CN112876455A - Nitrogen-containing compound, and organic electroluminescent device and electronic device using same - Google Patents
Nitrogen-containing compound, and organic electroluminescent device and electronic device using same Download PDFInfo
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- CN112876455A CN112876455A CN202110024392.5A CN202110024392A CN112876455A CN 112876455 A CN112876455 A CN 112876455A CN 202110024392 A CN202110024392 A CN 202110024392A CN 112876455 A CN112876455 A CN 112876455A
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims description 202
- 239000010410 layer Substances 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 28
- 229910052805 deuterium Inorganic materials 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000000732 arylene group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000002346 layers by function Substances 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052701 rubidium Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 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 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 3
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 238000003756 stirring Methods 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 14
- 239000007858 starting material Substances 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 229910021642 ultra pure water Inorganic materials 0.000 description 9
- 239000012498 ultrapure water Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 125000005561 phenanthryl group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000004537 pulping Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 3
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000010009 beating Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940125807 compound 37 Drugs 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- HPJCIBVGJBEJPU-UHFFFAOYSA-N 1-fluoro-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(F)=CC=C2 HPJCIBVGJBEJPU-UHFFFAOYSA-N 0.000 description 2
- ZAARQOHTIYBPNJ-UHFFFAOYSA-N 2,4-dichloro-6-naphthalen-2-yl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=C3C=CC=CC3=CC=2)=N1 ZAARQOHTIYBPNJ-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JKHCVYDYGWHIFJ-UHFFFAOYSA-N Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 Chemical compound Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 JKHCVYDYGWHIFJ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 125000004431 deuterium atom Chemical group 0.000 description 2
- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000007740 vapor deposition Methods 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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 239000011651 chromium Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- 239000011147 inorganic material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000005956 isoquinolyl group Chemical group 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
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000149 penetrating effect Effects 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
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-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
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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Abstract
The application belongs to the technical field of organic materials, and provides a nitrogen-containing compound and organic electroluminescence using the sameAn optical device and an electronic device, wherein the nitrogen-containing compound has a structure shown in formula I; wherein, X1、X2、X3Each independently selected from N or CH, and at least one is N. The nitrogen-containing compound is used in an organic electroluminescent device, and can improve the performance of the device.
Description
Technical Field
The application belongs to the technical field of organic materials, and particularly provides a nitrogen-containing compound, and an organic electroluminescent device and an electronic device using the nitrogen-containing compound.
Background
With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Such electronic components generally include a cathode and an anode that are oppositely disposed, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers and generally includes an energy conversion layer, a hole transport layer between the energy conversion layer and the anode, and an electron transport layer between the energy conversion layer and the cathode.
Taking an organic electroluminescent device as an example, the organic electroluminescent device generally comprises an anode, a hole transport layer, an electroluminescent layer as an energy conversion layer, an electron transport layer and a cathode, which are sequentially stacked. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on 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 and release energy outwards, so that the electroluminescent layer emits light outwards.
At present, the problems of low luminous efficiency, overhigh driving voltage and the like exist in the using process of an organic electroluminescent device, so that the performance of the organic electroluminescent device is reduced.
Disclosure of Invention
In view of the above problems in the prior art, the present application aims to provide a nitrogen-containing compound used in an organic electroluminescent device to improve the performance of the organic electroluminescent device, and an organic electroluminescent device and an electronic apparatus using the same.
In order to achieve the above object, the first aspect of the present application provides a nitrogen-containing compound, which has a structure represented by formula I:
wherein, X1、X2、X3Are identical or different from each other, are each independently selected from N or CH, and at least one is N;
Ar1and Ar2The same or different from each other, each is independently selected from substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L、L1and L2The same or different from each other, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
y is selected from C (R)1R2)、Si(R1R2) O, S or N (R)3)；R1、R2And R3The same or different from each other, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 15 carbon atoms; optionally, R1And R2Form a ring together with the atoms to which they are commonly attached;
Ar1and Ar2Wherein the substituents are the same or different from each other and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and optionally, any two adjacent substituents form a ring;
L、L1、L2wherein the substituents are the same or different from each other and each is independently selected from deuterium, a halogen group, cyano, phenyl, naphthyl, pyridylA trialkylsilyl group having 3-7 carbon atoms, an alkyl group having 1-4 carbon atoms, a haloalkyl group having 1-4 carbon atoms, a cycloalkyl group having 5-10 carbon atoms, an alkoxy group having 1-4 carbon atoms, or an alkylthio group having 1-4 carbon atoms;
Ra、Rband RcIdentical or different from each other and each independently selected from deuterium, a halogen group, a cyano group, a group A, a trialkylsilyl group having 3 to 7 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms; the group A is selected from substituted or unsubstituted aryl with 6-15 carbon atoms or substituted or unsubstituted heteroaryl with 4-10 carbon atoms, and the substituent in the group A is selected from deuterium, fluorine, cyano and alkyl with 1-4 carbon atoms;
na、nband ncEach represents Ra、RbAnd RcThe number of (2); n isaSelected from 0, 1,2, 3 or 4, when n isaWhen greater than 1, any two RaThe same or different; n isbSelected from 0, 1 or 2, when nbWhen it is 2, two RbThe same or different; n iscSelected from 0, 1,2, 3 or 4, when n iscWhen greater than 1, any two RcThe same or different.
In a second aspect, the present application provides an organic electroluminescent device comprising a nitrogen-containing compound as described in the first aspect of the present application.
A third aspect of the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
The nitrogen-containing compound is asymmetric in the whole molecule in the structure, so that the amorphous property of the material is increased, and the charge transmission becomes smoother; the nitrogen-containing heterocycle and the carbazole have a certain rotation angle in the molecular configuration, so that the HOMO value of the nitrogen-containing compound can be adjusted, the HOMO value of the nitrogen-containing compound can be matched with an adjacent film layer, and the driving voltage of the organic electroluminescent device can be reduced; and in this structureHOMO and LUMO are respectively at different positions of the molecule, thereby being beneficial to improving T1Thereby improving the luminous efficiency.
Drawings
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Description of the reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 321. a first hole transport layer; 322. a second hole transport layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 400. an electronic device.
Detailed Description
The following detailed description of specific embodiments of the present disclosure is provided in connection with the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present disclosure, are given by way of illustration and explanation only, not limitation.
In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by formula I:
wherein, X1、X2、X3Are identical or different from each other, are each independently selected from N or CH, and at least one is N;
Ar1and Ar2The same or different from each other, each is independently selected from substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L、L1and L2The same or different from each other, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
y is selected from C (R)1R2)、Si(R1R2) O, S or N (R)3)；R1、R2And R3The same or different from each other, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 15 carbon atoms; optionally, R1And R2Form a ring together with the atoms to which they are commonly attached;
Ar1and Ar2Wherein the substituents are the same or different from each other and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and optionally, any two adjacent substituents form a ring;
L、L1、L2wherein the substituents are the same or different from each other and each is independently selected from deuterium, a halogen group, cyano, phenyl, naphthyl, pyridyl, trialkylsilyl having 3 to 7 carbon atoms, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms;
Ra、Rband RcIdentical or different from each other and each independently selected from deuterium, a halogen group, a cyano group, a group A, a trialkylsilyl group having 3 to 7 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms; the group A is selected from substituted or unsubstituted aryl with 6-15 carbon atoms or substituted or unsubstituted heteroaryl with 4-10 carbon atoms, and the substituent in the group A is selected from deuterium, fluorine, cyano and alkyl with 1-4 carbon atoms;
na、nband ncEach represents Ra、RbAnd RcThe number of (2); n isaIs selected from 01,2, 3 or 4, when n isaWhen greater than 1, any two RaThe same or different; n isbSelected from 0, 1 or 2, when nbWhen it is 2, two RbThe same or different; n iscSelected from 0, 1,2, 3 or 4, when n iscWhen greater than 1, any two RcThe same or different.
In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups. For example,') "
Wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the 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 with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rx). For example, "substituted or unsubstituted aryl" means having a substituent RxOr an unsubstituted aryl group. Wherein the above-mentioned substituent is RxFor example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, a triarylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, or the like may be mentioned. In addition, "two adjacent substituents" includes the following two cases: with two substituents R attached to the same atomxAnd two adjacent atoms are respectively connected with a substituent RxThe case (1). When two substituents R are attached to the same atomxWhen two substituents R are presentxMay be independently present or attached to each other to form a ring with said atom; when two adjacent atoms of the functional group are present and each is bound by a substituent RxWhen two adjacent substituents R are presentxMay be present independently or may be fused to form a ring with the functional group to which it is attached.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L is selected from substituted arylene having 12 carbon atoms, then all of the carbon atoms of the arylene and the substituents thereon are 12.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bond conjugation, monocyclic aryl and fused ring aryl groups joined by carbon-carbon bond conjugation, two or more fused ring aryl groups joined by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. Specific examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
and the like. In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom.
In the present application, substituted aryl groups may be aryl groups in which one or two or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, and the like. It is understood that the number of carbon atoms of a substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, a substituted aryl group having a carbon number of 18 refers to the total number of carbon atoms of the aryl group and the substituent being 18.
In the present application, heteroaryl means a monovalent aromatic ring containing at least one heteroatom, which may be at least one of B, O, N, P, Si, Se and S, in the ring or a derivative thereof. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation. In this application, a heteroarylene group refers to a divalent group formed by a heteroaryl group further lacking one hydrogen atom.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, alkoxy groups, alkylthio groups, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
The non-positional connection key referred to in this application
Refers to a single bond extending from the ring system, which means that one end of the connecting bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the rest of the compound molecule.
For example, as shown in formula (f), naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positioned bonds penetrating through the bicyclic ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) includes any possible connection mode shown in the formula (f-1) to the formula (f-10).
As another example, as shown in the following formula (X '), the phenanthryl group represented by formula (X') is bonded to other positions of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in formulas (X '-1) to (X' -4).
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes as shown in the formulae (Y-1) to (Y-7).
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms, and the number of carbon atoms may be, for example, 1,2, 3,4, 5, 6, 7, 8, 9, 10. Specific examples of the alkyl group having 1 to 10 carbon atoms include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, heptyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may include fluorine, iodine, bromine, chlorine, and the like.
In the present application, the number of carbon atoms of the aryl group as a substituent is, for example, 6 to 20, 6 to 18, 6 to 15, etc., the number of carbon atoms is, for example, 6, 10, 12, 14, 15, etc., and specific examples of the aryl group include, but are not limited to, phenyl, naphthyl, biphenyl, etc.
In the present application, the number of carbon atoms of the heteroaryl group as a substituent is, for example, 3 to 20, 3 to 18, 5 to 15, 6 to 12, etc., and the number of carbon atoms is, for example, 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, etc., and specific examples of the heteroaryl group include, but are not limited to, a pyridyl group, a quinolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, etc.
In the present application, the number of carbon atoms of the trialkylsilyl group may be 3 to 12, 3 to 7, etc., and specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, etc.
In the present application, the number of carbon atoms of the cycloalkyl group may be 3 to 10, 5 to 6, etc., and specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, etc.
In the present application, in the formula I,
represents:
r in (1)bAny two adjacent CH's on the attached phenyl rings and
the resulting groups are attached at the "#", "###" junctions, respectively. For example, when n isa、nbAnd ncWhen both are 0 and Y is S,
is concretely composed of
Specifically, the nitrogen-containing compound has a structure represented by any one of formulas 2-1 to 2-6:
in the application, X1、X2、X3At least one of which is N, in particular, X1、X2、X31,2 or 3 of which are N.
Alternatively, L, L1、L2Each 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 5 to 15 carbon atoms. For example, L, L1、L2Each independently selected from a single bond, or from a substituted or unsubstituted arylene group having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms, or from a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15 carbon atoms.
Alternatively, L, L1、L2Each independently selected from a single bond, substituted or unsubstituted phenyleneA group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, or a group selected from a novel subunit group in which a phenylene group and a naphthylene group are linked to each other.
Alternatively, L, L1、L2Wherein the substituents in (A) are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, trifluoromethyl and phenyl.
Alternatively, L is 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 6 to 12 carbon atoms.
Alternatively, L is selected from a single bond or from the group consisting of:
alternatively, L1、L2Each independently selected from a single bond, and a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
Alternatively, L1、L2Each independently selected from a single bond, substituted or unsubstituted phenylene. For example, L1、L2Each independently selected from a single bond or phenylene.
Alternatively, Ar1And Ar2Each independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms. For example, Ar1And Ar2Each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms or substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.
Alternatively, L1And Ar1Has a total number of carbon atoms of 6 to 20, L2And Ar2The total number of carbon atoms of (a) is 6 to 20.
In some embodiments, Ar1And Ar2Are the same or different from each other and are each independently selected from the group consisting of:
wherein the content of the first and second substances,
represents a chemical bond, M1Selected from a single bond or
G1～G5Each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N, C or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3The same or different;
G24～G33each independently selected from N, C or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different;
Z1selected from hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3-12 carbon atoms, alkyl having 1-10 carbon atoms, and halogen having 1-10 carbon atomsAn alkyl group, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkylthio group having 1 to 10 carbon atoms;
Z2～Z9、Z13each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3-12 carbon atoms, alkyl having 1-10 carbon atoms, haloalkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, alkoxy having 1-10 carbon atoms, alkylthio having 1-10 carbon atoms, heteroaryl having 3-18 carbon atoms, and triphenylsilyl;
Z10～Z20、F1～F4each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3-12 carbon atoms, alkyl having 1-10 carbon atoms, haloalkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, alkoxy having 1-10 carbon atoms, alkylthio having 1-10 carbon atoms, aryl having 6-18 carbon atoms, heteroaryl having 3-18 carbon atoms, and triphenylsilyl; optionally, any two adjacent Z19Forming a ring; optionally, any two adjacent Z20Forming a ring;
h1～h21by hkIs represented by Z1～Z21With ZkK is a variable and represents an arbitrary integer of 1 to 21, hkRepresents a substituent HkThe number of (2); wherein, when k is selected from 5 or 17, hkSelected from 1,2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, hkSelected from 1,2, 3 or 4; when k is selected from 1,3, 4,6, 9 or 14, hkSelected from 1,2, 3,4 or 5; when k is 13, hkSelected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, hkSelected from 1,2, 3,4, 5, 6 or 7; when k is 20, hkSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11, hkSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; and when h iskWhen greater than 1, any two ZkThe same or different;
K1selected from O, S, N (Z)22)、C(Z23Z24)、Si(Z23Z24) (ii) a Wherein Z is22、Z23、Z24Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, or Z23And Z24Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are commonly linked;
K2selected from single bond, O, S, N (Z)25)、C(Z26Z27)、Si(Z26Z27) (ii) a Wherein Z is25、Z26、Z27Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, or Z26And Z27Are linked to each other so as to form a saturated or unsaturated ring having 3 to 15 carbon atoms with the atoms to which they are linked together.
In the formulae i-13 to i-15, F2To F4Fi, where i is a variable, may represent 2, 3, or 4. For example, when i is 2, Fi means F2. It should be understood that when the non-aligned connection is bonded to c (Fi), Fi in c (Fi) is not present. For example, in the chemical formula i-13, when
Is connected to G12When, G12Only C atoms can be represented, namely the structure of the chemical formula i-13 is specifically:
in the present application, Z is as defined above23And Z24Z above26And Z27In both groups, the ring formed by the interconnection of the two groups in each group may be saturated or unsaturated, for example a saturated or unsaturated 3 to 13 membered ring may be formed. For example, in the formula i-10, when K is2And M1Are all single bonds, Z19Is hydrogen, and K1Is C (Z)23Z24) When Z is23And Z24When they are linked to each other so as to form a 5-membered ring with the atoms to which they are commonly attached, formula i-10 is
Likewise, the formula i-10 can also be represented
I.e. H23And H24The atoms that are linked to each other to be commonly bound to them form a partially unsaturated 13-membered ring.
Alternatively, Ar1And Ar2Each substituent in (a) is independently selected from: deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, heteroaryl having 5 to 12 carbon atoms, aryl having 6 to 15 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, haloalkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms.
Ar1And Ar2Specific examples of the substituent in (1) include, but are not limited to, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, pyridyl, phenyl, naphthyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methoxy, methylthio, and the like, respectively.
Alternatively, Ar1And Ar2Are identical or different and are each independently selected from substituted or unsubstituted radicals V1Unsubstituted radicals V1Selected from the group consisting of:
substituted radicals V1Wherein the substituent group is independently selected from deuterium, fluorine, cyano, alkyl group having 1 to 4 carbon atoms, trifluoromethyl, cycloalkyl group having 5 to 10 carbon atoms, trialkylsilyl group having 3 to 7 carbon atoms, and phenyl; when substitutedWhen the number of the groups is more than 1, the substituents may be the same or different.
Optionally, a substituted group V1The substituents in (a) are independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, cyclopentyl, cyclohexyl, trimethylsilyl, phenyl.
Further optionally, Ar1And Ar2Each independently selected from the group consisting of:
alternatively, R1、R2And R3Each independently selected from alkyl with 1-4 carbon atoms and aryl with 6-12 carbon atoms; optionally, R1And R2Form a ring together with the atoms to which they are commonly attached.
In this application, when Y is C (R)1R2) And R is1And R2When they form a ring together with the atom (C atom) to which they are commonly attached, Y may have, for example, a structure of:
alternatively, R1And R2Each independently selected from methyl, phenyl; r3Selected from phenyl, naphthyl or biphenyl.
In the present application, optionally na、nbAnd ncEach independently selected from 0 or 1.
Alternatively, Ra、RbAnd RcEach independently selected from deuterium, fluoro, cyano, phenyl, biphenyl, naphthyl, trialkylsilyl having 3-7 carbon atoms, alkyl having 1-4 carbon atoms, fluoromethyl, cycloalkyl having 5-10 carbon atoms, pyridyl, fluoro-substituted phenyl, deuterium-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl.
Alternatively, Ra、RbAnd RcEach independently selected from deuterium, fluoro, cyano, phenyl, biphenyl, naphthyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, fluoromethyl, cyclopentyl, cyclohexyl, pyridyl, fluoro-substituted phenyl, deuterium-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl.
In one embodiment, Y is selected from O, S or N (R)3)，R3Selected from phenyl, naphthyl and biphenyl.
Preferably, Y is selected from O or S, in which case the nitrogen-containing compound can further improve the lifetime of the OLED device.
Optionally, the nitrogen-containing compound is selected from the group consisting of:
the synthesis method of the nitrogen-containing compound provided by the present application is not particularly limited, and those skilled in the art can determine an appropriate synthesis method according to the preparation method provided by the synthesis examples section of the present application in combination with the nitrogen-containing compound. In other words, the synthesis examples section of the present invention illustratively provides methods for the preparation of nitrogen-containing compounds, and the starting materials employed may be obtained commercially or by methods well known in the art. All nitrogen-containing compounds provided herein are available to those skilled in the art from these exemplary preparative methods, and all specific preparative methods for preparing the nitrogen-containing compounds will not be described in detail herein, and should not be construed as limiting the present application.
A second aspect of the present application provides an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises a nitrogen-containing compound according to the first aspect of the present application.
The nitrogen-containing compound provided by the present application can be used to form at least one organic film layer in a functional layer to improve efficiency characteristics and lifetime characteristics of an organic electroluminescent device.
In a specific embodiment, the functional layer includes an organic light-emitting layer including the nitrogen-containing compound. Generally, the organic light emitting layer may include a host material and a guest material, wherein the host material includes the nitrogen-containing compound of the present application.
As shown in fig. 1, the organic electroluminescent device may include an anode 100, a first hole transport layer 321, a second hole transport layer 322, an organic light emitting layer 330 as an energy conversion layer, an electron transport layer 340, and a cathode 200, which are sequentially stacked.
Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the first hole transport layer 321 and the second hole transport layer 322 each include one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine-based compounds, or other types of compounds.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. The host material of the organic light emitting layer 330 may contain the nitrogen-containing compound of the present application. Further alternatively, the organic light emitting layer 330 may be composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, and the exciton transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
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 is not particularly limited in the present application.
According to a specific embodiment, the organic electroluminescent device is a green device, wherein the host material in the organic light-emitting layer 330 comprises the nitrogen-containing compound of the present application. The host material may be comprised of the nitrogen-containing compounds provided herein; alternatively, it may be composed of the nitrogen-containing compounds provided herein in combination with other materials.
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, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials.
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 multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Preferably, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be composed of F4-TCNQ.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed 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 or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the electron injection layer 350 may include LiQ.
In a third aspect, the present application provides an electronic device comprising an organic electroluminescent device as described in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
The method for synthesizing the nitrogen-containing compound of the present application will be specifically described below with reference to the synthesis examples.
The compounds of the present invention were synthesized using the following methods.
Synthesis of intermediates D-I:
1. intermediates D-I
(1) 2-bromocarbazole (9.10g,37mmol), methyl 2-aminobenzoate (8.41g,37mmol) and toluene (100 mL) are added into a 500mL three-neck flask with a nitrogen protection and condensation reflux device, stirring and heating are started, sodium tert-butoxide (5.28g,55mmol), 2-dicyclohexylphosphonium-2, 6-dimethoxy-biphenyl (S-phos) (0.15g,0.37mmol) and tris (dibenzylideneacetone) dipalladium (Pd) are added in sequence when the temperature rises to 50 DEG C2(dba)3) (0.1g,0.18 mmol); heating to toluene reflux, reacting for 6h, stopping stirring and heating after the reaction is finishedWhen the temperature is reduced to room temperature, the obtained reaction liquid is processed; adding 80mL of ultrapure water into the reaction solution, stirring and separating the solution, extracting the water phase twice by using 100mL of toluene each time, combining the organic phases, and washing the organic phases for three times by using 100mL of ultrapure water each time; drying with anhydrous sodium sulfate, passing through silica gel column, eluting the column with 200mL of toluene after passing, concentrating the organic phase to 80mL of the remaining, heating to completely dissolve the solid, cooling to crystallize, filtering the solid, and recrystallizing with 45mL of dichloroethane to obtain intermediate B-1 as a white solid (7.26g, 50% yield).
(2) Adding an intermediate B-1(14.52g,37mmol), THF (120 mL) and 2mol/L hydrochloric acid solution (30mL) into a 500mL three-neck flask, starting stirring and heating, heating to 60 ℃, reacting for 8 hours, stopping stirring and heating after the reaction is finished, and starting treatment when the temperature is reduced to room temperature; separating liquid, extracting the water phase twice by using 100mL of dichloromethane each time, combining organic phases, and washing three times by using 100mL of ultrapure water each time; drying with anhydrous sodium sulfate, concentrating the filtrate to dryness, beating twice with 80mL n-heptane, cooling to room temperature and filtering to obtain intermediate B-2(9.80g, yield 70%).
(3) Adding the intermediate B-2(14.00g,37mmol) and 112mL of glacial acetic acid into a 500mL three-necked flask, starting stirring and heating, heating to 60 ℃, adding 1mL of concentrated sulfuric acid (98 wt%), reacting for 10h, filtering after the reaction is finished, beating twice with 80mL of anhydrous ethanol, cooling to room temperature, filtering, separating by a column, and eluting with THF and n-heptane (3: 1, volume ratio) to obtain an intermediate D-1(4.99g, yield 37.5%).
2. The intermediates D-I listed in Table 1 were synthesized by referring to the method for the intermediate D-1, except that the raw material I was used instead of 2-bromocarbazole and the raw material II was used instead of methyl 2-aminobenzoate, and the structures of the main raw materials, the intermediate D-I and the total yield thereof were as shown in Table 1.
TABLE 1
Synthesis example 1: synthesis of Compound 1
Adding an intermediate D-1(13.41g,37mmol) and 100mL of N, N-Dimethylformamide (DMF) into a 500mL three-necked flask, introducing nitrogen for protection, starting stirring, cooling to 5-10 ℃, adding NaH (1.15g,48mmol), dissolving 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (9.86g,37mmol) in 40mL of DMF, dropwise adding the solution into a reaction system, reacting for 6h, filtering after the reaction is finished, pulping with 60mL of acetone, separating the product by a column, and obtaining a compound 1(8.78g, yield 40%), wherein the eluent is petroleum ether and ethyl acetate (4: 1, volume ratio): 592.2[ M + H ] M/z]+。
Synthesis examples 2 to 4
The compounds in table 2 were synthesized with reference to the synthesis method of compound 1, except that intermediate D-I was used instead of intermediate D-1, and the main raw materials, compounds, and their structures, yields, and mass spectrum characterization structures used are shown in table 2.
TABLE 2
Synthesis of intermediate C-I
1. Synthesis of intermediate C-1
(1) Adding 1-fluorocarbazole (12.95g,70mmol), 2- (methoxycarbonyl) phenol (10.65g,70mmol), cesium carbonate (34.21,105mmol) and DMF (100 mL) into a 500mL three-neck flask with a nitrogen protection and condensation reflux device, introducing nitrogen protection, starting heating and stirring, heating to 120 ℃, reacting for 18 hours, cooling the reaction solution to room temperature after the reaction is finished, extracting with 200mL of toluene, washing with 800mL of ultrapure water, drying with anhydrous sodium sulfate, passing through a silica gel column after the extraction is finished, concentrating the column-passing solution to the residual 80mL, heating to completely dissolve the solid, slowly cooling for recrystallization, separating the product through the column, and obtaining the product intermediate A-13(13.32g, yield 60%) by using petroleum ether and THF (4: 1, volume ratio).
(2) Adding the intermediate A-13(11.74g,37mmol), THF (120 mL) and 2mol/L hydrochloric acid (30mL) into a 500mL three-neck flask, starting stirring and heating, heating to 60 ℃, reacting for 8 hours, stopping stirring and heating after the reaction is finished, and starting treatment reaction when the temperature is reduced to room temperature; separating, extracting the water phase twice by using 100mL of dichloromethane each time, combining the organic phases, and washing three times by using 100mL of ultrapure water each time; drying with anhydrous sodium sulfate, concentrating the filtrate to dryness, beating twice with 80mL n-heptane, cooling to room temperature and filtering to obtain intermediate B-13(6.73g, yield 60%).
(3) Adding the intermediate B-13(11.22g,37mmol) and 112mL of glacial acetic acid into a 500mL three-necked bottle, starting stirring and heating, and heating to 60 ℃; 1mL of concentrated sulfuric acid (98 wt%) was added to the reaction mixture, the reaction was carried out for 10 hours, filtration was carried out after completion of the reaction, the mixture was thermally slurried twice with 80mL of anhydrous ethanol, cooled to room temperature and filtered, and the filtrate was separated by column chromatography using THF and n-heptane (3: 1, volume ratio) as leacheate to obtain intermediate C-1(7.60g, yield 72%).
2. The intermediates C-I listed in Table 3 were synthesized by referring to the method for the intermediate C-1, using the raw material I in place of 1-fluorocarbazole and the raw material II in place of 2- (methoxycarbonyl) phenol, and the structures of the main raw material, the intermediates C-I and the total yields thereof are shown in Table 3.
TABLE 3
Synthesis example 5: synthesis of Compound 13
Adding an intermediate C-1(10.55g,37mmol) and 100mL of DMF (dimethyl formamide) into a 500mL three-necked flask, introducing nitrogen for protection, starting stirring, cooling to 5-10 ℃, adding NaH (1.15g,48mmol), dissolving 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (9.86g,37mmol) with 40mL of DMF, dropwise adding into a reaction system, reacting for 5h, filtering after the reaction is finished, pulping with 60mL of acetone, separating the product by using a column, wherein the eluent is petroleum ether and ethyl acetate (6: 1, volume ratio), obtaining a compound 13(8.60g, yield 45%), and mass spectrum: m/z 517.2[ M + H ═ M]+。
Synthesis examples 6 to 13
The compounds of table 4 were synthesized with reference to the synthesis of compound 13, except that intermediate C-I was used instead of intermediate C-1 and starting material a was used instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, and the main starting materials, compounds and their structures, yields and mass spectrometric characterization structures used are shown in table 4.
TABLE 4
Nuclear magnetism of compound 55:1H NMR(400MHz,CD2Cl2):8.72(d,1H),8.58(d,4H),8.38(d,1H),8.10(d,1H),7.73(dd,1H),7.68-7.61(m,6H),7.61-7.56(m,2H),7.51-7.40(m,7H),7.02(t,1H)。
synthesis example 14: synthesis of Compound 37
Adding the intermediate D-1(13.41g,37mmol) and 100mL of DMF (dimethyl formamide) into a 500mL three-necked flask, introducing nitrogen for protection, starting stirring, cooling to 5-10 ℃, adding NaH (1.15g,48mmol), dissolving 2-chloro-4- (biphenyl-4-yl) -6-phenyl-1, 3, 5-triazine (12.72g,37mmol) with 40mL of DMF, dropwise adding into the reaction system, reacting for 8h, adding 50mL of deionized water after the reaction is finished, stirring for 30min, filtering, pulping with 60mL of ethanol, separating the product by a column, and obtaining a mass spectrum of a compound 37(12.39g, yield 50%) by using petroleum ether and THF (3: 1, volume ratio): 668.2[ M + H ] M/z]+。
Synthesis examples 15 to 18
The compounds of table 5 were synthesized with reference to the synthesis of compound 37, except that intermediate D-I was used instead of intermediate D-1 and starting material a was used instead of 2-chloro-4- (biphenyl-4-yl) -6-phenyl-1, 3, 5-triazine, the main starting materials, compounds and their structures, yields and mass spectrometry characterization structures used are shown in table 5.
TABLE 5
Synthesis of intermediate a-12:
in a 500mL three-necked flask with nitrogen protection and a condensing reflux device, 2, 4-dichloro-6-naphthalen-2-yl- [1,3,5] triazine (19.06g,70mmol), dibenzofuran-2-boronic acid (14.84g,70mmol), potassium carbonate (30.69g,140mmol), tetrabutylammonium bromide (4.5g,14mmol), and 120mL of toluene, 30mL of ethanol, and 30mL of ultrapure water (30mL) were charged; introducing nitrogen for protection, starting heating and stirring, adding tetratriphenylphosphine palladium (0.45g,0.4mmol) when the temperature rises to 40 ℃, heating to reflux reaction for 18 hours, cooling the reaction liquid to room temperature after the reaction is finished, extracting with 200mL of methylbenzene, washing with 400mL of ultrapure water, drying with anhydrous sodium sulfate, concentrating until no liquid flows out, purifying with a silica gel column, wherein the eluent is petroleum ether and ethyl acetate (3: 1, volume ratio), and obtaining a product a-12(16.97g, yield 60%).
Synthesis of intermediates A-I
1. Synthesis of intermediate A-1
Adding 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (18.73g,70mmol), p-bromobenzoic acid (14.00g,70mmol), potassium carbonate (30.69g,140mmol), tetrabutylammonium bromide (4.5g,14mmol), toluene 120mL, ethanol 30mL and ultrapure water 30mL into a 500mL three-neck flask with a nitrogen protection and condensation reflux device, introducing nitrogen protection, starting heating and stirring, adding tetratriphenylphosphine palladium (0.45g,0.4mmol) when the temperature rises to 40 ℃, heating to reflux for reaction for 5h, cooling the reaction solution to room temperature after the reaction is completed, extracting with 200mL of toluene, washing with 400mL of ultrapure water, drying with anhydrous sodium sulfate, concentrating until no liquid flows out, purifying the product by a column, and using petroleum ether and ethyl acetate as a eluent (4: 1, volume ratio), intermediate A-1(8.15g, yield 30%) was obtained.
2. The intermediates A-I listed in Table 6 were synthesized by referring to the procedure for the intermediate A-1, except that the starting material A was used in place of 2, 4-dichloro-6-naphthalen-2-yl- [1,3,5] triazine and the starting material B was used in place of dibenzofuran-2-boronic acid, and the structures of the main starting material, the intermediates A-I and the yields thereof are shown in Table 6.
TABLE 6
Synthesis example 19: synthesis of Compound 12
Adding an intermediate C-4(10.55g,37mmol) and 100mL of DMF (dimethyl formamide) into a 500mL three-necked flask, introducing nitrogen for protection, starting stirring, cooling to 5-10 ℃, adding NaH (1.15g,48mmol), dissolving an intermediate a-12(14.95g,37mmol) with 40mL of DMF, dropwise adding into a reaction system, reacting for 5 hours, filtering after the reaction is finished, pulping with 60mL of acetone, separating a product through a column, and obtaining a compound 12(10.87g, yield 45%) by using petroleum ether and ethyl acetate (6: 1, volume ratio): 657.18[ M + H ] M/z]+。
Synthesis examples 20 to 28
The compounds of table 6 were synthesized with reference to the synthesis of compound 12, except that intermediate C-I was used instead of intermediate C-4, and starting material IV (including a-I) was used instead of intermediate a-12, and the main starting materials, compounds and their structures, yields and mass spectrometry characterization structures used are shown in table 6.
TABLE 6
Preparation and evaluation of organic electroluminescent device
Example 1: green organic electroluminescent device
The anode was prepared by the following procedure: will have a thickness of
The ITO substrate (manufactured by Corning) of (1) was cut into a size of 40mm × 40mm × 0.7mm, prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern using a photolithography process, using ultraviolet ozone and O2:N2The plasma was surface treated to increase the work function of the anode (experimental substrate) and to remove scum.
F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness of
And NPB is vapor-deposited on the hole injection layer to form a layer having a thickness of
The hole transport layer of (1).
Vacuum evaporating compound HT-1 on the hole transport layer to a thickness of
The hole adjusting layer of (1).
On the hole-adjusting layer, compound 1: GH-N1: ir (ppy)3The mixture is evaporated at a thickness ratio of 45 percent to 10 percent to form a film with a thickness of
The green light emitting layer of (2).
ET-1 and LiQ were formed by vapor deposition at a film thickness ratio of 1:1
A thick electron transport layer formed by vapor depositing Yb on the electron transport layer
Then magnesium (Mg) and silver (Ag) were vacuum-evaporated on the electron injection layer at a film thickness ratio of 1: 9 to form a layer having a thickness of
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Example 2 example 28
An organic electroluminescent device was produced in the same manner as in example 1, except that in the formation of the light-emitting layer, compounds shown in table 8 below were used instead of compound 1.
Comparative example 1 to comparative example 4
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a, compound B, compound C, and compound D in table 8 below were each substituted for compound 1 in forming a light-emitting layer.
The structures of the main materials used in examples 1 to 28 and comparative examples 1 to 4 are shown in Table 7.
TABLE 7
For the organic electroluminescent devices prepared in the above examples and comparative examples, at 20mA/cm2Conditions of (2)The device was analyzed and the results are shown in Table 8.
TABLE 8
From the results of table 8, it can be seen that the organic electroluminescent devices of examples 1 to 28 using the nitrogen-containing compounds of the present application as the organic light-emitting layer have a driving voltage reduced by at least 0.24V, a luminous efficiency (Cd/a) increased by at least 12.6%, and an external quantum efficiency (EQE/%) increased by at least 12.7% as compared to the devices of comparative examples 1 to 4 using known compounds as the organic light-emitting layer; it can be seen that the nitrogen-containing compounds used in examples 1 to 28 can further improve the photoelectric efficiency of the device and reduce the driving voltage of the device. In addition, the nitrogen-containing compounds used in examples 1 to 28 can also provide higher yield of the organic electroluminescent device, for example, the lifetime can be increased by more than 21.4%, and can be increased by more than 75h at most.
The preferred embodiments of the present disclosure are described in detail with reference to the accompanying drawings, however, the present disclosure is not limited to the specific details of the embodiments, and various simple modifications may be made to the technical solution of the present disclosure within the technical idea of the present disclosure, and these simple modifications all belong to the protection scope of the present disclosure.
It should be noted that, in the foregoing embodiments, various 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 in the present application.
In addition, any combination of the various embodiments of the present application is also possible, and the same should be considered as disclosed in the present application as long as it does not depart from the idea of the present application.
Claims (13)
1. A nitrogen-containing compound, wherein the structure of the nitrogen-containing compound is represented by formula I:
wherein, X1、X2、X3Are identical or different from each other, are each independently selected from N or CH, and at least one is N;
Ar1and Ar2The same or different from each other, each is independently selected from substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L、L1and L2The same or different from each other, each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;
y is selected from C (R)1R2)、Si(R1R2) O, S or N (R)3)；R1、R2And R3The same or different from each other, and each is independently selected from an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, and an aryl group having 6 to 15 carbon atoms; optionally, R1And R2Form a ring together with the atoms to which they are commonly attached;
Ar1and Ar2Wherein the substituents are the same or different from each other and are each independently selected from deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triarylsilyl group having 18 to 24 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an arylthio group having 6 to 18 carbon atoms, and optionally, any two adjacent substituents form a ring;
L、L1、L2wherein the substituents are the same as each other orDifferent and independently selected from deuterium, a halogen group, cyano, phenyl, naphthyl, pyridyl, trialkylsilyl having 3-7 carbon atoms, alkyl having 1-4 carbon atoms, haloalkyl having 1-4 carbon atoms, cycloalkyl having 5-10 carbon atoms, alkoxy having 1-4 carbon atoms and alkylthio having 1-4 carbon atoms;
Ra、Rband RcIdentical or different from each other and each independently selected from deuterium, a halogen group, a cyano group, a group A, a trialkylsilyl group having 3 to 7 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms; the group A is selected from substituted or unsubstituted aryl with 6-15 carbon atoms or substituted or unsubstituted heteroaryl with 4-10 carbon atoms, and the substituent in the group A is selected from deuterium, fluorine, cyano and alkyl with 1-4 carbon atoms;
na、nband ncEach represents Ra、RbAnd RcThe number of (2); n isaSelected from 0, 1,2, 3 or 4, when n isaWhen greater than 1, any two RaThe same or different; n isbSelected from 0, 1 or 2, when nbWhen it is 2, two RbThe same or different; n iscSelected from 0, 1,2, 3 or 4, when n iscWhen greater than 1, any two RcThe same or different.
2. The nitrogen-containing compound according to claim 1, wherein L, L1、L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 15 carbon atoms;
preferably, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 6 to 12 carbon atoms;
preferably, L1、L2Each independently selected from a single bond, and a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
3. The nitrogen-containing compound according to claim 1, wherein L, L1、L2Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a new subunit group formed by interconnecting a phenylene group and a naphthylene group;
preferably L, L1、L2Wherein the substituents in (A) are independently selected from deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, trifluoromethyl and phenyl;
preferably, L1、L2Each independently selected from a single bond, substituted or unsubstituted phenylene.
4. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2The same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 20 carbon atoms.
5. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2Each substituent in (a) is independently selected from: deuterium, fluorine, cyano, alkyl having 1 to 4 carbon atoms, heteroaryl having 5 to 12 carbon atoms, aryl having 6 to 15 carbon atoms, trialkylsilyl having 3 to 7 carbon atoms, haloalkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms.
6. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2Are identical or different and are each independently selected from substituted or unsubstituted radicals V1Unsubstituted radicals V1Selected from the group consisting of:
substituted radicals V1Wherein the substituent group is independently selected from deuterium, fluorine, cyano, alkyl group having 1 to 4 carbon atoms, trifluoromethyl, cycloalkyl group having 5 to 10 carbon atoms, trialkylsilyl group having 3 to 7 carbon atoms, and phenyl; when the number of the substituents is more than 1, the substituents may be the same or different.
7. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1And Ar2Each independently selected from the group consisting of:
8. the nitrogen-containing compound according to claim 1, wherein R1、R2And R3The same or different, and each is independently selected from alkyl with 1-4 carbon atoms and aryl with 6-12 carbon atoms; optionally, R1And R2Form a ring together with the atoms to which they are commonly attached;
preferably, R1、R2Each independently selected from methyl or phenyl, R3Selected from phenyl, naphthyl and biphenyl.
9. The nitrogen-containing compound according to claim 1, wherein n isa、nbAnd ncEach independently selected from 0 or 1;
preferably, Ra、RbAnd RcEach independently selected from deuterium, fluoro, cyano, phenyl, biphenyl, naphthyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, fluoromethyl, cyclopentyl, cyclohexyl, pyridyl, fluoro-substituted phenyl, deuterium-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl.
10. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
11. an organic electroluminescent device, comprising an anode and a cathode which are oppositely arranged, and a functional layer which is arranged between the anode and the cathode; the functional layer contains the nitrogen-containing compound according to any one of claims 1 to 10.
12. The organic electroluminescent device according to claim 11, wherein the functional layer comprises an organic light-emitting layer containing a host material containing the nitrogen-containing compound and a guest material;
preferably, the organic electroluminescent device is a green device.
13. An electronic device comprising the organic electroluminescent element according to claim 11 or 12.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20110113469A (en) * | 2010-04-09 | 2011-10-17 | 에스에프씨 주식회사 | Heterocyclic compounds and organic light-emitting diode including the same |
| CN111518106A (en) * | 2014-04-09 | 2020-08-11 | 斗山索如始株式会社 | Organic compound and organic electroluminescent element comprising same |
| KR20160060572A (en) * | 2014-11-19 | 2016-05-30 | 주식회사 엠비케이 | Organic electroluminescent compound, ink composition, organic electroluminescent device and electric apparatus |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114292278A (en) * | 2021-09-24 | 2022-04-08 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
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| CN112876455B (en) | 2022-08-30 |
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