CN114478593A - Boron-containing organic compound and organic electroluminescent device containing same - Google Patents
Boron-containing organic compound and organic electroluminescent device containing same Download PDFInfo
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- CN114478593A CN114478593A CN202011160022.6A CN202011160022A CN114478593A CN 114478593 A CN114478593 A CN 114478593A CN 202011160022 A CN202011160022 A CN 202011160022A CN 114478593 A CN114478593 A CN 114478593A
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- Prior art keywords
- substituted
- unsubstituted
- ring
- alkyl
- boron
- Prior art date
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- 229910052796 boron Inorganic materials 0.000 title claims abstract description 30
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 39
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 31
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 30
- 150000002367 halogens Chemical class 0.000 claims abstract description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
- 125000001424 substituent group Chemical group 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 7
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 4
- -1 cyano, hydroxyl Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000001769 aryl amino group Chemical group 0.000 claims description 11
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000006539 C12 alkyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 9
- 125000004429 atom Chemical group 0.000 abstract description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 2
- 229910052805 deuterium Inorganic materials 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 53
- 150000001875 compounds Chemical class 0.000 description 52
- 239000000463 material Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000021615 conjugation Effects 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001793 charged compounds Chemical class 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 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
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel 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
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- GMVJKSNPLYBFSO-UHFFFAOYSA-N 1,2,3-tribromobenzene Chemical compound BrC1=CC=CC(Br)=C1Br GMVJKSNPLYBFSO-UHFFFAOYSA-N 0.000 description 1
- SSPNOMJZVHXOII-UHFFFAOYSA-N 1,3-dibromo-5-tert-butylbenzene Chemical compound CC(C)(C)C1=CC(Br)=CC(Br)=C1 SSPNOMJZVHXOII-UHFFFAOYSA-N 0.000 description 1
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-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
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000012863 analytical testing Methods 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 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
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 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
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002605 large molecules Chemical class 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
- 229920002521 macromolecule Polymers 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 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
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 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
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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Abstract
A boron-containing organic compound having a structure represented by (1):
the ring X, the ring Y and the ring Z are respectively selected from a substituted or unsubstituted 6-30-membered aromatic ring or a substituted or unsubstituted 4-30-membered aromatic heterocyclic ring; ar (Ar)1～Ar2Each selected from C6-C30 aryl, or C3-C30 heteroaryl; ra、RbAnd RnEach independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, C1-C12 alkoxy, substituted or unsubstituted C3-C30 heteroaryl, and the like; and the following conditions are satisfied: at Ar1、Ar2In X and Y, Ar1A substituent being present ortho to the linking site with the N atom and ortho to the linking site of X with the N atom, or Ar2And substituents are arranged at the ortho position of the connecting position of the N atom and the ortho position of the connecting position of the Y atom and the N atom, and the substituents are selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C12 aryl and substituted or unsubstituted C3-C12 heteroaryl.
Description
Technical Field
The invention relates to a B-N organic luminescent material, in particular to a boron-containing organic compound for an organic electroluminescent device and application thereof in the organic electroluminescent device.
Background
At present, opto-electronic devices based on organic materials are becoming more and more popular. Organic electroluminescent diodes (OLEDs), as emerging reality and lighting technologies, have many advantages such as being foldable, rollable, high resolution, self-luminescent, bright in color, low power consumption, etc.
In the field of display and illumination, the device structure of OLEDs is generally composed of functional materials such as injection materials, transport materials, and light emitting materials, and the light emitting layer is generally used by using blue (B) fluorescence in combination with red (R) and green (G) phosphorescence materials.
Recently, TADF (Thermally Activated Delayed Fluorescence) organic luminescent materials based on B-N resonance type (adv. mater.2016, 28, 2777-. Compared with phosphorescent dyes, when the compounds are doped into a main material, the compounds have the advantages of high electroluminescent efficiency, narrow spectrum, high color purity and the like, do not contain metal, and are simple to synthesize and low in price.
Disclosure of Invention
Problems to be solved by the invention
However, the conventional boron-nitrogen resonance type compound, due to the increase of the degree of conjugation thereof, is not suitable for the development of mass-produced devices because the temperature at the time of vapor deposition of the device is high and the emission color is significantly red-shifted. Therefore, there is a need to develop a material system that is favorable for evaporation of devices and has excellent chromaticity to meet the commercial requirement.
Means for solving the problems
In order to solve the above problems in the prior art, the inventors have intensively studied and found that introduction of a steric hindrance group into a specific position in a molecular skeleton can effectively reduce conjugation of a molecule, lower a sublimation temperature, and blue-shift a light color.
Specifically, the present invention provides a boron-containing organic compound characterized by having a structure represented by (1):
wherein, ring X, ring Y and ring Z are each independently selected from a substituted or unsubstituted 6-to 30-membered aromatic ring or a substituted or unsubstituted 4-to 30-membered aromatic heterocyclic ring, preferably a substituted or unsubstituted 6-to 8-membered aromatic ring or a substituted or unsubstituted 5-to 8-membered aromatic heterocyclic ring, more preferably a substituted or unsubstituted benzene or a substituted or unsubstituted 6-membered aromatic heterocyclic ring;
when the ring X, the ring Y or the ring Z has a substituent, the substituent is selected from one of halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C1 to C12 alkoxy, substituted or unsubstituted C1 to C12 silyl, substituted or unsubstituted C6 to C30 arylamino, substituted or unsubstituted C3 to C30 heteroarylamino, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl;
Ar1～Ar2each independently selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
and the following conditions are satisfied:
the following conditions are satisfied:
at Ar1、Ar2In ring X and ring Y, Ar1At least one position ortho to the linking site of the N atom and ortho to the linking site of the ring X and the N atom, and/or, Ar2At least one position ortho to the linking position with the N atom and ortho to the linking position of ring Y with the N atom is substituted with one selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
when the substituted or unsubstituted group has a substituent, the substituent is selected from one or a combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.
According to the invention, a group with a certain steric hindrance effect is introduced at the ortho position of two aromatic rings connected with a certain N atom in the formula (1), so that the conjugation of molecules can be effectively reduced, the sublimation temperature is reduced, and the light color of the material is adjusted, so that the emission wavelength of the molecules is blue-shifted. The two aromatic rings introduced with a certain group may be respectively positioned at X and Ar1In (corresponding to the left N in formula (1)), may also be located in Y and Ar, respectively2(corresponds to the right N in the formula (1)).
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
In the present specification, the expression of Ca to Cb means that the group has carbon atoms of a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified.
In the present specification, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can form a bond.
In the present specification, "independently" means that the subject may be the same or different when a plurality of subjects are provided.
In the present invention, unless otherwise specified, the expression of a chemical element generally includes the concept of its isotope, for example, the expression "hydrogen (H)" includes the concept of its isotope 1H (protium or H), 2H (deuterium or D); carbon (C) includes 12C, 13C, etc., and will not be described again.
The hetero atom in the present invention generally refers to an atom or group of atoms selected from N, O, S, P, Si and Se, preferably N, O, S.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present invention, the monocyclic aryl group means that one or at least two phenyl groups are contained in a molecule, and when the at least two phenyl groups are contained in a molecule, the phenyl groups are independent of each other and are connected by a single bond, such as phenyl, biphenylyl, terphenylyl, and the like, for example; the fused ring aryl group means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are fused with each other, and exemplified by naphthyl, anthryl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl refers to a fused ring of at least one phenyl group and at least one heteroaryl group, or, fused ring of at least two heteroaryl rings, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.
In the present specification, examples of the 6 to 8-membered aromatic ring include: benzene rings, and the like.
In the present specification, the aryl group includes concepts of a monocyclic aryl group and a condensed ring aryl group, and examples of the C6 to C30 aryl group include: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, anthryl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecylindenyl, spirotrimeric indenyl, spiroisotridecylindenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; terphenyl 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; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene. C6-C30 arylene is similar to C6-C30 aryl, provided that the above groups are changed to the corresponding subunits.
In the present specification, heteroaryl includes the concept of monocyclic heteroaryl and fused heteroaryl, and examples of the heteroaryl group of C3 to C30 include: nitrogen-containing heteroaryl, oxygen-containing heteroaryl, sulfur-containing heteroaryl, and the like, and specific examples thereof include: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, indolyl, benzimidazolyl, indazolyl, imidazopyridinyl, benzotriazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl, benzisothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzofuranyl, dibenzothienyl, piperidyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like are preferred among them, pyridyl, dibenzofuranyl, piperidyl, pyrrolidinyl, piperazinyl, morpholinyl, phenazinyl, phenothiazinyl, phenoxazinyl, and the like, Dibenzothienyl radical.
Specific examples of the arylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the aryl group. Specific examples of the heteroarylene group in the present invention include divalent groups obtained by removing one hydrogen atom from the above-mentioned examples of the heteroaryl group.
Examples of the aryloxy group in the present invention include monovalent groups composed of the above aryl group, heteroaryl group and oxygen.
Examples of the C6-C30 arylamino group in the present invention include: phenylamino, methylphenylamino, naphthylamino, anthrylamino, phenanthrylamino, biphenylamino and the like.
Examples of the heteroarylamino group having C3 to C30 in the present invention include: pyridylamino, pyrimidylamino, dibenzofuranylamino and the like.
In the present specification, examples of the C1-C12 alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecane, dodecane, and the like, wherein methyl, ethyl, n-propyl, isopropyl, tert-butyl, sec-butyl, isobutyl, isopentyl, and methyl are preferred.
In the present specification, examples of the C1 to C12 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutyloxy, isopentyloxy, more preferably methoxy, are preferred.
In the present specification, examples of the cycloalkyl group having from C3 to C12 include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like, with cyclopropyl being preferred.
The boron-containing organic compound of the present invention preferably has a structure represented by (2):
wherein, X1～X6Each independently selected from CReOr N, and Y1～Y3Each independently selected from CRfOr N;
Reand RfEach independently selected from hydrogen, halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C388 silyl, substituted or unsubstituted C6-C3526 aryl, and substituted or unsubstituted COr one of unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
R1and R2Each independently selected from one of hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
In the boron-containing organic compound, the tension is lower when the ring X, the ring Y and the ring Z are six-membered rings respectively, and the molecular stability is better.
The boron-containing organic compound of the present invention preferably has a structure represented by (3):
wherein R isa、RbAnd RnRepresents one substituent group to the maximum permissible substituent group, and is respectively and independently selected from hydrogen, halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
R1and R2Each independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar1at least one position ortho to the linking position of the N atom and Ar2At least one position ortho to the position of attachment to the N atom is independently substituted with a group selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroarylIs substituted by one of the above.
In the invention, groups with certain steric hindrance effect such as alkyl or halogen are simultaneously introduced on two aromatic rings (corresponding to X and Y in the formula (1)) which form a ring with the B atom, so that the conjugation of the molecule can be further effectively reduced, the sublimation temperature is further reduced, and the emission wavelength of the molecule is further blue-shifted.
Among the above boron-containing organic compounds of the present invention, Ar is preferred1At least one position ortho to the linking position of the N atom and Ar2At least one position ortho to the connecting position with the N atom is independently substituted by one selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, preferably independently substituted by substituted or unsubstituted C1-C12 alkyl, halogen or phenyl, more preferably substituted by methyl.
The invention is further directed to Ar attached to the N atom1And Ar2Meanwhile, a group with a certain steric hindrance effect is introduced, so that the conjugation of molecules can be further reduced, the blue shift of the emission wavelength of the molecules is realized, the vibration and rotation of the molecules are inhibited, and the luminous efficiency is improved.
The boron-containing organic compound of the present invention is more preferably represented by the structure (4):
wherein R iscAnd RdIndependently represent a single substituent to the maximum permissible substituent, each independently selected from one of hydrogen, halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
R1～R4each independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, preferably each independently selected from substituted or unsubstituted C1-C12 alkyl, halogen or phenyl, more preferably methyl, is beneficial to blue shift of light color and increase of luminous efficiency. When R in the invention is1～R4When the organic silicon compound is steric hindrance groups, the molecules are higher in rigidity and higher in luminous efficiency.
In the above boron-containing organic compound of the present invention, Ra、Rb、Rc、Rd、Re、RfAnd RnEach independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, or substituted or unsubstituted C3-C12 cycloalkyl, preferably each independently selected from hydrogen or a substituted or unsubstituted one of the following structures:
more preferably Ra、Rb、Rc、Rd、Re、RfAnd RnEach independently selected from hydrogen, methyl or tert-butyl, especially Ra、RbHas good photochromic effect when hydrogen is used, and is beneficial to prolonging the service life of the device.
By adding Ra、Rb、Rc、Rd、Re、RfAnd RnOne or more of the above-mentioned groups can be preferably selected so that the size of the introduced group is more suitable, and the generated steric hindrance effect is more favorable for lowering the sublimation temperature and blue-shifting the emission wavelength of the molecule.
The above-mentioned compounds of the present invention are preferably selected from the structures represented by the following M1 to M101, but these compounds are merely representative:
the invention also relates to the application of the boron-containing organic compound in an organic electroluminescent device. The above boron-containing organic compound may be used as, but not limited to, a light-emitting layer material in an organic electroluminescent device.
The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and a plurality of organic layers interposed between the first electrode and the second electrode, characterized in that at least one of the organic layers contains the above-mentioned compound of the present invention.
Effects of the invention
According to the invention, groups with certain steric hindrance effect, such as alkyl or halogen, are introduced on the aromatic ring which is in ring formation with the B atom and at the ortho-position of the aromatic ring connected with the N atom, so that the conjugation of molecules can be effectively reduced, the sublimation temperature is reduced, and simultaneously the light color of the material can be adjusted, so that the emission wavelength of the molecules is blue-shifted.
Detailed Description
In order to make those skilled in the art better understand the present invention, the following will describe the specific preparation method of the above compound of the present invention by taking several synthetic examples as examples, but the preparation method of the present invention is not limited to these several synthetic examples, and those skilled in the art can make any modification, equivalent substitution, improvement, etc. without departing from the principle of the present invention, and extend the method to the scope of the technical scheme of the present invention as claimed in the claims.
Solvents and reagents used in the preparation method of the present invention, such as methylene chloride, petroleum ether, ethanol, tetrahydrofuran, N-dimethylacetamide, anhydrous magnesium sulfate, carbazole, benzimidazole, and other chemical reagents, can be purchased from domestic chemical product markets, such as from national drug group reagent company, TCI company, shanghai bibi pharmaceutical company, carbofuran reagent company, and the like. The compounds of the synthetic processes not mentioned in the present invention are either starting products obtained commercially or are prepared by these starting products according to known methods. Analytical testing of intermediates and compounds in the present invention uses an abciex mass spectrometer (4000 QTRAP).
Synthesis example 1: synthesis of Compound M1
Synthesis of intermediate M1-1:
to a 2L single-neck flask was added 2-bromotoluene (50g, 292mmol), 2-bromoaniline (37.6g, 351mmol), Pd (dppf) Cl at room temperature2(4.4g, 6mmol), S-Phos (4.9g, 12mmol), sodium t-butoxide (38.4g, 400mmol) and 1200mL of dry toluene were purged with nitrogen 3 times and then heated under reflux overnight. After the reaction had ended, the reaction mixture was washed with copious amounts of water, the organic phases were combined and dried, concentrated and chromatographed (PE: DCM 100: 1) to give 45g of the product as a pale yellow oil. Mass spectrometric analysis determined molecular ion mass: 197.12 (theoretical value: 197.12).
Synthesis of intermediate M1-2:
m1-1(9.8g, 50mmol), M-dibromobenzene (4.7g, 20mmol), Pd were added at room temperature2(dba)3(0.43g, 0.47mmol), s-Phos (0.38g, 0.94mmol), sodium t-butoxide (6.8g, 70mmol), xylene (200ml) were charged in a 500ml single-necked flask, replaced with nitrogen three times, and heated to 130 ℃ for reaction overnight. The reaction mixture is cooled to room temperature, extracted with ethyl acetate, washed with copious amounts of water, the organic phase is dried and concentrated by column chromatography (PE: DCM 50: 1) to give 8.5g of a white solid. Mass spectrometric analysis determined molecular ion mass: 468.26 (theoretical value)：468.26)。
Synthesis of compound M1:
m1-2(4.7g, 10mmol) was added to a 500ml three-necked flask, p-tert-butylbenzene (100ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃, and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to minus 20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and chromatographed (PE: DCM 100: 1) to give 2.8g of crude product, which is recrystallized from toluene/n-hexane to give 1.0g of a yellow solid. Mass spectrometric analysis determined molecular ion mass: 476.24 (theoretical value: 476.24).
Synthesis example 2: synthesis of Compound M22
The synthesis method is similar to that of M1, except that M-dibromobenzene in the second step is changed into 1, 3-dibromo-5-tert-butylbenzene, and finally column chromatography is carried out to obtain 2.6g of light yellow crude product, and then 0.8g of yellow solid M29 is obtained by recrystallization from toluene/n-hexane. Mass spectrometric analysis determined molecular ion mass: 532.32 (theoretical value: 532.30).
Synthesis example 3: synthesis of Compound M66
Synthesis of intermediate M66-1:
m1-1(13.8g, 70mmol), tribromobenzene (6.2g, 20mmol), Pd was added at room temperature2(dba)3(0.55g, 0.6mmol), s-Phos (0.49g, 1.2mmol), sodium t-butoxide (7.7g, 80mmol), xylene (250ml) were added to a 500ml single-neck flask, replaced with nitrogen three times, and heated to 130 ℃ for reaction overnight. Cooling the reaction solution to room temperature, extracting with ethyl acetate, washing with a large amount of water, and preparing an organic solutionAfter drying, the phases are concentrated and subjected to column chromatography (PE: DCM ═ 20: 1) to give 11.5g of crude product, which is recrystallized from toluene/ethanol to give 9.4g of a white solid. Mass spectrometric analysis determined molecular ion mass: 663.36 (theoretical value: 663.36).
Synthesis of compound M66:
m66-1(6.6g, 10mmol) was added to a 500ml three-necked flask, p-tert-butylbenzene (100ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and chromatographed (PE: DCM 50: 1) to give 3.8g of crude product, which is recrystallized from toluene/n-hexane to give 1.4g of a yellow solid. Mass spectrometric analysis determined molecular ion mass: 671.35 (theoretical value: 671.35).
Device embodiments
The present invention also provides an organic electronic light emitting device comprising the above-described example compound. An example of using an OLED as an embodiment of the organic electronic light emitting device is illustrated below. The OLED of the present embodiment includes first and second electrodes, 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 a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, 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 used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination 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 containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, 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 compounds shown below in HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI1-HI3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI1-HI3 described below.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs a thermally activated delayed fluorescence emission technique. The host material of the light-emitting layer is selected from, but not limited to, one or more of the combinations of PH-1 to PH-85.
In one aspect of the invention, the light-emitting layer employs a thermally activated delayed fluorescence emission technique. The fluorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of TDE1-TDE37 listed below.
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 be, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above; mixtures of one or more compounds from HT-1 to HT-51 and one or more compounds from PH-47 to PH-77 may also be used, 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, the combination of one or more of ET-1 through ET-65 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer can adopt, but is not limited to, one or more compounds of ET-1 to ET-65 or one or more compounds of PH-1 to PH-46; mixtures of one or more compounds from ET-1 to ET-65 with one or more compounds from PH-1 to PH-46 may also be used, but are not limited thereto.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ，LiF，NaCl，CsF，Li2O，Cs2CO3，BaO，Na，Li，Ca，Yb，Mg。
The effect of the synthesized boron-containing organic compound of the present invention as a material for a light emitting layer in a device is described in detail by examples 1 to 5 and comparative examples 1 to 2 below.
The fabrication of device example 1 was as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 1 × 10-5Pa, performing vacuum thermal evaporation on the anode layer film in sequence to obtain a 10nm HT-4: HI-3(97/3, w/w) mixture as a hole injection layer, a 60nm compound HT-4 as a hole transport layer and a 5nm compound HT-14 as an electron blocking layer; a binary mixture of 20nm compounds BFH-4: M1 (100: 3, w/w) as a luminescent layer, wherein M1 is a luminescent dye(ii) a ET-23 at 5nm as hole blocking layer, ET-61: ET-57(50/50, w/w) mixture of compounds at 25nm as electron transport layer, LiF at 1nm as electron injection layer, and metallic aluminum at 150nm as cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
Examples 2 to 15 and comparative examples 1 to 2
Examples 2 to 15 and comparative examples 1 to 2 were fabricated by the same procedure as in example 1 except that the light-emitting dye M1 in the light-emitting layer was replaced with the corresponding compound in table 1, respectively, to give organic electroluminescent devices of examples 2 to 15 and comparative examples 1 to 2.
Wherein the structural formulas of C1 and C2 are as follows:
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the current efficiencies of the organic electroluminescent devices prepared in examples 1 to 15 and comparative examples 1 to 2 were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2Current density of time; the ratio of the luminance to the current density is the current efficiency.
TABLE 1
As can be seen from Table 1, when the compounds of examples 1 to 15 of the device of the present invention were used as dyes, the emission wavelength was blue-shifted, the efficiency was improved, and excellent device properties were exhibited, as compared with the compounds of comparative examples 1 to 2 of the device. The principle is not clear, but the following is presumed: compared with the compounds of comparative examples 1-2 of devices, because the compounds of the invention introduce alkyl equipotential groups at specific positions, the conjugation degree of molecules is reduced, the blue shift of emission spectrum is realized, and meanwhile, the vibration rotation of molecules is inhibited, and the luminous efficiency is improved, which is beneficial to the practical application of the compounds of the invention.
Furthermore, the inventors have found that examples 5, 9, 11, and 12 have slightly lower blue-shift of the emission spectra than other examples, and the difference between them is mainly that: in the compounds of examples 5, 9, 11, 12, steric hindrance groups were simultaneously introduced into ortho positions of two benzene rings to which only one N atom was bonded, and it was thus presumed that: in the compound represented by the formula (3) of the present invention, R1～R4All the steric hindrance groups are more favorable for improving the blue shift degree of an emission spectrum.
The inventors also found that the compound of example 14, when used as a dye, has a lower current efficiency and a lower degree of blue shift than the compound of example 1, and the principle thereof is not clear, but the following is presumed: in the compound of example 1, the aromatic ring forming a ring with an N atom is a benzene ring, while in the compound of example 14, the corresponding is a pyridine ring, and thus it is inferred that: in the compound represented by the formula (1), when ring X or ring Y is a benzene ring, it is more advantageous for improving the luminous efficiency and the degree of blue shift.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. A boron-containing organic compound characterized by having a structure represented by (1):
wherein, ring X, ring Y and ring Z are each independently selected from a substituted or unsubstituted 6-to 30-membered aromatic ring or a substituted or unsubstituted 4-to 30-membered aromatic heterocyclic ring, preferably a substituted or unsubstituted 6-to 8-membered aromatic ring or a substituted or unsubstituted 6-to 8-membered aromatic heterocyclic ring, more preferably a substituted or unsubstituted benzene or a substituted or unsubstituted 6-membered aromatic heterocyclic ring;
when the ring X, the ring Y or the ring Z has a substituent, the substituent is selected from one of halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C1 to C12 alkoxy, substituted or unsubstituted C1 to C12 silyl, substituted or unsubstituted C6 to C30 arylamino, substituted or unsubstituted C3 to C30 heteroarylamino, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl;
Ar1～Ar2each independently selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
and the following conditions are satisfied: at Ar1、Ar2In ring X and ring Y, Ar1At least one position ortho to the linking site of the N atom and ortho to the linking site of the ring X and the N atom, and/or, Ar2At least one position ortho to the linking position with the N atom and ortho to the linking position of ring Y with the N atom is substituted with one selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
when the substituted or unsubstituted group has a substituent, the substituent is selected from one or a combination of at least two of halogen, cyano, hydroxyl, nitro, amino, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.
2. The boron-containing organic compound according to claim 1, wherein the boron-containing organic compound has a structure represented by (2):
wherein, X1～X6Each independently selected from CReOr N, and Y1～Y3Each independently selected from CRfOr N;
Reand RfEach independently selected from one of hydrogen, halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
R1and R2Each independently selected from one of hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
3. The boron-containing organic compound according to claim 1 or 2, wherein the boron-containing organic compound has a structure represented by (3):
wherein R isa、RbAnd RnRepresents one substituent group to the maximum permissible substituent group, and is respectively and independently selected from hydrogen, halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
R1and R2Each independently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Ar1at least one position ortho to the linking position of the N atom and Ar2At least one position ortho to the connecting position with the N atom is independently substituted by one selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
4. The boron-containing organic compound according to claim 1 or 2, wherein Ar is Ar1At least one position ortho to the linking position of the N atom and Ar2At least one position ortho to the connecting position with the N atom is independently substituted by one selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, preferably independently substituted by substituted or unsubstituted C1-C12 alkyl, halogen or phenyl, more preferably substituted by methyl.
5. The boron-containing organic compound of claim 3, wherein R isa、RbAnd RnEach independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, or substituted or unsubstituted C3-C12 cycloalkyl, preferably each independently selected from hydrogen or a substituted or unsubstituted one of the following structures:
more preferably Ra、RbAnd RnEach independently selected from hydrogen, methyl or tert-butyl.
6. The boron-containing organic compound according to claim 1 or 2, wherein the boron-containing organic compound has a structure represented by (4):
wherein R isa、Rb、Rn、RcAnd RdIndependently represent a single substituent to the maximum permissible substituent, each independently selected from one of hydrogen, halogen, cyano, hydroxyl, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 silyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
R1～R4each independently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, halogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, preferably each independently selected from substituted or unsubstituted C1-C12 alkyl, halogen, or phenyl, more preferably methyl.
7. The boron-containing organic compound of claim 6, wherein R isa、Rb、Rc、RdAnd RnEach independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, or substituted or unsubstituted C3-C12 cycloalkyl, preferably Ra、Rb、Rc、RdAnd RnEach independently selected from hydrogen or a substituted or unsubstituted one of the following structures:
more preferably Ra、Rb、Rc、RdAnd Rn are each independently selected from hydrogen, methyl or tert-butyl, further preferably Ra、Rb、Rc、RdAnd RnIs hydrogen.
8. The boron-containing organic compound according to claim 1, wherein the boron-containing organic compound has a structure represented by M1 to M101:
9. use of the boron-containing organic compound according to any one of claims 1 to 8 in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer interposed between the first electrode and the second electrode, characterized in that the organic layer contains the boron-containing organic compound according to any one of claims 1 to 8.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2024088326A1 (en) * | 2022-10-28 | 2024-05-02 | 华为技术有限公司 | Organic compound and use thereof |
| WO2024185710A1 (en) * | 2023-03-03 | 2024-09-12 | 出光興産株式会社 | Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024088326A1 (en) * | 2022-10-28 | 2024-05-02 | 华为技术有限公司 | Organic compound and use thereof |
| WO2024185710A1 (en) * | 2023-03-03 | 2024-09-12 | 出光興産株式会社 | Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device |
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