CN117069701A - Nitrogen-containing compound, organic electroluminescent device and electronic device - Google Patents
Nitrogen-containing compound, organic electroluminescent device and electronic device Download PDFInfo
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- CN117069701A CN117069701A CN202211361357.3A CN202211361357A CN117069701A CN 117069701 A CN117069701 A CN 117069701A CN 202211361357 A CN202211361357 A CN 202211361357A CN 117069701 A CN117069701 A CN 117069701A
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- Prior art keywords
- carbon atoms
- group
- substituted
- unsubstituted
- nitrogen
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 135
- 239000010410 layer Substances 0.000 claims description 79
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 239000002346 layers by function Substances 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 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 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000005345 deuteroalkyl group Chemical group 0.000 claims description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 3
- 125000005577 anthracene group Chemical group 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 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 description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005581 pyrene group Chemical group 0.000 claims description 2
- 125000005566 carbazolylene group Chemical group 0.000 claims 1
- 238000005401 electroluminescence Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 37
- 239000000463 material Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 125000000524 functional group Chemical group 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
- 238000003756 stirring Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000010549 co-Evaporation Methods 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229940093956 potassium carbonate Drugs 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 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 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 compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012634 fragment Substances 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
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000001931 aliphatic group Chemical group 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
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 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
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=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
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002738 chelating agent 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
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 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
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 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
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The application belongs to the technical field of organic electroluminescence, and relates to a nitrogen-containing compound, an organic electroluminescent device and an electronic device using the same, wherein the nitrogen-containing compound has a structure shown as a formula 1, and the nitrogen-containing compound is used for the organic electroluminescent deviceIn the organic electroluminescent device, the performance of the organic electroluminescent device can be improved.
Description
Technical Field
The application relates to the technical field of organic electroluminescent materials, in particular to a nitrogen-containing compound, an organic electroluminescent device and an electronic device.
Background
Organic electroluminescent devices, such as Organic Light Emitting Diodes (OLEDs), typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of organic or inorganic film layers, and generally includes an organic light emitting layer, a hole transporting layer, an electron transporting layer, and the like. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards.
In the existing organic electroluminescent devices, the life and efficiency are the most important problems, and with the large area of the display, the driving voltage is also improved, and the luminous efficiency and the current efficiency are also improved.
Disclosure of Invention
The application aims to provide a nitrogen-containing compound, an organic electroluminescent device and an electronic device, so as to improve the performance of the organic electroluminescent device.
In order to achieve the above object, according to a first aspect of the present application, there is provided a nitrogen-containing compound having a structure represented by formula I:
in formula 1, ring A and ring B are each independently selected from aromatic rings having 6 to 16 carbon atoms;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;
L、L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
L、L 1 、L 2 、Ar 1 And Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, phosphono having 6 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms. Optionally Ar 1 、Ar 2 Any two adjacent substituents form a saturated or unsaturated 3-15 membered ring;
each R is 1 、R 2 、R 3 And R is 4 The two groups are identical or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, halogenated alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilicon groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms or cycloalkyl groups with 3 to 10 carbon atoms;
n 1 represents R 1 Number n of (n) 2 Represents R 2 Number n of (n) 1 And n 2 Each independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.
The application provides a method for preparing a compound which takes carbazole and derivatives thereof as main groups, and is characterized in that tetrahydronaphthalene is connected to the 9 # position of the carbazole and derivatives thereof, so that the twistability of the compound is improved, the intermolecular accumulation is reduced, and the crystallization is avoided. The heteroaryl fragment shows strong luminescence property due to the flatness and rigidity, and the thermal stability and electron affinity of the material are obviously improved. The compound has a relatively three-dimensional structure, can improve the performance of devices and improve the efficiency of the devices. The stable film forming property can improve the service life to a certain extent.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the nitrogen-containing compound described above.
According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device described above.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application, in which 100 denotes an anode, 200 denotes a cathode, 300 denotes a functional layer, 310 denotes a hole injection layer, 321 denotes a first hole transport layer, 322 denotes a second hole transport layer, 330 denotes an organic light emitting layer, 340 denotes an electron transport layer, and 350 denotes an electron injection layer.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the application.
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 application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals in the drawings denote the same or similar structures, and thus detailed descriptions thereof will be omitted.
In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by formula 1:
in formula 1, ring A and ring B are each independently selected from aromatic rings having 6 to 16 carbon atoms;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;
L、L 1 and L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 And Ar is a group 2 The same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
L、L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, phosphono having 6 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms. Optionally Ar 1 、Ar 2 Any two adjacent substituents form a saturated or unsaturated 3-15 membered ring;
each R is 1 、R 2 、R 3 And R is 4 The two groups are identical or different and are each independently selected from deuterium, cyano, halogen groups, alkyl groups with 1 to 10 carbon atoms, halogenated alkyl groups with 1 to 10 carbon atoms, deuterated alkyl groups with 1 to 10 carbon atoms, trialkylsilicon groups with 3 to 12 carbon atoms, aryl groups with 6 to 20 carbon atoms, heteroaryl groups with 3 to 20 carbon atoms or cycloalkyl groups with 3 to 10 carbon atoms;
n 1 Represents R 1 Number n of (n) 2 Represents R 2 Number n of (n) 1 And n 2 Each independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.
The application provides a method for preparing a compound which takes carbazole and derivatives thereof as main groups, and is characterized in that tetrahydronaphthalene is connected to the 9 # position of the carbazole and derivatives thereof, so that the twistability of the compound is improved, the intermolecular accumulation is reduced, and the crystallization is avoided. The heteroaryl fragment shows strong luminescence property due to the flatness and rigidity, and the thermal stability and electron affinity of the material are obviously improved. The compound has a relatively three-dimensional structure, can improve the performance of devices and improve the efficiency of the devices. The stable film forming property can improve the service life to a certain extent.
In the present application, the description modes "each … … is independently selected from" and "… … is independently selected from" and "… … is independently selected from" which are interchangeable, and should be understood in a broad sense, which may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed,wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q 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, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, heteroaryl, aryl, trialkylsilyl, triphenylsilyl, alkyl, haloalkyl, cycloalkyl, deuterated phenyl, or the like. The number of substitutions may be 1 or more.
In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the sum of all carbon atoms of the functional group and all substituents thereon.
In the present application, L 1 、L 2 、L、R 1 、R 2 、R 3 、R 4 、Ar 1 And Ar is a group 2 The number of carbon atoms in (a) refers to all the number of carbon atoms in the group. For example, if Ar 1 Selected from substituted aryl groups having 10 carbon atoms, then the aryl group and all of the substituents thereon have 10 carbon atoms. For another example, if Ar 1 Is 9, 9-dimethylfluorenyl, ar 1 Ar is substituted fluorenyl with 15 carbon atoms 1 The number of ring-forming carbon atoms is 13.
In the present application, "hetero" means that at least 1 hetero atom such as B, N, O, S, si, se or P is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise. Unsubstituted alkyl groups may be "saturated alkyl groups" without any double or triple bonds.
"Ring" in the present application includes saturated rings and unsaturated rings; saturated rings are saturated aliphatic rings, unsaturated rings are partially unsaturated rings, such as cyclohexene or aromatic rings, such as aromatic and heteroaromatic rings.
In the present application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6 membered ring. Saturated or unsaturated 3-15 membered ring means a cyclic group having 3 to 15 ring atoms. Examples of the 3-to 15-membered ring include cyclopentane, cyclohexane, fluorene ring, and benzene ring.
The hydrogen atoms in the structures of the compounds of the present application include various isotopic atoms of the hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).
In the present application, 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, or a cyclic aryl group Two or more monocyclic aryl groups linked by carbon-carbon bond conjugation, a monocyclic aryl group and a condensed ring aryl group linked by carbon-carbon bond conjugation, two or more condensed ring aryl groups linked by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered as aryl groups of the present application unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc.
In the present application, arylene groups are defined as divalent groups formed by further loss of one or more hydrogen atoms from an aryl group.
In the present application, the terphenyl group includes
In the present application, the substituted or unsubstituted aryl (arylene) group may have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 25 carbon atoms, in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 18 carbon atoms, and in other embodiments the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having from 6 to 15 carbon atoms.
In the present application, the fluorenyl group may be substituted with 1 or more substituents, and in the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be:and the like, but is not limited thereto.
In the present application, heteroaryl means a monovalent aromatic ring containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring or derivatives thereof, which may be one or more of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto.
In the present application, the term "heteroarylene" refers to a divalent or polyvalent group formed by further losing one or more hydrogen atoms.
In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) group may be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 3 to 30 carbon atoms, in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 5 to 18 carbon atoms, and in other embodiments the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total of from 5 to 12 carbon atoms.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, and the like.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight chain alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.
In the present application, specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In the present application, the cycloalkyl group having 3 to 10 carbon atoms may have 3, 4, 5, 6, 7, 8 or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.
In the present application, the deuterated alkyl group having 1 to 10 carbon atoms has, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10 carbon atoms. Specific examples of deuterated alkyl groups include, but are not limited to, tridentate methyl.
In the present application, the haloalkyl group having 1 to 10 carbon atoms has, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10 carbon atoms. Specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In the present application,-#、/>all refer to the chemical bonds that interconnect groups.
In the present application, the connection key is not positioned in relation to a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in formula (f), the naphthyl group represented by formula (f) is linked to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) to (f-10):
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X ') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by the formula (X ' -1) to (X ' -4) includes any possible linkage as shown in the formula (X ' -1):
by an off-site substituent in the context of the present application is meant a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in formula (Y) below, the substituent R' represented by formula (Y) is attached to the quinoline ring via an unoositioned bond, which means that it includes any of the possible linkages shown in formulas (Y-1) to (Y-7):
in some embodiments, the nitrogen-containing compound is selected from structures represented by the following formulas (1-1) to (1-16):
in some embodiments, ring a and ring B are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, or a pyrene ring.
In some embodiments, het is selected from the group consisting of:
- # represents a bond to L,representation and L 1 The key of the connection->Representation and L 2 A linked bond; wherein- >Represents +.>Wherein L is 2 Is a single bond, ar 2 Is hydrogen.
In some embodiments, het is selected from the group consisting of:
- # represents a bond to L,representation and L 1 The key of the connection->Representation and L 2 A linked bond; wherein the formula does not containRepresents +.>Wherein L is 2 Is a single bond, ar 2 Is hydrogen.
In some embodiments, L, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.
In some embodiments, L, L 1 And L 2 And are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.
Optionally L, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, fluoroalkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 5 to 12 carbon atoms.
In some embodiments, L, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstitutedUnsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.
Optionally L, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl, phenyl or naphthyl.
In some embodiments, L, L 1 And L 2 Identical or different and are each independently selected from a single bond or a substituted or unsubstituted group Q selected from the group consisting of:
the substituents in the above substituted groups Q are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl, phenyl or naphthyl.
In some embodiments, L, L 1 And L 2 Each independently selected from a single bond or the following groups:
in some embodiments, L is selected from a single bond or the following groups:
in some embodiments, L is a single bond.
In some embodiments, the Ar 1 Selected from the group consisting of 6, 7, 8, 9, 10, 11 carbon atomsA substituted or unsubstituted aryl group of 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30, a substituted or unsubstituted heteroaryl group of 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30;
Ar 2 a substituted or unsubstituted aryl group selected from the group consisting of hydrogen, a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.
In some embodiments, ar 1 A substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 7 to 20 carbon atoms; ar (Ar) 2 Selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 7 to 20 carbon atoms.
Alternatively, ar 1 And Ar is a group 2 Each of the substituents is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuteroalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, optionally any two adjacent substituents forming a benzene ring or a fluorene ring.
In some embodiments, ar 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl; ar (Ar) 2 Selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl.
Alternatively, ar 1 、Ar 2 Each of the substituents of (a) is independently selected from deuterium, fluoro, cyano, trimethylsilyl, tridentate methyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, biphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; optionally Ar 1 And Ar is a group 2 Any two adjacent substituents form a benzene ring or fluorene ring.
In some embodiments, ar 1 A group V selected from substituted or unsubstituted; ar (Ar) 2 A group V selected from hydrogen, substituted or unsubstituted; wherein the unsubstituted group V is selected from the group consisting of:
the substituted group V has one or more than two substituents, the substituents of the group V are each independently selected from deuterium, fluorine, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of the substituents on the group V is more than 1, the substituents are the same or different.
In some embodiments, ar 1 Selected from the following groups; ar (Ar) 2 Selected from hydrogen or the following groups:
in some embodiments of the present invention, in some embodiments, Selected from the group consisting of ∈ ->Selected from hydrogen or the following groups: />
In some embodiments, each R 1 、R 2 、R 3 And R is 4 Identical or different and are each independently selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
In some embodiments of the present application, in some embodiments,selected from the group consisting of: />
/>
In some embodiments, the nitrogen-containing compounds of the present application are selected from the group consisting of the compounds set forth in claim 13.
The second aspect of the present application provides an organic electroluminescent device, the organic electroluminescent device comprising an anode and a cathode which are disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound to improve voltage characteristics, efficiency characteristics and lifetime characteristics of the organic electroluminescent device.
Alternatively, the nitrogen-containing compound provided by the present application may be used to form at least one organic film layer in the functional layer.
Optionally, the functional layer includes an organic light emitting layer including the nitrogen-containing compound. The organic light-emitting layer may be composed of the nitrogen-containing compound provided by the present application, or may be composed of the nitrogen-containing compound provided by the present application together with other materials.
According to a specific embodiment, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (also referred to as a hole auxiliary layer) 322, an organic light emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked as shown in fig. 1.
In the present application, the anode 100 includes an anode material, which is 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, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
In the present application, the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, and may specifically be selected from the compounds shown below or any combination thereof:
In one embodiment, the first hole transport layer 321 may be composed of HT-1.
In one embodiment, second hole transport layer 322 consists of HT-2 or consists of HT-3.
Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present application. The material of the hole injection layer 310 is selected from, for example, the following compounds or any combination thereof:
in one embodiment, hole injection layer 310 is comprised of PD and HT-1.
In the present application, the organic light emitting layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light emitting layer 330 may include a metal chelating compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. Optionally, the host material comprises the nitrogen-containing compound of the present application, and further optionally, the host material of the organic light-emitting layer 330 comprises at least one of the above-described compounds 1 to 324 of the present application. Optionally, the host material further comprises RH-P.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application. Guest materials are also known as doping materials or dopants. Fluorescent dopants and phosphorescent dopants can be classified according to the type of luminescence. Specific examples of phosphorescent dopants include, but are not limited to:
in one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device or a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light emitting layer 330 comprises the nitrogen-containing compound of the present application. The guest material is, for example, RD-1 or GD-1.
In one embodiment of the present application, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light emitting layer 330 comprises the nitrogen-containing compound of the present application. In one embodiment, the host material of the organic light emitting layer 330 comprises the nitrogen-containing compound of the present application andor comprises the nitrogen-containing compound of the application and +.>
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, BTB, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present application is not particularly limited by comparison. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:
in one embodiment of the present application, electron transport layer 340 may be composed of ET-1 and LiQ, or of ET-2 and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).
A third aspect of the application provides an electronic device comprising an organic electroluminescent device according to the second aspect of the application.
According to one embodiment, as shown in fig. 2, an electronic device 400 is provided, which includes the organic electroluminescent device described above. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
Synthesis example
The following synthesis examples and examples serve to further illustrate and explain the context of the present application.
In general, the nitrogen-containing compounds of the present application may be prepared by the methods described herein. The meaning of the substituent symbols in the present application is the same as that of the substituent symbols in the formula I unless further specified. Those skilled in the art will recognize that: the chemical reactions described herein may be used to suitably prepare many other nitrogen-containing compounds of the present application, and other methods for preparing nitrogen-containing compounds of the present application are considered to be within the scope of the present application.
For example, one skilled in the art can synthesize other nitrogen-containing compounds of the present application by referring to or appropriately modifying the preparation methods provided herein, for example, by means of appropriate protecting groups, by using other known reagents outside the description of the present application, modifying reaction conditions, and the like.
In the synthesis examples described below, unless otherwise indicated, temperatures are in degrees celsius. Some reagents were purchased from commercial suppliers such as Aldrich Chemical Company, arco Chemical Company and Alfa Chemical Company, etc., and unless otherwise stated, none of these reagents were used without further purification. Some conventional reagents were purchased from Shandong chemical plant, guangdong chemical plant, guangzhou chemical plant, tianjin good-apartment chemical Co., ltd, tianjin Fuchen chemical plant, wuhan Xinhua remote technology development Co., qingdao Teng chemical Co., ltd, and Qingdao ocean chemical plant. Wherein, toluene is obtained by reflux drying of metallic sodium. N-hexane was dried over anhydrous sodium sulfate and used.
Unless otherwise stated, the following reactions are generally carried out under nitrogen or argon positive pressure, or by sleeving a dry tube on an anhydrous solvent; the reaction flask was capped with a suitable rubber stopper and the substrate was injected into the flask via syringe. The glassware was all dried.
1 HNMR spectra were recorded using a Bruker 400MHz or 600MHz nuclear magnetic resonance spectrometer. 1 H NMR Spectroscopy with CDCl 3 、CD 2 Cl 2 、D 2 O、DMSO-d 6 、CD 3 OD or acetone-d 6 Is solvent (in ppm).
(1) Synthesis of intermediate A-1
SM-A-1(10g,35.3mmol),SM-B-1(5.9g,35.3mmol),potassiumcarbonate(10.7g,77.7mmol),cuprousiodide(1.3g,7.1mmol),18-crownether-6(0.9g,3.5mmol),1,10-phenanthroline(2.8g,14.1mmol),N,N-dimethylformamide(100mL),thereactionwascompletedafter24h,cooledtoroomtemperature,500mLofwaterwasadded,alargeamountofsolidswasprecipitated,filtered,thefiltercakewascompletelydissolvedwith300mLofdichloromethane,washedwithwatertoneutrality,theorganiclayerwasdriedwithanhydrousmagnesiumsulfate,andconcentratedunderreducedpressuretoobtaincrudeproduct; the crude product was purified by silica gel column chromatography (dichloromethane/n-heptane) to give a-1 (9.1 g, yield 70%).
referringtothesynthesisofA-1,theintermediateA-XinTable1wassynthesizedusingSM-A-XinsteadofSM-A-1andSM-B-XinsteadofSM-B-1showninTable1.
Table 1:
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(2) Synthesis of intermediate B-1
After A-1 (10 g,27.1 mmol) was dissolved in methylene chloride, pyridine (6.4 g,81.2 mmol) was added under stirring at room temperature, and after cooling to 0℃trifluoromethanesulfonic anhydride (11.5 g,40.6 mmol) was added dropwise, and then the mixture was allowed to react at room temperature for 2 hours. After completion of the reaction, the pH was adjusted to neutrality with saturated aqueous sodium bicarbonate, extracted with dichloromethane (100 mL. Times.3), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded B-1 (8.1 g, 60% yield). Referring to the synthesis of B-1, intermediate B-X in Table 2 was synthesized using A-X shown in the table instead of A-1.
Table 2:
/>
(3) Synthesis of intermediate C-1
To a three-necked flask, B-1 (20 g,39.8 mmol), m-chlorobenzeneboronic acid (6.2 g,39.8 mmol), tetrakis (triphenylphosphine) palladium (0.5 g,0.4 mmol), anhydrous potassium carbonate (11 g,79.8 mmol), tetrabutylammonium bromide (0.13 g,0.4 mmol), toluene (160 mL), anhydrous ethanol (80 mL) and deionized water (40 mL) were sequentially added under nitrogen atmosphere, and stirring and heating were turned on to heat up to reflux reaction for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded C-1 (13 g, 70% yield).
Referring to the synthesis of C-1, intermediate C-X in Table 3 was synthesized using B-X shown in the table in place of B-1 and SM-C-X in place of m-chlorobenzeneboronic acid.
Table 3:
(4) Synthesis of intermediate D-1
After B-1 (20 g,39.9 mmol) was dissolved in 1, 4-dioxane (200 mL), tris (dibenzylideneacetone) dipalladium (0.4 g,0.4 mmol), potassium acetate (11.7 g,119.6 mmol), pinacol biborate (12.2 g,47.8 mmol), x-phos (0.2 g,0.4 mmol) was added, stirring and heating were turned on, and the temperature was raised to reflux reaction for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded D-1 (13.0 g, 68% yield).
Referring to the synthesis of D-1, the intermediate D-X in Table 4 was synthesized using either B-X or C-X shown in Table 4 in place of B-1.
Table 4:
/>
/>
synthesis of Compound 1:
to a three-necked flask, D-1 (20 g,39.8 mmol), SM-N-1 (6.2 g,39.8 mmol), tetrakis (triphenylphosphine) palladium (0.5 g,0.4 mmol), anhydrous potassium carbonate (11 g,79.8 mmol), tetrabutylammonium bromide (0.13 g,0.4 mmol), toluene (160 mL), anhydrous ethanol (80 mL) and deionized water (40 mL) were sequentially added under nitrogen atmosphere, and stirring and heating were turned on to heat up to reflux reaction for 16h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. Times.3 times), and the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded 1 (13 g, 70% yield).
Referring to the synthesis of compound 1, compound Y in Table 5 was synthesized using D-X instead of D-1 and SM-N-X instead of SM-N-1 shown in Table 5.
Table 5:
/>
/>
/>
/>
synthesis of Compound 384
To a 100mL three-necked flask under nitrogen atmosphere, compound 1 (10.0 g,17.1 mmol) and 100mL benzene-D were added 6 After heating to 60 ℃, trifluoromethanesulfonic acid (15.6 g,103.4 mmol) was added thereto, and the temperature was further raised to boiling and the reaction was stirred for 24 hours. After the reaction system was cooled to room temperature, 20mL of heavy water was added thereto, and after stirring for 10 minutes, saturated K was added 3 PO 4 The reaction solution was neutralized with an aqueous solution. The organic layers were extracted with dichloromethane (50 mL. Times.3), and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to give a crude product. Purification by silica gel column chromatography using n-heptane/dichloromethane as mobile phase afforded 384 (6.2 g, 60% yield).
Mass spectrum of the compound of synthesis example:
| numbering of compounds | m/z([M+H] + ) | Numbering of compounds | m/z([M+H] + ) |
| 1 | 585.3 | 4 | 661.3 |
| 44 | 751.3 | 89 | 685.3 |
| 110 | 685.3 | 145 | 765.3 |
| 218 | 787.3 | 228 | 735.3 |
| 238 | 801.3 | 241 | 787.3 |
| 191 | 711.3 | 196 | 735.3 |
| 381 | 685.3 | 256 | 779.3 |
| 255 | 825.3 | 257 | 735.3 |
| 251 | 775.3 | 382 | 765.3 |
| 307 | 737.3 | 305 | 761.3 |
| 314 | 787.3 | 374 | 679.3 |
| 383 | 663.3 | 353 | 761.3 |
| 359 | 863.4 | 364 | 837.3 |
| 385 | 771.4 | 384 | 604.4 |
| 29 | 558.3 | 30 | 598.3 |
| 30 | 598.3 | 32 | 614.3 |
| 33 | 584.3 | 34 | 608.3 |
| 35 | 614.3 |
The nuclear magnetic data of some compounds are shown in table 6 below:
device embodiment
The embodiment of the invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises the organic compound. The organic electroluminescent device according to the present invention will be described in detail with reference to examples. However, the following examples are only examples of the present invention and do not limit the present invention.
Example 1: red organic electroluminescent device
The anode pretreatment is carried out by the following steps: in the thickness of in turnThe ITO/Ag/ITO substrate is subjected to surface treatment by utilizing ultraviolet ozone and O2: N2 plasma to increase the work function of the anode, and the surface of the ITO substrate can be cleaned by adopting an organic solvent to remove impurities and greasy dirt on the surface of the ITO substrate.
On the experimental substrate (anode), PD and compound HT-1 were combined in 2%: co-evaporation is carried out at an evaporation rate ratio of 98% to form a film with a thickness ofIs then vacuum evaporated HT-1 on the hole injection layer, is +.>Is provided.
Vacuum evaporating compound HT-2 on the first hole transport layer to form a film of thicknessIs provided.
Then, on the second hole transport layer, the compound 89:RH-P:RD-1 was co-evaporated at a ratio of 49% to 2% to form a film having a thickness ofRed light emitting layer (EML).
On the light-emitting layer, mixing and evaporating the compounds ET-1 and LiQ in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +.>Then magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate of 1:9, and vacuum vapor deposited on the electron injection layer to form a film having a thickness +. >Is provided.
In addition, the thickness of the vacuum evaporation on the cathode isAnd (3) forming an organic capping layer (CPL), thereby completing the manufacture of the red organic electroluminescent device.
Examples 2 to 26
An organic electroluminescent device was prepared by the same method as in example 1, except that the compound Z in table 6 below was used instead of the compound 89 in example 1 when the light-emitting layer was prepared.
Comparative examples 1 and 2
An organic electroluminescent device was prepared by the same method as in example 1, except that compound a, compound B, and compound 89 in example 1 were replaced, respectively, when the light-emitting layer was prepared.
Wherein, in preparing each example and comparative example, the structures of the compounds used are as follows:
wherein, in preparing each example and comparative example, the structures of the compounds used are as follows:
performance test was performed on the red organic electroluminescent devices prepared in examples 1 to 26 and comparative examples 1 to 2, specifically at 10mA/cm 2 IVL performance of the device was tested under the conditions of T95 device lifetime at 20mA/cm 2 Is carried out under the conditions of (2) and the test results are shown in Table 7 below.
TABLE 7
Referring to Table 7 above, it is understood that by comparing the performances of the organic electroluminescent devices prepared in examples 1 to 58 with those of comparative examples 1 to 4, the luminous efficiency of the organic electroluminescent device is improved by at least 12% and the lifetime is improved by at least 11.8% when the nitrogen-containing compound of the present invention is used as a host material for a red organic electroluminescent device.
Example 27: green light organic electroluminescent device
The anode was prepared by the following procedure: will be of the thickness ofThe ITO substrate (manufactured by Corning) was cut into a size of 40mm by 0.7mm, and a test substrate having a cathode, an anode and an insulating layer pattern was prepared by using a photolithography process, and surface treatment was performed using ultraviolet ozone and O2: N2 plasma to increase the work function of the anode (test substrate) and remove scum.
On the experimental substrate (anode), PD and compound HT-1 were combined in 2%: co-evaporation is carried out at an evaporation rate ratio of 98% to form a film with a thickness ofIs formed by vapor deposition of HT-1 on a Hole Injection Layer (HIL) to a thickness of +.>First hole transport of (2)And (5) conveying a layer.
Vacuum evaporating HT-3 on the first hole transport layer to form a film with a thickness ofIs provided.
On the second hole transport layer, compound 1: GH-P: GD-1 was found to be 54%:42%: co-evaporation was performed at a ratio of 4% (co-evaporation rate ratio: compound B-3: gh-P: GD-1=0.6:0.4:0.1), to form a film having a thickness ofGreen light emitting layer (EML).
ET-1 and LiQ are mixed and evaporated in a weight ratio of 1:1 to formA thick Electron Transport Layer (ETL) on which Yb is vapor deposited to form a thickness +. >Electron Injection Layer (EIL) of (a), then magnesium (Mg) and silver (Ag) are mixed at 1:9, and vacuum evaporating on the electron injection layer to form a film with a thickness of +.>Is provided.
In addition, the thickness of the vapor deposited on the cathode isAn organic capping layer (CPL) was formed to complete the fabrication of an organic light emitting device, and the fabricated device was designated as example 22.
Examples 28 to 35
Organic electroluminescent devices were fabricated by the same method as in example 28 except that compound T shown in Table 7 was used instead of compound 1 in the formation of the light-emitting layer, and the fabricated devices were designated as examples 28 to 385
Comparative examples 3 to 4
An organic electroluminescent device was fabricated by the same method as in example 28, except that compound C and compound D were used in place of compound 1 of example 28, respectively, in the fabrication of a light-emitting layer.
Wherein, in preparing each example and comparative example, the structures of the compounds used are as follows:
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the green organic electroluminescent devices of examples 27 to 35 and comparative examples 3 to 4 were subjected to performance test, specifically at 10mA/cm 2 Under the condition of testing IVL performance of the device, T 95 The service life of the device is 20mA/cm 2 Is carried out under the conditions of (2) and the test results are shown in Table 8 below.
TABLE 8
Referring to Table 8 above, it can be seen that by comparing the performances of the organic electroluminescent devices prepared in examples 28 to 35 with those of comparative examples 3 to 4, the luminous efficiency of the organic electroluminescent device was improved by at least 12.9% and the lifetime was improved by at least 14.7% when the nitrogen-containing compound of the present invention was used as a host material for a red organic electroluminescent device.
The preferred embodiments of the present invention have been described in detail above with reference to the accompanying drawings, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.
In addition, the specific features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described further.
Claims (15)
1. A nitrogen-containing compound having a structure represented by formula 1:
in formula 1, ring A and ring B are each independently selected from aromatic rings having 6 to 16 carbon atoms;
het is a nitrogen-containing heteroarylene group having 3 to 20 carbon atoms;
L、L 1 And L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different and are each independently selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
L、L 1 、L 2 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, phosphono having 6 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms. Optionally Ar 1 、Ar 2 Any two adjacent substituents form a saturated or unsaturated 3-15 membered ring;
each R is 1 、R 2 、R 3 And R is 4 Identical or different and are each independently selected from Deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms or cycloalkyl group having 3 to 10 carbon atoms;
n 1 represents R 1 Number n of (n) 2 Represents R 2 Number n of (n) 1 And n 2 Each independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.
2. The nitrogen-containing compound according to claim 1, wherein ring a and ring B are each independently selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, or a pyrene ring.
3. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound has a structure represented by the following formulas (1-1) to (1-16):
4. the nitrogen-containing compound according to claim 1, wherein Het is selected from the group consisting of:
- # represents a bond to L,representation and L 1 The key of the connection->Representation and L 2 A linked bond; wherein the formula does not containRepresents +.>Wherein L is 2 Is a single bond, ar 2 Is hydrogen.
5. The nitrogen-containing compound according to claim 1, wherein Het is selected from the group consisting of:
- # represents a bond to L, Representation and L 1 The key of the connection->Representation and L 2 A linked bond; wherein->Represents +.>Wherein L is 2 Is a single bond, ar 2 Is hydrogen.
6. The nitrogen-containing compound of claim 1, wherein L, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstitutedFluorenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted anthrylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted carbazolylene;
optionally L, L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl, phenyl or naphthyl.
7. The nitrogen-containing compound of claim 1, wherein L, L 1 And L 2 Each independently selected from a single bond or the following groups:
8. the nitrogen-containing compound according to claim 1, wherein Ar 1 A substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 7 to 20 carbon atoms; ar (Ar) 2 Selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 7 to 20 carbon atoms;
alternatively, ar 1 And Ar is a group 2 Each of the substituents is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuteroalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, optionally any two adjacent substituents forming a benzene ring or a fluorene ring.
9. The nitrogen-containing compound according to claim 1, wherein Ar 1 A group V selected from substituted or unsubstituted; ar (Ar) 2 A group V selected from hydrogen, substituted or unsubstituted; wherein the unsubstituted group V is selected from the group consisting of:
the substituted group V has one or more than two substituents, the substituents of the group V are each independently selected from deuterium, fluorine, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of the substituents on the group V is more than 1, the substituents are the same or different.
10. The nitrogen-containing compound according to claim 1, wherein,selected from the group consisting of,selected from hydrogen or the following groups:
11. the nitrogen-containing compound according to claim 1, wherein each R 1 、R 2 、R 3 And R is 4 Identical or different and each is independent of the otherIs selected from deuterium, fluoro, cyano, tridentate methyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, t-butyl, phenyl or naphthyl.
12. The nitrogen-containing compound according to claim 1, wherein,selected from the group consisting of:
13. the nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
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14. the organic electroluminescent device comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 13; optionally, the functional layer comprises an organic light emitting layer comprising the nitrogen-containing compound.
15. An electronic device comprising the organic electroluminescent device of claim 14.
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