WO2024131166A1 - Nitrogen-containing compound, and organic electroluminescent device and electronic apparatus - Google Patents
Nitrogen-containing compound, and organic electroluminescent device and electronic apparatus Download PDFInfo
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- WO2024131166A1 WO2024131166A1 PCT/CN2023/119239 CN2023119239W WO2024131166A1 WO 2024131166 A1 WO2024131166 A1 WO 2024131166A1 CN 2023119239 W CN2023119239 W CN 2023119239W WO 2024131166 A1 WO2024131166 A1 WO 2024131166A1
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- carbon atoms
- substituted
- unsubstituted
- nitrogen
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 129
- 239000010410 layer Substances 0.000 claims description 97
- 125000003118 aryl group Chemical group 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- 229910052805 deuterium Inorganic materials 0.000 claims description 25
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 239000002346 layers by function Substances 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 13
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
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- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005551 pyridylene group Chemical group 0.000 claims description 4
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- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000463 material Substances 0.000 abstract description 49
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- 238000005215 recombination Methods 0.000 abstract description 3
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- 239000011777 magnesium Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 5
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- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
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- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
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- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
Classifications
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/1062—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with oxygen
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- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Definitions
- the present application relates to the technical field of organic electroluminescent materials, and in particular to nitrogen-containing compounds and organic electroluminescent devices and electronic devices.
- Organic electroluminescent devices generally include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode.
- the functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field.
- the electrons on the cathode side move toward the organic light-emitting layer, and the holes on the anode side also move toward the organic light-emitting layer.
- the electrons and holes combine in the electroluminescent layer to form excitons.
- the excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light outward.
- the main problems of existing organic electroluminescent devices are lifespan and efficiency. As the display area becomes larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices.
- the purpose of the present application is to provide a nitrogen-containing compound and an organic electroluminescent device and an electronic device containing the same.
- the nitrogen-containing compound is used in an organic electroluminescent device to improve the performance of the device.
- a nitrogen-containing compound is provided, wherein the nitrogen-containing compound has a structure shown in the following formula 1:
- L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
- Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms
- Ar 1 and Ar 2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
- R 1 , R 2 and R 3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;
- n 1 is selected from 0, 1, 2, 3 or 4;
- n 2 is selected from 0, 1, 2, 3, 4, 5 or 6;
- n 3 is selected from 0, 1, 2, 3, 4, 5 or 6;
- the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.
- an organic electroluminescent device comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned nitrogen-containing compound.
- an electronic device comprising the organic electroluminescent device described in the second aspect.
- the compound of the present application uses a pentahedral fused indole as the parent core structure, and the parent core is connected to an electron-deficient heteroaryl group, as a single-type red light host material or an electron-transporting host material in a mixed red light host material.
- the parent core of the pentahedral fused indole has a large conjugated system, and after connecting it to an electron-deficient heteroaryl group, it can enhance the intermolecular force and improve the carrier mobility of the compound; on the other hand, the two benzene rings at the end of the pentahedral are staggered from each other due to steric hindrance, and are located in the upper and lower planes, respectively, so that the stacking and stacking between molecules can be suppressed to a certain extent, thereby improving the film-forming property of the compound.
- the compound of the present application when used as a red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminous efficiency and life.
- FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
- FIG. 2 is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.
- Electron injection layer 400 Electronic device
- the present application provides a nitrogen-containing compound having a structure shown in the following formula 1:
- L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
- Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms
- Ar 1 and Ar 2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
- R 1 , R 2 and R 3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;
- n 1 is selected from 0, 1, 2, 3 or 4;
- n 2 is selected from 0, 1, 2, 3, 4, 5 or 6;
- n 3 is selected from 0, 1, 2, 3, 4, 5 or 6;
- the substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.
- any two adjacent substituents form a ring means that the two substituents may or may not form a ring, that is, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring.
- any two adjacent substituents form a ring means that any two adjacent substituents among L, L 1 , L 2 , Ar 1 and Ar 2 are connected to each other to form a ring, or any two adjacent substituents among Ar 1 and Ar 2 may also exist independently.
- Any two adjacent may include two substituents on the same atom, and may also include one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is one substituent on each of two adjacent atoms, the two substituents may be fused into a ring.
- each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means:
- Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other;
- Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
- substituted or unsubstituted means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc).
- substituted or unsubstituted aryl refers to an aryl group having a substituent Rc or an unsubstituted aryl group.
- the above-mentioned substituent i.e., Rc
- Rc can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a deuterated aryl group, a haloaryl group, a cycloalkyl group, etc.
- the number of substitutions can be 1 or more.
- plural means more than 2, for example, 2, 3, 4, 5, 6, etc.
- the hydrogen atoms in the structure of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).
- the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms.
- L is a substituted arylene group having 12 carbon atoms
- the total number of carbon atoms of the arylene group and the substituents thereon is 12.
- aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
- Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl.
- aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl connected by a carbon-carbon single bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon single bond, and two or more condensed ring aryl connected by a carbon-carbon single bond.
- condensed ring aryl can, for example, include a dicyclic condensed aryl (e.g., naphthyl), a tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc.
- Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si.
- aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, phenyl-naphthyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.
- the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.
- terphenyl includes
- the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group.
- a substituted aryl group with 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents is 18.
- the carbon number of the substituted or unsubstituted aryl (arylene) can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 29, 30, 31, 32, 33, 34, 35, 36, 38 or 40, etc.
- the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 40 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 25 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 15 carbon atoms.
- the fluorenyl group may be substituted by one or more substituents.
- the substituted fluorenyl group may be: etc., but not limited thereto.
- the aryl group as a substituent of L, L 1 , L 2 , Ar 1 and Ar 2 includes, but is not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl and the like.
- heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S.
- the heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems connected by a carbon-carbon single bond, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring.
- the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, an
- the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.
- the number of carbon atoms of the substituted or unsubstituted heteroaryl can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40, etc.
- the substituted or unsubstituted heteroaryl is a total carbon atom.
- the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 3 to 40.
- the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 3 to 30. In some other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 5 to 12.
- heteroaryl groups as substituents for L, L 1 , L 2 , Ar 1 and Ar 2 include, but are not limited to, pyridyl, carbazolyl, quinolyl, isoquinolyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothienyl and dibenzofuranyl.
- the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc.
- groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc.
- the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
- the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms.
- the number of carbon atoms of the alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
- the halogen group is, for example, fluorine, chlorine, bromine, or iodine.
- trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
- haloalkyl group examples include, but are not limited to, trifluoromethyl.
- deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
- a deuterated aryl group refers to an aryl group containing deuterium, such as but not limited to, a deuterated phenyl group, a deuterated naphthyl group, a deuterated biphenyl group, and the like.
- the halogenated aryl group refers to an aryl group with a halogen substituent, such as but not limited to fluorophenyl, fluoronaphthyl, fluorobiphenyl and the like.
- the carbon number of the cycloalkyl group having 3 to 10 carbon atoms is, for example, 3, 4, 5, 6, 7, 8 or 10.
- Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
- no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.
- the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring.
- the meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):
- the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):
- the non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system.
- the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (Y-7):
- each R1 , R2 and R3 are the same or different and are each independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
- Het is selected from the following groups:
- ——# indicates the bond connected to L, represents a bond connected to L1 , Represents a bond connected to L2 ; the formula does not contain , which represents the location connected to In this case, L2 is a single bond and Ar2 is hydrogen.
- Het is selected from the following groups:
- ——# indicates the bond connected to L, represents a bond connected to L1 , Represents a bond connected to L2 ; the formula does not contain , which represents the location connected to In this case, L2 is a single bond and Ar2 is hydrogen.
- L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.
- L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
- the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group.
- L, L1 and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted dibenzothienylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolylene.
- the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
- L, L1 and L2 are the same or different and are each independently selected from a single bond or the following groups:
- L is selected from a single bond or the following groups:
- L1 and L2 are each independently selected from a single bond or the following groups:
- Ar1 is selected from substituted or unsubstituted aryl having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl having 12 to 18 carbon atoms;
- Ar2 is selected from hydrogen, substituted or unsubstituted aryl having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl having 12 to 18 carbon atoms.
- Ar1 is selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 12, 13, 14, 15, 16, 17 or 18 carbon atoms;
- Ar2 is selected from hydrogen, substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
- the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, and a trialkylsilyl group having 3 to 8 carbon atoms.
- any two adjacent substituents form a benzene ring or a fluorene ring.
- Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl;
- Ar 2 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.
- the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; optionally, in Ar 1 and Ar 2 , any two adjacent substituents form a benzene ring or a fluorenyl ring.
- Ar 1 is selected from a substituted or unsubstituted group V
- Ar 2 is selected from hydrogen, a substituted or unsubstituted group V
- the unsubstituted group V is selected from the following groups:
- the substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of substituents on the group V is greater than 1, each substituent is the same or different.
- substituents each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl,
- Ar 1 is selected from the following groups;
- Ar 2 is selected from hydrogen or the following groups:
- Formula 1 Selected from the group consisting of the following groups is selected from hydrogen or the following groups:
- L is selected from a single bond or the following groups:
- Het is selected from: ——# indicates the bond connected to L, represents a bond connected to L1 , represents the bond connected to L2 ,
- L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group.
- the substituents in L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl,
- Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,
- Ar2 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,
- the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
- Het is selected from: ——# indicates the bond connected to L, represents a bond connected to L1 , and
- L1 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group;
- the substituents in L1 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl,
- Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,
- the substituents in Ar 1 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
- the nitrogen-containing compound is selected from the group consisting of:
- an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the nitrogen-containing compound described in the first aspect of the present application.
- the nitrogen-containing compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifespan of the organic electroluminescent device.
- the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the nitrogen-containing compound.
- the organic light-emitting layer can be composed of the nitrogen-containing compound provided in the present application, or can be composed of the nitrogen-containing compound provided in the present application and other materials.
- the organic electroluminescent device is shown in Figure 1, and the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer (hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 which are stacked in sequence.
- anode 100 a hole injection layer 310, a hole transport layer 321, an electron blocking layer (hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 which are stacked in sequence.
- the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer.
- the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto.
- a transparent electrode including indium tin oxide (indium tin oxide) (ITO) as an anode is included.
- the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may be specifically selected from the following compounds or any combination thereof:
- the hole transport layer 321 may be composed of HT-1.
- the electron blocking layer 322 is composed of HT-2.
- a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321.
- the hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto.
- the material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;
- the hole injection layer 310 is composed of PD and HT-1.
- the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material.
- the organic light-emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
- the host material of the organic light-emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials.
- the host material includes the nitrogen-containing compound of the present application.
- the guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this.
- the guest material is also called a doping material or a dopant. According to the type of light emission, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,
- the organic electroluminescent device is a red organic electroluminescent device.
- the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application.
- the guest material is, for example, RD-1.
- the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application and RH-P The guest material is, for example, RD-1.
- the organic electroluminescent device is a green organic electroluminescent device.
- the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application.
- the guest material is, for example, fac-Ir(ppy) 3 .
- the electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not specifically limit this.
- the materials of the electron transport layer 340 include but are not limited to the following compounds:
- the electron transport layer 340 may be composed of ET-1 and LiQ.
- the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
- cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al, Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca.
- a metal electrode containing magnesium and silver is included as the cathode.
- an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340.
- the electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance.
- the electron injection layer 350 may include ytterbium (Yb).
- a third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.
- the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device.
- the electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.
- RM-1 25.0 g, 70 mmol
- tetrahydrofuran dried, 250 mL
- n-butyl lithium solution 2.0 M n-hexane solution, 38.5 mL, 77 mmol
- trimethyl borate 10.91 g, 105 mmol
- dilute hydrochloric acid (2 M, 58 mL) was added dropwise to the reaction solution, and stirred for 30 minutes
- dichloromethane was extracted (100 mL ⁇ 3 times), the organic phases were combined and dried with anhydrous magnesium sulfate
- o-bromonitrobenzene (10.0 g, 50 mmol), Sub-a1 (17.72 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (200 mL), anhydrous ethanol (50 mL) and deionized water (50 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 16 hours.
- RM-2 (17.10 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (160 mL), anhydrous ethanol (40 mL) and deionized water (40 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 16 hours.
- 3-chlorophenylboronic acid (8.60 g, 55 mmol)
- tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol
- tetrabutylammonium bromide (1.61
- reactant E shown in Table 3 was used to replace Sub-d1 to synthesize the compounds of the present application in Table 3.
- NMR of compound 193 1 H-NMR (400 MHz, Methylene-Chloride-D 2 ) ⁇ ppm 8.58 (d, 1H), 8.46 (d, 1H), 8.31 (d, 1H), 8.16 (s, 1H), 8.12-7.80 (m, 14H), 7.60-7.54 (m, 4H), 7.52-7.42 (m, 3H), 7.37-7.27 (m, 2H).
- Example 1 Red organic electroluminescent device
- the anode pretreatment is carried out through the following process: the thickness is On the ITO/Ag/ITO substrate, the surface is treated by using ultraviolet ozone and O 2 :N 2 plasma to increase the work function of the anode, and the surface of the ITO substrate is cleaned by using an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
- PD was vacuum-deposited on the experimental substrate (anode) to form a Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.
- Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of electron blocking layer.
- compound 4:RH-P:RD was co-deposited on the electron blocking layer at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of The red light emitting layer (EML)
- ETL electron transport layer
- Ag silver
- CPL-1 is vacuum-deposited on the cathode to form a layer with a thickness of The covering layer is formed, thereby completing the manufacture of the red organic electroluminescent device.
- An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound X in the following Table 4 was used instead of the compound 4 in Example 1 when preparing the light-emitting layer.
- An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B and compound C were used to replace compound 4 in Example 1 when preparing the light-emitting layer.
- the red organic electroluminescent devices prepared in Examples 1 to 27 and Comparative Examples 1 to 3 were subjected to performance tests. Specifically, the IVL performance of the devices was tested under the condition of 10 mA/cm 2 , and the T95 device life was tested under the condition of 20 mA/cm 2. The test results are shown in Table 4.
- Example 28 Red organic electroluminescent device
- the anode pretreatment is carried out through the following process: the thickness is On the ITO/Ag/ITO substrate, the surface is treated by using ultraviolet ozone and O 2 :N 2 plasma to increase the work function of the anode, and the surface of the ITO substrate is cleaned by using an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
- PD:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a film with a thickness of Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.
- Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of electron blocking layer.
- compound 110:RD-1 was co-evaporated on the electron blocking layer at an evaporation rate ratio of 98%:2% to form a layer with a thickness of The red light emitting layer (EML)
- ETL electron transport layer
- CPL-1 is vacuum-deposited on the cathode to form a layer with a thickness of The covering layer is formed, thereby completing the manufacture of the red organic electroluminescent device.
- An organic electroluminescent device was prepared by the same method as in Example 28, except that compound Y in the following Table 5 was used instead of compound 110 in Example 28 when preparing the light-emitting layer.
- An organic electroluminescent device was prepared by the same method as in Example 28, except that compound D, compound E and compound F were used respectively to replace compound 110 in Example 28 when preparing the light-emitting layer.
- the red organic electroluminescent devices prepared in Examples 28 to 38 and Comparative Examples 4 to 6 were subjected to performance tests. Specifically, the IVL performance of the devices was tested under the condition of 10 mA/cm 2 , and the T95 device life was tested under the condition of 20 mA/cm 2. The test results are shown in Table 5.
- the structure of the compound of the present application contains a parent core structure of a five-spiralene-fused indole, and the parent core is connected to an electron-deficient heteroaryl group through a connecting group, as a single-type red light host material or an electron-transporting host material in a mixed host material.
- the parent core of the five-spiralene-fused indole has a large conjugated system, and after connecting it with triazine, it can enhance the intermolecular force and improve the carrier mobility of the compound; on the other hand, the two benzene rings at the end of the five-spiralene are staggered from each other due to steric hindrance, and are located in the upper and lower planes respectively, thereby being able to suppress the stacking and accumulation of molecules to a certain extent and improve the film-forming property of the compound.
- the compound of the present application when used as a red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminous efficiency and life.
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Abstract
The present application relates to the technical field of organic electroluminescent materials, and provides a nitrogen-containing compound, and an organic electroluminescent device and an electronic apparatus comprising same. In the compound of the present application, a pentahelicene-fused indole is used as the core structure of the compound, and when the compound of the present application is used as the main material of a light-emitting layer, the carrier balance of the light-emitting layer can be improved, the carrier recombination region is widened, the efficiency of exciton generation and utilization is improved, and the light-emitting efficiency and service life of the device are improved.
Description
相关申请的交叉引用CROSS-REFERENCE TO RELATED APPLICATIONS
本申请要求于2022年12月19日递交的申请号为202211633378.6的中国专利申请的优先权，在此引用上述中国专利申请的内容全文以作为本申请的一部分。This application claims priority to Chinese patent application No. 202211633378.6 filed on December 19, 2022. The full text of the above Chinese patent application is hereby cited as part of this application.
本申请涉及有机电致发光材料技术领域，尤其涉及含氮化合物及有机电致发光器件和电子装置。The present application relates to the technical field of organic electroluminescent materials, and in particular to nitrogen-containing compounds and organic electroluminescent devices and electronic devices.
随着电子技术的发展和材料科学的进步，用于实现电致发光或者光电转化的电子元器件的应用范围越来越广泛。有机电致发光器件(OLED)，通常包括相对设置的阴极和阳极，以及设置于阴极和阳极之间的功能层。该功能层由多层有机或者无机膜层组成，且一般包括有机发光层、空穴传输层、电子传输层等。当阴阳两极施加电压时，两电极产生电场，在电场的作用下，阴极侧的电子向有机发光层移动，阳极侧的空穴也向有机发光层移动，电子和空穴在电致发光层结合形成激子，激子处于激发态向外释放能量，进而使得有机发光层对外发光。With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Organic electroluminescent devices (OLEDs) generally include a cathode and an anode arranged relatively to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the organic light-emitting layer, and the holes on the anode side also move toward the organic light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the organic light-emitting layer to emit light outward.
现有的有机电致发光器件中，最主要的问题体现在寿命和效率，随着显示器的大面积化，驱动电压也随之提高，发光效率及电流效率也需要提高，因此，有必要继续研发新型的材料，以进一步提高有机电致发光器件的性能。The main problems of existing organic electroluminescent devices are lifespan and efficiency. As the display area becomes larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices.
发明内容Summary of the invention
针对现有技术存在的上述问题，本申请的目的在于提供一种含氮化合物及包含其的有机电致发光器件和电子装置，该含氮化合物用于有机电致发光器件中，可以提高器件的性能。In view of the above problems existing in the prior art, the purpose of the present application is to provide a nitrogen-containing compound and an organic electroluminescent device and an electronic device containing the same. The nitrogen-containing compound is used in an organic electroluminescent device to improve the performance of the device.
根据本申请的第一方面，提供一种含氮化合物，所述含氮化合物具有以下式1所示的结构：
According to a first aspect of the present application, a nitrogen-containing compound is provided, wherein the nitrogen-containing compound has a structure shown in the following formula 1:
According to a first aspect of the present application, a nitrogen-containing compound is provided, wherein the nitrogen-containing compound has a structure shown in the following formula 1:
其中，L、L1和L2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；wherein L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Het是碳原子数为3～20的含氮亚杂芳基；Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;
Ar1和Ar2相同或不同，且各自独立地选自氢、碳原子数为6～40的取代或未取代的芳基、碳原子数为3～40的取代或未取代的杂芳基；Ar 1 and Ar 2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
各R1、R2和R3相同或者不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为3～12的三烷基硅基、三苯基硅基、碳原子数为6～20的芳基、碳原子数为6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～20的杂芳基、碳原子数为3～10的环烷基；Each of R 1 , R 2 and R 3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;
n1选自0、1、2、3或4；n 1 is selected from 0, 1, 2, 3 or 4;
n2选自0、1、2、3、4、5或6；
n 2 is selected from 0, 1, 2, 3, 4, 5 or 6;
n3选自0、1、2、3、4、5或6；n 3 is selected from 0, 1, 2, 3, 4, 5 or 6;
L、L1、L2、Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为3～12的三烷基硅基、三苯基硅基、碳原子数为6～20的芳基、碳原子数为6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～20的杂芳基、碳原子数为3～10的环烷基；任选地，任意两个相邻的取代基形成饱和或不饱和的3～15元环。The substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.
根据本申请的第二方面，提供一种有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；所述功能层包含上述的含氮化合物。According to a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned nitrogen-containing compound.
根据本申请的第三方面，提供了一种电子装置，包括第二方面所述的有机电致发光器件。According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device described in the second aspect.
本申请化合物以五螺烯稠合吲哚作为母核结构，母核连接缺电子类杂芳基，作为单一型红光主体材料或者混合型红光主体材料中的电子传输型主体材料。一方面，五螺烯稠合吲哚的母核具有较大的共轭体系，将其与缺电子类杂芳基连接之后能够增强分子间作用力，提高化合物载流子迁移率；另一方面，五螺烯末端的两个苯环因为空间位阻的原因相互错开，分别位于上下两个平面，从而能够一定程度上抑制分子间的层叠堆积，进而提高化合物的成膜性。将本申请化合物作为红光主体材料时，可以改善发光层中载流子平衡，拓宽载流子复合区域，提高激子生成和利用效率，提高器件发光效率和寿命。The compound of the present application uses a pentahedral fused indole as the parent core structure, and the parent core is connected to an electron-deficient heteroaryl group, as a single-type red light host material or an electron-transporting host material in a mixed red light host material. On the one hand, the parent core of the pentahedral fused indole has a large conjugated system, and after connecting it to an electron-deficient heteroaryl group, it can enhance the intermolecular force and improve the carrier mobility of the compound; on the other hand, the two benzene rings at the end of the pentahedral are staggered from each other due to steric hindrance, and are located in the upper and lower planes, respectively, so that the stacking and stacking between molecules can be suppressed to a certain extent, thereby improving the film-forming property of the compound. When the compound of the present application is used as a red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminous efficiency and life.
附图是用来提供对本申请的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本申请，但并不构成对本申请的限制。The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.
图1是本申请一种实施方式的有机电致发光器件的结构示意图。FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
图2是本申请一种实施方式的电子装置的结构示意图。FIG. 2 is a schematic diagram of the structure of an electronic device according to an embodiment of the present application.
附图标记说明
100、阳极 200、阴极 300、功能层 310、空穴注入层
321、空穴传输层 322、电子阻挡层 330、有机发光层 340、电子传输层
350、电子注入层 400、电子装置Description of Reference Numerals
100, anode 200, cathode 300, functional layer 310, hole injection layer
321, hole transport layer 322, electron blocking layer 330, organic light emitting layer 340, electron transport layer
350. Electron injection layer 400. Electronic device
100、阳极 200、阴极 300、功能层 310、空穴注入层
321、空穴传输层 322、电子阻挡层 330、有机发光层 340、电子传输层
350、电子注入层 400、电子装置Description of Reference Numerals
100, anode 200, cathode 300, functional layer 310, hole injection layer
321, hole transport layer 322, electron blocking layer 330, organic light emitting layer 340, electron transport layer
350. Electron injection layer 400. Electronic device
现在将参考附图更全面地描述示例性实施方式。然而，示例性实施方式能够以多种形式实施，且不应被理解为限于在此阐述的范例；相反，提供这些实施例使得本申请将更加全面和完整，并将示例性实施方式的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多个实施方式中。在下面的描述中，提供许多具体细节从而给出对本申请的实施例的充分理解。Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of forms and should not be construed as being limited to the examples set forth herein; rather, these embodiments are provided so that the present application will be more comprehensive and complete and the concepts of the exemplary embodiments will be fully conveyed to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.
第一方面，本申请提供一种含氮化合物，所述含氮化合物具有以下式1所示的结构：
In a first aspect, the present application provides a nitrogen-containing compound having a structure shown in the following formula 1:
In a first aspect, the present application provides a nitrogen-containing compound having a structure shown in the following formula 1:
L、L1和L2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Het是碳原子数为3～20的含氮亚杂芳基；Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;
Ar1和Ar2相同或不同，且各自独立地选自氢、碳原子数为6～40的取代或未取代的芳基、碳原子数为3～40的取代或未取代的杂芳基；Ar 1 and Ar 2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
各R1、R2和R3相同或者不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为3～12的三烷基硅基、三苯基硅基、碳原子数为6～20的芳基、碳原子数为6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～20的杂芳基、碳原子数为3～10的环烷基；Each of R 1 , R 2 and R 3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;
n1选自0、1、2、3或4；n 1 is selected from 0, 1, 2, 3 or 4;
n2选自0、1、2、3、4、5或6；n 2 is selected from 0, 1, 2, 3, 4, 5 or 6;
n3选自0、1、2、3、4、5或6；n 3 is selected from 0, 1, 2, 3, 4, 5 or 6;
L、L1、L2、Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为3～12的三烷基硅基、三苯基硅基、碳原子数为6～20的芳基、碳原子数为6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～20的杂芳基、碳原子数为3～10的环烷基；任选地，任意两个相邻的取代基形成饱和或不饱和的3～15元环。The substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.
本申请中，术语“任选”、“任选地”意味着随后所描述的事件或者环境可以发生也可以不发生。例如，“任选地，任意两个相邻的取代基形成环”意味着这两个取代基可以形成环也可以不形成环，即包括：两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。再比如，“L、L1、L2、Ar1和Ar2中，任选地，任意两个相邻的取代基形成环”是指L、L1、L2、Ar1和Ar2中的任意两个相邻的取代基相互连接形成环，或者Ar1和Ar2中的任意两个相邻的取代基也可以各自独立的存在。“任意两个相邻”可以包括同一个原子上具有两个取代基，还可以包括两个相邻的原子上分别具有一个取代基；其中，当同一个原子上具有两个取代基时，两个取代基可以与其共同连接的原子形成饱和或不饱和的螺环；当两个相邻的原子上分别具有一个取代基时，这两个取代基可以稠合成环。In the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, that is, including: the scenario where two adjacent substituents form a ring and the scenario where two adjacent substituents do not form a ring. For another example, "Among L, L 1 , L 2 , Ar 1 and Ar 2 , optionally, any two adjacent substituents form a ring" means that any two adjacent substituents among L, L 1 , L 2 , Ar 1 and Ar 2 are connected to each other to form a ring, or any two adjacent substituents among Ar 1 and Ar 2 may also exist independently. "Any two adjacent" may include two substituents on the same atom, and may also include one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is one substituent on each of two adjacent atoms, the two substituents may be fused into a ring.
本申请中，所采用的描述方式“各……独立地为”与“……独立地为”和“……各自独立地为”可以互换，均应做广义理解，其既可以是指在不同基团中，相同符号之间所表达的具体选项之间互相不影响，也可以表示在相同的基团中，相同符号之间所表达的具体选项之间互相不影响。例如，其中，各q独立地为0、1、2或3，各R”独立地选自氢、氘、氟、氯”，其含义是：式Q-1表示苯环上有q个取代基R”，各个R”可以相同也可以不同，每个R”的选项之间互不影响；式Q-2表示联苯的每一个苯环上有q个取代基R”，两个苯环上的R”取代基的个数q可以相同或不同，各个R”可以相同也可以不同，每个R”的选项之间互不影响。In this application, the descriptions "each ... independently is" and "... independently is" and "... independently is" are interchangeable and should be understood in a broad sense, which can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
本申请中，“取代或未取代的”这样的术语是指，在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述，将取代基统称为Rc)。举例来讲，“取代或未取代的芳基”是指具有取代基Rc的芳基或者没有取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素基团、氰基、杂芳基、芳基、三烷基硅基、烷基、卤代烷基、氘代烷基、氘代芳基、卤代芳基、环烷基等。取代的个数可以是1个或多个。In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a deuterated alkyl group, a deuterated aryl group, a haloaryl group, a cycloalkyl group, etc. The number of substitutions can be 1 or more.
本申请中，“多个”是指2个以上，例如2个、3个、4个、5个、6个，等。In the present application, "plurality" means more than 2, for example, 2, 3, 4, 5, 6, etc.
本申请化合物结构中的氢原子，包括氢元素的各种同位素原子，例如氢(H)、氘(D)或氚
(T)。The hydrogen atoms in the structure of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).
本申请中，取代或未取代的官能团的碳原子数，指的是所有碳原子数。举例而言，若L为碳原子数为12的取代的亚芳基，则亚芳基及其上的取代基的所有碳原子数为12。In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms. For example, if L is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.
本申请中，芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基，换言之，芳基可以是单环芳基、稠环芳基、通过碳碳单键连接的两个或者更多个单环芳基、通过碳碳单键连接的单环芳基和稠环芳基、通过碳碳单键连接的两个或者更多个稠环芳基。即，除非另有说明，通过碳碳单键连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中，稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。芳基的实例可以包括但不限于，苯基、萘基、芴基、苯基-萘基、螺二芴基、蒽基、菲基、联苯基、三联苯基、三亚苯基、苝基、苯并[9,10]菲基、芘基、苯并荧蒽基、基等。In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl connected by a carbon-carbon single bond, a monocyclic aryl and a condensed ring aryl connected by a carbon-carbon single bond, and two or more condensed ring aryl connected by a carbon-carbon single bond. That is, unless otherwise indicated, two or more aromatic groups connected by a carbon-carbon single bond can also be regarded as aryl of the present application. Among them, condensed ring aryl can, for example, include a dicyclic condensed aryl (e.g., naphthyl), a tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, phenyl-naphthyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.
本申请中，涉及的亚芳基是指芳基进一步失去一个或多个氢原子所形成的二价或多价基团。In the present application, the arylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an aryl group.
本申请中，三联苯基包括
In the present application, terphenyl includes
本申请中，取代的芳基的碳原子数，指的是芳基和芳基上的取代基中的碳原子总数，例如碳原子数为18的取代的芳基，指的是芳基和取代基的总碳原子数为18。In the present application, the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group. For example, a substituted aryl group with 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents is 18.
本申请中，取代或未取代的芳基(亚芳基)的碳原子数可以为6、8、10、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、28、29、30、31、32、33、34、35、36、38或40等。在一些实施方式中，取代或未取代的芳基是碳原子数为6～40的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～30的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～25的取代或未取代的芳基，另一些实施方式中，取代或未取代的芳基是碳原子数为6～15的取代或未取代的芳基。In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 29, 30, 31, 32, 33, 34, 35, 36, 38 or 40, etc. In some embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 40 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 25 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl is a substituted or unsubstituted aryl having 6 to 15 carbon atoms.
本申请中，芴基可以被1个或多个取代基取代。在上述芴基被取代的情况下，取代的芴基可以为：等，但并不限定于此。In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.
本申请中，作为L、L1、L2、Ar1和Ar2的取代基的芳基，例如但不限于，苯基、萘基、菲基、联苯基、芴基、二甲基芴基等等。In the present application, the aryl group as a substituent of L, L 1 , L 2 , Ar 1 and Ar 2 includes, but is not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl and the like.
本申请中，杂芳基是指环中包含1、2、3、4、5或6个杂原子的一价芳香环或其衍生物，杂原子可以是B、O、N、P、Si、Se和S中的一种或多种。杂芳基可以是单环杂芳基或多环杂芳基，换言之，杂芳基可以是单个芳香环体系，也可以是通过碳碳单键连接的多个芳香环体系，且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地，杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-苯基咔唑基、N-吡啶基咔唑基、N-甲基咔唑基等，而不限于此。In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems connected by a carbon-carbon single bond, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.
本申请中，涉及的亚杂芳基是指杂芳基进一步失去一个或多个氢原子所形成的二价或多价基团。In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.
本申请中，取代或未取代的杂芳基(亚杂芳基)的碳原子数可以选自3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30、31、32、33、34、35、36、37、38、39或40等。在一些实施方式中，取代或未取代的杂芳基是总碳原
子数为3～40的取代或未取代的杂芳基，另一些实施方式中，取代或未取代的杂芳基是总碳原子数为3～30的取代或未取代的杂芳基，另一些实施方式中，取代或未取代的杂芳基是总碳原子数为5～12的取代或未取代的杂芳基。In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39 or 40, etc. In some embodiments, the substituted or unsubstituted heteroaryl is a total carbon atom. In some embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 3 to 40. In some other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 3 to 30. In some other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total carbon number of 5 to 12.
本申请中，作为L、L1、L2、Ar1和Ar2的取代基的杂芳基例如但不限于，吡啶基、咔唑基、喹啉基、异喹啉基、菲啰啉基、苯并噁唑基、苯并噻唑基、苯并咪唑基、二苯并噻吩基、二苯并呋喃基。In the present application, examples of heteroaryl groups as substituents for L, L 1 , L 2 , Ar 1 and Ar 2 include, but are not limited to, pyridyl, carbazolyl, quinolyl, isoquinolyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothienyl and dibenzofuranyl.
本申请中，取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、卤代烷基等基团取代。应当理解地是，取代的杂芳基的碳原子数，指的是杂芳基和杂芳基上的取代基的碳原子总数。In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc. It should be understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
本申请中，碳原子数为1～10的烷基可以包括碳原子数1至10的直链烷基和碳原子数3至10的支链烷基。烷基的碳原子数例如为1、2、3、4、5、6、7、8、9、10个，烷基的具体实例包括但不限于，甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基等。In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
本申请中，卤素基团例如为氟、氯、溴、碘。In the present application, the halogen group is, for example, fluorine, chlorine, bromine, or iodine.
本申请中，三烷基硅基的具体实例包括但不限于，三甲基硅基、三乙基硅基等。In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
本申请中，卤代烷基的具体实例包括但不限于，三氟甲基。In the present application, specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.
本申请中，氘代烷基的具体实例包括但不限于，三氘代甲基。In the present application, specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl groups.
本申请中，氘代芳基是指含有氘代的芳基，例如但不限于，氘代苯基、氘代萘基、氘代联苯基等。In the present application, a deuterated aryl group refers to an aryl group containing deuterium, such as but not limited to, a deuterated phenyl group, a deuterated naphthyl group, a deuterated biphenyl group, and the like.
本申请中，卤代芳基是指带有卤素取代基的芳基，例如但不限于，氟代苯基、氟代萘基、氟代联苯基等。In the present application, the halogenated aryl group refers to an aryl group with a halogen substituent, such as but not limited to fluorophenyl, fluoronaphthyl, fluorobiphenyl and the like.
本申请中，碳原子数为3～10的环烷基的碳原子数例如为3、4、5、6、7、8或10。环烷基的具体实例包括但不限于，环戊基、环己基、金刚烷基。In the present application, the carbon number of the cycloalkyl group having 3 to 10 carbon atoms is, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.
本申请中，不定位连接键涉及的从环体系中伸出的单键
其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置，另一端连接化合物分子其余部分。举例而言，如下式(f)中所示地，式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(f-1)～式(f-10)所示出的任一可能的连接方式：
In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):
In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):
再举例而言，如下式(X')中所示地，式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接，其所表示的含义，包括如式(X'-1)～式(X'-4)所示出的任一可能的连接方式：
For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):
For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):
本申请中的不定位取代基，指的是通过一个从环体系中央伸出的单键连接的取代基，其表示该取代基可以连接在该环体系中的任何可能位置。例如，如下式(Y)中所示地，式(Y)所表示的取代基R'通过一个不定位连接键与喹啉环连接，其所表示的含义，包括如式(Y-1)～式(Y-7)所示出的任一可能的连接方式：
The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (Y-7):
The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means that the substituent can be connected to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring through a non-positioning connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (Y-7):
在一些实施方式中，各R1、R2和R3相同或不同，且各自独立地选自氘、氰基、氟、三氘代甲基、三甲基硅基、三氟甲基、环戊基、环己基、金刚烷基、甲基、乙基、异丙基、叔丁基、苯基或萘基。In some embodiments, each R1 , R2 and R3 are the same or different and are each independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
在一些实施方式中，Het选自如下基团：
In some embodiments, Het is selected from the following groups:
In some embodiments, Het is selected from the following groups:
——#表示与L连接的键，表示与L1连接的键，表示与L2连接的键；式中不含有的，代表该位置所连接的中，L2为单键，Ar2为氢。——# indicates the bond connected to L, represents a bond connected to L1 , Represents a bond connected to L2 ; the formula does not contain , which represents the location connected to In this case, L2 is a single bond and Ar2 is hydrogen.
在一些实施方式中，Het选自如下基团：
In some embodiments, Het is selected from the following groups:
In some embodiments, Het is selected from the following groups:
——#表示与L连接的键，表示与L1连接的键，表示与L2连接的键；式中不含有的，代表该位置所连接的中，L2为单键，Ar2为氢。——# indicates the bond connected to L, represents a bond connected to L1 , Represents a bond connected to L2 ; the formula does not contain , which represents the location connected to In this case, L2 is a single bond and Ar2 is hydrogen.
在一些实施方式中，L、L1和L2相同或不同，且各自独立地选自单键、碳原子数为6～15的取代或未取代的亚芳基、碳原子数为5～18的取代或未取代的亚杂芳基。In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.
在一些实施方式中，L、L1和L2相同或不同，且各自独立地选自单键、碳原子数为6、7、8、9、10、11、12、13、14或15的取代或未取代的亚芳基、碳原子数为5、6、7、8、9、10、11、12、13、14、15、16、17或18的取代或未取代的亚杂芳基。In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
可选地，L、L1和L2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～4的烷基、碳原子数为3～8的三烷基硅基、碳原子数为1～4的氟代烷基、碳原子数为1～4的氘代烷基、苯基或萘基。Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group.
在一些实施方式中，L、L1和L2相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚芴基、取代或未取代的亚吡啶基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚咔唑基。In some embodiments, L, L1 and L2 are the same or different, and are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted dibenzothienylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolylene.
可选地，L、L1和L2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基或苯基。Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
在一些实施方式中，L、L1和L2相同或不同，且各自独立地选自单键或以下基团：
In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond or the following groups:
In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond or the following groups:
在一些实施方式中，L选自单键或以下基团：
In some embodiments, L is selected from a single bond or the following groups:
In some embodiments, L is selected from a single bond or the following groups:
在一些实施方式中，L1和L2各自独立地选自单键或以下基团：
In some embodiments, L1 and L2 are each independently selected from a single bond or the following groups:
In some embodiments, L1 and L2 are each independently selected from a single bond or the following groups:
在一些实施方式中，Ar1选自碳原子数为6～25的取代或未取代的芳基、碳原子数为12～18的取代或未取代的杂芳基；Ar2选自氢、碳原子数为6～25的取代或未取代的芳基、碳原子数为12～18的取代或未取代的杂芳基。In some embodiments, Ar1 is selected from substituted or unsubstituted aryl having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl having 12 to 18 carbon atoms; Ar2 is selected from hydrogen, substituted or unsubstituted aryl having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl having 12 to 18 carbon atoms.
在一些实施方式中，Ar1选自碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24或25的取代或未取代的芳基，碳原子数为12、13、14、15、16、17或18的取代或未取代的杂芳基；Ar2选自氢、碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24或25的取代或未取代的芳基，碳原子数为12、13、14、15、16、17或18的取代或未取代的杂芳基。In some embodiments, Ar1 is selected from substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 12, 13, 14, 15, 16, 17 or 18 carbon atoms; Ar2 is selected from hydrogen, substituted or unsubstituted aryl having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
在一些实施方式中，Ar1和Ar2中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的氘代烷基、碳原子数为5～10的环烷基、碳原子数为6～12的芳基、碳原子数为5～12的杂芳基、碳原子数为3～8的三烷基硅基，任选地，任意两个相邻的取代基形成苯环或芴环。In some embodiments, the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, and a trialkylsilyl group having 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
在一些实施方式中，Ar1选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的芘基、取代或未取代的三亚苯基、取代或未取代的螺二芴基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基；In some embodiments, Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl;
Ar2选自氢、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的芘基、取代或未取代的三亚苯基、取代或未取代的螺二芴基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基。Ar 2 is selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl.
可选地，Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、三甲基硅基、三氘代甲基、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、芴基、二苯并呋喃基、二苯并噻吩基或咔唑基；任选地，Ar1和Ar2中，任意两个相邻的取代基形成苯环或芴环。Optionally, the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; optionally, in Ar 1 and Ar 2 , any two adjacent substituents form a benzene ring or a fluorenyl ring.
在一些实施方式中，Ar1选自取代或未取代的基团V；Ar2选自氢、取代或未取代的基团V；其中，所述未取代的基团V选自如下基团：
In some embodiments, Ar 1 is selected from a substituted or unsubstituted group V; Ar 2 is selected from hydrogen, a substituted or unsubstituted group V; wherein the unsubstituted group V is selected from the following groups:
In some embodiments, Ar 1 is selected from a substituted or unsubstituted group V; Ar 2 is selected from hydrogen, a substituted or unsubstituted group V; wherein the unsubstituted group V is selected from the following groups:
取代的基团V中具有一个或两个以上取代基，取代基各自独立地选自氘、氟、氰基、三氘代甲基、三甲基硅基、三氟甲基、环戊基、环己基、金刚烷基、甲基、乙基、异丙基、叔丁基、苯基、萘基、吡啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并噁唑基或苯并噻唑基，且当基团V上的取代基个数大于1时，各取代基相同或不同。The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of substituents on the group V is greater than 1, each substituent is the same or different.
在一些实施方式中，Ar1选自以下基团；Ar2选自氢或如下基团：
In some embodiments, Ar 1 is selected from the following groups; Ar 2 is selected from hydrogen or the following groups:
In some embodiments, Ar 1 is selected from the following groups; Ar 2 is selected from hydrogen or the following groups:
在一些实施方式中，式1中选自以下基团构成的组，选自氢或以下基团：
In some embodiments, in Formula 1 Selected from the group consisting of the following groups, is selected from hydrogen or the following groups:
In some embodiments, in Formula 1 Selected from the group consisting of the following groups, is selected from hydrogen or the following groups:
在一些实施方式中，L选自单键或以下基团：
In some embodiments, L is selected from a single bond or the following groups:
In some embodiments, L is selected from a single bond or the following groups:
在一些实施方式中，式1中选自以下基团构成的组：
In some embodiments, in Formula 1 Selected from the group consisting of:
In some embodiments, in Formula 1 Selected from the group consisting of:
在一些实施方式中，式1中选自以下基团构成的组：
In some embodiments, in Formula 1 Selected from the group consisting of:
In some embodiments, in Formula 1 Selected from the group consisting of:
在一些实施方式中，Het选自：——#表示与L连接的键，表示与L1连接的键，表示与L2连接的键，In some embodiments, Het is selected from: ——# indicates the bond connected to L, represents a bond connected to L1 , represents the bond connected to L2 ,
L1和L2相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚芴基、取代或未取代的亚吡啶基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚咔唑基， L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group.
L1和L2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基或苯基，The substituents in L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl,
Ar1选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的芘基、取代或未取代的三亚苯基、取代或未取代的螺二芴基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基，Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,
Ar2选自取代或未取代的萘基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的芘基、取代或未取代的三亚苯基、取代或未取代的螺二芴基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基， Ar2 is selected from substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,
Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、三甲基硅基、三氘代甲基、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、芴基、二苯并呋喃基、二苯并噻吩基或咔唑基。The substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
另一种实施方式中，为氢，In another embodiment, For hydrogen,
Het选自：
——#表示与L连接的键，表示与L1连接的键，且Het is selected from:
——# indicates the bond connected to L, represents a bond connected to L1 , and
——#表示与L连接的键，表示与L1连接的键，且Het is selected from:
——# indicates the bond connected to L, represents a bond connected to L1 , and
L1选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚菲基、取代或未取代的亚芴基、取代或未取代的亚吡啶基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚咔唑基； L1 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group;
L1中的取代基相同或不同，且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基或苯基，The substituents in L1 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl,
Ar1选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的蒽基、取代或未取代的芘基、取代或未取代的三亚苯基、取代或未取代的螺二芴基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基，
Ar 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl,
Ar1中的取代基相同或不同，且各自独立地选自氘、氟、氰基、三甲基硅基、三氘代甲基、三氟甲基、环戊基、环己基、甲基、乙基、异丙基、叔丁基、苯基、萘基、联苯基、芴基、二苯并呋喃基、二苯并噻吩基或咔唑基。The substituents in Ar 1 are the same or different and are each independently selected from deuterium, fluorine, cyano, trimethylsilyl, trideuterated methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl.
在一些实施方式中，含氮化合物选自以下化合物构成的组：
In some embodiments, the nitrogen-containing compound is selected from the group consisting of:
In some embodiments, the nitrogen-containing compound is selected from the group consisting of:
本申请的第二方面，提供一种有机电致发光器件，包括阳极、阴极，以及设置在阳极与阴极之间的功能层；其中，功能层包含本申请第一方面所述的含氮化合物。In a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the nitrogen-containing compound described in the first aspect of the present application.
本申请所提供的含氮化合物可以用于形成功能层中的至少一个有机膜层，以改善有机电致发光器件的发光效率和寿命等特性。The nitrogen-containing compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifespan of the organic electroluminescent device.
可选地，所述功能层包括有机发光层，所述有机发光层包括所述含氮化合物。其中，有机发光层既可以由本申请所提供的含氮化合物组成，也可以由本申请所提供的含氮化合物和其他材料共同组成。Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the nitrogen-containing compound. The organic light-emitting layer can be composed of the nitrogen-containing compound provided in the present application, or can be composed of the nitrogen-containing compound provided in the present application and other materials.
按照一种具体的实施方式，所述有机电致发光器件如图1所示，有机电致发光器件可以包括依次层叠设置的阳极100、空穴注入层310、空穴传输层321、电子阻挡层(空穴辅助层)322、有机发光层330、电子传输层340、电子注入层350和阴极200。According to a specific embodiment, the organic electroluminescent device is shown in Figure 1, and the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 321, an electron blocking layer (hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 which are stacked in sequence.
本申请中，阳极100包括阳极材料，其优选地是有助于空穴注入至功能层中的具有大逸出功(功函数，work function)材料。阳极材料的具体实例包括:金属如镍、铂、钒、铬、铜、锌和金或它们的合金；金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO)；组合的金属和氧化物如ZnO:Al或SnO2:Sb；或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺，但不限于此。优选包括包含氧化铟锡(铟锡氧化物，indium tin oxide)(ITO)作为阳极的透明电极。In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO 2 :Sb; or conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, a transparent electrode including indium tin oxide (indium tin oxide) (ITO) as an anode is included.
本申请中，空穴传输层可以包括一种或者多种空穴传输材料，空穴传输层材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物，具体可以选自如下所示的化合物或者其任意组合：
In the present application, the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may be specifically selected from the following compounds or any combination thereof:
In the present application, the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may be specifically selected from the following compounds or any combination thereof:
在一种实施方式中，空穴传输层321可由HT-1组成。In one embodiment, the hole transport layer 321 may be composed of HT-1.
在一种实施方式中，电子阻挡层322由HT-2组成。In one embodiment, the electron blocking layer 322 is composed of HT-2.
可选地，在阳极100和空穴传输层321之间还设置有空穴注入层310，以增强向空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料，本申请对此不做特殊的限制。所述空穴注入层310的材料例如选自如下化合物或者其任意组合；
Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;
Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. The material of the hole injection layer 310 is, for example, selected from the following compounds or any combination thereof;
在一种实施方式中，空穴注入层310由PD和HT-1组成。In one embodiment, the hole injection layer 310 is composed of PD and HT-1.
本申请中，有机发光层330可以由单一发光材料组成，也可以包括主体材料和客体材料。可选地，有机发光层330由主体材料和客体材料组成，注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子，激子将能量传递给主体材料，主体材料将能量传递给客体材料，进而使得客体材料能够发光。In the present application, the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
有机发光层330的主体材料可以包含金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料。可选地，所述主体材料包含本申请的含氮化合物。The host material of the organic light-emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. Optionally, the host material includes the nitrogen-containing compound of the present application.
有机发光层330的客体材料可以为具有缩合芳基环的化合物或其衍生物、具有杂芳基环的化合物或其衍生物、芳香族胺衍生物或者其他材料，本申请对此不做特殊的限制。客体材料又称为掺杂材料或掺杂剂。按发光类型可以分为荧光掺杂剂和磷光掺杂剂。所述磷光掺杂剂的具体实例包括但不限于，
The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of light emission, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,
The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of light emission, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,
在本申请的一种实施方式中，所述有机电致发光器件为红色有机电致发光器件。在一种实施方式中，有机发光层330的主体材料包含本申请的含氮化合物。客体材料例如为RD-1。在另一种实施方式中，有机发光层330的主体材料包含本申请的含氮化合物和RH-P客体材料例如为RD-1。In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In one embodiment, the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application. The guest material is, for example, RD-1. In another embodiment, the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application and RH-P The guest material is, for example, RD-1.
在本申请的一种实施方式中，所述有机电致发光器件为绿色有机电致发光器件。在一种更具体的实施方式中，有机发光层330的主体材料包含本申请的含氮化合物。客体材料例如为fac-Ir(ppy)3。In one embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application. The guest material is, for example, fac-Ir(ppy) 3 .
电子传输层340可以为单层结构，也可以为多层结构，其可以包括一种或者多种电子传输材料，电子传输材料可以选自但不限于，BTB、LiQ、苯并咪唑衍生物、噁二唑衍生物、喹喔啉衍生物或者其他电子传输材料，本申请对此不作特殊限定。所述电子传输层340的材料包含但不限于以下化合物：
The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not specifically limit this. The materials of the electron transport layer 340 include but are not limited to the following compounds:
The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to BTB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not specifically limit this. The materials of the electron transport layer 340 include but are not limited to the following compounds:
在本申请的一种实施方式中，电子传输层340可以由ET-1和LiQ组成。In one embodiment of the present application, the electron transport layer 340 may be composed of ET-1 and LiQ.
本申请中，阴极200可以包括阴极材料，其是有助于电子注入至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于，金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金；或多层材料如LiF/Al、Liq/Al、LiO2/Al、LiF/Ca、LiF/Al和BaF2/Ca。可选地，包括包含镁和银的金属电极作为阴极。In the present application, the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al, Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca. Optionally, a metal electrode containing magnesium and silver is included as the cathode.
可选地，在阴极200和电子传输层340之间还设置有电子注入层350，以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料，或者可以包括碱金属与有机物的络合物。在本申请的一种实施方式中，电子注入层350可以包括镱(Yb)。Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).
本申请第三方面提供一种电子装置，包括本申请第二方面所述的有机电致发光器件。A third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.
按照一种实施方式，如图2所示，所提供的电子装置为电子装置400，其包括上述有机电致发光器件。电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置，例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。According to one embodiment, as shown in FIG2 , the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.
下面结合合成实施例来具体说明本申请的含氮化合物的合成方法，但是本公开并不因此而受到任何限制。The synthesis method of the nitrogen-containing compound of the present application is specifically described below in conjunction with synthesis examples, but the present disclosure is not limited thereby.
合成实施例Synthesis Example
所属领域的专业人员应该认识到，本申请所描述的化学反应可以用来合适地制备许多本申请的有机化合物，且用于制备本申请的化合物的其它方法都被认为是在本申请的范围之内。例如，根据本申请那些非例证的化合物的合成可以成功地被所属领域的技术人员通过修饰方法完成，如适当的保护干扰基团，通过利用其他已知的试剂除了本申请所描述的，或将反应条件做一些常规的修改。本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the organic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds of the synthetic methods not mentioned in the present invention are all raw materials obtained through commercial channels.
Sub-a1的合成：
Synthesis of Sub-a1:
Synthesis of Sub-a1:
氮气氛围下，向500mL三口瓶中加入RM-1(25.0g,70mmol)和四氢呋喃(干燥，250mL)；将体系降温至-78℃，滴加正丁基锂溶液(2.0M正己烷溶液,38.5mL，77mmol)，滴加完毕后保温(-78℃)搅拌1小时；保持-78℃，滴加硼酸三甲酯(10.91g,105mmol)，滴加完毕后继续保温(-78℃)1小时，然后让体系自然升温至室温；向反应液中滴加稀盐酸(2M，58mL)，搅拌30分钟；二氯甲烷萃取(100mL×3次)，合并有机相并用无水硫酸镁干燥，过滤后减压蒸馏除去溶剂，得粗品。粗品用正庚烷打浆，过滤得到白色固体产物(13.98g，收率62％)。Under nitrogen atmosphere, RM-1 (25.0 g, 70 mmol) and tetrahydrofuran (dried, 250 mL) were added to a 500 mL three-necked flask; the system was cooled to -78 °C, and n-butyl lithium solution (2.0 M n-hexane solution, 38.5 mL, 77 mmol) was added dropwise, and the temperature was kept at -78 °C for 1 hour after the addition was completed; trimethyl borate (10.91 g, 105 mmol) was added dropwise at -78 °C, and the temperature was kept at -78 °C for 1 hour after the addition was completed, and then the system was allowed to warm to room temperature naturally; dilute hydrochloric acid (2 M, 58 mL) was added dropwise to the reaction solution, and stirred for 30 minutes; dichloromethane was extracted (100 mL × 3 times), the organic phases were combined and dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was slurried with n-heptane and filtered to obtain a white solid product (13.98 g, yield 62%).
Sub-b1的合成:
Synthesis of Sub-b1:
Synthesis of Sub-b1:
氮气氛围下，向500mL三口瓶中依次加入邻溴硝基苯(10.0g，50mmol)，Sub-a1(17.72g，55mmol)，四(三苯基膦)钯(0.58g，0.5mmol)，四丁基溴化铵(1.61g，5mmol)，无水碳酸钾(13.82g，100mmol)，甲苯(200mL)，无水乙醇(50mL)和去离子水(50mL)，开启搅拌和加热，升温至回流反应16小时。待体系冷却至室温后，用二氯甲烷萃取(100mL×3次)，有机相用无水硫酸镁干燥，过滤后减压蒸馏除去溶剂，得粗品。粗品用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得黄色固体(14.75g，收率74％)。Under nitrogen atmosphere, o-bromonitrobenzene (10.0 g, 50 mmol), Sub-a1 (17.72 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (200 mL), anhydrous ethanol (50 mL) and deionized water (50 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 16 hours. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phase was dried with anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the mobile phase to obtain a yellow solid (14.75 g, yield 74%).
Sub-c1的合成:
Synthesis of Sub-c1:
Synthesis of Sub-c1:
氮气氛围下，向250mL三口瓶中，加入Sub-b1(20.0g，50mmol)，三苯基膦(32.78g，125mmol)和邻二氯苯(160mL)，开启搅拌和加热，升温至回流反应16h。待体系冷却至室温后，减压蒸馏除去溶剂，得粗品。粗品用正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体Sub-c1(10.5g，收率57％)。Under nitrogen atmosphere, add Sub-b1 (20.0 g, 50 mmol), triphenylphosphine (32.78 g, 125 mmol) and o-dichlorobenzene (160 mL) to a 250 mL three-necked flask, start stirring and heating, and raise the temperature to reflux reaction for 16 hours. After the system is cooled to room temperature, the solvent is removed by vacuum distillation to obtain a crude product. The crude product is purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a white solid Sub-c1 (10.5 g, yield 57%).
Sub-c2的合成：
Synthesis of Sub-c2:
Synthesis of Sub-c2:
氮气氛围下，向100mL三口瓶加入Sub-c1(9.18g,25mmol)和200mL苯-D6，升温至60℃后向其中添加三氟甲磺酸(22.51g,150mmol)，继续升温至沸腾搅拌反应24小时。待反应体系冷却至室温后，向其中添加50mL重水，搅拌10分钟后加入饱和K3PO4水溶液中和反应液。用二氯甲烷萃取有机层(50mL×3次)，合并有机相用无水硫酸钠干燥，过滤后减压蒸馏除去溶剂，得粗品。粗品使用正庚烷/二氯甲烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体(5.07g，收率53％)。Under nitrogen atmosphere, add Sub-c1 (9.18g, 25mmol) and 200mL benzene-D6 to a 100mL three-necked flask, heat to 60°C, add trifluoromethanesulfonic acid (22.51g, 150mmol), continue to heat to boiling and stir for 24 hours. After the reaction system is cooled to room temperature, add 50mL of heavy water, stir for 10 minutes, and then add saturated K 3 PO 4 aqueous solution to neutralize the reaction solution. Extract the organic layer with dichloromethane (50mL×3 times), combine the organic phases, dry them with anhydrous sodium sulfate, filter and distill under reduced pressure to remove the solvent to obtain a crude product. The crude product is purified by silica gel column chromatography using n-heptane/dichloromethane as the mobile phase to obtain a white solid (5.07g, yield 53%).
Sub-d1的合成：
Sub-d1 Synthesis:
Sub-d1 Synthesis:
氮气氛围下，向500mL三口瓶中依次加入RM-2(17.10g，50mmol)，3-氯苯硼酸(8.60g，55mmol)，四(三苯基膦)钯(0.58g，0.5mmol)，四丁基溴化铵(1.61g，5mmol)，无水碳酸钾(13.82g，100mmol)，甲苯(160mL)，无水乙醇(40mL)和去离子水(40mL)，开启搅拌和加热，升温至回流反应16小时。待体系冷却至室温后，用二氯甲烷萃取(100mL×3次)，有机相用无水硫酸镁干燥后，过滤后减压蒸馏除去溶剂，得粗品。粗品用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得白色固体(17.14g，收率82％)。Under nitrogen atmosphere, RM-2 (17.10 g, 50 mmol), 3-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (1.61 g, 5 mmol), anhydrous potassium carbonate (13.82 g, 100 mmol), toluene (160 mL), anhydrous ethanol (40 mL) and deionized water (40 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 16 hours. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phase was dried with anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the mobile phase to obtain a white solid (17.14 g, yield 82%).
参照Sub-d1的合成，使用表1中所示的反应物A替代RM-2，反应物B替代4-氯苯硼酸，合成Sub-d2至Sub-d10。Referring to the synthesis of Sub-d1, reactant A shown in Table 1 was used instead of RM-2, and reactant B was used instead of 4-chlorophenylboronic acid to synthesize Sub-d2 to Sub-d10.
表1：Sub-d2至Sub-d10的合成
Table 1: Synthesis of Sub-d2 to Sub-d10
Table 1: Synthesis of Sub-d2 to Sub-d10
化合物4的合成：
Synthesis of compound 4:
Synthesis of compound 4:
向1000mL三口瓶中依次加入Sub-1(18.35g，50mmol)，RM-3(26.80g，75mmol)和干燥的DMF(400mL)，将体系降温至-10℃，快速加入钠氢(60％含量，2.2g，55mmol)，搅拌反应过夜。将反应液倒入500mL去离子水中，充分搅拌30min后抽滤，滤固用去离子水洗至中性，再用无水乙醇(200mL)淋洗，得粗品。用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体(23.0g，产率67％,m/z＝689.3[M+H]+)。Sub-1 (18.35 g, 50 mmol), RM-3 (26.80 g, 75 mmol) and dry DMF (400 mL) were added to a 1000 mL three-necked flask in sequence, the system was cooled to -10 °C, sodium hydrogen (60% content, 2.2 g, 55 mmol) was quickly added, and the reaction was stirred overnight. The reaction solution was poured into 500 mL of deionized water, stirred for 30 min, and then filtered. The filtered solid was washed with deionized water until neutral, and then rinsed with anhydrous ethanol (200 mL) to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane/n-heptane as the mobile phase to obtain a white solid (23.0 g, yield 67%, m/z = 689.3 [M + H] + ).
参照化合物4的合成，使用表2中所示的,反应物C替代Sub-c1，反应物D替代RM-3，合成表2中的本申请化合物。Referring to the synthesis of compound 4, reactant C was used to replace Sub-c1, and reactant D was used to replace RM-3 as shown in Table 2 to synthesize the compounds of the present application in Table 2.
表2：本申请化合物的合成
Table 2: Synthesis of compounds of the present application
Table 2: Synthesis of compounds of the present application
化合物110的合成：
Synthesis of compound 110:
Synthesis of compound 110:
氮气氛围下，向500mL三口瓶中依次加入Sub-c1(18.35g，50mmol)，Sub-d1(23.0g，55mmol)，三(二亚苄基丙酮)二钯(Pd2(dba)3，0.916g，1mmol)，(2-二环己基膦-2',4',6'三异丙基联苯)(X-Phos，0.95g，2mmol)，叔丁醇钠(t-BuONa，9.61g，100mmol)和二甲苯(xylene，250mL)，升温至回流，搅拌反应过夜；待体系降温至室温后，将反应液倒入500mL去离子水中，充分搅拌30分钟，抽滤，滤饼用去离子水淋洗至中性，再用无水乙醇淋洗(200mL)，得粗品；用二氯甲烷/正庚烷作为流动相对粗品进行硅胶柱色谱提纯，得到白色固体(25.10g，产率67％,m/z＝750.3[M+H]+)。Under nitrogen atmosphere, Sub-c1 (18.35 g, 50 mmol), Sub-d1 (23.0 g, 55 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.916 g, 1 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (X-Phos, 0.95 g, 2 mmol), sodium tert-butoxide (t-BuONa, 9.61 g, 100 mm ol) and xylene (xylene, 250mL), heat to reflux, stir and react overnight; after the system is cooled to room temperature, pour the reaction solution into 500mL deionized water, stir thoroughly for 30 minutes, filter, rinse the filter cake with deionized water until neutral, and then rinse with anhydrous ethanol (200mL) to obtain a crude product; use dichloromethane/n-heptane as the mobile phase to purify the crude product by silica gel column chromatography to obtain a white solid (25.10g, yield 67%, m/z＝750.3[M+H] + ).
参照化合物110的合成，使用表3中所示的反应物E替代Sub-d1，合成表3中的本申请化合物。Referring to the synthesis of compound 110, reactant E shown in Table 3 was used to replace Sub-d1 to synthesize the compounds of the present application in Table 3.
表3：本申请化合物的合成
Table 3: Synthesis of compounds of the present application
Table 3: Synthesis of compounds of the present application
化合物7核磁：1H-NMR(400MHz,Methylene-Chloride-D2)δppm 8.66(d,1H),8.58(d,1H),8.54-8.49(m,4H),8.40(d,1H),8.25(d,1H),8.07-7.86(m,8H),7.61-7.32(m,11H),7.26(t,1H)；Compound 7 NMR: 1 H-NMR (400MHz, Methylene-Chloride-D 2 )δppm 8.66(d,1H),8.58(d,1H),8.54-8.49(m,4H),8.40(d,1H),8.25(d,1H),8.07-7.86(m,8H),7.61-7.32(m,11H),7.26(t,1H);
化合物193核磁：1H-NMR(400MHz,Methylene-Chloride-D2)δppm 8.58(d,1H),8.46(d,1H),8.31(d,1H),8.16(s,1H),8.12-7.80(m,14H),7.60-7.54(m,4H),7.52-7.42(m,3H),7.37-7.27(m,2H)。NMR of compound 193: 1 H-NMR (400 MHz, Methylene-Chloride-D 2 ) δppm 8.58 (d, 1H), 8.46 (d, 1H), 8.31 (d, 1H), 8.16 (s, 1H), 8.12-7.80 (m, 14H), 7.60-7.54 (m, 4H), 7.52-7.42 (m, 3H), 7.37-7.27 (m, 2H).
有机电致发光器件制备及评估：Preparation and evaluation of organic electroluminescent devices:
实施例1：红色有机电致发光器件Example 1: Red organic electroluminescent device
先通过以下过程进行阳极预处理：在厚度依次为的ITO/Ag/ITO基板上，利用紫外臭氧以及O2:N2等离子进行表面处理，以增加阳极的功函数，采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的杂质及油污。First, the anode pretreatment is carried out through the following process: the thickness is On the ITO/Ag/ITO substrate, the surface is treated by using ultraviolet ozone and O 2 :N 2 plasma to increase the work function of the anode, and the surface of the ITO substrate is cleaned by using an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
在实验基板(阳极)上真空蒸镀PD以形成厚度为的空穴注入层(HIL)，然后在空穴注入层上真空蒸镀HT-1，形成厚度为的空穴传输层。PD was vacuum-deposited on the experimental substrate (anode) to form a Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.
在空穴传输层上真空蒸镀化合物HT-2，形成厚度为的电子阻挡层。Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of electron blocking layer.
接着，在电子阻挡层上，将化合物4:RH-P:RD以49％:49％:2％的蒸镀速率比例进行共同蒸镀，形成厚度为的红光发光层(EML)。Next, compound 4:RH-P:RD was co-deposited on the electron blocking layer at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of The red light emitting layer (EML)
在发光层上，将化合物ET-1和LiQ以1:1的重量比进行混合并蒸镀形成厚的电子传输层(ETL)，将Yb蒸镀在电子传输层上以形成厚度为的电子注入层(EIL)，然后将镁(Mg)和
银(Ag)以1:9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为的阴极。On the light-emitting layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of The electron injection layer (EIL) is then formed by mixing magnesium (Mg) and Silver (Ag) is mixed at a deposition rate of 1:9 and vacuum deposited on the electron injection layer to form a layer with a thickness of cathode.
此外，在上述阴极上真空蒸镀CPL-1形成厚度为的覆盖层，从而完成红色有机电致发光器件的制造。In addition, CPL-1 is vacuum-deposited on the cathode to form a layer with a thickness of The covering layer is formed, thereby completing the manufacture of the red organic electroluminescent device.
实施例2～27Embodiments 2 to 27
除了在制作发光层时，以下表4中的化合物X代替实施例1中的化合物4之外，利用与实施例1相同的方法制备有机电致发光器件。An organic electroluminescent device was prepared by the same method as in Example 1, except that the compound X in the following Table 4 was used instead of the compound 4 in Example 1 when preparing the light-emitting layer.
比较例1～3Comparative Examples 1 to 3
除了在制作发光层时，分别以化合物A、化合物B、化合物C代替实施例1中的化合物4之外，利用与实施例1相同的方法制备有机电致发光器件。An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B and compound C were used to replace compound 4 in Example 1 when preparing the light-emitting layer.
其中，在各实施例及比较例中，所用的化合物结构如下：
Among them, in each embodiment and comparative example, the compound structure used is as follows:
Among them, in each embodiment and comparative example, the compound structure used is as follows:
对实施例1～27和比较例1～3制备所得的红色有机电致发光器件进行性能测试，具体在10mA/cm2的条件下测试了器件的IVL性能，T95器件寿命在20mA/cm2的条件下进行测试，测试结果见表4。The red organic electroluminescent devices prepared in Examples 1 to 27 and Comparative Examples 1 to 3 were subjected to performance tests. Specifically, the IVL performance of the devices was tested under the condition of 10 mA/cm 2 , and the T95 device life was tested under the condition of 20 mA/cm 2. The test results are shown in Table 4.
表4
Table 4
Table 4
参考上表4可知，将本发明化合物用作混合型红光主体材料中的电子传输型主体材料时，实施例1～27，相比于比较例1～3而言，器件的发光效率(Cd/A)至少提高13.6％，T95寿命至少提高了14.6％。Referring to Table 4 above, it can be seen that when the compounds of the present invention are used as electron transport type host materials in mixed red light host materials, the luminous efficiency (Cd/A) of the devices in Examples 1 to 27 is at least increased by 13.6%, and the T95 life is at least increased by 14.6% compared to Comparative Examples 1 to 3.
实施例28：红色有机电致发光器件Example 28: Red organic electroluminescent device
先通过以下过程进行阳极预处理：在厚度依次为的ITO/Ag/ITO基板上，利用紫外臭氧以及O2:N2等离子进行表面处理，以增加阳极的功函数，采用有机溶剂清洗ITO基板表面，以清除ITO基板表面的杂质及油污。First, the anode pretreatment is carried out through the following process: the thickness is On the ITO/Ag/ITO substrate, the surface is treated by using ultraviolet ozone and O 2 :N 2 plasma to increase the work function of the anode, and the surface of the ITO substrate is cleaned by using an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.
在实验基板(阳极)上，将PD:HT-1以2％:98％的蒸镀速率比例进行共同蒸镀，形成厚度为的空穴注入层(HIL)，然后在空穴注入层上真空蒸镀HT-1,形成厚度为的空穴传输层。On the experimental substrate (anode), PD:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a film with a thickness of Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.
在空穴传输层上真空蒸镀化合物HT-2，形成厚度为的电子阻挡层。Compound HT-2 is vacuum-deposited on the hole transport layer to form a layer with a thickness of electron blocking layer.
接着，在电子阻挡层上，将化合物110:RD-1以98％:2％的蒸镀速率比例进行共同蒸镀，形成厚度为的红光发光层(EML)。Next, compound 110:RD-1 was co-evaporated on the electron blocking layer at an evaporation rate ratio of 98%:2% to form a layer with a thickness of The red light emitting layer (EML)
在发光层上，将化合物ET-1和LiQ以1:1的重量比进行混合并蒸镀形成厚的电子传输层(ETL)，将Yb蒸镀在电子传输层上以形成厚度为的电子注入层(EIL)，然后将镁(Mg)和银(Ag)以1:9的蒸镀速率混合，真空蒸镀在电子注入层上，形成厚度为的阴极。On the light-emitting layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a deposition rate of 1:9 and vacuum-deposited on the electron injection layer to form a layer with a thickness of cathode.
此外，在上述阴极上真空蒸镀CPL-1形成厚度为的覆盖层，从而完成红色有机电致发光器件的制造。In addition, CPL-1 is vacuum-deposited on the cathode to form a layer with a thickness of The covering layer is formed, thereby completing the manufacture of the red organic electroluminescent device.
实施例28～38Embodiments 28 to 38
除了在制作发光层时，以下表5中的化合物Y代替实施例28中的化合物110之外，利用与实施例28相同的方法制备有机电致发光器件。An organic electroluminescent device was prepared by the same method as in Example 28, except that compound Y in the following Table 5 was used instead of compound 110 in Example 28 when preparing the light-emitting layer.
比较例4～6Comparative Examples 4 to 6
除了在制作发光层时，分别以化合物D、化合物E、化合物F代替实施例28中的化合物110之外，利用与实施例28相同的方法制备有机电致发光器件。An organic electroluminescent device was prepared by the same method as in Example 28, except that compound D, compound E and compound F were used respectively to replace compound 110 in Example 28 when preparing the light-emitting layer.
其中，在实施例28～38及比较例4～6中，所用的化合物结构如下：
Among them, in Examples 28 to 38 and Comparative Examples 4 to 6, the structures of the compounds used are as follows:
Among them, in Examples 28 to 38 and Comparative Examples 4 to 6, the structures of the compounds used are as follows:
对实施例28～38和比较例4～6制备所得的红色有机电致发光器件进行性能测试，具体在10mA/cm2的条件下测试了器件的IVL性能，T95器件寿命在20mA/cm2的条件下进行测试，测试结果见表5。The red organic electroluminescent devices prepared in Examples 28 to 38 and Comparative Examples 4 to 6 were subjected to performance tests. Specifically, the IVL performance of the devices was tested under the condition of 10 mA/cm 2 , and the T95 device life was tested under the condition of 20 mA/cm 2. The test results are shown in Table 5.
表5
table 5
table 5
参考上表5可知，将本发明化合物用做红色有机电致发光器件的单一型主体材料时，实施例28～38，相比于比较例4～6而言，器件的发光效率(Cd/A)至少提高13.2％，T95寿命至少提高了11.3％。
Referring to Table 5 above, it can be seen that when the compounds of the present invention are used as a single-type host material of a red organic electroluminescent device, the luminous efficiency (Cd/A) of the device in Examples 28 to 38 is increased by at least 13.2%, and the T95 life is increased by at least 11.3% compared to Comparative Examples 4 to 6.
本申请化合物结构中包含五螺烯稠合吲哚的母核结构，母核通过连接基团连接缺电子类杂芳基，作为单一型红光主体材料或者混合型主体材料中的电子传输型主体材料。一方面，五螺烯稠合吲哚的母核具有较大的共轭体系，将其与三嗪连接之后能够增强分子间作用力，提高化合物载流子迁移率；另一方面，五螺烯末端的两个苯环因为空间位阻的原因相互错开，分别位于上下两个平面，从而能够一定程度上抑制分子间的层叠堆积，提高化合物的成膜性。将本申请化合物作为红光主体材料时，可以改善发光层中载流子平衡，拓宽载流子复合区域，提高激子生成和利用效率，提高器件发光效率和寿命。The structure of the compound of the present application contains a parent core structure of a five-spiralene-fused indole, and the parent core is connected to an electron-deficient heteroaryl group through a connecting group, as a single-type red light host material or an electron-transporting host material in a mixed host material. On the one hand, the parent core of the five-spiralene-fused indole has a large conjugated system, and after connecting it with triazine, it can enhance the intermolecular force and improve the carrier mobility of the compound; on the other hand, the two benzene rings at the end of the five-spiralene are staggered from each other due to steric hindrance, and are located in the upper and lower planes respectively, thereby being able to suppress the stacking and accumulation of molecules to a certain extent and improve the film-forming property of the compound. When the compound of the present application is used as a red light host material, it can improve the carrier balance in the light-emitting layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminous efficiency and life.
以上结合附图详细描述了本发明的优选实施方式，但是，本发明并不限于上述实施方式中的具体细节，在本发明的技术构思范围内，可以对本发明的技术方案进行多种简单变型，这些简单变型均属于本发明的保护范围。
The preferred embodiments of the present invention are described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.
Claims (13)
- 含氮化合物，其特征在于，其具有由以下式1所示结构：
The nitrogen-containing compound is characterized in that it has a structure represented by the following formula 1:
其中，L、L1和L2相同或不同，且各自独立地选自单键、碳原子数为6～30的取代或未取代的亚芳基、碳原子数为3～30的取代或未取代的亚杂芳基；wherein L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;Het是碳原子数为3～20的含氮亚杂芳基；Het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;Ar1和Ar2相同或不同，且各自独立地选自氢、碳原子数为6～40的取代或未取代的芳基、碳原子数为3～40的取代或未取代的杂芳基；Ar 1 and Ar 2 are the same or different and are each independently selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;各R1、R2和R3相同或者不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为3～12的三烷基硅基、三苯基硅基、碳原子数为6～20的芳基、碳原子数为6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～20的杂芳基、碳原子数为3～10的环烷基；Each of R 1 , R 2 and R 3 is the same or different and is independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, and cycloalkyl group having 3 to 10 carbon atoms;n1选自0、1、2、3或4；n 1 is selected from 0, 1, 2, 3 or 4;n2选自0、1、2、3、4、5或6；n 2 is selected from 0, 1, 2, 3, 4, 5 or 6;n3选自0、1、2、3、4、5或6；n 3 is selected from 0, 1, 2, 3, 4, 5 or 6;L、L1、L2、Ar1和Ar2中的取代基相同或不同，且各自独立地选自氘、氰基、卤素基团、碳原子数为1～10的烷基、碳原子数为1～10的卤代烷基、碳原子数为1～10的氘代烷基、碳原子数为3～12的三烷基硅基、三苯基硅基、碳原子数为6～20的芳基、碳原子数为6～20的氘代芳基、碳原子数为6～20的卤代芳基、碳原子数为3～20的杂芳基、碳原子数为3～10的环烷基；任选地，任意两个相邻的取代基形成饱和或不饱和的3～15元环。The substituents in L, L 1 , L 2 , Ar 1 and Ar 2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, halogenated alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triphenylsilyl group, aryl group having 6 to 20 carbon atoms, deuterated aryl group having 6 to 20 carbon atoms, halogenated aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring. - 根据权利要求1所述的含氮化合物，其中，Het选自如下基团：
The nitrogen-containing compound according to claim 1, wherein Het is selected from the following groups:
——#表示与L连接的键，表示与L1连接的键，表示与L2连接的键；式中不含有的，代表该位置所连接的中，L2为单键，Ar2为氢。 ——# indicates the bond connected to L, represents a bond connected to L1 , Represents a bond connected to L2 ; the formula does not contain , which represents the location connected to In this case, L2 is a single bond and Ar2 is hydrogen. - 根据权利要求1～2中任意一项所述的含氮化合物，其中，Ar1选自碳原子数为6～25的取代或未取代的芳基、碳原子数为12～18的取代或未取代的杂芳基；Ar2选自氢、碳原子数为6～25的取代或未取代的芳基、碳原子数为12～18的取代或未取代的杂芳基；The nitrogen-containing compound according to any one of claims 1 to 2, wherein Ar 1 is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; Ar 2 is selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms;可选地，Ar1和Ar2中的取代基各自独立地选自氘、卤素基团、氰基、碳原子数为1～4的烷基、碳原子数为1～4的卤代烷基、碳原子数为1～4的氘代烷基、碳原子数为5～10的环烷基、碳原子数为6～12的芳基、碳原子数为5～12的杂芳基、碳原子数为3～8的三烷基硅基，任选地，任意两个相邻的取代基形成苯环或芴环。Optionally, the substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, and a trialkylsilyl group having 3 to 8 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
- 根据权利要求1～3中任意一项所述的含氮化合物，其中，L、L1和L2相同或不同，且各自独立地选自单键、碳原子数为6～15的取代或未取代的亚芳基、碳原子数为5～18的取代或未取代的亚杂芳基；The nitrogen-containing compound according to any one of claims 1 to 3, wherein L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms;可选地，L、L1和L2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1～4的烷基、碳原子数为3～8的三烷基硅基、碳原子数为1～4的氟代烷基、碳原子数为1～4的氘代烷基、苯基或萘基。Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group.
- 根据权利要求1～4中任意一项所述的含氮化合物，其中，L、L1和L2相同或不同，且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚蒽基、取代或未取代的亚菲基、取代或未取代的亚芴基、取代或未取代的亚吡啶基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚咔唑基；The nitrogen-containing compound according to any one of claims 1 to 4, wherein L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolylene group;可选地，L、L1和L2中的取代基相同或不同，且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、三氘代甲基、三甲基硅基或苯基。Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.
- 根据权利要求1～5中任意一项所述的含氮化合物，其中，Ar1选自取代或未取代的基团V；Ar2选自氢、取代或未取代的基团V；其中，所述未取代的基团V选自如下基团：
The nitrogen-containing compound according to any one of claims 1 to 5, wherein Ar 1 is selected from a substituted or unsubstituted group V; Ar 2 is selected from hydrogen, a substituted or unsubstituted group V; wherein the unsubstituted group V is selected from the following groups:
取代的基团V中具有一个或两个以上取代基，取代基各自独立地选自氘、氟、氰基、三氘代甲基、三甲基硅基、三氟甲基、环戊基、环己基、金刚烷基、甲基、乙基、异丙基、叔丁基、苯基、萘基、吡啶基、二苯并呋喃基、二苯并噻吩基或咔唑基，且当基团V上的取代基个数大于1时，各取代基相同或不同。The substituted group V has one or more substituents, each of which is independently selected from deuterium, fluorine, cyano, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of substituents on the group V is greater than 1, each substituent is the same or different. - 根据权利要求1～6中任意一项所述的含氮化合物，其中，各R1、R2和R3相同或不同，且各自独立地选自氘、氰基、氟、三氘代甲基、三甲基硅基、三氟甲基、环戊基、环己基、金刚烷基、甲基、乙基、异丙基、叔丁基、苯基或萘基。The nitrogen-containing compound according to any one of claims 1 to 6, wherein each of R 1 , R 2 and R 3 is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
- 根据权利要求1～7中任意一项所述的含氮化合物，其中，选自以下基团构成的组，选自氢或以下基团：
The nitrogen-containing compound according to any one of claims 1 to 7, wherein Selected from the group consisting of the following groups, is selected from hydrogen or the following groups:
- 根据权利要求1～8中任意一项所述的含氮化合物，其中式1中选自以下基团构成的组：
The nitrogen-containing compound according to any one of claims 1 to 8, wherein in formula 1 Selected from the group consisting of:
- 根据权利要求1～9中任意一项所述的含氮化合物，其中，式1中选自以下基团构成的组：
The nitrogen-containing compound according to any one of claims 1 to 9, wherein in formula 1 Selected from the group consisting of:
- 根据权利要求1～10中任意一项所述的含氮化合物，其中，所述含氮化合物选自以下化合物所构成的组：
The nitrogen-containing compound according to any one of claims 1 to 10, wherein the nitrogen-containing compound is selected from the group consisting of the following compounds:
- 有机电致发光器件，包括相对设置的阳极和阴极，以及设于所述阳极和所述阴极之间的功能层；其特征在于，所述功能层包含权利要求1～11中任一项所述的含氮化合物；An organic electroluminescent device, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; characterized in that the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 11;可选地，所述功能层包括有机发光层，所述有机发光层包含所述含氮化合物。Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the nitrogen-containing compound.
- 电子装置，其特征在于，包括权利要求12所述的有机电致发光器件。 An electronic device, characterized by comprising the organic electroluminescent device according to claim 12.
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| CN113582997A (en) * | 2021-06-18 | 2021-11-02 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, electronic component, and electronic device |
| CN114105992A (en) * | 2021-06-18 | 2022-03-01 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, and organic electroluminescent device and electronic device comprising same |
| CN114456172A (en) * | 2021-10-28 | 2022-05-10 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, and electronic component and electronic device comprising same |
| CN114805179A (en) * | 2022-04-15 | 2022-07-29 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
| CN114920750A (en) * | 2022-05-27 | 2022-08-19 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
| WO2022250087A1 (en) * | 2021-05-25 | 2022-12-01 | 国立大学法人東海国立大学機構 | Organic scintillation material |
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| WO2022250087A1 (en) * | 2021-05-25 | 2022-12-01 | 国立大学法人東海国立大学機構 | Organic scintillation material |
| CN113582997A (en) * | 2021-06-18 | 2021-11-02 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, electronic component, and electronic device |
| CN114105992A (en) * | 2021-06-18 | 2022-03-01 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, and organic electroluminescent device and electronic device comprising same |
| CN114456172A (en) * | 2021-10-28 | 2022-05-10 | 陕西莱特迈思光电材料有限公司 | Nitrogen-containing compound, and electronic component and electronic device comprising same |
| CN114805179A (en) * | 2022-04-15 | 2022-07-29 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
| CN114920750A (en) * | 2022-05-27 | 2022-08-19 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
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