CN114149443B - Nitrogen-containing compound, electronic component and electronic device - Google Patents
Nitrogen-containing compound, electronic component and electronic device Download PDFInfo
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- CN114149443B CN114149443B CN202011306341.3A CN202011306341A CN114149443B CN 114149443 B CN114149443 B CN 114149443B CN 202011306341 A CN202011306341 A CN 202011306341A CN 114149443 B CN114149443 B CN 114149443B
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- carbon atoms
- nitrogen
- containing compound
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 69
- 239000000463 material Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 118
- 239000010410 layer Substances 0.000 claims description 118
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000002346 layers by function Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 59
- 125000003118 aryl group Chemical group 0.000 description 52
- 150000001875 compounds Chemical class 0.000 description 42
- 125000001072 heteroaryl group Chemical group 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 230000005525 hole transport Effects 0.000 description 25
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000010408 film Substances 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- 125000004665 trialkylsilyl group Chemical group 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 11
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 125000001188 haloalkyl group Chemical group 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 150000002431 hydrogen Chemical group 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- LLKRSJVPTKFSLS-UHFFFAOYSA-N 2-bromo-5-iodopyridine Chemical compound BrC1=CC=C(I)C=N1 LLKRSJVPTKFSLS-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- BQHRJUASXACWDG-UHFFFAOYSA-N ClN1NC(=CC(=N1)Cl)C1=CC=CC=C1 Chemical compound ClN1NC(=CC(=N1)Cl)C1=CC=CC=C1 BQHRJUASXACWDG-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
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- 125000002541 furyl group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 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 2
- 238000000746 purification Methods 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
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- 239000000741 silica gel Substances 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 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
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 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
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- MIUMTDPSDBCACC-UHFFFAOYSA-N copper zinc Chemical compound [Cu][Zn][Cu] MIUMTDPSDBCACC-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 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
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Chemical group C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 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
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 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
- 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
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 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
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 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
- 238000010248 power generation Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 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
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
The application relates to the technical field of organic electroluminescent materials, and provides a nitrogen-containing compound, an electronic element and an electronic device. The structure of the nitrogen-containing compound is shown as formula 1, wherein X 1 And X 2 Each independently selected from O or S; r is R 1 And R is 2 Each independently selected from hydrogen or a structure represented by formula 2, and R 1 And R is 2 Only one of them has the structure shown in formula 2. The nitrogen-containing compound can improve the performance of electronic components.
Description
Technical Field
The present disclosure relates to the technical field of organic electroluminescent materials, and in particular, to a nitrogen-containing compound, an electronic device including the same, and an electronic device including the same.
Background
An organic electroluminescent device belongs to an electronic component, such as an Organic Light Emitting Diode (OLED), and generally includes a cathode and an anode disposed opposite to 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 order to improve the brightness, efficiency and lifetime of organic electroluminescent devices, multilayer structures are commonly used in organic electroluminescent devices, which may include one or more of the following film layers: a hole injection layer (hole injection layer, HIL), a hole transport layer (hole transport layer, HTL), an electron-blocking layer (EBL), an organic electroluminescent layer (EML), a Hole Blocking Layer (HBL), an electron transport layer (electron transport layer, ETL), an electron injection layer (electron injection layer, EIL), and the like. The film layers can improve the injection efficiency of carriers (holes and electrons) between interfaces of all layers and balance the transmission capacity of carriers between all layers, thereby improving the brightness and efficiency of the organic electroluminescent device.
In the conventional organic electroluminescent devices, the life and efficiency are the major problems, and as the display is increased in area, the driving voltage is increased, so that the luminous efficiency and the current efficiency are also improved, and thus, new materials are required to be continuously developed to further improve the performance of the organic electroluminescent devices.
Disclosure of Invention
The present application aims to provide a nitrogen-containing compound, an electronic component and an electronic device, which are capable of improving the performance of the electronic component.
According to a first aspect of the present application, there is provided a nitrogen-containing compound having a structure as shown in formula 1:
wherein X is 1 And X 2 The same or different and are each independently selected from O or S;
R 1 and R is 2 Each independently selected from hydrogen or a structure represented by formula 2, and R 1 And R is 2 Only one of which is of the structure shown in formula 2;
Y 1 ～Y 5 identical or different, each independently selected from C (R a )、C(R b ) Or N atom, and Y 1 ～Y 5 Two adjacent atoms are not N atoms at the same time, Y 1 ～Y 5 Wherein 1, 2 or 3 are N atoms, and only one is C (R b ) The balance being C (R a )；
R a Selected from hydrogen, carbonA substituted or unsubstituted aryl group having 6 to 30 atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
R b is that
Ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms; l is selected from single bond, substituted or unsubstituted arylene with 6-15 carbon atoms, and substituted or unsubstituted heteroarylene with 5-15 carbon atoms;
R a and Ar are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms; and at R a And Ar, optionally, any adjacent two substituents form a ring;
the substituent in L is selected from deuterium, halogen group, cyano, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms and trialkylsilyl with 3-7 carbon atoms.
According to a second aspect of the present application, there is provided an electronic component comprising an anode and a cathode arranged opposite each other, and a functional layer provided 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 electronic element described above.
The nitrogen-containing compound provided by the application comprises a diheteroaromatic ring and benzimidazole group (mother nucleus), wherein hetero atoms in the diheteroaromatic ring are O or S atoms, lone pair electrons on O and S can improve the electron cloud density of the benzimidazole ring, improve the highest occupied orbit (HOMO) energy level of the corresponding compound, reduce the lowest unoccupied orbit (LUMO) energy level, and simultaneously enhance the hole transmission capability and electron transmission capability of the compound.The nitrogen-containing compound of the present application is suitable as a host material or an electron transport layer material of a light-emitting layer in an electronic element (such as an organic electroluminescent device), a linking group (R 1 And R is 2 One of them) is a nitrogen-containing heterocycle having an electron transporting property, and can enhance the electron transporting ability of the target compound. When the linking group is attached to the parent nucleus with sp 2 When hybridized on a benzene ring having carbon atoms attached thereto, i.e. R 2 When the target compound is a nitrogen-containing heterocycle, the target compound has a lower LUMO energy level, so that when the target compound is used as an electron transport layer material, electrons can be accelerated to be transported into a light-emitting layer, a composite region of holes and electrons is widened, and the service life of a device is prolonged. In addition, when the linking group is attached to the parent nucleus with sp 3 When hybridized on benzene rings to which nitrogen atoms are attached, i.e. R 1 In the case of a nitrogen-containing heterocycle, the first excited singlet state of the target compound (S 1 ) Energy level and first excited triplet state (T 1 ) Small energy level difference<0.5 eV), the compound is used as a main material of a luminescent layer, so that the working voltage of the device can be obviously reduced, and the service life of the device can be prolonged.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
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 a first electronic device according to an embodiment of the present application.
Fig. 3 is a schematic structural view of a photoelectric conversion device according to an embodiment of the present application.
Fig. 4 is a schematic structural diagram of a second electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic electroluminescent layer; 340. an electron transport layer; 350. an electron injection layer; 360. a photoelectric conversion layer; 400. a first electronic device; 500. and a second electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many different 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 example 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 present application.
In order to achieve the above object, a first aspect of the present application provides a nitrogen-containing compound having a structure shown in formula 1:
Wherein X is 1 And X 2 The same or different and are each independently selected from O or S;
R 1 and R is 2 Selected from hydrogen or a structure represented by formula 2, and R 1 And R is 2 Only one of which is of the structure shown in formula 2;
Y 1 ～Y 5 identical or different, each independently selected from C (R a )、C(R b ) Or N atom, and Y 1 ～Y 5 Two adjacent ones of the two are not N, Y at the same time 1 ～Y 5 Wherein 1, 2 or 3 are N atoms, and only one is C (R b ) The balance being C (R a )；
R a Selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms;
R b is that
Ar is selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms; l is selected from single bond, substituted or unsubstituted arylene with 6-15 carbon atoms, and substituted or unsubstituted heteroarylene with 5-15 carbon atoms;
R a and Ar are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms; at R a And Ar, optionally, any adjacent two substituents form a ring;
the substituent in L is selected from deuterium, halogen group, cyano, alkyl with 1-4 carbon atoms, haloalkyl with 1-4 carbon atoms and trialkylsilyl with 3-7 carbon atoms.
In this application, the descriptions used herein of the manner in which each … … is independently "and" … … is independently "and" … … is independently selected from "are interchangeable, and should be understood in a broad sense to mean that the specific options expressed between the same symbols in different groups do not affect each other, or that the 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 substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' 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, the substituent is collectively referred to as Rs). For example, "substituted or unsubstituted aryl" refers to aryl or unsubstituted aryl having a substituent Rs. Wherein the above substituents, i.e., rs, may be, for example, deuterium, halogen group, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, cycloalkyl, alkoxy, etc.; when two substituents Rs are attached to the same atom, the two substituents Rs may be present independently or attached to each other to form a ring with the atom to which they are commonly attached; when two adjacent substituent Rs are present on a functional group, the adjacent two substituent Rs may be present independently or fused to the functional group to which they are attached to form a ring.
In the present application, the number of carbon atoms of a substituted or unsubstituted group refers to all the numbers of carbon atoms. For example, if Ar is selected from substituted phenyl groups having 12 carbon atoms, then the phenyl groups and all of the carbon atoms of the substituents thereon are 12.
In this 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 aryl groups herein 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. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, benzo [9,10 ] ]Phenanthryl, pyrenyl, benzofluoranthenyl,
A base, etc.
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as a deuterium atom, a halogen group, a cyano group, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, or the like. Specific examples of heteroaryl substituted aryl groups include, but are not limited to, dibenzofuranyl substituted phenyl, dibenzothiophene substituted phenyl, pyridine substituted phenyl, carbazolyl substituted phenyl, and the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18.
In this application, fluorenyl groups may be substituted and two substituents may combine with each other to form a spiro structure, specific examples include, but are not limited to, the following structures:
in the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof containing at least one heteroatom in the ring, which may be at least one 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, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-arylcarbazolyl and N-heteroarylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds.
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, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothienyl, phenyl-substituted pyridyl, 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 expression "any two adjacent substituents form a ring", and "any two adjacent" may include two substituents on the same atom, and may include two adjacent atoms each having one substituent; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated ring (e.g., a 5-18 membered saturated or unsaturated 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, non-positional connection means a single bond extending from a ring system
It 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 phenanthryl group represented by the formula (X') is linked to the other position of the molecule through an unoriented linkage extending from the middle of one benzene ring, and the meaning of the linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
An delocalized substituent in this application refers to 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 the present application, the alkyl group having 1 to 10 carbon atoms may include a straight chain alkyl group having 1 to 10 carbon atoms and a branched chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl and the like.
In the present application, halogen groups may include fluorine, bromine, chlorine, iodine, and the like.
In the present application, the aryl group having 6 to 20 carbon atoms as a substituent may have 6, 10, 12, 14, 18, 20 or the like carbon atoms, for example. Specific examples of aryl groups as substituents include, but are not limited to, phenyl, naphthyl, biphenyl, anthracenyl, phenanthryl, and the like.
In the present application, the heteroaryl group having 3 to 18 carbon atoms as a substituent may have 3, 4, 5, 7, 8, 9, 12, 18 or the like carbon atoms, for example. Specific examples of heteroaryl groups as substituents include, but are not limited to, pyridyl, quinolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, and the like.
In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.
Specific examples of cycloalkyl groups having 3 to 10 carbon atoms in the present application include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present application, it should be understood that in formula 2, Y 1 ～Y 5 At least one of them is selected from C (R a ) When each C (R a ) May be the same or different. For example, Y 1 、Y 2 Each independently is C (R) a ) When Y is 1 、Y 2 The specific structure of (2) may be the same or different, e.g. Y 1 Can be CH, Y 2 May be C (Ph).
Alternatively, R 1 And R is 2 And only one (i.e., formula 2) is selected from the group consisting of structures represented by formulas 2-1 to 2-4:
alternatively, R a Selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms.
Alternatively, R a The substituents in (a) are selected fromFrom deuterium, fluorine, cyano, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms.
Alternatively, R a Specific examples of substituents in (a) include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, trimethylsilyl, trifluoromethyl, methoxy, methylthio, phenyl, naphthyl.
Alternatively, R 1 And R is 2 And only one (i.e., formula 2) is selected from the group consisting of:
at R b Optionally, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroarylene group having 8 to 12 carbon atoms.
Alternatively, the substituents in L are selected from methyl, t-butyl, trimethylsilyl or trifluoromethyl.
Alternatively, L may be selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group.
Optionally, L is selected from the group consisting of a single bond or:
at R b Optionally, ar is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 8 to 20 carbon atoms. For example, ar is selected from substituted or unsubstituted C6, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 24, 25 Or a substituted or unsubstituted heteroaryl group selected from the group consisting of 8, 9, 12, 16, 18, 20 carbon atoms.
Alternatively, the substituents in Ar are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, haloalkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 10 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms. Optionally, any two adjacent substituents form a ring.
Alternatively, specific examples of substituents of Ar include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, trimethylsilyl, trifluoromethyl, methoxy, methylthio, phenyl, naphthyl, pyridyl and the like.
Alternatively, R b The number of carbon atoms (i.e., the total number of carbon atoms of Ar and L) is 6 to 25.
In some embodiments, ar and R a Identical or different, and are each independently selected from the group consisting of groups of formulae i-1 to i-16:
wherein M is 1 Selected from single bonds or
G 1 ～G 5 Each independently selected from N or C (F) 1 ) And G 1 ～G 5 At least one of which is selected from N; when G 1 ～G 5 More than two of them are selected from C (F 1 ) At any two times F 1 The same or different;
G 6 ～G 13 each independently selected from N or C (F) 2 ) And G 6 ～G 13 At least one of which is selected from N; when G 6 ～G 13 More than two of them are selected from C (F 2 ) At any two times F 2 The same or different;
G 14 ～G 23 each independently selected from N or C (F) 3 ) And G 14 ～G 23 At least one of which is selected from N; when G 14 ～G 23 More than two of them are selected from C (F 3 ) At any two times F 3 The same or different;
G 24 ～G 33 each independently selected from N or C (F) 4 ) And G 24 ～G 33 At least one of which is selected from N; when G 24 ～G 33 More than two of them are selected from C (F 4 ) At any two times F 4 The same or different;
E 1 selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms;
E 2 ～E 9 、E 20 each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, heteroaryl having 3 to 18 carbon atoms;
E 10 ～E 19 、F 1 ～F 4 Each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms;
e 1 ～e 20 e is as follows k Representation, E 1 ～E 20 By E k K represents a variable, an arbitrary integer of 1 to 20, e k Representation fetchSubstituent E k Is the number of (3); wherein when k is selected from 5 or 17, e k Selected from 1, 2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 20, e k Selected from 1, 2, 3 or 4; when k is selected from 1, 3, 4, 6, 9 or 14, e k Selected from 1, 2, 3, 4 or 5; when k is 13, e k Selected from 1, 2, 3, 4, 5 or 6; when k is selected from 10 or 19, e k Selected from 1, 2, 3, 4, 5, 6 or 7; when k is 11, e k Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; and when e k When greater than 1, any two E k The same or different;
K 1 selected from O, S, N (E) 22 )、C(E 23 E 24 )、Si(E 23 E 24 ) The method comprises the steps of carrying out a first treatment on the surface of the Wherein E is 22 、E 23 、E 24 Each independently selected from: aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms, alkyl having 1 to 10 carbon atoms or cycloalkyl having 3 to 10 carbon atoms, or E 23 And E is 24 To each other to form a ring with the atoms to which they are commonly attached;
K 2 selected from single bonds, O, S, N (E) 25 )、C(E 26 E 27 )、Si(E 26 E 27 ) The method comprises the steps of carrying out a first treatment on the surface of the Wherein E is 25 、E 26 、E 27 Each independently selected from: aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms, alkyl having 1 to 10 carbon atoms or cycloalkyl having 3 to 10 carbon atoms, or E 26 And E is 27 To form a ring with the atoms to which they are commonly attached.
Alternatively, ar and R a Each independently selected from the group consisting of substituted or unsubstituted groups Z selected from the group consisting of:
the substituted group Z has one or more than two substituents, and each substituent is independently selected from deuterium, cyano, fluorine, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, alkoxy with 1-4 carbon atoms, alkylthio with 1-4 carbon atoms, trialkylsilicon with 3-7 carbon atoms, pyridyl and phenyl; when the number of substituents is two or more, any two substituents may be the same or different.
Optionally, ar is selected from the group consisting of:
in some embodiments, R b May be selected from the group consisting of:
alternatively, R a Selected from hydrogen or from the group consisting of:
According to one embodiment, R 1 And R is 2 One and only one of them is
Wherein R is a Selected from substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, or substituted or unsubstituted heteroaryl groups having 8 to 15 carbon atoms.
According to one embodiment, in formula 1, X 1 And X 2 Simultaneously O or simultaneously S.
In the application, the structure of the nitrogen-containing compound is shown as a formula 1-1 or a formula 1-2:
specifically, the nitrogen-containing compound is selected from the group consisting of the following structures:
preferably, the nitrogen-containing compound is selected from the group consisting of structures represented by formulas 1-1-1, 1-2-1, 1-1-2, and 1-2-2.
Optionally, the nitrogen-containing compound is selected from the group consisting of the compounds recited in claim 10, i.e., the nitrogen-containing compound is selected from the group consisting of compounds 1 to 1546.
The synthesis method of the provided nitrogen-containing compound is not particularly limited in this application, and a person skilled in the art can determine a suitable synthesis method from the preparation method provided in the synthesis example section in combination with the nitrogen-containing compound of this application. In other words, the synthesis examples section of the present invention illustratively provides a process for the preparation of nitrogen-containing compounds, using starting materials which are commercially available or are well known in the art. All of the nitrogen-containing compounds provided herein may be obtained by one skilled in the art from these exemplary methods of preparation, and all specific methods of preparation for such nitrogen-containing compounds are not described in detail herein and should not be construed as limiting the present application.
A second aspect of the present application provides an electronic component including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises a nitrogen-containing compound as described in 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 performance of the electronic element.
Optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device.
Optionally, the functional layer includes an electron transport layer that includes the nitrogen-containing compound, for example, a nitrogen-containing compound represented by formula 1-1.
Optionally, the functional layer includes a light-emitting layer, and the light-emitting layer includes a light-emitting host material and a doping material, wherein the light-emitting host material includes the nitrogen-containing compound, for example, includes the nitrogen-containing compound represented by formula 1-2.
According to one embodiment, the electronic component is an organic electroluminescent device. The organic electroluminescent device may be a blue, green or red organic electroluminescent device.
As shown in fig. 1, the organic electroluminescent device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 comprises a nitrogen-containing compound provided herein.
Optionally, functional layer 300 includes an electron transport layer 340, electron transport layer 340 comprising a nitrogen-containing compound as provided herein. The electron transport layer 340 may be composed of a nitrogen-containing compound provided herein, or may be composed of a nitrogen-containing compound provided herein and other materials. Optionally, the electron transport layer 340 further includes LiQ.
Alternatively, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic electroluminescent layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Further alternatively, the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322 that are stacked, and the first hole transport layer 321 is closer to the surface of the anode than the second hole transport layer 322. The second hole transport layer 322 is also referred to as an electron blocking layer.
Alternatively, the anode 100 includes an anode material, preferably a material having 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, copperZinc, 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, snO 2 Sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline, but not limited thereto. Preferably, the anode material comprises Indium Tin Oxide (ITO).
Alternatively, the first hole transport layer 321 may include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. For example, the first hole transport layer 321 is composed of the compound TPD.
Optionally, second hole transport layer 322 includes one or more electron blocking materials, which may be selected from carbazole multimers or other types of compounds, as not particularly limited herein. For example, the second hole transport layer 322 is composed of the compound TCTA.
Alternatively, the organic electroluminescent layer 330 may be composed of a single light emitting material, and may also include a light emitting host material and a guest material. Alternatively, the organic electroluminescent layer 330 is composed of a light emitting host material and a guest material (i.e., dopant), and holes and electrons injected into the organic luminescent layer may be recombined in the organic luminescent layer 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.
According to a specific embodiment, the light-emitting host material of the organic electroluminescent layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. For example, the host material of the organic electroluminescent layer 330 may be CBP.
According to another specific embodiment, the light-emitting host material of the organic electroluminescent layer 330 is a nitrogen-containing compound provided herein. Preferably, the organic electroluminescent device is a green organic electroluminescent device.
Alternatively, the guest material of the light emitting layer is 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 this application. For example, the guest material of the light emitting layer may be Ir (piq) 2 (acac) or BD-1 (structure shown in the following examples).
Alternatively, the cathode 200 comprises a cathode material, which is preferably a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include: 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 /Ca, but is not limited thereto. A metal electrode containing silver and magnesium is preferably included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed 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 a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. For example, hole injection layer 310 may be composed of HAT-CN.
Optionally, as shown in fig. 1, an electron injection layer 350 may also be 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. For example, the electron injection layer 350 may include ytterbium (Yb).
According to another embodiment, the electronic component may be a photoelectric conversion device, which may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200, as shown in fig. 3; the functional layer 300 comprises a nitrogen-containing compound provided herein.
Alternatively, as shown in fig. 3, the photoelectric conversion device may include an anode 100, a hole transport layer 320, a photoelectric conversion layer 360 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Optionally, the electron transport layer 340 comprises a nitrogen-containing compound of the present application to effectively improve the performance of the photoelectric conversion device.
Alternatively, the photoelectric conversion device may be a solar cell, in particular, an organic thin film solar cell. For example, as shown in fig. 3, the solar cell includes an anode 100, a hole transport layer 320, a photoelectric conversion layer 360, an electron transport layer 340 and a cathode 200, which are sequentially stacked, wherein the electron transport layer 340 contains a nitrogen-containing compound.
A third aspect of the present application provides an electronic device comprising an electronic component according to the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device described above. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting device, an optical module, etc.
According to another embodiment, as shown in fig. 4, the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device. The second electronic device 500 may be, for example, a solar power generation device, a light detector, a fingerprint identification device, a light module, a CCD camera, or other type of electronic device.
The present application will be described in detail below in connection with examples, but the following description is intended to explain the present application and is not intended to limit the scope of the present application in any way.
Synthetic examples
1. Synthesis of intermediate a-I
In this application, intermediate a-I includes intermediate a-1 through intermediate a-10.
1) Synthesis of intermediate a-1
To a 1000mL three-necked flask, reactant 1 (28.226 g,100 mmol), aniline (13.969 g,150 mmol), 4-bromobenzaldehyde (18.502 g,100 mmol), ammonium acetate (38.541 g,500 mmol) and glacial acetic acid (288 mL) were sequentially added, and the mixture was heated to reflux under nitrogen protection and stirred for reaction for 24 hours; cooling to room temperature, stopping stirring, pouring the reaction solution into 1000mL of water, and precipitating a large amount of gray solid; suction filtering, and washing the filter cake to neutrality by water; dissolving the filter cake with dichloromethane, and then adding anhydrous magnesium sulfate for drying; filtering, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using n-heptane/dichloromethane (v/v=1:1) as mobile relative crude product finally afforded intermediate a-1 (37.06 g, 70% yield) as a white solid.
2) Synthesis of intermediate a-2 to intermediate a-10
The procedure for the synthesis of intermediate a-2 through intermediate a-10 was referred to as intermediate a-1, except that reactant a was used in place of reactant 1, reactant B was used in place of aniline, and reactant C was used in place of 4-bromobenzaldehyde, and the main raw materials employed and the corresponding synthesized intermediates and yields are shown in table 1.
TABLE 1
Note that: reactant A can be referred to in the prior art as Chen, wangqiao; tan, si Yu; zhao, yanli; zhang, qichun, organic Chemistry Frontiers (2014), 1 (4), 391-394.
2. Synthesis of intermediate b-I
Intermediate b-I includes intermediate b-1 through intermediate b-10.
1) Synthesis of intermediate b-1
To a 500mL three-necked flask was added intermediate a-1 (37.06 g,70 mmol) and pre-dried tetrahydrofuran (370 mL); under the protection of nitrogen, cooling to-78 ℃, dropwise adding n-butyllithium solution (2.0M n-hexane solution, 38.5mL,77 mmol) under the stirring condition, and preserving heat (-78 ℃) after dropwise adding, and stirring for 1 hour; maintaining-78deg.C, adding dropwise B (OCH) 3 ) 3 (10.91 g,105 mmol), after the dripping is finished, preserving the temperature (-78 ℃) for 1 hour, and naturally heating the system to room temperature; to the reaction solution was added dropwise a solution of hydrochloric acid (12M) (8.8 mL,105.6 mmol) in water (50 mL), followed by stirring for 30 minutes; separating, taking an organic phase, washing the organic phase with water to be neutral, adding anhydrous magnesium sulfate for drying, and distilling under reduced pressure to remove a solvent to obtain a crude product; the crude product was slurried with 100mL of n-heptane and filtered to give intermediate b-1 (20.76 g, 60%) as a white solid.
2) Synthesis of intermediates b-2 to b-10
The intermediate b-2 to the intermediate b-10 were synthesized by referring to the method of the intermediate b-1, except that each intermediate a-I in table 2 was used instead of the intermediate a-1, and the intermediate b-2 to the intermediate b-10 were synthesized using the main raw materials and the corresponding synthesized intermediates and yields as shown in table 2.
TABLE 2
3. Synthesis of intermediate c-I
Intermediate c-I includes intermediate c-1 through intermediate c-43.
1) Synthesis of intermediate c-1
To a 500mL three-necked flask was added 2-bromo-5-iodopyridine (28.39 g,100 mmol), 3-biphenylboronic acid (19.80 g,100 mmol), tetrabutylammonium bromide (3.22 g,10 mmol), anhydrous potassium carbonate (27.64 g,200 mmol), toluene (280 mL) and deionized water (70 mL) in sequence; stirring is started, and heating is started after nitrogen is fully replaced; when the system was warmed to 40 ℃, tetrakis (triphenylphosphine) palladium (1.16 g,1 mmol) was added rapidly, and the temperature was continued to be raised to reflux, and the reaction was stirred for 24 hours. After the system was naturally cooled to room temperature, the reaction solution was poured into 250mL of water and extracted with methylene chloride (100 mL. Times.3); the organic phases are combined and dried by anhydrous magnesium sulfate, and the solvent is removed by reduced pressure distillation to obtain crude products; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as a mobile phase to give intermediate c-1 (24.82 g, 80%) as a white solid.
2) Synthesis of intermediates c-2 to c-43
The intermediates of Table 3 were synthesized with reference to the procedure for intermediate c-1, except that reactant D was used in place of 2-bromo-5-iodopyridine and reactant E was used in place of 3-biphenylboronic acid, and intermediates c-2 through c-43 were synthesized using similar procedures as described above, with the main starting materials employed and the corresponding synthesized intermediates and yields shown in Table 3.
TABLE 3 Table 3
Note that: reactant E is commercially available or can be obtained by reacting its bromo with n-butyllithium and trimethyl borate sequentially, see methods for synthesis of intermediates B-I.
4. Synthesis of intermediate e-I
Intermediate e-I includes intermediate e-1 through intermediate e-28.
1) Synthesis of intermediate e-1
To a 2000mL three-necked flask was added 1-adamantanol (110 g, 720 mmol), bromobenzene (113.45 g, 720 mmol) and 1100mL dichloromethane; under the protection of nitrogen, the system is cooled to-10 ℃, trifluoromethanesulfonic acid (162.65 g,1083 mmol) is added dropwise, the dropping speed is controlled, the dropping is completed within 30min, and the temperature is kept between 0 ℃ and 10 ℃ for 3.5 hours; the reaction was quenched by the addition of 250mL of water. Separating, namely taking an organic phase, and fully washing the organic phase with 1000mL of water until the water phase is neutral; the organic phase is added with anhydrous magnesium sulfate for drying, and the solvent is removed by pressure distillation to obtain crude products; purification of the crude product by silica gel chromatography using n-heptane as mobile phase yielded intermediate d-1 (100 g, 47.6%) as a white solid.
To a 2000mL three-necked flask was added intermediate d-1 (58.24 g,100 mmol) and pre-dried tetrahydrofuran (880 mL); under the protection of nitrogen, cooling to-78 ℃, dropwise adding n-butyllithium solution (2.0M n-hexane solution, 120mL,240 mmol) under the stirring condition, and preserving heat (-78 ℃) after dropwise adding, and stirring for 1 hour; maintaining-78deg.C, adding dropwise B (OCH) 3 ) 3 (31.17 g,300 mmol), after the dripping is completed, preserving the temperature (-78 ℃) for 1 hour, and naturally heating the system to room temperature; to the reaction solution was added dropwise a solution of hydrochloric acid (12M) (30 mL,360 mmol) in water (150 mL), followed by stirring for 30 minutes; separating, taking an organic phase, washing the organic phase with water to be neutral, adding anhydrous magnesium sulfate for drying, and distilling under reduced pressure to remove a solvent to obtain a crude product; the crude product was slurried with 100mL of n-heptane and filtered to give intermediate d-2 (30.66 g, 59.84%) as a white solid.
To a 500mL three-necked flask was added 2, 4-dichloro-6-phenyltriazine (18.134 g,80.22 mmol), intermediate d-2 (18.68 g,72.93 mmol), tetrabutylammonium bromide (2.35 g,8.02 mmol), anhydrous potassium carbonate (20.26 g,160.44 mmol), toluene (180 mL) and deionized water (45 mL) in this order; stirring is started, and heating is started after nitrogen is fully replaced; when the system was warmed to 40 ℃, tetrakis (triphenylphosphine) palladium (0.842 g,0.8 mmol) was rapidly added, and the temperature was further raised to 70 ℃ and the reaction was stirred for 24 hours. After the system was naturally cooled to room temperature, the reaction solution was poured into 250mL of water and extracted with methylene chloride (100 mL. Times.3); the organic phases are combined and dried by anhydrous magnesium sulfate, and the solvent is removed by reduced pressure distillation to obtain crude products; the crude product was purified by column chromatography on silica gel using methylene chloride/n-heptane as mobile phase to give intermediate e-1 (24.91 g, 85%) as a white solid.
In Table 4 below, reactant G replaces 2, 4-dichloro-6-phenyltriazine and reactant H replaces intermediate d-2, intermediates e-2 through e-30 were synthesized using a similar procedure as described above.
TABLE 4 Table 4
5) Synthesis of Compounds
To a 500mL three-necked flask, intermediate b-1 (20.76 g,42 mmol), intermediate c-1 (14.22 g,46.2 mmol), tetrabutylammonium bromide (1.35 g,4.2 mmol), anhydrous potassium carbonate (11.61 g,84 mmol), toluene (200 mL), anhydrous ethanol (25 mL), deionized water (25 mL) were sequentially added; stirring is started, and heating is started after nitrogen is fully replaced; when the system was warmed to 40 ℃, tetrakis (triphenylphosphine) palladium (0.4815 g,0.42 mmol) was added rapidly, and the temperature was continued to be raised to reflux, and the reaction was stirred for 24 hours. After the system was naturally cooled to room temperature, the reaction solution was poured into 250mL of water and extracted with methylene chloride (100 mL. Times.3); the organic phases are combined and dried by anhydrous magnesium sulfate, and the solvent is removed by reduced pressure distillation to obtain crude products; the crude product was purified by silica gel column chromatography using methylene chloride/n-heptane as a mobile phase to give compound 5 (23.42 g, 82%) as a white solid.
The compounds listed in Table 5 were synthesized by referring to the procedure for Compound 5, except that intermediate b-1 was replaced with reactant I (intermediate b-I), intermediate c-1 was replaced with reactant J (intermediate c-I, intermediate e-I), and the main raw materials used and the yields of the compounds are shown in Table 5.
TABLE 5
Wherein, the NMR data of a part of the compounds are as follows:
the compound (21) is a compound having the formula, 1 H NMR(400MHz,CDCl 3 ):δppm 8.49(s,1H),8.39-8.22(m,5H),8.15(d,2H),8.09(d,1H),7.99(d,1H),7.94(t,1H),7.86(d,1H),7.62-7.43(m,14H),7.33(t,1H)。
the compound 561 is a compound of formula 561, 1 H NMR(400MHz,CDCl 3 ):δppm 8.95(t,1H),8.82(d,2H),8.76(d,1H),8.59(d,1H),8.49(d,1H),8.43-8.37(m,2H),8.21(d,1H),8.13(d,1H),8.04(d,1H),7.74-7.57(m,11H),7.54-7.42(m,6H),7.33(t,1H)。
the compound 1023 is used as a carrier, 1 H NMR(400MHz,CDCl 3 ):δppm 8.82(d,2H),8.51-8.47(m,2H),8.39-8.34(m,2H),8.27-8.22(m,3H),8.13(d,1H),8.01(s,1H),7.77-7.56(m,12H),7.53-7.42(m,5H),7.15(d,1H)。
the compound of formula 1491, 1 H NMR(400MHz,CDCl 3 ):δppm 9.35(s,2H),8.49(d,1H),8.38(d,1H),8.27-8.22(m,3H),8.13(d,1H),7.94(s,1H),7.91(s,1H),7.77-7.72(m,2H),7.69-7.41(m,17H),7.32(d,1H),7.17(d,2H)。
the analysis of the compounds in the above synthesis examples and mass spectrum data are shown in Table 6.
TABLE 6
Blue organic electroluminescent device fabrication and evaluation
Example 1
An organic electroluminescent device was prepared by the following procedure:
the ITO thickness is equal to
Is cut into a size of 40mm by 0.7 (T) mm, and is prepared into an experimental substrate having a cathode bonding region, an anode and an insulating layer pattern by a photolithography process, and is irradiated with ultraviolet ozone and O 2 :N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.
Vacuum vapor deposition of HAT-CN on experimental substrate (anode) to form a thickness of
Is then vacuum deposited with NPB to form a layer of thickness +.>
A Hole Transport Layer (HTL).
Then evaporating a TCTA layer on the hole transport layer to form a layer with a thickness of
Electron Blocking Layer (EBL).
The alpha, beta-ADN is taken as a main body, the BD-1 is doped at the same time, and the thickness of the main body and the dopant is formed at the film thickness ratio of 30:3
As a light emitting layer (EML) of an organic electroluminescent device.
Simultaneously evaporating the compound 5 and LiQ on the light-emitting layer at a film thickness ratio of 1:1 to form
A thick Electron Transport Layer (ETL), followed by Mg: liF in accordance withCo-steaming was performed at a film thickness ratio of 1:1 to form a film having 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, a layer with the thickness of
And forming a capping layer (CPL), thereby completing the manufacture of the organic light emitting device.
Wherein, the structural formulas of HAT-CN, NPB, TCTA, alpha, beta-ADN, BD-1, liQ and CP-1 are as follows:
examples 2 to 46
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound shown in table 7 was used instead of the compound 5 in forming an Electron Transport Layer (ETL).
Comparative examples 1 to 3
Comparative examples 1 to 3 use Compound A, compound B and Alq, respectively 3 Instead of the compound 5, an organic electroluminescent device was fabricated in the same manner as in example 1.
Wherein, the structural formulas of the compound A, the compound B and the Alq3 are as follows:
the properties of the organic electroluminescent devices prepared are shown in Table 7, in which IVL data are compared at 10mA/cm 2 As a result of the test, the lifetime was 15mA/cm 2 Test results at current density.
TABLE 7
As can be seen from the results of Table 7, examples 1 to 46 prepared using the compounds of the present application have substantially equivalent operating voltages and luminous efficiencies (Cd/A) as compared with comparative examples 1 to 3, but have improved device lifetimes by at least 11.1%.
Preparation and evaluation of green organic electroluminescent device
Example 47
The green organic electroluminescent device was prepared by the following procedure: the ITO thickness is equal to
Is cut into a size of 40mm by 0.7 (T) mm, and is prepared into an experimental substrate having a cathode bonding region, an anode and an insulating layer pattern by a photolithography process, and is irradiated with ultraviolet ozone and O 2 :N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.
Vacuum vapor deposition of HAT-CN on experimental substrate (anode) to form a thickness of
Is then vacuum evaporated on the Hole Injection Layer (HIL)A layer of NPB to form a thickness of +.>
Is provided.
Vacuum evaporating HT-02 on the first hole transport layer to obtain a film with a thickness of
Is provided. />
Then, on the second hole transport layer, compound 990 (host) and Ir (ppy) 2 Co-evaporation of the acac (dopant) at a ratio of 90% to 10% to form a thickness of
Green light emitting layer (EML).
Then mixing ET-1 and LiQ in a weight ratio of 1:1 and evaporating to form
A thick Electron Transport Layer (ETL), followed by co-evaporation of Mg: liF at a film thickness ratio of 1:1 to form a film having 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, a layer with the thickness of
And forming a capping layer (CPL), thereby completing the manufacture of the green organic electroluminescent device.
Wherein HAT-CN, NPB, HT-02, ir (ppy) 2 The structural formulas of acac, ET-1, liQ and CP-1 are as follows:
examples 48 to 74
An organic electroluminescent device was fabricated by the same method as in example 47, except that the compound shown in table 8 was used instead of the host material compound 990 in example 47 when forming the light emitting layer (EML).
Comparative examples 4 to 6
Comparative examples 4 to 6 an organic electroluminescent device was fabricated in the same manner as in example 47 using compound C, compound D and compound E instead of compound 990, respectively.
Wherein, the structural formulas of the compound C, the compound D and the compound E are as follows:
the green organic electroluminescent devices prepared in examples 47 to 74 and comparative examples 4 to 6 were subjected to performance test, particularly 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 performed under the conditions of (2) and the test results are shown in Table 8.
TABLE 8
As can be seen from the results of Table 8, examples 47 to 74, which were prepared using the compounds of the present application as green host materials, exhibited at least 0.38V decrease in operating voltage, and substantially equivalent luminous efficiency (Cd/A), but improved device lifetime by at least 7.4% as compared with comparative examples 4 to 6.
Thus, the organic electroluminescent devices prepared in examples 1 to 74 have a longer lifetime than the comparative examples.
In summary, the organic compound of the present application has a specific structure, so that the organic compound has a certain advantage in the light-emitting layer or the electron-transporting layer of the organic electroluminescent device, compared with the previous materials, and has excellent electron-transporting performance, which contributes to the life extension of the organic electroluminescent device. The reason for this is that the nitrogen-containing compound of the present invention employed in the examples contains a diheteroaromatic-ring benzimidazole group in which the hetero atom in the diheteroaromatic ring is an O atom or S atom, and the lone pair electrons on the O atom and S atom can increase the electron cloud density of the benzimidazole ring, increase the highest occupied orbital (HOMO) energy level of the corresponding compound, decrease the lowest unoccupied orbital (LUMO) energy level, and enhance the hole transporting ability and electron transporting ability of the compound.
The above embodiments are only for illustrating the technical solution of the present invention, and are not limiting. Although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. A nitrogen-containing compound, characterized in that the structure of the nitrogen-containing compound is shown in formula 1:
wherein X is 1 And X 2 Identical, selected from O or S;
R 1 and R is 2 Selected from hydrogen or a structure represented by formula 2, and R 1 And R is 2 Only one of which is of the structure shown in formula 2;
Y 1 ～Y 5 identical or different, each independently selected from C (R a )、C(R b ) Or N atom, and Y 1 ～Y 5 Two adjacent ones of the two are not N, Y at the same time 1 ～Y 5 Wherein 1, 2 or 3 are N atoms, and only one is C (R b ) The balance being C (R a )；
R a Selected from hydrogen or a substituted or unsubstituted group Z;
R b is that
Ar is selected from a substituted or unsubstituted group Z;
wherein the unsubstituted group Z is selected from the group consisting of:
the substituted group Z has one or more than two substituents, and each substituent is independently selected from deuterium, cyano, fluorine, alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, trialkylsilicon group with 3-7 carbon atoms and phenyl; when the number of substituents is two or more, any two substituents are the same or different;
L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorenylene group;
the substituent in L is selected from methyl, tertiary butyl, trimethylsilyl or trifluoromethyl.
2. The nitrogen-containing compound according to claim 1, wherein R 1 And R is 2 And only one selected from the group consisting of:
3. the nitrogen-containing compound according to claim 1, wherein Ar is selected from the group consisting of:
4. the nitrogen-containing compound according to claim 1, wherein R a Selected from hydrogen or from the group consisting of:
5. the nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
6. an electronic component, characterized by comprising an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 5.
7. The electronic component according to claim 6, wherein the electronic component is an organic electroluminescent device or a photoelectric conversion device.
8. The electronic component according to claim 6 or 7, wherein the functional layer includes an electron transport layer containing the nitrogen-containing compound.
9. The electronic component according to claim 6, wherein the electronic component is an organic electroluminescent device, the functional layer includes a light-emitting layer, the light-emitting layer includes a light-emitting host material and a guest material, and the light-emitting host material includes the nitrogen-containing compound.
10. An electronic device comprising the electronic component of any one of claims 6-9.
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