CN116239615A - Boron-containing organic compound and application thereof - Google Patents
Boron-containing organic compound and application thereof Download PDFInfo
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- CN116239615A CN116239615A CN202111483347.2A CN202111483347A CN116239615A CN 116239615 A CN116239615 A CN 116239615A CN 202111483347 A CN202111483347 A CN 202111483347A CN 116239615 A CN116239615 A CN 116239615A
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- Prior art keywords
- substituted
- unsubstituted
- ring
- heteroaryl
- formula
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- 229910052796 boron Inorganic materials 0.000 title claims abstract description 12
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 239000000463 material Substances 0.000 claims abstract description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 94
- 239000010410 layer Substances 0.000 claims description 84
- 125000001153 fluoro group Chemical group F* 0.000 claims description 81
- 229910052731 fluorine Inorganic materials 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 45
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 30
- 125000001769 aryl amino group Chemical group 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 30
- 125000004104 aryloxy group Chemical group 0.000 claims description 29
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 29
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 230000005669 field effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 35
- 238000003786 synthesis reaction Methods 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000543 intermediate Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 6
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 description 5
- 150000001793 charged compounds Chemical class 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000001046 green dye Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000001044 red dye Substances 0.000 description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000002994 raw material 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 229910001148 Al-Li alloy 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 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 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006616 biphenylamine 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
- 229910052792 caesium Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005238 degreasing 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
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 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
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- 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
-
- 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
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Indole Compounds (AREA)
Abstract
The invention relates to a boron-containing organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device. The compound has a structure shown in the following formula. Mother nucleus structure of the inventive compound moleculeThe para position in the central benzene ring is connected with two oxygen atoms, and simultaneously connected with two nitrogen atoms and two boron atoms. On the premise of keeping multiple resonances, the energy level split of the front line orbit generates effective red shift, so that the target molecule has high luminous efficiency and high color purity.
Description
Technical Field
The invention relates to a boron-containing organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device.
Background
The main way people acquire information is through vision, so that a display device is important in the process of human interaction with information. Organic Light Emitting Diodes (OLEDs) have many advantages of flexibility, self-luminescence, high contrast, large size, low power consumption, etc., and become one of the currently mainstream display devices.
The red dye and the green dye which are three primary colors can theoretically realize 100% internal quantum efficiency due to the fact that the red dye and the green dye generally contain heavy atoms such as Ir, pt and the like, and are high in electroluminescent efficiency and low in power consumption, so that the red dye and the green dye become the main stream of the current commercial display equipment. However, the chromaticity and lifetime of blue phosphorescent materials are not as good as the current commercial display requirements. Currently, blue light devices still employ conventional fluorescent materials to achieve high color purity and long device lifetime.
Recently, researchers of Japanese Takuji Hatakeyama and Junji Kido et al report a series of organic materials DABA-1 (adv. Mater.2016,28,2777-2781J. Mater. Chem. C,2019,7, 3082-3089) based on TADF (ThermallyActivated Delayed Fluorescence ) of boron-containing resonance type, boron atoms, nitrogen atoms and phenyl groups of the compounds constitute a rigid polycyclic aromatic skeleton, and thus have high fluorescence quantum yield. Compared with the traditional blue fluorescent dye, the compound has narrower spectrum and high color purity. However, the rigid planar structure also causes the energy level difference between the singlet state and the triplet state to be larger, the transition between the triplet state and the singlet state is slower, the exciton is compounded on the dye to cause serious efficiency roll-off, and the service life of the device is shorter. In addition, too planar a rigid structure often results in an adverse effect such as broadening of the spectrum and red shifting due to too high doping concentrations.
There is still a great room for improvement in the light emitting performance of the existing organic electroluminescent materials, and there is a need in the industry to develop new luminescent material systems to meet the commercial demands. Boron-containing resonant materials have the advantages of high color purity and high luminous efficiency, and are attracting wide attention in the scientific research and industry. However, since the peripheral substituent has little influence on the energy level, that is, the light color of the material is difficult to regulate and control, the light color of the material is always limited to a blue light-deep blue light area, and the further application of the material in the fields of high-resolution display, full-color display, white light illumination and the like is greatly limited.
Disclosure of Invention
The invention relates to a compound with a general formula, which has a structure shown in a general formula (1):
in the formula (1), Y 1 、Y 2 Each independently is N or B;
X 1 、X 2 each independently selected from NR 1 、BR 2 O or S;
ring A, ring D, ring E, ring F are each independently selected from any one of substituted or unsubstituted C6-C60 aromatic rings, substituted or unsubstituted C3-C60 heteroaromatic rings;
R 1 、R 2 each independently selected from any one of substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, R 1 、R 2 Each independently being unconnected to an adjacent ring structure or connected to form a ring by a chemical bond;
the substituents in ring A, ring D, ring E and ring F are each independently selected from at least one of halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl and unsubstituted or R ' substituted C3-C60 heteroaryl;
r' is independently selected from any one or a combination of at least two of halogen, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyl, C1-C20 alkyl silicon base, C1-C20 alkyl amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl or C3-C60 heteroaryl;
And at least one of the substituted substituents in ring A, ring D, ring E and ring F is a fluorine atom, or at least one R' is one of a fluorine atom substituted C1-C20 straight or branched alkyl group, a fluorine atom substituted C3-C20 cycloalkyl group, a fluorine atom substituted C6-C60 aryl group or a fluorine atom substituted C3-C60 heteroaryl group;
specifically, in formula (1), at least one ring of ring A, ring D, ring E, ring F is substituted with F atom;
or at least one of ring A, ring D, ring E, ring F is substituted with at least one of R ' substituted C1-C20 straight or branched chain alkyl, R ' substituted C3-C20 cycloalkyl, R ' substituted C1-C20 alkoxy, R ' substituted C1-C20 alkylsilyl, R ' substituted C1-C20 alkylamino, R ' substituted C6-C30 arylamino, R ' substituted C3-C30 heteroarylamino, R ' substituted C6-C30 aryloxy, R ' substituted C3-C30 heteroaryloxy, R ' substituted C6-C60 aryl, R ' substituted C3-C60 heteroaryl, and at least one R ' is a fluorine atom, or at least one R ' is a combination of a fluorine atom and any one of C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl, or C3-C60 heteroaryl;
The substituents in the ring A, the ring D, the ring E and the ring F are not connected independently, or 2 adjacent substituents are connected through chemical bonds to form a ring;
R 1 、R 2 wherein R' is independently selected from any one or a combination of at least two of halogen, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyl, C1-C20 alkyl silicon, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl or C3-C60 heteroaryl.
Further, in formula (1), the Y 1 、Y 2 Are all B; preferably, the X 1 、X 2 At least one of them is NR 1 The method comprises the steps of carrying out a first treatment on the surface of the More preferably, the X 1 、X 2 Are all NR 1 。
In the present specification, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are all shown above and are not repeated.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, in general, in the present specification, "each independently" means that the subject has a plurality of subjects, and they may be the same or different from each other.
Heteroatoms in the present specification generally refer to atoms or groups of atoms selected from N, O, S, P, si and Se, preferably N, O, S.
In the present specification, unless otherwise specified, the expression of a chemical element generally includes the concept of isotopes having the same chemical properties, for example, the expression of "hydrogen (H)", and also includes the expression of isotopes having the same chemical properties 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) then comprises 12 C、 13 C, etc., and are not described in detail.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present specification, unless otherwise specified, both aryl and heteroaryl include cases of single rings and condensed rings.
In the present specification, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and condensed ring aryl groups, preferably C6-C30 aryl groups, and further preferably C6-C20 aryl groups. By monocyclic aryl is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as, for example: phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl group includes a 2-biphenyl group, a 3-biphenyl group, and a 4-biphenyl group; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. Condensed ring aryl refers to a group in which at least two aromatic rings are contained in the molecule, and the aromatic rings are not independent of each other but share two adjacent carbon atoms condensed with each other. Exemplary are as follows: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl, 
And a radical, a tetracenyl radical, a derivative thereof, and the like. The naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethyl fluorenyl, 9-dipropyl fluorenyl, 9-dibutyl fluorenyl 9, 9-dipentylfluorenyl, 9-dihexylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, 9' -spirobifluorene, and benzofluorenyl.
The C3-C60 heteroaryl group mentioned in the present specification includes monocyclic heteroaryl groups and condensed ring heteroaryl groups, preferably C3-C30 heteroaryl groups, further preferably C4-C20 heteroaryl groups, and further preferably C5-C12 heteroaryl groups. Monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are linked by a single bond, and examples of the monocyclic heteroaryl group include: furyl, thienyl, pyrrolyl, pyridyl, and the like. Condensed ring heteroaryl means a group in which at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) are contained in a molecule and two adjacent atoms are fused together without being independent of each other. Examples of fused ring heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
Examples of the C6-C30 arylamino group mentioned in the present invention include: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like.
Examples of the C3-C30 heteroarylamino group mentioned in the present invention include: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
The chain alkyl group mentioned in the present invention includes a straight chain alkyl group and a branched chain alkyl group unless otherwise specified. Specifically, the substituted or unsubstituted C1-C30 chain alkyl group is preferably a substituted or unsubstituted C1-C16 chain alkyl group, more preferably a substituted or unsubstituted C1-C10 chain alkyl group. Examples of the substituted or unsubstituted C1-C10 chain alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl and the like.
In the present invention, the cycloalkyl group includes a monocycloalkyl group and a multicycloalkyl group; wherein, monocycloalkyl refers to an alkyl group having a single cyclic structure; polycycloalkyl refers to a structure in which two or more cycloalkyl groups are formed by sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present specification, examples of the C1-C10 alkoxy group which is preferably substituted or unsubstituted C1-C20 alkoxy group, and which is preferably substituted or unsubstituted C1-C10 alkoxy group, may be given as follows: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.
Further, the compound of the present invention has a structure as shown in formula (2):
in formula (2), ring a, ring D, ring E, ring F have the same defined ranges as in claim 1;
R a 、R b each independently selected from any one of substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
the R is a Not attached to ring E or attached by chemical bonds to form a ring, R b Is not connected with the ring F or is connected with the ring F through a chemical bond to form a ring;
R a 、R b Each of the substituted substituents is independently selected from any one or a combination of at least two of halogen, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl.
Preferably, said R a 、R b Each independently has a structure as shown in formula (B):
wherein the dotted line represents the attachment site of the group;
U 1 、U 2 、U 3 、U 4 、U 5 each independently selected from CR 4 Or N;
R 4 each independently selected from any one or a combination of at least two of hydrogen, halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; different R 4 Each independently of the other is not connected or is connected through a chemical bond to form a ring;
preferably, the U 1 、U 2 、U 3 、U 4 、U 5 Four of them are CR 4 The other is N;
or preferably, the U 1 、U 2 、U 3 、U 4 、U 5 Are all CR 4 。
Further, in the compounds of the general formula (1) or (2), the ring A, the ring D, the ring E and the ring F each independently have a structure as shown in the formula (A),
wherein the dashed line represents a fused bond of the group;
Z 1 、Z 2 、Z 3 、Z 4 each independently selected from CR 3 Or N;
R 3 each independently selected from hydrogen, halogen, unsubstituted or R' substituted C1-C20 straight or branched alkyl,Unsubstituted or R 'substituted C3-C20 cycloalkyl, unsubstituted or R' substituted C1-C20 alkoxy, unsubstituted or R 'substituted C1-C20 alkylsilyl, unsubstituted or R' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R 'substituted C6-C30 arylamino, unsubstituted or R' substituted C3-C30 heteroarylamino, unsubstituted or R 'substituted C6-C30 aryloxy, unsubstituted or R' substituted C3-C30 heteroaryloxy, unsubstituted or R 'substituted C6-C60 aryl, unsubstituted or R' substituted C3-C60 heteroaryl, and R 3 At least one of which is a fluorine atom or at least one R' is a fluorine atom; different R 3 Each independently of the other is not connected or is connected through a chemical bond to form a ring; r is R 3 Wherein each of said substituted substituents is independently unconnected, or adjacent 2 substituents are linked by a chemical bond to form a ring;
The definition of R' is the same as that in claim 1;
preferably, said Z 1 、Z 2 、Z 3 、Z 4 Three of them are CR 3 The other is N;
or preferably, the Z 1 、Z 2 、Z 3 、Z 4 Are all CR 3 。
Further, in formula (2), the R 11 、R 12 Each independently has a structure as shown in formula (B):
wherein the dotted line represents the attachment site of the group;
U 1 、U 2 、U 3 、U 4 、U 5 each independently selected from CR 4 Or N;
R 4 each independently selected from the group consisting of hydrogen, halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylaminoAny one or a combination of at least two of C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; different R 4 Each independently of the other is not connected or is connected through a chemical bond to form a ring;
preferably, the U 1 、U 2 、U 3 、U 4 、U 5 Four of them are CR 4 The other is N;
or preferably, the U 1 、U 2 、U 3 、U 4 、U 5 Are all CR 4 。
Still further, the compound of the present invention has a structure represented by any one of the formula (2-1), the formula (2-2) or the formula (2-3):
wherein X is 11 、X 12 、X 13 、X 14 、X 15 、X 16 、X 17 、X 18 、Y 11 、Y 12 、Y 13 、Y 14 、Y 15 、Y 16 、Y 17 、Y 18 Each independently selected from CR 5 Or N;
R 5 each independently selected from at least one of hydrogen, halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, and R 5 At least one of them is fluorine atom, or at least one R' is fluorine atom, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, CA combination of any of 6 to C60 aryl or C3 to C60 heteroaryl;
different R 5 Each independently of the other is not connected or is connected through a chemical bond to form a ring; r is R 5 Wherein each of said substituted substituents is independently unconnected, or adjacent 2 substituents are linked by a chemical bond to form a ring;
the definition of R' is the same as that in claim 1;
U 11 、U 12 、U 13 、U 14 、U 15 、U 16 、U 17 、U 18 、U 19 、U 20 each independently selected from CR 6 Or N; preferably U 11 、U 12 、U 13 、U 14 、U 15 、U 16 、U 17 、U 18 、U 19 、U 20 Each independently selected from CR 6 ；
R 6 Each independently selected from any one or a combination of at least two of hydrogen, halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; different R 6 Each independently of the other is not connected or is connected through a chemical bond to form a ring;
preferably, the compound of the general formula has a structure represented by the formula (2-3);
Preferably, R in formula (2-1), formula (2-2) and formula (2-3) 5 When the fluorine atom is R 'is fluorine atom or R' is a combination of fluorine atom and any one of C1-C20 straight chain or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl, the total number of fluorine atoms in the molecular structure of the compound is 1-20; more preferably, the total number of fluorine atoms in the molecular structure of the compound is 1 to 5.
Further, in the formula (2-1), the formula (2-2) and the formula (2-3):
Y 11 、Y 12 、Y 13 、Y 14 、Y 15 、Y 16 、Y 17 、Y 18 each independently selected from CR 5 And at least one R 5 Selected from a fluorine atom, or selected from one of the following groups substituted with a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
preferably, Y 13 、Y 17 Each independently selected from CR 5 And at least one R 5 Selected from a fluorine atom, or selected from one of the following groups substituted with a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
Still more preferably, Y 13 、Y 17 Each independently selected from CR 5 And at least one R 5 Selected from a fluorine atom, or selected from one of the following groups substituted with a fluorine atom: C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
more preferably, Y 13 、Y 17 Selected from the same CR 5 And R is 5 Selected from a fluorine atom, or selected from one of the following groups substituted with a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl.
Further, the compound of the present invention has a structure represented by any one of the formula (3-1), the formula (3-2) or the formula (3-3):
R 11 、R 12 、R 13 、R 14 、R 15 、R 16 independently represent monosubstituted to maximum allowable numberIs a substituent of (2);
R 11 、R 12 、R 13 、R 14 each independently selected from at least one of halogen, unsubstituted or R 'substituted C1-C20 straight or branched alkyl, unsubstituted or R' substituted C3-C20 cycloalkyl, unsubstituted or R 'substituted C1-C20 alkoxy, unsubstituted or R' substituted C1-C20 alkylsilyl, unsubstituted or R 'substituted C1-C20 alkylamino, unsubstituted or R' substituted C1-C20 heteroalkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R 'substituted C6-C30 arylamino, unsubstituted or R' substituted C3-C30 heteroarylamino, unsubstituted or R 'substituted C6-C30 aryloxy, unsubstituted or R' substituted C3-C30 heteroaryloxy, unsubstituted or R 'substituted C6-C60 aryl, unsubstituted or R' substituted C3-C60 heteroaryl, and R 11 、R 12 、R 13 、R 14 At least one of which is a fluorine atom or at least one R' is a fluorine atom;
R 11 、R 12 、R 13 、R 14 each independently of the other is not connected or is connected through a chemical bond to form a ring; r is R 11 、R 12 、R 13 、R 14 Wherein each of said substituted substituents is independently unconnected, or adjacent 2 substituents are linked by a chemical bond to form a ring; the definition of R' is the same as that in claim 1;
R 15 、R 16 each independently selected from any one or a combination of at least two of hydrogen, halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C1-C20 heteroalkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; different R 15 R is different from R 16 Each independently of the other is not connected or is connected through a chemical bond to form a ring;
preferably, in the formula (3-1), the formula (3-2) and the formula (3-3), the total number of fluorine atoms in the molecular structure of the compound is 1 to 10; more preferably, the total number of fluorine atoms in the molecular structure of the compound is 1 to 5.
Further, in the formula (3-1), the formula (3-2) and the formula (3-3):
R 11 、R 12 、R 13 、R 14 、R 15 、R 16 At least one of which is selected from a fluorine atom, or from one of the following groups substituted by a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
preferably, R 11 、R 12 、R 13 、R 14 、R 15 、R 16 Each independently represents 1 or 2 substituent groups, R 11 、R 12 、R 13 、R 14 The number of each is the same or different;
R 11 、R 12 、R 13 、R 14 at least one of which is selected from a fluorine atom, or from one of the following groups substituted by a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
preferably, R 11 、R 12 、R 13 、R 14 Each independently represents 1 or 2 substituent groups, R 11 、R 12 、R 13 、R 14 The number of each is the same or different;
further preferably, R 11 、R 12 Each represents a single substituent group, and R 11 、R 12 The connection sites of the substituent groups are respectively and independently positioned at the para positions of the connection sites of the B atoms on the benzene ring connected with the connection sites, R 11 、R 12 Each independently selected from a fluorine atom, or from one of the following groups substituted with a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60Heteroaryl;
still more preferably, R 11 、R 12 Each represents a single substituent group, and R 11 、R 12 The connection sites of the substituent groups are respectively and independently positioned at the para positions of the connection sites of the B atoms on the benzene ring connected with the connection sites, R 11 、R 12 Each independently selected from a fluorine atom, or from one of the following groups substituted with a fluorine atom: methylene, isopropylidene, t-butylidene, phenylene;
more preferably, R 11 、R 12 Is the same single substituent group and is simultaneously selected from fluorine atoms, or is selected from one of the following groups substituted by fluorine atoms: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, and R 11 、R 12 Is positioned at the para position of the B atom connecting site on the connected benzene ring;
most preferably, R 11 、R 12 Is the same single substituent group and is simultaneously selected from fluorine atoms, or is selected from one of the following groups substituted by fluorine atoms: methylene, isopropylidene, t-butylidene, and phenylene.
Further, the organic compounds of the present invention may preferably be represented by the following specific structural compounds N1 to N204, which are merely representative and do not limit the scope of the present invention:
In another aspect of the invention, there is also provided the use of a compound as described above in an organic electroluminescent device. In particular, the use as a material for a light-emitting layer in an organic electroluminescent device is preferred, more preferably as a material in a light-emitting layer in an organic electroluminescent device, and in particular as a luminescent dye can be applied.
As still another aspect of the present invention, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layers contain the compound of the general formula as described above or the compound of the structures N1 to N198 as described above.
Specifically, an embodiment of the present invention provides an organic electroluminescent device including a substrate, and a first electrode, a plurality of light emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transmission layer, a light-emitting layer and an electron transmission layer, wherein the hole injection layer is formed on the anode layer, the hole transmission layer is formed on the hole injection layer, the cathode layer is formed on the electron transmission layer, and the light-emitting layer is arranged between the hole transmission layer and the electron transmission layer; wherein the light-emitting layer contains the compound with the general formula or the compound with the structures of N1 to N204.
The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device; preferably, the display screen or display panel is an OLED display.
The invention also discloses electronic equipment, wherein the electronic equipment is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device.
The OLED device prepared by the compound has low starting voltage and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
The specific reason why the above-described compound of the present invention is excellent as a luminescent dye in a luminescent layer in an organic electroluminescent device is not clear, and it is presumed that the following reasons are possible:
1. the parent nucleus structure of the compound molecule of the invention is as follows: the para position in the central benzene ring is connected with two oxygen atoms, and simultaneously connected with two nitrogen atoms and two boron atoms. On the premise of keeping multiple resonances, the energy level split of the front line orbit generates effective red shift, so that the target molecule has high luminous efficiency and high color purity. The series of materials can obtain red light to near infrared emission.
2. The peripheral substituents in the molecular structure of the compound are not completely the same, and the compound has asymmetric characteristics, thereby being beneficial to the adjustment of the light color of materials and the improvement of the efficiency of devices.
3. The aromatic ring which is commonly connected with the boron atom and the hetero atom in the molecular structure of the compound is preferably provided with the substituent group containing the F atom at the para position of the boron atom, and the substituent group at the position is more beneficial to improving the light color red shift of a device due to the electron withdrawing effect of the F atom, adjusting the light color to the application range of mass production, reducing the sublimation temperature of the material, narrowing the spectrum possibly and improving the efficiency and the service life of the device.
In addition, the preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
Specific methods for preparing the above novel compounds of the present invention will be described below by way of example with reference to a plurality of synthesis examples, but the preparation method of the present invention is not limited to these synthesis examples.
It should be noted that, the method for obtaining the compound is not limited to the synthetic method and raw materials used in the present invention, and those skilled in the art may select other methods or routes to obtain the compound proposed in the present invention. All compounds of the synthesis process not mentioned in the present invention are commercially available starting products or are prepared by these starting products according to known methods.
The solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, t-butylbenzene, boron tribromide, carbazole, diphenylamine, etc., may be purchased from domestic chemical product markets, such as from the national pharmaceutical group reagent company, TCI company, shanghai pichia pharmaceutical company, carboline reagent company, etc.
The method for synthesizing the compound of the present invention will be briefly described.
The synthesis route is as follows:
analytical detection of intermediates and compounds in the present invention uses an absiex mass spectrometer (4000 QTRAP).
Synthesis example 1
Synthesis of compound N21:
synthesis of intermediate N21-1:
a (30 g,97.44 mmol), B (57.18 g,204.63 mmol), potassium carbonate (40.40 g,292.33 mmol) and N, N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, nitrogen was replaced 3 times, and the temperature was raised to 60℃to 70℃to react for 2 to 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate N21-1.5 g.
Synthesis of intermediate N21-2:
n21-1 (55.5 g,67.13 mmol), C (18.18 g,167.83 mmol), cesium carbonate (65.62 g,201.40 mmol), N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, nitrogen was replaced 3 times, and the temperature was raised to 100℃to react for 8 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate N21-2.5 g.
Synthesis of product N21:
intermediate N21-2 (25 g,24.73 mmol) was added to a 500ml three-necked flask, tert-butylbenzene (170 ml) was added, and after stirring for 20 minutes, the reaction system was cooled to 0℃and then N-butyllithium (29.68 mL,74.19 mmol) was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 60 ℃ and continuously heating for 2h. The reaction system temperature was again lowered to 0℃and boron tribromide (9.53 ml,98.92 mmol) was added under nitrogen protection, followed by stirring for 10 minutes and then heating to 60℃for 30 minutes. The temperature of the system was again lowered to 0deg.C and diisopropylethylamine (21.60 mL,123.65 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
After the reaction was cooled to room temperature, the organic phase was dried under reduced pressure. Column chromatography gives 8.6g crude product, toluene/ethanol recrystallization gives 5.6g red solid with 99.12% purity. Mass spectrometry determines molecular ion mass: 868.36 (theory: 868.42).
Synthesis example 2
Synthesis of compound N23:
synthesis of intermediate N23-1:
synthesis of N21-1 was repeated as illustrated in the previous embodiment to obtain 57.6g of a white solid.
Synthesis of intermediate N24-2:
n23-1 (52.5 g,67.13 mmol), C (20.02 g,158.76 mmol), cesium carbonate (62.07 g,190.51 mmol), N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, nitrogen was replaced 3 times, and the temperature was raised to 100℃to react for 8 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate N23-2.5 g.
Synthesis of product N23:
the synthesis scheme is the same as that of N21, 7.3g of crude product is obtained by column chromatography, 4.3g of red solid is obtained by toluene/ethanol recrystallization, and the purity is 99.26%. Mass spectrometry determines molecular ion mass: 896.37 (theory: 896.45).
Synthesis example 3
Synthesis of compound N24:
synthesis of intermediate N24-1:
synthesis of N24-1 gave, after recrystallization, 54.6g of a white solid.
Synthesis of intermediate N24-2:
n24-1 (55.5 g,67.13 mmol), C (18.18 g,167.83 mmol), cesium carbonate (65.62 g,201.40 mmol), N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, nitrogen was replaced 3 times, and the temperature was raised to 100℃to react for 8 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate N24-2.2 g.
Synthesis of product N24:
the synthesis scheme is the same as that of N21, column chromatography is carried out to obtain 6.5g of crude product, toluene/ethanol recrystallization is carried out to obtain 3.7g of red solid, and the purity is 99.66%. Mass spectrometry determines molecular ion mass: 868.32 (theory: 868.42).
Synthesis example 4
Synthesis of compound N61:
synthesis of intermediate N61-1:
a (30 g,67.13 mmol), B (24.67 g,220.09 mmol), cesium carbonate (86.05 g,264.11 mmol) and N, N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, the mixture was purged with nitrogen 3 times, and the temperature was raised to 100℃for 8 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate N61-1.5 g.
Synthesis of intermediate N61-2:
n61-1 (26.5 g,50.48 mmol), C (35.52 g,126.20 mmol), sodium tert-butoxide (14.55 g,151.44 mmol), (t-Bu) 3 PHBF 4 (2.93 g,10.10 mmol), pd2 (dba) 3 (4.87 g, 5.48), toluene (300 ml) was put into a 1000ml three-necked flask, nitrogen was purged 3 times, and the temperature was raised to 110℃for reaction for 12 hours.
The system is spin-dried, the crude product is obtained by column chromatography, 32g of intermediate N61-228.5g is obtained by toluene ethanol recrystallization.
Synthesis of product N61:
intermediate N61-2 (22.5 g,24.30 mmol) was added to a 500ml three-necked flask, tert-butylbenzene (170 ml) was added, and after stirring for 20 minutes, the reaction system was cooled to 0℃and then 45.56mL,72.89mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 60 ℃ and continuously heating for 2h. The reaction system temperature was again lowered to 0℃and boron tribromide (9.36 ml,97.19 mmol) was added under nitrogen protection, followed by stirring for 10 minutes and then heating to 60℃for 30 minutes. Diisopropylethylamine (21.12 mL,121.49 mmol) was added again to reduce the temperature of the system to 0deg.C. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
After the reaction was cooled to room temperature, the organic phase was dried under reduced pressure. Column chromatography gives 6.6g crude product, toluene/ethanol recrystallization gives 3.6g red solid with 99.42% purity. Mass spectrometry determines molecular ion mass: 872.63 (theory: 872.45).
Synthesis example 5
Synthesis of compound N64:
synthesis of intermediate N64-1:
a (30 g,67.13 mmol), B (24.67 g,220.09 mmol), cesium carbonate (86.05 g,264.11 mmol) and N, N-dimethylformamide (300 ml) were put into a 1000ml three-necked flask, the mixture was purged with nitrogen 3 times, and the temperature was raised to 100℃for 8 hours.
The temperature of the system was lowered to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from toluene/ethanol to give intermediate N64-1.5 g.
Synthesis of intermediate N64-2:
synthesis of N61-2 gave 28.6g of a white solid after recrystallization.
Synthesis of product N64:
the synthesis scheme is the same as that of N61, 7.2g of crude product is obtained by column chromatography, 4.1g of red solid is obtained by toluene/ethanol recrystallization, and the purity is 99.36%. Mass spectrometry determines molecular ion mass: 872.63 (theory: 872.45).
Device embodiment
Description of the embodiments
The OLED includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1-HI-3 described below; one or more compounds from HT-1 to HT-51 may also be used to dope one or more of HI-1-HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the present invention, the host material of the light emitting layer is selected from, but not limited to, one or more combinations of the following pH-1 to pH-85.
In one aspect of the invention, the light-emitting layer employs a thermally activated delayed fluorescence light-emitting technique. The light emitting layer includes, in addition to a host material, a first dopant, which may be selected from, but is not limited to, a combination of one or more of TDE1-TDE49 listed below, and/or a second dopant, which is selected from a combination of one or more of the organic compounds represented by formula I.
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 through HT-51 described above, or one or more compounds of PH-47 through PH-77 described above; mixtures of one or more compounds of HT-1 through HT-51 and one or more compounds of PH-47 through PH-77 may also be employed, but are not limited thereto.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-73 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-73 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
LiQ,LiF,NaCl,CsF,Li 2 O,Cs 2 CO 3 ,BaO,Na,Li,Ca，Mg，Yb。
The preparation process of the organic electroluminescent device in this embodiment is as follows:
the procedure for making example 1 of the thermally activated delayed fluorescence device is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with anode in vacuum chamber, vacuumizing to<1×10 -5 Pa, vacuum thermal evaporation is carried out on the anode layer film in sequence, wherein 10nm of HT-4:HI-3 (97/3,w/w) mixture is used as a hole injection layer, 60nm of compound HT-4 is used as a hole transport layer, and 5nm of compound HT-51 is used as an electron blocking layer; a ternary mixture of a 40nm compound PH54, TDE42 and N1 (100:50:1, w/w/w) as a light-emitting layer; PH-28 at 5nm was used as hole blocking layer, a 25nm mixture of compounds ET-69:ET-57 (50/50, w/w) was used as electron transport layer, liF at 1nm was used as electron injection layer, and metallic aluminum at 150nm was used as cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Device examples 2-14 and comparative examples 1-3 were prepared in the same manner as in device example 1 except that N1 in the light-emitting layer was replaced with N21, N22, N23, N24, N25, N41, N42, N44, N45, N197, N198, N199, N201 and compounds C1, C2 and C3 in the prior art.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
testing the light color of the device by testing the fluorescence emission spectrum; measuring the external quantum efficiency of the organic electroluminescent device by using an integrating sphere;
the properties of the thermally activated sensitized delayed fluorescence device prepared in each of the above examples are shown in table 1 below.
| Examples | Numbering of compounds | Luminescence peak (nm) | EQE(％) |
| Comparative example 1 | C1 | 595 | 11.2 |
| Comparative example 2 | C2 | 640 | 6.9 |
| Comparative example 3 | C3 | 642 | 7.3 |
| Example 1 | N1 | 620 | 17.0 |
| Example 2 | N21 | 621 | 17.2 |
| Example 3 | N22 | 622 | 17.0 |
| Example 4 | N23 | 623 | 16.9 |
| Example 5 | N24 | 620 | 16.6 |
| Example 6 | N25 | 623 | 17.0 |
| Example 7 | N41 | 615 | 16.7 |
| Example 8 | N42 | 617 | 16.9 |
| Example 9 | N44 | 615 | 16.3 |
| Example 10 | N45 | 619 | 17.1 |
| Example 11 | N197 | 618 | 16.9 |
| Example 12 | N198 | 625 | 16.2 |
| Example 13 | N199 | 622 | 16.5 |
| Example 14 | N201 | 623 | 16.3 |
As can be seen from table 1, when the compound of the present invention is used as a dye, the light color of the comparative example compound C1 is reddish, just near 620nm, and the efficiency is higher, which may be that the light color is redshifted due to the electron withdrawing fluorine-containing group contained in the compound of the present invention, and for the compound C1, the sensitizer in the device cannot be used for complete energy transfer, thus the efficiency is lower; the comparative example compound C2 is too red in light color compared with the compound of the invention, and the existence of sulfur atoms damages the plane rows of the compound, so that the device efficiency is extremely low, and the existence of a plurality of F atoms causes the light color to be too red, so that the efficiency is reduced. Therefore, the compound of the invention meets the requirements of red light devices in light color, and has advantages in efficiency.
The foregoing description of the embodiments has been provided for the purpose of illustrating the general principles of the invention, and is not meant to limit the invention thereto, but to limit the invention thereto, and any modifications, equivalents, improvements and equivalents thereof may be made without departing from the spirit and principles of the invention.
Claims (12)
1. A compound of the general formula (1) has the structure shown in the general formula:
in the formula (1), Y 1 、Y 2 Each independently is N or B;
X 1 、X 2 each independently selected from NR 1 、BR 2 O or S;
ring A, ring D, ring E, ring F are each independently selected from any one of substituted or unsubstituted C6-C60 aromatic rings, substituted or unsubstituted C3-C60 heteroaromatic rings;
R 1 、R 2 each independently selected from substituted or unsubstituted C1 to C20 straight or branched chainAny one of alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, wherein R is 1 、R 2 Each independently being unconnected to an adjacent ring structure or connected to form a ring by a chemical bond;
the substituents in ring A, ring D, ring E and ring F are each independently selected from at least one of halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl and unsubstituted or R ' substituted C3-C60 heteroaryl;
R' is independently selected from any one or a combination of at least two of halogen, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyl, C1-C20 alkyl silicon base, C1-C20 alkyl amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl or C3-C60 heteroaryl;
and at least one of the substituted substituents in ring A, ring D, ring E and ring F is a fluorine atom, or at least one R' is one of a fluorine atom substituted C1-C20 straight or branched alkyl group, a fluorine atom substituted C3-C20 cycloalkyl group, a fluorine atom substituted C6-C60 aryl group or a fluorine atom substituted C3-C60 heteroaryl group;
the substituted substituents in ring A, ring D, ring E and ring F are each independently unconnected, or adjacent 2 substituents are connected into a ring through chemical bonds;
R 1 、R 2 wherein each of the substituted substituents is independently selected from the group consisting of halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, ammoniaAny one or a combination of at least two of a group, a hydroxyl group, a C1-C20 alkyl silicon group, a C1-C20 alkyl amino group, a C6-C30 aryl amino group, a C3-C30 heteroaryl amino group, a C6-C30 aryloxy group, a C3-C30 heteroaryl oxy group, a C6-C60 aryl group or a C3-C60 heteroaryl group.
2. A compound of formula (la) according to claim 1, wherein Y 1 、Y 2 Are all B;
preferably, the X 1 、X 2 At least one of them is NR 1 ；
More preferably, the X 1 、X 2 Are all NR 1 。
3. The compound of formula (la) according to claim 1, wherein the compound has a structure as shown in formula (2):
in formula (2), ring a, ring D, ring E, ring F have the same defined ranges as in claim 1;
R a 、R b each independently selected from any one of substituted or unsubstituted C1-C20 straight or branched chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
the R is a Not attached to ring E or attached by chemical bonds to form a ring, R b Is not connected with the ring F or is connected with the ring F through a chemical bond to form a ring;
R a 、R b wherein each of the substituted substituents is independently selected from any one of halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl A combination of the two.
4. A compound of the general formula according to any one of claims 1 to 3, wherein the rings A, D, E, F each independently have a structure represented by the formula (A),
wherein the dashed line represents a fused bond of the group;
Z 1 、Z 2 、Z 3 、Z 4 each independently selected from CR 3 Or N;
R 3 each independently selected from at least one of hydrogen, halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, and R 3 At least one of which is a fluorine atom or at least one R' is a fluorine atom; different R 3 Each independently of the other is not connected or is connected through a chemical bond to form a ring; r is R 3 Wherein each of said substituted substituents is independently unconnected, or adjacent 2 substituents are linked by a chemical bond to form a ring;
The definition of R' is the same as that in claim 1;
preferably, said Z 1 、Z 2 、Z 3 、Z 4 Three of them are CR 3 The other is N;
or preferably, the Z 1 、Z 2 、Z 3 、Z 4 Are all CR 3 。
5. A compound of formula (la) according to claim 3, wherein R a 、R b Each independently has a structure as shown in formula (B):
wherein the dotted line represents the attachment site of the group;
U 1 、U 2 、U 3 、U 4 、U 5 each independently selected from CR 4 Or N;
R 4 each independently selected from any one or a combination of at least two of hydrogen, halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; different R 4 Each independently of the other is not connected or is connected through a chemical bond to form a ring;
preferably, the U 1 、U 2 、U 3 、U 4 、U 5 Four of them are CR 4 The other is N;
or preferably, the U 1 、U 2 、U 3 、U 4 、U 5 Are all CR 4 。
6. A compound of the general formula according to claim 3, having a structure represented by any one of the formula (2-1), the formula (2-2) or the formula (2-3):
wherein X is 11 、X 12 、X 13 、X 14 、X 15 、X 16 、X 17 、X 18 、Y 11 、Y 12 、Y 13 、Y 14 、Y 15 、Y 16 、Y 17 、Y 18 Each independently selected from CR 5 Or N;
R 5 each independently selected from at least one of hydrogen, halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, and R 5 At least one of which is a fluorine atom, or at least one R' is a combination of a fluorine atom and any one of C1-C20 straight-chain or branched-chain alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl;
different R 5 Each independently of the other is not connected or is connected through a chemical bond to form a ring; r is R 5 Wherein each of said substituted substituents is independently unconnected, or adjacent 2 substituents are linked by a chemical bond to form a ring;
The definition of R' is the same as that in claim 1;
U 11 、U 12 、U 13 、U 14 、U 15 、U 16 、U 17 、U 18 、U 19 、U 20 each independently selected from CR 6 Or N; preferably U 11 、U 12 、U 13 、U 14 、U 15 、U 16 、U 17 、U 18 、U 19 、U 20 Each independently selected from CR 6 ；
R 6 Each independently selected from hydrogen, halogen, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxyAny one or a combination of at least two of C1-C20 alkyl silicon group, C1-C20 alkyl amino group, C6-C30 aryl amino group, C3-C30 heteroaryl amino group, C6-C30 aryloxy group, C3-C30 heteroaryl oxy group, C6-C60 aryl group or C3-C60 heteroaryl group; different R 6 Each independently of the other is not connected or is connected through a chemical bond to form a ring;
preferably, the compound of the general formula has a structure represented by the formula (2-3);
preferably, R in formula (2-1), formula (2-2) and formula (2-3) 5 When the fluorine atom is R 'is fluorine atom or R' is a combination of fluorine atom and any one of C1-C20 straight chain or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl, the total number of fluorine atoms in the molecular structure of the compound is 1-20; more preferably, the total number of fluorine atoms in the molecular structure of the compound is 1 to 10, and still more preferably, the total number of fluorine atoms in the molecular structure of the compound is 1 to 5.
7. The compound according to claim 6, wherein in formula (2-1), formula (2-2), formula (2-3):
Y 11 、Y 12 、Y 13 、Y 14 、Y 15 、Y 16 、Y 17 、Y 18 each independently selected from CR 5 And at least one R 5 Selected from a fluorine atom, or selected from one of the following groups substituted with a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
preferably, Y 13 、Y 17 Each independently selected from CR 5 And at least one R 5 Selected from a fluorine atom, or selected from one of the following groups substituted with a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6%A C60 aryl, C3-C60 heteroaryl;
still more preferably, Y 13 、Y 17 Each independently selected from CR 5 And at least one R 5 Selected from a fluorine atom, or selected from one of the following groups substituted with a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl;
More preferably, Y 13 、Y 17 Selected from the same CR 5 And R is 5 Selected from a fluorine atom, or selected from one of the following groups substituted with a fluorine atom: C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl.
8. A compound according to claim 3, having a structure represented by any one of formula (3-1), formula (3-2) or formula (3-3):
R 11 、R 12 、R 13 、R 14 、R 15 、R 16 each independently represents a substituent group monosubstituted to a maximum permissible number;
R 11 、R 12 、R 13 、R 14 each independently selected from at least one of halogen, unsubstituted or R 'substituted C1-C20 straight or branched alkyl, unsubstituted or R' substituted C3-C20 cycloalkyl, unsubstituted or R 'substituted C1-C20 alkoxy, unsubstituted or R' substituted C1-C20 alkylsilyl, unsubstituted or R 'substituted C1-C20 alkylamino, unsubstituted or R' substituted C1-C20 heteroalkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R 'substituted C6-C30 arylamino, unsubstituted or R' substituted C3-C30 heteroarylamino, unsubstituted or R 'substituted C6-C30 aryloxy, unsubstituted or R' substituted C3-C30 heteroaryloxy, unsubstituted or R 'substituted C6-C60 aryl, unsubstituted or R' substituted C3-C60 heteroaryl, and R 11 、R 12 、R 13 、R 14 At least one of which is a fluorine atom or at least one R' is a fluorine atom;
R 11 、R 12 、R 13 、R 14 each independently of the other is not connected or is connected through a chemical bond to form a ring; r is R 11 、R 12 、R 13 、R 14 Wherein each of said substituted substituents is independently unconnected, or adjacent 2 substituents are linked by a chemical bond to form a ring; the definition of R' is the same as that in claim 1;
R 15 、R 16 each independently selected from any one or a combination of at least two of hydrogen, halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C20 alkoxy, nitro, cyano, amino, hydroxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C1-C20 heteroalkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; different R 15 R is different from R 16 Each independently of the other is not connected or is connected through a chemical bond to form a ring;
preferably, in the formula (3-1), the formula (3-2) and the formula (3-3), the total number of fluorine atoms in the molecular structure of the compound is 1 to 10; more preferably, the total number of fluorine atoms in the molecular structure of the compound is 1 to 5.
9. The compound of claim 8, wherein in formula (3-1), formula (3-2), formula (3-3):
R 11 、R 12 、R 13 、R 14 At least one of which is selected from a fluorine atom, or from one of the following groups substituted by a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
preferably, R 11 、R 12 、R 13 、R 14 Independently of each other, represents 1 or 2 substituentsGroup R 11 、R 12 、R 13 、R 14 The number of each is the same or different;
further preferably, R 11 、R 12 Each represents a single substituent group, and R 11 、R 12 The connection sites of the substituent groups are respectively and independently positioned at the para positions of the connection sites of the B atoms on the benzene ring connected with the connection sites, R 11 、R 12 Each independently selected from a fluorine atom, or from one of the following groups substituted with a fluorine atom: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl;
still more preferably, R 11 、R 12 Each represents a single substituent group, and R 11 、R 12 The connection sites of the substituent groups are respectively and independently positioned at the para positions of the connection sites of the B atoms on the benzene ring connected with the connection sites, R 11 、R 12 Each independently selected from a fluorine atom, or from one of the following groups substituted with a fluorine atom: methylene, isopropylidene, t-butylidene, phenylene;
More preferably, R 11 、R 12 Is the same single substituent group and is simultaneously selected from fluorine atoms, or is selected from one of the following groups substituted by fluorine atoms: C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, and R 11 、R 12 Is positioned at the para position of the B atom connecting site on the connected benzene ring;
most preferably, R 11 、R 12 Is the same single substituent group and is simultaneously selected from fluorine atoms, or is selected from one of the following groups substituted by fluorine atoms: methylene, isopropylidene, t-butylidene, and phenylene.
10. The compound of claim 1, having the structure shown below:
11. use of a compound of the general formula according to any one of claims 1 to 10 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper;
preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, more preferably as a light-emitting dye in a light-emitting layer.
12. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound according to any one of claims 1 to 10;
preferably, the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 10.
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