CN115215888A - Boron-containing compound and organic electroluminescent device containing same - Google Patents
Boron-containing compound and organic electroluminescent device containing same Download PDFInfo
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- CN115215888A CN115215888A CN202110410039.0A CN202110410039A CN115215888A CN 115215888 A CN115215888 A CN 115215888A CN 202110410039 A CN202110410039 A CN 202110410039A CN 115215888 A CN115215888 A CN 115215888A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 76
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title abstract description 6
- 229910052796 boron Inorganic materials 0.000 title abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 67
- 239000000463 material Substances 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- 239000010410 layer Substances 0.000 claims description 91
- -1 nitro, hydroxyl Chemical group 0.000 claims description 37
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 25
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 23
- 125000001769 aryl amino group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 239000002346 layers by function Substances 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 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 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 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 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 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 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000011368 organic material Substances 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000010189 synthetic method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000001308 synthesis method Methods 0.000 description 8
- 239000012467 final product Substances 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 238000007725 thermal activation 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 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
- 238000012360 testing method Methods 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- 238000012546 transfer Methods 0.000 description 2
- 125000000008 (C1-C10) alkyl 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
- WIFMYMXKTAVDSQ-UHFFFAOYSA-N 2-bromo-1-benzothiophene Chemical compound C1=CC=C2SC(Br)=CC2=C1 WIFMYMXKTAVDSQ-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
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004873 anchoring 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
- 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
- 125000004618 benzofuryl 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
- 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
- 229910052792 caesium Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 239000003599 detergent Substances 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 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
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 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
- 238000004020 luminiscence type Methods 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
- 239000012046 mixed solvent Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 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
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001044 red dye Substances 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
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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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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- H—ELECTRICITY
- 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
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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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
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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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- 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
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
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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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- 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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Abstract
The invention relates to a boron-containing organic material, which has a structure shown in the following formula (1), belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device. In the formula (1), ring A, ring D and ring E are respectively and independently selected from one of substituted or unsubstituted C5-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings, and at least one of ring A and ring D is a structure shown in a formula (a); the ring A, the ring D, the ring E and Ar 1 And Ar 2 At least one of which is linked to a substituent group of the structure represented by formula (G). Compounds of the invention as OThe luminescent layer material in the LED device shows excellent device performance and stability. The invention also protects the organic electroluminescent device adopting the compound with the general formula.
Description
Technical Field
The invention relates to a boron-containing organic material, belongs to the technical field of organic luminescent materials, and also relates to an application of the compound in an organic electroluminescent device.
Background
The main way people acquire information is through vision, so the display device is of vital importance in the process of human interaction with information. Organic electroluminescent diodes (OLEDs) have many advantages such as flexibility, self-luminescence, high contrast, large size, and low power consumption, and are one of the mainstream display devices at present.
Among them, the red and green dyes as three primary colors generally contain heavy atoms such as Ir, pt, etc., theoretically can achieve 100% internal quantum efficiency, have high electroluminescent efficiency and low power consumption, and become the mainstream of the current commercial display devices. However, the chromaticity and lifetime of blue phosphorescent materials do not meet the current commercial display requirements. Currently, blue devices still use traditional fluorescent materials to achieve high color purity and long device lifetime.
Recently, researchers in Takuji Hatakeyama and Junji Kido et al in Japan reported a series of DABNA-1 (Adv. Mater.2016,28,2777-2781J. Mater.chem.C,2019,7, 3082-3089) organic materials based on TADF (Thermally Activated Delayed Fluorescence) of B-N resonance type, which compounds boron atoms, nitrogen atoms and phenyl groups, constituting a rigid polycyclic aromatic skeleton, and thus have high Fluorescence quantum yield. Compared with the traditional blue fluorescent dye, the compound has narrower spectrum and high color purity. However, the rigid planar structure also causes the difference between the singlet state and the triplet state energy level to be large, the reverse system cross-over from the triplet state to the singlet state is slow, excitons can cause serious efficiency roll-off after being compounded on the dye, and the service life of the device is short. In addition, a rigid structure that is too planar also tends to cause adverse effects such as spectral broadening and red-shift due to too high a doping concentration.
The existing organic electroluminescent materials still have a lot of room for improvement in light emitting performance, and there is a need to develop a new light emitting material system to meet the commercialization demand.
Disclosure of Invention
In order to solve the technical problems, the invention provides a compound with a general formula, which belongs to a thermal activation delayed fluorescent material, aryl alkyl is introduced into the structure of the series of compounds, the molecular distance is increased, the molecular accumulation and the Dexter energy transfer are inhibited, and the efficiency roll-off problem of an organic electroluminescent device adopting the compound is further improved; meanwhile, the heteroaromatic ring is introduced, so that the reverse intersystem crossing rate of the molecules is improved, and in addition, the aryl alkyl has a relatively ideal anchoring effect, so that the molecules can be promoted to be arranged in parallel to the plane of the OLED substrate, and light extraction is facilitated, and the light emitting efficiency is improved.
The invention provides a boron-based organic compound, which has a structure shown as a general formula (1):
in the general formula (1):
in the formula (1), ring A, ring D and ring E are respectively and independently selected from one of substituted or unsubstituted C5-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings, and at least one of ring A and ring D is a structure shown in a formula (a);
in the formula (1), X 1 And X 2 Each is independently selected from one of N, O, S, C and Si; when X is present 1 When selected from N, m is 1, when X is 1 When selected from O or S, m is 0, when X 1 When selected from C or Si, m is 2; when X is 2 When selected from N, N is 1, when X is 2 When selected from O or S, n is 0, when X 2 When selected from C or Si, n is 2;
in the formula (1), ar 1 And Ar 2 Each independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, and Ar 1 May be fused to form a ring system containing X 1 A five-membered ring or a six-membered ring of, and Ar 2 May be fused to an adjacent ring D or to an adjacent ring E to form a ring containing X 2 A five-membered ring or a six-membered ring of (a);
in the formula (a), the ring F is selected from one of substituted or unsubstituted C6-C12 aromatic rings and substituted or unsubstituted C3-C12 heteroaromatic rings;
in the formula (a), X 3 Selected from O or S;
in the formula (G), Z 1 Selected from C or Si; preferably, Z 1 Is C;
in the formula (G), R A 、R B 、R C Each independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, and R A 、R B 、R C At least one of which is one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group, while R A 、R B 、R C At least one of the alkyl groups is one of substituted or unsubstituted C1-C20 chain alkyl groups and substituted or unsubstituted C3-C20 cycloalkyl groups;
when both m and n are not 0, the ring A, the ring D, the ring E and the ring Ar 1 And Ar 2 To which a substituent group of the structure represented by formula (G) is attached;
when m is 0 and n is not 0, the ring A, the ring D, the ring E and Ar 2 To which a substituent group having a structure represented by the formula (G) is bonded;
when the above n is 0 and m is not 0, the ring A, the ring D, the ring E and Ar 1 To which a substituent group of the structure represented by formula (G) is attached;
when n is 0 and m is 0, at least one of the ring A, the ring D and the ring E is connected with a substituent group with a structure shown in a formula (G);
when substituents are present on the above-mentioned ring A, ring D, ring E and ring F, the substituents are selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, and C3-C60 heteroaryl, and the substituents are independently connected to or not connected to the connected aromatic ring or heteroaromatic ring to form a ring;
when the above Ar is 1 、Ar 2 、R A 、R B And R C When a substituent is present, the substituent is selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl and C3-C60 heteroaryl.
In the present invention, the maximum permissible substituents mean the maximum number of substituents as provided for the substituent satisfying the chemical bond requirement.
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, "-" represents the position of the linking site, and "-" represents the expression of the loop structure drawn, and represents the position of the linking site at which any bond can be formed on the loop structure.
In the present specification, the substituted or unsubstituted C6 to C30 aryl group is preferably a C6 to C20 aryl group, more preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, an indenyl group, a fluorenyl group and derivatives thereof, a fluoranthyl group, a triphenylene group, a pyrenyl group, a perylenyl group,
A group of the group consisting of a phenyl group and a tetracenyl group. In particular, 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 and a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9,9 '-dimethylfluorene, 9' -spirobifluorene anda benzofluorene; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl, and 9-tetracenyl.
The hetero atom in the present invention generally means an atom or an atomic group selected from N, O, S, P, si and Se, and is preferably selected from N, O and S. The atomic names given in this disclosure, including their corresponding isotopes, for example, hydrogen (H) includes 1 H (protium or H), 2 H (deuterium or D), etc.; carbon (C) then comprises 12 C、 13 C and the like.
In the present specification, the substituted or unsubstituted C3 to C30 heteroaryl group is preferably a C4 to C20 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, and the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
In the present specification, the C1 to C20 chain alkyl group is preferably a C1 to C10 chain alkyl group, more preferably a C1 to C6 chain alkyl group, and examples thereof include: methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl, and the like.
In the present specification, the C3-C12 cycloalkyl group includes monocycloalkyl and polycycloalkyl groups, preferably C1-C10 alkyl and C3-C10 cycloalkyl groups.
Further, in the formula (1), the ring A, the ring D, the ring E, ar 1 And Ar 2 One of them is linked with a substituent group of the structure represented by the formula (G), or the ring A, the ring D, the ring E, ar 1 And Ar 2 Two of which are linked with substituent groups of the structure shown in formula (G).
Still further, the general formula compound of the present invention has a structure represented by any one of the following formulae (2-1), (2-2), (2-3), (2-4) or (2-5):
in the formula (2-1), the formula (2-2), the formula (2-3), the formula (2-4) and the formula (2-5), the ring A is selected from one of substituted or unsubstituted C5-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings;
the ring F' is selected from one of substituted or unsubstituted C6-C12 aromatic ring and substituted or unsubstituted C3-C12 heteroaromatic ring, and the X is 3 ' is selected from O or S;
the ring E, the ring F and the ring X 1 、X 2 、X 3 、Ar 1 、Ar 2 And m, n are as defined in formula (1);
when both m and n are not 0, the ring A, the ring E, the ring F', ar 1 And Ar 2 Wherein a substituent group having a structure represented by the formula (G) may be bonded;
when m is 0 and n is not 0, the ring A, the ring E, the ring F' and Ar 2 In which a substituent group having a structure represented by the formula (G) may be bonded;
when the above n is 0 and m is not 0, the ring A, the ring E, the ring F' and Ar 1 In which a substituent group having a structure represented by the formula (G) may be bonded;
when the above n is 0 and m is 0, the ring A, the ring E, the ring F' and Ar 1 In which a substituent group having a structure represented by the formula (G) may be bonded;
when the substituents are present on the rings A and F', the substituents are selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl and C3-C60 heteroaryl, and the substituents are independently connected with a connected aromatic ring or heteroaromatic ring to form a ring or not connected with a ring.
In the formula (1), the ring A, the ring D and the ring E are respectively and independently selected from one of substituted or unsubstituted C6-C12 aromatic rings and substituted or unsubstituted C5-C12 heteroaromatic rings, and at least one of the ring A and the ring D is a structure shown in a formula (a);
when the substituent exists on the ring A, the ring D and the ring E, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino and C3-C30 heteroarylamino;
preferably, ring a, ring D, ring E are each independently selected from the following substituted or unsubstituted groups: the aryl group comprises a benzene ring, a furan ring, a thiophene ring, a naphthalene ring, a phenanthrene ring or a carbazole ring, wherein when a substituent group exists, the substituent group is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl and C3-C60 heteroaryl.
In the formula (2-1), the formula (2-2), the formula (2-3), the formula (2-4) or the formula (2-5), the ring A, the ring E, the ring F or the ring F' are respectively and independently selected from one of a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C5-C12 heteroaromatic ring, and the substituent is selected from one of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino and C3-C30 heteroarylamino or the combination of at least two of the groups;
preferably, ring a, ring E, ring F or ring F' are each independently selected from the following substituted or unsubstituted groups: a benzene ring, a furan ring, a thiophene ring, a naphthalene ring, a phenanthrene ring or a carbazole ring, and when a substituent is present, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino and C3-C30 heteroarylamino.
In the formula (1), at least one of the ring A, the ring D, the ring E and the ring F is a group represented by the formula (a):
when ring E is a structure of formula (a), ring D is linked to the other moiety of formula (1) by a shared bond c and a shared bond D, and when ring a, ring D, ring F are each independently a structure of formula (a), ring a, ring D, ring F are each independently linked to the other moiety of formula (1) by a shared bond c or a bond D;
in the formula (a), Z 1 、Z 2 、Z 3 And Z 4 Each independently selected from CR1 or N, wherein R1 is independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and R1 and the connected aromatic ring or the connected heteroaromatic ring can be independently connected with each other through a chemical bond to form a ring;
when Z is 1 、Z 2 、Z 3 And Z 4 When a substituent is present, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino and C3-C30 heteroarylamino.
Further, the general formula compound of the present invention has a structure represented by any one of the following formulas (2-1-1), (2-1-2) or (2-2-1):
said X 1 、X 2 、X 3 、Ar 1 、Ar 2 And the definition of m, nThe same as defined in formula (1);
z is 1’ 、Z 2’ 、Z 3’ 、Z 4’ 、Z 1” 、Z 2” 、Z 3” 、Z 4” 、Z 1”’ 、Z 2”’ 、Z 3”’ And Z 4”’ Are each independently selected from CR 2’ Or N, said R 2’ Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, said R is 2’ The aromatic ring to be linked or the heteroaromatic ring to be linked may each independently be linked to each other via a chemical bond to form a ring;
when a substituent is present, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino and C3-C30 heteroarylamino.
Still further, the compound of the general formula (iii) of the present invention has a structure represented by any one of the following formulae (i), (ii) or (iii):
in the formula (I), formula (II) and formula (III), R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from one or the combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C60 aryl and C3-C60 heteroaryl, and R is 1 、R 2 、R 3 、R 4 、R 5 Each independently being linked to the linking aromatic or heteroaromatic ring to form a ring or not, and R 1 、R 2 、R 3 、R 4 、R 5 At least one of which is a structural group represented by the formula (G);
preferably, said R is 1 、R 2 、R 3 、R 4 、R 5 One of them is a structural group represented by the formula (G), or said R 1 、R 2 、R 3 、R 4 、R 5 Two of them are structural groups represented by formula (G);
further preferably, said R 1 、R 2 、R 4 、R 5 One of them is a structural group represented by the formula (G), or said R 1 、R 2 、R 4 、R 5 Two of them are structural groups represented by formula (G);
still more preferably, said R 2 、R 4 、R 5 One of them is a structural group represented by the formula (G), or said R 2 、R 4 、R 5 Two of them are structural groups represented by formula (G);
more preferably, R is 4 、R 5 One of them is a structural group represented by the formula (G), or said R 4 、R 5 Are all structural groups represented by formula (G);
most preferably, said R 5 Is a structural group represented by the formula (G).
In the compound of the above general formula according to the present invention, the formula (G) has a structure represented by the following formula (G1):
in the formula (G1):
R A 、R B each independently selected from substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroarylAnd R is one of A 、R B At least one of which is a substituted or unsubstituted C1-C10 chain alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group;
R C1 one or two of hydrogen, C1-C10 chain alkyl, C3-C10 naphthenic base, C1-C10 alkoxy, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryl and C3-C30 heteroaryl;
when the above R is A 、R B When a substituent exists, the substituent is one or a combination of at least two of deuterium, halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl and C3-C60 heteroaryl;
preferably, R A And R B At least one of which is selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl or cyclooctyl, R C1 One selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, phenyl, naphthyl, anthryl, thienyl, pyrrolyl, indolyl, carbazolyl or pyridyl.
Still further, the formula (G) is one of the following formula a, formula b, formula c or formula d:
in the formula a, the formula b, the formula c or the formula d, R 6 、R 7 Independently selected from one or the combination of at least two of hydrogen, deuterium, halogen, C1-C10 chain alkyl and C3-C10 naphthenic base;
preferably, the formula (G) is formula a or formula c.
In the compounds of the above general formula, R is 6 、R 7 Each independently selected from hydrogen, or each independently selected fromOne of the following groups:
preferably, R is 6 、R 7 Each independently selected from hydrogen.
In the above compounds of the general formula of the invention, R is 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, or each independently selected from one of the following groups:
preferred structures of the compounds of the present invention include the following specific compounds P1 to P152, but are not limited to these compounds:
as another aspect of the present invention, there is also provided a use of the compound as described above in an organic electroluminescent device. In particular, the use as a material for a light emitting layer in an organic electroluminescent device is preferred, more preferably as a material in a light emitting layer in an organic electroluminescent device, and in particular as a light emitting dye may be applied.
As still another aspect of the present invention, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer contains a compound of formula (1), formula (2-2), formula (2-3), formula (2-4), formula (2-5) as described above, or a compound having a structure represented by P1 to P152 as described above.
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and a first electrode, a plurality of light-emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains the compound of the formula (1), the formula (2-2), the formula (2-3), the formula (2-4) and the formula (2-5) or the compound of the structure shown by the P1-P157.
The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device; preferably, the display screen or the display panel is an OLED display.
The invention also discloses electronic equipment, wherein the electronic equipment is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
The specific reason why the above-mentioned compound of the present invention is excellent as a material for a light-emitting dye and/or a sensitizer in a light-emitting layer in an organic electroluminescent device is not clearly understood, and it is presumed that the following reasons are possible:
1. the boron atom contained in the compound has resonance effect with the nitrogen atom in the same ring, so that the series of materials have the characteristics of narrow spectrum and thermal activation delayed fluorescence emission.
2. A series of materials contain aryl-substituted quaternary carbon and the like, so that the transmission capability can be ensured, the molecular distance can be further increased, quenching caused by accumulation can be inhibited, the efficiency roll-off can be further reduced, and the service life of a device can be prolonged.
3. The introduction of the heteroatom can improve the reverse intersystem crossing rate of the molecule, thereby further improving the efficiency and the service life of the device.
In addition, 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.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
It should be noted that the method and materials for obtaining the compound are not limited to the method and materials used in the present invention, and those skilled in the art may select other methods or routes to obtain the compound provided in the present invention. The compounds of the synthetic methods not mentioned in the present invention are all starting products obtained commercially or are self-made by these starting products according to known methods.
The solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, tert-butyl-ben, boron tribromide, carbazole, diphenylamine and other chemical reagents, can be purchased from domestic chemical product markets, such as reagents from national drug group, TCI, shanghai Bide medical company, bailingwei reagent company, and the like.
The synthesis of the compounds of the present invention is briefly described below.
Synthetic examples
Representative synthesis route:
with or without aromatic rings 1,2 attached
Synthesis of intermediate A1:
2-bromobenzothiophene (20g, 93.86mmol), 4-tert-butylaniline (18.21g, 122.01mmol), sodium tert-butoxide (12.63g, 131.40mmol), pd2 (dba) 3 (4.3g, 4.69mmol) and S-Phos (6.71g, 14.08mmol) are added into a 500ml three-neck flask, 200ml of toluene is added, heating reflux reaction is carried out for 2 hours, then sampling is carried out for HPLC test, the raw materials are completely reacted, reaction is stopped, filtering is carried out, filtrate is concentrated to be dry under reduced pressure, and ethyl acetate + n-hexane is used for crystallization twice, so that 23.5g of the target product is obtained.
Synthesis of intermediate A2:
the target intermediate A2 is finally obtained by using the same synthetic method as A1.
Synthesis of intermediate A3:
the target intermediate A3 is finally obtained using the same synthetic method as A1.
Synthesis of intermediate A4:
the target intermediate A4 is finally obtained using the same synthetic method as A1.
Synthesis of intermediate A5:
the target intermediate A5 was finally obtained using the same synthesis method as A1.
Synthesis of intermediate A6:
the target intermediate A6 was finally obtained using the same synthesis method as A1.
Synthesis of intermediate B1:
4- (phenyl) tert-butylbromobenzene (20g, 72.68mmol), m-tert-butylbenzamine (11.93g, 79.95mmol), sodium tert-butoxide (10.48g, 109.02mmol), S-Phos (5.2g, 10.90mmol), pd 2 (dba) 3 (3.33g, 3.63mmol) is added into a 500ml three-neck flask, 200ml toluene is added, heating and refluxing are carried out for 3h under the protection of nitrogen, sampling is carried out by TLC detection, the raw materials are reacted completely, filtering is carried out, and reduced pressure distillation purification is carried out, thus obtaining 20.7g of the target product.
Synthesis of intermediate C1:
2-bromo-6-chloro-4- (phenyl) isopropylchlorobenzene (10g, 29.06mmol), m-tert-butyldiphenylamine (9.82g, 34.88mmol), sodium tert-butoxide (4.20g, 43.60mmol), S-Phos (2.1g, 4.36mmol), pd 2 (dba) 3 (1.33g, 1.45mmol) was added into a 500ml three-necked flask, 200ml of toluene was added, heating and refluxing were carried out for 3 hours under nitrogen protection, sampling was carried out by TLC detection, the reaction of the raw materials was completed, filtration was carried out, distillation under reduced pressure was carried out until dryness, and recrystallization was carried out twice using toluene + ethanol to obtain 13.65g of the objective intermediate.
Synthesis of intermediate C2:
the target intermediate C2 is finally obtained by using the same synthesis method as C1.
Synthesis of intermediate C3:
the target intermediate C3 is finally obtained using the same synthetic method as C1.
Synthesis of intermediate C4:
the target intermediate C4 is finally obtained using the same synthetic method as C1.
Synthesis of intermediate D1:
the intermediate C3 (10g, 21.72mmol), A1 (7.33g, 26.06mmol), sodium tert-butoxide (3.13, 32.58 mmol) and Pd132 (0.769g, 1.09mmol) are added into a 500ml three-neck flask, 200ml of toluene is added into the three-neck flask, the mixture is heated and refluxed for 3 hours under the protection of nitrogen, samples are taken for TLC detection, the raw materials are completely reacted, filtered, distilled under reduced pressure to be dry, and recrystallized twice by using toluene and ethanol, so that 11.25g of the target intermediate is obtained.
Synthesis of intermediate D2:
and finally obtaining a target intermediate D2 by using the same synthetic method as D1.
Synthesis of intermediate D3:
the target intermediate D3 is finally obtained by using the same synthetic method as D1.
Synthesis of intermediate D4:
and finally obtaining a target intermediate D4 by using the same synthetic method as D1.
Synthesis of intermediate D5:
the same synthetic method as that of D1 is used, and the target intermediate D5 is finally obtained.
Synthesis of intermediate D6:
the same synthetic method as that of D1 is used, and the target intermediate D6 is finally obtained.
Synthesis of intermediate D7:
the same synthesis method as that of D1 is used, and the target intermediate D7 is finally obtained.
Synthesis of intermediate D8:
the same synthesis method as that of D1 is used, and the target intermediate D8 is finally obtained.
The synthesis general formula is as follows:
synthesis of the final product P76:
adding the intermediate D1 into a 500ml three-neck flask, adding 200ml of tert-butyl benzene, slowly adding n-butyllithium (11ml, 2.5M) under the protection of nitrogen at-20 ℃, activating at 60 ℃ for 2h, sequentially adding boron tribromide (10.65g, 42.53mmol), DIEA (7.33g, 56.71mmol) under-20 ℃, reacting at 110 ℃ overnight, sampling the next day for TLC detection, completely reacting the raw materials, filtering, evaporating to dryness under reduced pressure, and purifying by column chromatography to obtain 2.34g of a target product.
Synthesis of final product P82:
the same synthesis method as that of P76 is used, and the target product P82 is finally obtained.
Synthesis of final product P90:
the same synthesis method as that of P76 is used, and the target product P90 is finally obtained.
Synthesis of final product P35:
the same synthesis method as P76 is used, and the target product P35 is finally obtained.
Synthesis of final product P131:
the target product P131 is finally obtained by using the same synthetic method as P76.
Synthesis of the end product P130:
the target product P130 is finally obtained by using the same synthetic method as P76.
Synthesis of final product P133:
the target product P133 is finally obtained by using the same synthetic method as P76.
The synthesis general formula is as follows:
synthesis of final product P118:
the same synthetic method as P76 is used, and the target product P118 is finally obtained.
Application example of the Compound of the present invention to the preparation of an organic electroluminescent device
Detailed description of the preferred embodiments
The OLED 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 under the first electrode or over 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 serves as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), 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 multi-layer 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 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 use one or more compounds of HT-1 to HT-51 described above, or use one or more compounds of HI-1-HI-3 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 HI-1-HI-3 described below.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (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 single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked 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 emitting red, green, blue, or the like at the same time.
According to different technologies, the material of the light-emitting layer can be different materials such as a fluorescent electroluminescent material, a phosphorescent electroluminescent material, a 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 a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
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 fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, the combination of one or more of BFD-1 through BFD-24 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light-emitting layer is selected from, but not limited to, one or more 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 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 combinations 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, combinations of one or more of ET-1 through ET-73 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer can adopt, but is not limited to, one or more compounds from ET-1 to ET-73 or one or more compounds from PH-1 to PH-46; mixtures of one or more compounds from ET-1 to ET-73 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,Li 2 O,Cs 2 CO 3 ,BaO,Na,Li,Ca，Mg，Yb。
The preparation process of the organic electroluminescent device in the embodiment is 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: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding the surface with low-energy cationic beam;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to<1×10 -5 Pa, vacuum thermal evaporation of a 10nm mixture of HT-4. 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.
Devices of examples 2 to 19 were fabricated in the same manner as in device example 1 except that P76 in the light-emitting layer was replaced with P82, P90, P35, P131, P130, P133, P66, P98, P104, P32, P34, P121, P122, 136, P126, P137, P138, and P157, respectively.
Device comparative examples 1 and 2 were fabricated in the same manner as in device example 1 except that P76 in the light-emitting layer was replaced with C1 and C2, respectively (CN 111253421A).
The organic electroluminescent device prepared by the above process was subjected to the following property measurements:
the driving voltage, current efficiency and lifetime of the organic electroluminescent devices prepared in examples 1 to 19 and comparative examples 1 to 2 were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the luminance of the organic electroluminescent device was measured to reach 1000cd/m by raising the voltage at a rate of 0.1V per second 2 The current density is measured at the same time as the driving voltage; measurement of 1 by integrating sphere000cd/m 2 External quantum efficiency of time;
life test of LT95 is as follows: using a luminance meter at 1000cd/m 2 The luminance drop of the organic electroluminescent device was measured to 950cd/m by maintaining a constant current at luminance 2 Time in hours.
In table 1, the measured data life of comparative example 1 is set as reference data, and other data are normalized numerical values;
specific performance data are detailed in table 1 below.
TABLE 1
As can be seen from Table 1 above, when the compound of the present invention is used as a dye, the luminous efficiency is relatively high and the lifetime is longer than when the compound C1 of the prior art is used as a comparative example. The reason is that the reverse intersystem crossing rate of molecules is improved after the heteroatom is introduced, and the concentration of triplet excitons in the light-emitting layer is reduced, so that the quenching of the excitons is inhibited, and the efficiency and the stability of the device are improved;
compared with the compound C2 in the prior art, when the compound is used as a dye, the voltage is lower, and the luminous efficiency and the service life are higher, which is probably because the introduction of the aryl substituted alkyl improves the carrier transmission rate, and simultaneously effectively inhibits the accumulation of molecules and the energy transfer of Dexter, so that the efficiency and the stability of a device are improved. The above advantages are advantageous for practical application of the compounds of the present invention.
Although the present invention has been described in connection with the embodiments, the present invention is not limited to the above-described embodiments, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the present invention, and the scope of the present invention is outlined by the appended claims.
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 derived therefrom are intended to be within the scope of the invention.
Claims (15)
1. A compound of the general formula (I) having a structure represented by the following formula (1):
in the formula (1), ring A, ring D and ring E are respectively and independently selected from one of substituted or unsubstituted C5-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings, and at least one of ring A and ring D is a structure shown in a formula (a);
in the formula (1), X 1 And X 2 Each is independently selected from one of N, O, S, C and Si; when X is present 1 When selected from N, m is 1, when X is 1 When selected from O or S, m is 0, when X is 1 When selected from C or Si, m is 2; when X is 2 When selected from N, N is 1, when X is 2 When selected from O or S, n is 0, when X 2 When selected from C or Si, n is 2;
in the formula (1), ar 1 And Ar 2 Each independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, and Ar 1 May be fused to an adjacent ring A or to an adjacent ring E to form a ring containing X 1 A five-membered ring or a six-membered ring of, and Ar 2 May be fused to an adjacent ring D or to an adjacent ring E to form a ring containing X 2 A five-membered ring or a six-membered ring of (a);
in the formula (a), the ring F is selected from one of substituted or unsubstituted C6-C12 aromatic rings and substituted or unsubstituted C3-C12 heteroaromatic rings;
in the formula (a), X 3 Selected from O or S;
in the formula (G), Z 1 Selected from C or Si; preferably, Z 1 Is C;
in the formula (G), R A 、R B 、R C Each independently selected from one of substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, and R A 、R B 、R C At least one of which is one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group, while R A 、R B 、R C At least one of them is one of substituted or unsubstituted C1-C20 chain alkyl and substituted or unsubstituted C3-C20 cycloalkyl;
when both m and n are not 0, the ring A, the ring D, the ring E and the ring Ar 1 And Ar 2 To which a substituent group having a structure represented by the formula (G) is bonded;
when m is 0 and n is not 0, the ring A, the ring D, the ring E and Ar 2 To which a substituent group having a structure represented by the formula (G) is bonded;
when the above n is 0 and m is not 0, the ring A, the ring D, the ring E and Ar 1 To which a substituent group of the structure represented by formula (G) is attached;
when n is 0 and m is 0, at least one of the ring a, the ring D, and the ring E is connected with a substituent group having a structure represented by formula (G);
when a substituent is present on the above-mentioned ring A, ring D, ring E and ring F, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl, and the substituent is independently connected with a connected aromatic ring or heteroaromatic ring to form a ring or not connected with a ring to form a ring;
when the above Ar is 1 、Ar 2 、R A 、R B And R C When a substituent is present, the substituent is selected from one or a combination of at least two of halogen, cyano, nitro, hydroxyl, amino, C1-C20 silyl, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl and C3-C60 heteroaryl.
2. The compound of the general formula (1), wherein the ring A, the ring D, the ring E, and the Ar 1 And Ar 2 One of them is linked with a substituent group of the structure represented by the formula (G), or the ring A, the ring D, the ring E, ar 1 And Ar 2 Two of which are linked with substituent groups of the structure shown in formula (G).
3. The general formula compound according to claim 1, having a structure represented by any one of the following formulae (2-1), (2-2), (2-3), (2-4) or (2-5):
in the formula (2-1), the formula (2-2), the formula (2-3), the formula (2-4) and the formula (2-5), the ring A is selected from one of substituted or unsubstituted C5-C60 aromatic rings and substituted or unsubstituted C3-C60 heteroaromatic rings;
the ring F' is selected from one of substituted or unsubstituted C6-C12 aromatic ring and substituted or unsubstituted C3-C12 heteroaromatic ring, and the X is 3 ' is selected from O or S;
the ring E, the ring F and the ring X 1 、X 2 、X 3 、Ar 1 、Ar 2 And m, n are as defined in formula (1);
when both m and n are not 0, the ring A, the ring E, the ring F', ar 1 And Ar 2 Wherein a substituent group having a structure represented by the formula (G) may be bonded;
when m is 0 and n is not 0, the ring A, the ring E, the ring F' and Ar 2 Wherein a substituent group having a structure represented by the formula (G) may be bonded;
when the above n is 0 and m is not 0, the ring A, the ring E, the ring F' and Ar 1 In which a substituent group having a structure represented by the formula (G) may be bonded;
when the above n is 0 and m is 0, the ring A, the ring E, the ring F' and Ar 1 In which a substituent group having a structure represented by the formula (G) may be bonded;
when the substituents are present on the rings A and F', the substituents are selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl and C3-C60 heteroaryl, and the substituents are independently connected with the connected aromatic ring or heteroaromatic ring to form a ring or not connected with a ring.
4. The compound of the general formula (la) according to claim 1, wherein ring a, ring D and ring E are each independently selected from one of substituted or unsubstituted C6-C12 aromatic rings and substituted or unsubstituted C5-C12 heteroaromatic rings, and at least one of ring a and ring D has a structure represented by formula (a);
when a substituent exists on the ring A, the ring D and the ring E, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino and C3-C30 heteroarylamino;
preferably, ring a, ring D, ring E are each independently selected from the group consisting of substituted or unsubstituted: the aryl group comprises one of a benzene ring, a furan ring, a thiophene ring, a naphthalene ring, a phenanthrene ring or a carbazole ring, and when a substituent group exists, the substituent group is selected from one of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl and C3-C60 heteroaryl or the combination of at least two of the halogen, the C1-C20 chain alkyl, the C3-C20 cycloalkyl, the C1-C20 alkoxy, the C6-C60 aryl and the C3-C60 heteroaryl.
5. The compound of the general formula of claim 3, wherein the ring A, the ring E, the ring F or the ring F' are respectively and independently selected from one of a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C5-C12 heteroaromatic ring, and the substituent is selected from one of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino and C3-C30 heteroarylamino or a combination of at least two of the same;
preferably, ring a, ring E, ring F or ring F' are each independently selected from the group consisting of substituted or unsubstituted: when a substituent is present, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino and C3-C30 heteroarylamino.
6. The compound of formula (la) according to claim 1, wherein at least one of ring a, ring D, ring E, ring F is a group of formula (a):
when ring E is a structure of formula (a), ring D is linked to the other moiety of formula (1) by shared bond c and shared bond D, and when ring a, ring D, ring F are each independently a structure of formula (a), ring a, ring D, ring F are each independently linked to the other moiety of formula (1) by shared bond c or bond D;
in the formula (a), Z 1 、Z 2 、Z 3 And Z 4 Are each independently selected from CR 1 Or N, said R 1 Independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chainOne of a linear alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C1-C20 silyl group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C6-C60 heteroarylamino group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C3-C60 heteroaryl group, wherein R is R 1 The linked aromatic rings or the linked heteroaromatic rings may each independently be linked to each other by a chemical bond to form a ring;
when Z is 1 、Z 2 、Z 3 And Z 4 When a substituent is present, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino and C3-C30 heteroarylamino.
7. The general formula compound according to claim 6, having a structure represented by any one of the following formula (2-1-1), formula (2-1-2), formula (2-2-1), or formula (2-2-2):
said X 1 、X 2 、X 3 、Ar 1 、Ar 2 And m, n are as defined in formula (1);
z is 1’ 、Z 2’ 、Z 3’ 、Z 4’ 、Z 1” 、Z 2” 、Z 3” 、Z 4” 、Z 1”’ 、Z 2”’ 、Z 3”’ And Z 4”’ Are each independently selected from CR 2’ Or N, said R 2’ Independently selected from hydrogen, halogen, cyano, nitro, hydroxy, amino, substituted orOne of unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, wherein R is R 2’ The aromatic ring to be linked or the heteroaromatic ring to be linked may each independently be linked to each other via a chemical bond to form a ring;
when a substituent is present, the substituent is selected from one or a combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C60 aryl, C3-C60 heteroaryl, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 arylamino and C3-C30 heteroarylamino.
8. A compound of formula (la) according to claim 1, having a structure according to any one of the following formulae (i), (ii), (iii) or (lb):
in the formula (I), the formula (II), the formula (III) and the formula (IV), R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from one or the combination of at least two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C1-C20 silyl, cyano, nitro, hydroxyl, amino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C60 aryl and C3-C60 heteroaryl, and R is 1 、R 2 、R 3 、R 4 、R 5 Are each independently linked to a linking aromatic or heteroaromatic ring to form a ring or not, and R 1 、R 2 、R 3 、R 4 、R 5 At least one of which is a structural group represented by the formula (G);
preferably, said R is 1 、R 2 、R 3 、R 4 、R 5 One of them is a structural group represented by the formula (G), or said R 1 、R 2 、R 3 、R 4 、R 5 Two of them are structural groups represented by formula (G);
further preferably, R is 1 、R 2 、R 4 、R 5 One of them is a structural group represented by the formula (G), or said R 1 、R 2 、R 4 、R 5 Two of them are structural groups represented by formula (G);
still more preferably, said R 2 、R 4 、R 5 One of them is a structural group represented by the formula (G), or said R 2 、R 4 、R 5 Two of them are structural groups represented by formula (G);
more preferably, R is 4 、R 5 One of them is a structural group represented by the formula (G), or said R 4 、R 5 All structural groups represented by formula (G);
most preferably, said R 5 Is a structural group represented by the formula (G).
9. A compound of general formula according to any one of claims 1 to 8, wherein the formula (G) has the structure shown in formula (G1) below:
in the formula (G1):
R A 、R B each independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, and R A 、R B At least one of which is a substituted or unsubstituted C1-C10 chain alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group;
R C1 selected from hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamineOne or two of C3-C30 heteroaryl amino, C6-C30 aryl and C3-C30 heteroaryl;
when the above R is A 、R B When a substituent exists, the substituent is selected from one or a combination of at least two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 aryl and C3-C60 heteroaryl;
preferably, R A And R B At least one of which is selected from one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl or cyclooctyl, R C1 One selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, phenyl, naphthyl, anthryl, thienyl, pyrrolyl, indolyl, carbazolyl or pyridyl.
10. A compound of formula (la) according to claim 9, wherein the formula (G) is one of formula a, formula b, formula c or formula d:
in the formula a, the formula b, the formula c or the formula d, R 6 、R 7 Independently selected from one or the combination of at least two of hydrogen, deuterium, halogen, C1-C10 chain alkyl and C3-C10 naphthenic base;
preferably, the formula (G) is formula a or formula c.
11. A compound of formula (la) according to claim 10, wherein R 6 、R 7 Each independently selected from hydrogen, or each independently selected from one of the following groups:
preferably, R is 6 、R 7 Each independently selected from hydrogen.
12. A compound of formula (la) according to any one of claims 8, 10 or 11, wherein R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from hydrogen, or each independently selected from one of the following groups:
13. a compound of formula (la) according to claim 1, selected from the compounds of the following specific structures:
14. use of a compound as claimed in any one of claims 1 to 13 as a light-emitting layer material in an organic electroluminescent device.
15. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound according to any one of claims 1 to 13;
preferably, the organic functional layer comprises a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light emitting layer is disposed between the hole transport layer and the electron transport layer, wherein the light emitting layer contains the compound according to any one of claims 1 to 13.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024090353A1 (en) * | 2022-10-27 | 2024-05-02 | 東レ株式会社 | Compound, luminescent element material, luminescent element, display device, and illuminator |
| WO2024120527A1 (en) * | 2022-12-08 | 2024-06-13 | 浙江光昊光电科技有限公司 | Boron-nitrogen-containing organic compound and use thereof in organic electronic device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024090353A1 (en) * | 2022-10-27 | 2024-05-02 | 東レ株式会社 | Compound, luminescent element material, luminescent element, display device, and illuminator |
| WO2024120527A1 (en) * | 2022-12-08 | 2024-06-13 | 浙江光昊光电科技有限公司 | Boron-nitrogen-containing organic compound and use thereof in organic electronic device |
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