CN116969969A - Nitrogen-containing compound, organic electroluminescent device and electronic device - Google Patents
Nitrogen-containing compound, organic electroluminescent device and electronic device Download PDFInfo
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- CN116969969A CN116969969A CN202210527743.9A CN202210527743A CN116969969A CN 116969969 A CN116969969 A CN 116969969A CN 202210527743 A CN202210527743 A CN 202210527743A CN 116969969 A CN116969969 A CN 116969969A
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- substituted
- unsubstituted
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- carbon atoms
- nitrogen
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 87
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- 125000001424 substituent group Chemical group 0.000 claims description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 31
- 229910052805 deuterium Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 33
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002738 chelating agent 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
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000004440 column chromatography Methods 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
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 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
- 230000008020 evaporation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003709 fluoroalkyl 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
- 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
- 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
- 230000000155 isotopic effect Effects 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
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-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
- 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
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 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
- 125000003367 polycyclic group Chemical group 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 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
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 125000003003 spiro group Chemical group 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation 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
- 238000005406 washing Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The application relates to the technical field of organic electroluminescent materials, and provides a nitrogen-containing compound, an organic electroluminescent device and an electronic device containing the same. The nitrogen-containing compound disclosed by the application contains a mother nucleus structure of indole condensed phenothiazine/phenoxazine, and when the nitrogen-containing compound is used as a main material of a luminescent layer of an organic electroluminescent device, the luminous efficiency and the service life of the device can be obviously improved.
Description
Technical Field
The application relates to the technical field of organic electroluminescent materials, in particular to a nitrogen-containing compound, an organic electroluminescent device and an electronic device containing the same.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. An organic electroluminescent device (OLED) generally includes a cathode and an anode disposed opposite each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of a plurality of organic or inorganic film layers, and generally includes an organic light emitting layer, a hole transporting layer, an electron transporting layer, and the like. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards.
In the existing organic electroluminescent devices, the most important problems are represented by the service life and efficiency, and along with the large area of the display, the driving voltage is also improved, and the luminous efficiency and the current efficiency are also required to be improved, so that it is necessary to continuously develop novel materials to further improve the performance of the organic electroluminescent devices.
Disclosure of Invention
In view of the foregoing problems of the prior art, it is an object of the present application to provide a nitrogen-containing compound, which is used in an organic electroluminescent device and can improve the performance of the device, and an electronic element and an electronic device including the same.
According to a first aspect of the present application, there is provided a nitrogen-containing compound having a structure represented by formula 1:
wherein X is selected from S or O;
the group A is selected from a structure shown in a formula a-1 or a structure shown in a formula a-2;
HAr is selected from a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 40 carbon atoms;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;
the substituents in HAr are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms or aryl group having 6 to 20 carbon atoms;
L、L 1 、L 2 And L 3 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;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
Ar 3 selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
Ar 4 selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, or Ar 4 Is a single bond;
L、L 1 、L 2 、L 3 、Ar 1 、Ar 2 、Ar 3 and Ar is a group 4 The substituents of (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, phosphono having 6 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or aryloxy having 6 to 20 carbon atoms Arylthio of about 20; optionally Ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Any two adjacent substituents form a saturated or unsaturated 3-15 membered ring.
Each R is 1 、R 2 And R is 3 And are the same or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups of 1 to 10 carbon atoms, haloalkyl groups of 1 to 10 carbon atoms, deuterated alkyl groups of 1 to 10 carbon atoms, trialkylsilyl groups of 3 to 12 carbon atoms, aryl groups of 6 to 20 carbon atoms, heteroaryl groups of 3 to 20 carbon atoms or cycloalkyl groups of 3 to 10 carbon atoms, optionally any two adjacent groups forming a benzene ring;
n 1 represents R 1 Number n of (n) 1 Selected from 0, 1, 2, 3 or 4; n is n 2 Represents R 2 Number n of (n) 2 Selected from 0, 1, 2 or 3; n is n 3 Represents R 3 Number n of (n) 3 Selected from 0, 1, 2, 3 or 4.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the nitrogen-containing compound described above.
According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.
The compound disclosed by the application has a parent nucleus structure containing indole condensed phenothiazine/phenoxazine, and sulfur or oxygen atoms in the indole condensed phenothiazine/phenoxazine are provided with two pairs of lone pair electrons, so that excellent hole transport capacity can be provided for the parent nucleus structure. When the parent nucleus structure is connected with aryl or electron-rich heteroaryl, the hole transmission capacity of the compound can be enhanced, and the compound is suitable for P-type materials in a mixed main body material; when the parent nucleus structure is connected with the nitrogen-containing heteroarylene with the electron transmission property, the compound can have excellent hole transmission property and electron transmission property, and is suitable for a single main body material. When the compound is used as a P-type material and a single-type main body material in a mixed main body material, the carrier balance in a light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the light-emitting efficiency and the service life of a device can be improved.
Drawings
The accompanying drawings are included to provide a further understanding of the application, and are incorporated in and constitute a part of this specification, illustrate the application and together with the description serve to explain, without limitation, the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
321. First hole transport layer 322, second hole transport layer 330, organic light emitting layer 340, and electron transport layer
350. Electron injection layer 400 and electronic device
Detailed Description
Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the exemplary embodiments 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, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by formula 1:
wherein, is connected to->On any carbon or nitrogen atom;
x is selected from S or O;
the group A is selected from a structure shown in a formula a-1 or a structure shown in a formula a-2;
HAr is selected from a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 40 carbon atoms;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;
the substituents in HAr are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms or aryl group having 6 to 20 carbon atoms;
L、L 1 、L 2 and L 3 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;
A r1 and A r2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
A r3 selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
A r4 Selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, or Ar 4 Is a single bond;
when (when)Is connected to->Ar at the $locus on Zhong- $ 4 Is a single bond;
L、L 1 、L 2 、L 3 、Ar 1 、Ar 2 、Ar 3 and Ar is a group 4 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, phosphono having 6 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms. Optionally Ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Any two adjacent substituents form a saturated or unsaturated 3-15 membered ring;
each R is 1 、R 2 And R is 3 And are the same or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups of 1 to 10 carbon atoms, haloalkyl groups of 1 to 10 carbon atoms, deuterated alkyl groups of 1 to 10 carbon atoms, trialkylsilyl groups of 3 to 12 carbon atoms, aryl groups of 6 to 20 carbon atoms, heteroaryl groups of 3 to 20 carbon atoms or cycloalkyl groups of 3 to 10 carbon atoms, optionally any two adjacent groups forming a benzene ring;
n 1 Represents R 1 Number n of (n) 1 Selected from 0, 1, 2, 3 or 4; n is n 2 Represents R 2 Number n of (n) 2 Selected from 0, 1, 2 or 3; n is n 3 Represents R 3 Is set in the number of (3), n3 selected from 0, 1, 2, 3 or 4.
Optionally, any two adjacent R 1 Forming a benzene ring.
Optionally, any two adjacent R 2 Forming a benzene ring.
Optionally, any two adjacent R 3 Forming a benzene ring.
In the present disclosure, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance 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, i.e., include: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring. As another example, "optionally Ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Wherein any two adjacent substituents form a ring "means Ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Any two adjacent substituents of (a) are linked to form a ring, or Ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Any two adjacent substituents of (a) may be present independently of each other. Any two adjacent atoms can include two substituents on the same atom, and can also include two adjacent atoms with one substituent respectively; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated spiro ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring.
In the present application, the descriptions of "… …" and "… …" and "… …" are used independently and interchangeably, and should be understood in a broad sense, which may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed,wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituents R ' on the benzene ring, each R ' may be the same or different, and each R ' has the option ofThe two are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, cycloalkyl or the like. The number of substitutions may be 1 or more.
In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, etc.
The hydrogen atoms in the structures of the compounds of the present application include various isotopic atoms of the hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered as aryl groups of the present application unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. Aromatic hydrocarbon Examples of radicals may include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc.
In the present application, arylene refers to a divalent or polyvalent group formed by further loss of one or more hydrogen atoms from an aryl group.
In the present application, the terphenyl group includes
In the present application, the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group, for example, a substituted aryl group having 18 carbon atoms refers to the total number of carbon atoms of the aryl group and the substituents being 18.
In the present application, the substituted or unsubstituted aryl (arylene) group may have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 30, 31, 33, 34, 35, 36, 38, 40 or the like. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 40 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 25 carbon atoms, and in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms.
In the present application, the fluorenyl group may be substituted with 1 or more substituents. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be:and the like, but is not limited thereto.
In the application, as L, L 1 、L 2 、L 3 、Ar 1 、Ar 2 、Ar 3 And Ar is a group 4 For example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.
In the present application, heteroaryl means a monovalent aromatic ring containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring or derivatives thereof, which may be one or more of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto.
In the present application, the term "heteroarylene" refers to a divalent or polyvalent group formed by further losing one or more hydrogen atoms.
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) group may 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 substituted or unsubstituted heteroaryl having a total of from 3 to 40 carbon atoms, in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 3 to 30 carbon atoms, and in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 5 to 12 carbon atoms.
In the application, as L, L 1 、L 2 、L 3 、Ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Heteroaryl groups of substituents of (a) such as, but not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl, dibenzofuranyl.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, and the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
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 alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 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.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.
In the present application, specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In the present application, the cycloalkyl group having 3 to 10 carbon atoms may have 3, 4, 5, 6, 7, 8 or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
In the present application, a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms means a heteroarylene group having 3 to 20 carbon atoms and containing at least 1 nitrogen atom.
In the present application,"-," - $ "," - # "refer to chemical bonds that are interconnected with other groups, and the various labels on the bonds are merely to distinguish one from another.
In the present application, the connection key is not positioned in relation to a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
By an off-site substituent in the context of the present application is meant a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by the same includes any one of possible linkages as shown in the formulae (Y-1) to (Y-7).
In some embodiments, the compound of formula 1 is selected from the structures shown below:
in some embodiments, the compound of formula 1 is selected from the structures shown below:
in the compounds of the applicationWhen the group connection mode is shown as the formula 2-1 to 2-7, the stability of the parent nucleus is higher, the thermal stability of the molecule is improved, and the service life of the device can be prolonged when the compound is applied to the luminescent layer of the device.
In the present application, het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms. Preferably, at least two nitrogen atoms are contained in the Het group.
In some embodiments, het is selected from triazinylene, pyrimidinylene or pyridinyl.
In some embodiments, het is selected fromWherein, represents a bond to L, ->Representation and representationL 1 Or L 2 And a bond connected thereto.
In some embodiments of the application, het or HAr is an electron-deficient nitrogen-containing heteroaryl (also known as electron-deficient heteroaryl) comprising at least one nitrogen atom, sp 2 The hybrid nitrogen atom can reduce the electron cloud density of the conjugated system of the heteroaryl group as a whole rather than improve the electron cloud density of the conjugated system of the heteroaryl group, the lone pair electrons on the heteroatom do not participate in the conjugated system, and the heteroatom reduces the electron cloud density of the conjugated system due to stronger electronegativity. For example, electron-deficient nitrogen-containing heteroaryl groups may include, but are not limited to, triazinyl, pyrimidinyl, quinolinyl, quinoxalinyl, quinazolinyl, isoquinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, benzoquinazolinyl, phenanthroimidazolyl, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, and the like. The electron-deficient nitrogen-containing heteroaryl group can form an electron-transporting core group of the compound, so that the compound can effectively realize electron transport, and further can effectively balance the transport rate of electrons and holes in the organic light-emitting layer.
In other embodiments of the present application, HAr is an electron rich aromatic group that has a rich overall electron cloud density, and for example, electron rich aromatic groups may include, but are not limited to, phenylene, naphthylene, biphenylene, anthracenylene, phenanthrenylene, fluorenylene, dibenzothienyl, dibenzofuranylene, carbazolylene, triphenylene, pyrenylene, perylene, spirobifluorenylene, and the like. The electron-rich aromatic group can form a hole transport auxiliary group of the compound, so that the compound can effectively realize hole transport, and further can effectively balance the transport rate of electrons and holes in the organic light-emitting layer.
In some embodiments, HAr is selected from a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
Alternatively, the substituents in HAr are the same or different and are each independently selected from deuterium, cyano, halogen groups or alkyl groups of 1 to 4 carbon atoms, deuterated alkyl groups of 1 to 4 carbon atoms or aryl groups of 6 to 12 carbon atoms.
In some embodiments, HAr is selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolylene, or selected from the group consisting of substituted or unsubstituted:
the method comprises the steps of carrying out a first treatment on the surface of the - # represents a bond to L, - +.>Representation and L 3 A linked bond; each substituent in HAr is the same or different and is independently selected from deuterium, fluorine, cyano, tridentate methyl, trifluoromethyl, alkyl having 1 to 4 carbon atoms, or phenyl.
In some embodiments, HAr is selected from a substituted or unsubstituted group W selected from the group consisting of:
- # represents a bond to L,representation and L 3 A linked bond;
the substituted group W has one or more than two substituents, each substituent is independently selected from deuterium, fluorine, cyano, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl, and when the number of the substituents is more than 1, the substituents are the same or different.
In some embodiments, ar 1 And Ar is a group 2 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms.
In some embodiments, ar 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted aryl groups 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 groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
In some embodiments, ar 3 Selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms.
In some embodiments, ar 3 A substituted or unsubstituted aryl group selected from hydrogen, a substituted or unsubstituted aryl group 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 a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
In some embodiments, ar 4 Selected from single bond, substituted or unsubstituted aryl with 6-25 carbon atoms, and substituted or unsubstituted heteroaryl with 5-20 carbon atoms.
In some embodiments, ar 4 A substituted or unsubstituted aryl group selected from a single bond, a substituted or unsubstituted aryl group 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 a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
In some embodiments, ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Each substituent of (a) is independentlySelected from deuterium, halogen group, cyano, haloalkyl of 1 to 4 carbon atoms, deuterated alkyl of 1 to 4 carbon atoms, cycloalkyl of 5 to 10 carbon atoms, aryl of 6 to 12 carbon atoms, heteroaryl of 5 to 12 carbon atoms, trialkylsilyl of 3 to 8 carbon atoms, optionally any two adjacent substituents forming a benzene ring or fluorene ring.
In some embodiments, ar 1 And Ar is a group 2 And are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted pyridinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, and substituted or unsubstituted benzimidazolyl.
Alternatively, ar 1 And Ar is a group 2 Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, pyridinyl, dibenzofuranyl, dibenzothienyl or carbazolyl, optionally Ar 1 And Ar is a group 2 Any two adjacent substituents form a benzene ring.
In some embodiments, ar 1 And Ar is a group 2 Identical or different and are each independently selected from the following groups:
in some embodiments, ar 3 Selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted pyridinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted quinolinyl.
Alternatively, ar 3 Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, pyridinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, optionally Ar 3 Any two adjacent substituents form a benzene ring.
In some embodiments, ar 1 And Ar is a group 2 Each independently selected from the group consisting of substituted or unsubstituted groups W; ar (Ar) 3 A group W selected from hydrogen, substituted or unsubstituted; ar (Ar) 4 Is a single bond or is selected from a substituted or unsubstituted group W; wherein the unsubstituted group W is selected from the group consisting of:
the substituted group W has one or more than two substituents, the substituents of the substituted group W are each independently selected from deuterium, fluorine, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzoxazolyl or benzothiazolyl, and when the number of substituents on the group W is greater than 1, the substituents are the same or different.
In some embodiments, ar 3 Selected from the group consisting of hydrogen or:
in some embodiments, ar 4 Selected from the group consisting of a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.
Alternatively, ar 4 Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl or carbazolyl, optionally Ar 4 Any two adjacent substituents form a benzene ring.
In some embodiments, ar 4 Selected from the group consisting of single bonds or:
In some embodiments, L, L 1 、L 2 And L 3 And 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, a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.
Optionally L, L 1 、L 2 And L 3 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, deuteroalkyl having 1 to 4 carbon atoms, phenyl or naphthyl.
In some embodiments, L and L 3 And 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.
In some embodiments, L 1 And L 2 And are each independently selected from the group consisting of 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 fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group, and a substituted or unsubstituted pyridylene group.
Optionally L, L 3 、L 1 And L 2 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl or phenyl.
In some embodiments, L and L 3 Each independently selected fromA single bond or a group consisting of:
in some embodiments, L 1 And L 2 Each independently selected from the group consisting of a single bond or:
in some embodiments, each R 1 、R 2 And R is 3 Identical or different and are each independently selected from deuterium, cyano, fluoro, trimethylsilyl, tridentate methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, optionally any two adjacent groups forming a benzene ring.
In some embodiments, group a is selected from the group consisting of:
optionally, the nitrogen-containing compound is selected from the group consisting of the compounds shown below:
in a second aspect of the present application, there is provided 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 according to the first aspect of the present application.
The nitrogen-containing compound provided by the application can be used for forming at least one organic film layer in the functional layer so as to improve the luminous efficiency, the service life and other characteristics of the organic electroluminescent device.
Optionally, the functional layer includes an organic light emitting layer including the nitrogen-containing compound. The organic light-emitting layer may be composed of the nitrogen-containing compound provided by the present application, or may be composed of the nitrogen-containing compound provided by the present application together with other materials.
According to a specific embodiment, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport 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 sequentially stacked as shown in fig. 1.
In the present application, the anode 100 comprises an anode material, which is preferablyIs 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 alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene ](PEDT), polypyrrole, and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
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 multimers, carbazole-linked triarylamine compounds, or other types of compounds, and may specifically be selected from the compounds shown below or any combination thereof:
in one embodiment, the first hole transport layer 321 may be composed of α -NPD.
In one embodiment, second hole transport layer 322 is comprised of HT-1.
Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
in one embodiment, hole injection layer 310 is comprised of PD.
In the present application, the organic light emitting layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, 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 at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which 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 a metal chelating compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. Optionally, the host material comprises the nitrogen-containing compound of the present application.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application. Guest materials are also known as doping materials or dopants. Fluorescent dopants and phosphorescent dopants can be classified according to the type of luminescence. Specific examples of phosphorescent dopants include but are not limited to,
in one embodiment of the present application, the organic electroluminescent device is a red 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 may be Ir (Mphq) 3 。
In one of the present applicationIn an embodiment, 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 may be, for example, fac-Ir (ppy) 3 。
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, BTB, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application is not particularly limited by comparison. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:
in one embodiment of the present application, electron transport layer 340 may be composed of BTB and LiQ, or ET-2 and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material 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 a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
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 an inorganic material such as an alkali metal sulfide, an alkali metal halide, 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).
A third aspect of the application provides an electronic device comprising an organic electroluminescent device according to the second aspect of the application.
According to one embodiment, as shown in fig. 2, an electronic device 400 is provided, which includes the organic electroluminescent device described above. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The synthesis method of the nitrogen-containing compound of the present application is specifically described below with reference to synthesis examples, but the present disclosure is not limited thereto.
Synthetic examples
Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many of the organic compounds of the present application, and that other methods for preparing the compounds of the present application are considered to be within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the application can be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. All compounds of the synthesis process not mentioned in the present application are commercially available starting products.
Synthesis of Sub-a 1:
to a 500mL three-necked flask under nitrogen atmosphere, indole (5.85 g,50 mmol), 1-bromo-4-chloronaphthalene (13.20 g,55 mmol), cuprous iodide (0.19 g,1 mmol), phenanthroline (3.60 g,20 mmol), 18-crown-6 (1.32 g,5 mmol), anhydrous potassium carbonate (13.82 g,100 mmol) and DMF (150 mL) were added sequentially, stirring and heating were turned on, and the temperature was raised to reflux reaction for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane as the mobile phase afforded Sub-a1 (11.36 g, 82% yield) as a white solid.
Referring to the synthesis of Sub-a1, sub-a2 and Sub-a3 were synthesized using reactant A shown in Table 1 instead of 1-bromo-4-chloronaphthalene.
Table 1: synthesis of Sub-a2 and Sub-a3
Synthesis of Sub-b 1:
to a 250mL three-necked flask, the reaction mixture (CAS: 3377-71-7, 10.36g,50 mmol), 2-chlorocyclohexanone (6.60 g,50 mmol), anhydrous sodium carbonate (6.36 g,60 mmol) and 2, 2-trifluoroacetic acid (75 mL) were added under nitrogen atmosphere, and the mixture was stirred at room temperature for 48 hours. After the reaction is finished, the solvent is removed by reduced pressure distillation, and a crude product is obtained. Purification by silica gel column chromatography using n-heptane as the mobile phase afforded Sub-b1 (11.97 g, 79% yield) as a white solid.
Referring to the synthesis of Sub-a1, sub-B2 to Sub-B12 were synthesized using reactant B shown in Table 2 instead of CAS 3377-71-7.
Table 2: synthesis of Sub-b2 to Sub-b12
Synthesis of Sub-c 1:
sub-b8 (14.45 g,50 mmol), 2-amino-4-chlorophenylthiol (11.92 g,75 mmol), sodium periodate (2.16 g,10 mmol), DMSO (15.63 g,200 mmol) and 1, 4-dioxane (150 mL) were sequentially added to a 500mL three-necked flask under an air atmosphere, the mixture was heated to reflux and stirred for reaction for 12 hours; after the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/ethyl acetate as the mobile phase afforded Sub-c1 (8.71 g, 41% yield) as a white solid.
Referring to the synthesis of Sub-C1, sub-C2 to Sub-C14 were synthesized using reactant C shown in Table 3 instead of Sub-b8 and reactant D instead of 2-amino-4-chlorophenylthiol.
Table 3: synthesis of Sub-c2 to Sub-c14
Synthesis of Sub-d 1:
to a 500mL three-necked flask, sub-c1 (21.20 g,50 mmol), cuprous bromide (1.43 g,10 mmol) and DMF (220 mL) were added under air atmosphere, stirring and heating were turned on, and the temperature was raised to 100℃for reaction for 12h. After the system was cooled to room temperature, it was extracted with methylene chloride (150 mL. Times.3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/ethyl acetate as the mobile phase afforded Sub-d1 as a white solid (14.16 g, 67% yield).
Referring to the synthesis of Sub-d1, sub-d2 to Sub-d14 were synthesized using reactant E shown in Table 4 instead of Sub-c 1.
Table 4: synthesis of Sub-d2 to Sub-d14
Synthesis of Sub-e1
To a 500mL three-necked flask under nitrogen atmosphere, sub-d1 (21.10 g,50 mmol), 4-chlorobenzeneboronic acid (8.58 g,55 mmol), palladium acetate (0.22 g,1.0 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (X-Phos, 0.95g,2 mmol), anhydrous potassium carbonate (13.82 g,100 mmol), toluene (220 mL), tetrahydrofuran (55 mL) and deionized water (55 mL) were sequentially added, and stirring and heating were turned on, and the temperature was raised to reflux reaction for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane as the mobile phase afforded Sub-e1 as a white solid (18.18 g, 73% yield).
Referring to the synthesis of Sub-e1, sub-e2 was synthesized using reactant F shown in Table 5 instead of 4-chlorobenzoic acid.
Table 5: synthesis of Sub-e2
Synthesis of Sub-f 1:
sub-d4 (20.11 g,50 mmol), potassium tert-butoxide (56.10 g,500 mmol) and DMSO (300 mL) were added sequentially to a 500mL three-necked flask under nitrogen atmosphere, stirring and heating were turned on, and the temperature was raised to 50-60℃to react for 4 hours. After the system is cooled to room temperature, pouring the reaction solution into 500mL of deionized water, and precipitating out; suction filtration and filtration solid taking, filtration solid using dichloromethane (200 mL), after dissolution, adding anhydrous sodium sulfate for drying, filtration and filtrate taking, vacuum distillation to remove solvent, crude product is obtained. Purification by silica gel column chromatography using n-heptane/dichloromethane as the mobile phase afforded compound Sub-f1 (13.11 g, 84% yield) as a white solid.
Referring to the synthesis of Sub-f1, sub-f2 was synthesized using reactant G shown in Table 6 instead of Sub-d 4.
Table 6: synthesis of Sub-f2
Synthesis of Sub-g1
Sub-f2 (17.30 g,50 mmol), 1- (4-bromophenyl) naphthalene (15.51 g,55 mmol), tris (dibenzylideneacetone) dipalladium (Pd) were sequentially added to a 500mL three-necked flask under nitrogen atmosphere 2 (dba) 3 0.916g,1 mmol), XPhos (0.95 g,2 mmol), sodium t-butoxide (t-Buona, 9.61g,100 mmol) and toluene (180 mmol), warmed to reflux and stirred overnight; after the system is cooled to room temperature, pouring the reaction solution into 500mL of deionized water, fully stirring for 30min, carrying out suction filtration, leaching a filter cake to be neutral by using the deionized water, and leaching by using absolute ethyl alcohol (200 mL); n-heptane/dichloromethane as a mobile phase was purified by column chromatography on silica gel to give Sub-g1 (20.0 g, 73% yield) as a white solid.
Referring to the synthesis of Sub-g1, sub-g2 was synthesized using reactant H shown in Table 7 instead of Sub-f2 and reactant J instead of 1- (4-bromophenyl) naphthalene.
Table 7: synthesis of Sub-g2
Synthesis of Sub-h1
Sub-d5 (21.10 g,50 mmol), bisboronic acid pinacol ester (15.24 g,60 mmol), potassium acetate (9.81 g,100 mmol) and 1, 4-dioxane (220 mL) are added into a 500mL three-necked flask in sequence under nitrogen atmosphere, stirring and heating are started, pd is added rapidly when the temperature of the system is raised to 40 DEG C 2 (dba) 3 (0.46 g,0.5 mmol) and XPhos (0.48 g,1.0 mmol) were continued to warm to reflux and the reaction was stirred overnight. After the system is cooled to room temperature, 200mL of water is added into the system, the mixture is fully stirred for 30min, the pressure is reduced, the filtration cake is washed to be neutral by deionized water, and then 100mL of absolute ethyl alcohol is used for leaching, so that gray solid is obtained; the crude product was slurried once with n-heptane, dissolved in 200mL of toluene, passed through a silica gel column, the catalyst removed, and concentrated to give Sub-h1 (19.54 g, 76% yield) as a white solid.
Referring to the synthesis of Sub-h1, sub-h2 to Sub-h16 were synthesized using reactant K shown in Table 8 instead of Sub-d 5.
Table 8: synthesis of Sub-h2 to Sub-h16
Synthesis of Sub-j 1:
nitrogen atmosphereNext, 2- (4-biphenylyl) -4, 6-dichloro-1, 3, 5-triazine (22.66 g,75 mmol), 3-phenanthreneboronic acid (11.10 g,50 mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.58g,0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61g,5 mmol), anhydrous potassium carbonate (13.82 g,100 mmol), toluene (220 mL) and deionized water (55 mL), stirring and heating were turned on, and the temperature was raised to 65-70℃for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. The crude product was recrystallized from toluene to give Sub-j1 as a white solid (14.62 g, yield 66%).
Referring to the synthesis of Sub-j1, sub-j2 and Sub-j6 were synthesized using reactant L shown in Table 9 instead of 2- (4-biphenyl) -4, 6-dichloro-1, 3, 5-triazine, reactant M instead of 3-phenanthreneboronic acid.
Table 9: synthesis of Sub-j2 and Sub-j6
Synthesis of Compound 3:
to a 1000mL three-necked flask was added Sub-h1 (15.60 g,50 mmol), CAS:2737218-48-1 (27.10 g,75 mmol) and dried DMF (400 mL) in this order, the system was cooled to-10℃and sodium hydrogen (60% content, 2.2g,55 mmol) was added rapidly and the reaction stirred overnight. Pouring the reaction solution into 500mL of deionized water, fully stirring for 30min, carrying out suction filtration, washing the solid with deionized water to be neutral, and eluting with absolute ethyl alcohol (200 mL) to obtain a crude product; the crude product was recrystallized from toluene to give green solid compound 3 (24.85 g, 78% yield), mass spectrum m/z=638.2 [ m+h ]] + 。
Referring to the synthesis of compound 3, the compounds of the present application in Table 10 were synthesized using reactant N shown in Table 10 in place of CAS 2737218-48-1.
Table 10: synthesis of the Compounds of the application
Synthesis of Compound 80:
sub-f1 (18.51 g,36 mmol), CAS 2568464-79-7 (10.26 g,30 mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 0.42g,0.36 mmol), tetrabutylammonium bromide (TBAB, 1.16g,3.6 mmol), anhydrous potassium carbonate (9.95 g,72 mmol), toluene (180 mL), tetrahydrofuran (45 mL) and deionized water (45 mL), stirring and heating were turned on, and the temperature was raised to reflux for 12 hours. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Silica gel column chromatography purification of the crude product using n-heptane/dichloromethane as mobile phase afforded compound 80 (15.60 g, 75% yield) as a white solid, m/z=695.2 [ m+h ] ] + 。
Referring to the synthesis of compound 80, using reactant O shown in Table 11 in place of Sub-f1 and reactant P in place of CAS 2568464-79-7, the following inventive compounds were synthesized:
table 11: synthesis of the Compounds of the application
Synthesis of Compound 349:
sub-h1 (15.60 g,50 mmol), CAS 1852465-55-4 (20.4 g,60 mmol), anhydrous potassium carbonate (6.91 g,50 mmol), toluene (180 mL), dimethylaminopyridine (3.05 g,25 mmol) and N, N-dimethylacetamide (160 mL) were added sequentially to a 500mL three-necked flask under nitrogen atmosphere, stirring and heating were turned on, and the temperature was raised to 220℃for reflux reaction for 12 hours. After the system was cooled to room temperature, it was extracted with ethyl acetate (100 mL. Times.3 times), and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. Purification by silica gel column chromatography using n-heptane/ethyl acetate as the mobile phase afforded compound 349 (16.33 g, 53% yield, m/z=617.2 [ m+h)] + 。
Referring to the synthesis of compound 349, the following inventive compound was synthesized using reactant P shown in Table 12 in place of CAS 1852465-55-4:
table 12
Synthesis of Compound 803:
sub-h1 (7.81 g,25 mmol), CAS 1419864-64-4 (11.61 g,27.5 mmol), tris (dibenzylideneacetone) dipalladium (Pd) were added sequentially to a 250mL three-necked flask under nitrogen atmosphere 2 (dba) 3 0.46g,0.5 mmol), (2-dicyclohexylphosphine-2 ',4',6' triisopropylbiphenyl) (X-Phos, 0.48g,1 mmol), sodium tert-butoxide (t-Buona, 4.8g,50 mmol) and xylene (xylene, 120 mL), warmed to reflux, and stirred overnight; after the system is cooled to room temperature, pouring the reaction solution into 500mL of deionized water, fully stirring for 30min, carrying out suction filtration, leaching a filter cake to be neutral by using deionized water, and leaching the filter cake by using absolute ethyl alcohol (200 mL) to obtain a crude product; purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded a white solid (12.10 g; yield 74%).
Referring to the synthesis of compound 803, the following inventive compound was synthesized using reactant Q shown in Table 13 in place of CAS 1419864-64-4:
TABLE 13
Compound 7 nuclear magnetism: 1 H-NMR(400MHz,CD 2 Cl 2 )δppm 8.55-8.50(m,4H),8.14(d,1H),8.08(d,2H),7.98(d,1H),7.90(d,1H),7.86(d,1H),7.81-7.78(m,2H),7.73(d,1H),7.64(d,1H),7.58(t,1H),7.54-7.47(m,3H),7.42(t,2H),7.36(d,1H),7.24(t,1H),7.19-7.15(m,2H),7.10(d,1H),7.02(t,1H),6.82(d,1H).
compound 730 nuclear magnetism: 1 H-NMR(400MHz,CD 2 Cl 2 )δppm 8.16(d,2H),8.02(d,1H),7.90(d,1H),7.74(d,1H),7.66-7.62(m,2H),7.59-7.50(m,6H),7.44(d,1H),7.39-7.31(m,4H),7.24(t,1H),7.18-7.08(m,5H),7.02(t,1H),6.82(d,1H).
organic electroluminescent device preparation and evaluation:
example 1: preparation of red organic electroluminescent device
The anode pretreatment is carried out by the following steps: in the thickness of in turnThe ITO/Ag/ITO substrate is subjected to surface treatment by utilizing ultraviolet ozone and O2: N2 plasma to increase the work function of an anode, and the surface of the ITO substrate is cleaned by adopting an organic solvent to remove impurities and greasy dirt on the surface of the ITO substrate.
Vacuum evaporating PD on an experimental substrate (anode) to form a film with a thickness ofIs then vacuum evaporated on the hole injection layer to form an alpha-NPD of +.>Is provided.
Vacuum evaporating compound HT-1 on the first hole transport layer to form a film having a thickness ofIs provided.
Next, on the second hole transport layer, compound 3:Ir (Mphq) 3 Co-evaporation is carried out at an evaporation rate ratio of 98 percent to 2 percent to form the film with the thickness ofRed light organic light emitting layer (EML).
On the organic light-emitting layer, the compound BTB and LiQ are mixed in a weight ratio of 1:1 and evaporated to formThick Electron Transport Layer (ETL) with Yb vapor deposited on the electron transport layer to formThickness of->Then magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer to form a film having a thickness +.>Is provided.
Further, CP-1 is vacuum deposited on the cathode to form a cathode having a thickness ofAnd thus the red organic electroluminescent device is manufactured.
Examples 2 to 43
An organic electroluminescent device was prepared by the same method as in example 1, except that the remaining compounds in table 14 below were used in place of the compound 3 in example 1, respectively, at the time of preparing an organic light emitting layer.
Comparative examples 1 to 3
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 in place of compound 3 in example 1, respectively, when the organic luminescent layer was prepared.
In each of the examples and comparative examples, the main materials used had the following structures:
performance test was performed on the red organic electroluminescent devices prepared in examples 1 to 43 and comparative examples 1 to 3, specifically at 10mA/cm 2 IVL performance of the device was tested under the conditions of T95 device lifetime at 20mA/cm 2 The test was conducted under the conditions of (2) and the test results are shown in Table 14.
TABLE 14
As is clear from Table 14, when the compound of the present application is used as a host material for an organic electroluminescent device, the efficiency of the device is improved by at least 10.8% and the lifetime is improved by at least 11.1% while maintaining a low operating voltage, as compared with comparative examples 1 to 3.
Example 44: red organic electroluminescent device
The anode pretreatment is carried out by the following steps: in the thickness of in turnThe ITO/Ag/ITO substrate is subjected to surface treatment by utilizing ultraviolet ozone and O2: N2 plasma to increase the work function of an anode, and the surface of the ITO substrate is cleaned by adopting an organic solvent to remove impurities and greasy dirt on the surface of the ITO substrate.
Vacuum evaporating PD on an experimental substrate (anode) to form a film with a thickness ofIs then vacuum evaporated on the hole injection layer to form a-NPD with a thickness +.>Is provided.
Vacuum evaporating compound HT-1 on the first hole transport layer to form a film having a thickness ofIs provided.
ThenOn the second hole transport layer, RH-N: compound 660:Ir (Mphq) 3 49%: the vapor deposition rate ratio of 49 percent to 2 percent is used for co-vapor deposition to form the film with the thickness ofRed light emitting layer (EML).
On the light-emitting layer, the compounds BTB and LiQ are mixed and evaporated in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Then magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer to form a film having a thickness +.>Is provided.
In addition, the thickness of the vacuum evaporation on the cathode isTo complete the manufacture of the red organic electroluminescent device.
Examples 45 to 56
An organic electroluminescent device was prepared by the same method as in example 44, except that the compound 660 in example 44 was replaced with the compound in table 15 below at the time of preparing an organic luminescent layer.
Comparative examples 4 to 5
An organic electroluminescent device was fabricated by the same method as in example 44, except that compound D and compound E were used instead of compound 660 in example 44 when the organic luminescent layer was fabricated.
Among these, the main materials used in examples 44 to 56 and comparative examples 4 to 5 had the following structures:
performance test was performed on the red organic electroluminescent devices prepared in examples 44 to 56 and comparative examples 4 and 5, specifically at 10mA/cm 2 IVL performance of the device was tested under the conditions of T95 device lifetime at 20mA/cm 2 The test was conducted under the conditions of (2) and the test results are shown in Table 15.
TABLE 15
Referring to table 15 above, it can be seen that when the compound of the present application is used as a P-type host in a premix-type host material for a red organic electroluminescent device, the luminous efficiency of the device is improved by at least 13.1% and the lifetime is improved by at least 16% while maintaining a low operating voltage.
The compound disclosed by the application has a parent nucleus structure containing indole condensed phenothiazine/phenoxazine, and sulfur or oxygen atoms in the indole condensed phenothiazine/phenoxazine are provided with two pairs of lone pair electrons, so that excellent hole transport capacity can be provided for the parent nucleus structure. When the parent nucleus structure is connected with aryl or electron-rich heteroaryl, the hole transmission capacity of the compound can be enhanced, and the compound is suitable for P-type materials in a mixed main body material; when the parent nucleus structure is connected with the nitrogen-containing heteroarylene with the electron transmission property, the compound can have excellent hole transmission property and electron transmission property, and is suitable for a single main body material. When the compound is used as a P-type material and a single-type main body material in a mixed main body material, the carrier balance in a light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the light-emitting efficiency and the service life of a device can be improved.
Claims (15)
1. A nitrogen-containing compound, characterized in that the nitrogen-containing compound has a structure represented by formula 1:
wherein X is selected from S or O;
the group A is selected from a structure shown in a formula a-1 or a structure shown in a formula a-2;
HAr is selected from a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 40 carbon atoms;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;
the substituents in HAr are the same or different and are each independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms or aryl group having 6 to 20 carbon atoms;
L、L 1 、L 2 and L 3 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;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
Ar 3 selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
Ar 4 selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, or Ar 4 Is a single bond;
L、L 1 、L 2 、L 3 、Ar 1 、Ar 2 、Ar 3 and Ar is a group 4 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, phosphono having 6 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms. Optionally Ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Any two adjacent substituents form a saturated or unsaturated 3-15 membered ring;
each R is 1 、R 2 And R is 3 And are the same or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups of 1 to 10 carbon atoms, haloalkyl groups of 1 to 10 carbon atoms, deuterated alkyl groups of 1 to 10 carbon atoms, trialkylsilyl groups of 3 to 12 carbon atoms, aryl groups of 6 to 20 carbon atoms, heteroaryl groups of 3 to 20 carbon atoms or cycloalkyl groups of 3 to 10 carbon atoms, optionally any two adjacent groups forming a benzene ring;
n 1 Represents R 1 Number n of (n) 1 Selected from 0, 1, 2, 3 or 4; n is n 2 Represents R 2 Number n of (n) 2 Selected from 0, 1, 2 or 3; n is n 3 Represents R 3 Number n of (n) 3 Selected from 0, 1, 2, 3 or 4.
2. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound represented by formula 1 is selected from the structures represented by:
3. the nitrogen-containing compound according to claim 1, wherein Het is selected from triazinylene, pyrimidinylene or pyridinyl;
alternatively Het is selected fromWherein, represents a bond to L, ->Representation and L 1 Or L 2 And a bond connected thereto.
4. The nitrogen-containing compound according to claim 1, wherein HAr is selected from 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 phenanthrylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolylene group, or a substituted or unsubstituted group selected from the following:
- # represents a bond to L,representation and L 3 A linked bond; each substituent in HAr is the same or different and is independently selected from deuterium, fluorine, cyano, tridentate methyl, trifluoromethyl, alkyl having 1 to 4 carbon atoms, or phenyl.
5. The nitrogen-containing compound according to claim 1, wherein HAr is selected from a substituted or unsubstituted group W selected from the group consisting of:
- # represents a bond to L,representation and L 3 A linked bond;
the substituted group W has one or more than two substituents, each substituent is independently selected from deuterium, fluorine, cyano, tridentate methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl, and when the number of the substituents is more than 1, the substituents are the same or different.
6. The nitrogen-containing compound according to claim 1, wherein Ar 1 And Ar is a group 2 The same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms;
alternatively, ar 3 Selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5 to 20 carbon atoms;
alternatively, ar 4 Selected from single bond, substituted or unsubstituted aryl with 6-25 carbon atoms, substituted or unsubstituted heteroaryl with 5-20 carbon atoms;
alternatively, ar 1 、Ar 2 、Ar 3 And Ar is a group 4 Each of the substituents is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuteroalkyl group having 1 to 4 carbon atoms, an 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, a trialkylsilyl group having 3 to 8 carbon atoms, optionally any two adjacent substituents forming a benzene ring or a fluorene ring.
7. The nitrogen-containing compound according to claim 1, wherein Ar 1 And Ar is a group 2 And are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted pyridinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, and substituted or unsubstituted benzimidazolyl.
Alternatively, ar 1 And Ar is a group 2 Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, pyridinyl, dibenzofuranyl, dibenzothienyl or carbazolyl, optionally Ar 1 And Ar is a group 2 Any two adjacent substituents form a benzene ring.
8. The nitrogen-containing compound according to claim 1, wherein Ar 3 Selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted pyridinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted quinolinyl;
alternatively, ar 3 Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl or pyridinyl, optionally Ar 3 Any two adjacent substituents form a benzene ring.
9. The nitrogen-containing compound according to claim 1, wherein Ar 4 Selected from the group consisting of a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group;
alternatively, ar 4 Each substituent of (a) is independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, dibenzothienyl, dibenzofuranyl or carbazolyl, optionally Ar 4 Any two adjacent substituents form a benzene ring.
10. The nitrogen-containing compound according to claim 1, wherein L and L 3 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;
Alternatively, L 1 And L 2 And are each independently selected from the group consisting of 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 fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzoylene groupThienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridylene;
optionally L, L 3 、L 1 And L 2 Each substituent of (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl or phenyl.
11. The nitrogen-containing compound according to claim 1, wherein each R 1 、R 2 And R is 3 Identical or different and are each independently selected from deuterium, cyano, fluoro, trimethylsilyl, tridentate methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl, optionally any two adjacent groups forming a benzene ring.
12. The nitrogen-containing compound according to claim 1, wherein the group a is selected from the group consisting of:
13. the nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
14. The organic electroluminescent device comprises an anode and a cathode which are oppositely arranged, 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 13;
optionally, the functional layer includes an organic light emitting layer, the organic light emitting layer including the nitrogen-containing compound.
15. Electronic device, characterized in that it comprises an organic electroluminescent device as claimed in claim 13 or 14.
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| PCT/CN2023/076795 WO2023197744A1 (en) | 2022-04-15 | 2023-02-17 | Nitrogen-containing compound, organic electroluminescent device and electronic apparatus |
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| CN116396292A (en) * | 2023-04-04 | 2023-07-07 | 武汉天马微电子有限公司 | Organic compound and application thereof |
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| CN116396292A (en) * | 2023-04-04 | 2023-07-07 | 武汉天马微电子有限公司 | Organic compound and application thereof |
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