CN114075179B - Nitrogen-containing compound, organic electroluminescent device using same and electronic device - Google Patents
Nitrogen-containing compound, organic electroluminescent device using same and electronic device Download PDFInfo
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- CN114075179B CN114075179B CN202110729761.0A CN202110729761A CN114075179B CN 114075179 B CN114075179 B CN 114075179B CN 202110729761 A CN202110729761 A CN 202110729761A CN 114075179 B CN114075179 B CN 114075179B
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- carbon atoms
- nitrogen
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 152
- 239000010410 layer Substances 0.000 claims description 76
- 125000001424 substituent group Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 229910052805 deuterium Inorganic materials 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 239000002346 layers by function Substances 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000005561 phenanthryl group Chemical group 0.000 claims description 8
- 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 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 125000004653 anthracenylene group Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 3
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 38
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 238000002347 injection Methods 0.000 abstract description 18
- 239000007924 injection Substances 0.000 abstract description 18
- 230000005540 biological transmission Effects 0.000 abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 230000005525 hole transport Effects 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- 229910021642 ultra pure water Inorganic materials 0.000 description 9
- 239000012498 ultrapure water Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 3
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 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 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001343 alkyl silanes Chemical class 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 150000001716 carbazoles Chemical group 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001975 deuterium Chemical group 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FRYRJNHMRVINIZ-UHFFFAOYSA-N B1CCOO1 Chemical compound B1CCOO1 FRYRJNHMRVINIZ-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 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
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
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- 230000005494 condensation Effects 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
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000002349 favourable effect Effects 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
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 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
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 238000000206 photolithography Methods 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
- 125000005592 polycycloalkyl group 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
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930192474 thiophene Natural products 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000008096 xylene Substances 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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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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Abstract
The present application relates to a nitrogen-containing compound, and an organic electroluminescent device and an electronic device using the same. Wherein the nitrogen-containing compound is selected from the group consisting of compounds represented by formula 1. When the nitrogen-containing compound is used for an organic electroluminescent layer electronic type main material of an organic electroluminescent device, the electron transmission performance of the device is effectively improved, so that the balance degree of hole injection and electron injection is enhanced, and the luminous efficiency and the service life of the device are improved.
Description
Technical Field
The present application relates to the technical field of organic electroluminescence, and in particular, to a nitrogen-containing compound, and an organic electroluminescent device and an electronic device using the same.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Such electronic components typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of organic or inorganic film layers and generally includes an 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, it generally includes 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 cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards in the prior art.
This is also investigated in the prior art documents, for example: patent documents KR2016070295A, WO2017160089A1, KR2020025939A, KR2017068931A, KR1020130074765A, KR1020200125080a, etc., disclose that a light-emitting host material can be prepared in an organic electroluminescent device. However, there remains a need to continue to develop new materials to further improve the performance of electronic components.
Disclosure of Invention
The purpose of the application is to provide a nitrogen-containing compound, and an organic electroluminescent device and an electronic device using the same, which have high luminous efficiency and service life.
In order to achieve the above object, a first aspect of the present application provides a nitrogen-containing compound having a structure represented by the following formula 1:
wherein ,Ar1 and Ar2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
Ar 3 a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
each R is 1 and R2 Each independently selected from deuterium, halogen group, cyano, aryl group having 6-20 carbon atoms, heteroaryl group having 3-20 carbon atoms, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, heterocycloalkyl group having 2-10 carbon atoms;
n 1 R represents 1 And n is the number of 1 Selected from 0, 1, 2, 3, 4, 5 or 6, and when n 1 When the number is greater than 1, any two R 1 The same or different from each other;
n 2 r represents 2 And n is the number of 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, and when n 2 When the number is greater than 1, any two R 2 The same or different from each other;
L、L 1 、L 2 and L3 Independently selected from single bond, C6-30A substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 、Ar 3 、L、L 1 、L 2 and L3 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triarylsilyl group having 18 to 24 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylthio group having 6 to 18 carbon atoms, phosphinoxy group having 6 to 18 carbon atoms;
optionally in Ar 1 、Ar 2 and Ar3 Any two adjacent substituents form a ring.
A second aspect of the present application provides an organic electroluminescent device, including an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises a nitrogen-containing compound as described in the first aspect of the present application.
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.
Through the technical scheme, carbazole, dibenzofuran and triazine are used as core groups, the nitrogen-containing compound contains electron-deficient triazine groups, the electron injection and transmission capacity of the material can be effectively improved, and the dibenzofuran is connected with the No. 4 carbazole, so that the material has a higher T1 (triplet energy level) in a specific connection mode, the material molecule has a more three-dimensional space structure, and the material molecule is favorable for the transmission of carriers and energy. Secondly, when the nitrogen-containing compound is used for the electron-type main body material of the luminous layer of the organic electroluminescent device, the electron transmission performance of the device is effectively improved, so that the balance degree of hole injection and electron injection is enhanced, and the luminous efficiency and the service life of the device are improved.
Additional features and advantages of the present application will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application. In the 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 electroluminescent layer; 340. a hole blocking layer; 350. an electron transport layer; 360. an electron injection layer; 400. an electronic device.
Detailed Description
The following detailed description of specific embodiments of the present application refers to the accompanying drawings. It should be understood that the detailed description is presented herein for purposes of illustration and explanation only and is not intended to limit the present application.
A first aspect of the present application provides a nitrogen-containing compound having a structure represented by the following formula 1:
wherein ,Ar1 and Ar2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms;
Ar 3 a substituted or unsubstituted aryl group having 6 to 30 carbon atoms;
each R is 1 and R2 Independently selected from deuterium, halogen group, cyano group, aryl group with 6-20 carbon atoms, and carbon atom Heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, heterocycloalkyl having 2 to 10 carbon atoms;
n 1 r represents 1 And n is the number of 1 Selected from 0, 1, 2, 3, 4, 5 or 6, and when n 1 When the number is greater than 1, any two R 1 The same or different from each other;
n 2 r represents 2 And n is the number of 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, and when n 2 When the number is greater than 1, any two R 2 The same or different from each other;
L、L 1 、L 2 and L3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar 1 、Ar 2 、Ar 3 、L、L 1 、L 2 and L3 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triarylsilyl group having 18 to 24 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylthio group having 6 to 18 carbon atoms, phosphinoxy group having 6 to 18 carbon atoms;
Optionally in Ar 1 、Ar 2 and Ar3 Any two adjacent substituents form a ring.
In the present application, R 1 、R 2 、Ar 1 、Ar 2 、Ar 3 、L、L 1 、L 2 and L3 Refers to all carbon number. For example, if L 1 Selected from the group consisting of substituted arylene groups having 10 carbon atoms, the sum of all carbon atoms of the arylene groups and substituents thereon is 10. For example, if Ar 1 Is 9, 9-dimethylFluorenyl group, ar 1 Substituted fluorenyl with 15 carbon atoms, ar 1 The number of ring-forming carbon atoms is 13.
In the present specification, the terms "substituted or unsubstituted aryl group having 6 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 30 carbon atoms" are the same in meaning, and refer to the aryl group and the substituents thereon having 6 to 30 total carbon atoms. Similarly, in the present specification, the terms "a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms" and "a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms" are the same, and refer to both the heteroaryl group and the substituents thereon having 3 to 30 total carbon atoms.
The term "optionally" or "optionally" means that the subsequently described event or circumstance may occur, but is not necessarily the case, and that the description includes instances where the event or circumstance occurs or does not. For example, "a heterocyclic group optionally substituted with an alkyl group" means that an alkyl group may be, but is not necessarily, present, and the description includes situations where the heterocyclic group is substituted with an alkyl group and situations where the heterocyclic group is not substituted with an alkyl group. "optionally, rv2 and Rv3 linked to the same atom are linked to each other to form a saturated or unsaturated ring" means that Rv2 and Rv3 linked to the same atom may be but need not be looped, and this scheme includes a scenario in which Rv2 and Rv3 are linked to each other to form a loop, and also includes a scenario in which Rv2 and Rv3 exist independently of each other.
In the present application, "any two adjacent substituents form a ring," any two adjacent "may include two substituents on the same atom, and may include two adjacent atoms each having one substituent; wherein when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring. For example, when Ar 1 When there are 2 or more substituents and any adjacent substituents form a ring, the ring formed is a saturated ring or an unsaturated ring, and the number of carbon atoms is 5 to 13, for example: fluorene ring, benzene ring, naphthalene ring, cyclopentane, cyclohexane,Adamantane, and the like.
The descriptions used in this application, "each … … is independently" and "… … is each independently" and "… … is independently selected from" being interchangeable, and should be understood in a broad sense to mean that the specific options expressed between the same symbols in different groups do not affect each other, or that the specific options expressed between the same symbols in the same groups do not affect each other.
For example: in'
Wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from the group consisting of hydrogen, fluorine, chlorine" and has the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, "hetero" means that at least 1 heteroatom such as B, N, O, S, se, si or P is included in one functional group and the remaining atoms are carbon and hydrogen when no specific definition is provided otherwise.
In the present application, the term "substituted or unsubstituted" means that the functional group described later in the term may have a substituent or not. For example, "substituted or unsubstituted aryl" refers to an alkyl group having a substituent or an unsubstituted aryl group. "substituted" means that it may be substituted with a substituent selected from the group consisting of: deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triarylsilyl group having 18 to 24 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylthio group having 6 to 18 carbon atoms, phosphinoxy group having 6 to 18 carbon atoms.
In this application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 10 carbon atoms, in this application, a numerical range such as "1 to 10" refers to each integer in the given range; for example, "1 to 10 carbon atoms" refers to an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms. The alkyl group may be optionally substituted with one or more substituents described herein. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH 3 ) Ethyl (Et, -CH) 2 CH 3 ) N-propyl (n-Pr, -CH) 2 CH 2 CH 3 ) Isopropyl (i-Pr, -CH (CH) 3 ) 2 ) N-butyl (n-Bu, -CH) 2 CH 2 CH 2 CH 3 ) Isobutyl (i-Bu, -CH) 2 CH(CH 3 ) 2 ) Sec-butyl (s-Bu, -CH (CH) 3 )CH 2 CH 3 ) Tert-butyl (t-Bu, -C (CH) 3 ) 3 ) Etc. Furthermore, alkyl groups may be substituted or unsubstituted.
Cycloalkyl in this application refers to cyclic saturated hydrocarbons, including monocyclic and polycyclic structures. Cycloalkyl groups may have 3-10 carbon atoms, for example, "3 to 10 carbon atoms" refers to cycloalkyl groups that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms. For example, examples of cycloalkyl groups may be, but are not limited to: five membered cycloalkyl groups, i.e., cyclopentyl, six membered cycloalkyl groups, i.e., cyclohexyl, 10 membered polycycloalkyl groups, such as adamantyl, and the like.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two connected by a carbon-carbon bond conjugateOne or more fused ring aryl groups. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein. Wherein the aryl does not contain B, N, O, S, se, si or P heteroatoms. For example, in the present application, phenyl, biphenyl, terphenyl, and the like are aryl groups. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, perylene, benzofluoranthenyl,
Radical, 9-dimethylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, indenyl, and the like, without limitation thereto.
The "substituted or unsubstituted aryl" herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 25, in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 20, and in other embodiments the number of carbon atoms in the substituted or unsubstituted aryl may be from 6 to 13. In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 18, 20, 25 or 30, but of course, the number of carbon atoms may be other numbers, which are not listed here.
In this application, substituted aryl refers to an aryl in which one or more hydrogen atoms are replaced with other groups. For example, at least one hydrogen atom is substituted with a deuterium atom, F, cl, I, CN, hydroxyl, branched alkyl, straight chain alkyl, haloalkyl, cycloalkyl, alkoxy, alkylthio, aryl, heteroaryl, alkylsilyl, arylsilyl, or other group. 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 substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms refers to an aryl group and 18 total carbon atoms of the substituents on the aryl group. For example, 9-dimethylfluorenyl is a substituted aryl group having 15 carbon atoms.
In the present application, a fluorenyl group as an aryl group may be substituted, and two substituents may be combined with each other to form a spiro structure, specific examples include, but are not limited to, the following structures:
in the present application, heteroaryl may be heteroaryl comprising 1, 2, 3, 4, 5 or 6 heteroatoms selected from B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring, and either aromatic ring system containing the heteroatoms. Illustratively, heteroaryl groups may include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, dibenzothienyl, dibenzofuranyl, quinolinyl, isoquinolinyl, phenanthrolinyl, and the like.
The "substituted or unsubstituted heteroaryl" of this application may contain 3 to 30 carbon atoms, and in some embodiments the substituted or unsubstituted heteroaryl is a heteroaryl having 5 to 20 carbon atoms, in other embodiments the substituted or unsubstituted heteroaryl is a heteroaryl having 5 to 18 carbon atoms, and in other embodiments the substituted or unsubstituted heteroaryl is a heteroaryl having 5 to 12 carbon atoms. In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30, although the number of carbon atoms may be other, and is not specifically recited herein.
In the present application, substituted heteroaryl means that one or more hydrogen atoms in the heteroaryl is substituted with a group thereof, for example, at least one hydrogen atom is substituted with a deuterium atom, F, cl, br, -CN, alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, aryloxy, arylthio, silyl, phosphinoxy or other group.
In the present application, the explanation for aryl group may be applied to arylene group, the explanation for heteroaryl group may be applied to heteroarylene group, the explanation for alkyl group may be applied to alkylene group, and the explanation for cycloalkyl group may be applied to cycloalkylene group.
"Ring" in the present application includes saturated rings and unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl; unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl.
In the present application alkylsilane refers to
wherein ,RG1 、R G2 、R G3 Specific examples of alkyl groups, alkylsilane groups, each independently, include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, propyldimethylsilyl.
The term "non-aligned connection" as used herein refers to a single bond extending from a ring system
It means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
For example, the naphthyl group represented by formula (f) is linked to the other positions of the molecule via two non-positional linkages extending through the bicyclic ring, which means includes any of the possible linkages shown in formulas (f-1) to (f-10).
As another example, the phenanthryl group represented by the following formula (X ') is linked to the other position of the molecule through an unoriented linkage extending from the middle of one benzene ring, and the meaning of the linkage includes any possible linkage as shown in the formulas (X ' -1) to (X ' -4).
An delocalized substituent in this application refers to a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, the substituent R represented by the following formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by this linkage includes any one of the possible linkages represented by the formulae (Y-1) to (Y-7).
The meaning of the non-positional connection or the non-positional substitution is the same as here, and will not be described in detail later.
In the present application, the haloalkyl group having 1 to 10 carbon atoms may have, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 carbon atoms, including, but not limited to, trifluoromethyl and the like.
In the present application, the alkoxy group having 1 to 10 carbon atoms may be a chain, cyclic or branched alkoxy group. The number of carbon atoms may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, including but not limited to methoxy, isopropoxy, and the like.
In the present application, a trialkylsilyl group having 3 to 12 carbon atoms. The number of carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, including but not limited to trimethylsilyl, and the like.
In the present application, the halogen group may be selected from fluorine, chlorine, bromine, iodine.
In the present application, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms is selected from the group consisting of substituted or unsubstituted: phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, anthracyl, phenanthryl, perylenyl, pyrenyl, and the like.
In some embodiments of the present application, L is selected from a single bond, phenylene, naphthylene, or biphenylene.
In some embodiments of the present application, L is selected from the group consisting of a single bond or:
in some embodiments of the present application, L 1 、L 2 and L3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
Alternatively, L 1 、L 2 and L3 The substituents in (2) are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms or phenyl.
Specifically, L 1 、L 2 and L3 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
In other embodiments of the present application, L 1 、L 2 and L3 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group.
Alternatively, L 1 、L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazole group.
Alternatively, L 3 Selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, and a substituted or unsubstituted phenanthrylene group.
In some embodiments of the present application, L 1 、L 2 Independently selected from a single bond or a substituted or unsubstituted group G selected from the group consisting ofThe group:
wherein ,
represents a chemical bond; the substituted group G contains one or more substituents which are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl and naphthyl; when the substituted group G contains a plurality of substituents, the substituents may be the same or different.
Alternatively, L 1 、L 2 Each independently selected from the group consisting of a single bond or the following groups;
in some embodiments of the present application, L 3 Selected from single bonds, substituted or unsubstituted groups T, unsubstituted groups T being selected from the group consisting of:
wherein ,
represents a chemical bond; the substituted group T contains one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, T-butyl, phenyl or naphthyl; when the substituted group T contains a plurality of substituents, the substituents may be the same or different.
Alternatively, L 3 Selected from the group consisting of single bonds or:
in some embodiments of the present application, ar 1 and Ar2 Each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 20 carbon atoms.
Alternatively, ar 1 and Ar2 The substituents in (2) are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms and aryl with 6-12 carbon atoms;
optionally in Ar 1 and Ar2 Any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms. For example, in Ar 2 Any two adjacent substituents form a cyclopentane, cyclohexane, adamantane, benzene ring, naphthalene ring or fluorene ring
Etc.
Specifically, ar 1 and Ar2 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, naphthyl.
Optionally in Ar 1 and Ar2 Any two adjacent substituents form a fluorene ring
Etc.
In other embodiments of the present application, ar 1 and Ar2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl.
In some embodiments of the present application, ar 1 and Ar2 Identical or different and are each independently selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
wherein ,
represents a chemical bond; the substituted group V contains one or more substituents which are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl and naphthyl; when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
Alternatively, ar 1 and Ar2 Each independently selected from the group consisting of:
In some embodiments of the present application, ar 3 Selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms.
Alternatively, ar 3 The substituent of (C) is selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms, and phenyl.
Optionally in Ar 3 Any two adjacent substituents form a saturated or unsaturated ring with 5-13 carbon atoms. For example, in Ar 2 Any two adjacent substituents form a cyclopentane, cyclohexane, adamantane, benzene ring, naphthalene ring or fluorene ring
Etc.
Specifically, the Ar 3 Specific examples of substituents in (a) include, but are not limited to: deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl.
Optionally in Ar 3 Any two adjacent substituents form a fluorene ring
Further alternatively, ar 3 Selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.
In some embodiments of the present application, ar 3 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted triphenylene, substituted or unsubstituted terphenyl, and substituted or unsubstituted fluorenyl.
In some embodiments of the present application, ar 3 Selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:
wherein ,
represents a chemical bond; the substituted group W contains one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl; when the substituted group W contains a plurality of substituents, the substituents may be the same or different.
Alternatively, ar 3 Selected from the group consisting of:
in some embodiments of the present application, n 1 and n2 Each 0.
In some embodiments of the present application, the nitrogen-containing compound is selected from the group consisting of:
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 as described in the first aspect of the present application.
For example, as shown in fig. 1, the organic electroluminescent device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 contains the nitrogen-containing compound provided in the first aspect of the present application.
According to one embodiment, the organic electroluminescent device may be, for example, a green organic electroluminescent device.
In one embodiment of the present application, the functional layer 300 includes an organic electroluminescent layer including the nitrogen-containing compound.
In one embodiment, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an organic electroluminescent layer 330, an electron transport layer 350, and a cathode 200, which are sequentially stacked, wherein the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322.
In one embodiment, anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. The anode material specifically comprises: 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 such as ZnO: al and SnO 2 : sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. Also preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
In one embodiment, the first hole transport layer 321 may include one or more hole transport materials, and the first hole transport layer material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, which are not particularly limited herein. Specifically, the first hole transport layer 321 is composed of a compound NPB.
In one embodiment, second hole transport layer 322 may include one or more hole transport materials, which may be selected from carbazole multimers or other types of compounds, as not particularly limited herein. In one embodiment, second hole transport layer 322 is composed of compound HT-02.
In this application, the electron transport layer 350 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials further include a material selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which are not particularly limited herein. For example, in one embodiment of the present application, electron transport layer 350 may be composed of ET-01 and LiQ together.
In one embodiment, the organic electroluminescent layer 330 may be composed of a single light emitting material, or may be composed of a host material and a guest material. Preferably, the organic electroluminescent layer 330 is composed of a host material and a guest material, and holes injected into the organic electroluminescent layer 330 and electrons injected into the organic electroluminescent layer 330 may be combined at the organic electroluminescent layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic electroluminescent layer 330 may be a nitrogen-containing compound of the present application, or may be composed of a nitrogen-containing compound of the present application together with other light-emitting host materials, such as a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in the present application. In one embodiment, the host material of the organic electroluminescent layer 330 is composed of a nitrogen-containing compound and GH-p1 together.
The guest material of the organic electroluminescent layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited herein. In one embodiment of the present application, the guest material of the organic electroluminescent layer 330 is Ir (ppy) 2 (acac)。
In one embodiment, the cathode 200 includes a cathode material that is a material with a small work function that facilitates electron injection into the functional layer. In particular, specific examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, and aluminumSilver, tin and lead or alloys thereof; multilayer materials such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 /Ca, but is not limited thereto. Preferably, a metal electrode comprising silver and magnesium is included as a cathode.
In this application, as shown in fig. 1, a hole injection layer 310 may be further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. In one embodiment of the present application, hole injection layer 310 may be composed of HAT-CN.
In one embodiment, as shown in fig. 1, an electron injection layer 360 may also be provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. Specifically, the electron injection layer 360 may include LiQ.
In one embodiment, a hole blocking layer 340 may be further disposed between the organic electroluminescent layer 330 and the electron transport layer 350.
A third aspect of the present application provides an electronic device comprising the organic electroluminescent device provided in the second aspect of the present application. Since the electronic device has any one of the organic electroluminescent devices described in the embodiments of the organic electroluminescent device, the electronic device has the same beneficial effects, and the application is not repeated here.
For example, as shown in fig. 2, one embodiment of the present application provides an electronic device 400. The electronic device 400 includes the organic electroluminescent device in the above embodiment. An organic electroluminescent device as described in any one of the embodiments. The electronic device 400 may be a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The present application is further illustrated by the following examples, but is not limited thereby.
The synthesis method of the provided nitrogen-containing compound is not particularly limited in this application, and a person skilled in the art can determine a suitable synthesis method from the preparation method provided in the section of the preparation example of the nitrogen-containing compound of this application. All of the nitrogen-containing compounds provided herein may be obtained by one skilled in the art from these exemplary methods of preparation, and all specific methods of preparation for such nitrogen-containing compounds are not described in detail herein and should not be construed as limiting the present application.
Synthesis of intermediate G-1
To a 1000mL three-necked flask equipped with nitrogen protection and a condensate reflux apparatus were added o-bromoiodobenzene (28.29 g,100 mmol), dibenzofuran-3-borate (21.20 g,100 mmol), potassium carbonate (27.64 g,200 mmol), tetrabutylammonium bromide (3.22 g,10 mmol), toluene (240 mL), ethanol (60 mL), and ultrapure water (60 mL); introducing nitrogen for protection, starting heating and stirring, and adding tetraphenylphosphine palladium (1.15 g,1 mmol) when the temperature rises to 40 ℃; heating and refluxing, reacting for 16 hours, cooling the reaction liquid to room temperature after the reaction is finished, separating liquid, extracting the water phase by using 150mL of toluene, merging organic phases, washing the organic phases with ultrapure water for 3 times, 200mL each time, merging the organic phases and drying by using anhydrous sodium sulfate; after concentration, separating the product by silica gel column chromatography, wherein the eluent is petroleum ether: ethyl acetate (6:1 by volume) to afford intermediate E-1 (22.62 g, 70% yield).
To a 1000mL three-necked flask equipped with a nitrogen protection and a condensate reflux apparatus were added intermediate E-1 (32.32 g,100 mmol), 2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan) -5-chloro-nitrobenzene (28.35 g,100 mmol), potassium carbonate (27.64 g,200 mmol), tetrabutylammonium bromide (3.22 g,10 mmol), toluene (300 mL), ethanol (60 mL), and ultrapure water (60 mL); introducing nitrogen for protection, starting heating and stirring, and adding tetraphenylphosphine palladium (1.15 g,1 mmol) when the temperature rises to 40 ℃; heating and refluxing, reacting for 30 hours, cooling the reaction liquid to room temperature after the reaction is finished, separating liquid, extracting the water phase by using 200mL of toluene, merging organic phases, washing the organic phases by using ultrapure water for 3 times, and merging the organic phases by using 200mL of anhydrous sodium sulfate each time, and drying; after concentration, separating the product by silica gel column chromatography, wherein the eluent is n-heptane: dichloromethane (volume ratio 3:1); intermediate F-1 (21.99 g, yield 55%) was obtained.
To a 1000mL three-necked flask equipped with a nitrogen protection and a condensate reflux apparatus were added intermediate F-1 (39.98 g,100 mmol), triphenylphosphine (52.46 g,200 mmol), o-dichlorobenzene (600 mL); introducing nitrogen for protection, starting heating and stirring, heating to reflux, reacting for 12 hours, completely evaporating out the reaction solvent after the reaction is completed, separating the product by column chromatography, and eluting with n-heptane: dichloromethane (volume ratio 2:1) to intermediate G-1 (14.71G, 40% yield).
Synthesis of intermediates G-2 to G-4
The intermediates shown in Table 1 were synthesized with reference to the synthesis method of intermediate G-1, except that starting material 1 was used in place of dibenzofuran 3-borate to prepare the intermediates shown in Table 1 below.
TABLE 1
Synthesis example 1 Synthesis of Compound Aa1
Into a 1000mL three-necked flask equipped with a nitrogen protection and a condensation reflux apparatus, an intermediate G-1 (36.78G, 100 mmol), iodobenzene (20.4G, 100 mmol) and xylene (350 mL) were charged, nitrogen protection was introduced, stirring and heating were turned on, and when the temperature rose to 40 ℃, sodium tert-butoxide (14.4G, 150 mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxy-biphenyl (s-phos) (0.82G, 2 mmol), tris (dibenzylideneacetone) dipalladium (Pd) were sequentially added 2 (dba) 3 ) (0.91 g,1 mmol); heating to reflux, reacting for 5h, stopping stirring and heating after the reaction is completed, and starting to treat the reaction when the temperature is reduced to room temperature; adding 100mL of ultrapure water into the reaction solution, stirring and separating, extracting the water phase twice with 100mL of toluene each time, combining the organic phases, washing the organic phases with ultrapure water 3 times and 200mL each time, combining the organic phases and drying with anhydrous sodium sulfate; after concentration, the product was separated by silica gel column chromatography, the eluent was dichloromethane: n-heptane (volume ratio) =2: 3, intermediate H-1 (34.62 g, 78% yield) was obtained.
To a 1000mL three-necked flask equipped with nitrogen protection and a condensate reflux apparatus were added intermediate H-1 (22.21 g,50 mmol), pinacol biborate (15.23 g,60 mmol), potassium acetate (9.81 g,100 mmol), 1, 4-dioxane (220 mL); introducing nitrogen for protection, heating and stirring, and adding Pd when the temperature rises to 40deg.C 2 (dba) 3 (0.455 g,0.5 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (X-phos) (0.470 g,1 mmol); heating to reflux, reacting for 10 hours, cooling the reaction liquid to room temperature after the reaction is completed, adding 200mL of water, separating 200mL of toluene, extracting the water phase with 200mL of toluene, combining the organic phases, washing the organic phases with ultrapure water for 3 times, and drying with anhydrous sodium sulfate for 200mL each time; separating the product by silica gel column chromatography, wherein the eluent is n-heptane: dichloromethane (1:1 by volume) to afford intermediate I-1 (21.21 g, 80% yield).
To a 1000mL three-necked flask equipped with a nitrogen protection and a condensate reflux apparatus were added intermediate I-1 (26.77 g,50 mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (13.38 g,50 mmol), potassium carbonate (13.82 g,100 mmol), tetrabutylammonium bromide (1.61 g,5 mmol), toluene (250 mL), ethanol (60 mL), and ultrapure water (60 mL); introducing nitrogen for protection, starting heating and stirring, and adding tetraphenylphosphine palladium (0.57 g,0.5 mmol) when the temperature rises to 40 ℃; heating to reflux, reacting for 10 hours, cooling the reaction liquid to room temperature after the reaction is completed, separating liquid, extracting the water phase with 200mL of toluene, merging organic phases, washing the organic phases with ultrapure water for 3 times, 200mL each time, merging the organic phases, and drying with anhydrous sodium sulfate; after concentration, separating the product by silica gel column chromatography, wherein the eluent is n-heptane: dichloromethane (volume ratio 2:1) to give compound Aa1 (24.02 g, yield 75%), mass spectrometry: m/z=641.2 [ m+h ] ] + 。
Synthesis examples 2 to 21
The compounds shown in Table 2 were synthesized with reference to the synthesis method of the compound Aa1, except that raw material 2 (intermediates G-1 to G-4) was used in place of intermediate G-1, raw material 3 was used in place of iodobenzene, and raw material 4 was used in place of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, to prepare the compounds in Table 2 below.
TABLE 2
The nuclear magnetic data of the compound Ba1 are shown in table 3 below:
TABLE 3 Table 3
Preparation of organic electroluminescent device
Example 1: green organic electroluminescent device
The anode was prepared by the following procedure: an ITO substrate (manufactured by Corning) having a thickness of 150nm was cut into a size of 40 mm. Times.40 mm. Times.0.7 mm, and a test substrate having a pattern of a cathode, an anode and an insulating layer was prepared by a photolithography process using ultraviolet ozone and O 2 :N 2 The plasma was surface treated to increase the work function of the anode (experimental substrate) and to descum.
Vacuum vapor deposition of HAT-CN on experimental substrate (anode) to form a thickness of
Is deposited with NPB to form a Hole Injection Layer (HIL) having a thickness of +.>
Is provided. />
Vacuum evaporating HT-02 on the first hole transport layer to form a film having a thickness of
Is provided.
On the second hole transport layer, compound Aa1: GH-p1: ir (ppy) 2 (acac) at 50%:45%: co-evaporation is carried out at a ratio of 5% to form a film with a thickness of
Green organic electroluminescent layer (EML).
Mixing ET-01 and LiQ in a weight ratio of 1:1 and evaporating to form
A thick Electron Transport Layer (ETL), liQ is evaporated on the electron transport layer to form a thickness +.>
Electron Injection Layer (EIL) of (a), then magnesium (Mg) and silver (Ag) are mixed at 1:9, vacuum evaporating the electron injection layer to form a film having a thickness +.>
Is provided.
In addition, the thickness of the vapor deposited on the cathode is
An organic capping layer (CPL) is formed, thereby completing the fabrication of the organic light emitting device, the structure of which is shown in fig. 1.
Example 2-example 35
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound Aa1 was replaced with the compound shown in table 5 at the time of forming the light-emitting layer.
Comparative example 1
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound I was used instead of compound Aa1 when forming the organic electroluminescent layer.
Comparative example 2
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the following compound II was substituted for the compound Aa1 at the time of forming the organic electroluminescent layer.
Comparative example 3
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the following compound III was used instead of the compound Aa1 at the time of forming the organic electroluminescent layer.
The material structures used in the above examples and comparative examples are shown in table 4 below:
TABLE 4 Table 4
For the organic electroluminescent device prepared as above, the temperature was 20mA/cm 2 The device performance was analyzed under the conditions and the results are shown in table 5 below:
TABLE 5
Referring to the data in table 5, it can be seen that the compounds of examples 1 to 35 are used as electronic host materials in the green organic electroluminescent layer mixed host materials, and compared with the comparative examples, the compounds of this type significantly improve the luminous efficiency and the lifetime of the device. Wherein the device current efficiency is improved by at least 13.3% and the T95 lifetime is improved by at least 14.3% relative to comparative examples 1-3.
Therefore, when the nitrogen-containing compound is used for preparing the green organic electroluminescent device, the service life of the device can be effectively prolonged, and the luminous efficiency can be improved.
The preferred embodiments of the present application have been described in detail above with reference to the accompanying drawings, but the present application is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solutions of the present application within the scope of the technical concept of the present application, and all the simple modifications belong to the protection scope of the present application.
Claims (15)
1. A nitrogen-containing compound, characterized in that the nitrogen-containing compound has a structure represented by the following formula 1:
wherein ,Ar1 and Ar2 Each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl;
Ar 1 and Ar2 Wherein each substituent is independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, t-butyl, phenyl, naphthyl; optionally in Ar 1 and Ar2 Any two adjacent substituents form a fluorene ring;
Ar 3 selected from the group consisting of substituted or unsubstituted groups W selected from the group consisting of:
wherein ,
represents a chemical bond; the substituted group WContaining one or more substituents each independently selected from deuterium, fluoro, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl; when the substituted group W contains a plurality of substituents, the substituents are the same or different;
Each R is 1 and R2 Each independently selected from deuterium, halogen group, cyano, aryl group having 6-20 carbon atoms, heteroaryl group having 3-20 carbon atoms, alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, cycloalkyl group having 3-10 carbon atoms, heterocycloalkyl group having 2-10 carbon atoms;
n 1 r represents 1 And n is the number of 1 Selected from 0, 1, 2, 3, 4, 5 or 6, and when n 1 When the number is greater than 1, any two R 1 The same or different from each other;
n 2 r represents 2 And n is the number of 2 Selected from 0, 1, 2, 3, 4, 5, 6 or 7, and when n 2 When the number is greater than 1, any two R 2 The same or different from each other;
L、L 1 、L 2 and L3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
L、L 1 、L 2 and L3 The substituents in (a) are each independently selected from deuterium, halogen group, cyano group, heteroaryl group having 3 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, triarylsilyl group having 18 to 24 carbon atoms, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, heterocycloalkyl group having 2 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, aryloxy group having 6 to 18 carbon atoms, arylthio group having 6 to 18 carbon atoms, phosphinoxy group having 6 to 18 carbon atoms;
And the nitrogen-containing compound is not:
2. the nitrogen-containing compound according to claim 1, wherein L is selected from a single bond, phenylene, naphthylene, or biphenylene.
3. The nitrogen-containing compound according to claim 1, wherein L 1 、L 2 and L3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 20 carbon atoms.
4. A nitrogen-containing compound according to claim 3, wherein the L 1 、L 2 and L3 The substituents in (2) are independently selected from deuterium, halogen group, cyano, alkyl with 1-5 carbon atoms or phenyl.
5. The nitrogen-containing compound according to claim 1, wherein L 1 、L 2 and L3 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group.
6. The nitrogen-containing compound according to claim 5, wherein L 1 、L 2 and L3 The substituents of (2) are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl or phenyl.
7. The nitrogen-containing compound according to claim 1, wherein the Ar 1 and Ar2 Identical or different and are each independently selected from the group consisting of substituted or unsubstituted groups V selected from the group consisting of:
wherein ,
represents a chemical bond; the substituted group V contains one or more substituents which are independently selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl and naphthyl; when the substituted group V contains a plurality of substituents, the substituents may be the same or different.
8. The nitrogen-containing compound according to claim 1, wherein the Ar 3 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracyl, substituted or unsubstituted triphenylene, substituted or unsubstituted terphenyl, and substituted or unsubstituted fluorenyl.
9. The nitrogen-containing compound according to claim 8, wherein the Ar 3 The substituent of (a) is selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, tert-butyl and phenyl;
optionally in Ar 3 Any two adjacent substituents form a fluorene ring.
10. The nitrogen-containing compound according to claim 1, wherein the n 1 and n2 All 0.
11. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
12. an organic electroluminescent device, comprising an anode and a cathode which are arranged oppositely, and a functional layer arranged between the anode and the cathode; the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 11.
13. The organic electroluminescent device of claim 12, wherein the functional layer comprises an organic electroluminescent layer comprising the nitrogen-containing compound.
14. The organic electroluminescent device according to claim 12 or 13, wherein the organic electroluminescent device is a green organic electroluminescent device.
15. An electronic device comprising the organic electroluminescent device as claimed in any one of claims 12 to 14.
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| KR20240104319A (en) * | 2022-12-27 | 2024-07-05 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| CN106459018A (en) * | 2014-05-05 | 2017-02-22 | 默克专利有限公司 | Materials for organic light emitting devices |
| KR20170108894A (en) * | 2016-03-18 | 2017-09-27 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
| KR20180061076A (en) * | 2016-11-29 | 2018-06-07 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN112876462A (en) * | 2020-05-12 | 2021-06-01 | 陕西莱特光电材料股份有限公司 | Organic compound, and electronic element and electronic device using same |
| CN113637012A (en) * | 2020-05-11 | 2021-11-12 | 三星Sdi株式会社 | Compound for organic photoelectric device, composition for organic photoelectric device, and display device |
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| CN106459018A (en) * | 2014-05-05 | 2017-02-22 | 默克专利有限公司 | Materials for organic light emitting devices |
| KR20170108894A (en) * | 2016-03-18 | 2017-09-27 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
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| CN113637012A (en) * | 2020-05-11 | 2021-11-12 | 三星Sdi株式会社 | Compound for organic photoelectric device, composition for organic photoelectric device, and display device |
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