CN117285551A - Boron-containing organic compound and application thereof - Google Patents
Boron-containing organic compound and application thereof Download PDFInfo
- Publication number
- CN117285551A CN117285551A CN202210667428.6A CN202210667428A CN117285551A CN 117285551 A CN117285551 A CN 117285551A CN 202210667428 A CN202210667428 A CN 202210667428A CN 117285551 A CN117285551 A CN 117285551A
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- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- group
- aryl
- heteroaryl
- Prior art date
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims description 21
- 229910052796 boron Inorganic materials 0.000 title claims description 20
- 150000002894 organic compounds Chemical class 0.000 title claims description 18
- 239000000463 material Substances 0.000 claims abstract description 28
- 239000010410 layer Substances 0.000 claims description 86
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 58
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 16
- 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
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical group O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 84
- 230000009286 beneficial effect Effects 0.000 abstract description 7
- 238000001228 spectrum Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 description 63
- 238000003786 synthesis reaction Methods 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 53
- 239000000543 intermediate Substances 0.000 description 51
- 239000000758 substrate Substances 0.000 description 23
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 22
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002994 raw material Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- 239000000975 dye Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 150000001793 charged compounds Chemical class 0.000 description 10
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 10
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 10
- 238000004949 mass spectrometry Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 239000002356 single layer Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000010189 synthetic method 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
- 239000012043 crude product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000001046 green dye Substances 0.000 description 3
- 239000011777 magnesium Substances 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
- 230000008569 process Effects 0.000 description 3
- 239000001044 red dye Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 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
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000013461 design Methods 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
- 239000002019 doping agent Substances 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
- 239000007850 fluorescent dye Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 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
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- 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
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 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
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 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
- 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
- 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
- 125000004432 carbon atom Chemical group C* 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[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
- 238000006073 displacement reaction Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000000605 extraction Methods 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 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
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 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
- 238000004020 luminiscence type Methods 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
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([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
- 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
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 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
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 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
- 239000007858 starting material Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing 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
- 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
- 229910052722 tritium Inorganic materials 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
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- 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
- C07F5/027—Organoboranes and organoborohydrides
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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
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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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
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a 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, and the compound provided by the invention is beneficial to improving the efficiency and the service life of a device and is beneficial to adjusting the light-emitting spectrum.
Description
Technical Field
The invention relates to a boron-containing organic material, 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 (Thermally Activated 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, the resonant dye is more planar in structural characteristics, so that molecular aggregation is very easy to occur, the color purity is reduced, and the device performance is reduced.
Disclosure of Invention
In order to solve the technical problems, the invention designs a kind of resonance type fluorescent dye with a boron-containing structure and a specific structure.
The invention provides a boron-containing organic compound, which has a structure shown in a general formula (1):
in the formula (1), the ring A is one of a substituted or unsubstituted C6-C50 aryl, a substituent or an unsubstituted C2-C50 heteroaryl;
X 1 、X 2 each independently is CR 4 ；
R 1 、R 4 Each independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the R is 1 、R 4 Optionally with or without an adjacent group;
R 2 、R 3 each independently selected from one of halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and R 2 、R 3 At least one of which is a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl, and R 2 、R 3 Each independently not linked to an adjacent group to form a ring;
m is CR 5 R 6 、NR 7 Any of O, S or Se;
R 5 、R 6 and R is 7 Each independently selected from one of halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
Z 1 、Z 2 each independently selected from NR 8 One of O, S, R 8 One selected from the group consisting of a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl;
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
the substituent group in the ring A is selected from one of halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R 'substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R' substituted C3-C20 cycloalkyl, unsubstituted or R 'substituted C1-C20 alkoxy, unsubstituted or R' substituted C1-C20 alkyl silicon group, unsubstituted or R 'substituted C6-C60 arylamino, unsubstituted or R' substituted C6-C60 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 selected from one or two of halogen, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, cyano, nitro, hydroxy, amino, C1-C20 alkyl silicon, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, C3-C30 heteroarylthio, C6-C60 aryl or C3-C60 heteroaryl.
Further, the ring a in formula (1) has a structure as shown in formula (a):
in formula (a), the dotted line represents the condensed connection position with formula (1);
the Y is 1 、Y 2 、Y 3 、Y 4 Each independently selected from CR 9 Or N, the R 9 One selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, said two adjacent R 9 Are connected in a ring or are not connected;
R 9 wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;
preferably, said Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from CR 9 ；
Still preferably, the Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from CR 9 And the R is 9 One selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl and substituted or unsubstituted C3-C10 cycloalkyl;
most preferably, said Y 1 、Y 2 、Y 3 、Y 4 Are independently selected from CR 9 And the R is 9 One selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl.
The compound of the present invention preferably has a structure represented by formula (2) or formula (3):
m, X in the formulas (2) and (3) 1 、X 2 、Z 1 、Z 2 、R 1 、R 2 、R 3 The definitions of Y1 to Y4 are the same as those in the formula (1), and the definitions of Y1 to Y4 are the same as those in the formula (a).
Preferably, in the formulas (2) and (3), the Y 2 Selected from CR 9 The R is 9 One selected from the group consisting of a substituted or unsubstituted C1-C10 chain alkyl group and a substituted or unsubstituted C3-C10 cycloalkyl group;
More preferably, in the formulas (2) and (3), the Y 2 Selected from CR 9 The R is 9 One selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-amyl, cyclopropyl, cyclopentyl or cyclohexyl;
most preferably, in the formulas (2) and (3), the Y 1 、Y 3 、Y 4 Are independently selected from CR 9 And the R is 9 Selected from hydrogen, said Y 2 Selected from CR 9 The R is 9 One selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl.
The compound of the invention, in the formula (1), the formula (2) and the formula (3), M is S or O; preferably, M is S.
The compound of the present invention, wherein in the formula (1), the formula (2) and the formula (3), Z 1 、Z 2 Each independently is NR 8 ；
Preferably, said R 8 Selected from substituted or unsubstituted C6-C60 aryl, R 8 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
preferably, said R 8 One selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthryl or phenanthryl, R 8 Each of the substituents independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
The compound of the present invention is represented by the formula (1), the formula (2) and the formula (3), wherein R 1 At least one selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
preferably, R 1 At least one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, and substituted or unsubstituted C6-C30 aryl; more preferably, R 1 And one of hydrogen, methyl, ethyl, isopropyl, tertiary butyl, phenyl, biphenyl, naphthyl, anthryl and phenanthryl.
The compound of the present invention is represented by the formula (1), the formula (2) and the formula (3), wherein R 2 、R 3 Each independently selected from one of a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, and R 2 、R 3 At least one of which is a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl, and R 2 、R 3 Each independently not linked to an adjacent group to form a ring;
preferably, said R 2 、R 3 Each independently selected from one of a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and R 2 、R 3 At least one of which is a substituted or unsubstituted C6-C60 aryl group, and R 2 、R 3 Each independently of the other not adjacent radicalsThe clusters are linked into rings.
The compound of the present invention is represented by the formula (1), the formula (2) and the formula (3), wherein X is 1 、X 2 Each independently is CR 4 ；
Preferably, said R 4 One selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
still more preferably, the R 4 Selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, R 4 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl; continuing preferably, said R 4 One selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl and cyclohexyl; more preferably, the R 4 Selected from hydrogen.
The compound of the present invention is represented by the formula (1), the formula (2) and the formula (3), wherein R 5 、R 6 And R is 7 Each independently selected from one of a substituted or unsubstituted C1-C20 chain alkyl, a substituted or unsubstituted C3-C60 cycloalkyl, a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl;
Preferably, R 5 、R 6 And R is 7 Each independently selected from one of a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group.
In the present invention, 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 (at least 2), the substituents may be the same or different substituents; when the following description refers to the same expression mode, the same meaning is provided, and the selection ranges of the substituents are shown above and are not repeated.
In the present invention, the halogen may be fluorine, chlorine, bromine or iodine. The following description refers to the same meaning.
In the present invention, unless otherwise specified, the expression of chemical elements includes the concept of isotopes having the same chemical properties, for example, hydrogen (H) includes 1H (protium), 2H (deuterium, D), 3H (tritium, T), and the like; carbon (C) includes 12C, 13C, etc.
In the present invention, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, si or Se.
In the present invention, the expression "ring structure" means that the linking site is located at any position on the ring structure that can be bonded.
In the present invention, the expression of Ca to Cb means that the group has a carbon number of a to b, and the carbon number does not include the carbon number of the substituent unless otherwise specified.
In the present invention, "each independently" means that the subject has a plurality of subjects, and the subjects may be the same or different from each other.
In the present invention, each of the C6 to C60 may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.
The C3-C60 can be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, C58, etc.
The C1-C20 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, or the like.
The C3-C20 may be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, or the like.
The C1-C36 may be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C25, C28, C30, C32, C34, C35, or the like.
The C3-C20 may be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, or the like.
The C1-C10 can be C1, C2, C3, C4, C5, C6, C7, C8, C9 or C10.
The C6-C30 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
The C3-C30 may be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, or the like.
In the present invention, the substituted or unsubstituted C6-C60 aryl group, the substituted or unsubstituted C6-C30 aryl group includes both monocyclic aryl groups and condensed ring aryl groups, 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.
In the present invention, the substituted or unsubstituted C3 to C60 heteroaryl group and the substituted or unsubstituted C3 to C30 heteroaryl group each include a monocyclic heteroaryl group and a condensed ring heteroaryl group, preferably a C4 to C20 heteroaryl group, more preferably a C5 to C12 heteroaryl group. 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.
The chain alkyl group mentioned in the present invention includes a straight chain alkyl group and a branched chain alkyl group. 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. Substituted or unsubstituted C3-C30 cycloalkyl, preferably substituted or unsubstituted C3-C20 cycloalkyl, more preferably substituted or unsubstituted C3-C10 cycloalkyl, for example: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl, n-octyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, tert-pentyl, cyclohexyl, adamantyl and the like.
As preferable structures of the present invention related compounds, the following specific compounds M1 to M242 may be mentioned, but are not limited to these compounds:
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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 (1), (2) or (3) as described above or the compound of the structures M1 to M242 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 of the general formula (1), (2) or (3) or the compound of the structures M1 to M242.
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 lower starting voltage and longer service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
The specific reason why the 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 may be the reason:
1. the boron atoms contained in the compound and the nitrogen atoms in the same ring have resonance effect, and the stronger central rigid structure is beneficial to reducing the Stokes displacement of molecules, so that the series of materials have the characteristic of narrow spectrum emission, and the luminous efficiency in the device is improved; meanwhile, the five-membered ring in the center of the molecule can effectively reduce the triplet state energy level of the molecule, which is beneficial to the improvement of the stability of the device;
2. according to the invention, an aromatic group and an alkyl group are simultaneously introduced into the boron-containing compound, so that the light color of the material can be effectively regulated and controlled to be kept at a blue light level (< 490 nm);
3. according to the invention, the aromatic group and the alkyl group are introduced into the compound, so that a class of large steric hindrance groups are introduced, a certain steric hindrance effect exists, the interaction between dye molecules can be reduced, concentration aggregation and quenching of the dye molecules can be reduced, the efficiency roll-off of the organic electroluminescent device can be inhibited, and the efficiency of the device can be improved;
4. The compound of the invention has R simultaneously existing on the ortho-position and the para-position of M on the five-membered heterocycle in the parent nucleus 2 And R is 3 A group, and R 2 And R is 3 At least one of the compounds is an aryl group or a heteroaryl group, and the design scheme of the specific optional group structure at the specific site can improve the dipole orientation arrangement of the compounds to a certain extent, so that the compounds have certain light extraction characteristics, and the efficiency of devices adopting the compounds is further improved; meanwhile, the aryl or heteroaryl arranged at the specific position on the five-membered heterocycle in the parent nucleus structure can increase the carrier transmission capability of the compound when the compound is applied as a dye to a certain extent, thereby being beneficial to improving the performance of the device;
6. the preparation process of the compound is simple and feasible, 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.
Synthetic examples
Synthesis path 1:
synthesis path 2:
analytical detection of intermediates and compounds in the present invention uses an absiex mass spectrometer (4000 QTRAP).
Synthesis example 1
Synthesis of compound M3:
synthesis of intermediate M3-1:
SM1 (22.5 g,80 mmol), SM2 (28.1 g,100 mmol), pd2 (dba) 3 (1 g,1.08 mmol), S-phos (0.9 g,2.16 mmol), sodium t-butoxide (11.5 g,120 mmol) and toluene (1000 mL) were put into a 2000mL three-necked flask, nitrogen was replaced 3 times, and the reaction was performed at elevated temperature and reflux for 12 hours. The system was cooled to room temperature, purified by column chromatography to give 28.9g of crude product, and recrystallized from toluene/petroleum ether to give intermediate M3-1.3 g of white solid.
Synthesis of intermediate M3-2:
m3-1 (14.1 g,30 mmol), SM3 (16.5 g,40 mmol), pd2 (dba) 3 (0.5 g,0.54 mmol), S-phos (0.45 g,1.08 mmol), sodium t-butoxide (5.8 g,60 mmol) and toluene (500 mL) were put into a 1000mL three-necked flask, nitrogen was replaced 3 times, and the reaction was performed at reflux under elevated temperature for 12 hours. The system was cooled to room temperature, purified by column chromatography to give 18.6g of crude product, and recrystallized from toluene/n-hexane to give intermediate M3-2.2 g of white solid.
Synthesis of product M3:
intermediate M3-2 (12.2 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added, the mixture was replaced with nitrogen 3 times, the reaction system was cooled to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining the low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Silica gel column chromatography, toluene ethanol recrystallization twice, 1.9g yellow solid M3, purity 99.66%. Mass spectrometry determines molecular ion mass: 790.48 (theory: 790.44).
Synthesis example 2
Synthesis of compound M7:
synthesis of intermediate M7-1:
and intermediate M5-1.
Synthesis of intermediate M7-2:
with the synthesis of intermediate M5-2, the corresponding substrate raw material is replaced
Synthesis of product M7:
intermediate M7-2 (13.1 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added thereto, the mixture was replaced with nitrogen 3 times, the temperature of the reaction system was lowered to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining the low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Silica gel column chromatography and toluene ethanol recrystallization twice, 2.1g yellow solid M7 with purity of 99.92% is obtained. Mass spectrometry determines molecular ion mass: 846.76 (theory: 846.51).
Synthesis example 3
Synthesis of compound M15:
synthesis of intermediate M15-1:
with intermediate M5-1, the relevant substrate raw material is replaced
Synthesis of intermediate M15-2:
with the synthesis of intermediate M5-2, the corresponding substrate raw material is replaced
Synthesis of product M15:
intermediate M15-2 (12 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added, the reaction system was cooled to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes at a low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Silica gel column chromatography and toluene ethanol recrystallization twice, 2.2g yellow solid M15 with purity of 99.82% is obtained. Mass spectrometry determines molecular ion mass: 776.56 (theory: 776.43).
Synthesis example 4
Synthesis of Compound M20:
synthesis of intermediate M20-1:
with intermediate M5-1, the relevant substrate raw material is replaced
Synthesis of intermediate M20-2:
with the synthesis of intermediate M5-2, the corresponding substrate raw material is replaced
Synthesis of product M20:
intermediate M20-2 (13.7 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added thereto, the mixture was replaced with nitrogen 3 times, the temperature of the reaction system was lowered to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining the low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Silica gel column chromatography and toluene ethanol recrystallization twice, 1.7g yellow solid M20 with purity of 99.54% is obtained. Mass spectrometry determines molecular ion mass: 888.59 (theory: 888.55).
Synthesis example 5
Synthesis of Compound M34:
synthesis of intermediate M34-1:
with intermediate M5-1, the relevant substrate raw material is replaced
Synthesis of intermediate M34-2:
With the synthesis of intermediate M5-2, the corresponding substrate raw material is replaced
Synthesis of product M34:
intermediate M34-2 (12.8 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added thereto, the mixture was replaced with nitrogen 3 times, the temperature of the reaction system was lowered to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining the low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Silica gel column chromatography, toluene ethanol recrystallization twice, 1.4g yellow solid M34, purity 99.64%. Mass spectrometry determines molecular ion mass: 832.65 (theory: 832.49).
Synthesis example 6
Synthesis of Compound M82:
synthesis of intermediate M82-1:
with intermediate M5-1, the relevant substrate raw material is replaced
Synthesis of intermediate M82-2:
with the synthesis of intermediate M5-2, the corresponding substrate raw material is replaced
Synthesis of product M82:
intermediate M82-2 (12.2 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added, the reaction system was cooled to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining a low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Silica gel column chromatography, toluene ethanol recrystallization twice, 1.6g yellow solid M82, purity 99.79%. Mass spectrometry determines molecular ion mass: 790.56 (theory: 790.44).
Synthesis example 7
Synthesis of Compound M92:
synthesis of intermediate M92-1:
with intermediate M5-1, the relevant substrate raw material is replaced
Synthesis of intermediate M92-2:
with the synthesis of intermediate M5-2, the corresponding substrate raw material is replaced
Synthesis of product M92:
intermediate M92-2 (12.5 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added thereto, the mixture was replaced with nitrogen 3 times, the temperature of the reaction system was lowered to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining the low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Column chromatography on silica gel with toluene ethanol recrystallisation twice gives 1.4g of yellow solid M92 with a purity of 99.79%. Mass spectrometry determines molecular ion mass: 804.61 (theory: 804.46).
Synthesis example 8
Synthesis of Compound M116:
synthesis of intermediate M116-1:
with intermediate M5-1, the relevant substrate raw material is replaced
Synthesis of intermediate M116-2:
with the synthesis of intermediate M5-2, the corresponding substrate raw material is replaced
Synthesis of product M116:
intermediate M116-2 (13 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added, the reaction system was cooled to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes at a low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Silica gel column chromatography, toluene ethanol recrystallization twice, 1.5g yellow solid M116, purity 99.82%. Mass spectrometry determines molecular ion mass: 846.59 (theory: 846.51).
Synthesis example 9
Synthesis of compound M162:
synthesis of intermediate M162-1:
with intermediate M5-1, the relevant substrate starting material was replaced.
Synthesis of intermediate M162-2:
M162-1 (14.5 g,30 mmol), SM3 (20.7 g,50 mmol), pd2 (dba) 3 (0.5 g,0.54 mmol), S-phos (0.45 g, 1.08 mmol), sodium t-butoxide (5.8 g,60 mmol) and toluene (500 mL) were put into a 1000mL three-necked flask, nitrogen was replaced 3 times, and the reaction was performed at reflux under elevated temperature for 12 hours. The system was cooled to room temperature, purified by column chromatography to give 18.2g of crude product, and recrystallized from toluene/n-hexane to give intermediate M162-2.2 g of white solid.
Synthesis of product M162:
intermediate M162-2 (12.2 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added, the mixture was replaced with nitrogen 3 times, the temperature of the reaction system was lowered to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining the low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Column chromatography on silica gel with toluene ethanol recrystallisation twice gives 1.2g of yellow solid M162 with a purity of 99.43%. Mass spectrometry determines molecular ion mass: 790.52 (theory: 790.44).
Synthesis example 10
Synthesis of compound M202:
synthesis of intermediate M202-1:
with intermediate M5-1, the relevant substrate raw material is replaced
Synthesis of intermediate M202-2:
with the synthesis of intermediate M5-2, the corresponding substrate raw material is replaced
Synthesis of product M202:
intermediate M202-2 (12.6 g,15 mmol) was added to a 500ml three-necked flask, xylene (200 ml) was added, the mixture was replaced with nitrogen 3 times, the reaction system was cooled to-60℃and tert-butyllithium (18.7 mL,30 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining the low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (7.41 g,30 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again reduced to-40℃and diisopropylethylamine (5.81 g,45 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
Silica gel column chromatography and toluene ethanol recrystallization twice, 1.8g yellow solid M202 with purity of 99.74% is obtained. Mass spectrometry determines molecular ion mass: 816.72 (theory: 816.51).
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.
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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 invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
In one aspect of the invention, the barrier layer surrounding the light emitting layer may be selected from, but is not limited to, one or more combinations of PH-1 to PH-85.
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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.
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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、Yb、Mg。
The preparation process of the organic electroluminescent device in this embodiment 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 the 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-14 is used as an electron blocking layer; a binary mixture of 20nm of a compound BFH-4:M3 (100:3, w/w) as a light-emitting layer; 5nm ET-23 as hole blocking layer, 25nm compound ET-69:ET-57 (50/50, w/w) mixture as electron transport layer, 1nm LiF as electron injection layer, 150nm metallic aluminum 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 to 15 were produced in the same manner as in device example 1 except that the dye M3 in the light-emitting layer was replaced with the compound shown in Table 1, respectively.
Device comparative examples 1 to 6 were fabricated in the same manner as in device example 1, except that the dye M3 in the light-emitting layer was replaced with the prior art compounds Ref-1, ref-2, ref-3, ref-4, ref-5 and Ref-6, respectively:
wherein, ref-1 and Ref-6 refer to the synthetic methods in CN 111253421A; ref-2 and Ref-5 refer to the synthetic methods in CN 1119333810A; ref-3 refers to the synthetic method in CN 113201003A; ref-4 refers to the synthesis method in WO2021194216A, and the above synthesis method is not described herein.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the devices of the organic electroluminescent devices prepared in examples 1 to 15 and comparative examples 1 to 6 were measured using a digital source table and PR650 at the same brightness. Specifically, the luminance of the organic electroluminescent device was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage under the corresponding brightness, and meanwhile, the external quantum efficiency (EQE%) of the device can be obtained through direct test on PR 650;
the device lifetime LT95 is tested as follows: at 1000cd/m using a luminance meter 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 950cd/m 2 Time in hours. The L95 of the other devices was the relative value to comparative example 1, taking Ref-1 lifetime as 100%.
The properties of the organic electroluminescent devices prepared in the above device examples 1 to 15 and device comparative examples 1 to 6 are shown in Table 1 below.
Table 1:
from the results in table 1 above, it is shown that the devices of examples 1 to 15 prepared using such boron-containing organic compounds of the present invention as luminescent dyes obtain relatively high external quantum efficiency, and at the same time, the device voltage is reduced and the device lifetime is improved, compared to the devices of comparative examples 1 to 6 prepared using the comparative compounds of the prior art as luminescent dyes, on the basis that the other functional layer materials and the process parameters are the same in the devices.
For example, to implement the device9 as can be seen from comparison of device comparative examples 5 and 6, the external quantum efficiency of devices prepared using the compound M92 of the present invention as a luminescent dye was improved by 11.2% and 10.4% respectively, and the device lifetime was improved by 23.9% and 37.8% respectively, and the device voltage was also reduced relatively, respectively, compared to devices prepared using the comparative compounds Ref-5 and Ref-6, respectively. The inventors speculate that the reason is that: because the compounds of the invention have defined R in the formula 2 And R is R 3 Are not H, and R 2 、R 3 At least one of the compounds is one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and compared with a comparison compound, the compound with the specific structure is more beneficial to improving the carrier transmission capability of the material, improving the steric effect of molecules and achieving the beneficial effects of efficiency improvement, service life improvement and voltage reduction.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (12)
1. A boron-containing organic compound having a structure represented by formula (1):
in the formula (1), the ring A is one of a substituted or unsubstituted C6-C50 aryl, a substituent or an unsubstituted C2-C50 heteroaryl;
X 1 、X 2 each independently is CR 4 ；
R 1 、R 4 Each independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain One of an alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 silyl group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group; the R is 1 、R 4 Optionally with or without an adjacent group;
R 2 、R 3 each independently selected from one of halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and R 2 、R 3 At least one of which is a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl, and R 2 、R 3 Each independently not linked to an adjacent group to form a ring;
m is CR 5 R 6 、NR 7 Any of O, S or Se;
R 5 、R 6 and R is 7 Each independently selected from one of halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
Z 1 、Z 2 Each independently selected from NR 8 One of O, S, R 8 One selected from the group consisting of a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl;
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 wherein the substituents are each independently selected from the group consisting of halogen, C1-C20 linear alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxyOne or two of a group, a C6-C60 aryl group and a C3-C60 heteroaryl group;
the substituent group in the ring A is selected from one of halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R 'substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R' substituted C3-C20 cycloalkyl, unsubstituted or R 'substituted C1-C20 alkoxy, unsubstituted or R' substituted C1-C20 alkyl silicon group, unsubstituted or R 'substituted C6-C60 arylamino, unsubstituted or R' substituted C6-C60 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 selected from one or two of halogen, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, cyano, nitro, hydroxy, amino, C1-C20 alkyl silicon, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylthio, C3-C30 heteroarylthio, C6-C60 aryl or C3-C60 heteroaryl.
2. The boron-containing organic compound according to claim 1, wherein the ring a in the formula (1) has a structure as shown in the formula (a):
in formula (a), the dotted line represents the condensed connection position with formula (1);
the Y is 1 、Y 2 、Y 3 、Y 4 Each independently selected from CR 9 Or N, the R 9 Selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstitutedOne of substituted C6-C60 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, said two adjacent R 9 Are connected in a ring or are not connected;
R 9 wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;
preferably, said Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from CR 9 ；
Still preferably, the Y 1 、Y 2 、Y 3 、Y 4 Each independently selected from CR 9 And the R is 9 One selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl and substituted or unsubstituted C3-C10 cycloalkyl;
most preferably, said Y 1 、Y 2 、Y 3 、Y 4 Are independently selected from CR 9 And the R is 9 One selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl.
3. The boron-containing organic compound according to claim 2, having a structure represented by formula (2) or formula (3):
m, X in the formulas (2) and (3) 1 、X 2 、Z 1 、Z 2 、R 1 、R 2 、R 3 Is defined as in formula (1), Y 1 -Y 4 Is defined as in formula (a)；
Preferably, in the formulas (2) and (3), the Y 2 Selected from CR 9 The R is 9 One selected from the group consisting of a substituted or unsubstituted C1-C10 chain alkyl group and a substituted or unsubstituted C3-C10 cycloalkyl group;
More preferably, in the formulas (2) and (3), the Y 2 Selected from CR 9 The R is 9 One selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-amyl, cyclopropyl, cyclopentyl or cyclohexyl;
most preferably, in the formulas (2) and (3), the Y 1 、Y 3 、Y 4 Are independently selected from CR 9 And the R is 9 Selected from hydrogen; the Y is 2 Selected from CR 9 The R is 9 One selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl.
4. A boron-containing organic compound according to claim 1 or 3, wherein M is S or O;
preferably, M is S.
5. A boron-containing organic compound according to claim 1 or 3, wherein Z 1 、Z 2 Each independently is NR 8 ；
Preferably, said R 8 Selected from substituted or unsubstituted C6-C60 aryl, R 8 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
preferably, said R 8 One selected from the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl, anthryl or phenanthryl, R 8 Each of the substituents independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
6. According to the weightsThe boron-containing organic compound according to claim 1 or 3, wherein R 1 At least one selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
preferably, R 1 At least one selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, and substituted or unsubstituted C6-C30 aryl;
more preferably, R 1 And one of hydrogen, methyl, ethyl, isopropyl, tertiary butyl, phenyl, biphenyl, naphthyl, anthryl and phenanthryl.
7. A boron-containing organic compound according to claim 1 or 3, wherein said R 2 、R 3 Each independently selected from one of a substituted or unsubstituted C1-C20 chain alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, and R 2 、R 3 At least one of which is a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl, and R 2 、R 3 Each independently not linked to an adjacent group to form a ring;
preferably, said R 2 、R 3 Each independently selected from one of a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, and R 2 、R 3 At least one of which is a substituted or unsubstituted C6-C60 aryl group, and R 2 、R 3 Each independently is not linked to an adjacent group to form a ring.
8. A boron-containing organic compound according to claim 1 or 3, characterized in that said R 4 One selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
preferably, said R 4 Selected from the group consisting ofHydrogen, a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, R 4 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl;
continuing preferably, said R 4 One selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl and cyclohexyl;
more preferably, the R 4 Selected from hydrogen.
9. A boron-containing organic compound according to claim 1 or 3, wherein said R 5 、R 6 And R is 7 Each independently selected from one of a substituted or unsubstituted C1-C20 chain alkyl, a substituted or unsubstituted C3-C60 cycloalkyl, a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl;
Preferably, R 5 、R 6 And R is 7 Each independently selected from one of a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group.
10. The boron-containing organic compound of claim 1, having a structure shown below:
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11. use of an organic compound 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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