CN117402130A - 1,3, 4-triaryl substituted dibenzofuran compound and light-emitting device thereof - Google Patents
1,3, 4-triaryl substituted dibenzofuran compound and light-emitting device thereof Download PDFInfo
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- CN117402130A CN117402130A CN202311352310.5A CN202311352310A CN117402130A CN 117402130 A CN117402130 A CN 117402130A CN 202311352310 A CN202311352310 A CN 202311352310A CN 117402130 A CN117402130 A CN 117402130A
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- deuterium atom
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- -1 dibenzofuran compound Chemical class 0.000 title claims abstract description 31
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 title abstract description 20
- 239000010410 layer Substances 0.000 claims abstract description 175
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 239000000463 material Substances 0.000 claims abstract description 71
- 125000004431 deuterium atom Chemical group 0.000 claims description 44
- 229910052805 deuterium Inorganic materials 0.000 claims description 36
- 230000000903 blocking effect Effects 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 230000005525 hole transport Effects 0.000 claims description 17
- 239000012044 organic layer Substances 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000002356 single layer Substances 0.000 abstract description 11
- 230000005540 biological transmission Effects 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- 150000004826 dibenzofurans Chemical class 0.000 description 22
- 239000010408 film Substances 0.000 description 21
- 238000002156 mixing Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 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 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 150000003220 pyrenes Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- KWZAIOOHESKUSV-UHFFFAOYSA-N (10-phenylanthracen-9-yl)oxyboronic acid Chemical compound C12=CC=CC=C2C(OB(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 KWZAIOOHESKUSV-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- BBYJEAKHNVUYMN-UHFFFAOYSA-N 1-phenyl-2h-1,3,5-triazine Chemical compound C1N=CN=CN1C1=CC=CC=C1 BBYJEAKHNVUYMN-UHFFFAOYSA-N 0.000 description 1
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 description 1
- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C(=CC=CC=1)C1(CCCCC1)C=1C(=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- QJZJIWYDCCBNTH-UHFFFAOYSA-N 9-[4-(9H-fluoren-1-yl)phenyl]carbazole Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C1=2)C1=CC=C(C=C1)C1=CC=CC=2C3=CC=CC=C3CC1=2 QJZJIWYDCCBNTH-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FUHDUDFIRJUPIV-UHFFFAOYSA-N [4-[9-(4-carbazol-9-ylphenyl)fluoren-9-yl]phenyl]-triphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C1(C2=CC=CC=C2C2=CC=CC=C21)C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)(C=1C=CC=CC=1)C1=CC=CC=C1 FUHDUDFIRJUPIV-UHFFFAOYSA-N 0.000 description 1
- JZXXUZWBECTQIC-UHFFFAOYSA-N [Li].C1=CC=CC2=NC(O)=CC=C21 Chemical compound [Li].C1=CC=CC2=NC(O)=CC=C21 JZXXUZWBECTQIC-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- KQDCFCNAAUGBMS-UHFFFAOYSA-N [Sb].BrC1=C(N(Br)Br)C=CC=C1 Chemical compound [Sb].BrC1=C(N(Br)Br)C=CC=C1 KQDCFCNAAUGBMS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-N aluminum;2-methylquinolin-8-ol;4-phenylphenol Chemical compound [Al+3].C1=CC=C(O)C2=NC(C)=CC=C21.C1=CC=C(O)C2=NC(C)=CC=C21.C1=CC(O)=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-N 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000006872 improvement Effects 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
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical class C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- XEXYATIPBLUGSF-UHFFFAOYSA-N phenanthro[9,10-b]pyridine-2,3,4,5,6,7-hexacarbonitrile Chemical compound N1=C(C#N)C(C#N)=C(C#N)C2=C(C(C#N)=C(C(C#N)=C3)C#N)C3=C(C=CC=C3)C3=C21 XEXYATIPBLUGSF-UHFFFAOYSA-N 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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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
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to the technical field of organic photoelectric materials, and relates to a 1,3, 4-triaryl substituted dibenzofuran compound and a light-emitting device thereof. Specifically, the compound of the present invention is represented by the following general formula I, has excellent film forming property and thermal stability, and can be used as a main material of a light emitting layer to prepare an organic electroluminescent device, particularly a blue organic electroluminescent device. More importantly, the compound has excellent transmission performance and luminous performance, and when the compound is used as a blue light luminous layer material, the voltage of a single-layer electroluminescent device and a laminated electroluminescent device is effectively reduced, and the luminous efficiency and the service life performance are improved.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and relates to 1,3, 4-triaryl substituted dibenzofuran compounds and a light-emitting device containing the compounds. More particularly, the present invention relates to 1,3, 4-triaryl-substituted dibenzofuran-based compounds suitable for use in organic electroluminescent devices (particularly blue-light organic electroluminescent devices) and light-emitting devices using such compounds.
Background
The organic electroluminescent device (organic electroluminescent device) has a series of advantages of self-luminescence, low-voltage driving, full curing, wide viewing angle, simple composition and process, and the like, and does not require a backlight source compared with a liquid crystal display. Therefore, the organic electroluminescent device has wide application prospect.
The organic electroluminescent device generally includes an anode, a metal cathode, and an organic layer sandwiched therebetween. The organic layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. In addition, the light-emitting layer mostly adopts a host-guest structure, i.e., the light-emitting material (guest material) is doped in other materials (host materials) with a certain concentration, so as to avoid concentration quenching caused by the too high concentration of the doped material and annihilation of triplet states of the doped material in the phosphorescent device system, and improve the light-emitting efficiency. Phosphorescent and Thermally Activated Delayed Fluorescence (TADF) blue OLED materials based on triplet emission mechanisms have higher device efficiency, but the lifetime performance still cannot meet the application requirements, so that a fluorescent device-based system is still adopted in the blue OLED at present.
In the existing blue fluorescent device system, the blue light main material generally adopts an aromatic heterocyclic compound with a specific condensed ring shape, mainly uses dibenzofuranyl and anthracenyl as frameworks, and the anthracenyl can utilize annihilation effect (TTA) of electrons in a triplet state to improve the total amount of singlet excitons; specifically, two triplet excitons annihilate each other to generate a ground state electron and a singlet exciton, and then the generated singlet exciton transitions back to the ground state and emits fluorescence, so that the internal quantum efficiency of the fluorescent material is greatly improved, and the theoretical limit of the internal quantum efficiency can reach 62.5%.
In recent years, blue light main materials with dibenzofuranyl and anthracenyl as frameworks are continuously improved, and although certain progress is made in aspects of reducing working voltage, improving device efficiency, prolonging working life and the like, along with product upgrading, continuous demands still exist for long-life, low-voltage and high-efficiency blue light OLED luminescent materials and device development. Around the blue light host material with dibenzofuranyl and anthracenyl as the skeleton, some patent applications have disclosed related technical content. Wherein, JP2005314239A discloses anthryl monosubstituted dibenzofuran compounds 7 and anthryl and phenyl disubstituted dibenzofuran compounds 17, but the voltage of the compounds is generally higher (more than 5.3V) when the compounds are used as blue light main materials in devices, and the service life performance is still to be improved; CN109804043A, CN109790462A, CN111933810A, CN106356468A, CN107531661A, CN113582955A and KR1020220081059a, etc. each disclose a series of triaryl-substituted dibenzofurans (aryl substitution sites are identical to each other) and achieve a significant improvement in device voltage, but unfortunately none of these patent applications relates to the relationship between different aryl substitution sites and device performance, but triaryl-substituted dibenzofurans based on different substitution sites differ greatly in device performance (especially in voltage, efficiency and lifetime), and thus a related study is necessary. In addition, all three aryl groups in the dibenzofuran compound are not substituted on the same benzene ring, so that the corresponding technical blank still exists in the field.
Disclosure of Invention
Problems to be solved by the invention
Aiming at the problems existing in the prior art, the invention provides a series of 1,3, 4-triaryl substituted dibenzofuran compounds with novel structures and a luminescent device thereof. The compound provided by the invention has high thermal stability and high chemical stability by virtue of the self-rigid framework structure, is finally applied to a light-emitting device, and prolongs the service life of the device. And the substituents at three different sites further improve the stability and luminous efficiency of the device and reduce the driving voltage of the device by utilizing mutual steric hindrance.
Solution for solving the problem
For the prior triaryl substituted dibenzofuran compounds, three substitution sites are not on the same benzene ring, and the invention takes the 1 position, the 3 position and the 4 position in the dibenzofuran structure as connection sites to respectively introduce aryl groups such as anthryl and the like. The 1,3, 4-trisubstituted mode utilizes large steric hindrance between adjacent positions, realizes the highly-stereospecific molecular conformation of the triaryl substituted dibenzofuran compound, maximally utilizes the steric hindrance effect and maintains the electronic and photophysical characteristics of the dibenzofuran structure. The connection mode is particularly suitable for constructing a blue light main body material, can obtain main body molecules with steric hindrance structures, can prevent aggregation effect while improving molecular arrangement, ensures carrier mobility and avoids quantum efficiency reduction caused by aggregation. In addition, the 1,3, 4-trisubstituted mode of three substituent groups on one benzene ring can form a relatively concentrated pi-electron conjugated system, which is favorable for electron transmission, realizes voltage reduction and finally achieves the purpose of improving the light-emitting device.
That is, the embodiments of the present invention are as described in the foregoing embodiments.
ADVANTAGEOUS EFFECTS OF INVENTION
The 1,3, 4-triaryl substituted dibenzofuran compound has a highly-three-dimensional rigid structure and good film forming property and thermal stability. The dibenzofuran compounds are very suitable for preparing various light-emitting devices, in particular blue-light organic electroluminescent devices due to the fact that no additional steric hindrance groups are introduced. The luminescent device prepared from the dibenzofuran compound has the advantages of low driving voltage, high luminous efficiency and long service life. The specific effects are as follows:
the 1,3, 4-triaryl substituted dibenzofuran compounds have adjustable carrier transmission performance, adjustable HOMO energy levels and proper singlet and triplet energy levels, and are suitable for being used as a constituent material of a light-emitting layer in an organic electroluminescent device, in particular as a main body material. The luminescent device prepared by the material, especially the blue light organic electroluminescent device, has the advantages of low driving voltage, high luminous efficiency and long service life, and is obviously superior to the existing organic electroluminescent device.
In addition, the preparation method of the 1,3, 4-triaryl substituted dibenzofuran compound is simple, raw materials are easy to obtain, and the development requirement of industrial large-scale production can be met.
Drawings
FIG. 1 is a diagram of compound I-1 of example 1 of the present invention 1 H-NMR spectrum.
FIG. 2 is a diagram of compound I-5 in example 3 of the present invention 1 H-NMR spectrum.
FIG. 3 is a diagram of compound I-4 of example 2 of the present invention 1 H-NMR spectrum.
Fig. 4 is an organic electroluminescence spectrum of the organic EL devices 2,8, 12, and 23 in example 29, example 35, example 39, and example 50 of the present invention.
Fig. 5 is a graph of device luminance versus lumen efficiency for organic EL device 44 in example 71 of the present invention.
Fig. 6 is a device brightness-Blue index (Blue index) curve of the organic EL device 44 in example 71 of the present invention.
Fig. 7 is a schematic view showing the constitution of the organic EL devices of examples 1 to 27 and comparative examples 1 to 7 of the present invention, in which layer 7 (i.e., hole blocking layer) was not included in the actual layered structure of the device.
Description of the reference numerals
1, a substrate; 2, anode; 3a hole injection layer; 4 a hole transport layer; 5 an electron blocking layer; 6 a light emitting layer; 7, a hole blocking layer; 8 an electron transport layer; 9 an electron injection layer; 10 cathode
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments.
<1,3, 4-Triaryl-substituted dibenzofurans >
The 1,3, 4-triaryl substituted dibenzofuran compounds of the invention can be represented by the following general formula I,
wherein,
Ar 1 、Ar 2 and Ar is a group 3 Each independently represents any one of the following groups optionally substituted with one or more deuterium atoms: phenyl, naphthyl, biphenyl, and phenyl-substituted naphthyl;
each R is 1 Each independently represents a hydrogen atom or a deuterium atom.
Preferably, in formula I, ar 1 、Ar 2 And Ar is a group 3 Each independently represents any one of the following groups:
wherein,
the dashed line represents a bond;
each R is 2 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom. More preferably, in formula I, ar 1 Represents any one of the following groups:
and Ar is 2 And Ar is a group 3 Each independently represents any one of the following groups:
wherein,
the dashed line represents a bond;
each R is 2 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom.
Preferably, the 1,3, 4-triaryl-substituted dibenzofurans of the present invention may be represented by the following formula I',
wherein,
each R is 1 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
Ar 1 、Ar 2 and Ar is a group 3 As defined in formula I.
In one embodiment, the 1,3, 4-triaryl-substituted dibenzofurans of the present invention may be represented by the following formula I-1, preferably by the following formula I' -1,
wherein,
each R is 1 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
each R is 2 Each independently represents a hydrogen atom, a deuterium atom, a phenyl group or a phenyl group substituted by one or more deuterium atoms, and five R's attached to the same benzene ring 2 At most one of which is phenyl or phenyl substituted with one or more deuterium atoms; preferably, each R 2 Each independently represents a deuterium atom or a pentadeuterated phenyl group, and five R's attached to the same benzene ring 2 At most one of which is pentadeuterated phenyl;
Ar 1 as defined in formula I.
In one embodiment, the 1,3, 4-triaryl-substituted dibenzofurans of the present invention may be represented by the following formula I-2, preferably by the following formula I' -2,
wherein,
each R is 1 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
each R is 2 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
Ar 1 as defined in formula I.
In one embodiment, the 1,3, 4-triaryl-substituted dibenzofurans of the present invention may be represented by the following formula I-3, preferably by the following formula I' -3,
wherein,
each R is 1 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
each R is 2 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
Ar 1 as defined in formula I.
Specifically, the 1,3, 4-triaryl substituted dibenzofuran compounds of the present invention may be selected from any one of the following compounds:
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< organic electroluminescent device >
The organic electroluminescent device of the present invention comprises a first electrode, a second electrode disposed opposite to the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the at least one organic layer comprises the 1,3, 4-triaryl-substituted dibenzofuran compound of the present invention.
In one embodiment, as shown in fig. 7, the organic electroluminescent device of the present invention is obtained by disposing layers (for example, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10) in this order on a substrate 1.
The organic electroluminescent device of the present invention is not limited to such a structure, and for example, in the multilayer structure, one or some of the organic layers may be omitted. For example, the hole blocking layer 7 between the light emitting layer 6 and the electron transporting layer 8 may be omitted, the anode 2, the hole injecting layer 3, the hole transporting layer 4, the electron blocking layer 5, the light emitting layer 6, the electron transporting layer 8, the electron injecting layer 9 and the cathode 10 may be sequentially disposed on the substrate 1, or the hole injecting layer 3 between the anode 2 and the hole transporting layer 4, the hole blocking layer 7 between the light emitting layer 6 and the electron transporting layer 8, and the electron injecting layer 9 between the electron transporting layer 8 and the cathode 10 may be simultaneously omitted, and the anode 2, the hole transporting layer 4, the electron blocking layer 5, the light emitting layer 6, the electron transporting layer 8, and the cathode 10 may be sequentially disposed on the substrate 1, to finally obtain the corresponding organic electroluminescent device.
In addition to the above-described organic layers (e.g., light-emitting layer 6) comprising the compounds of the present invention (e.g., as host materials in light-emitting layer 6), the organic electroluminescent devices of the present invention can be fabricated by materials and methods well known in the art. In addition, in the case where the organic electroluminescent device includes a plurality of organic layers, the organic layers may be formed of the same or different substances. For example, the organic electroluminescent device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical vapor deposition) method such as sputtering or electron beam evaporation, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer. However, the manufacturing method is not limited thereto. As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
The anode of the organic electroluminescent device of the present invention may be made of a known electrode material. For example, an electrode material having a large work function, such as a metal of vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof is used; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; such as ZnO, al or SnO 2 A combination of metals such as Sb and the like and oxides; such as poly (3-alpha-methyl)Aminothiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]And conductive polymers such as (PEDOT), polypyrrole and polyaniline. Among these, ITO is preferable.
As the hole injection layer of the organic electroluminescent device of the present invention, a known material having hole injection properties can be used. For example, porphyrin compounds typified by copper phthalocyanine, naphthalene diamine compounds, star-shaped triphenylamine compounds, triphenylamine compounds having a structure in which 3 or more triphenylamine structures are linked by a single bond or a divalent group containing no hetero atom in the molecule, and the like, triphenylamine trimers, tetramers, and the like, and receptor-type dibenzofuran compounds such as hexacyanoazabenzophenanthrene, and the like, and coated polymer materials. These materials may be formed into thin films by a known method such as vapor deposition, spin coating, or ink jet.
As the hole transport layer of the organic electroluminescent device of the present invention, a known material having hole transport properties can be used. In addition, other known materials having hole-transporting properties may be used. For example, a compound containing m-carbazolylphenyl group; benzidine derivatives such as N, N ' -diphenyl-N, N ' -di (m-tolyl) benzidine (TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N ' -tetrabiphenyl benzidine, and the like; 1, 1-bis [ (di-4-tolylamino) phenyl ] cyclohexane (TAPC); various triphenylamine trimers and tetramers; 9,9' -triphenyl-9H, 9' H-3,3':6', 3' -tricarbazole (Tris-PCz), etc. These may be used alone or in a single layer form by mixing with other materials, or may be formed into a laminated structure of layers formed alone, a laminated structure of layers formed by mixing, or a laminated structure of layers formed alone and layers formed by mixing. These materials may be formed into thin films by a known method such as vapor deposition, spin coating, or ink jet.
In addition, in the hole injection layer or the hole transport layer, a substance obtained by further P-doping a material commonly used in the layer with tribromoaniline antimony hexachloride, an axial derivative, or the like, a polymer compound having a structure of a benzidine derivative such as TPD in a part of the structure, or the like may be used.
As the electron blocking layer of the organic electroluminescent device of the present invention, a known material having electron blocking properties may be used. In addition, other known compounds having an electron blocking effect may be used. Carbazole derivatives such as 4,4',4 "-tris (N-carbazolyl) triphenylamine (TCTA), 9-bis [4- (carbazol-9-yl) phenyl ] fluorene, 1, 3-bis (carbazol-9-yl) benzene (mCP), 2-bis (4-carbazol-9-yl) adamantane (Ad-Cz); a compound having a triphenylsilyl and triarylamine structure represented by 9- [4- (carbazol-9-yl) phenyl ] -9- [4- (triphenylsilyl) phenyl ] -9H-fluorene; monoamine compounds having high electron blocking properties, and compounds having an electron blocking effect such as various triphenylamine dimers. These may be used alone or in a single layer form by mixing with other materials, or may be formed into a laminated structure of layers formed alone, a laminated structure of layers formed by mixing, or a laminated structure of layers formed alone and layers formed by mixing. These materials may be formed into thin films by a known method such as vapor deposition, spin coating, or ink jet.
The light-emitting layer of the organic electroluminescent device of the present invention preferably contains the 1,3, 4-triaryl-substituted dibenzofuran-based compound of the present invention. In addition, alq may be used 3 Various metal complexes such as metal complexes of the first hydroxyquinoline derivative, compounds having a pyrimidine ring structure, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, and polyparaphenylene vinylene derivatives.
The light emitting layer may be composed of a host material and a doping material. As the host material, the 1,3, 4-triaryl-substituted dibenzofuran-based compound of the present invention is preferably contained. In addition, mCBP, mCP, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, dibenzofuran compounds having an indole ring as a partial structure of a condensed ring, and the like can be used. The dopant material preferably contains the dibenzofuran derivative of the present invention. In addition to these, aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like can be used. For example, pyrene derivatives, anthracene derivatives, quinacridones, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, spirobifluorene derivatives and the like can be cited. These may be used alone or in a single layer form by mixing with other materials, or may be formed into a laminated structure of layers formed alone, a laminated structure of layers formed by mixing, or a laminated structure of layers formed alone and layers formed by mixing. These materials may be formed into thin films by a known method such as vapor deposition, spin coating, or ink jet.
As the hole blocking layer of the organic electroluminescent device of the present invention, a known material having hole blocking properties can be used. In addition, other compounds having hole blocking properties may be used. For example, phenanthroline derivatives such as 2,4, 6-tris (3-phenyl) -1,3, 5-triazine (T2T), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), bathocuproine (BCP) and the like, metal complexes of quinolinol derivatives such as aluminum (III) bis (2-methyl-8-hydroxyquinoline) -4-phenylphenol salt (BAlq) and the like, and various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives and the like have a hole blocking effect. These may be used alone or in a single layer form by mixing with other materials, or may be formed into a laminated structure of layers formed alone, a laminated structure of layers formed by mixing, or a laminated structure of layers formed alone and layers formed by mixing. These materials may be formed into thin films by a known method such as vapor deposition, spin coating, or ink jet.
The above-described material having hole blocking property can also be used for formation of an electron transport layer described below. That is, by using the above known material having hole blocking property, a layer which serves as both a hole blocking layer and an electron transport layer can be formed.
As the electron transport layer of the organic electroluminescent device of the present invention, it is possible toMaterials with well known electron transport properties are used. In addition, other compounds having electron-transporting properties may be used. For example, in Alq 3 Metal complexes of hydroxyquinoline derivatives, including BAlq; various metal complexes; triazole derivatives; triazine derivatives; oxadiazole derivatives; pyridine derivatives; bis (10-hydroxybenzo [ H ]]Quinoline) beryllium (Be (bq) 2 ) The method comprises the steps of carrying out a first treatment on the surface of the Such as 2- [4- (9, 10-dinaphthyl-2-anthracen-2-yl) phenyl]-benzimidazole derivatives such as 1-phenyl-1H-benzimidazole (ETL); thiadiazole derivatives; an anthracene derivative; a carbodiimide derivative; quinoxaline derivatives; pyridoindole derivatives; phenanthroline derivatives; silole derivatives, and the like. These may be used alone or in a single layer form by mixing with other materials, or may be formed into a laminated structure of layers formed alone, a laminated structure of layers formed by mixing, or a laminated structure of layers formed alone and layers formed by mixing. These materials may be formed into thin films by a known method such as vapor deposition, spin coating, or ink jet.
The electron injection layer of the organic electroluminescent device of the present invention may be formed using a material known per se. For example, alkali metal salts such as lithium fluoride and cesium fluoride; alkaline earth metal salts such as magnesium fluoride; metal complexes of hydroxyquinoline derivatives such as lithium hydroxyquinoline; metal oxides such as alumina, and the like.
As a material commonly used for the electron transport layer or the electron injection layer, a material obtained by further doping a metal such as cesium or a triarylphosphine oxide derivative with N can be used.
As the cathode of the organic electroluminescent device of the present invention, it is preferable to use an electrode material having a low work function (e.g., aluminum, magnesium) or an alloy having a low work function (e.g., magnesium silver alloy, magnesium indium alloy, aluminum magnesium alloy) as the electrode material.
As the substrate of the present invention, a substrate in a conventional organic light emitting device, such as glass or plastic, may be used. In the present invention, a glass substrate is selected.
The production of the compound of the present invention and the organic electroluminescent device comprising the same is specifically described in the following examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereto. Reagents, materials, and instruments used in the examples described below were obtained by conventional commercial means, unless otherwise indicated.
Example 1: synthesis of Compound I-1
[ Synthesis of Compound M1 ]
The synthetic route for compound M1 is shown below:
dibenzo [ b, d ] as compound A was added sequentially to a clean 250mL three-necked flask under nitrogen atmosphere]Furan-4-ol (5 g), 1, 8-diazabicyclo [5.4.0 ]]Undec-7-ene (DBU) (0.2 g) and ultra-dry Dichloromethane (DCM) (20 mL). Triisopropylchlorosilane (TIPSCl) (6.3 g) was added dropwise under ice-water bath conditions, and after stirring for 0.5h, the system was gradually warmed to room temperature and reacted overnight under reflux. After the reaction is completed. The reaction was poured into water (ca. 100 mL) and extracted with DCM. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (stationary phase 350 mesh silica gel, eluent Petroleum Ether (PE): dcm=5:1, V/V) to give the product (8.9 g, yield 96%) as compound M1.MS (EI) m/z 340.12[ M ] + ]。
[ Synthesis of Compound M2 ]
The synthetic route for compound M2 is shown below:
to a clean 100mL single-necked flask under nitrogen atmosphere was added compound M1 (8.9 g) and DCM (50 mL) in order. N-bromosuccinimide (NBS) (2.3 g) was then added under ice-water bath, and NBS (2.35 g) was added after half an hour, after which the system was warmed to room temperature and reacted for 6 hours. After the reaction is completed, water is added, the organic phase is concentrated after liquid separation, and the organic phase is purified by column chromatography (stationary phase is 350 mesh silica gel)The eluent was PE: DCM=5:1, V/V) to give the product (10 g, 91% yield) as Compound M2.MS (EI) m/z 419.40[ M ] + ]。
[ Synthesis of Compound M3 ]
The synthetic route for compound M3 is shown below:
to a 100mL three-necked flask, under nitrogen atmosphere, compound M2 (10 g), (10-phenylanthracene-9-yl) boric acid (7.8 g) as compound B, tetrakis (triphenylphosphine) palladium (1.4 g) and potassium carbonate (3 g), and a mixed solvent of 1, 4-dioxane and water (100 mL,1, 4-dioxane: water=5:1, V/V) were added, and after the completion of the reaction, the mixture was stirred and dissolved, and the organic phase was separated and concentrated, and slurried with ethanol to give a solid product (12 g, yield 84%), namely compound M3.MS (EI) m/z 592.88[ M + ]。
[ Synthesis of Compound M4 ]
The synthetic route for compound M4 is shown below:
compound M3 (10 g) and tetra-n-butylammonium fluoride (TBAF) (8.8 g) were transferred to a 250mL three-necked flask under nitrogen atmosphere, tetrahydrofuran (THF) (150 mL) was added, dissolved with stirring, and cooled with an ice-water bath. After the reaction was completed, water was added, the organic phase was separated and concentrated to give a solid product (7 g, yield 95%) which was compound M4.MS (EI) m/z 436.18[ M + ]。
[ Synthesis of Compound M5 ]
The synthetic route for compound M5 is shown below:
to a clean 250mL three-necked flask, compound M4 (7 g) and a compound M were sequentially added under nitrogen atmosphereAcetic acid (AcOH) (100 mL). The system was gradually cooled to 0℃and then liquid bromine (2.7 g) was added dropwise to the reaction system, followed by reflux reaction for 3 hours. After the reaction was completed, the heating was stopped and cooled to room temperature. The reaction solution was poured into an aqueous sodium hydrogensulfite solution, extracted with DCM, and the organic phase was dried over anhydrous sodium sulfate and concentrated to give a solid product (7.9 g, yield 96%) as compound M5.MS (EI) m/z 515.43[ M + ]。
[ Synthesis of Compound M6 ]
The synthetic route for compound M6 is shown below:
to a clean 250mL three-necked flask under nitrogen atmosphere was added, in order, compound M5 (7.6 g), triethylamine (TEA) (4.2 g), and ultra-dry DCM (100 mL). The system was cooled to 0℃and triflic anhydride (Tf) was added 2 O) (5 g), followed by gradually warming to room temperature and reacting for 5h. After the reaction was completed, the reaction solution was poured into water (about 200 mL), extracted with DCM, the organic phase was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography (stationary phase: 350 mesh silica gel, eluent: PE: dcm=5:1, V/V), to obtain a solid product (8.0 g, yield 84%) which was compound M6.MS (EI) m/z 647.34[ M ] + ]。
[ Synthesis of Compound I-1 ]
The synthetic route for compound I-1 is shown below:
to a clean 250mL three-necked flask, compound M6 (4 g), phenylboronic acid (4.6 g) as compound C, tetrakis (triphenylphosphine) palladium (0.12 g) and potassium carbonate (3.0 g) were sequentially added under a nitrogen atmosphere, and a mixed solvent of toluene and water (100 mL, toluene: water=5:1, V/V). The system was gradually warmed to reflux and reacted overnight at reflux. After the reaction was completed, the heating was stopped and cooled to room temperature. The reaction was poured into water (about 200 mL), extracted with DCM, and the organic phase was free ofAfter drying over sodium sulfate, the mixture was concentrated to give a crude product, which was slurried with ethanol/toluene to give a solid product (3.2 g, yield 88%) as Compound I-1.MS (EI) m/z 572.33[ M + ]。
Examples 2 to 27: synthesis of specific Compounds of the invention
A series of specific compounds of the present invention were prepared by referring to the synthetic route of compound I-1 in example 1, and selecting the corresponding compound A, compound B and compound C, respectively (see Table 1).
TABLE 1
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Example 28: preparation of single-layer organic electroluminescent device 1 (organic EL device 1)
A hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transport layer 8, an electron injection layer 9, and a cathode 10 were sequentially formed on a transparent anode 2 (which was previously formed on a glass substrate 1) to prepare an organic electroluminescent device as shown in fig. 4 (but without a hole blocking layer 7).
Specifically, a glass substrate formed with an ITO electrode having a film thickness of 100nm was sonicated in a Decon 90 alkaline cleaning solution, rinsed in deionized water, rinsed three times each in acetone and ethanol, baked in a clean environment until the moisture was completely removed, rinsed with ultraviolet light and ozone, and bombarded with a low energy cation beam. Placing the glass substrate with ITO electrode into a vacuum chamber, and vacuumizing to 4×10 -4 -2×10 -5 Pa. 97wt% of HIL/3wt% of HTL was vapor-deposited on the ITO anode to form a layer having a film thickness of 10nm as a hole injection layer. The above-mentioned air spaceOn the hole injection layer, an HTL was vapor-deposited to form a layer with a film thickness of 20nm as a hole transport layer. An EBL was vapor deposited on the hole transport layer to form a layer having a thickness of 10nm as an electron blocking layer. On the electron blocking layer, the compound I-1 of example 1 as a host material and BD1 as a dopant material were co-evaporated to form a layer having a film thickness of 25nm, and the doped weight ratio of BD1 was 3wt% as a light emitting layer. On the light-emitting layer, 50wt% ETL/50wt% Liq was vapor-deposited to form a layer having a film thickness of 30nm as an electron transport layer. Yb was vapor deposited on the electron transport layer to form a layer having a film thickness of 1nm as an electron injection layer. And evaporating 90wt% of Mg/10wt% of Ag electrode on the electron injection layer, wherein the thickness is 15nm, and finally evaporating CPL on the Mg/Ag cathode to form a coating layer with the film thickness of 65nm, thus obtaining the organic EL device 1.
Examples 29 to 54: preparation of monolayer organic EL devices 2-27
Referring to the conditions for producing the organic EL device 1 in example 28, and using the compounds corresponding to the respective layer structures in table 2, organic EL devices 2 to 27 were produced, respectively.
Comparative examples 1 to 7: preparation of Single layer organic EL device comparative examples 1-7
Organic EL device comparative examples 1 to 7 were each prepared under the conditions for preparing the organic EL device 1 of reference example 28 using the compounds corresponding to the respective layer structures in table 2.
TABLE 2
Example 55: preparation of stacked organic electroluminescent device 28 (organic EL device 28)
The glass substrate formed with the ITO electrode having a film thickness of 100nm was sonicated in a Decon 90 alkaline cleaning solution, rinsed in deionized water, rinsed three times each in acetone and ethanol, baked in a clean environment until the moisture was completely removed, rinsed with ultraviolet light and ozone, and bombarded with a low energy cation beam. Placing the glass substrate with the ITO electrode into a vacuum cavity, and vacuumizingEmpty to 4 x 10 -4 -2×10 -5 Pa. 97wt% of HIL/3wt% of HTL was vapor-deposited on the ITO anode to form a layer having a film thickness of 10nm as a hole injection layer (denoted as hole injection layer 1). An HTL was vapor-deposited on the hole injection layer to form a layer having a film thickness of 20nm as a hole transport layer (referred to as a hole transport layer 1). An EBL was vapor deposited on the hole transport layer to form a layer having a film thickness of 10nm as an electron blocking layer (denoted as electron blocking layer 1). On the electron blocking layer, the compound I-1 of example 1 as a host material and BD1 as a dopant material were co-evaporated to form a layer having a film thickness of 25nm, and the dopant weight ratio of BD1 was 3wt% as a light emitting layer (referred to as light emitting layer 1). On the light-emitting layer, 50wt% ETL/50wt% Liq was vapor-deposited to form a layer having a film thickness of 30nm as an electron transport layer (referred to as an electron transport layer 1). On the electron transport layer, 50wt% ETL/50wt% Yb was vapor deposited to form a layer having a film thickness of 30nm as a connection layer. An Ag electrode was vapor-deposited on the connection layer to a thickness of 15nm, and then 97wt% of HIL/3wt% of HTL was vapor-deposited on the Ag electrode to form a layer having a thickness of 10nm as a hole injection layer (denoted as hole injection layer 2). An HTL was vapor-deposited on the hole injection layer to form a layer having a film thickness of 20nm as a hole transport layer (referred to as a hole transport layer 2). An EBL was vapor deposited on the hole transport layer to form a layer having a film thickness of 10nm as an electron blocking layer (denoted as electron blocking layer 2). On the electron blocking layer, the compound I-1 of example 1 as a host material and BD1 as a dopant material were co-evaporated to form a layer having a film thickness of 25nm, and the dopant weight ratio of BD1 was 3wt% as a light emitting layer (referred to as light emitting layer 2). On the light-emitting layer, 50wt% ETL/50wt% Liq was vapor-deposited to form a layer having a film thickness of 30nm as an electron transport layer (referred to as an electron transport layer 2). Yb was vapor deposited on the electron transport layer to form a layer having a film thickness of 1nm as an electron injection layer. And evaporating 90wt% of Mg/10wt% of Ag electrode on the electron injection layer to obtain a thickness of 15nm, and evaporating CPL on the Mg/Ag cathode to form a coating layer with a film thickness of 65nm, thereby obtaining the organic EL device 28.
Examples 56 to 81: preparation of stacked organic EL devices 29-54
Referring to the conditions for producing the organic EL device 28 in example 55, and using the compounds corresponding to the respective layer structures in table 3, organic EL devices 29 to 54 were produced, respectively.
Comparative examples 8 to 14: preparation of laminated organic EL device comparative examples 8 to 14
Organic EL device comparative examples 8 to 14 were each prepared under the conditions for preparing the organic EL device 28 in reference example 55, using the compounds corresponding to the respective layer structures in table 3.
TABLE 3 Table 3
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The organic EL devices in tables 2 and 3 use different types of 1,3, 4-triaryl-substituted dibenzofurans as blue host materials for the light-emitting layer in accordance with the present invention, and are matched with blue guest materials BD1, whereas the organic EL device comparative examples use the blue host materials containing the anthracenyl-monosubstituted dibenzofurans BH1, the anthracenyl-and phenyl-disubstituted dibenzofurans BH2, the anthracenyl-and phenyl (or methoxy) -trisubstituted dibenzofurans BH3 to BH7, and the same blue guest.
The structures of the organic EL device and the compound involved in the organic EL device comparative example are as follows:
the organic EL devices 1 to 54 fabricated in examples 28 to 81 and the organic EL devices comparative examples 1 to 14 fabricated in comparative examples 1 to 14 were measured for light emission characteristics when a direct current voltage was applied in the atmosphere at normal temperature. The current-luminance-voltage characteristics of the devices were obtained by the Keithley source measurement system (Keithley 2400Sourcemeter, keithley 2000 Currentmeter) with corrected silicon photodiodes, the electroluminescence spectra were measured by the Photo research company PR655 spectrometer, and the external quantum efficiency of the devices was calculated by the method described in adv.
TABLE 4 Table 4
As can be seen from table 4, the single-layer organic EL devices prepared from the compounds of the present invention were significantly higher than the single-layer organic EL device comparative examples prepared from BH1 to BH7 in terms of efficiency and lifetime, and exhibited lower voltages, indicating that devices using the compounds of the present invention as blue host materials generally have more excellent properties.
Meanwhile, the comparison of 7 organic EL device comparative examples shows that when the organic EL devices are arranged in order from long to short in service life, namely BH2 (aryl monosubstituted) > BH5 (2, 6, 7-triaryl substituted) > BH4 (1, 3, 7-triaryl substituted) > BH7 (1, 2, 8-triaryl substituted) =BH 3 (1, 7, 8-triaryl substituted) > BH6 (1-aryl-3, 4-dialkoxy substituted) > BH1 (aryl monosubstituted), and the organic EL devices are arranged in order from high to low in service life, namely BH1 (aryl monosubstituted) > BH6 (1-aryl-3, 4-dialkoxy substituted) > BH5 (2, 6, 7-triaryl substituted) =BH 7 (1, 2, 8-triaryl substituted) > BH4 (1, 3,7, 8-triaryl substituted) > BH2 (aryl monosubstituted), so that the efficiency and the service life of the organic EL devices can be obviously prolonged, but the performance of the devices can not be guaranteed even though the devices are used as a material with the two types of the existing devices in the service life and the two devices are in the order from short; the inventive compound adopts a 1,3, 4-triaryl substitution mode, thus not only improving the efficiency and service life of the device, but also reducing the operating voltage of the device, and the result is completely unexpected by the inventor.
Comparing compound I-1 with I-2, I-5 and I-66, it was found that the device corresponding to the dibenzofuran-based compound of the present invention containing deuterium atoms would be more efficient and have a longer lifetime than the device corresponding to the compound not containing deuterium atoms, presumably because the C-D bond is more stable than the C-H bond.
In addition, as is clear from the results shown in fig. 4, when the dibenzofuran-based compound of the present invention is used as a host material of a light-emitting layer in a device, the light-emitting pattern of the device is not affected by it, indicating that energy can be completely transferred to the light-emitting material in the device.
TABLE 5
As is clear from table 5, the properties (particularly voltage) of the laminated organic EL devices made from the compounds of the present invention are significantly improved as compared with the comparative examples of the laminated organic EL devices made from BH1 to BH7, indicating that the devices using the compounds of the present invention as the blue host material generally have more excellent properties.
Compared with the blue light main body material commonly used in the prior art, the 1,3, 4-triaryl substituted dibenzofuran compound can effectively reduce the working voltage, improve the external quantum efficiency and prolong the service life of the device.
Industrial applicability
The 1,3, 4-triaryl substituted dibenzofuran compound has excellent luminous efficiency, service life characteristic and low driving voltage. Therefore, organic electroluminescent devices, especially blue organic electroluminescent devices, having excellent service lives can be prepared from the compounds.
Claims (10)
1. A compound of the formula (I),
wherein,
Ar 1 、Ar 2 and Ar is a group 3 Each independently represents any one of the following groups optionally substituted with one or more deuterium atoms: phenyl, naphthyl, biphenyl, and phenyl-substituted naphthyl;
each R is 1 Each independently represents a hydrogen atom or a deuterium atom.
2. A compound according to claim 1, wherein,
Ar 1 、Ar 2 and Ar is a group 3 Each independently represents any one of the following groups:
wherein,
the dashed line represents a bond;
each R is 2 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
preferably Ar 1 Represents any one of the following groups:
and Ar is 2 And Ar is a group 3 Each independently represents any one of the following groups:
wherein,
the dashed line represents a bond;
each R is 2 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom.
3. A compound according to claim 1, wherein,
the compound is represented by the following general formula I-1, preferably by the following general formula I' -1,
wherein,
each R is 1 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
each R is 2 Each independently represents a hydrogen atom, a deuterium atom, a phenyl group or a phenyl group substituted by one or more deuterium atoms, and five R's attached to the same benzene ring 2 At most one of which is phenyl or phenyl substituted with one or more deuterium atoms; preferably, each R 2 Each independently represents a deuterium atom or a pentadeuterated phenyl group, and five R's attached to the same benzene ring 2 At most one of which is pentadeuterated phenyl;
Ar 1 as defined in formula I.
4. A compound according to claim 1, wherein,
the compound is represented by the following general formula I-2, preferably by the following general formula I' -2,
wherein,
each R is 1 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
each R is 2 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
Ar 1 as defined in formula I.
5. A compound according to claim 1, wherein,
the compound is represented by the following general formula I-3, preferably by the following general formula I' -3,
wherein,
each R is 1 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
each R is 2 Each independently represents a hydrogen atom or a deuterium atom, preferably a deuterium atom;
Ar 1 as defined in formula I.
6. A compound according to claim 1, wherein,
the compound is selected from any one of the following compounds:
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7. a light-emitting device comprising a first electrode, a second electrode provided opposite to the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, the at least one organic layer comprising the compound according to any one of claims 1 to 6;
preferably, the light emitting device is an organic electroluminescent device;
more preferably, the light emitting device is a blue organic electroluminescent device.
8. A light-emitting device according to claim 7, wherein,
the at least one organic layer is a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer or an electron transport layer;
preferably, the at least one organic layer is a light emitting layer;
preferably, the light emitting layer comprises a host material and a guest material, the host material comprising a compound according to any one of claims 1 to 6.
9. Use of a compound according to any one of claims 1 to 6 as a light-emitting material in the manufacture of a light-emitting device;
preferably, the luminescent material is a host material.
10. The use according to claim 9, characterized in that,
the light-emitting device is an organic electroluminescent device;
preferably, the light emitting device is a blue organic electroluminescent device.
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