9,9' -spirobifluorenyl, trimethylsilyl substituted phenyl, triethylsilyl substituted phenyl, trimethylsilyl substituted biphenyl, triphenylsilyl substituted phenyl, adamantyl substituted biphenyl, norbornyl substituted phenyl, norbornyl substituted biphenyl, deuteromethyl substituted phenyl, deuteromethyl substituted biphenyl, deuteromethyl substituted isopropyl substituted phenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted phenyl, deuterated tert-butyl-substituted biphenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, the saidSelected from any one of the following groupsMeaning a: />
Said n 1 Independently selected from 0, 1 or 2, said n 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said n 3 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said n 4 Independently selected from 0, 1, 2, 3 or 4, said n 5 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said n 6 Independently selected from 0, 1, 2, 3, 4 or 5, said n 7 Independently selected from 0, 1, 2 or 3.
Preferably, at most two Q's in each of the above groups are selected from N atoms, or at most one Q in each of the above groups is selected from N atoms.
Preferably, said R 1 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropyl, cyclobutanyl, cyclopentanyl, cyclohexenyl, cycloheptanyl, adamantyl, norbornyl, phenyl, biphenyl, and terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, and their derivatives benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl, benzofuran, Benzimidazolyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deuteroisopropyl, deutero-n-butyl, deuteroisobutyl, deutero-sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylyl, deuterated pyridinyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted phenanthryl cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl, tert-butyl-substituted 9, 9-diphenylfluorenyl, tert-butyl-substituted 9,9' -spirobifluorenyl, trimethylsilyl-substituted phenyl, triethylsilyl-substituted phenyl, trimethylsilyl-substituted biphenyl, triphenylsilyl-substituted phenyl, adamantyl-substituted phenyl, adamantyl-substituted biphenyl, norbornyl-substituted phenyl, norbornyl-substituted biphenyl, deuteromethyl-substituted phenyl, deuteromethyl-substituted biphenyl, deuteroisopropyl-substituted phenyl, deuteroisopropyl-substituted biphenyl, deuteroitert-butyl-substituted phenyl, deuteroitert-butyl-substituted biphenyl, naphthyl-substituted phenyl, phenanthryl-substituted phenyl, triphenylene-substituted phenyl, benzofuransubstituted phenyl, benzothiophene-substituted phenyl, pyridine-substituted phenyl, pyrimidine-substituted phenyl Phenyl, quinoline-substituted phenyl, isoquinoline-substituted phenyl, quinazoline-substituted phenyl, quinoxaline-substituted phenyl, benzoxazole-substituted phenyl, benzothiazole-substituted phenyl, benzimidazole-substituted phenyl.
Preferably, said R 2 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutanyl, cyclopentylalkyl, cyclohexenyl, cycloheptanyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deutero-isopropyl, deutero-n-butyl, deutero-isobutyl, deutero-sec-butyl, deutero-adamantyl, deutero-norbornyl, deutero-phenyl, deutero-biphenyl, deutero-terphenyl, deutero-naphtalenyl, deutero-phenanthrenyl, deutero-triphenylenyl, deutero-pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, fluoro-substituted naphthyl, trifluoromethyl Phenyl substituted with a substituent, biphenyl substituted with a trifluoromethyl group, naphthyl substituted with a trifluoromethyl group, phenyl substituted with a cyano group, biphenyl substituted with a cyano group, naphthyl substituted with a cyano group, phenanthryl substituted with a cyano group, triphenylene substituted with a cyano group, 9-dimethylfluorenyl substituted with a cyano group, adamantyl substituted with a methyl group, norbornyl substituted with a methyl group, phenyl substituted with a methyl group, biphenyl substituted with a methyl group, naphthyl substituted with a methyl group, phenyl substituted with an ethyl group, biphenyl substituted with an ethyl group, naphthyl substituted with an ethyl group, phenyl substituted with an isopropyl group, biphenyl substituted with an isopropyl group, naphthyl substituted with an isopropyl group, adamantyl substituted with a tert-butyl group, phenyl substituted with a tert-butyl group, biphenyl substituted with a tert-butyl group, naphthyl substituted with a tert-butyl group, 9-dimethylfluorenyl substituted with a tert-butyl group tert-butyl substituted 9, 9-diphenylfluorenyl, tert-butyl substituted 9,9' -spirobifluorenyl, trimethylsilyl substituted phenyl, triethylsilyl substituted phenyl, trimethylsilyl substituted biphenyl, triphenylsilyl substituted phenyl, adamantyl substituted biphenyl, norbornyl substituted phenyl, norbornyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated isopropyl substituted phenyl, deuterated isopropyl substituted biphenyl, deuterated tert-butyl substituted phenyl, deuterated tert-butyl substituted biphenyl, naphthyl substituted phenyl, phenanthryl substituted phenyl, triphenylyl substituted phenyl, pyridine substituted phenyl, pyrimidine substituted phenyl.
Preferably, the formula III is independently selected from any one of the following groups:
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the R is 3 、R 4 Independently selected from hydrogen, deuterium, cyano, nitroAny one of a halogen atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group;
the Rd and Re are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or Ra, rb form a substituted or unsubstituted ring;
the Rf is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
Said b 1 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said b 2 Independently selected from 0, 1, 2, 3, 4 or 5, said b 3 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said b 4 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said b 5 Independently selected from 0, 1, 2, 3 or 4, said b 6 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said b 7 Independently selected from 0, 1, 2 or 3, said b 8 Independently selected from 0, 1 or 2.
Preferably, said R 3 、R 4 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atoms, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexenyl, cycloheptyl, adamantaneA group, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, and phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, and benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl, benzodibenzothiophenyl, benzooxazolyl, thiazolyl, and benzooxazolyl benzimidazolyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deuteroisopropyl, deutero-n-butyl, deuteroisobutyl, deutero-sec-butyl, deuterated tert-butyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylyl, deuterated pyridinyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, trifluoromethyl-substituted naphthyl, cyano-substituted phenyl, cyano-substituted biphenyl, cyano-substituted phenanthryl, cyano-substituted triphenylene, cyano-substituted 9, 9-dimethylfluorenyl, methyl-substituted adamantyl, methyl-substituted norbornyl, methyl-substituted phenyl, methyl-substituted biphenyl, methyl-substituted naphthyl, ethyl-substituted phenyl, ethyl-substituted biphenyl, ethyl-substituted naphthyl, isopropyl-substituted phenyl, isopropyl-substituted biphenyl, isopropyl-substituted naphthyl, tert-butyl-substituted adamantyl, tert-butyl-substituted phenyl, tert-butyl-substituted biphenyl, tert-butyl-substituted naphthyl, tert-butyl-substituted phenanthryl, tert-butyl-substituted 9, 9-dimethylfluorenyl Any one of a group, a tert-butyl-substituted 9, 9-diphenylfluorenyl group, a tert-butyl-substituted 9,9' -spirobifluorenyl group, a trimethylsilyl-substituted phenyl group, a triethylsilyl-substituted phenyl group, a triphenylsilyl-substituted phenyl group, a trimethylsilyl-substituted naphthyl group, an adamantyl-substituted phenyl group, an adamantyl-substituted biphenyl group, a norbornyl-substituted phenyl group, a norbornyl-substituted biphenyl group, a deuteromethyl-substituted phenyl group, a deuteromethyl-substituted biphenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated tert-butyl-substituted biphenyl group, a naphthyl-substituted phenyl group, a phenanthryl-substituted phenyl group, a triphenylyl-substituted phenyl group, a benzofuran-substituted phenyl group, a benzothiophene-substituted phenyl group, a pyridine-substituted phenyl group, a pyrimidine-substituted phenyl group, a quinoline-substituted phenyl group, a quinazoline-substituted phenyl group, a quinoxaline-substituted phenyl group, a benzoxazole-substituted phenyl group, a benzothiazole-substituted phenyl group, a benzimidazole-substituted phenyl group.
Preferably, rd, re are independently selected from hydrogen, deuterium, cyano, nitro, halogen atoms, or any of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropylalkyl, cyclobutylalkyl, cyclohexenyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, cyclopropenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothiophenyl, benzodibenzofuranyl, benzodibenzothiophenyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
The substituted groups in Rd and Re are selected from the group consisting of: any one of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, trifluoromethyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, naphthyl, phenanthryl, benzofuranyl, benzothienyl.
Preferably, said Rf is independently selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutene, benzocyclopentene, benzocyclohexene, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
The substituted group in Rf is selected from: any one of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, trifluoromethyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, naphthyl, phenanthryl, benzofuranyl, benzothienyl.
Preferably, the Ar 1 、Ar 2 One or two of which are selected from the group represented by formula III.
Preferably, the Ar 1 、Ar 2 At least one of which is selected from the group represented by formula III, and the remainder is selected from any one of the following structures:
the V is independently selected from C (R 5 ) Or an N atom; and up to 3V in each group are selected from N atoms;
the ring G is selected from unsubstituted or substituted by one or more R 6 A substituted C3-C7 aliphatic ring;
the Y is 2 Selected from O atom, S atom, C (R) g )(R h )、N(R i ) Any one of them;
the R is 5 、R 6 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R 6 Form a substituted or unsubstituted ring;
the R is g 、R h Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R is g 、R h Connection shape betweenForming a substituted or unsubstituted ring;
the R is i Independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the a 1 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 3 Independently selected from 0, 1, 2, 3 or 4.
Still preferably, the Ar 1 、Ar 2 At least one of which is selected from the group represented by formula III, and the remainder is selected from any one of the following structures:
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the R is 5 、R 6 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
The R is g 、R h 、R i Is defined herein;
the a 1 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 3 Independently selected from 0, 1, 2, 3 or 4, said a 4 Independently selected from 0, 1, 2, 3, 4 or 5, said a 5 Independently selected from 0, 1, 2, 3 or 4, said a 6 Independently selected from 0, 1, 2 or 3, said a 7 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 8 Independently selected from 0, 1 or 2, said a 9 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said a 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
Preferably, said R 5 、R 6 Independently selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropanyl, cyclobutanyl, cyclopentylalkyl, cyclohexenyl, cycloheptanyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, deuteromethyl, deuteroethyl, deutero-n-propyl, deutero-isopropyl, deutero-n-butyl, deutero-isobutyl, deutero-sec-butyl, deutero-adamantyl, deutero-norbornyl, deutero-phenyl, deutero-biphenyl, deutero-terphenyl, deutero-naphtalenyl, deutero-phenanthrenyl, deutero-triphenylenyl, deutero-pyridyl, deuterated pyrimidinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated benzofuranyl, deuterated benzothienyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated benzimidazolyl, fluoro-substituted phenyl, fluoro-substituted biphenyl A group, trifluoromethyl-substituted phenyl group, trifluoromethyl-substituted biphenyl group, trifluoromethyl-substituted naphthyl group, cyano-substituted phenyl group, cyano-substituted biphenyl group, cyano-substituted naphthyl group, cyano-substituted phenanthryl group, cyano-substituted triphenylene group, cyano-substituted 9, 9-dimethylfluorenyl group, methyl-substituted adamantyl group, methyl-substituted norbornyl group, methyl-substituted phenyl group, methyl-substituted biphenyl group, methyl-substituted naphthyl group, ethyl-substituted phenyl group, ethyl-substituted biphenyl group, ethyl-substituted naphthyl group, isopropyl-substituted phenyl group, isopropyl-substituted biphenyl group, isopropyl-substituted naphthyl group, tert-butyl-substituted adamantyl group, tert-butyl-substituted phenyl group, tert-butyl-substituted biphenyl group, tert-butyl-substituted naphthyl group, tert-butyl-substituted phenanthryl group, tert-butyl-substituted 9, 9-dimethylfluorenyl group tert-butyl substituted 9, 9-diphenylfluorenyl, tert-butyl substituted 9,9' -spirobifluorenyl, trimethylsilyl substituted phenyl, triethylsilyl substituted phenyl, triphenylsilyl substituted phenyl, trimethylsilyl substituted naphthyl, adamantyl substituted phenyl, adamantyl substituted biphenyl, norbornyl substituted phenyl, norbornyl substituted biphenyl, deuterated methyl substituted phenyl, deuterated methyl substituted biphenyl, deuterated isopropyl substituted phenyl, deuterated isopropyl substituted biphenyl, deuterated tert-butyl substituted phenyl, deuterated tert-butyl substituted biphenyl, naphthyl substituted phenyl, phenanthryl substituted phenyl, triphenylyl substituted phenyl, benzofuransubstituted phenyl, benzothiophene substituted phenyl, pyridine substituted phenyl, pyrimidine substituted phenyl, quinoline substituted phenyl, any one of isoquinoline substituted phenyl, quinazoline substituted phenyl, quinoxaline substituted phenyl, benzoxazole substituted phenyl, benzothiazole substituted phenyl, benzimidazole substituted phenyl.
The R is g 、R h Independently selected from hydrogen, deuterium, cyano, nitro, halogen atoms, or any of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, trimethylsilyl, triethylSilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, triphenylsilyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl, cycloheptylalkyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentylalkyl, benzocyclohexenyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyridyl, pyrimidinyl, and pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
The R is g 、R h The group substituted in (b) is selected from: any one of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, trifluoromethyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, naphthyl, phenanthryl, benzofuranyl, benzothienyl.
The Ri is independently selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutene, benzocyclopentene, benzocyclohexene, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, naphthyridinyl, phenanthroline, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9 '-spirobifluorenyl, benzo 9, 9-dimethylfluorenyl, benzo 9,9' -spirobifluorenyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzodibenzofuranyl, benzodibenzothienyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;
The substituted group in Ri is selected from: any one of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, trifluoromethyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, naphthyl, phenanthryl, benzofuranyl, benzothienyl.
Preferably, the L 0 、L 1 、L 2 Independently selected from a single bond or any one of the following groups:
the R is 7 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the c 1 Independently selected from 0, 1, 2, 3 or 4, said c 2 Independently selected from 0, 1, 2 or 3, said c 3 Independently selected from 0, 1 or 2, said c 4 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said c 5 Independently selected from 0, 1, 2, 3, 4 or 5, said c 6 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said c 7 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
Still preferably, the L 0 、L 1 、L 2 Independently selected from a single bond or any one of the following groups:
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most preferably, the fused ring compound is selected from any one of the following structures:
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the specific structural forms of the compounds of formula I according to the present invention are listed above, but the present invention is not limited to the listed chemical structures, and substituents are included in the groups defined above, whenever the structures shown in formula I are used as the basis.
Meanwhile, the invention also provides a preparation method of the compound shown in the formula I, and the specific synthetic route is shown as follows, but is not limited to the following:
when L 1 -Ar 1 And L is equal to 2 -Ar 2 When two are identical to each other: the above groups may be introduced together in one step, for example:
said X, Y, E, R 1 、L 0 、L 1 、L 2 、Ar 1 、Ar 2 、n 1 The definition of (a) is the same as that of the formula I, and Xa, xb and Xc are any one of Cl, br and I independently;
the main reaction type involved in the invention is Suzuki coupling reaction and Miyaura boric acid esterification reaction.
In addition, the invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises at least one or more than one condensed-cyclic compounds.
Preferably, the organic layer of the present invention is located between the anode and the cathode or outside at least one of the anode and the cathode. The organic layer may include a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport layer, an electron injection layer, a hole blocking layer, a light emitting layer, a capping layer, and the like. Specifically, the organic layer between the anode and the cathode may include a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and the like; the organic layer located outside at least one or more of the anode and the cathode may include a coating layer or the like.
Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises at least one or more than one of the condensed-cyclic compounds disclosed by the invention.
Preferably, the organic layer comprises at least one of an electron transport layer or a hole blocking layer, and at least one of the electron transport layer or the hole blocking layer comprises at least one or more of the condensed cyclic compounds according to the present invention.
Preferably, the organic layer comprises an electron transport layer, and the electron transport layer comprises at least one or more of the condensed cyclic compounds according to the present invention.
Preferably, the organic layer comprises a hole blocking layer, and the hole blocking layer comprises at least one or more of the condensed-cyclic compounds of the present invention.
As the anode of the present invention, a transmissive electrode, a reflective electrode or a semi-transmissive electrode may be selected, and when the anode is a transmissive electrode, the anode material may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) 2 ) Zinc oxide (ZnO) or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the anode material may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
As the hole injection layer of the present invention, a material having a good hole accepting ability is preferable. Specific examples include metalloporphyrins, oligothiophenes, arylamines, hexanitrile hexaazabenzophenanthrenes, quinacridones, perylenes, etc., and examples include 4,4',4 "-tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazabenzophenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5, 6-tetrafluoro-7, 7', 8' -tetracyandimethyl-p-benzoquinone (F4-TCNQ), poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (PEDOT/PSS), etc., but are not limited thereto.
As the hole transport layer of the present invention, a material having high hole mobility is preferable. Specific examples thereof include materials such as diphenylamines, fluorenes, carbazoles, biphenyldiamines, etc., and examples thereof include N, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), 4'4 "-tris (N, N-diphenylamino) triphenylamine (TDATA), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), 4',4" -tris (carbazol-9-yl) triphenylamine (TCTA), etc., but are not limited thereto.
As the light-emitting layer material of the present invention, a red, green or blue light-emitting material may be used, and generally comprises a guest (doped) material and a host material, and the guest material may be a simple fluorescent material or phosphorescent material, or may be a combination of fluorescent and phosphorescent materials. Examples of the host material of the light-emitting layer include, but are not limited to, distyrylaryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, pyrene derivatives, and the like, 9' -diphenyl-9H, 9' H-3,3' -bicarbazole, 9- (5- (3- (9H-carbazol-9-yl) phenyl) pyridin-3-yl) -9H-carbazole (CPPyC), 5, 7-diphenyl-5, 7-indolino [2,3-b ] carbazole, 4' -bis (carbazol-9-yl) -2,2' -dimethylbiphenyl (CDBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), and 2-tert-butyl-9, 10-bis (2-naphthyl) anthracene (TBADN), while the host material is required to have a bipolar charge transport property and an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material.
The guest material may be selected from any of the following structuresOne or more of the following: examples of the metal complex (for example, iridium complex, platinum complex, osmium complex, rhodium complex, etc.), anthracene derivative, pyrene derivative, perylene derivative, etc. include bis (2- (naphthalen-2-yl) pyridine) (acetylacetonate) iridium (Ir (npy) 2 acac), iridium acetylacetonato bis (2-phenylpyridine) (Ir (ppy) 2 (acac)) tris [2- (3-methyl-2-pyridinyl) phenyl ]]Iridium (Ir (3 mppy) 3 ) Bis (2-benzo [ H)]quinoline-C2, N') (acetylacetonato) iridium (Ir (bzq) 2 (acac)), bis (1-phenyl-isoquinoline) (acetylacetonate) iridium (Ir (piq) 2 (acac)), tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) 4,4' -bis (9-ethyl-3-carbazolyl vinyl) -1,1' -biphenyl (BCzVBi), 4' -bis [4- (di-p-tolylamino) styryl ]]Biphenyl (DPAVBi, etc., but is not limited thereto).
As the electron transport layer material of the present invention, a material having high electron mobility is preferable. Specific examples include quinolines, imidazoles, phenanthrenes, triazoles, metal chelates, azabenzene derivatives, anthracene derivatives, silicon-containing heterocycles, boron-containing heterocycles, cyano groups, benzimidazoles, and the like, and examples include 8-quinolinolato aluminum (Alq 3 ) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 2- (4-biphenyl) -5-Phenyloxadiazole (PBD), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), but is not limited thereto.
As the electron injection layer material of the present invention, a material having a low work function is preferable. Specific examples may include: metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, and the like. Examples can be cited as Li, ca, sr, liF, csF, caF 2 、BaO、Li 2 CO 3 、CaCO 3 、Li 2 C 2 O 4 、Cs 2 C 2 O 4 、CsAlF 4 LiOx, yb, tb, 8-hydroxyquinoline cesium, tris (8-hydroxyquinoline) aluminum, and the like, but is not limited thereto.
As the cathode of the present invention, a transmissive electrode, a semi-reflective electrode, or a reflective electrode may be selected. When the cathode is a transmissive electrode, the cathode material may be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the cathode material may be selected from Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Ca, liF/Al, mo, ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.
As the coating material of the present invention, a material having an optical coupling effect is preferable. Specific examples may include: examples of the metal halide, metal oxide, metal nitride, aromatic amine derivative, carbazole derivative, oxazole derivative and the like include LiF, csF, mgF2, caF2 and CsCl, cuI, V 2 O 5 、WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 、SiN、Alq 3 But is not limited thereto.
The organic layer of the organic electroluminescent device may be deposited by a vacuum deposition method, a spin coating method, a casting method, a langmuir-blodgeta (LB) method, etc., and the vacuum deposition conditions may be changed according to the compound when the vacuum deposition method is applied.
The organic electroluminescent device is mainly applied to the technical field of information display and the field of illumination, and is widely applied to various information displays in the aspect of information display, such as mobile phones, tablet computers, flat televisions, smart watches, VR, vehicle-mounted systems, digital cameras, wearable devices and the like.
The fabrication of the above-described organic electroluminescent device is specifically described in the following examples. However, the following examples are merely illustrative of the present specification, and the scope of the present specification is not limited to the examples.
Description of the starting materials, reagents and characterization equipment:
the source of the raw materials used in the following examples is not particularly limited and may be commercially available products or prepared by a preparation method well known to those skilled in the art.
The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;
the elemental analysis was carried out using a Vario EL cube organic elemental analyzer from Elementar, germany, and the sample mass was 5 to 10mg.
Synthesis example 1: preparation of intermediate A
Preparation of intermediate A-1:
a-1 (33.50 g,170.00 mmol), b-1 (32.27 g,175.00 mmol), sodium carbonate (27.03 g,255.00 mmol), 680mL toluene/ethanol/water (volume ratio of 2:1:1) mixed solvent were added into a reaction flask, after three times of air replacement with nitrogen, tetrakis (triphenylphosphine) palladium (1.96 g,1.70 mmol) was added into the reaction flask, and after the reaction was completed under nitrogen protection, the reaction mixture was cooled to room temperature, suction filtered, washed with distilled water, and then the obtained solid was recrystallized from toluene to obtain intermediate c-1 (37.10 g, yield 85%); the purity of the solid detected by HPLC is not less than 99.67%.
To the reaction flask were added c-1 (35.94 g,140.00 mmol), (methoxymethyl) triphenylphosphine chloride (71.99 g,210.00 mmol) and 700mL tetrahydrofuran, the mixture was stirred, then cooled to below 0℃potassium tert-butoxide (1M in THF, 350 mL) was slowly added dropwise to the mixture, after the dropwise addition was completed, the temperature of the mixture was slowly raised, and the mixture was stirred at room temperature for 6 hours. After the reaction is finished, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by reduced pressure distillation, cooling for crystallization, filtering, and recrystallizing the obtained solid with toluene/methanol (volume ratio of 8:1) to obtain an intermediate d-1 (32.29 g, 81%); the purity of the solid detected by HPLC is not less than 99.73 percent.
To a reaction flask were added d-1 (31.32 g,110.00 mmol), 185mL of Eton's reagent (methanesulfonic acid solution of phosphorus pentoxide having a composition of 7.7 wt%), 290mL of chlorobenzene, after the completion of the reflux reaction for 7 hours, the mixture was cooled to room temperature, distilled water was added to the mixture, followed by extraction with methylene chloride, and the organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure to concentrate the solvent, cooled and crystallized, suction-filtered, and then recrystallized with toluene to give intermediate e-1 (22.24 g, 80%), and the purity of the solid was ∈ 99.81% by HPLC detection.
E-1 (20.21 g,80.00 mmol), pinacol diboronate (21.58 g,85.00 mmol), potassium acetate (15.70 g,160.00 mmol) and DMF (425 mL) were added to the reaction flask, after three air substitutions with nitrogen, pd (dppf) Cl was added to the reaction flask 2 (0.62 g,0.85 mmol), heating and stirring for 7.5 hours, cooling to room temperature after the reaction, adding distilled water, extracting with dichloromethane, drying an organic layer with anhydrous magnesium sulfate, distilling and concentrating the solvent under reduced pressure, cooling and crystallizing, filtering, and recrystallizing with toluene to obtain an intermediate A-1 (23.13 g, 84%) with HPLC purity of more than or equal to 99.85%. Mass spectrum m/z:344.1571 (theory: 344.1584).
According to the preparation method, the invention also synthesizes the following intermediates:
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synthesis example 2: preparation of intermediate C-51
A-51 (20.65 g,60.00 mmol), g-51 (11.49 g,60.00 mmol), sodium carbonate (9.54 g,90.00 mmol), and 240mL toluene/ethanol/water (2:1:1) mixed solvent were added to the reaction flask, and after air was replaced with nitrogen three times, tetrakis (triphenylphosphine) palladium (0.69 g,0.60 mmol) was added to the reaction flask and reacted under reflux for 7 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=5: 1 to give intermediate B-51 (16.77 g, yield 85%); HPLC purity is more than or equal to 99.78%. Mass spectrum m/z:328.0670 (theory: 328.0655).
B-51 (14.80 g,45.00 mmol), pinacol diboronate (12.70 g,50.00 mmol), potassium acetate (8.83 g,90.00 mmol) and DMF (240 mL) were added to the reaction flask under nitrogen, after three nitrogen substitutions, pd (dppf) Cl was added to the flask 2 (0.37 g,0.50 mmol), heating and stirring for 7.5 hours, cooling to room temperature after the reaction, adding distilled water, extracting with dichloromethane, drying an organic layer with anhydrous magnesium sulfate, distilling and concentrating the solvent under reduced pressure, cooling and crystallizing, filtering, and recrystallizing with toluene to obtain an intermediate C-51 (15.70 g, 83%) with HPLC purity of more than or equal to 99.82%. Mass spectrum m/z:420.1882 (theory: 420.1897).
According to the preparation method, the invention also synthesizes the following intermediates:
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synthesis example 3: preparation of Compound 1
Synthesis of intermediate M-1:
under the protection of nitrogen, m-1 (10.93 g,40.00 mmol), n-1 (20.41 g,80.00 mmol) and CH are added into a reaction flask 3 COOK(10.30g,105.00mmol)、Pd(dppf)Cl 2 (0.18 g,0.24 mmol) and 340ml THF, under reflux for 8 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=10: 1 recrystallizationIntermediate M-1 (11.39 g, 77% yield) was obtained; the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:369.1125 (theory: 369.1112).
Synthesis of Compound 1:
m-1 (11.10 g,30.00 mmol), A-1 (10.33 g,30.00 mmol), na were added to the flask under nitrogen 2 CO 3 (4.77g，45.00mmol)、Pd(OAc) 2 (0.07g，0.30mmol)、P(t-Bu) 3 (0.17 g,0.60 mmol) and 120ml THF were reacted under reflux for 8.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was then added thereto, extraction was performed with ethyl acetate, and the organic layer was dried over anhydrous MgSO 4 Drying, removal of the solvent under reduced pressure, and recrystallization from toluene gave compound 1 (13.24 g, yield 80%); the HPLC purity is more than or equal to 99.93 percent. Mass spectrum m/z:551.2056 (theory: 551.2077). Theoretical element content (%) C 40 H 21 D 3 N 2 O is C,87.09; h,4.93; n,5.08. Measured element content (%) C,87.13; h,4.90; n,5.05.
Synthesis example 4: preparation of Compound 30
According to the same manner as that of Compound 1 of Synthesis example 3, m-1, n-1 and A-1 were replaced with m-30, n-30 and A-30 in equimolar amounts, respectively, to give Compound 30 (18.18 g), whose solid purity was not less than 99.92% as measured by HPLC. Mass spectrum m/z:776.2842 (theory: 776.2828). Theoretical element content (%) C 58 H 36 N 2 O is C,89.66; h,4.67; n,3.61. Measured element content (%) C,89.63; h,4.71; n,3.58.
Synthesis example 5: preparation of Compound 51
According to the same manner as that for Compound 1 of Synthesis example 3, m-1, n-1 and A-1 were replaced with equimolar amounts of m-30, n-51 and C-51, respectively, to give Compound 51 (17.87 g), which was examined by HPLC The purity of the measured solid is more than or equal to 99.88 percent. Mass spectrum m/z:778.2715 (theory: 778.2733). Theoretical element content (%) C 56 H 34 N 4 O is C,86.35; h,4.40; n,7.19. Measured element content (%) C,86.32; h,4.44; n,7.17.
Synthesis example 6: preparation of Compound 57
According to the same manner as that of Compound 1 in Synthesis example 3, m-1, n-1 and A-1 were replaced with equimolar amounts of m-30, n-57 and A-57, respectively, to give Compound 57 (15.23 g), whose solid purity was not less than 99.94% as measured by HPLC. Mass spectrum m/z:604.1768 (theory: 604.1787). Theoretical element content (%) C 42 H 24 N 2 O 3 C,83.43; h,4.00; n,4.63. Measured element content (%) C,83.40; h,4.05; n,4.66.
Synthesis example 7: preparation of Compound 70
According to the same manner as that of Compound 1 of Synthesis example 3, m-1, n-1 and A-1 were replaced with m-30, n-70 and A-70 in equimolar amounts, respectively, to give Compound 70 (15.92 g), and the purity of the solid was not less than 99.90% as measured by HPLC. Mass spectrum m/z:680.2117 (theory: 680.2100). Theoretical element content (%) C 48 H 28 N 2 O 3 C,84.69; h,4.15; n,4.12. Measured element content (%) C,84.72; h,4.10; n,4.15.
Synthesis example 8: preparation of Compound 79
Synthesis of intermediate M-79:
into a reaction flask were charged m-79 (25.38 g,80.00 mmol) and n-1 (20.41 g, 8) 0.00mmol)、CH 3 COOK(15.70g，160.00mmol)、Pd(dppf)Cl 2 (0.58 g,0.80 mmol) and 340ml THF, under reflux for 8 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=10: 1 recrystallisation to give intermediate M-79 (21.41 g, 84% yield); the HPLC purity is more than or equal to 99.87 percent. Mass spectrum m/z:316.9623 (theory: 316.9607).
Synthesis of intermediate N-79:
m-79 (19.12 g,60.00 mmol), n-57 (14.70 g,60.00 mmol), CH were added to the flask under nitrogen 3 COOK(11.77g,0120.00mmol)、Pd(dppf)Cl 2 (0.44 g,0.60 mmol) and 300ml THF were reacted under reflux for 8.5 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=10: 1 recrystallisation to give intermediate N-79 (18.19 g, 85% yield); the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:356.0701 (theory: 356.0716).
Synthesis of compound 79:
n-79 (10.70 g,30.00 mmol), A-79 (14.11 g,30.00 mmol), na were added to the flask under nitrogen 2 CO 3 (4.77g,45.00mmol)、Pd(OAc) 2 (0.07g,0.30mmol)、P(t-Bu) 3 (0.18 g of 0.60 mmol) and 100ml of THF were reacted under reflux for 9 hours. After the reaction was completed, the mixture was cooled to room temperature, water was then added thereto, the mixture was extracted with methylene chloride, and the organic layer was dried over anhydrous MgSO 4 Drying, removal of solvent under reduced pressure, and recrystallization from toluene gave compound 79 (16.35 g, yield 82%); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:664.2170 (theory: 664.2151). Theoretical element content (%) C 48 H 28 N 2 O 2 : c,86.73; h,4.25; n,4.21. Measured element content (%): c,86.77; h,4.20; n,4.24.
Synthesis example 9: preparation of Compound 81
According to the same manner as that for Compound 1 of Synthesis example 3, m-1, n-1, A-1 was replaced with equimolar m-30, n-81, A-57, respectively, to give compound 81 (17.72 g), purity of the solid was not less than 99.87% as determined by HPLC. Mass spectrum m/z:758.2331 (theory: 758.2318). Theoretical element content (%) C 52 H 30 N 4 O 3 C,82.31; h,3.99; n,7.38. Measured element content (%) C,82.28; h,3.95; n,7.39.
Synthesis example 10: preparation of Compound 93
According to the same manner as that of Compound 1 of Synthesis example 3, m-1, n-1 and A-1 were replaced with m-30, n-57 and C-93 in equimolar amounts, respectively, to give Compound 93 (16.74 g), which was found to have a solid purity of 99.90% or more by HPLC. Mass spectrum m/z:680.2115 (theory: 680.2100). Theoretical element content (%) C 48 H 28 N 2 O 3 C,84.69; h,4.15; n,4.12. Measured element content (%) C,84.65; h,4.13; n,4.16.
Synthesis example 11: preparation of Compound 115
According to the same manner as that of Compound 1 in Synthesis example 3, m-1, n-1 and A-1 were replaced with m-30, n-115 and A-115 in equimolar amounts, respectively, to give Compound 115 (15.88 g), and the purity of the solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z:637.1266 (theory: 637.1283). Theoretical element content (%) C 41 H 23 N 3 OS 2 C,77.21; h,3.64; n,6.59. Measured element content (%) C,77.18; h,3.66; n,6.62.
Synthesis example 12: preparation of Compound 153
Compound 1 is identical according to Synthesis example 3M-1, n-1 and A-1 are replaced by m-30, n-153 and A-153 with the same mole respectively to obtain a compound 153 (19.12 g), and the purity of the solid detected by HPLC is more than or equal to 99.86%. Mass spectrum m/z:796.2469 (theory: 796.2458). Theoretical element content (%) C 54 H 24 D 8 N 2 OS 2 C,81.38; h,5.06; n,3.51. The measured element content (%) is C,81.35; h,5.02; n,3.47.
Synthesis example 13: preparation of Compound 166
According to the same manner as that of Compound 1 of Synthesis example 3, m-1, n-1 and A-1 were replaced with m-166, n-166 and A-166 in equimolar amounts, respectively, to give Compound 166 (13.52 g), whose solid purity was not less than 99.95% as measured by HPLC. Mass spectrum m/z:570.1960 (theory: 570.1943). Theoretical element content (%) C 39 H 26 N 2 O 3 : c,82.09; h,4.59; n,4.91. Measured element content (%): c,82.12; h,4.54; n,4.95.
Synthesis example 14: preparation of Compound 168
According to the same manner as that of Compound 1 in Synthesis example 3, m-1, n-1 and A-1 were replaced with m-30, n-168 and A-57 in equimolar amounts, respectively, to give Compound 168 (18.57 g), whose solid purity was not less than 99.90% as measured by HPLC. Mass spectrum m/z:754.2521 (theory: 754.2508). Theoretical element content (%) C 56 H 34 O 3 : c,89.10; h,4.54. Measured element content (%): c,89.06; h,4.58.
Synthesis example 15: preparation of Compound 196
According to the combination ofThe same preparation method of the compound 1 of example 3, m-1, n-1 and A-1 are respectively replaced by m-30, n-196 and C-196 with equimolar amounts, so as to obtain a compound 196 (18.22 g), wherein the purity of the solid detected by HPLC is more than or equal to 99.93%. Mass spectrum m/z:731.3170 (theory: 731.3188). Theoretical element content (%) C 55 H 41 NO: c,90.25; h,5.65; n,1.91. Measured element content (%): c,90.21; h,5.68; n,1.88.
Synthesis example 16: preparation of Compound 254
According to the same manner as that of Compound 1 of Synthesis example 3, m-1, n-1 and A-1 were replaced with m-30, n-254 and C-254 in equimolar amounts, respectively, to give Compound 254 (18.22 g), and the purity of the solid was not less than 99.89% as measured by HPLC. Mass spectrum m/z:904.3435 (theory: 904.3454). Theoretical element content (%) C 68 H 44 N 2 O: c,90.24; h,4.90; n,3.10. Measured element content (%): c,90.26; h,4.87; n,3.14.
Synthesis example 17: preparation of Compound 261
According to the same manner as that of Compound 1 in Synthesis example 3, m-1, n-1 and A-1 were replaced with m-30, n-261 and C-261, respectively, to give Compound 261 (19.35 g), and the purity of the solid was not less than 99.85% as measured by HPLC. Mass spectrum m/z:826.2357 (theory: 826.2364). Theoretical element content (%) C 59 H 38 OS 2 : c,85.68; h,4.63. Measured element content (%): c,85.64; h,4.66.
Synthesis example 18: preparation of Compound 287
According to synthesis example 3The same preparation method of the compound 1 comprises the step of replacing m-1, n-1 and A-1 with m-30, n-287 and A-287 which are equimolar respectively to obtain a compound 287 (15.71 g), wherein the purity of the solid detected by HPLC is more than or equal to 99.91%. Mass spectrum m/z:642.1889 (theory: 642.1878). Theoretical element content (%) C 44 H 26 N 4 S: c,82.22; h,4.08; n,8.72. Measured element content (%): c,82.20; h,4.12; n,8.76.
Synthesis example 19: preparation of Compound 317
According to the same manner as that of Compound 1 in Synthesis example 3, m-1, n-1 and A-1 were replaced with equimolar amounts of m-30, n-115 and A-287, respectively, to give Compound 317 (16.45 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:652.1116 (theory: 652.1102). Theoretical element content (%) C 42 H 24 N 2 S 3 : c,77.27; h,3.71; n,4.29. Measured element content (%): c,77.25; h,3.67; n,4.26.
Synthesis example 20: preparation of Compound 333
According to the same manner as that of Compound 1 of Synthesis example 3, m-1, n-1 and A-1 were replaced with equimolar amounts of m-30, n-333 and A-333, respectively, to give Compound 333 (17.11 g), whose solid purity was not less than 99.94% as measured by HPLC. Mass spectrum m/z:802.1835 (theory: 802.1823). Theoretical element content (%) C 56 H 34 S 3 : c,83.76; h,4.27. Measured element content (%): c,83.80; h,4.22.
Synthesis example 21: preparation of Compound 363
According to the synthesis implementationExample 3 the same preparation as that of compound 1 was carried out, m-1, n-1 and A-1 were replaced with m-363, n-363 and C-363 in equimolar amounts, respectively, to give compound 363 (18.23 g), and the purity of the solid was not less than 99.92% as measured by HPLC. Mass spectrum m/z:778.2352 (theory: 778.2341). Theoretical element content (%) C 52 H 26 D 4 N 4 O 2 S: c,80.18; h,4.40; n,7.19. Measured element content (%): c,80.22; h,4.45; n,7.16.
Synthesis example 22: preparation of Compound 445
According to the same manner as that of Compound 1 in Synthesis example 3, m-1, n-1 and A-1 were replaced with m-445, n-445 and A-445, respectively, to give Compound 445 (16.17 g), whose solid purity was not less than 99.92% as measured by HPLC. Mass spectrum m/z:673.1545 (theory: 673.1534). Theoretical element content (%) C 46 H 27 NOS 2 : c,81.99; h,4.04; n,2.08. Measured element content (%): c,81.94; h,4.07; n,2.05.
Synthesis example 23: preparation of Compound 434
According to the same manner as that of Compound 1 in Synthesis example 3, m-1, n-1 and A-1 were replaced with m-472, n-472 and A-472 in equimolar amounts, respectively, to give Compound 472 (16.14 g), and the purity of the solid was not less than 99.90% as measured by HPLC. Mass spectrum m/z:672.2365 (theory: 672.2348). Theoretical element content (%) C 46 H 32 N 4 S: c,82.11; h,4.79; n,8.33. Measured element content (%): c,82.14; h,4.75; n,8.30.
Synthesis example 24: preparation of Compound 482
Synthesis of intermediate M-482:
under the protection of nitrogen, m-482 (14.75 g,80.00 mmol), n-57 (19.61 g,80.00 mmol) and CH are added into a reaction flask 3 COOK(15.70g，160.00mmol)、Pd(dppf)Cl 2 (0.58 g,0.80 mmol) and 340ml THF, under reflux for 8 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=5: 1 to give intermediate M-482 (17.95 g, yield 84%); HPLC purity is more than or equal to 99.83%. Mass spectrum m/z:265.9745 (theory: 265.9762).
Synthesis of intermediate N-482:
m-482 (16.02 g,60.00 mmol), o-482 (19.21 g,60.00 mmol), CH were added to the flask under nitrogen 3 COOK(11.77g,120.00mmol)、Pd(dppf)Cl 2 (0.44 g,0.60 mmol) and 300ml THF were reacted under reflux for 8.5 hours. After the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was purified with toluene/ethanol=5: 1 to obtain intermediate N-482 (22.49 g, yield 85%); the HPLC purity is more than or equal to 99.89 percent. Mass spectrum m/z:440.1419 (theory: 440.1404).
Synthesis of compound 482:
n-482 (13.23 g,30.00 mmol), A-57 (12.61 g,30.00 mmol), na were added to the flask under nitrogen 2 CO 3 (4.77g,45.00mmol)、Pd(OAc) 2 (0.07g,0.30mmol)、P(t-Bu) 3 (0.18 g of 0.60 mmol) and 100ml of THF were reacted under reflux for 9 hours. After the reaction was completed, the mixture was cooled to room temperature, water was then added thereto, the mixture was extracted with methylene chloride, and the organic layer was dried over anhydrous MgSO 4 Drying, removal of solvent under reduced pressure, and recrystallization from toluene gave compound 482 (16.80 g, yield 82%); HPLC purity is more than or equal to 99.95%. Mass spectrum m/z:682.2385 (theory: 682.2369). Theoretical element content (%) C 47 H 30 N 4 O 2 : c,82.68; h,4.43; n,8.21. Measured element content (%): c,82.65; h,4.47; n,8.17.
Synthesis example 25: preparation of Compound 490
According to the same manner as that for compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-490, o-490 and A-30, respectively, to give compound 490 (17.61 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:698.2664 (theory: 698.2682). Theoretical element content (%) C 48 H 34 N 4 O 2 : c,82.50; h,4.90; n,8.02. Measured element content (%): c,82.45; h,4.92; n,8.06.
Synthesis example 26: preparation of Compound 493
According to the same manner as that described in Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-493, o-493 and A-30, respectively, to give Compound 493 (17.80 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z:714.2466 (theory: 714.2451). Theoretical element content (%) C 47 H 34 N 4 O 2 Si: c,78.96; h,4.79; n,7.84. Measured element content (%): c,78.92; h,4.83; n,7.80.
Synthesis example 27: preparation of Compound 497
According to the same manner as that described for compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-497, o-497 and A-57, respectively, to give compound 497 (17.99 g), and the purity of the solid was not less than 99.91% as measured by HPLC. Mass spectrum m/z:749.1865 (theory: 749.1885). Theoretical element content (%) C 49 H 27 N 5 O 2 S: c,78.49; h,3.63; n,9.34. Measured element content (%): c,78.52; h,3.60; n,9.37.
Synthesis example 28: preparation of Compound 505
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-115, o-505 and A-505, respectively, to give compound 505 (17.43 g), and the purity of the solid was not less than 99.93% as measured by HPLC. Mass spectrum m/z:708.1999 (theory: 708.1984). Theoretical element content (%) C 48 H 28 N 4 OS: c,81.33; h,3.98; n,7.90. Measured element content (%): c,81.37; h,3.95; n,7.87.
Synthesis example 29: preparation of Compound 508
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-115, o-508 and A-93, respectively, to give compound 508 (13.11 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:546.1530 (theory: 546.1514). Theoretical element content (%) C 35 H 22 N 4 OS: c,76.90; h,4.06; n,10.25. Measured element content (%): c,76.93; h,4.01; n,10.28.
Synthesis example 30: preparation of Compound 515
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-115, n-115 and C-515, respectively, to give compound 515 (17.60 g), and the purity of the solid was not less than 99.95% as measured by HPLC. Mass spectrum m/z:715.1493 (theory: 715.1501). Theoretical element content (%) C 45 H 25 N 5 OS 2 : c,75.50; h,3.52; n,9.78. Measured element content (%): c,75.55; h,3.53; n,9.76.
Synthesis example 31: preparation of Compound 526
According to the same manner as that for compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-526, o-526 and A-57, respectively, to give compound 526 (19.16 g), which was found to have a solid purity of not less than 99.91% by HPLC. Mass spectrum m/z:798.1500 (theory: 798.1513). Theoretical element content (%) C 48 H 23 F 5 N 4 OS: c,72.18; h,2.90; n,7.01. Measured element content (%): c,72.15; h,2.88; n,7.03.
Synthesis example 32: preparation of Compound 555
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 are replaced with equimolar amounts of n-555, o-555 and A-1, respectively, to give compound 555 (17.72 g), and the purity of the solid as measured by HPLC is not less than 99.90%. Mass spectrum m/z:747.2325 (theory: 747.2342). Theoretical element content (%) C 51 H 33 N 3 O 2 Si: c,81.90; h,4.45; n,5.62. Measured element content (%): c,81.93; h,4.41; n,5.66.
Synthesis example 33: preparation of Compound 558
According to the same manner as that for preparing compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-558, o-558 and A-93, respectively, to give compound 558 (16.32 g, solid purity of 99.93% or more as measured by HPLC: mass spectrum m/z:655.1877 (theoretical value: 655.1896): theoretical element content (%) C) 45 H 25 N 3 O 3 : c,82.43; h,3.84; n,6.41. Measured element content (%): c,82.46; h,3.81;N,6.45。
synthesis example 34: preparation of Compound 569
According to the same manner as that for compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-569, n-569 and A-57, respectively, to give compound 569 (18.42 g), and the purity of the solid was not less than 99.96% as measured by HPLC. Mass spectrum m/z:757.2351 (theory: 757.2365). Theoretical element content (%) C 53 H 31 N 3 O 3 : c,84.00; h,4.12; n,5.54. Measured element content (%): c,84.05; h,4.08; n,5.58.
Synthesis example 35: preparation of Compound 581
According to the same manner as that for compound 482 of Synthesis example 24, n-57, o-482 and A-57 are replaced with equimolar amounts of n-261, o-581 and A-30, respectively, to give compound 581 (15.90 g), and the purity of the solid as measured by HPLC is not less than 99.96%. Mass spectrum m/z:638.2175 (theory: 638.2158). Theoretical element content (%) C 43 H 18 D 7 N 3 OS: c,80.85; h,5.05; n,6.58. Measured element content (%): c,80.82; h,5.09; n,6.55.
Synthesis example 36: preparation of Compound 583
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 are replaced with equimolar amounts of n-261, o-583 and A-30, respectively, to give compound 583 (18.27 g), and the purity of the solid as measured by HPLC is not less than 99.95%. Mass spectrum m/z:733.2170 (theory: 733.2188). Theoretical element content (%) C 51 H 31 N 3 OS：C,83.47；H,4.26; n,5.73. Measured element content (%): c,83.42; h,4.29; n,5.70.
Synthesis example 37: preparation of Compound 588
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-261, o-588 and A-30, respectively, to give compound 588 (16.75 g), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:671.1683 (theory: 671.1667). Theoretical element content (%) C 45 H 25 N 3 O 2 S: c,80.46; h,3.75; n,6.26. Measured element content (%): c,80.42; h,3.70; n,6.29.
Synthesis example 38: preparation of Compound 598
According to the same manner as that for compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-598, o-569 and A-57, respectively, to give compound 598 (21.50 g), and the purity of the solid was not less than 99.90% as measured by HPLC. Mass spectrum m/z:895.2640 (theory: 895.2657). Theoretical element content (%) C 64 H 37 N 3 OS: c,85.79; h,4.16; n,4.69. Measured element content (%): c,85.75; h,4.14; n,4.71.
Synthesis example 39: preparation of Compound 641
According to the same manner as that for compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-641, o-641 and A-641, respectively, to give compound 641 (19.77 g), and the purity of the solid was not less than 99.88% as measured by HPLC. Mass spectrum m/z:844.3247 (theory: 844.3236). Theoretical element content (%) C 58 H 44 N 4 OS: c,82.43; h,5.25; n,6.63. Measured element content (%): c,82.46; h,5.24; n,6.67.
Synthesis example 40: preparation of Compound 658
According to the same manner as that for compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-115, o-658 and A-658, respectively, to give compound 658 (17.00 g), which was found to have a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:674.1608 (theory: 674.1599). Theoretical element content (%) C 44 H 26 N 4 S 2 : c,78.31; h,3.88; n,8.30. Measured element content (%): c,78.35; h,3.85; n,8.27.
Synthesis example 41: preparation of Compound 662
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-662, o-662 and A-662, respectively, to give compound 662 (20.14 g), and the purity of the solid was not less than 99.87% as measured by HPLC. Mass spectrum m/z:849.2009 (theory: 849.2021). Theoretical element content (%) C 57 H 31 N 5 S 2 : c,80.54; h,3.68; n,8.24. Measured element content (%): c,80.50; h,3.69; n,8.28.
Synthesis example 42: preparation of Compound 665
According to the same manner as that described in Synthesis example 24, compound 482 was synthesized by substituting n-57, o-482 and A-57 with equimolar amounts of n-665, o-665 and A-287, respectively, to give Compound 665 (16.42 g), which was found to have a solid purity of 99.92% or more by HPLC. Mass spectrometrym/z:675.1564 (theory: 675.1551). Theoretical element content (%) C 43 H 25 N 5 S 2 : c,76.42; h,3.73; n,10.36. Measured element content (%): c,76.45; h,3.77; n,10.31.
Synthesis example 43: preparation of Compound 667
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-667, o-667 and A-667, respectively, to give compound 667 (14.12 g), and the purity of the solid was not less than 99.91% as measured by HPLC. Mass spectrum m/z:603.1618 (theory: 603.1600). Theoretical element content (%) C 38 H 17 D 5 N 4 S 2 : c,75.59; h,4.51; n,9.28. Measured element content (%): c,75.62; h,4.48; n,9.25.
Synthesis example 44: preparation of Compound 678
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 are replaced with equimolar amounts of n-678, o-678 and A-678, respectively, to give compound 678 (14.13 g), and the purity of the solid as measured by HPLC is not less than 99.92%. Mass spectrum m/z:581.1547 (theory: 581.1562). Theoretical element content (%) C 39 H 23 N 3 OS: c,80.53; h,3.99; n,7.22. Measured element content (%): c,80.55; h,3.96; n,7.17.
Synthesis example 45: preparation of Compound 679
According to the same manner as that for preparing compound 482 of Synthesis example 24, n-57, o-482 and A-57 are replaced with equimolar amounts of n-678, o-679, respectively,A-679 gave compound 679 (15.74 g) having a solid purity of 99.92% or more as measured by HPLC. Mass spectrum m/z:639.2360 (theory: 639.2344). Theoretical element content (%) C 43 H 33 N 3 OS: c,80.72; h,5.20; n,6.57. Measured element content (%): c,80.74; h,5.25; n,6.53.
Synthesis example 46: preparation of Compound 688
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-678, n-678 and A-688, respectively, to give compound 688 (17.27 g), and the purity of the solid was not less than 99.95% by HPLC. Mass spectrum m/z:697.1807 (theory: 697.1824). Theoretical element content (%) C 47 H 27 N 3 O 2 S: c,80.90; h,3.90; n,6.02. Measured element content (%): c,80.87; h,3.92; n,6.06.
Synthesis example 47: preparation of Compound 713
According to the same manner as that of compound 482 of Synthesis example 24, n-57, o-482 and A-57 were replaced with equimolar amounts of n-598, o-598 and C-713, respectively, to give compound 713 (18.21 g), whose solid purity was not less than 99.90% as measured by HPLC. Mass spectrum m/z:734.2522 (theory: 734.2504). Theoretical element content (%) C 51 H 34 N 4 S: c,83.35; h,4.66; n,7.62. Measured element content (%): c,83.30; h,4.65; n,7.58.
Device embodiment
Device embodiment test method, conditions and apparatus description:
the driving voltage and luminous efficiency were tested by an I-V-L test system consisting of a combination of test software, a computer, a K2400 digital source meter manufactured by Keithley company, usa, and a PR788 spectroscanning luminance meter manufactured by Photo Research, usa.
OLED lifetime was tested by the McScience company M6000 OLED lifetime test system. The test environment is an atmospheric environment, and the temperature is room temperature.
Device example 1: preparation of red light organic electroluminescent device
Firstly, placing an ITO (10 nm)/Ag (100 nm)/ITO (10 nm) glass substrate in distilled water for cleaning for 2 times, washing by ultrasonic waves for 30 minutes, repeatedly cleaning by using distilled water for 2 times, washing by ultrasonic waves for 10 minutes, washing by using isopropanol, acetone and methanol solvents in sequence after the distilled water is cleaned, drying on a hot plate heated to 120 ℃, transferring the dried substrate into a plasma cleaner, washing for 5 minutes, and transferring the substrate into an evaporator.
Then, HI-1 and HT-1 with a film thickness of 10nm are evaporated on the glass substrate as hole injection layers, wherein the mass ratio of HI-1 to HT-1 is 3:97, HT-1 with a film thickness of 120nm is evaporated on the hole injection layers as hole transport layers, EB-1 with a film thickness of 60nm is evaporated on the hole transport layers as electron blocking layers, a light emitting layer with a film thickness of 40nm is evaporated on the electron blocking layers in vacuum, the light emitting layer structure comprises a compound 1 synthesized in synthetic example 1 as a first host material, RH-2 as a second host material, RD-1 is used as a doping material, the mass ratio of the compound 1, RH-2 and RD-1 is 49:2, then ET-1 and Liq with a film thickness of 35nm are evaporated on the light emitting layers as electron transport layers, liF with a film thickness of 1nm is evaporated on the electron transport layers, then Mg with a film thickness of 15nm is evaporated on the electron injection layers, the alloy with a film thickness of Ag (Ag and Mg 1: 9:70 nm) is evaporated on the electron injection layers, and then the organic electroluminescent device is prepared as a cathode layer.
Device example 2 to device example 35:
a green organic electroluminescent device was produced by the same production method as in device example 1, except that the compound 1 in device example 1 was replaced with the compound 30, the compound 51, the compound 57, the compound 79, the compound 81, the compound 93, the compound 115, the compound 166, the compound 168, the compound 196, the compound 254, the compound 261, the compound 317, the compound 333, the compound 472, the compound 482, the compound 490, the compound 493, the compound 497, the compound 505, the compound 515, the compound 555, the compound 569, the compound 581, the compound 583, the compound 588, the compound 598, the compound 641, the compound 665, the compound 667, the compound 678, the compound 679, the compound 688 and the compound 713, respectively, of the present invention.
Comparative examples 1-2:
an organic electroluminescent device was manufactured by the same manufacturing method as device example 1, except that the compound 1 in device example 1 was replaced with the comparative compound 1, comparative compound 2 as the first host material. The results of the light emission characteristics test of the above organic electroluminescent devices are shown in table 1 below.
Table 1: light emitting characteristic test of organic electroluminescent device
According to the test results in table 1 of the invention, the compound provided by the invention has proper HOMO and LUMO energy levels, can be matched with the energy levels of adjacent functional layers, and reduces the injection barrier of holes and electrons, so that the driving voltage is reduced, and meanwhile, when the compound is used as a main body material, the compound has good charge transmission balancing capability, the luminous efficiency of an organic electroluminescent device is effectively improved, and the service life of the device is prolonged.
Device example 36: preparation of green light organic electroluminescent device
After washing and drying an ITO (10 nm)/Ag (100 nm)/ITO (10 nm) glass substrate, transferring the glass substrate to an evaporator, evaporating HI-1 and HT-1 with film thickness of 10nm on the glass substrate as hole injection layers, wherein the mass ratio of HI-1 to HT-1 is 3:97, evaporating HT-1 with film thickness of 120nm on the hole injection layers as hole transport layers, evaporating EB-2 with film thickness of 40nm on the hole transport layers as electron blocking layers, evaporating a light-emitting layer with film thickness of 35nm on the electron blocking layers in a vacuum way, wherein the light-emitting layer structure comprises GH-1 as a first main body material, GH-2 as a second main body material, GD-1 as a doping material, the mass ratio of GH-1, GH-2 to GD-1 is 47:6, then evaporating compound 1 and Liq prepared in embodiment 2 of the device with film thickness of 35nm on the light-emitting layers as electron transport layers, evaporating EB-2 with film thickness of 40nm on the electron transport layers, evaporating Ag-1 to Mg-1 as an electron injection layer, and then evaporating an electroluminescent alloy film thickness of 35nm on the cathode layer as Mg-9:70, and then evaporating an electroluminescent device as a cathode layer.
Device examples 37 to 65:
a green organic electroluminescent device was produced by the same production method as in device example 36, except that compound 1 in device example 36 was replaced with compound 30, compound 57, compound 70, compound 81, compound 93, compound 153, compound 166, compound 196, compound 287, compound 317, compound 333, compound 363, compound 445, compound 482, compound 493, compound 497, compound 505, compound 508, compound 515, compound 526, compound 555, compound 558, compound 581, compound 588, compound 658, compound 662, compound 665, compound 688 and compound 713, respectively, according to the present invention.
Comparative examples 3 to 4:
an organic electroluminescent device was manufactured by the same manufacturing method as device example 36, except that the compound 1 in device example 36 was replaced with the comparative compound 3 and the comparative compound 4 as electron transporting materials. The results of the light emission characteristics test of the above organic electroluminescent devices are shown in table 2 below.
Table 2: light emitting characteristic test of organic electroluminescent device
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According to the test results in Table 2, the compound provided by the invention has good electron transmission performance, can balance hole and electron transmission, and avoids exciton recombination at the edge of a light-emitting layer, thereby reducing the driving voltage of an organic electroluminescent device, improving the light-emitting efficiency and prolonging the service life of the device.
Device example 66: preparation of green light organic electroluminescent device
After washing and drying an ITO (10 nm)/Ag (100 nm)/ITO (10 nm) glass substrate, transferring the glass substrate to an evaporator, evaporating HI-1 and HT-1 with film thickness of 10nm on the glass substrate as hole injection layers, wherein the mass ratio of HI-1 to HT-1 is 3:97, evaporating HT-1 with film thickness of 120nm on the hole injection layers as hole transport layers, evaporating EB-2 with film thickness of 40nm on the hole transport layers as electron blocking layers, evaporating a light-emitting layer with film thickness of 35nm on the electron blocking layers in a vacuum manner, wherein the light-emitting layer structure comprises GH-1 as a first main material, GH-2 as a second main material, GD-1 as a doping material, the mass ratio of GH-1, GH-2 to HT-1 is 47:6, the compound 57 prepared in the invention with film thickness of 40nm on the light-emitting layers is used as hole blocking layers, then evaporating ET-1 and Liq with film thickness of 35nm on the hole blocking layers as electron transport layers, the mass ratio of ET-1 to Liq is used as an electroluminescent alloy layer with film thickness of 35nm on the electron injection layer with film thickness of Mg of 1:9, and then evaporating an electroluminescent device with film thickness of 1 to Mg on the cathode layer with film thickness of 1:9, and then evaporating an electroluminescent device with film thickness of 1 as a cathode layer with film thickness of Mg is prepared.
Device example 66-device example 85:
a green organic electroluminescent device was produced by the same production method as in device example 66, except that compound 57 in device example 66 was replaced with compound 79, compound 93, compound 166, compound 287, compound 317, compound 333, compound 482, compound 493, compound 497, compound 505, compound 515, compound 555, compound 581, compound 583, compound 588, compound 665, compound 678, compound 679 and compound 688, respectively, as a hole blocking material.
Comparative examples 5 to 6:
an organic electroluminescent device was manufactured by the same manufacturing method as device example 66, except that the compound 57 in device example 66 was replaced with the comparative compound 3 and the comparative compound 4 as a hole blocking material. The results of the light emission characteristics test of the above organic electroluminescent devices are shown in table 3 below.
Table 3: light emitting characteristic test of organic electroluminescent device
According to the test results in Table 3, the compound provided by the invention has a higher triplet state energy level, can block holes from migrating to one side of an electron transport layer, can effectively improve the recombination rate of excitons in a light-emitting layer, can improve the light-emitting efficiency of an organic electroluminescent device, can avoid the occurrence of leakage current phenomenon, and can prolong the service life of the device.
It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.
Claims (10)
1. A fused ring compound, wherein the fused ring compound is selected from the group consisting of structures represented by formula I:
in the formula I, Y is selected from any one of O atom, S atom, C (Ra) (Rb) and N (Rc);
the ring E is selected from any one of the groups represented by the formulas II-1 to II-7:
in formulas II-1 to II-7, any two adjacent "×" represent bonding sites;
the R is 1 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or said R 1 Can be combined with L 0 Direct bonding;
said n 1 Selected from 0, 1 or 2;
q is independently selected from CH or N atoms, and L 0 Q at the junction is selected from a C atom, and at most two Q in each of the structures of formulas II-1 to II-7 are selected from an N atom;
The R is 2 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
said n 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said n 3 Selected from 0, 1, 2, 3, 4, 5 or 6, said n 4 Selected from 0, 1, 2, 3 or 4; having two or more R' s 2 When present, two or more R' s 2 Identical or different from each other, or adjacent two R' s 2 Form a substituted or unsubstituted ring;
the Ra and Rb are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or Ra, rb form a substituted or unsubstituted ring;
the Rc is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
The X is independently selected from C (R 0 ) Or an N atom; and up to three X are selected from N atoms, and L 0 、L 1 、L 2 X at the junction is selected from C atoms;
the R is 0 Independently selected from hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroarylAny one of them; or adjacent R 0 Form a substituted or unsubstituted ring;
the Ar is as follows 1 、Ar 2 At least one of the groups represented by formula III, and the rest is any one selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
in formula III, the Z 1 Independently selected from C (R) 3 ) Or N atom, with L 1 、L 2 Z at the junction 1 Selected from the group consisting of C atoms;
the ring M is selected from a group represented by a formula III-1 or a formula III-2, and two adjacent ". Times. -bonds represent condensed sites;
the Z is 2 Independently selected from C (R) 3 ) Or an N atom, and one or two Z's in formula III-1 2 Selected from N atoms, and L 1 、L 2 Z at the junction 2 Selected from the group consisting of C atoms;
the Z is 3 Independently selected from C (R) 4 ) Or N atom, with L 1 、L 2 Z at the junction 3 Selected from the group consisting of C atoms; the Y is 1 Independently selected from any one of O atom, S atom, C (RdRe) and N (Rf);
the R is 3 、R 4 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R 3 Form a substituted or unsubstituted ring;
the Rd and Re are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or Ra, rb form a substituted or unsubstituted ring;
the Rf is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
The L is 0 、L 1 、L 2 Independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted heteroarylene.
2. The fused ring compound according to claim 1, wherein the fused ring compound is selected from any one of structures represented by the following formulas IV-1 to IV-6:
the Y, ring E, R 1 、R 0 、L 0 、L 1 、L 2 、Ar 1 、Ar 2 、n 1 Is as defined in formula I;
the m is 1 Independently selected from 0, 1, 2 or 3, said m 2 Independently selected from 0, 1 or 2.
3. The fused ring compound of claim 1, wherein the fused ring compound isSelected from any one of the following groups:
said Y, R 1 、R 2 、n 1 、n 2 、n 3 、n 4 Is as defined in formula I;
said n 1 Independently selected from 0, 1 or 2, said n 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said n 3 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said n 4 Independently selected from 0, 1, 2, 3 or 4, said n 5 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said n 6 Independently selected from 0, 1, 2, 3, 4 or 5, said n 7 Independently selected from 0, 1, 2 or 3.
4. The fused ring compound according to claim 1, wherein formula III is independently selected from any one of the following groups:
The R is 3 、R 4 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
the Rd and Re are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or Ra, rb form a substituted or unsubstituted ring;
the Rf is independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
said b 1 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said b 2 Independently selected from 0, 1, 2, 3, 4 or 5, said b 3 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said b 4 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said b 5 Independently selected from 0, 1, 2, 3 or 4, said b 6 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said b 7 Independently selected from 0, 1, 2 or 3, said b 8 Independently selected from 0, 1 or 2.
5. The fused ring compound according to claim 1, wherein Ar 1 、Ar 2 At least one of which is selected from the group represented by formula III, and the remainder is selected from any one of the following structures:
the V is independently selected from C (R 5 ) Or an N atom; and up to 3V in each group are selected from N atoms;
the ring G is selected from unsubstituted or substituted by one or more R 6 A substituted C3-C7 aliphatic ring;
the Y is 2 Selected from O atom, S atom, C (R) g )(R h )、N(R i ) Any one of them;
the R is 5 、R 6 Independent and independentIs selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R 6 Form a substituted or unsubstituted ring;
the R is g 、R h Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R is g 、R h Form a substituted or unsubstituted ring;
the R is i Independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the a 1 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 3 Independently selected from 0, 1, 2, 3 or 4.
6. The fused ring compound according to claim 1, wherein Ar 1 、Ar 2 At least one of which is selected from the group represented by formula III, and the remainder is selected from any one of the following structures:
the R is 5 、R 6 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
the R is g 、R h 、R i Is as defined in formula I;
the a 1 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 3 Independently selected from 0, 1, 2, 3 or 4, said a 4 Independently selected from 0, 1, 2, 3, 4 or 5, said a 5 Independently selected from 0, 1, 2, 3 or 4, said a 6 Independently selected from 0, 1, 2 or 3, said a 7 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 8 Independently selected from 0, 1 or 2, said a 9 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said a 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
7. The fused ring compound according to claim 1, wherein L 0 、L 1 、L 2 Independently selected from a single bond or any one of the following groups:
the R is 7 Independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
The c 1 Independently selected from 0, 1, 2, 3 or 4, said c 2 Independently selected from 0, 1, 2 or 3, said c 3 Independently selected from 0, 1 or 2, said c 4 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said c 5 Independently selected from 0, 1, 2, 3, 4 or 5, said c 6 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said c 7 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
8. The fused ring compound according to claim 1, wherein the fused ring compound is selected from any one of the following structures:
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9. an organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one or more of the condensed-cyclic compounds according to any one of claims 1 to 8.
10. The organic electroluminescent device according to claim 9, wherein the organic layer comprises at least one of a light-emitting layer, an electron-transporting layer, or a hole-blocking layer, and wherein at least one of the light-emitting layer, the electron-transporting layer, or the hole-blocking layer comprises at least one or more of the condensed-cyclic compounds according to any one of claims 1 to 8.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310797451.1A CN116903600A (en) | 2023-06-30 | 2023-06-30 | Condensed ring compound and organic electroluminescent device thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310797451.1A CN116903600A (en) | 2023-06-30 | 2023-06-30 | Condensed ring compound and organic electroluminescent device thereof |
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| CN116903600A true CN116903600A (en) | 2023-10-20 |
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| CN202310797451.1A Pending CN116903600A (en) | 2023-06-30 | 2023-06-30 | Condensed ring compound and organic electroluminescent device thereof |
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| Country | Link |
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| CN (1) | CN116903600A (en) |
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