CN111892607B - N-heterobiphenyl organic compound and application thereof - Google Patents
N-heterobiphenyl organic compound and application thereof Download PDFInfo
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- CN111892607B CN111892607B CN202010869423.2A CN202010869423A CN111892607B CN 111892607 B CN111892607 B CN 111892607B CN 202010869423 A CN202010869423 A CN 202010869423A CN 111892607 B CN111892607 B CN 111892607B
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- aromatic
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 38
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 150000004982 aromatic amines Chemical class 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000005561 phenanthryl group Chemical group 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 125000001725 pyrenyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000005493 quinolyl group Chemical group 0.000 claims description 9
- 239000010409 thin film Substances 0.000 claims description 9
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 8
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 230000004927 fusion Effects 0.000 claims description 4
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 abstract description 34
- 239000000463 material Substances 0.000 abstract description 28
- 239000000969 carrier Substances 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 230000009477 glass transition Effects 0.000 abstract description 2
- 230000005012 migration Effects 0.000 abstract description 2
- 238000013508 migration Methods 0.000 abstract description 2
- 230000006798 recombination Effects 0.000 abstract description 2
- 238000005215 recombination Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 53
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 125000001041 indolyl group Chemical group 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 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 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 3
- 150000005041 phenanthrolines Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 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
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000004907 flux Effects 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
- 230000005484 gravity Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 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
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005406 washing Methods 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
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—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 four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/22—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 four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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- C—CHEMISTRY; METALLURGY
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Abstract
The invention provides an N-heterobiphenyl organic compound which has a structure shown in a formula I, a formula II or a formula III. The invention provides a series of compounds taking an N-heterobiphenyl structure as an electron accepting group, and the series of organic compounds are taken as main materials in an electroluminescent device and have higher triplet state energy level ETAnd the organic electroluminescent device has higher molecular density, higher glass transition temperature and molecular thermal stability, effectively improves the balance migration of carriers, widens an exciton recombination region, and effectively improves the light extraction efficiency, so that the luminous efficiency and the service life of the device are greatly improved, and the organic electroluminescent device can be well applied to the technical field of electroluminescent devices.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an N-heterobiphenyl organic compound and application thereof.
Background
Organic electroluminescent materials (OLEDs), as a new generation display technology, have the advantages of being ultra-thin, self-luminescent, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption, and the like, and have been widely used in the industries of flat panel display, flexible display, solid state lighting, vehicle-mounted display, and the like.
The light-emitting mechanism can be divided into two types, namely electroluminescence and electrophosphorescence. Fluorescence is the radiative decay transition of singlet excitons and phosphorescence is the light emitted by radiative decay of triplet excitons to the ground state. According to the spin quantum statistical theory, the formation probability ratio of singlet excitons to triplet excitons is 1: 3. The internal quantum efficiency of the fluorescent material is not more than 25 percent, and the external quantum efficiency is generally lower than 5 percent; the internal quantum efficiency of the electrophosphorescent material theoretically reaches 100%, and the external quantum efficiency reaches 20%. In 1998, the massecuite professor of Jilin university in China and the Forrest professor of Princeton university in USA respectively report that osmium complexes and platinum complexes are used as dyes to be doped into a light-emitting layer, the phosphorescence electroluminescence phenomenon is successfully obtained and explained for the first time, and the prepared phosphorescence material is creatively applied to an electroluminescence device.
Since the phosphorescent heavy metal material has a longer lifetime (μ s) and can cause triplet-triplet annihilation and concentration quenching under high current density, which leads to device performance attenuation, the heavy metal phosphorescent material is usually doped into a suitable host material to form a host-guest doped system, so that energy transfer is optimized, and luminous efficiency and lifetime are maximized. In the current research situation, the commercialization of heavy metal doped materials is mature, and it is difficult to develop alternative doped materials. Therefore, it is a common idea for researchers to place the center of gravity on the research and development of phosphorescent host materials.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide an N-biphenylene organic compound and an application thereof, wherein the prepared N-biphenylene organic compound is used as a host material in an electroluminescent device, such that the device has high light emitting efficiency and long lifetime.
The invention provides an N-heterobiphenyl organic compound which has a structure shown in a formula I, a formula II or a formula III:
wherein, A ring is independently selected from any one of the following groups:
X1、X2each independently selected from C-R12R13、N-R14O, S or P-R15；
R12～R15Independently selected from H, substituted or unsubstituted alkyl and derivatives thereof, substituted or unsubstituted alkoxy and derivatives thereof, substituted or unsubstituted aromatic ring and derivatives thereof, substituted or unsubstituted aromatic condensed ring and derivatives thereof, substituted or unsubstituted aromatic heterocycle and derivatives thereof, substituted or unsubstituted aromatic amine and derivatives thereof;
L1～L11each independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof;
R1～R11each independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof;
a. b, c, d, e, f, g, h, i, j and k are any integers independently selected from 0-3;
# denotes the fusion position.
The invention provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one N-heterobiphenyl organic compound.
The invention provides a display device which comprises the display panel.
Compared with the prior art, the invention provides an N-heterobiphenyl organic compound which has a structure shown in a formula I, a formula II or a formula III. The invention provides a series of compounds taking an N-heterobiphenyl structure as an electron accepting group, and the series of organic compounds are taken as main materials in an electroluminescent device and have higher triplet state energy level ETAnd the organic electroluminescent device has higher molecular density, higher glass transition temperature and molecular thermal stability, effectively improves the balance migration of carriers, widens an exciton recombination region, and effectively improves the light extraction efficiency, so that the luminous efficiency and the service life of the device are greatly improved, and the organic electroluminescent device can be well applied to the technical field of electroluminescent devices.
Detailed Description
In order to further illustrate the present invention, the organic compounds of the N-heterobiphenyls and the applications thereof provided by the present invention are described in detail below with reference to examples.
The invention provides an N-heterobiphenyl organic compound which has a structure shown in a formula I, a formula II or a formula III:
wherein, A ring is independently selected from any one of the following groups:
X1、X2each independently selected from C-R12R13、N-R14O, S or P-R15；
R12～R15Independently selected from H, substituted or unsubstituted alkyl and derivatives thereof, substituted or unsubstituted alkoxy and derivatives thereof, substituted or unsubstituted aromatic ring and derivatives thereof, substituted or unsubstituted aromatic condensed ring and derivatives thereof, substituted or unsubstituted aromatic heterocycle and derivatives thereof, substituted or unsubstituted aromatic amine and derivatives thereof;
L1～L11each independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof;
R1～R11each independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof;
a. b, c, d, e, f, g, h, i, j and k are any integers independently selected from 0-3;
# denotes the fusion position.
According to the invention, an indole ring is condensed in the structure of the carbazole heterocyclic compound, and the introduction of an indole group not only expands the ring of the carbazole heterocyclic compound, but also forms a conjugated structure with the carbazole heterocyclic group, so that the electron cloud arrangement of the carbazole heterocyclic compound is changed, the hole injection and hole transmission performance of the material is obviously improved, and the hole mobility is effectively improved.
Furthermore, a specific electron-withdrawing group is adopted for substitution, and the bipolar main body material with excellent electrical performance and energy level matching can be obtained by combining and matching with other electron-withdrawing groups, so that the charge balance is facilitated; the luminous area is effectively widened, the luminous efficiency is improved, and the service life of the device is prolonged.
Alternative to the invention, R12～R15Independently selected from H, substituted or unsubstituted C1-C10 alkyl and derivatives thereof, substituted or unsubstitutedThe aromatic amine derivative comprises C1-C10 alkoxy and derivatives thereof, substituted or unsubstituted C6-C40 aromatic rings and derivative groups thereof, substituted or unsubstituted C6-C40 aromatic condensed rings and derivative groups thereof, substituted or unsubstituted C5-C40 aromatic heterocycles and derivative groups thereof, and substituted or unsubstituted C6-C40 aromatic amines and derivative groups thereof.
Alternative to the invention, R12～R15Independently selected from H, substituted or unsubstituted C1-C10 alkyl and derivatives thereof, and substituted or unsubstituted six-membered aromatic ring and derivatives thereof.
Alternative to the invention, R12～R15Independently selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl.
Alternative to the invention, R12～R15Independently selected from H, methyl or phenyl.
In some embodiments of the invention, R12～R15Independently selected from phenyl.
Optionally, of the invention, said L1～L11Each independently selected from single bond, substituted or non-substituted aromatic ring of C6-C40 and derivative group thereof, substituted or non-substituted aromatic condensed ring of C6-C40 and derivative group thereof, and substituted or non-substituted aromatic heterocyclic ring of C5-C40 and derivative group thereof.
Optionally, of the invention, said L1～L11Each independently selected from single bond, substituted or non-substituted six-membered aromatic ring and derivative group thereof, substituted or non-substituted C6-C20 aromatic condensed ring and derivative group thereof, and substituted or non-substituted five-membered or six-membered aromatic heterocyclic ring and derivative group thereof.
Optionally, the single bond, substituted or unsubstituted phenyl and its derivatives, substituted or unsubstituted biphenyl and its derivatives, substituted or unsubstituted naphthyl and its derivatives, substituted or unsubstituted quinolyl and its derivatives, substituted or unsubstituted isoquinolyl and its derivatives, substituted or unsubstituted anthracenyl and its derivatives, substituted or unsubstituted phenanthryl and its derivatives, substituted or unsubstituted pyrenyl and its derivatives, substituted or unsubstituted pyridyl and its derivatives, substituted or unsubstituted pyrimidyl and its derivatives, substituted or unsubstituted triazinyl and its derivatives.
Alternative to the invention, R1～R11Each independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, and substituted or unsubstituted arylamine and derivative group thereof.
Alternative to the invention, R1～R11Each independently selected from H, substituted or unsubstituted aromatic ring of C6-C40 and derivative group thereof, substituted or unsubstituted aromatic condensed ring of C6-C40 and derivative group thereof, substituted or unsubstituted aromatic heterocyclic ring of C5-C40 and derivative group thereof, and substituted or unsubstituted aromatic amine of C6-C40 and derivative group thereof.
Alternative to the invention, R1～R11Each independently selected from H, substituted or unsubstituted six-membered aromatic ring and derivative group thereof, substituted or unsubstituted C6-C20 aromatic condensed ring and derivative group thereof, substituted or unsubstituted five-membered or six-membered aromatic heterocyclic ring and derivative group thereof, and substituted or unsubstituted C6-C20 arylamine and derivative group thereof.
Alternative to the invention, R1～R11Each independently selected from H, substituted or unsubstituted phenyl and its derivatives, substituted or unsubstituted carbazolyl and its derivatives, substituted or unsubstituted triphenylamine and its derivatives, substituted or unsubstituted diphenylamine and its derivatives, substituted or unsubstituted acridine and its derivatives, substituted or unsubstituted phenoxazinyl and its derivatives, substituted or unsubstituted phenothiazinyl and its derivatives, substituted or unsubstituted phenanthroline and its derivatives.
Optionally, the substituted aromatic ring and its derivative group, substituted aromatic condensed ring and its derivative group, substituted aromatic heterocycle and its derivative group, substituted alkyl and its derivative, substituted alkoxy and its derivative, and the substituent of the substituted aromatic amine and its derivative group is selected from:
one or more of substituted or unsubstituted C6-C40 aromatic rings and derivative groups thereof, substituted or unsubstituted C6-C40 aromatic condensed rings and derivative groups thereof, substituted or unsubstituted C5-C40 aromatic heterocycles and derivative groups thereof, and substituted or unsubstituted C6-C40 aromatic amines and derivative groups thereof.
In an alternative embodiment of the present invention, the above substituents are selected from phenyl.
Optionally, a, b, c, d, e, f, g, h, i, j and k are any integer selected from 0-3 independently.
Optionally, a, b, c, d, e, f, g, h, i, j, k are independently selected from 0, 1, 2 or 3.
In the present invention, # denotes the fusion site.
Optionally, the above N-heterobiphenyl organic compound has a structure represented by formula I-A or formula I-B:
wherein M is1、M2Independently selected from C, N, O, S or P.
R19、R23Independently selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl.
Alternative to the invention, R19、R23Independently selected from H, methyl or phenyl.
Alternative to the invention, R19、R23Independently selected from phenyl.
Alternative to the invention, L16、L20Independently selected from substituted or non-substituted pyrimidyl and derivatives thereof, substituted or non-substituted pyridyl and derivatives thereof, substituted or non-substituted quinolyl and derivatives thereof, substituted or non-substituted isoquinolylSubstituted phenyl and its derivatives, substituted or unsubstituted naphthyl and its derivatives, substituted or unsubstituted biphenyl and its derivatives, substituted or unsubstituted anthryl and its derivatives, substituted or unsubstituted phenanthryl and its derivatives, substituted or unsubstituted pyrenyl and its derivatives.
Alternative to the invention, L16、L20Independently selected from any of the following groups:
in the above structural formula, # denotes the position bonded to the benzene ring;
Alternative to the invention, L17、L18、L21、L22Independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof.
Alternative to the invention, L17、L18、L21、L22Independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl.
Alternative to the invention, R16、R17、R18、R20、R21、R22Independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof.
Alternative to the invention, R16、R17、R18、R20、R21、R22Independently selected from H, substituted or unsubstitutedPhenyl and its derivatives, substituted or unsubstituted carbazolyl and its derivatives, substituted or unsubstituted triphenylamine and its derivatives, substituted or unsubstituted diphenylamine and its derivatives, substituted or unsubstituted acridine and its derivatives, substituted or unsubstituted phenoxazinyl and its derivatives, substituted or unsubstituted phenothiazinyl and its derivatives, substituted or unsubstituted phenanthrolinyl and its derivatives.
The method is optional, and l, m, n, o, p and q are any integers of 0-3.
Optionally, l, m, n, o, p and q are 0, 1, 2 or 3.
In the present invention, the indole group is fused at a specific position of the carbazolo heterocyclic compound, and then L is added16、L20The position of the compound is connected with the specific electron-withdrawing substituent group, so that the whole structure has better charge balance, and the prepared compound has larger triplet state energy level ETAnd meanwhile, the organic photoelectric device has high density and high polarizability, and can improve the luminous efficiency, the chromaticity and the service life of the organic photoelectric device when being used as a phosphorescent light-emitting main body material.
Optionally, the above N-heterobiphenyl organic compound has a structure shown in formula ii-a:
wherein M is3Selected from C, N, O, S or P.
R27Selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl.
Alternative to the invention, R27Selected from H, methyl or phenyl.
Alternative to the invention, R27Selected from phenyl.
L24Selected from substituted or unsubstituted triazinyl and derivatives thereof, substituted or unsubstituted benzopyrimidinyl and derivatives thereof.
Alternative to the invention, L24Selected from any one of the following groups:
in the above structural formula, # denotes the position bonded to the benzene ring;
L25、L26Independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof.
Alternative to the invention, L25、L26Independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl.
R24、R25、R26Independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof.
Alternative to the invention, R24、R25、R26Independently selected from H, substituted or unsubstituted phenyl and derivatives thereof, substituted or unsubstituted carbazolyl and derivatives thereof, substituted or unsubstituted triphenylamine and derivatives thereof, substituted or unsubstituted diphenylamine and derivatives thereof, substituted or unsubstituted acridine and derivatives thereof, substituted or unsubstituted phenoxazinyl and derivatives thereof, substituted or unsubstituted phenothiazinyl and derivatives thereof, substituted or unsubstituted phenanthroline and derivatives thereof.
r, s and t are any integers of 0-3.
Optionally, r, s, and t are independently selected from 0, 1, 2, or 3.
In the present invention, an indole group is fused at the above-mentioned specific position of the carbazoloheterocyclic compound, and then L is added24The triazine group or the benzopyrimidinyl group and the derivative group thereof are connected at the position, so that the electron cloud density of the whole structure is balanced, and the prepared compound has a larger triplet state energy level ETAnd meanwhile, the organic photoelectric device has high density and high polarizability, and can improve the luminous efficiency, the chromaticity and the service life of the organic photoelectric device when being used as a phosphorescent light-emitting main body material. Experimental results show that the light-emitting device prepared by using the compound as a main material of a light-emitting layer has higher current efficiency and longer service life.
Optionally, the above N-heterobiphenyl organic compound has a structure shown in formula iii-a:
wherein M is4Selected from C, N, O, S or P.
R31Selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl.
Alternative to the invention, R31Selected from H, methyl or phenyl.
Alternative to the invention, R31Selected from phenyl.
L28Selected from substituted or unsubstituted triazinyl and derivatives thereof.
Alternative to the invention, L28Selected from the following groups:
in the above structural formula, # denotes the position bonded to the benzene ring;
L29、L30Independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof.
Alternative to the invention, L29、L30Independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl.
R28、R29、R30Independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof.
Alternative to the invention, R28、R29、R30Independently selected from H, substituted or unsubstituted phenyl and derivatives thereof, substituted or unsubstituted carbazolyl and derivatives thereof, substituted or unsubstituted triphenylamine and derivatives thereof, substituted or unsubstituted diphenylamine and derivatives thereof, substituted or unsubstituted acridine and derivatives thereof, substituted or unsubstituted phenoxazinyl and derivatives thereof, substituted or unsubstituted phenothiazinyl and derivatives thereof, substituted or unsubstituted phenanthroline and derivatives thereof.
u, v and w are any integer of 0-3.
Optionally, u, v, w are independently selected from 0, 1, 2 or 3.
In the present invention, an indole group is fused at the above-mentioned specific position of the carbazoloheterocyclic compound, and then L is added28The triazine group is connected in position, so that the electron cloud density of the whole structure is balanced, and the prepared compound has a larger triplet state energy level ETAnd meanwhile, the organic photoelectric device has high density and high polarizability, and can improve the luminous efficiency, the chromaticity and the service life of the organic photoelectric device when being used as a phosphorescent light-emitting main body material. The experimental result shows that the compound is used as the main material of the luminous layer to prepareThe resulting light emitting device has higher current efficiency and lifetime.
Optionally, the N-heterobiphenyl organic compound has any one of the following structures:
the invention provides a preparation method of the N-heterobiphenyl organic compound, which comprises the steps of taking a halogen substituted carbazole compound shown in a formula 1 and derivatives thereof as raw materials, and carrying out condensation reaction with a compound shown in a formula 2 to obtain the N-heterobiphenyl organic compound shown in a formula I;
or taking halogen substituted carbazole compound shown in formula 3 and derivatives thereof as raw materials, and carrying out condensation reaction with compound shown in formula 4 to obtain N hetero biphenyl organic compound shown in formula II;
or taking halogen substituted carbazole compound shown in formula 5 and derivatives thereof as raw materials, and carrying out condensation reaction with compound shown in formula 6 to obtain N hetero biphenyl organic compound shown in formula III;
wherein X is halogen;
L1～L9、a～i、R1～R9the scope of ring A is the same as above, and is not described herein.
The N-heterobiphenyl organic compound provided by the invention can be used as a main material, a doping material or an electron transport layer of an organic photoelectric device.
The invention provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one N-heterobiphenyl organic compound.
In an alternative aspect of the present invention, the organic thin film layer includes an electron transport layer, and the electron transport layer contains at least one of the above N-biphenylyl organic compounds.
The organic light-emitting device provided by the invention can be an organic light-emitting device well known to those skilled in the art, and optionally comprises a substrate, an ITO anode, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light-emitting layer, a first electron transport layer, a second electron transport layer, a cathode (a magnesium-silver electrode, the mass ratio of magnesium to silver is 1:9) and a cap layer (CPL).
In the invention, the anode material of the organic light-emitting device can be selected from metal-copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum and the like and alloys thereof; such as metal oxide-indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), etc.; such as conductive polymers-polyaniline, polypyrrole, poly (3-methylthiophene), and the like, and in addition to the above materials that facilitate hole injection and combinations thereof, include known materials suitable for use as anodes.
In the invention, the cathode material of the organic light-emitting device can be selected from metal-aluminum, magnesium, silver, indium, tin, titanium and the like and alloys thereof; such as multi-layer metal material-LiF/Al, LiO2/Al、BaF2Al, etc.; in addition to the above materials and combinations thereof that facilitate electron injection, known materials suitable for use as cathodes are also included.
In an alternative embodiment of the present invention, the organic optoelectronic device, for example, the organic thin film layer in the organic light emitting device, has at least one light emitting layer (EML), and may further include other functional layers, including a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL).
In an alternative embodiment of the present invention, the organic light emitting device is prepared according to the following method:
an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer.
Alternatively, the organic thin layer may be formed by a known film forming method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like.
The invention also provides a display device comprising the display panel.
In the present invention, an organic light emitting device (OLED device) may be used in a display device, wherein the organic light emitting display device may be a display screen of a mobile phone, a display screen of a computer, a display screen of a television, a display screen of a smart watch, a display panel of a smart car, a display screen of a VR or AR helmet, a display screen of various smart devices, and the like.
The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The following (tBu)3PHBF4Abbreviation for tri-tert-butylphosphine tetrafluoroborate.
Example 1
Step (1)
In a 250mL round-bottom flask, Compound A (15mmol), Compound B (10mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (35 mL)/ethanol (25mL) and aqueous potassium carbonate (15mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective product P-1.
Step (2)
Under an argon (Ar) atmosphere, compound P-1(20mmol), compound C (10mmol), Pd (OAc)2(1.6mmol)，(tBu)3PHBF4(5mmol)，K2CO3(6mmol) was placed in a 250mL three-necked flask, which was then heated and refluxed in 150mL of toluene solvent for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The thus-obtained crude product was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then, recrystallization was performed using a mixed solvent of toluene and hexane to obtain a solid compound P-2.
Characterization of the organic compound P-2: molecular formula C54H33N3；
ESI-MS (M/z) [ M +1 ] obtained by liquid-phase mass spectrometry]+: theoretical value 724.27, test value 724.50; elemental analysisTheoretical value: c89.60, H4.60, N5.81; test values are: c89.54, H4.65, N5.82.
Example 2
Compound P-1 was prepared according to the above procedure.
Under an argon (Ar) atmosphere, compound P-1(20mmol), compound E (10mmol), Pd (OAc)2(1.6mmol)，(tBu)3PHBF4(5mmol)，K2CO3(6mmol) was placed in a 250mL three-necked flask, which was then heated and refluxed in 150mL of toluene solvent for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The thus-obtained crude product was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then recrystallized using a mixed solvent of toluene and hexane to obtain a solid compound P-3.
Characterization of the organic compound P-3: molecular formula C54H33N3；
ESI-MS (M/z) [ M +1 ] obtained by liquid-phase mass spectrometry]+: theoretical value 724.27, test value 724.45; theoretical value of elemental analysis: c89.60, H4.60, N5.81; test values are: c89.55, H4.67, N5.81.
Example 3
In a 250mL round-bottom flask, Compound A (15mmol), Compound D (10mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (35 mL)/ethanol (25mL) and aqueous potassium carbonate (15mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. Cooling the resulting mixture to room temperature, adding water, filtering through a pad of celite, extracting the filtrate with dichloromethane, washing with water, drying over anhydrous magnesium sulfate, filtering and evaporating, purifying the crude product by column chromatography on silica gelObtaining the target product P-4.
Under an argon (Ar) atmosphere, compound P-4(20mmol), compound E (10mmol), Pd (OAc)2(1.6mmol)，(tBu)3PHBF4(5mmol)，K2CO3(6mmol) was placed in a 250mL three-necked flask, which was then heated and refluxed in 150mL of toluene solvent for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The thus-obtained crude product was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then recrystallized using a mixed solvent of toluene and hexane to obtain a solid compound P-5.
Characterization of the organic compound P-5: molecular formula C63H38N6；
ESI-MS (M/z) [ M +1 ] obtained by liquid-phase mass spectrometry]+: theoretical value 879.32, test value 879.60; theoretical value of elemental analysis: c86.08, H4.36, N9.56; test values are: c86.11, H4.37, N9.52.
Example 4
Under an argon (Ar) atmosphere, compound P-4(20mmol), compound F (10mmol), Pd (OAc)2(1.6mmol)，(tBu)3PHBF4(5mmol)，K2CO3(6mmol) was placed in a 250mL three-necked flask, which was then heated and refluxed in 150mL of toluene solvent for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The thus-obtained crude product was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then recrystallized using a mixed solvent of toluene and hexane to obtain a solid compound P-Y.
Characterization of the organic compounds P-Y: molecular formula C63H38N6；
ESI-MS (M/z) [ M +1 ] obtained by liquid-phase mass spectrometry]+: theoretical value 879.32, test value 879.50; theoretical value of elemental analysis: c86.08H4.36, N9.56; test values are: c86.10, H4.38, N9.52.
Application example 1
This application example provides an OLED device, OLED device includes in proper order: the LED structure comprises a glass substrate, an Indium Tin Oxide (ITO) anode 15nm, a first hole transport layer 10nm, a second hole transport layer 95nm, a light-emitting layer 30nm, a first electron transport layer 35nm, a second electron transport layer 5nm, a cathode 15nm (a magnesium-silver electrode, the mass ratio of magnesium to silver is 1:9) and a cap layer (CPL)100 nm.
The preparation steps of the OLED device are as follows:
(1) cutting the glass substrate into sizes of 50mm × 50mm × 0.7mm, respectively performing ultrasonic treatment in isopropanol and deionized water for 30min, and cleaning for 10min by exposing to ozone; mounting the obtained glass substrate with the ITO anode on a vacuum deposition device;
(2) under the vacuum degree of 2 x 10 < -6 > Pa, a compound HAT-CN is evaporated on the ITO anode layer in vacuum, the thickness of the compound HAT-CN is 10nm, and the compound HAT-CN is used as a first hole transport layer;
(3) vacuum evaporating a compound TAPC on the first hole transport layer to form a second hole transport layer with the thickness of 95 nm;
(4) co-depositing a light-emitting layer on the hole transport layer, wherein the organic compound P-2 provided by the invention is used as a main material, and Ir (piq)2(acac) as doping material, P-2 and Ir (piq)2(acac) mass ratio 19:1, thickness 30 nm;
(5) a compound BCP is evaporated on the luminous layer in vacuum to be used as a first electron transport layer, and the thickness is 35 nm;
(6) a compound Alq3 is evaporated on the first electron transport layer in vacuum to be used as a second electron transport layer, and the thickness is 5 nm;
(7) a magnesium-silver electrode is evaporated on the second electron transport layer in vacuum to serve as a cathode, the mass ratio of Mg to Ag is 1:9, and the thickness is 15 nm;
(8) a compound CBP having a high refractive index was vacuum-deposited on the cathode to a thickness of 100nm and used as a cathode cover layer (cap layer).
The structure of the compound used in the OLED device is as follows:
application examples 2 to 8
The organic compound P-2 in step (4) in application example 1 was replaced with the compound shown in table 1, and the other preparation steps were the same as in application example 1.
Comparative example 1
This comparative example differs from application example 1 only in that the organic compound P-2 in step (4) was used in the same amount as the comparative compound
Replacement; the other preparation steps are the same.
Performance evaluation of OLED devices:
testing the current of the OLED device under different voltages by using a Keithley 2365A digital nano-voltmeter, and then dividing the current by the light-emitting area to obtain the current density of the OLED device under different voltages; testing the brightness and radiant energy flux density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and the brightness of the OLED device under different voltages, working voltage and current efficiency (Cd/A) under the same current density (10mA/cm2) are obtained, and Von is the starting voltage under the brightness of 1Cd/m 2; lifetime LT95 (under 50mA/cm2 test conditions) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance; specific data are shown in table 1.
TABLE 1
According to the embodiments, the structure of the N-heterobiphenyl organic compound is modified and used as a main material in an electroluminescent device, so that the luminous efficiency and the service life of the device are greatly improved.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
Claims (11)
1. An N-heterobiphenyl organic compound having a structure represented by formula I, formula II or formula III:
wherein, A ring is independently selected from any one of the following groups:
X1、X2each independently selected from C-R12R13、N-R14O, S or P-R15；
R12～R15Independently selected from H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C6-C40 monocyclic aromatic ring, substituted or unsubstituted C6-C40 aromatic condensed ring, substituted or unsubstituted C5-C40 aromatic heterocycle, substituted or unsubstituted C6-C40 arylamine;
L1～L11each independently selected from single bond, substituted or unsubstituted C6-C40 monocyclic aromatic ring, substituted or unsubstituted C6-C40 aromatic condensed ring, and substituted or unsubstituted C5-C40 aromatic heterocycle;
R1～R11each independently selected from H, substituted or unsubstituted C6-C40 monocyclic aromatic ring, substituted or unsubstituted C6-C40 aromatic condensed ring, substituted or unsubstituted C5-C40 aromatic heterocycle, substituted or unsubstituted C6-C40 aromatic amine;
a. b, c, d, e, f, g, h, i, j and k are any integers independently selected from 0-3;
# denotes the fusion position;
the substituted monocyclic aromatic ring, the substituted aromatic condensed ring, the substituted aromatic heterocycle, the substituted alkyl, the substituted alkoxy and the substituted arylamine have the substituent selected from the group consisting of:
one or more of unsubstituted C6-C40 monocyclic aromatic ring, unsubstituted C6-C40 aromatic condensed ring, unsubstituted C5-C40 aromatic heterocycle and unsubstituted C6-C40 aromatic amine.
2. The Λ/-heterobiphenyl organic compound of claim 1, having the structure of formula i-a or formula i-B:
wherein M is1、M2Independently selected from C, N, O, S or P;
R19、R23independently selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl;
L16、L20independently selected from the group consisting of substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl;
L17、L18、L21、L22independently selected from single bond, substituted or non-substituted monocyclic aromatic ring, substituted or non-substituted aromatic condensed ring, substituted or non-substituted aromatic heterocyclic ring;
R16、R17、R18、R20、R21、R22independently selected from H, substituted or unsubstituted monocyclic aromatic ring, substituted or unsubstituted aromatic condensed ring, substituted or unsubstituted aromatic heterocycle, substituted or unsubstituted arylamine;
l, m, n, o, p and q are any integer of 0-3.
3. The Nheterobiphenyl organic compound of claim 2, wherein M is1、M2Independently selected from C, N, O, S or P;
R19、R23independently selected from H, methyl or phenyl;
l16 and L20 are independently selected from any one of the following groups:
L17、L18、L21、L22independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl;
R16、R17、R18、R20、R21、R22independently selected from H, substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted trianilino, substituted or unsubstituted dianilino, substituted or unsubstituted acridino, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenanthrolinyl;
l, m, n, o, p and q are any integer of 0-3;
# represents the position bonded to the benzene ring;
4. The Λ/-heterobiphenyl organic compound according to claim 1, having the structure of formula ii-a:
wherein M is3Selected from C, N, O, S or P;
R27selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl;
L24selected from substituted or unsubstituted triazinyl, substituted or unsubstituted benzopyrimidinyl;
L25、L26independently selected from single bond, substituted or non-substituted monocyclic aromatic ring, substituted or non-substituted aromatic condensed ring, substituted or non-substituted aromatic heterocyclic ring;
R24、R25、R26independently selected from H, substituted or unsubstituted monocyclic aromatic ring, substituted or unsubstituted aromatic condensed ring, substituted or unsubstituted aromatic heterocycle, substituted or unsubstituted arylamine;
r, s and t are any integers of 0-3.
5. The Nheterobiphenyl organic compound of claim 4, wherein M is3Selected from C, N, O, S or P;
R27selected from H, methyl or phenyl;
L24selected from any one of the following groups:
L25、L26independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl;
R24、R25、R26independently selected from H, substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted trianilino, substituted or unsubstituted dianilino, substituted or unsubstituted acridino, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenanthrolinyl;
r, s and t are any integers of 0-3;
# represents the position bonded to the benzene ring;
6. The Λ/-heterobiphenyl organic compound according to claim 1, having the structure of formula iii-a:
wherein M is4Selected from C, N, O, S or P;
R31selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl;
L28selected from substituted or unsubstituted triazinyl;
L29、L30independently selected from single bond, substituted or non-substituted monocyclic aromatic ring, substituted or non-substituted aromatic condensed ring, substituted or non-substituted aromatic heterocyclic ring;
R28、R29、R30independently selected from H, substituted or unsubstituted monocyclic aromatic ring, substituted or unsubstituted aromatic condensed ring, substituted or unsubstituted aromatic heterocycle, substituted or unsubstituted arylamine;
u, v and w are any integer of 0-3.
7. The Nheterobiphenyl organic compound of claim 6, wherein M is4Selected from C, N, O, S or P;
R31selected from H, methyl or phenyl;
L28selected from the following groups:
L29、L30independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl;
R28、R29、R30independently selected from H, substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted trianilino, substituted or unsubstituted dianilino, substituted or unsubstituted acridino, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenanthrolinyl;
u, v and w are any integer of 0-3;
# represents the position bonded to the benzene ring;
8. The Λ/-heterobiphenyl organic compound according to claim 1, having any of the following structures:
9. a display panel comprising an organic light emitting device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, the organic thin film layer comprising a light emitting layer containing at least one of the N-heterobiphenyl organic compounds according to any one of claims 1 to 8.
10. The display panel according to claim 9, wherein the organic thin film layer comprises an electron transport layer containing at least one of the N-heterobiphenyls organic compounds according to any one of claims 1 to 8.
11. A display device comprising the display panel according to any one of claims 9 to 10.
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