CN117126183A - Organic compound and application thereof, and organic electroluminescent device comprising organic compound - Google Patents
Organic compound and application thereof, and organic electroluminescent device comprising organic compound Download PDFInfo
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- CN117126183A CN117126183A CN202210525192.2A CN202210525192A CN117126183A CN 117126183 A CN117126183 A CN 117126183A CN 202210525192 A CN202210525192 A CN 202210525192A CN 117126183 A CN117126183 A CN 117126183A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 claims abstract description 35
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000010410 layer Substances 0.000 claims description 83
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001769 aryl amino 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
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 18
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 230000000903 blocking effect Effects 0.000 claims description 13
- 230000005525 hole transport Effects 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 239000002346 layers by function Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 6
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 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 4
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 75
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 238000001228 spectrum Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 9
- 238000004020 luminiscence type Methods 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- RXXXUIOZOITBII-UHFFFAOYSA-N indeno[1,2-g]indole Chemical compound C1=C2C=CC=CC2=C2C1=C1N=CC=C1C=C2 RXXXUIOZOITBII-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000001308 synthesis method Methods 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-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
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000295 emission spectrum Methods 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
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 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
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 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
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical compound CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 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
- 239000004793 Polystyrene Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 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
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 238000010504 bond cleavage reaction Methods 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
- 150000001768 cations Chemical class 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000021615 conjugation Effects 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
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
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- 238000005401 electroluminescence 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
- 239000001046 green dye Substances 0.000 description 1
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- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 230000002093 peripheral effect Effects 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000003077 quantum chemistry computational method Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride 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
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 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
- 230000036962 time dependent Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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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 System
- 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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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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- 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
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- 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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- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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Abstract
The invention relates to a boron-nitrogen-containing organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device. The organic compound has a structure represented by the following formula. The organic compound provided by the invention is beneficial to improving the efficiency and the service life of devices and beneficial to blue shift adjustment of spectrums.
Description
Technical Field
The invention relates to a boron-nitrogen-containing organic compound, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device.
Background
With the continuous progress and development of social science, display technology becomes vital in people's life. Organic Light Emitting Diodes (OLEDs) are one of the currently mainstream display devices because of their advantages of flexibility, self-luminescence, high contrast, large size, low power consumption, etc.
The light-emitting mechanism of OLEDs is that electrons and holes recombine under electrical excitation to form excitons, which obey probability statistical distribution, with singlet excitons accounting for about 25% and triplet excitons accounting for about 75%. The first generation luminescence technology, which is collectively referred to as fluorescence technology, is luminescence using singlet excitons; the second generation luminescence technology is called phosphorescence technology, which utilizes triplet state excitons to emit light, and can theoretically achieve 100% internal quantum efficiency, but heavy metals required for constructing phosphorescent dyes are expensive and pollute the environment, so that the third generation thermal excitation delayed fluorescence technology constructed by using organic small molecules is commonly adopted at present, and when the energy level difference of single-triplet state is small, the triplet state excitons can cross to a singlet state between opposite systems, and then return to a ground state to emit light. Among them, red and green dyes, which are three primary colors, are the mainstream of the current commercial display devices because of their high electroluminescent efficiency and low power consumption. However, the chromaticity and lifetime of blue materials are not as good as the current commercial display requirements, and blue devices still use conventional fluorescent materials to achieve high color purity and long device lifetime.
Recently, a series of organic micromolecular materials DABCA-1 (adv. Mater.2016,28,2777-2781J. Mater.chem.C,2019,7, 3082-3089) based on boron-nitrogen resonance type thermal excitation delayed fluorescence are reported by the subject groups of Japanese Takuji Hatakeyama, junji Kido and the like, and boron atoms, nitrogen atoms and phenyl groups in the compounds form a rigid polycyclic aromatic resonance skeleton, so that the compound has higher fluorescence quantum yield. Compared with the traditional blue fluorescent dye, the compound has narrower emission spectrum band gap and higher 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. Furthermore, too planar a rigid structure often results in an adverse effect due to too high a doping concentration, which leads to a broadening of the emission spectrum and a red shift.
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 nitrogen resonance type materials have the advantages of high color purity and high luminous efficiency, and are attracting wide attention in the scientific research and industry. However, since the peripheral substituent has little influence on the energy level, that is, the light color of the material is difficult to regulate and control, the light color of the material is always limited to the sky blue region, and the further application of the material in the fields of high-resolution display, full-color display, white light illumination and the like is greatly limited.
As OLED products continue to enter the market, there is an increasing demand for the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, lifetime, cost, etc. The researchers of the present invention have discovered a smart molecular design through careful thought and continuous experimentation and are described in detail below. Surprisingly, the disclosed compounds are well suited for application in OLEDs and to enhance the performance of the device and to adjust its emission color to deep blue.
Disclosure of Invention
In order to solve the technical problems, the invention designs a boron-nitrogen structure-containing resonant fluorescent dye with a specific structure and capable of emitting deep blue light, and can effectively adjust the light color of a material to the deep blue light, and meanwhile, the efficiency and the service life of a device can be improved.
The invention provides a boron-nitrogen-containing organic compound, which has a structure shown in a general formula (1):
in the formula (1):
ring A and ring B each independently represents one of a substituted or unsubstituted C5-C60 aromatic ring and a substituted or unsubstituted C3-C60 heterocyclic ring;
the substituents in ring A and ring B are each independently selected from at least one of halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, the substituents in ring A and ring B are each independently unconnected, or 2 adjacent substituents are linked through a chemical bond to form a ring;
R 1 And R is 2 Each independently selected from one of a substituted or unsubstituted C1-C20 straight or branched chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C3-C60 heteroarylamino group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C3-C30 heteroaryloxy group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;
L 1 selected from single bond, CR 1 R 2 An O atom, an S atom, NR 3 One of the following;
R 1 、R 2 and R is 3 Each independently selected from one of a substituted or unsubstituted C1-C20 straight or branched chain alkyl, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C6-C60 aryl, and a substituted or unsubstituted C3-C60 heteroaryl;
X 1 、X 2 、X 3 are independently selected from CR 3 Or N, the R 3 Independently 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 arylamine A group, a substituted or unsubstituted C6-C60 heteroarylamino group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C3-C30 heteroaryloxy group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group; the adjacent two R' s 3 Are connected in a ring or are not connected;
X 1 、X 2 、X 3 at least one of them is CR 3 And the R is 3 Is of the structure shown in formula (a);
in formula (a): ring C and ring D each independently represent one of R "substituted or unsubstituted C5 to C30 aromatic ring, R" substituted or unsubstituted C3 to C30 heterocyclic ring, the substituted substituents in ring C and ring D are each independently unconnected, or adjacent 2 substituents are connected by a chemical bond to form a ring;
R 1 、R 2 、R 3 、R 1 、R 2 、R 3 wherein each of the substituted substituents, R 'and R' is independently selected from one or a combination of two of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl.
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, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are not repeated as shown above.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, the carbon number generally excludes the carbon number of a substituent.
In the present specification, the expression "-" of a ring structure indicates that the linking site is located at any position on the ring structure capable of bonding.
In the present specification, "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, unless otherwise specified, the expression of a chemical element generally includes the concept of its isotope, for example, the expression of "hydrogen (H)", and includes its isotope 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) then comprises 12 C、 13 C, etc., and are not described in detail.
Heteroatoms in the present invention generally refer to atoms or groups of atoms selected from N, O, S, P, si and Se, preferably selected from N, O, S.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present invention, unless otherwise specified, both aryl and heteroaryl include cases of single rings and condensed rings.
In the present invention, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and condensed ring aryl groups, preferably C6-C30 aryl groups, and more 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 saidPyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethyl fluorenyl, 9-dipropyl fluorenyl, 9-dibutyl fluorenyl 9, 9-dipentylfluorenyl, 9-dihexylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, 9' -spirobifluorene, and benzofluorenyl.
The C3-C60 heteroaryl groups mentioned in the present invention include monocyclic heteroaryl groups and condensed ring heteroaryl groups, preferably C3-C30 heteroaryl groups, further preferably C4-C20 heteroaryl groups, and still further preferably C5-C12 heteroaryl groups. Monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are linked by a single bond, and examples of the monocyclic heteroaryl group include: furyl, thienyl, pyrrolyl, pyridyl, and the like. Condensed ring heteroaryl means a group in which at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) are contained in a molecule and two adjacent atoms are fused together without being independent of each other. Examples of fused ring heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom in the above examples of the aryl group. The number of carbons of the arylene group includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, and the like. Specific examples of the heteroarylene group in the present invention include a divalent group obtained by removing one hydrogen atom in the above-mentioned heteroaryl group.
Examples of the aryloxy group in the present invention include monovalent groups composed of the above aryl group, heteroaryl group and oxygen.
In the present invention, an arylamino group represents a group formed by substituting hydrogen on an amino group with one or two aryl groups, wherein the attachment site of the arylamino group may be attached to an aryl group in the arylamino group or may be attached to N in the arylamino group, and exemplary carbon numbers and specific groups of the aryl group in the arylamino group are the same as those described above.
Examples of the C6-C30 arylamino group mentioned in the present invention include: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like.
Examples of the C3-C30 heteroarylamino group mentioned in the present invention include: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
The chain alkyl group mentioned in the present invention includes a straight chain alkyl group and a branched chain alkyl group unless otherwise specified. Specifically, the substituted or unsubstituted C1-C30 chain alkyl group is preferably a substituted or unsubstituted C1-C16 chain alkyl group, more preferably a substituted or unsubstituted C1-C10 chain alkyl group. Examples of the substituted or unsubstituted C1-C10 chain alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl and the like.
In the present invention, the cycloalkyl group includes a monocycloalkyl group and a multicycloalkyl group; wherein, monocycloalkyl refers to an alkyl group having a single cyclic structure; polycycloalkyl refers to a structure in which two or more cycloalkyl groups are formed by sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present specification, examples of the C1-C10 alkoxy group which is preferably substituted or unsubstituted C1-C20 alkoxy group, and which is preferably substituted or unsubstituted C1-C10 alkoxy group, may be given as follows: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.
In the present specification, as the substituted or unsubstituted C1-C20 silyl group, as the substituted or unsubstituted C1-C10 silyl group, a silyl group substituted with a group exemplified in the above-mentioned C1-C10 alkyl group may be exemplified, and specific examples thereof include: and methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, and the like.
It should be noted that the possible actions of the individual groups/features are described separately in the present application for convenience of explanation, but this does not mean that the groups/features are acting in isolation. In fact, the reason for obtaining good properties is essentially an optimal combination of the whole molecule, as a result of the synergy between the individual groups, rather than the effect of a single group.
Preferably, at least one of the rings a, B has a structure as shown in formula (B):
when the ring A is a structure shown in the formula (B), the ring A is connected with other parts of the formula (1) through a shared chemical bond c or a chemical bond d, and when the ring B is a structure shown in the formula (B), the ring B is connected with other parts of the formula (1) through the shared chemical bond c and the shared chemical bond d;
In formula (b), the Z 1 、Z 2 、Z 3 And Z 4 Are independently selected from CR 4 Or N, the R 4 Independently selected from hydrogen, halogen, unsubstituted or R 'substituted C1-C20 straight or branched alkyl, unsubstituted or R' substituted C3-C20 cycloalkyl, unsubstituted or R 'substituted C1-C20 alkoxy, unsubstituted or R' substituted C1-C20 alkylsilyl, unsubstituted or R 'substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R' substituted C6-C30 arylamino, unsubstitutedOr at least one of R 'substituted C3-C30 heteroarylamino, unsubstituted or R' substituted C6-C30 aryloxy, unsubstituted or R 'substituted C3-C30 heteroaryloxy, unsubstituted or R' substituted C6-C60 aryl, unsubstituted or R 'substituted C3-C60 heteroaryl, said two adjacent R' s 4 Are connected in a ring or are not connected;
r' is independently selected from one or two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl or C3-C60 heteroaryl.
Preferably, the organic compound of the present invention has a structure as shown in formula (1-1):
in the formula (1-1), X 1 、X 2 、X 3 、R 1 、R 2 、L 1 The definition of ring C and ring D are the same as in claim 1;
Z 1 、Z 2 、Z 3 and Z 4 Is defined as in formula (b), Z 1’ 、Z 2’ 、Z 3’ Definition of (1) and Z 1 、Z 2 、Z 3 And Z 4 Is the same as defined in the specification;
preferably, Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ Are independently selected from CR 4 Or N, the R 4 Selected from hydrogen, halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylAt least one of amino group, unsubstituted or R ' substituted C6-C30 aryloxy group, unsubstituted or R ' substituted C3-C30 heteroaryloxy group, unsubstituted or R ' substituted C6-C60 aryl group, unsubstituted or R ' substituted C3-C60 heteroaryl group, said two adjacent R ' s 4 Are connected in a ring or are not connected;
r' is independently selected from one or two of halogen, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkyl silicon base, cyano, nitryl, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C30 aryl and C3-C30 heteroaryl.
Preferably, in the formula (1) and the formula (1-1), X 1 、X 2 、X 3 Are independently selected from CR 3 And wherein at least one R 3 Is of the structure shown in formula (a);
preferably, in the formula (1) and the formula (1-1), X 1 、X 2 、X 3 Are independently selected from CR 3 And wherein at least one R 3 Is of the structure shown in formula (a), and the other two R 3 Is hydrogen;
still preferably, the X 2 Is CR (CR) 3 And R is 3 Is of the structure shown in formula (a), wherein X is 1 And X 3 Is CR (CR) 3 And R is 3 Is hydrogen.
Preferably, the organic compound of the present invention has a structure represented by the formula (1-2):
in the formula (1-2), Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、R 1 、R 2 、L 1 The definition of ring C and ring D are the same as those in formula (1-1);
preferably, L 1 Is a single bond
Preferably, R 1 And R is 2 Separately and independently from each otherOne selected from the group consisting of a substituted or unsubstituted C1-C20 linear or branched alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group;
preferably, R 1 And R is 2 Each independently selected from one of C1-C20 straight-chain or branched-chain alkyl and C3-C20 cycloalkyl;
more preferably, R 1 And R is 2 Each independently selected from one of methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl;
most preferably, R 1 And R is 2 Each independently selected from t-butyl or t-amyl.
Preferably, at least one of the rings C and D has a structure as shown in formula (C):
In formula (c), the Z 5 、Z 6 、Z 7 And Z 8 Are independently selected from CR 5 Or N, the R 5 Independently selected from hydrogen or one or two of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl, said two adjacent R 5 Are connected in a ring or are not connected;
preferably, the Z 5 、Z 6 、Z 7 And Z 8 Are independently selected from CR 5 ；
Still preferably, the Z 5 、Z 6 、Z 7 And Z 8 Are independently selected from CR 5 And the R is 5 One or two of hydrogen, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl;
more preferably, said Z 5 、Z 6 、Z 7 And Z 8 Are independently selected from CR 5 And the R is 5 Selected from hydrogen.
Preferably, the structure is represented by the following formula (1-3):
in the formula (1-3), R 1 、R 2 、L 1 Is the same as that in formula (1);
Z 1 、Z 2 、Z 3 、Z 4 、Z 1 ’、Z 2 ’、Z 3 ' each independently selected from CR 4 The R is 4 At least one selected from hydrogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, cyano, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, said two adjacent R ' s 4 Are connected in a ring or are not connected;
each R' is independently selected from one or two of C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 cyano, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
Preferably, the Z 2 、Z 2’ Are independently selected from CR 4 The R is 4 One selected from the group consisting of a substituted or unsubstituted C1-C10 linear or branched alkyl group, and a substituted or unsubstituted C3-C10 cycloalkyl group;
preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ Are independently selected from CR 4 And Z is 2 、Z 2’ Are respectively independent CR 4 R in (a) 4 One selected from the group consisting of a substituted or unsubstituted C1-C10 linear or branched alkyl group, and a substituted or unsubstituted C3-C10 cycloalkyl group;
still preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ Are independently selected from CR 4 And Z is 2 、Z 2’ Are respectively independent CR 4 R in (a) 4 One selected from the group consisting of a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, Z 1 、Z 3 、Z 4 、Z 1’ 、Z 3’ Are respectively independent CR 4 R in (a) 4 Is hydrogen;
most preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ Are independently selected from CR 4 And Z is 2 、Z 2’ Are respectively independent CR 4 R in (a) 4 Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl, Z 1 、Z 3 、Z 4 、Z 1’ 、Z 3’ Are respectively independent CR 4 R in (a) 4 Is hydrogen.
Still preferably, the organic compound of the present invention has a structure represented by the following formula (1-3-1):
most preferably, the organic compound of the present invention has a structure represented by the following formula (1-4-1), (1-4-2) or (1-4-3):
wherein R is 1 And R is 2 R is as defined in formulae (1-3) 41 、R 42 、R 41 ‘、R 42 ‘、R 41 ' and R 42 ' are defined as R 4 The definition is the same;
preferably, R 5 Has a structure as shown in formula (1-4-1).
Further, the organic compounds of the present invention may preferably be represented by the following specific structural compounds M1 to M102, which are merely representative and do not limit the scope of the present invention:
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the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification and is very suitable for industrial application.
Introduction of the inventive Compounds into L 1 The bonding makes the molecule have stronger rigidity and higher luminous efficiency, and the B atom para-carbazole can inhibit the molecule aggregation due to the steric hindrance effect, thereby being beneficial to the service life improvement, and simultaneously, the carbazole group has good hole transmission performance, has deeper HOMO energy level, can prevent carrier capture and is beneficial to the voltage reduction.
As another aspect of the present invention, there is also provided the use of a compound as described above in an organic electroluminescent device. In particular, the compound of the present invention has excellent light-emitting properties, can give triplet excitons to achieve high light-emitting efficiency, and is suitable for use as a light-emitting dye based on its excellent carrier transport efficiency.
Of course, since the compound of the present invention can also be used as a sensitizer to realize a good light-emitting layer together with a host material and a dye. Devices for which applications include, but are not limited to, organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners or electronic papers, preferably organic electroluminescent devices.
The invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and at least one or more luminescent functional layers interposed between the first electrode and the second electrode, wherein the luminescent functional layers contain at least one compound according to the invention.
The structure of the organic electroluminescent device is consistent with that of the existing device, for example, the organic electroluminescent device comprises an anode layer, a plurality of luminous functional layers and a cathode layer; the plurality of light-emitting functional layers include at least a light-emitting layer, wherein the light-emitting layer contains the above-described organic compound of the present invention.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel and display manufacturing enterprises on high-performance materials.
Detailed Description
The technical scheme of the invention is further more specifically described below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The compounds of the present invention may be obtained by known methods, for example, synthesized by known organic synthesis methods. Exemplary synthetic routes are given below, but may be obtained by other methods known to those skilled in the art.
Synthesis example 1
Synthesis of compound M1:
synthesis of intermediate M1-1:
starting material A (40 g,102.28 mmol), carbazole (17.1 g,102.28 mmol), pd 2 (dba) 3 (Tridibenzylideneacetone dipalladium) (4.68 g,5.11 mmol), P (tBu) 3 HF 4 (Tri-tert-butylphosphine tetrafluoroborate) (2.86 g,10.23 mmol), sodium t-butoxide (19.66 g,204.56 mmol) and toluene (500 ml) were put into a 1000ml three-necked flask, nitrogen was substituted 3 times, and the temperature was raised to 110℃for reaction for 5 hours.
Cooling the system to room temperature, spin-drying the solvent, performing silica gel sample column chromatography to obtain white solid, and recrystallizing with toluene and ethanol to obtain intermediate M1-145.1g.
Synthesis of intermediate M1-2:
m1-1 (40 g,83.79 mmol), bis (2-methylphenyl) amine (16.53 g,83.79 mmol), pd132 (bis (di-t-butyl-4-dimethylaminophosphine) palladium chloride) (2.97 g,4.19 mmol), sodium t-butoxide (16.11, 167.58 mmol), toluene (500 ml) were charged into a 1000ml three-necked flask, purged with nitrogen 3 times, and the temperature was raised to 100℃for 8 hours.
Cooling the system to room temperature, spin-drying the solvent, performing silica gel sample column chromatography to obtain a white solid, and recrystallizing with toluene and ethanol to obtain intermediate M1-250.64g.
Synthesis of product M1:
intermediate M1-2 (40 g,62.68 mmol) was added to a 2000ml three-necked flask, tert-butylbenzene (600 ml) was added, and after stirring for 20 minutes, the reaction system was cooled to 0℃and then tert-butyllithium (78.34 mL,1.6M,125.35 mmol) was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 60 ℃ and continuously heating for 2h. The reaction temperature was again lowered to 0℃and boron tribromide (47.1, 188.03 mmol) was added under nitrogen, followed by stirring for 10 minutes and then heating to 60℃for 30 minutes. Diisopropylethylamine (32.40, 250.70 mmol) was added thereto again by lowering the temperature of the system to 0℃and finally the reaction system was heated to 120℃for reaction for 12 hours.
After the reaction was cooled to room temperature, the organic phase was dried under reduced pressure. Column chromatography gave 9.1g of crude product and toluene/ethanol recrystallisation gave 8.3g. Mass spectrometry determines molecular ion mass: 611.56 (theory: 611.25).
Synthesis example 2
Synthesis of compound M3:
the synthesis method of the compound is identical to that of M1, except that the di (2-methylphenyl) amine is replaced by di (2-tert-butylphenyl) amine.
Synthesis example 3
Synthesis of compound M15:
the synthesis method of the compound is completely the same as that of M3, except that carbazole amine is replaced by 3, 6-di-tert-butylcarbazole.
Synthesis example 4
Synthesis of Compound M49:
the synthesis method of the compound is identical to that of M1, except that the raw material A is replaced by the raw material B.
Theoretical calculation
The invention adopts Gaussian03 to carry out quantum chemical calculation on the compounds, adopts a time-dependent density functional method to respectively carry out theoretical calculation on the compounds listed in table 1, and the calculation results are shown in table 1. The fluorescence emission wavelength of the material is related to the first singlet energy level, and the higher the energy level, the shorter the fluorescence emission wavelength of the material, and the more blue the luminescence.
The comparative compounds C1-C7 have the following structures:
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table 1: quantitative calculation of partial Compound and comparative Compound
| Numbering of compounds | S1/eV | Luminescence peak/nm | HOMO/eV | LUMO/eV |
| M1 | 2.85 | 435 | -5.0 | -1.4 |
| M3 | 2.84 | 437 | -5.0 | -1.4 |
| M15 | 2.83 | 438 | -5.0 | -1.5 |
| M49 | 2.85 | 435 | -4.9 | -1.3 |
| M63 | 2.85 | 435 | -4.9 | -1.3 |
| M98 | 2.83 | 438 | -5.0 | -1.4 |
| C2 | 2.79 | 444 | -4.7 | -1.5 |
| C4 | 2.79 | 444 | -4.7 | -1.4 |
| C6 | 2.78 | 446 | -4.7 | -1.4 |
| C7 | 2.73 | 454 | -4.5 | -1.3 |
Compared with the comparative compounds C2 and C4, the compound has more blue light color, which is mainly due to the fact that alkyl substitution on the C2 is positioned at the para position of N atom, the effect of improving HOMO energy level is achieved, and the molecular band gap is reduced, so that luminescence is red shifted. C4 has no alkyl substitution in the meta position of N atom, so that the HOMO energy level is shallow, and the luminescence is red shifted.
For compound C6, there is a certain red shift in the light color due to the greater degree of indenoindole conjugation.
For the compound C7, the B atom has no carbazole structure at the para position, so that the HOMO energy level is shallow, the band gap is small, and the light color is reddish.
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 through HI-3 described below; one or more compounds of HT-1 through HT-51 may also be used to dope one or more of HI-1 through 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 another aspect of the present invention, the luminescent layer employs a technique of thermally activating delayed fluorescence luminescence, the luminescent layer host material of which is selected from, but not limited to, one or more combinations of the following PH-1 to PH-85.
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The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or a combination of more of the TDE1-TDE49 listed below.
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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，Mg，Yb。
The preparation process of the organic electroluminescent device comprises the following steps:
device example 1 fabrication method: the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with anode in vacuum chamber, vacuumizing to <1×10 -5 Pa, vacuum thermal evaporation is carried out on the anode layer film sequentially, 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 transmission layer, 5nm of compound HT-14 is used as an electron blocking layer, 20nm of compound BFH-4:M1 (100:3, w/w) binary mixture is used as a light emitting layer, 5nm of ET-23 is used as a hole blocking layer, 25nm of compound ET-69:ET-57 (50/50, w/w) mixture is used as an electron transmission layer, 1nm of LiF is used as an electron injection layer, and 150nm of metal aluminum is used as a 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 2-12 were fabricated in the same manner as device example 1, except that the dopants in the light-emitting layer were different, and the specific dopant materials were as described in Table 2 below.
Device comparative example 1 was fabricated in the same manner as in device example 1, except that the dopant in the light-emitting layer was replaced with compound C5 in the related art.
The testing method of the device comprises the following steps:
the organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the external quantum efficiency of the OLED device was recorded at a luminance of 1000nit using the integrating sphere method.
The performance data of the organic electroluminescent devices prepared in the examples and comparative examples of the respective devices are shown in Table 2 below.
Table 2:
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from the results in Table 2, the compound of the present invention was incorporated into L relative to the compound C5 1 The bonding makes the molecule have stronger rigidity and higher luminous efficiency.
Device example 13 was fabricated in the same manner as in example 1, except that the electron blocking layer, the light emitting layer and the hole blocking layer were replaced as follows: a ternary mixture of 5nm of compound HT-51 as electron blocking layer, 40nm of compound PH-54:TDE23:M1 (100:40:1, w/w/w) as light emitting layer and 5nm of PH-28 as hole blocking layer.
Device examples 14-24 were fabricated in the same manner as device example 13, except that the dopants in the light-emitting layer were different, and the specific dopant materials were as described in Table 3 below.
Device comparative examples 2 to 7 were produced in the same manner as in device example 13 except that the dopants in the light-emitting layer were replaced with compounds C1, C2, C3, C5, C6 and C7 in the prior art, respectively.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving of the organic electroluminescent devices prepared in examples 13 to 24 and comparative example 7 was measured using a digital source meter and a luminance meter under the same luminance A voltage. 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 that time is the driving voltage;
table 3:
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the LT97 life of the organic electroluminescent devices prepared in examples 13 to 24 and comparative examples 2 to 6 was measured: measured at 40mA/cm using a luminance meter 2 The initial luminance value of the device at the current density was maintained at a constant current, and the time in hours for the luminance of the device to drop to 97% of the initial luminance was measured. The lifetime of device example 13 was set to 1.0, and the data for the remaining device examples and device comparative examples were all ratios thereto.
The performance data of the organic electroluminescent devices prepared in the examples and comparative examples of the respective devices are shown in Table 4 below.
Table 4:
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from the results of table 4, in the thermally activated sensitized fluorescent device, the compound of the present invention exhibited a longer lifetime relative to the compounds C1, C2 and C3, and the compound of the present invention exhibited a longer lifetime relative to the compounds C1 and C2, mainly because the carbazole at the para position of the B atom was not front-line orbital distribution, but the methyl group and the phenyl group on the carbazole were likely to undergo c—c bond cleavage during the operation of the device, adding an additional unstable factor.
Compared with the comparative compound C3, the compound provided by the invention has longer service life, which is mainly due to the fact that the polymethine substitution on the benzene ring causes larger steric hindrance, so that the mother nucleus structure is more distorted, and the stability of the compound is influenced.
The compounds according to the invention exhibit a longer lifetime than the comparative compound C5, possibly due to the compound L according to the invention 1 The presence of (C) enables higher C-N bond energies and less prone to cleavage.
Compared with a comparative compound C6, the indenoindole structure exists in the structure, and the methyl in the indenoindole structure is easy to decompose in the evaporation plating and device working processes, so that the service life is poor;
hole trapping tends to occur due to the shallower HOMO level of C7 relative to the comparative compound C7, resulting in a higher device voltage. The above results prove that the compound of the present invention is a fluorescent guest material with good performance.
The foregoing description of the embodiments has been provided for the purpose of illustrating the general principles of the invention, and is not meant to limit the invention thereto, but to limit the invention thereto, and any modifications, equivalents, improvements and equivalents thereof may be made without departing from the spirit and principles of the invention.
Claims (13)
1. A boron-nitrogen-containing organic compound has a structure shown in a general formula (1):
in the formula (1):
ring A and ring B each independently represents one of a substituted or unsubstituted C5-C60 aromatic ring and a substituted or unsubstituted C3-C60 heterocyclic ring;
the substituents in ring A and ring B are each independently selected from at least one of halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, the substituents in ring A and ring B are each independently unconnected, or 2 adjacent substituents are linked through a chemical bond to form a ring;
R 1 and R is 2 Each independently selected from one of a substituted or unsubstituted C1-C20 straight or branched chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C3-C60 heteroarylamino group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C3-C30 heteroaryloxy group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group;
L 1 Selected from single bond, CR 1 R 2 An O atom, an S atom, NR 3 One of the following;
R 1 、R 2 and R is 3 Each independently selected from one of a substituted or unsubstituted C1-C20 straight or branched chain alkyl, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C6-C60 aryl, and a substituted or unsubstituted C3-C60 heteroaryl;
X 1 、X 2 、X 3 are independently selected from CR 3 Or N, the R 3 Independently 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, takenOne of substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; the adjacent two R' s 3 Are connected in a ring or are not connected;
the X is 1 、X 2 、X 3 At least one of them is CR 3 And the R is 3 Is of the structure shown in formula (a);
in formula (a): ring C and ring D each independently represent one of R "substituted or unsubstituted C5 to C30 aromatic ring, R" substituted or unsubstituted C3 to C30 heterocyclic ring, the substituted substituents in ring C and ring D are each independently unconnected, or adjacent 2 substituents are connected by a chemical bond to form a ring;
R 1 、R 2 、R 3 、R 1 、R 2 、R 3 Wherein each of the substituted substituents, R 'and R' is independently selected from one or a combination of two of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl.
2. The organic compound according to claim 1, wherein at least one of the rings a, B has a structure represented by formula (B):
when the ring A is a structure shown in the formula (B), the ring A is connected with other parts of the formula (1) through a shared chemical bond c or a chemical bond d, and when the ring B is a structure shown in the formula (B), the ring B is connected with other parts of the formula (1) through the shared chemical bond c and the shared chemical bond d;
in formula (b), the Z 1 、Z 2 、Z 3 And Z 4 Are independently selected from CR 4 Or N, the R 4 Independently selected from hydrogen, halogen, and not takenAt least one of substituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, said two adjacent R 4 Are connected in a ring or are not connected;
r' is independently selected from one or two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl or C3-C60 heteroaryl.
3. The organic compound according to claim 2, which has a structure represented by the formula (1-1):
in the formula (1-1), X 1 、X 2 、X 3 、R 1 、R 2 、L 1 The definition of ring C and ring D are the same as in claim 1;
Z 1 、Z 2 、Z 3 and Z 4 Is defined as in formula (b), Z 1’ 、Z 2’ 、Z 3’ Definition of (1) and Z 1 、Z 2 、Z 3 And Z 4 Is the same as defined in the specification;
preferably, Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ Are independently selected from CR 4 Or N, the R 4 At least one selected from the group consisting of hydrogen, halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, said two adjacent R 4 Are connected in a ring or are not connected;
r' is independently selected from one or two of halogen, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkyl silicon base, cyano, nitryl, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C30 aryl and C3-C30 heteroaryl.
4. An organic compound according to any one of claims 1 to 3, wherein X is 1 、X 2 、X 3 Are independently selected from CR 3 And wherein at least one R 3 Is of the structure shown in formula (a);
preferably, the X 1 、X 2 、X 3 Are independently selected from CR 3 And wherein at least one R 3 Is of the structure shown in formula (a), and the other two R 3 Is hydrogen;
still preferably, the X 2 Is CR (CR) 3 And R is 3 Is of the structure shown in formula (a), wherein X is 1 And X 3 Is CR (CR) 3 And R is 3 Is hydrogen.
5. The organic compound according to claim 3, which has a structure represented by the formula (1-2):
in the formula (1-2), Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、R 1 、R 2 、L 1 The definition of ring C and ring D are the same as those in formula (1-1);
preferably, L 1 Is a single bond.
6. An organic compound according to any one of claims 1 to 5, wherein R 1 And R is 2 Each independently selected from one of a substituted or unsubstituted C1-C20 straight or branched chain alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group;
preferably, R 1 And R is 2 Each independently selected from one of C1-C20 straight-chain or branched-chain alkyl and C3-C20 cycloalkyl;
more preferably, R 1 And R is 2 Each independently selected from one of methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl;
most preferably, R 1 And R is 2 Each independently selected from t-butyl or t-amyl.
7. The organic compound according to claim 5, wherein at least one of the ring C and the ring D has a structure represented by formula (C):
in formula (c), the Z 5 、Z 6 、Z 7 And Z 8 Are independently selected from CR 5 Or N, the R 5 Independently selected from hydrogen or halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-to-COne or two of C20 alkyl silicon group, C6-C30 aryl amino group, C3-C30 heteroaryl amino group, C6-C30 aryloxy group, C3-C30 heteroaryl oxy group, C6-C60 aryl group or C3-C60 heteroaryl group, wherein two adjacent R 5 Are connected in a ring or are not connected;
Preferably, the Z 5 、Z 6 、Z 7 And Z 8 Are independently selected from CR 5 ；
Still preferably, the Z 5 、Z 6 、Z 7 And Z 8 Are independently selected from CR 5 And the R is 5 Selected from hydrogen or one or two of C1-C20 straight chain or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl or C3-C60 heteroaryl;
more preferably, said Z 5 、Z 6 、Z 7 And Z 8 Are independently selected from CR 5 And the R is 5 Selected from hydrogen.
8. The organic compound according to claim 7, which has a structure represented by the following formula (1-3):
in the formula (1-3), R 1 、R 2 、L 1 Is the same as that in formula (1);
Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ are independently selected from CR 4 The R is 4 At least one selected from hydrogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, cyano, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl, said two adjacent R ' s 4 Are connected in a ring or are not connected;
each R' is independently selected from one or two of C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 cyano, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
9. The organic compound according to claim 8, wherein Z 2 、Z 2’ Are independently selected from CR 4 The R is 4 One selected from the group consisting of a substituted or unsubstituted C1-C10 linear or branched alkyl group, and a substituted or unsubstituted C3-C10 cycloalkyl group;
preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ Are independently selected from CR 4 And Z is 2 、Z 2’ Are respectively independent CR 4 R in (a) 4 One selected from the group consisting of a substituted or unsubstituted C1-C10 linear or branched alkyl group, and a substituted or unsubstituted C3-C10 cycloalkyl group;
still preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ Are independently selected from CR 4 And Z is 2 、Z 2’ Are respectively independent CR 4 R in (a) 4 One selected from the group consisting of a substituted or unsubstituted C1-C10 chain alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, Z 1 、Z 3 、Z 4 、Z 1’ 、Z 3’ Are respectively independent CR 4 R in (a) 4 Is hydrogen;
most preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ Are independently selected from CR 4 And Z is 2 、Z 2’ Are respectively independent CR 4 R in (a) 4 Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl, tert-pentyl, cyclopropyl, cyclopentyl or cyclohexyl, Z 1 、Z 3 、Z 4 、Z 1’ 、Z 3’ Are respectively and independently CR 4 R in (a) 4 Is hydrogen.
10. The organic compound according to claim 8 or 9, which has a structure represented by the following formula (1-3-1):
preferably, it has a structure represented by the following formula (1-4-1), (1-4-2) or (1-4-3):
Wherein R is 1 And R is 2 R is as defined in formulae (1-3) 41 、R 42 、R 41‘ 、R 42‘ 、R 41‘’ And R is 42‘’ Are all as defined in R 4 The definition is the same;
preferably, the structure is as shown in formula (1-4-1).
11. The organic compound according to claim 1, having the structure shown below:
12. use of an organic compound according to any one of claims 1 to 11 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.
13. 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 11;
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 11.
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